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Sample records for ether-maleic anhydride polymer

  1. Improved lithographic performance for resists based on polymers having a vinyl ether-maleic anhydride (VEMA) backbone

    NASA Astrophysics Data System (ADS)

    Kim, Hyun-Woo; Choi, Sang-Jun; Jung, Dong-Won; Lee, Sook; Lee, Sung-Ho; Kang, Yool; Woo, Sang-Gyun; Moon, Joo-Tae; Kavanagh, Robert J.; Barclay, George G.; Orsula, George W.; Mattia, Joe; Caporale, Stefan; Adams, Timothy G.; Tanaka, Tsutomu; Kang, Doris

    2001-08-01

    ArF lithography, in combination with chemically amplified resists, has been investigated as one of the most promising technologies for producing patterns below 100 nm. In considering the polymer matrix for 193 nm photoresist applications, factors such as sensitivity, transparency to 193 nm radiation, adhesion to substrate, dry etch resistance, ease of synthesis, and availability of monomers are very critical. In these respects, remarkable progress has been made in development of ArF resist material. Polymers of acrylic and methacrylic esters show good imaging performance at 193 nm, but have insufficient dry-etch resistance under oxide or nitride etch condition. On the other hand, cyclic olefin-maleic anhydride (COMA) alternating copolymers exhibit good dry etch resistance, but have poor resolution capability. We previously reported a new platform, based on a vinyl ether-maleic anhydride (VEMA) alternating polymer system, that demonstrated both good resolution and high dry etch resistance. In this paper, VEMA systems with improved lithographic performance are presented. The new platform (VEMA) showed good performance in resolution, depth of focus (DOF), iso-dense bias, and post-etch roughness. With conventional illumination (NA=0.6, sigma=0.7), 120 nm dense line/space patterns with 0.4 (mu) M DOF were resolved. And 90 nm L/S patterns 0.6 (mu) M DOF were resolved with off-axis illumination (NA=0.63). Another important factor to be considered for the dry-etch process is post-etch roughness. In the case of VEMA system a clean surface was observed after etch under oxide, nitride, and poly conditions. The VEMA resist system is regarded as one of the most production-worthy material for real device manufacture.

  2. 40 CFR 721.10038 - Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Trimellitic anhydride, polymer with... Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol (generic... identified generically as trimellitic anhydride, polymer with substituted glycol, alkyl phenols...

  3. 40 CFR 721.10038 - Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Trimellitic anhydride, polymer with... Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol (generic... identified generically as trimellitic anhydride, polymer with substituted glycol, alkyl phenols...

  4. 40 CFR 721.10038 - Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Trimellitic anhydride, polymer with... Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol (generic... identified generically as trimellitic anhydride, polymer with substituted glycol, alkyl phenols and...

  5. 40 CFR 721.10038 - Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Trimellitic anhydride, polymer with... Trimellitic anhydride, polymer with substituted glycol, alkyl phenols and ethoxylated nonylphenol (generic... identified generically as trimellitic anhydride, polymer with substituted glycol, alkyl phenols and...

  6. Luteinizing hormone-releasing hormone targeted poly(methyl vinyl ether maleic acid) nanoparticles for doxorubicin delivery to MCF-7 breast cancer cells.

    PubMed

    Varshosaz, Jaleh; Jahanian-Najafabadi, Ali; Ghazzavi, Jila

    2016-08-01

    The purpose of this study was to design a targeted anti-cancer drug delivery system for breast cancer. Therefore, doxorubicin (DOX) loaded poly(methyl vinyl ether maleic acid) nanoparticles (NPs) were prepared by ionic cross-linking method using Zn(2+) ions. To optimise the effect of DOX/polymer ratio, Zn/polymer ratio, and stirrer rate a full factorial design was used and their effects on particle size, zeta potential, loading efficiency (LE, %), and release efficiency in 72 h (RE72, %) were studied. Targeted NPs were prepared by chemical coating of tiptorelin/polyallylamin conjugate on the surface of NPs by using 1-ethyl-3-(3-dimethylaminopropyl) carboiimid HCl as cross-linking agent. Conjugation efficiency was measured by Bradford assay. Conjugated triptorelin and targeted NPs were studied by Fourier-transform infrared spectroscopy (FTIR). The cytotoxicity of DOX loaded in targeted NPs and non-targeted ones were studied on MCF-7 cells which overexpress luteinizing hormone-releasing hormone (LHRH) receptors and SKOV3 cells as negative LHRH receptors using Thiazolyl blue tetrazolium bromide assay. The best results obtained from NPs prepared by DOX/polymer ratio of 5%, Zn/polymer ratio of 50%, and stirrer rate of 960 rpm. FTIR spectrum confirmed successful conjugation of triptorelin to NPs. The conjugation efficiency was about 70%. The targeted NPs showed significantly less IC50 for MCF-7 cells compared to free DOX and non-targeted NPs.

  7. 40 CFR 721.6183 - Amides, from ammonium hydroxide - maleic anhydride polymer and hydrogenated tallow alkyl amines...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... - maleic anhydride polymer and hydrogenated tallow alkyl amines, sodium salts, compds. with ethanolamine... Substances § 721.6183 Amides, from ammonium hydroxide - maleic anhydride polymer and hydrogenated tallow... anhydride polymer and hydrogenated tallow alkyl amines, sodium salts, compds. with ethanolamine (PMN...

  8. 40 CFR 721.6183 - Amides, from ammonium hydroxide - maleic anhydride polymer and hydrogenated tallow alkyl amines...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... - maleic anhydride polymer and hydrogenated tallow alkyl amines, sodium salts, compds. with ethanolamine... Substances § 721.6183 Amides, from ammonium hydroxide - maleic anhydride polymer and hydrogenated tallow... anhydride polymer and hydrogenated tallow alkyl amines, sodium salts, compds. with ethanolamine (PMN...

  9. 40 CFR 721.10316 - Dicyclopentadiene polymer with maleic anhydride and alkyl alcohols (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Dicyclopentadiene polymer with maleic... Significant New Uses for Specific Chemical Substances § 721.10316 Dicyclopentadiene polymer with maleic.... (1) The chemical substance identified generically as dicyclopentadiene polymer with maleic anhydride...

  10. 40 CFR 721.10316 - Dicyclopentadiene polymer with maleic anhydride and alkyl alcohols (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Dicyclopentadiene polymer with maleic... Significant New Uses for Specific Chemical Substances § 721.10316 Dicyclopentadiene polymer with maleic.... (1) The chemical substance identified generically as dicyclopentadiene polymer with maleic anhydride...

  11. 40 CFR 721.10316 - Dicyclopentadiene polymer with maleic anhydride and alkyl alcohols (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Dicyclopentadiene polymer with maleic... Significant New Uses for Specific Chemical Substances § 721.10316 Dicyclopentadiene polymer with maleic.... (1) The chemical substance identified generically as dicyclopentadiene polymer with maleic anhydride...

  12. Imide Oligomers Endcapped with Phenylethynl Phthalic Anhydrides and Polymers Therefrom

    NASA Technical Reports Server (NTRS)

    Hergenrother, Paul M. (Inventor); Smith, Joseph G., Jr. (Inventor)

    1998-01-01

    Controlled molecular weight phenylethynyl terminated imide oligomers (PETIs) have been prepared by the cyclodehydration of precursor phenylethynyl terminated amic acid oligomers. Amino terminated amic acid oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and subsequently endcapped with phenylethynyl phthalic anhydride(s) (PEPA). The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N.N-dimethylacetamide under nitrogen at room temperature. The amic acid oligomers are subsequently cyclodehydrated either thermally or cheznicauy to the corresponding imide oligomers. Direct preparation of PETIs from the reaction of dianhydxide(s) with an excess of diamine(s) and endcapped with phenylethynyl phthalic anhydride(s) has been performed in m-cresol. Phenylethynyl phthalic anhydrides are synthesized by the palladium catalyzed reaction of phenylacetylene with bromo substituted phthalic anhydrides in triethylamine. These new materials exhibit excellent properties and are potentially useful as adhesives, coatings, films, moldings and composite matrices.

  13. Imide oligomers endcapped with phenylethynyl phthalic anhydrides and polymers therefrom

    NASA Technical Reports Server (NTRS)

    Hergenrother, Paul M. (Inventor); Smith, Jr., Joseph G. (Inventor)

    1996-01-01

    Controlled molecular weight phenylethynyl terminated imide oligomers (PETIs) have been prepared by the cyclodehydration of precursor phenylethynyl terminated amic acid oligomers. Amino terminated amic acid oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and subsequently endcapped with phenylethynyl phthalic anhydride(s) (PEPA). The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide under nitrogen at room temperature. The amic acid oligomers are subsequently cyclodehydrated either thermally or chemically to the corresponding imide oligomers. Direct preparation of PETIs from the reaction of dianhydride(s) with an excess of diamine(s) and endcapped with phenylethynyl phthalic anhydride(s) has been performed in m-cresol. Phenylethynyl phthalic anhydrides are synthesized by the palladium catalyzed reaction of phenylacetylene with bromo substituted phthalic anhydrides in triethylamine. These new materials exhibit excellent properties and are potentially useful as adhesives, coatings, films, moldings and composite matrices.

  14. Biodegradable polymers derived from renewable resources: Highly branched copolymers of itaconic anhydride

    NASA Astrophysics Data System (ADS)

    Wallach, Joshua Andrew

    In an effort to design cyclic anhydride containing polymers that are derived from renewable resources and have biodegradable characteristics, three copolymer systems using itaconic anhydride have been studied. Two of the systems were copolymers with stearate based monomers; vinyl stearate and stearyl methacrylate, while the third was a copolymer with a methacrylate terminated poly (lactic acid) (PLA) macromonomer. For the stearate systems, stearyl methacrylate showed good copolymerization with equal conversions for both monomers. On the other hand vinyl stearate did not show as good results due to its decreased reactivity, which resulted in a copolymer highly enriched in itaconic anhydride with significant amounts of unreacted vinyl stearate under all copolymer compositions. These differing results were confirmed through analysis of reactivity ratios showing a results that are more favorable for copolymerization for the methacrylate system. Copolymers from both systems showed single melting transitions in a precarious range of 45--50°C arising from the stearyl side groups, though after quenching from the melt this shifted to below room temperature. Anhydride retention was confirmed through structural analysis. Similar to the stearyl methacrylate system, methacrylate terminated PLA macromonomers were copolymerized with itaconic anhydride. PLA's acceptance as a biodegradable material derived from renewable resources, make it a viable choice, with which to design anhydride containing copolymers. Good copolymerization was shown for all compositions studied with retention of the anhydride, though at high itaconic anhydride concentrations conversions were reduced significantly. Copolymers showed glass transition temperatures ranging from 32°C for 85 mole % PLA macromonomer to 73°C for 85 mole % itaconic anhydride. An effort to produce PLA macromonomers through a process of chemical recycling commercial PLA was also undertaken. Promising results were obtained showing

  15. Prolonged Hypocalcemic Effect by Pulmonary Delivery of Calcitonin Loaded Poly(Methyl Vinyl Ether Maleic Acid) Bioadhesive Nanoparticles

    PubMed Central

    Varshosaz, J.; Minaiyan, M.; Forghanian, M.

    2014-01-01

    The purpose of the present study was to design a pulmonary controlled release system of salmon calcitonin (sCT). Therefore, poly(methyl vinyl ether maleic acid) [P(MVEMA)] nanoparticles were prepared by ionic cross-linking method using Fe2+ and Zn2+ ions. Physicochemical properties of nanoparticles were studied in vitro. The stability of sCT in the optimized nanoparticles was studied by electrophoretic gel method. Plasma calcium levels until 48 h were determined in rats as pulmonary-free sCT solution or nanoparticles (25 μg·kg−1), iv solution of sCT (5 μg·kg−1), and pulmonary blank nanoparticles. The drug remained stable during fabrication and tests on nanoparticles. The optimized nanoparticles showed proper physicochemical properties. Normalized reduction of plasma calcium levels was at least 2.76 times higher in pulmonary sCT nanoparticles compared to free solution. The duration of hypocalcemic effect of pulmonary sCT nanoparticles was 24 h, while it was just 1 h for the iv solution. There was not any significant difference between normalized blood calcium levels reduction in pulmonary drug solution and iv injection. Pharmacological activity of nanoparticles after pulmonary delivery was 65% of the iv route. Pulmonary delivery of P(MVEMA) nanoparticles of sCT enhanced and prolonged the hypocalcemic effect of the drug significantly. PMID:24701588

  16. XPS depth profiling of derivatized amine and anhydride plasma polymers: Evidence of limitations of the derivatization approach

    NASA Astrophysics Data System (ADS)

    Manakhov, Anton; Michlíček, Miroslav; Felten, Alexandre; Pireaux, Jean-Jacques; Nečas, David; Zajíčková, Lenka

    2017-02-01

    The quantitative analysis of the chemistry at the surface of functional plasma polymers is highly important for the optimization of their deposition conditions and, therefore, for their subsequent applications. The chemical derivatization of amine and carboxyl-anhydride layers is a well-known technique already applied by many researchers, notwithstanding the known drawback of the derivatization procedures like side or uncomplete reactions that could lead to "unreliable" results. In this work, X-ray photoelectron spectroscopy (XPS) combined with depth profiling with argon clusters is applied for the first time to study derivatized amine and carboxyl-anhydride plasma polymer layers. It revealed an additional important parameter affecting the derivatization reliability, namely the permeation of the derivatizing molecule through the target analysed layer, i.e. the composite effect of the probe molecule size and the layer porosity. Amine-rich films prepared by RF low pressure plasma polymerization of cyclopropylamine were derivatized with trifluoromethyl benzaldehide (TFBA) and it was observed by that the XPS-determined NH2 concentration depth profile is rapidly decreasing over top ten nanometers of the layer. The anhydride-rich films prepared by atmospheric plasma co-polymerization of maleic anhydride and C2H2 have been reacted with, parafluoroaniline and trifluoroethyl amine. The decrease of the F signal in top surface layer of the anhydride films derivatized by the "large" parafluoroaniline was observed similarly as for the amine films but the derivatization with the smaller trifluoroethylamine (TFEA) led to a more homogenous depth profile. The data analysis suggests that the size of the derivatizing molecule is the main factor, showing that the very limited permeation of the TFBA molecule can lead to underestimated densities of primary amines if the XPS analysis is solely carried out at a low take-off angle. In contrast, TFEA is found to be an efficient

  17. Role of Cellulose Nanocrystals on the Microstructure of Maleic Anhydride Plasma Polymer Thin Films.

    PubMed

    Brioude, Michel M; Roucoules, Vincent; Haidara, Hamidou; Vonna, Laurent; Laborie, Marie-Pierre

    2015-07-01

    Recently, it was shown that the microstructure of a maleic anhydride plasma polymer (MAPP) could be tailored ab initio by adjusting the plasma process parameters. In this work, we aim to investigate the ability of cellulose nanocrystals (CNCs) to induce topographical structuration. Thus, a new approach was designed based on the deposition of MAPP on CNCs model surfaces. The nanocellulosic surfaces were produced by spin-coating the CNC suspension on a silicon wafer substrate and on a hydrophobic silicon wafer substrate patterned with circular hydrophilic microsized domains (diameter of 86.9 ± 4.9 μm), resulting in different degrees of CNC aggregation. By depositing the MAPP over these surfaces, it was possible to observe that the surface fraction of nanostructures increased from 20% to 35%. This observation suggests that CNCs can act as nucleation points resulting in more structures, although a critical density of the CNCs is required.

  18. New polymers for 193-nm single-layer resists based on substituted cycloolefins/maleic anhydride resins

    NASA Astrophysics Data System (ADS)

    Rushkin, Ilya L.; Houlihan, Francis M.; Kometani, Janet M.; Hutton, Richard S.; Timko, Allen G.; Reichmanis, Elsa; Nalamasu, Omkaram; Gabor, Allen H.; Medina, Arturo N.; Slater, Sydney G.; Neisser, Mark O.

    1999-06-01

    A series of new polymers for 193 nm single layer resist based on maleic anhydride/cycloolefin systems with minimum amount of acrylate units were synthesized. In order to minimize the acrylate content, the cycloolefin moiety of the polymers was functionalized with side groups designed to either promotes adhesion to silicon substrate and/or impart the imaging functionality. All polymers were prepared by free-radical polymerization in moderate to high yields and were characterized by variety of techniques. The initial lithographic evaluation of the new resists was carried out. It was found that acrylates can be successfully replaced with appropriately substituted cycloolefins to provide good resolution. The etch resistance of the new materials generally improves with increase in cycloolefin content. The Onishi and Kunz type plots will be discussed.

  19. Effect of Phthalic Anhydride Modified Soy Protein on Viscoelastic Properties of Polymer Composites

    USDA-ARS?s Scientific Manuscript database

    Phthalic anhydride (PA) modified soy protein isolates (SPI), both hydrolyzed and un-hydrolyzed, are investigated as reinforcement fillers in styrene-butadiene (SB) composites. The modification of SPI by PA increases the number of carboxylic acid functional groups on the protein surface and therefor...

  20. 21 CFR 177.1820 - Styrene-maleic anhydride copolymers.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... maleic anhydride monomer content. Residual maleic anhydride monomer content shall be determined by a gas chromatographic method titled “Determination of Residual Maleic Anhydride in Polymers by Gas...

  1. Development of a guided bone regeneration device using salicylic acid-poly(anhydride-ester) polymers and osteoconductive scaffolds.

    PubMed

    Mitchell, Ashley; Kim, Brian; Cottrell, Jessica; Snyder, Sabrina; Witek, Lukasz; Ricci, John; Uhrich, Kathryn E; O'Connor, J Patrick

    2014-03-01

    Successful repair of craniofacial and periodontal tissue defects ideally involves a combined therapy that includes inflammation modulation, control of soft tissue infiltration, and bone regeneration. In this study, an anti-inflammatory polymer, salicylic acid-based poly(anhydride-ester) (SAPAE) and a three-dimensional osteoconductive ceramic scaffold were evaluated as a combined guided bone regeneration (GBR) system for concurrent control of inflammation, soft tissue ingrowth, and bone repair in a rabbit cranial defect model. At time periods of 1, 3, and 8 weeks, five groups were compared: (1) scaffolds with a solid ceramic cap (as a GBR structure); (2) scaffolds with no cap; (3) scaffolds with a poly(lactide-glycolide) cap; (4) scaffolds with a slow release SAPAE polymer cap; and (5) scaffolds with a fast release SAPAE polymer cap. Cellular infiltration and bone formation in these scaffolds were evaluated to assess inflammation and bone repair capacity of the test groups. The SAPAE polymers suppressed inflammation and displayed no deleterious effect on bone formation. Additional work is warranted to optimize the anti-inflammatory action of the SAPAE, GBR suppression of soft tissue infiltration, and stimulation of bone formation in the scaffolds and create a composite device for successful repair of craniofacial and periodontal tissue defects.

  2. Effects of Secondary Polymer Covalently Attached to Monodisperse, Poly(maleic anhydride-styrene)-Modified Colloidal Silica on Dispersibility in Organic Solvent.

    PubMed

    Yoshinaga; Shimada; Nishida; Komatsu

    1999-06-15

    Effects of surface-grafted polymer on the dispersibility of polymer-silica composite particles in ethyl acetate-methanol cosolvent were investigated. The composite particles were prepared by a two-step modification of monodisperse colloidal silica (120 nm in diameter). Modifications were carried out by first reacting the surface silanol of the colloidal silica with maleic anhydride-styrene copolymer silane coupling agent to prevent aggregation and then grafting, in acetone or tetrahydrofuran, amino group-terminated poly(methyl acrylate), poly(methyl methacrylate), or polystyrene to the maleic anhydride moiety on the surface. For poly(methyl acrylate) and poly(methyl methacrylate) graftings, composite particles with long polymer chains aggregated in methanol-rich cosolvent due to insoluble secondary polymer chain interaction among the particles. Particles with a small amount of relatively low-molecular-weight secondary polymer were dispersible in the methanol content range from 0 to 90 vol%. Polystyrene-modified particles never aggregated, even in 90 vol% methanol solution. An ESR study of the suspension in ethyl acetate-hexane cosolvent suggested that the dispersibility of these composite particles in ethyl acetate-rich solution is attributable to steric repulsion between solvated and expanded secondary polymer chains among the particles. The dispersibility of the composite particles in methanol-rich solution was controlled by a delicate balance between the electrostatic repulsion and the interparticle attraction due to the desolvated and insoluble polymer chain interaction among the particles. Copyright 1999 Academic Press.

  3. 78 FR 76567 - Tall Oil, Polymer With Polyethylene Glycol and Succinic Anhydride Monopolyisobutylene Derivs...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2013-12-18

    .... Potentially affected entities may include: Crop production (NAICS code 111). Animal production (NAICS code 112... elements carbon, hydrogen, and oxygen. 3. The polymer does not contain as an integral part of its...

  4. Effect of maleic anhydride pretreatment on tensile bond strength of a silicone soft liner to a denture base polymer.

    PubMed

    Demir, Hakan; Soygun, Koray; Dogan, Arife; Keskin, Selda; Dogan, Orhan Murat; Bolayir, Giray

    2011-10-01

    To determine the effect of resin surface treatment with dissolved maleic anhydride in butanone added into primer on the tensile bond strength between an acrylic denture base resin and a silicone soft liner. To test tensile bond strength, standard dumbbell-shaped acrylic specimens were prepared. Five experimental groups, including the control, were tested (n = 5). Maleic anhydride solutions prepared in butanone at concentrations of 1%, 5%, 10% or 20% were then mixed with 1 ml of Primo adhesive and the mixtures were applied onto the resin bonding surfaces. Silicone liner material was applied to resin surfaces in the conventional manner. Tensile bond strength of the specimens was measured in a universal testing machine. Fractured surfaces were observed under the scanning electron microscope, and resulting chemical changes with the solutions used were analyzed spectroscopically. The highest bond strength value was obtained for the group treated with 5% maleic anhydride (2.53 ± 0.48 MPa); the lowest value was for the group treated with 20% maleic anhydride (1.59 ± 0.29 MPa). Mixed failure was the dominant type seen in the experimental groups. Spectroscopic analysis showed the interaction of the anhydride carbonyl groups with the Primo primer. The treatment of resin surfaces with maleic anhydride added to Primo adhesive effectively increased bond strength between silicone soft liner and denture base resin.

  5. 21 CFR 177.1820 - Styrene-maleic anhydride copolymers.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... maleic anhydride monomer content shall be determined by a gas chromatographic method titled “Determination of Residual Maleic Anhydride in Polymers by Gas Chromatography,” which is incorporated...

  6. 21 CFR 177.1820 - Styrene-maleic anhydride copolymers.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... maleic anhydride monomer content shall be determined by a gas chromatographic method titled “Determination of Residual Maleic Anhydride in Polymers by Gas Chromatography,” which is incorporated...

  7. 21 CFR 177.1820 - Styrene-maleic anhydride copolymers.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... maleic anhydride monomer content shall be determined by a gas chromatographic method titled “Determination of Residual Maleic Anhydride in Polymers by Gas Chromatography,” which is incorporated...

  8. Synthesis, Characterisation, and Evaluation of a Cross-Linked Disulphide Amide-Anhydride-Containing Polymer Based on Cysteine for Colonic Drug Delivery

    PubMed Central

    Lim, Vuanghao; Peh, Kok Khiang; Sahudin, Shariza

    2013-01-01

    The use of disulphide polymers, a low redox potential responsive delivery, is one strategy for targeting drugs to the colon so that they are specifically released there. The objective of this study was to synthesise a new cross-linked disulphide-containing polymer based on the amino acid cysteine as a colon drug delivery system and to evaluate the efficiency of the polymers for colon targeted drug delivery under the condition of a low redox potential. The disulphide cross-linked polymers were synthesised via air oxidation of 1,2-ethanedithiol and 3-mercapto-N-2-(3-mercaptopropionamide)-3-mercapto propionic anhydride (trithiol monomers) using different ratio combinations. Four types of polymers were synthesised: P10, P11, P151, and P15. All compounds synthesised were characterised by NMR, IR, LC-MS, CHNS analysis, Raman spectrometry, SEM-EDX, and elemental mapping. The synthesised polymers were evaluated in chemical reduction studies that were performed in zinc/acetic acid solution. The suitability of each polymer for use in colon-targeted drug delivery was investigated in vitro using simulated conditions. Chemical reduction studies showed that all polymers were reduced after 0.5–1.0 h, but different polymers had different thiol concentrations. The bacterial degradation studies showed that the polymers were biodegraded in the anaerobic colonic bacterial medium. Degradation was most pronounced for polymer P15. This result complements the general consensus that biodegradability depends on the swellability of polymers in an aqueous environment. Overall, these results suggest that the cross-linked disulphide-containing polymers described herein could be used as coatings for drugs delivered to the colon. PMID:24351841

  9. Synthesis, characterisation, and evaluation of a cross-linked disulphide amide-anhydride-containing polymer based on cysteine for colonic drug delivery.

    PubMed

    Lim, Vuanghao; Peh, Kok Khiang; Sahudin, Shariza

    2013-12-18

    The use of disulphide polymers, a low redox potential responsive delivery, is one strategy for targeting drugs to the colon so that they are specifically released there. The objective of this study was to synthesise a new cross-linked disulphide-containing polymer based on the amino acid cysteine as a colon drug delivery system and to evaluate the efficiency of the polymers for colon targeted drug delivery under the condition of a low redox potential. The disulphide cross-linked polymers were synthesised via air oxidation of 1,2-ethanedithiol and 3-mercapto-N-2-(3-mercaptopropionamide)-3-mercapto propionic anhydride (trithiol monomers) using different ratio combinations. Four types of polymers were synthesised: P10, P11, P151, and P15. All compounds synthesised were characterised by NMR, IR, LC-MS, CHNS analysis, Raman spectrometry, SEM-EDX, and elemental mapping. The synthesised polymers were evaluated in chemical reduction studies that were performed in zinc/acetic acid solution. The suitability of each polymer for use in colon-targeted drug delivery was investigated in vitro using simulated conditions. Chemical reduction studies showed that all polymers were reduced after 0.5-1.0 h, but different polymers had different thiol concentrations. The bacterial degradation studies showed that the polymers were biodegraded in the anaerobic colonic bacterial medium. Degradation was most pronounced for polymer P15. This result complements the general consensus that biodegradability depends on the swellability of polymers in an aqueous environment. Overall, these results suggest that the cross-linked disulphide-containing polymers described herein could be used as coatings for drugs delivered to the colon.

  10. Phthalic anhydride

    Integrated Risk Information System (IRIS)

    Phthalic anhydride ; CASRN 85 - 44 - 9 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic

  11. Maleic anhydride

    Integrated Risk Information System (IRIS)

    Maleic anhydride ; CASRN 108 - 31 - 6 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic

  12. Rheological Analysis of Polymer Interactions and Ageing of Poly(Methylvinylether-Co-Maleic Anhydride)/Poly(Vinyl Alcohol) Binary Networks and Their Effects on Mucoadhesion.

    PubMed

    Andrews, Gavin P; Laverty, Thomas P; Jones, David S

    2015-12-01

    Polymer blends of poly(vinylalcohol, PVA) and poly(methylvinylether-co-maleic anhydride, PMVE/MA) were formulated and their viscoelastic and mucoadhesive properties characterised. The viscoelastic and mucoadhesive properties were dependent on polymer concentration, molecular weight of PVA and PVA:PMVE/MA ratio. Alteration of these properties allowed platforms to be designed to offer defined rheological and mucoadhesive properties, properties that could not be achieved using monopolymeric platforms. A strong correlation was noted between the modulus of the polymeric blends and mucoadhesion. After storage, the polymeric blends underwent rheological structuring (ageing) with an attendant enhancement of mucoadhesion. In certain blends containing the highest molecular weight of PVA (146-186 kDa), storage ultimately resulted in an increase and then a significant decrease in the rheological and mucoadhesive properties, the latter phenomenon being accredited to polymer recrystallisation. Ageing of the rheological and mucoadhesive properties was modelled using an exponential growth model, allowing predictions of the storage period associated with the maxima in viscoelastic and mucoadhesive properties. These observations highlight the possible implications whenever interactive polymeric blends are employed in drug delivery. Caution is therefore urged whenever a formulation strategy based on interactive polymer blends is employed to ensure that ageing is fully understood and mathematically characterised.

  13. Carbon-13 cross-polarization magic-angle-spinning nuclear magnetic resonance investigation of the interactions between maleic anhydride grafted polypropylene and wood polymers.

    PubMed

    Rude, Erica; Laborie, Marie-Pierre G

    2008-05-01

    The chemical interactions between maleic anhydride grafted polypropylene (MAPP) and wood were studied with solid-state carbon-13 cross-polarization magic-angle-spinning nuclear magnetic resonance ((13)C CPMAS NMR) spectroscopy. MAPP was synthesized with 100% (13)C enrichment at the C(1) and C(4) carbons to allow detection of the [1,4-(13)C(2)]MAPP functional groups and was melt blended with cellulose, lignin, and maple wood. In the cellulose/MAPP blend, changes in (13)C CPMAS NMR corrected signal intensities for the anhydride and dicarboxylic maleic acid functionalities suggested that esterification may have occurred predominantly from the more numerous diacid carbons. A single proton longitudinal relaxation in the rotating frame, (H)T(1rho), for the MAPP and the cellulose carbons in the blend suggested that they were spin coupled, i.e., homogeneous on a 10-200 Angstrom scale. Esterification was also suggested in the lignin/MAPP blend. Furthermore, the more significant changes in the intensities of the carbonyl signals and (H)T(1rho) values suggested that lignin may be more reactive to MAPP than cellulose. Finally, when maple was melt blended with MAPP, the same trends in the (13)C CP-MAS NMR spectra and (H)T(1rho) behavior were observed as when MAPP was blended with cellulose or lignin. This study therefore clarifies that during melt compounding of wood with MAPP, esterification occurs with wood polymers, preferentially with lignin. Understanding the interactions of MAPP with wood is of significance for the development of natural-fiber-reinforced thermoplastic composites.

  14. Poly(ester anhydride)/mPEG amphiphilic block co-polymer nanoparticles as delivery devices for paclitaxel.

    PubMed

    Liang, Yanqin; Xiao, Li; Li, Yimei; Zhai, Yinglei; Xie, Chaopeng; Deng, Liandong; Dong, Anjie

    2011-01-01

    This work focused on the preparation and characterization of a novel amphiphilic block co-polymer and paclitaxel-loaded co-polymer nanoparticles (NPs) and in vitro evaluation of the release of paclitaxel and cytotoxicity of NPs. mPEG-b-P(OA-DLLA)-b-mPEG was prepared via melt polycondensation of methoxy poly(ethylene glycol) (mPEG), octadecanedioic acid (OA) and D,L-lactic acid (DLLA) and characterized by FT-IR, (1)H-NMR, (13)C-NMR, GPC, DSC and XRD. The paclitaxel-loaded mPEG-b-P(OA-DLLA)-b-mPEG NPs were prepared by nanoprecipitation and then characterized by LPSA, TEM and (1)H-NMR. In vitro release behaviors of the paclitaxel-loaded NPs were investigated by HPLC. In vitro cytotoxicity of NPs was evaluated by MTT assay with normal mouse lung fibroblast cells (L929) as model cells. The composition of mPEG-b-P(OA-DLLA)-b-mPEG is consistent with that of the designed co-polymer. The paclitaxel-loaded NPs are of spherical shape with core/shell structure and size smaller than 300 nm. Paclitaxel can be continuously released from the paclitaxel-loaded NPs and the in vitro release rate of paclitaxel decreases with increasing the content of the P(OA-DLLA) segments in the co-polymer. The mPEG-b-P(OA-DLLA)-b-mPEG NPs are non-toxic to L929. The results suggest that mPEG-b-P(OA-DLLA)-b-mPEG NPs are a potential candidate carrier material for the controlled delivery of paclitaxel and other hydrophobic compounds.

  15. Phenylethynyl Phthalic Anhydride

    NASA Technical Reports Server (NTRS)

    Hergenrother, Paul M. (Inventor); Smith, Joseph G., Jr. (Inventor)

    1997-01-01

    Controlled molecular weight PhenylEthynyl Terminated Imide oligomers (PETIs) have been prepared by the cyclodehydration of precursor phenylethynyl terminated amic acid oligomers. Amino terminated amic acid oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and subsequently endcapped with PhenylEthynyl Phthalic Anhydride(s) (PEPA). The polymerizations are carried out in polar aprotic solvents such as N-methyl-2pyrrolidinone or N N-dimethylacetamide under nitrogen at room temperature. The amic acid oligomers are subsequently cyclodehydrated either thermally or chemically to the corresponding imide oligomers. Direct preparation of PETIs from the reaction of dianhydride(s) with an excess of diamine(s) and endcapped with phenylethynyl phthalic anhydride(s) has been performed in m-cresol. Phenylethynyl phthalic anhydrides are synthesized by the palladium catalyzed reaction of phenylacetylene with bromo substituted phthalic anhydrides in triethylamine. These new materials exhibit excellent properties and are potentially useful as adhesives, coatings, films, moldings and composite matrices.

  16. Isomeric oxydiphthalic anhydride polyimides

    NASA Technical Reports Server (NTRS)

    Gerber, Margaret K.; Pratt, J. Richard; Stclair, Terry L.

    1988-01-01

    Much of the polyimide research at Langley Research Center has focused on isomeric modification of the diamine component; polyimides having considerably improved processability and adhesion have resulted. The present structure-property study was designed to investigate how isomeric attachment of the three oxydiphthalic anhydride (ODPA) polyimides affects their properties. Each dianhydride, 3,4,3',4'-oxydiphthalic anhydride (4,4'-OPDA,I), 2,3,2',3'-oxydiphthalic anhydride (3,3'-ODPA,II), and 2,3,3',4'-oxydiphthalic anhydride (3,4'-OPDA,III), was reacted with p-phenylenediamine, 4,4'-oxydianiline, 3,3'-diaminodiphenylsulfone, 3,3'-diaminobenzophenone, and 4,4'-bis(3-aminophenoxy)benzophenone in DMAc. The inherent viscosities of the resulting poly(amic acids) were determined. Thermally imidized films were studied for their creasability and solubility, as well as by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and wide angle X-ray scattering (WAXS). A comparison of these properties will be made.

  17. Succinic anhydrides from epoxides

    DOEpatents

    Coates, Geoffrey W.; Rowley, John M.

    2013-07-09

    Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

  18. Succinic anhydrides from epoxides

    DOEpatents

    Coates, Geoffrey W.; Rowley, John M.

    2016-06-28

    Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

  19. Succinic anhydrides from epoxides

    DOEpatents

    Coates, Geoffrey W; Rowley, John M

    2014-12-30

    Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

  20. Functional films of maleic anhydride copolymers under physiological conditions.

    PubMed

    Pompe, Tilo; Renner, Lars; Grimmer, Milauscha; Herold, Nicole; Werner, Carsten

    2005-09-16

    Reactivity and swelling of nanometer films of alternating maleic anhydride copolymers were investigated in dependence on the kind of comonomer and molar mass of copolymer in aqueous solution at pH 7.4 and pH 3.0 in order to reveal their characteristics under physiological conditions. Fully hydrolyzed (maleic acid) chains of the copolymers with styrene, propene, and ethylene comonomers covalently bound to SiO2 substrates showed a "mushroom" swelling behavior at pH 7.4 with a layer thickness scaling of N3/5. Decreasing the environmental pH was found to induce a comonomer-dependent shrinking or collapse of the immobilized polymers due to the change in ionization. From the swelling kinetics of non-hydrolyzed chains, the time constants and characteristics of swelling and anhydride hydrolysis were determined and found to depend on the type of comonomer. The short- and long-term swelling kinetics [l approximately t and approximately ln(t)1/2] were found to be in agreement with theoretical models of polymer swelling, while at intermediate time scales enhanced swelling was observed due to hydrolysis reaction of maleic anhydride groups. The findings elucidate the variety of properties of maleic anhydride copolymer films under physiological conditions, which can advantageously be applied for biofunctionalization of different templates.

  1. Maleic anhydride from normal butane

    SciTech Connect

    Cooley, S.D.; Doshi, B.

    1987-01-01

    Worldwide about one billion pounds of maleic anhydride is used annually in the manufacture of a number of commercially valuable products, including unsaturated polyester resins, agricultural chemicals, and lubricating oil additives. Maleic anhydride is not found in nature. It was first prepared in 1834 by heating malic acid (hydroxy-succinic acid, a compound found in apples and many other fruits). Maleic anhydride was not available commercially until ca. 1930 when the catalytic air oxidation of benzene was begun by National Aniline and Chemical on an industrial scale. The estimated worldwide production in 1985 was 1023 million pounds coming from more than 35 plants varying in capacity from 6 million pounds to 170 million pounds annually.

  2. Degradable poly(anhydride ester) implants: effects of localized salicylic acid release on bone.

    PubMed

    Erdmann, L; Macedo, B; Uhrich, K E

    2000-12-01

    Degradable poly(anhydride ester) implants in which the polymer backbone breaks down into salicylic acid (SA) were investigated. In this preliminary work, local release of SA from the poly(anhydride esters), thus classified as 'active polymers', on healthy bone and tissue was evaluated in vivo using a mouse model. Degradable polyanhydrides that break down into inactive by-products were used as control membranes because of their chemical similarity to the active polymers. Small polymer squares were inserted over the exposed palatal bone adjacent to the maxillary first molars. Active polymer membranes were placed on one side of the mouth, control polymers placed on the contra lateral side. Intraoral clinical examination showed that active polymer sites were less swollen and inflamed than control polymer sites. Histopathological examination at day 1 showed essentially no difference between control and active polymers. After 4 days, active polymer sites showed epithelial proliferation to a greater extent than the polyanhydride controls. After 20 days, active polymer sites showed greater thickness of new palatal bone and no resorptive areas, while control polymer sites showed less bone thickness as well as resorption including lacunae involving cementum and dentine. From these preliminary studies, we conclude that active polymers, namely poly(anhydride esters), stimulated new bone formation.

  3. Poly(butylene succinate-co-butylene adipate)/cellulose nanocrystal composites modified with phthalic anhydride.

    PubMed

    Zhang, Xuzhen; Zhang, Yong

    2015-12-10

    As a kind of biomass nanofiller for polymers, cellulose nanocrystal (CNC) has good mechanical properties and reinforcing capability. To improve the compatibility of poly(butylene succinate-co-butylene adipate) (PBSA)/CNC composites, phthalic anhydride was used as a compatilizer during melt mixing, leading to the significant improvement of the mechanical properties and thermal stability of the composites, which is related to the better dispersion of CNC in the composites. The addition of phthalic anhydride could accelerate the crystallization of PBSA component as evidenced by the curves of isothermal crystallization of the composites, but had little effect on the crystalline polymorphs of PBSA component. The addition of phthalic anhydride could strongly improve the hydrophobicity of the composites. The good mechanical properties, fast crystallization and improved hydrophobicity of PBSA/CNC composites with phthalic anhydride are favor to their practical commercial utilization.

  4. Controlled release from aspirin based linear biodegradable poly(anhydride esters) for anti-inflammatory activity.

    PubMed

    Dasgupta, Queeny; Movva, Sahitya; Chatterjee, Kaushik; Madras, Giridhar

    2017-08-07

    This work reports the synthesis of a novel, aspirin-loaded, linear poly (anhydride ester) and provides mechanistic insights into the release of aspirin from this polymer for anti-inflammatory activity. As compared to conventional drug delivery systems that rely on diffusion based release, incorporation of bioactives in the polymer backbone is challenging and high loading is difficult to achieve. In the present study, we exploit the pentafunctional sugar alcohol (xylitol) to provide sites for drug (aspirin) attachment at its non-terminal OH groups. The terminal OH groups are polymerized with a diacid anhydride. The hydrolysis of the anhydride and ester bonds under physiological conditions release aspirin from the matrix. The resulting poly(anhydride ester) has high drug loading (53%) and displays controlled release kinetics of aspirin. The polymer releases 8.5 % and 20%, of the loaded drug in one and four weeks, respectively and has a release rate constant of 0.0035h(-0.61). The release rate is suitable for its use as an anti-inflammatory agent without being cytotoxic. The polymer exhibits good cytocompatibility and anti-inflammatory properties and may find applications as injectable or as an implantable bioactive material. The physical insights into the release mechanism can provide development of other drug loaded polymers. Copyright © 2017 Elsevier B.V. All rights reserved.

  5. Salicylic acid (SA) bioaccessibility from SA-based poly(anhydride-ester).

    PubMed

    Rogers, Michael A; Yan, Yim-Fan; Ben-Elazar, Karen; Lan, Yaqi; Faig, Jonathan; Smith, Kervin; Uhrich, Kathryn E

    2014-09-08

    The bioaccessibility of salicylic acid (SA) can be effectively modified by incorporating the pharmacological compound directly into polymers such as poly(anhydride-esters). After simulated digestion conditions, the bioaccessibility of SA was observed to be statistically different (p < 0.0001) in each sample: 55.5 ± 2.0% for free SA, 31.2 ± 2.4% the SA-diglycolic acid polymer precursor (SADG), and 21.2 ± 3.1% for SADG-P (polymer). The release rates followed a zero-order release rate that was dependent on several factors, including (1) solubilization rate, (2) macroscopic erosion of the powdered polymer, (3) hydrolytic cleavage of the anhydride bonds, and (4) subsequent hydrolysis of the polymer precursor (SADG) to SA and diglycolic acid.

  6. Surface modification of cell culture carriers: routes to anhydride functionalization of polystyrene.

    PubMed

    Nitschke, Mirko; Ricciardi, Serena; Gramm, Stefan; Zschoche, Stefan; Herklotz, Manuela; Rivolo, Paola; Werner, Carsten

    2012-02-01

    Physico-chemical and topographical cues allow to control the behavior of adherent cells. Towards this goal, commercially available cell culture carriers can be finished with a laterally microstructured biomolecular functionalization. As shown in a previous study [Biomacromolecules 4 (2003) 1072], the anhydride moiety facilitates a simple and versatile way to protein binding. The present work addresses the technical issue of anhydride surface functionalization of polystyrene, the most common material for cell culture ware. Different approaches based on low pressure plasma, electron beam and ultraviolet light techniques (i.e. maleic anhydride plasma reactions; plasma, electron beam and UV immobilization of functional polymer thin films; grafting of functional polymers to plasma activated surfaces) are introduced and briefly illustrated with examples. Results are characterized by Fourier transform infrared (FTIR) spectroscopy, X-ray photoelectron spectroscopy (XPS) and ellipsometry. The different routes are compared in terms of technical feasibility and achievable surface properties. Copyright © 2011 Elsevier B.V. All rights reserved.

  7. Thermoplastic adhesives based on 4,4'-isophthaloyldiphthalic anhydride (IDPA)

    NASA Technical Reports Server (NTRS)

    Progar, Donald J.; Stclair, Terry L.; Pratt, J. Richard

    1988-01-01

    Thermoplastic polyimides were prepared and evaluated as adhesives. These materials are based on 4,4'-isophthaloyldiphathalic anhydride (IDAP) and either metaphenylene diamine (MPD) or 3,3'-diaminobenzophenone (DBAP). Both polymers exhibit excellent adhesive properties; however, the IDPA-MPD is the more attractive system because of a combination of high mechanical and physical properties as well as being made from commercially attractive monomers. The IDPA-MPD is an isomeric form of the commercially available adhesive and matrix resin, LARC-TPI and both systems have the same glass transition temperature and exhibit similar adhesive properties.

  8. Synthesis of ethylene maleic anhydride copolymer containing fungicides and evaluation of their effect for wood decay resistance

    Treesearch

    George C. Chen

    2008-01-01

    The aim of the present study was to combat wood decay based on the approach controlled-release biocides from polymers. The possibility of introducing polymer-bonded fungicides into the cell lumens was investigated. The synthesis of ethylene maleic anhydride copolymer containing pentachlorophenol (penta) and 8-hydroxy quinoline (8HQ) in N, N dimethyl formamide is...

  9. Synthesis and degradation characteristics of salicylic acid-derived poly(anhydride-esters).

    PubMed

    Erdmann, L; Uhrich, K E

    2000-10-01

    A biodegradable poly(anhydride-ester) was synthesized by melt condensation polymerization of the acetylated monomer to yield a novel polymeric prodrug. The polymer we have synthesized is composed of alkyl chains linked by ester bonds to aromatic moieties, specifically salicylic acid--the active component of aspirin. With the medicinal properties attributed to salicylic acid and the ease of metabolism, the incorporation of this compound into a polymer backbone yields a polymeric prodrug that may have potential in a variety of applications (i.e., inflammatory bowel disease). For these reasons, we have designed a synthetic scheme that yields the desired poly(anhydride-ester). The in vitro hydrolytic degradation of these polymers has been performed and results indicate that the polymer degradation rate is pH-dependent.

  10. A preliminary study on the dynamic-mechanical behaviour of compression moulded polypropylene/carbon fiber composites interfacially modified by a succinic anhydride grafted atactic polypropylene from polymer wastes

    NASA Astrophysics Data System (ADS)

    García-Martínez, Jesús María; Areso, Susana; Collar, Emilia P.

    2016-05-01

    Present communication is devoted to the study of the effect of a novel interfacial agent in polypropylene/carbon fibre composites. The interfacial agent used is a succinic anhydride grafted atactic polypropylene containing both succinic bridges and side grafts (aPP-SASA) and with 5.6% (5.6.10-4g/mol) of grafting content obtained at the GIP labs. The study considers the study dynamic-mechanical behaviour with temperature at a frequency of 1 hz to ascertain the differences in the interfacial activity. The samples were compression molded in order to isolate as far as possible the effect of the solely aPP-SASA in absence of those synergetic effects due to the preferential orientation of the fibres.

  11. Phenolic acid-based poly(anhydride-esters) as antioxidant biomaterialsa

    PubMed Central

    Prudencio, Almudena; Faig, Jonathan J.; Song, MinJung

    2015-01-01

    Poly(anhydride-esters) comprised of naturally occurring, non-toxic phenolic acids, namely syringic and vanillic acid, with antioxidant properties were prepared via solution polymerization methods. Polymer and polymer precursor physiochemical properties were characterized, including polymer molecular weight and thermal properties. In vitro release studies illustrated that polymer hydrolytic degradation was influenced by relative hydrophobicity and degree of methoxy substitution of the phenolic acids. Further, the released phenolic acids were found to maintain antioxidant potency relative to free phenolic acid controls as determined by a 2,2-diphenyl-1-picrylhydrazyl assay. Polymer cytotoxicity was assessed with L929 fibroblasts in polymer-containing media; appropriate cell morphology and high fibroblast proliferation were obtained for the polymers at the lower concentrations. These polymers deliver non-cytotoxic levels of naturally occurring antioxidants, which could be efficacious in topical delivery of antioxidant therapies. PMID:26425923

  12. Collagen functionalized with unsaturated cyclic anhydrides-interactions in solution and solid state.

    PubMed

    Potorac, S; Popa, M; Picton, L; Dulong, V; Verestiuc, L; Le Cerf, D

    2014-03-01

    Maleic anhydride (CMA) and itaconic anhydride modified collagen (CITA) were prepared as precursors for production of interpenetrated polymer networks (IPN). Calculated values for Huggins coefficient in aqueous diluted and semi-diluted solutions of modified collagen indicated a slightly tendency of aggregation for itaconic anhydride-modified collagen. In semi-diluted solution collagen (Coll) and CMA present slightly differences in the thixotropic behavior, while CITA has a pronounced thixotropic behavior. Flow and oscillatory measurements revealed an elastic behavior of the collagen solutions, pure and modified with MA or ITA, as the storage modulus (G') has always a superior value compared with the loss modulus (G″). The denaturation temperature (Td) of unmodified collagen increased from 34°C to 40°C for CMA and to 39°C for CITA respectively, by formation of covalent bonds that stabilize the triple helix.

  13. Langmuir and Langmuir-Blodgett films of a maleic anhydride derivative: effect of subphase divalent cations.

    PubMed

    Martín-García, B; Velázquez, M Mercedes; Pérez-Hernández, J A; Hernández-Toro, J

    2010-09-21

    We report the study of the equilibrium and dynamic properties of Langmuir monolayers of poly(styrene-co-maleic anhydride) partial 2-buthoxyethyl ester cumene terminated polymer and the effect of the Mg(NO(3))(2) addition in the water subphase on the film properties. Results show that the polymer monolayer becomes more expanded when the electrolyte concentration in the subphase increases. Dense polymer films aggregate at the interface. The aggregates are transferred onto silicon wafers using the Langmuir-Blodgett methodology and the morphology is observed by AFM. The structure of aggregates depends on the subphase composition of the Langmuir film transferred onto the silicon wafer.

  14. Maleic anhydride-g-low density polyethylene: Modification of LDPE molecular structure by γ-irradiation

    NASA Astrophysics Data System (ADS)

    Sheeja, Manaf, O.; Sujith, A.

    2017-06-01

    Polymer modification by radiation grafting of monomers onto polymers has received much attention recently. In the current study, γ-irradiation technique was used to achieve graft copolymerization of maleic anhydride (MA) onto low-density polyethylene (LDPE). To optimize, the process was performed at different γ-irradiation doses and MA concentration. The microstructure of grafted polymer film has been characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, differential scanning calorimetry, field emission-scanning electron microscopy, and atomic force microscopy. The studies performed made possible the selection of experimental protocols adequate for the production of new copolymeric materials with high grafting yield.

  15. Biologically Active Polymeric Coating Materials

    DTIC Science & Technology

    1975-04-01

    methacrylate P59» P6l, Polycondensation product of maleic anhydride, azelaic acid and propylene glycol crosslinked by tri-n-butyltin methacrylate. Since the...unsaturated alkyds, or through a condensation reaction of an organometallic oxide and a resin containing carboxylic acid groups as side chains. The...methyl vinyl ether/ maleic acid ) Tri-n-butyltin ester of high molecular weight poly (methyl vinyl ether/maleic acid ) Tri-n-butyltin ester of poly

  16. A new approach to reducing the flammability of layered double hydroxide (LDH)-based polymer composites: preparation and characterization of dye structure-intercalated LDH and its effect on the flammability of polypropylene-grafted maleic anhydride/d-LDH composites.

    PubMed

    Kang, Nian-Jun; Wang, De-Yi; Kutlu, Burak; Zhao, Peng-Cheng; Leuteritz, Andreas; Wagenknecht, Udo; Heinrich, Gert

    2013-09-25

    Dye structure-intercalated layered double hydroxide (d-LDH) was synthesized using a one-step method, and its intercalated behaviors have been characterized by Fourier transform infrared spectroscopy (FTIR), wide angle X-ray scattering (WAXS), scanning electron microscopy, thermogravimetric analysis (TGA), etc. As a novel functional potential fire-retarding nanofiller, it was used to prepare a polypropylene-grafted maleic anhydride (PP-g-MA)/d-LDH composite by refluxing the mixture of d-LDH and PP-g-MA in xylene, aiming to investigate its effect on the flammability of the PP-g-MA composite. The morphological properties, thermal stability, and flame retardant properties of the PP-g-MA/d-LDH composite were determined by FTIR, WAXS, transmission electron microscopy, TGA, and microscale combustion calorimetry. Compared with NO3-LDH (unmodified LDH) and LDH intercalated by sodium dodecylbenzenesulfonate (conventional organo-modified LDH), d-LDH can significantly decrease the heat release rate and the total heat release of the PP-g-MA composite, offering a new approach to imparting low flammability to LDH-based polymer composites.

  17. Synthesis of Hydroxy-Terminated Dinitropropyl Acrylate Polymers and Improved Characterization of Hydroxy-Terminated Prepolymers

    DTIC Science & Technology

    1983-03-01

    azelate polyesterdiol from Wittco PA Phthalic anhydride PCP Polycaprolactone diol from Union Carbide PDNPA Polydinitropropyl acrylate (our experimental... anhydride (AA) in the presence of N-methylimidazole (NMIM) (15)reported by Conners , and (b) phthalic anhydride (PA) in the presence of pyridine (PY...three meq sample of dried polymer was weighed into a 100 ml round bottom flask and 50 ml of phthalic anhydride stock solution (0.6 N) in anhydrous

  18. Biomaterial properties evaluation of poly(vinyl acetate- alt-maleic anhydride)/chitosan nanocapsules

    NASA Astrophysics Data System (ADS)

    Raţă, Delia Mihaela; Popa, Marcel; Chailan, Jean-François; Zamfir, Carmen Lăcrămioara; Peptu, Cătălina Anişoara

    2014-08-01

    Nanocapsules with diameter around 100 nm based on a natural polymer (chitosan) and a synthetic polymer poly(vinyl acetate- alt-maleic anhydride) [poly(MAVA)] by interfacial condensation method were prepared. The present study proposes a new type of biocompatible nanocapsules based on poly(vinyl acetate- alt-maleic anhydride-chitosan) (MCS) able to become a reliable support for inclusion and release of drugs. The spherical shape of the nanocapsules was evidenced by scanning electron microscopy. Nanocapsules presented a good Norfloxacin loading and release capacity. Haemocompatibility tests have demonstrated that the nanocapsules present a low toxicity and a good compatibility with sanguine medium. The biocompatibility properties of the nanocapsules after their intraperitoneal administration in rats were evidenced by histopathological examination of different organs (brain, liver, kidney, and lung). The results are encouraging and the nanocapsules can be used as controlled drug delivery systems.

  19. Evidence of glass transition in thin films of maleic anhydride derivatives: Effect of the surfactant coadsorption

    NASA Astrophysics Data System (ADS)

    López-Dıaz, D.; Velázquez, M. M.

    2008-08-01

    The glass transition temperature of poly (maleic anhydride-alt-1-octadecen) and poly (styrene-co-maleic anhydride) cumene-terminated thin films has been measured by mechanical relaxation of Langmuir films of these polymers. The dynamical properties show glass-like features (non-Arrhenius relaxation times and non-Debye mechanical response) interpreted by the coupling model. The glass transition temperature values determined by a mechanical relaxation experiment (step-compression) agree very well with those obtained by surface potential measurements. It is found that the glass transition temperature values in thin films decrease by about 100K as compared with those corresponding to the bulk polymers. The coadsorption of the water-insoluble surfactant DODAB decreases the glass transition temperature.

  20. Preparation of hydrophilic styrene maleic anhydride copolymer fibers for use in papermaking

    DOEpatents

    Rave, Terence W.

    1979-01-01

    Hydrophilic fibers may be prepared by discharging a heated and pressurized dispersion of a styrene-maleic anhydride copolymer into a zone of reduced temperature and pressure, and then modifying the fibers so produced by treatment with an aqueous admixture of selected cationic and anionic water-soluble, nitrogen-containing polymers. Blends of the hydrophilic fibers with wood pulp provide paper products having improved physical properties.

  1. Dimethylmaleic anhydride, a specific reagent for protein amino groups.

    PubMed

    de la Escalera, S; Palacián, E

    1989-01-01

    The reagent dimethylmaleic anhydride does not cause a stable modification of thiol compounds under the conditions used for modification of protein amino groups, in contrast to maleic and monomethylmaleic anhydrides, which produce an irreversible modification of sulfhydryl groups. This behavior and the low reactivity toward hydroxyamino acid residues, shown in a previous work, make dimethylmaleic anhydride a specific reagent for protein amino groups.

  2. 21 CFR 177.1820 - Styrene-maleic anhydride copolymers.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Styrene-maleic anhydride copolymers. 177.1820... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1820 Styrene-maleic anhydride copolymers. Styrene-maleic anhydride copolymers identified in paragraph (a) of this section may be...

  3. Improved zein articles using polyethylenemaleic anhydride

    USDA-ARS?s Scientific Manuscript database

    Developing corn protein (zein) articles with improved physical properties and solvent resistance will have a beneficial impact on companies that use corn. The effect of using the crosslinking reagent polyethylenemaleic anhydride (PEMA) on the properties and solubility of zein articles were studied. ...

  4. Ring-opening copolymerization of maleic anhydride with epoxides: a chain-growth approach to unsaturated polyesters.

    PubMed

    DiCiccio, Angela M; Coates, Geoffrey W

    2011-07-20

    We report the ring-opening copolymerization of maleic anhydride with a variety of epoxides catalyzed by a chromium(III) salen complex. Quantitative isomerization of the cis-maleate form of all polymers affords the trans-fumarate analogues. Addition of chain transfer reagents yields low M(n), narrow PDI polymer samples. This method provides access to a range of new unsaturated polyesters with versatile functionality, as well as the first synthesis of high molecular weight poly(propylene fumarate).

  5. Preparation of poly(glycidylmethacrylate-divinylbenzene) weak acid cation exchange stationary phases with succinic anhydride, phthalic anhydride, and maleic anhydride for ion chromatography.

    PubMed

    Liu, Junwei; Wang, Yong; Wu, Shuchao; Zhang, Peimin; Zhu, Yan

    2016-08-01

    In this work, poly(glycidylmethacrylate-divinylbenzene) microspheres were prepared and applied for the preparation of weak acid cation exchange stationary phases. Succinic anhydride, phthalic anhydride, and maleic anhydride were selected as carboxylation reagents to prepare three weak acid cation exchangers by direct chemical derivatization reaction without solvent or catalyst. The diameters and dispersity of the microspheres were characterized by scanning electron microscopy; the amount of accessible epoxy groups and mechanical stability were also measured. The weak acid cation exchangers were characterized by Fourier transform infrared spectroscopy; the content of carboxyl groups was measured by traditional acid base titration method. The chromatographic properties were characterized and compared by separating alkali, alkaline earth metal ions and ammonium and polar amines. The separation properties enhanced in the order of succinic anhydride, phthalic anhydride, and maleic anhydride modified poly(glycidylmethacrylate-divinylbenzene) cation exchangers.

  6. Poly(anhydride-esters) comprised exclusively of naturally occurring antimicrobials and EDTA: antioxidant and antibacterial activities.

    PubMed

    Carbone-Howell, Ashley L; Stebbins, Nicholas D; Uhrich, Kathryn E

    2014-05-12

    Carvacrol, thymol, and eugenol are naturally occurring phenolic compounds known to possess antimicrobial activity against a range of bacteria, as well as antioxidant activity. Biodegradable poly(anhydride-esters) composed of an ethylenediaminetetraacetic acid (EDTA) backbone and antimicrobial pendant groups (i.e., carvacrol, thymol, or eugenol) were synthesized via solution polymerization. The resulting polymers were characterized to confirm their chemical composition and understand their thermal properties and molecular weight. In vitro release studies demonstrated that polymer hydrolytic degradation was complete after 16 days, resulting in the release of free antimicrobials and EDTA. Antioxidant and antibacterial assays determined that polymer release media exhibited bioactivity similar to that of free compound, demonstrating that polymer incorporation and subsequent release had no effect on activity. These polymers completely degrade into components that are biologically relevant and have the capability to promote preservation of consumer products in the food and personal care industries via antimicrobial and antioxidant pathways.

  7. Poly(anhydride-esters) Comprised Exclusively of Naturally Occurring Antimicrobials and EDTA: Antioxidant and Antibacterial Activities

    PubMed Central

    2015-01-01

    Carvacrol, thymol, and eugenol are naturally occurring phenolic compounds known to possess antimicrobial activity against a range of bacteria, as well as antioxidant activity. Biodegradable poly(anhydride-esters) composed of an ethylenediaminetetraacetic acid (EDTA) backbone and antimicrobial pendant groups (i.e., carvacrol, thymol, or eugenol) were synthesized via solution polymerization. The resulting polymers were characterized to confirm their chemical composition and understand their thermal properties and molecular weight. In vitro release studies demonstrated that polymer hydrolytic degradation was complete after 16 days, resulting in the release of free antimicrobials and EDTA. Antioxidant and antibacterial assays determined that polymer release media exhibited bioactivity similar to that of free compound, demonstrating that polymer incorporation and subsequent release had no effect on activity. These polymers completely degrade into components that are biologically relevant and have the capability to promote preservation of consumer products in the food and personal care industries via antimicrobial and antioxidant pathways. PMID:24702678

  8. Design and Synthesis of Fast-Degrading Poly(anhydride-esters)

    PubMed Central

    Carbone, Ashley L.

    2009-01-01

    Fast-degrading, salicylate-based poly(anhydride-esters) were designed to degrade and release the active component, salicylic acid (SA), within 1 week. The polymer degradation was enhanced by using shorter or oxygen-containing aliphatic chains. A copolymer of diglycolic acid was also made with a salicylate-based diacid for comparison of polymer properties, including SA release. Both methods resulted in polyanhydrides with molecular weights ranging from 14 500 to 27 800 Da and displayed glass transition temperatures near physiological conditions, namely 33–40°C. the homo- and copolymers completely degraded within one week releasing the chemically incorporated SA. PMID:20161638

  9. Dicarboxylic acid anhydride condensation with compounds containing active methylene groups. 4: Some 4-nitrophthalic anhydride condensation reactions

    NASA Technical Reports Server (NTRS)

    Oskaja, V.; Rotberg, J.

    1985-01-01

    By 4-nitrophthalic anhydride condensation with acetoacetate in acetic anhydride and triethylamine solution with subsequent breakdown of the intermediate condensation product, 5-nitroindanedione-1,3 was obtained. A 4-nitrophthalic anhydride with acetic anhydride, according to reaction conditions, may yield two products: in the presence of potassium acetate and at high temperatures 4-(or 5-)-nitro-2-acetylbenzoic acid is formed: in the presence of triethylamine and at room temperature 5-( or 6-)-nitrophthalic acetic acid is isolated. A 4-nitrophthalic anhydride and malonic acid in pyridine solution according to temperature yield either 5-( or 6-)-nitrophthalic acetic acid or 4-(or 5-)-nitro-2-acetylbenzoic acid.

  10. Condensation of anhydrides or dicarboxylic acids with compounds containing active methylene groups. Part 19: Condensation of phthalic and substituted phthalic anhydrides with benzoylacetic ester

    NASA Technical Reports Server (NTRS)

    Rotberg, Y. T.; Oshkaya, V. P.

    1985-01-01

    Phthalylbenzoylacetic ester and its nitro and halogen derivatives were prepared through condensation of phthalic anhydride, nitrophthalic anhydride, and phthalic halide anhydride with benzoylacetic ester in a solution of acetic anhydride and triethylamine. The condensation of hemipinic acid anhydride proceeds similarly, but under more drastic conditions. Derivatives of indan-1,3-dione are also formed, with a small yield, in the reaction of nitrophthalic anhydrides with benzoylacetic ester in the presence of increased quantities of triethylamine.

  11. Chemicals from coal - The Eastman experience. [Anhydride

    SciTech Connect

    Larkins, T.H.

    1986-03-01

    Tennessee Eastman Company is a major producer of chemicals, fibers and plastics. It is located in Kingsport, Tennessee, headquarters for the Eastman Chemicals Division of Eastman Kodak Company. Eastman Companies employ a total of 12,250 people in Kingsport. Other domestic Eastman Chemicals Division plants are located in Texas, South Carolina, Arkansas and New York. The authors began to witness a flow of products from one of the most highly technical and sophisticated chemical processes in operation in the world. The Eastman ''Chemicals-from-Coal'' facility is not a sunfuel plant. To be sure, we are producing syngas from coal, but the syngas is used to produce acetic anhydride. Acetic anhydride is very important to Eastman. This chemical intermediate eventually finds its way into such diverse products as aspirin, cigarette filters, tool handles, and photographic film. It also is used to make other chemical intermediates such as cellulose esters, anhydrides, triacetin, and acetate ester solvents, all of which have a variety of end uses. The chemicals-from-coal project had its inception in the late 1960's when Eastman stepped up its program of energy conservation and began a search for lower cost chemical feedstocks. Our concern started before the national concern caused by a ten-fold increase in petroleum prices during the past decade.

  12. 78 FR 4792 - Epoxy Polymer; Exemption From the Requirement of a Tolerance

    Federal Register 2010, 2011, 2012, 2013, 2014

    2013-01-23

    ... AGENCY 40 CFR Part 180 Epoxy Polymer; Exemption From the Requirement of a Tolerance AGENCY: Environmental... requirement of a tolerance for residues of polymers of one or more diglycidyl ethers of bisphenol A...- cyclohexane-dicarboxylic anhydride and 1,2,3,6-tetrahydrophthalic anhydride; also referred to as epoxy...

  13. Biodegradable Salicylate-Based Poly(anhydride-ester) Microspheres For Controlled Insulin Delivery

    PubMed Central

    Delgado-Rivera, Roberto; Rosario-Meléndez, Roselin; Yu, Weiling; Uhrich, Kathryn E.

    2014-01-01

    Salicylate-based poly(anhydride-esters) (PAEs) chemically incorporate salicylic acid (SA) into the polymer backbone, which is then delivered in a controlled manner upon polymer hydrolysis. In this work, a salicylate-based PAE is a carrier to encapsulate and deliver insulin. Polymer microspheres were formulated using a water/oil/water double-emulsion solvent evaporation technique. The microspheres obtained had a smooth surface, high protein encapsulation efficiency, and relatively low emulsifier content. Insulin was released in vitro for 15 days, with no signs of aggregation or unfolding of the secondary structure. The released insulin also retained bioactivity in vitro. Concurrently, SA was released from the microspheres with polymer degradation and anti-inflammatory activity was observed. Based upon these results, the formulated microspheres enable simultaneous delivery of insulin and SA, both retaining bioactivity following processing. PMID:24027012

  14. Stability of a salicylate-based poly(anhydride-ester) to electron beam and gamma radiation

    PubMed Central

    Rosario-Meléndez, Roselin; Lavelle, Linda; Bodnar, Stanko; Halperin, Frederick; Harper, Ike; Griffin, Jeremy; Uhrich, Kathryn E.

    2011-01-01

    The effect of electron beam and gamma radiation on the physicochemical properties of a salicylate-based poly(anhydride-ester) was studied by exposing polymers to 0 (control), 25 and 50 kGy. After radiation exposure, salicylic acid release in vitro was monitored to assess any changes in drug release profiles. Molecular weight, glass transition temperature and decomposition temperature were evaluated for polymer chain scission and/or crosslinking as well as changes in thermal properties. Proton nuclear magnetic resonance and infrared spectroscopies were also used to determine polymer degradation and/or chain scission. In vitro cell studies were performed to identify cytocompatibility following radiation exposure. These studies demonstrate that the physicochemical properties of the polymer are not substantially affected by exposure to electron beam and gamma radiation. PMID:21909173

  15. Microwave Characterization of Propiolic Sulfuric Anhydride and Two Conformers of Acrylic Sulfuric Anhydride

    NASA Astrophysics Data System (ADS)

    Smith, CJ; Huff, Anna; Mackenzie, Becca; Leopold, Ken

    2017-06-01

    Sulfur trioxide reacts with propiolic acid and acrylic acid to form propiolic sulfuric anhydride (HC\\equivC-COOSO_{2}OH) and acrylic sulfuric anhydride (H_{2}C=CH-COOSO_{2}OH), respectively. Both species have been observed by chirped-pulse and conventional cavity microwave spectroscopy. In the case of acrylic acid, two conformers derived from the cis and trans form of the acid have been observed. The reaction mechanism and energetics are investigated by density functional theory and CCSD calculations. These results add to a growing body of evidence that establishes carboxylic sulfuric anhydrides, RCOOSO_{2}OH, as a class of molecules formed readily from SO_{3} + RCOOH in the gas phase and which, therefore, may be of significance in the nucleation and growth of atmospheric aerosol particles.

  16. Polymers.

    ERIC Educational Resources Information Center

    Tucker, David C.

    1986-01-01

    Presents an open-ended experiment which has students exploring polymer chemistry and reverse osmosis. This activity involves construction of a polymer membrane, use of it in a simple osmosis experiment, and application of its principles in solving a science-technology-society problem. (ML)

  17. Polymers.

    ERIC Educational Resources Information Center

    Tucker, David C.

    1986-01-01

    Presents an open-ended experiment which has students exploring polymer chemistry and reverse osmosis. This activity involves construction of a polymer membrane, use of it in a simple osmosis experiment, and application of its principles in solving a science-technology-society problem. (ML)

  18. Alternating copolymerization of propylene oxide with biorenewable terpene-based cyclic anhydrides: a sustainable route to aliphatic polyesters with high glass transition temperatures.

    PubMed

    Van Zee, Nathan J; Coates, Geoffrey W

    2015-02-23

    The alternating copolymerization of propylene oxide with terpene-based cyclic anhydrides catalyzed by chromium, cobalt, and aluminum salen complexes is reported. The use of the Diels-Alder adduct of α-terpinene and maleic anhydride as the cyclic anhydride comonomer results in amorphous polyesters that exhibit glass transition temperatures (Tg ) of up to 109 °C. The polymerization conditions and choice of catalyst have a dramatic impact on the molecular weight distribution, the relative stereochemistry of the diester units along the polymer chain, and ultimately the Tg of the resulting polymer. The aluminum salen complex exhibits exceptional selectivity for copolymerization without transesterification or epimerization side reactions. The resulting polyesters are highly alternating and have high molecular weights and narrow polydispersities.

  19. Exposure to cyclic anhydrides in welding: a new allergen-chlorendic anhydride.

    PubMed

    Pfäffli, Pirkko; Hämeilä, Mervi; Keskinen, Helena; Wirmoila, Ritva

    2002-11-01

    Respiratory effects associated with welding fumes have been manifested in welders as occupational asthma. Previous studies have concerned mainly the effects of metal fume exposure, although it has also been suggested that asthma may develop as a result of exposure to contaminants generated from painted metals. To determine whether welding fumes contain irritating and sensitizing anhydrides, air samples were collected during the repair welding of forest harvesters, which were painted with chlorinated polyester paint. Samples were collected with an assembly of a spiral glass trap inserted between a filter holder with a Teflon filter and a Tenax sampling tube. Sample analyses were with GC-MS and GC-ECD. Sensitizing anhydrides released from the paint into the air were primarily chlorendic anhydride (<2-44 microg/m(3)) and phthalic anhydride (11-21 microg/m(3)). Hydrogen chloride (HCl) and hexachlorocyclopentadiene were also found. Airborne HCl was measured with Dräger tubes. Since paint films are electrical insulators, the film around the welding seam was removed before arc welding. Removal of paint with an abrasive wheel caused the least exposure to HCl (<0.5 ppm) in contrast to burning with a gas fuel torch, (HCl approximately 5 ppm). HCl exposure was the highest (<0.5-20 ppm) during welding. It is recommended that dry paint coating be removed from an area around the seam with an abrasive wheel, not by burning, before welding.

  20. Optimize energy usage in phthalic anhydride units

    SciTech Connect

    de Virgiliis, A.; Gerunda, A.

    1982-05-01

    By maximizing the air to o-xylene ratios, Ftalital has developed a phthalic anhydride (PA) unit completely energy self-sufficient, generating its own electric power without affecting export steam. In the improved version of the production schemes a single-train synthesis reactors with 15,500 tubes each are used. These reactors have a production capacity of 35,000 metric tpy each and have operated with catalyst developed for high o-xylene-to-air ratios. Economic considerations are included.

  1. Biodegradable ferulic acid-containing poly(anhydride-ester): degradation products with controlled release and sustained antioxidant activity.

    PubMed

    Ouimet, Michelle A; Griffin, Jeremy; Carbone-Howell, Ashley L; Wu, Wen-Hsuan; Stebbins, Nicholas D; Di, Rong; Uhrich, Kathryn E

    2013-03-11

    Ferulic acid (FA) is an antioxidant and photoprotective agent used in biomedical and cosmetic formulations to prevent skin cancer and senescence. Although FA exhibits numerous health benefits, physicochemical instability leading to decomposition hinders its efficacy. To minimize inherent decomposition, a FA-containing biodegradable polymer was prepared via solution polymerization to chemically incorporate FA into a poly(anhydride-ester). The polymer was characterized using nuclear magnetic resonance and infrared spectroscopies. The molecular weight and thermal properties were also determined. In vitro studies demonstrated that the polymer was hydrolytically degradable, thus providing controlled release of the chemically incorporated bioactive with no detectable decomposition. The polymer degradation products were found to exhibit antioxidant and antibacterial activity comparable to that of free FA, and in vitro cell viability studies demonstrated that the polymer is noncytotoxic toward fibroblasts. This renders the polymer a potential candidate for use as a controlled release system for skin care formulations.

  2. Biodegradable Ferulic Acid-containing Poly(anhydride-ester): Degradation Products with Controlled Release and Sustained Antioxidant Activity

    PubMed Central

    Ouimet, Michelle A.; Griffin, Jeremy; Carbone-Howell, Ashley L.; Wu, Wen-Hsuan; Stebbins, Nicholas D.; Di, Rong; Uhrich, Kathryn E.

    2013-01-01

    Ferulic acid (FA) is an antioxidant and photoprotective agent used in biomedical and cosmetic formulations to prevent skin cancer and senescence. Although FA exhibits numerous health benefits, physicochemical instability leading to decomposition hinders its efficacy. To minimize inherent decomposition, a FA-containing biodegradable polymer was prepared via solution polymerization to chemically incorporate FA into a poly(anhydride-ester). The polymer was characterized using nuclear magnetic resonance and infrared spectroscopies. The molecular weight and thermal properties were also determined. In vitro studies demonstrated that the polymer was hydrolytically degradable, thus providing controlled release of the chemically incorporated bioactive with no detectable decomposition. The polymer degradation products were found to exhibit antioxidant and antibacterial activity comparable to free FA and in vitro cell viability studies demonstrated that the polymer is non-cytotoxic towards fibroblasts. This renders the polymer a potential candidate for use as a controlled release system for skin care formulations. PMID:23327626

  3. Preparation of {alpha}, {beta}-unsaturated carboxylic acids and anhydrides

    DOEpatents

    Spivey, J.J.; Gogate, M.R.; Zoeller, J.R.; Tustin, G.C.

    1998-01-20

    Disclosed is a process for the preparation of {alpha},{beta}-unsaturated carboxylic acids and anhydrides thereof which comprises contacting formaldehyde or a source of formaldehyde with a carboxylic anhydride in the presence of a catalyst comprising mixed oxides of vanadium, phosphorus and, optionally, a third component selected from titanium, aluminum or, preferably silicon.

  4. Preparation of .alpha., .beta.-unsaturated carboxylic acids and anhydrides

    DOEpatents

    Spivey, James Jerry; Gogate, Makarand Ratnakav; Zoeller, Joseph Robert; Tustin, Gerald Charles

    1998-01-01

    Disclosed is a process for the preparation of .alpha.,.beta.-unsaturated carboxylic acids and anhydrides thereof which comprises contacting formaldehyde or a source of formaldehyde with a carboxylic anhydride in the presence of a catalyst comprising mixed oxides of vanadium, phosphorus and, optionally, a third component selected from titanium, aluminum or, preferably silicon.

  5. Synthesis of Oxyarylene BBB Polymers.

    DTIC Science & Technology

    1975-06-01

    is only soluble in highly corrosive solvents. A series of BBB polymers has been synthesized by the reaction of 1,4,5,8- naphthalenetetracarboxylic...an increased number of rotational sites along the polymer backbone were soluble in m- cresol and exhibited glass transition temperatures in the 300... corrosive solvents. A series of BBB polymers has been synthesized by the reaction of 1,4,5,8-naphthalenetetracarboxylic acid anhydride with oxyarylene

  6. Characterization and in vitro degradation of salicylate-derived poly(anhydride-ester microspheres).

    PubMed

    Yeagy, Brian A; Prudencio, Almudena; Schmeltzer, Robert C; Uhrich, Kathryn E; Cook, Thomas J

    2006-09-01

    The aim of this study was to investigate how glass transition temperature (Tg) influenced polymer microsphere formation and degradation of three chemically, similar novel salicylatebased poly(anhydride-esters): poly[1,6-bis(o-carboxyphenoxy)hexanoate] (CPH), Tg = 59 degrees C; poly[1,8-bis(o-carboxyphenoxy)octanoate] (CPO), Tg = 30 degrees C; and poly[1,10-bis(ocarboxyphenoxy) decanoate] (CPD), Tg = 27 degrees C. Microspheres of these polymers were prepared using a modified oil-in-water solvent evaporation method and processed by either resuspension or washed by centrifugation. The morphology of the microspheres determined by scanning electron microscopy (SEM) revealed that an extra washing step appears to increase aggregation as the Tg decreases; whereas only limited aggregation occurred in the polymer with the lowest Tg, CPD, in those not washed by centrifugation. Residual polyvinyl alcohol apparently affected the drug release rates from the microspheres by a stabilization process that produced an 8 h lag time and a 5% decrease in the amount of drug released over a 7 day period compared to microspheres washed free of PVA. These results demonstrate that salicylate-based poly(anhydride-esters) with sufficiently high Tgs, can be processed into microspheres that release salicylate over a time period amenable for drug delivery applications.

  7. Plasma Polymerisation of Maleic Anhydride: Just what are the right deposition conditions?

    PubMed Central

    Mishra, Gautam; McArthur, Sally L.

    2010-01-01

    Maleic anhydride plasma polymers enable amine containing biomolecules and polymers to be covalently coupled to a surface from an aqueous solution without any intermediate chemistry. The challenge in developing these functionally active plasma polymers lies in determining the optimal deposition conditions for producing a stable, highly active film. Unlike many previous studies that explore highly varied pulsed and continuous wave (CW) deposition conditions, this paper focuses on the comparison of films deposited under the same low nominal power conditions (1 W) and compares a range of CW, ms and µs pulsing parameters that can be used to produce this power condition. The use of attenuated total reflectance – Fourier transform infra red spectroscopy (ATR-FTIR) and X-ray photoelectron spectroscopy (XPS) has enabled the quantitative examination of the effects of processing parameters on the chemical functionality of the films. For the first time, the molecular specificity, surface sensitivity and high mass resolution of time-of-flight static secondary ion mass spectrometry (ToF-SSIMS) has been exploited to compare these films and multivariate analysis techniques used to explore the relationships between plasma processing parameters and surface chemistry. The results of the studies clearly demonstrate that a range of conditions can produce maleic anhydride films, with optimal functionality seen under µs pulsing regimes. Critically, the study demonstrates that the tight control and monitoring of the deposition parameters is critical if these films are to be manufactured with optimal functionality, stability and minimum processing time. PMID:20443591

  8. Stereocomplexes of enantiomeric lactic acid and sebacic acid ester-anhydride triblock copolymers.

    PubMed

    Slivniak, Raia; Domb, Abraham J

    2002-01-01

    A systematic study on the synthesis, characterization, degradation, and drug release of d-, l-, and dl-poly(lactic acid) (PLA)-terminated poly(sebacic acid) (PSA) and their stereocomplexes is reported. PLA-terminated sebacic acid polymers were synthesized by melt condensation of the acetate anhydride derivatives of PLA oligomers and sebacic anhydride oligomers to yield ABA triblock copolymers of molecular weights between 3000 and 9000 that melt at temperatures between 35 and 80 degrees C. Pairs of the corresponding enantiomeric ABA copolymers composed of l-PLA-PSA-l-PLA and d-PLA-PSA-d-PLA were solvent mixed to form stereocomplexes. The formed stereocomplexes exhibited higher crystalline melting temperature than the enantiomeric polymers, which indicate stereocomplex formulation. The PLA terminals had a significant effect on the polymer degradation and drug release rate. PSA with up to 20% w/w of PLA terminals degraded and released the incorporated drug for more than 3 weeks as compared with 10 days for PSA homopolymer.

  9. Biocompatibility of polysebacic anhydride microparticles with chondrocytes in engineered cartilage

    PubMed Central

    Ponnurangam, Sathish; O'Connell, Grace D.; Hung, Clark T.; Somasundaran, Ponisseril

    2015-01-01

    One of main challenges in developing clinically relevant engineered cartilage is overcoming limited nutrient diffusion due to progressive elaboration of extracellular matrix at the periphery of the construct. Macro-channels have been used to decrease the nutrient path-length; however, the channels become occluded with matrix within weeks in culture, reducing nutrient diffusion. Alternatively, microparticles can be imbedded throughout the scaffold to provide localized nutrient delivery. In this study, we evaluated biocompatibility of polysebacic anhydride (PSA) polymers and the effectiveness of PSA-based microparticles for short-term delivery of nutrients in engineered cartilage. PSA-based microparticles were biocompatible with juvenile bovine chondrocytes for concentrations up to 2mg/mL; however, cytotoxicity was observed at 20mg/mL. Cytotoxicity at high concentrations is likely due to intracellular accumulation of PSA degradation products and resulting lipotoxicity. Cytotoxicity of PSA was partially reversed in the presence of bovine serum albumin. In conclusion, the findings from this study demonstrate concentration-dependent biocompatibility of PSA-based microparticles and potential application as a nutrient delivery vehicle that can be imbedded in scaffolds for tissue engineering. PMID:26398146

  10. Antimocrobial Polymer

    DOEpatents

    McDonald, William F.; Huang, Zhi-Heng; Wright, Stacy C.

    2005-09-06

    A polymeric composition having antimicrobial properties and a process for rendering the surface of a substrate antimicrobial are disclosed. The composition comprises a crosslinked chemical combination of (i) a polymer having amino group-containing side chains along a backbone forming the polymer, (ii) an antimicrobial agent selected from quaternary ammonium compounds, gentian violet compounds, substituted or unsubstituted phenols, biguanide compounds, iodine compounds, and mixtures thereof, and (iii) a crosslinking agent containing functional groups capable of reacting with the amino groups. In one embodiment, the polymer is a polyamide formed from a maleic anhydride or maleic acid ester monomer and alkylamines thereby producing a polyamide having amino substituted alkyl chains on one side of the polyamide backbone; the crosslinking agent is a phosphine having the general formula (A)3P wherein A is hydroxyalkyl; and the antimicrobial agent is chlorhexidine, dimethylchlorophenol, cetyl pyridinium chloride, gentian violet, triclosan, thymol, iodine, and mixtures thereof.

  11. Antimicrobial Polymer

    DOEpatents

    McDonald, William F.; Wright, Stacy C.; Taylor, Andrew C.

    2004-09-28

    A polymeric composition having antimicrobial properties and a process for rendering the surface of a substrate antimicrobial are disclosed. The polymeric composition comprises a crosslinked chemical combination of (i) a polymer having amino group-containing side chains along a backbone forming the polymer, (ii) an antimicrobial agent selected from metals, metal alloys, metal salts, metal complexes and mixtures thereof, and (iii) a crosslinking agent containing functional groups capable of reacting with the amino groups. In one example embodiment, the polymer is a polyamide formed from a maleic anhydride or maleic acid ester monomer and alkylamines thereby producing a polyamide having amino substituted alkyl chains on one side of the polyamide backbone; the crosslinking agent is a phosphine having the general formula (A).sub.3 P wherein A is hydroxyalkyl; and the metallic antimicrobial agent is selected from chelated silver ions, silver metal, chelated copper ions, copper metal, chelated zinc ions, zinc metal and mixtures thereof.

  12. Heterogeneous catalyst for the production of ethylidene diacetate from acetic anhydride

    DOEpatents

    Ramprasad, Dorai; Waller, Francis Joseph

    1998-01-01

    This invention relates to a process for producing ethylidene diacetate by the reaction of acetic anhydride, acetic acid, hydrogen and carbon monoxide at elevated temperatures and pressures in the presence of an alkyl halide and a heterogeneous, bifunctional catalyst that is stable to hydrogenation and comprises an insoluble polymer having pendant quaternized heteroatoms, some of which heteroatoms are ionically bonded to anionic Group VIII metal complexes, the remainder of the heteroatoms being bonded to iodide. In contrast to prior art processes, no accelerator (promoter) is necessary to achieve the catalytic reaction and the products are easily separated from the catalyst by filtration. The catalyst can be recycled without loss in activity.

  13. Heterogeneous catalyst for the production of ethylidene diacetate from acetic anhydride

    DOEpatents

    Ramprasad, D.; Waller, F.J.

    1998-06-16

    This invention relates to a process for producing ethylidene diacetate by the reaction of acetic anhydride, acetic acid, hydrogen and carbon monoxide at elevated temperatures and pressures in the presence of an alkyl halide and a heterogeneous, bifunctional catalyst that is stable to hydrogenation and comprises an insoluble polymer having pendant quaternized heteroatoms, some of which heteroatoms are ionically bonded to anionic Group VIII metal complexes, the remainder of the heteroatoms being bonded to iodide. In contrast to prior art processes, no accelerator (promoter) is necessary to achieve the catalytic reaction and the products are easily separated from the catalyst by filtration. The catalyst can be recycled without loss in activity.

  14. Biocompatible photocrosslinked poly(ester anhydride) based on functionalized poly(epsilon-caprolactone) prepolymer shows surface erosion controlled drug release in vitro and in vivo.

    PubMed

    Mönkäre, J; Hakala, R A; Vlasova, M A; Huotari, A; Kilpeläinen, M; Kiviniemi, A; Meretoja, V; Herzig, K H; Korhonen, H; Seppälä, J V; Järvinen, K

    2010-09-15

    Star-shaped poly(epsilon-caprolactone) oligomers functionalized with succinic anhydride were used as prepolymers to prepare photocrosslinked poly(ester anhydride) to evaluate their in vivo drug delivery functionality and biocompatibility. Thus, in this work, erosion, drug release and safety of the photocrosslinked poly(ester anhydride) were examined in vitro and in vivo. A small water-soluble drug, propranolol HCl (M(w) 296 g/mol, solubility 50 mg/ml), was used as the model drug in an evaluation of the erosion controlled release. Drug-free and drug-loaded (10-60% w/w) poly(ester anhydride) discoids eroded in vitro (pH 7.4 buffer, +37 degrees C) linearly within 24-48 h. A strong correlation between the polymer erosion and the linear drug release in vitro was observed, indicating that the release had been controlled by the erosion of the polymer. Similarly, in vivo studies (s.c. implantation of discoids in rats) indicated that surface erosion controlled drug release from the discoids (drug loading 40% w/w). Oligomers did not decrease cell viability in vitro and the implanted discoids (s.c., rats) did not evoke any cytokine activity in vivo. In summary, surface erosion controlled drug release and the safety of photocrosslinked poly(ester anhydride) were demonstrated in this study.

  15. A Demonstration of Polymer Crosslinking and Gel Formation Without Heating

    ERIC Educational Resources Information Center

    Ross, Joseph H.

    1977-01-01

    Describes an undergraduate experiment in which Gantrez AN polymer chains are crosslinked at the anhydride groups by the addition of the hydroxyl groups of triethanolamine, which also acts as a basic catalyst. (MLH)

  16. Tunable drug release profiles from salicylate-based poly(anhydride-ester) matrices using small molecule admixtures

    PubMed Central

    Ouimet, Michelle A; Snyder, Sabrina S; Uhrich, Kathryn E

    2013-01-01

    Poly(anhydride-esters) with salicylic acid, a nonsteroidal anti-inflammatory drug, chemically incorporated into the polymer backbone provide high inherent drug loading. These poly(anhydride-esters) hydrolytically degrade to release salicylic acid over extended time periods (>30 days); however, an initial lag period of no salicylic acid release is observed. This lag period could be unfavorable in applications where immediate salicylic acid release is desired. Poly(anhydride-esters) with short (2 days) and long (11 days) lag periods were admixed with various small molecules as a means to shorten or eliminate the lag period. Salicylic acid, larger salicylic acid prodrugs, and 1:1 combinations of the two were physically admixed, each at 1%, 5%, and 10% (w/w). All admixtures resulted in immediate salicylic acid release and a decrease in glass transition temperatures compared to polymer alone. By varying the amounts of salicylic acid and salicylic acid prodrugs incorporated into the polymer matrix, immediate and constant salicylic acid release profiles over varied time periods were achieved. PMID:24078768

  17. Concurrent release of admixed antimicrobials and salicylic acid from salicylate-based poly(anhydride-esters)

    PubMed Central

    Johnson, Michelle L.; Uhrich, Kathryn E.

    2008-01-01

    A polymer blend consisting of antimicrobials (chlorhexidine, clindamycin, and minocycline) physically admixed at 10% by weight into a salicylic acid-based poly (anhydride-ester) (SA-based PAE) was developed as an adjunct treatment for periodontal disease. The SA-based PAE/antimicrobial blends were characterized by multiple methods, including contact angle measurements and differential scanning calorimetry. Static contact angle measurements showed no significant differences in hydrophobicity between the polymer and antimicrobial matrix surfaces. Notable decreases in the polymer glass transition temperature (Tg) and the antimicrobials' melting points (Tm) were observed indicating that the antimicrobials act as plasticizers within the polymer matrix. In vitro drug release of salicylic acid from the polymer matrix and for each physically admixed antimicrobial was concurrently monitored by high pressure liquid chromatography during the course of polymer degradation and erosion. Although the polymer/antimicrobial blends were immiscible, the initial 24 h of drug release correlated to the erosion profiles. The SA-based PAE/antimicrobial blends are being investigated as an improvement on current localized drug therapies used to treat periodontal disease. PMID:19180627

  18. Synthesis and Characterization of Poly(maleic Anhydride)s Cross-linked Polyimide Aerogels

    NASA Technical Reports Server (NTRS)

    Guo, Haiquan; Meador, Mary Ann B.

    2015-01-01

    With the development of technology for aerospace applications, new thermal insulation materials are required to be flexible and capable of surviving high heat flux. For instance, flexible insulation is needed for inflatable aerodynamic decelerators which are used to slow spacecraft for entry, descent and landing (EDL) operations. Polyimide aerogels have low density, high porosity, high surface area, and better mechanical properties than silica aerogels and can be made into flexible thin films, thus they are potential candidates for aerospace needs. The previously reported cross-linkers such as octa(aminophenyl)silsesquioxane (OAPS) and 1,3,5-triaminophenoxybenzene (TAB) are either expensive or not commercially available. Here, we report the synthesis of a series of polyimide aerogels cross-linked using various commercially available poly(maleic anhydride)s, as seen in Figure 1. The amine end capped polyimide oligomers were made with 3,3,4,4-biphenyltetracarboxylic dianhydride (BPDA) and diamine combinations of dimethylbenzidine (DMBZ) and 4, 4-oxydianiline (ODA). The resulting aerogels have low density (0.12 gcm3 to 0.16 gcm3), high porosity (90) and high surface area (380-554 m2g). The effect of the different poly(maleic anhydride) cross-linkers and polyimide backbone structures on density, shrinkage, porosity, surface area, mechanical properties, moisture resistance and thermal properties will be discussed.

  19. Controlled delivery of paclitaxel from stent coatings using novel styrene maleic anhydride copolymer formulations.

    PubMed

    Richard, Robert; Schwarz, Marlene; Chan, Ken; Teigen, Nikolai; Boden, Mark

    2009-08-01

    The controlled release of paclitaxel (PTx) from stent coatings comprising an elastomeric polymer blended with a styrene maleic anhydride (SMA) copolymer is described. The coated stents were characterized for morphology by scanning electron microscopy (SEM) and atomic force microscopy (AFM), and for drug release using high-performance liquid chromatography (HPLC). Differential scanning calorimetry (DSC) was used to measure the extent of interaction between the PTx and polymers in the formulation. Coronary stents were coated with blends of poly(b-styrene-b-isobutylene-b-styrene) (SIBS) and SMA containing 7% or 14% maleic anhydride (MA) by weight. SEM examination of the stents showed that the coating did not crack or delaminate either before or after stent expansion. Examination of the coating surface via AFM after elution of the drug indicated that PTx resides primarily in the SMA phase and provided information about the mechanism of PTx release. The addition of SMA altered the release profile of PTx from the base elastomer coatings. In addition, the presence of the SMA enabled tunable release of PTx from the elastomeric stent coatings, while preserving mechanical properties. Thermal analysis reveled no shift in the glass transition temperatures for any of the polymers at all drug loadings studied, indicating that the PTx is not miscible with any component of the polymer blend. An in vivo evaluation indicated that biocompatibility and vascular response results for SMA/SIBS-coated stents (without PTx) are similar to results for SIBS-only-coated and bare stainless steel control stents when implanted in the non-injured coronary arteries of common swine for 30 and 90 days.

  20. Metal phthalocyanine polymers

    NASA Technical Reports Server (NTRS)

    Achar, B. N.; Fohlen, G. M.; Parker, J. A. (Inventor)

    1984-01-01

    Metal 4, 4', 4", 4"'=tetracarboxylic phthalocyanines (MPTC) are prepared by reaction of trimellitic anhydride, a salt or hydroxide of the desired metal (or the metal in powdered form), urea and a catalyst. A purer form of MPTC is prepared than heretofore. These tetracarboxylic acids are then polymerized by heat to sheet polymers which have superior heat and oxidation resistance. The metal is preferably a divalent metal having an atomic radius close to 1.35A.

  1. In vitro evaluation of the genotoxicity of poly(anhydride) nanoparticles designed for oral drug delivery.

    PubMed

    Iglesias, T; Dusinska, M; El Yamani, N; Irache, J M; Azqueta, A; López de Cerain, A

    2017-05-15

    In the last years, the development of nanomaterials has significantly increased due to the immense variety of potential applications in technological sectors, such as medicine, pharmacy and food safety. Focusing on the nanodevices for oral drug delivery, poly(anhydride) nanoparticles have received extensive attention due to their unique properties, such as their capability to develop intense adhesive interactions within the gut mucosa, their modifiable surface and their biodegradable and easy-to-produce profile. However, current knowledge of the possible adverse health effects as well as, toxicological information, is still exceedingly limited. Thus, we investigated the capacity of two poly(anhydride) nanoparticles, Gantrez(®) AN 119-NP (GN-NP) and Gantrez(®) AN 119 covered with mannosamine (GN-MA-NP), and their main bulk material (Gantrez(®) AN 119-Polymer), to induce DNA damage and thymidine kinase (TK(+/-)) mutations in L5178Y TK(+/-) mouse lymphoma cells after 24h of exposure. The results showed that GN-NP, GN-MA-NP and their polymer did not induce DNA strand breaks or oxidative damage at concentrations ranging from 7.4 to 600μg/mL. Besides, the mutagenic potential of these nanoparticles and their polymer revealed no significant or biologically relevant gene mutation induction at concentrations up to 600μg/mL under our experimental settings. Considering the non-genotoxic effects of GN-NP and GN-MA-NP, as well as their exceptional properties, these nanoparticles are promising nanocarriers for oral medical administrations. Copyright © 2017 Elsevier B.V. All rights reserved.

  2. Poly(anhydride-ester) and poly(N-vinyl-2-pyrrolidone) blends: salicylic acid-releasing blends with hydrogel-like properties that reduce inflammation.

    PubMed

    Ouimet, Michelle A; Fogaça, Renata; Snyder, Sabrina S; Sathaye, Sameer; Catalani, Luiz H; Pochan, Darrin J; Uhrich, Kathryn E

    2015-03-01

    Polymers such as poly(N-vinyl-2-pyrrolidone) (PVP) have been used to prepare hydrogels for wound dressing applications but are not inherently bioactive. For enhanced healing, PVP was blended with salicylic acid-based poly(anhydride-esters) (SAPAE) and shown to exhibit hydrogel properties upon swelling. In vitro release studies demonstrated that the chemically incorporated drug (SA) was released from the polymer blends over 3-4 d in contrast to 3 h, and that blends of higher PVP content displayed greater swelling values and faster SA release. The polymer blends significantly the inflammatory cytokine, TNF-α, in vitro without negative effects.

  3. Grafting of poly (lactic acid) with maleic anhydride using supercritical carbon dioxide

    NASA Astrophysics Data System (ADS)

    Khankrua, R.; Pivsa-Art, S.; Hiroyuki, H.; Suttiruengwong, S.

    2015-07-01

    The aim of this work was to modify poly lactic acid (PLA) via free radical grafting with maleic anhydride (MA) by using supercritical carbon dioxide (SCCO2). Benzoyl peroxide (BPO) was used as an initiator. The solubility of MA in SCCO2 was first determined to estimate the suitable grafting conditions and equilibrium. From the solubility study of MA in SCCO2, it was found that the solubility of MA in SCCO2 increased with the increasing pressure and dissolution time. PLA films were first prepared by compression molding. The ratio of MA to BPO was 2:1. The reaction temperature and pressure were 70°C and 100 bar respectively. The grafting reaction and the degree of grafting were characterized by nuclear magnetic resonance (NMR) spectroscopy and titration, respectively. Scanning electron microscope (SEM) technique and contact angle were used to confirm the changes in physical properties of PLA film grafted MA. NMR spectrum indicated that the grafting of MA onto PLA was successively achieved. Degree of grafting by using SCCO2 was as high as 0.98%. This provided rather high grafting degree compared with other processes. SEM pictures showed the rough surface structure on modified PLA film. In addition, contact angle results showed an improvement of the hydrophilicity by maleic anhydride grafting onto polymers.

  4. Interaction and release of catechin from anhydride maleic-grafted polypropylene films.

    PubMed

    López de Dicastillo, Carol; Castro-López, Maria Del Mar; Lasagabaster, Aurora; López-Vilariño, Jose M; González-Rodríguez, M Victoria

    2013-04-24

    In this paper, investigations were carried out on catechin-loaded maleic anhydride (MAH)-modified polypropylenes (PP). Two maleic-modified polypropylenes (PPMAH) with different maleic concentrations have been blended with PP and catechin to obtain composites of improved catechin retention with the aim of studying the possible interactions between these grafted polymers with antioxidants, and a secondary interest in developing an active antioxidant packaging. Composite physicochemical properties were measured by thermal analysis (thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and oxidation induction time (OIT)) and infrared spectroscopy studies. Catechin release profiles into food simulants were obtained by HPLC-PDA-QqQ, following European legislation. Antiradical activity of composites was analyzed by the ABTS and DPPH method. The formation of intermolecular hydrogen bonds between catechin and functionalized PP has been confirmed by Fourier transform infrared (FTIR) studies. Besides, a small fraction of ester bonds, formed as a result of a chemical reaction between a fraction of the hydrolyzed anhydride and the catechin hydroxyl groups, is not discarded. OIT results also showed an increase in antioxidant effectiveness caused by the presence of catechin- and maleic-modified PPMAH in the blend formulations. Incorporation of MAH-grafted PP increased substantially the retention rate of catechin, being dependent on the MAH content of the grafted polypropylene. The described interactions between catechin and maleic groups, together with changes in PP morphology in comparison with reference PP explained lower antioxidant release. Besides formulation, antioxidant release was dependent on the type of food, the temperature, and the time.

  5. Non-steroidal anti-inflammatory drug (NSAID)-derived poly(anhydride-esters) in bone and periodontal regeneration.

    PubMed

    Reynolds, Mark A; Prudencio, Almudena; Aichelmann-Reidy, Mary E; Woodward, Kevin; Uhrich, Kathryn E

    2007-07-01

    Bioresorbable polymers offer the potential to deliver biologically active agents that selectively modulate wound healing in bone and periodontal regeneration. This preliminary study characterizes early wound healing in calvarial defects grafted with demineralized bone matrix (DBM) overlaid with membranes made from a novel class of non-steroidal anti-inflammatory drug (NSAID)-derived poly(anhydride-esters). These polymers chemically incorporate either salicylic acid (SA) or 5-(2',4'-difluorophenyl)salicylic acid (diflunisal) into the polymeric backbone and release the NSAIDs upon hydrolysis. Inflammatory cell infiltrate in response to the novel NSAID-derived polymers was compared to defects grafted with DBM alone at 10 days and to defects grafted with DBM and overlaid with poly(lactic acid) (PLA; Atrisorb) at 21 days in 8 Wistar rats (350-450 g). Histological analysis of the calvarial sites at 10 days revealed that the NSAID-derived polymers were associated with moderate levels of inflammation similar to defects grafted without polymer (2.3 +/- 0.96 versus 2.0 +/- 0.82, respectively), consistent with the therapeutic activity of salicylic acid and diflunisal. Defects grafted with DBM and overlaid with NSAID-derived polymers at 21 days exhibited mild inflammation; whereas, defects treated with PLA were consistently associated with moderate to severe inflammatory cell infiltrate (1.8 +/- 0.50 versus 2.7 +/- 0.58, respectively). Histopathological findings, such as foreign body giant cells or fibrous encapsulation, were not observed in any defects with NSAID-derived polymers. Cellular features consistent with bone formation were found in all grafted defects. This novel class of non-steroidal anti-inflammatory drug-derived poly(anhydride-esters) were well tolerated and elicited no demonstrable increase in inflammation, as shown with PLA, during osseous wound healing in a regenerative application.

  6. THE RATIO OF THE GLASS TEMPERATURE TO THE MELTING POINT IN POLYMERS.

    DTIC Science & Technology

    PLASTICS , MELTING POINT, TRANSITION TEMPERATURE, POLYETHYLENE PLASTICS , VINYL PLASTICS , BUTADIENES, FLUORINE COMPOUNDS, STYRENE PLASTICS , POLYMERS...NYLON, PHYSICAL PROPERTIES, MOLECULAR STRUCTURE, CARBONATES, ESTERS, ACRYLIC RESINS, PHENOLIC PLASTICS , ANHYDRIDES, CARBOXYLIC ACIDS, PHTHALATES, UNITED KINGDOM.

  7. Quick don-doff electrode pastes

    NASA Technical Reports Server (NTRS)

    Mosier, B.

    1969-01-01

    Evaluation of electrode pastes for use in electrocardiographs and electroencephalographs found that the one having the desired don-doff properties had to be water soluble or a water dispersible base. Poly /methyl vinyl ether/maleic anhydride/ or starch gels of the gum drop variety are two such bases.

  8. Hydration of AN Acid Anhydride: the Water Complex of Acetic Sulfuric Anhydride

    NASA Astrophysics Data System (ADS)

    Smith, CJ; Huff, Anna; Mackenzie, Becca; Leopold, Ken

    2017-06-01

    The water complex of acetic sulfuric anhydride (ASA, CH_{3}COOSO_{2}OH) has been observed by pulsed nozzle Fourier transform microwave spectroscopy. ASA is formed in situ in the supersonic jet via the reaction of SO_{3} and acetic acid and subsequently forms a complex with water during the expansion. Spectra of the parent and fully deuterated form, as well as those of the species derived from CH_{3}^{13}COOH, have been observed. The fitted internal rotation barrier of the methyl group is 219.599(21), \\wn indicating the complexation with water lowers the internal rotation barrier of the methyl group by 9% relative to that of free ASA. The observed species is one of several isomers identified theoretically in which the water inserts into the intramolecular hydrogen bond of the ASA. Aspects of the intermolecular potential energy surface are discussed.

  9. Method for epoxy foam production using a liquid anhydride

    DOEpatents

    Celina, Mathias [Albuquerque, NM

    2012-06-05

    An epoxy resin mixture with at least one epoxy resin of between approximately 50 wt % and 100 wt %, an anhydride cure agent of between approximately 0 wt % and approximately 50 wt %, a tert-butoxycarbonyl anhydride foaming agent of between proximately 0.1-20 wt %, a surfactant and an imidazole or similar catalyst of less than approximately 2 wt %, where the resin mixture is formed from at least one epoxy resin with a 1-10 wt % tert-butoxycarbonyl anhydride compound and an imidazole catalyst at a temperature sufficient to keep the resin in a suitable viscosity range, the resin mixture reacting to form a foaming resin which in the presence of an epoxy curative can then be cured at a temperature greater than 50.degree. C. to form an epoxy foam.

  10. β-Functionalization of carboxylic anhydrides with β-alkyl substituents through carbene organocatalysis.

    PubMed

    Jin, Zhichao; Chen, Shaojin; Wang, Yuhuang; Zheng, Pengcheng; Yang, Song; Chi, Yonggui Robin

    2014-12-01

    The first NHC-catalyzed functionalization of carboxylic anhydrides is described. In this reaction, the β carbon behaves as a nucleophilic carbon and undergoes asymmetric reactions with electrophiles. Anhydrides with challenging β-alkyl substituents work effectively.

  11. Formulation of salicylate-based poly(anhydride-ester) microspheres for short- and long-term salicylic acid delivery

    PubMed Central

    Rosario-Meléndez, Roselin; Ouimet, Michelle A.; Uhrich, Kathryn E.

    2013-01-01

    The formulation of salicylate-based poly(anhydride-ester) (PAE) microspheres was optimized by altering polymer concentration and homogenization speed to improve the overall morphology. The microspheres were prepared using three salicylate-based PAEs with different chemical compositions comprised of either a heteroatomic, linear aliphatic, or branched aliphatic moiety. These PAEs broadened the range of complete salicylic acid release to now include days, weeks and months. The molecular weight (Mw), polydispersity index (PDI) and glass transition temperature (Tg) of the formulated polymers were compared to the unformulated polymers. In general, the Mw and PDI exhibited decreased and increased values, respectively, after formulation, whereas the Tg changes did not follow a specific trend. Microsphere size and morphology were determined using scanning electron microscopy. These microspheres exhibited smooth surfaces, no aggregation, and size distributions ranging from 2-34 m in diameter. In vitro release studies of the chemically incorporated salicylic acid displayed widely tunable release profiles. PMID:23420391

  12. Heterogeneous catalyst for the production of acetic anhydride from methyl acetate

    DOEpatents

    Ramprasad, D.; Waller, F.J.

    1999-04-06

    This invention relates to a process for producing acetic anhydride by the reaction of methyl acetate, carbon monoxide, and hydrogen at elevated temperatures and pressures in the presence of an alkyl halide and a heterogeneous, bifunctional catalyst that contains an insoluble polymer having pendant quaternized phosphine groups, some of which phosphine groups are ionically bonded to anionic Group VIII metal complexes, the remainder of the phosphine groups being bonded to iodide. In contrast to prior art processes, no accelerator (promoter) is necessary to achieve the catalytic reaction and the products are easily separated from the catalyst by filtration. The catalyst can be recycled for consecutive runs without loss in activity. Bifunctional catalysts for use in carbonylating dimethyl ether are also provided.

  13. Preparation of extruded polyethylene/chitosan blends compatibilized with polyethylene-graft-maleic anhydride.

    PubMed

    Quiroz-Castillo, J M; Rodríguez-Félix, D E; Grijalva-Monteverde, H; Del Castillo-Castro, T; Plascencia-Jatomea, M; Rodríguez-Félix, F; Herrera-Franco, P J

    2014-01-30

    Novel films of polyethylene and chitosan were obtained using extrusion. These polymers have interesting properties, and processing them with methods that are of high use in the industry, such as the extrusion method, can have a significant effect on the potential applications of these materials. The individual materials were thermally characterized; after this, extruded films of low density polyethylene and chitosan mixtures were prepared with the addition of polyethylene-graft-maleic anhydride as a compatibilizer for the blends, and glycerol, as a plasticizer for chitosan. The use of compatibilizer and plasticizer agents improved the processability and compatibility of the mixtures, as well as their mechanical properties, as revealed by mechanical property measurements and scanning electron microscopy. It was possible to prepare blends with a maximum chitosan content of 20 wt%. The material stiffness increased with the increase of chitosan in the sample. FTIR studies revealed the existence of an interaction between the compatibilizer and chitosan.

  14. Heterogeneous catalyst for the production of acetic anhydride from methyl acetate

    DOEpatents

    Ramprasad, Dorai; Waller, Francis Joseph

    1999-01-01

    This invention relates to a process for producing acetic anhydride by the reaction of methyl acetate, carbon monoxide, and hydrogen at elevated temperatures and pressures in the presence of an alkyl halide and a heterogeneous, bifunctional catalyst that contains an insoluble polymer having pendant quaternized phosphine groups, some of which phosphine groups are ionically bonded to anionic Group VIII metal complexes, the remainder of the phosphine groups being bonded to iodide. In contrast to prior art processes, no accelerator (promoter) is necessary to achieve the catalytic reaction and the products are easily separated from the catalyst by filtration. The catalyst can be recycled for consecutive runs without loss in activity. Bifunctional catalysts for use in carbonylating dimethyl ether are also provided.

  15. Preparation and Characterization of Octenyl Succinic Anhydride Modified Taro Starch Nanoparticles

    PubMed Central

    Jiang, Suisui; Dai, Lei; Qin, Yang; Xiong, Liu; Sun, Qingjie

    2016-01-01

    The polar surface and hydrophilicity of starch nanoparticles (SNPs) result in their poor dispersibility in nonpolar solvent and poor compatibility with hydrophobic polymers, which limited the application in hydrophobic system. To improve their hydrophobicity, SNPs prepared through self-assembly of short chain amylose debranched from cooked taro starch, were modified by octenyl succinic anhydride (OSA). Size via dynamic light scattering of OSA-SNPs increased compared with SNPs. Fourier transform infrared spectroscopy data indicated the OSA-SNPs had a new absorption peak at 1727 cm-1, which was the characteristic peak of carbonyl, indicating the formation of the ester bond. The dispersibility of the modified SNPs in the mixture of water with nonpolar solvent increased with increasing of degree of substitution (DS). OSA-SNPs appear to be a potential agent to stabilize the oil-water systems. PMID:26918568

  16. Preparation and Characterization of Octenyl Succinic Anhydride Modified Taro Starch Nanoparticles.

    PubMed

    Jiang, Suisui; Dai, Lei; Qin, Yang; Xiong, Liu; Sun, Qingjie

    2016-01-01

    The polar surface and hydrophilicity of starch nanoparticles (SNPs) result in their poor dispersibility in nonpolar solvent and poor compatibility with hydrophobic polymers, which limited the application in hydrophobic system. To improve their hydrophobicity, SNPs prepared through self-assembly of short chain amylose debranched from cooked taro starch, were modified by octenyl succinic anhydride (OSA). Size via dynamic light scattering of OSA-SNPs increased compared with SNPs. Fourier transform infrared spectroscopy data indicated the OSA-SNPs had a new absorption peak at 1727 cm-1, which was the characteristic peak of carbonyl, indicating the formation of the ester bond. The dispersibility of the modified SNPs in the mixture of water with nonpolar solvent increased with increasing of degree of substitution (DS). OSA-SNPs appear to be a potential agent to stabilize the oil-water systems.

  17. Nickel-catalyzed decarboxylative carboamination of alkynes with isatoic anhydrides.

    PubMed

    Yoshino, Yasufumi; Kurahashi, Takuya; Matsubara, Seijiro

    2009-06-10

    An intermolecular nickel-catalyzed addition reaction in which isatoic anhydrides react with alkynes to afford substituted quinolones has been developed. A mechanistic rationale is proposed, implying oxidative addition of Ni(0) to a carbamate, which allows intermolecular addition to alkynes via decarboxylation.

  18. Rheological studies on the reaction of zein with polyethylenemaleic anhydride

    USDA-ARS?s Scientific Manuscript database

    There continues to be interest in developing solvent-resistant articles from biobased renewable materials to successfully complete with petro-chemical products. It was previously shown that reaction of zein with polyethylenemaleic anhydride (PEMA) provides articles that are solvent-resistant. The ge...

  19. IDENTIFYING AIRWAY SENSITIZERS: MRNA CYTOKINE PROFILES INDUCED BY VARIOUS ANHYDRIDES

    EPA Science Inventory

    Abstract:
    Exposure to low molecular weight (LMW) chemicals in the workplace has been linked to a variety of respiratory effects. Within the LMW chemicals, one of the major classes involved in these effects are the acid anhydrides. The immunological basis of respiratory hyp...

  20. IDENTIFYING AIRWAY SENSITIZERS: MRNA CYTOKINE PROFILES INDUCED BY VARIOUS ANHYDRIDES

    EPA Science Inventory

    Abstract:
    Exposure to low molecular weight (LMW) chemicals in the workplace has been linked to a variety of respiratory effects. Within the LMW chemicals, one of the major classes involved in these effects are the acid anhydrides. The immunological basis of respiratory hyp...

  1. Condensation of anhydrides or dicarboxylic acids with compounds containing active methylene groups. Part 1: Condensation of phthalic anhydride with acetoacetic and malonic ester

    NASA Technical Reports Server (NTRS)

    Oshkaya, V. P.; Vanag, G. Y.

    1985-01-01

    Phthalic anhydride was condensed with acetoacetic ester in acetic anhydride and triethylamine solution, and when phthalyl chloride was reacted with sodium acetoacetic ester compounds were formed of the phthalide and indandione series: phthalylacetoacetic ester and a derivative of indan-1,3-dione which after boiling with hydrochloric acid yielded indan-1,3-dione. Phthalylmalonic ester was obtained from phthalic anhydride and malonic ester in the presence of triethylamine.

  2. Substituted isatoic anhydrides: selective inactivators of trypsin-like serine proteases.

    PubMed

    Gelb, M H; Abeles, R H

    1986-04-01

    Derivatives of isatoic anhydride were prepared and tested as inhibitors of serine proteases. A number of isatoic anhydrides with positively charged substituents irreversibly inactivated several trypsin-like enzymes and preferentially inactivated trypsin over chymotrypsin. Further selectivity was obtained by introduction of an aromatic group on the N-1 position of isatoic anhydride. 7-(Aminomethyl)-1-benzylisatoic anhydride was prepared and was a selective inactivator of thrombin; thus it is possible to prepare derivatives of isatoic anhydride that are highly enzyme selective without attaching peptide recognition structures.

  3. Tailoring polymer properties with layered silicates

    NASA Astrophysics Data System (ADS)

    Xu, Liang

    Polymer layered silicate nanocomposites have found widespread applications in areas such as plastics, oil and gas production, biomedical, automotive and information storage, but their successful commercialization critically depends on consistent control over issues such as complete dispersion of layered silicate into the host polymer and optimal interaction between the layered silicates and the polymers. Polypropylene is a commercially important polymer but usually forms intercalated structures with organically modified layered silicate upon mixing, even it is pre-treated with compatibilizing agent such as maleic anhydride. In this work, layered silicate is well dispersed in ammonium modified polypropylene but does not provide sufficient reinforcement to the host polymer due to poor interactions. On the other hand, interactions between maleic anhydride modified polypropylene and layered silicate are fine tuned by using a small amount of maleic anhydride and mechanical strength of the resultant nanocomposites are significantly enhanced. In particular, the melt rheological properties of layered silicate nanocomposites with maleic anhydride functionalized polypropylene are contrasted to those based on ammonium-terminated polypropylene. While the maleic anhydride treated polypropylene based nanocomposites exhibit solid-like linear dynamic behavior, consistent with the formation of a long-lived percolated nanoparticle network, the single-end ammonium functionalized polypropylene based nanocomposites demonstrated liquid-like behavior at comparable montmorillonite concentrations. The differences in the linear viscoelasticity are attributed to the presence of bridging interaction in maleic anhydride functionalized nanocomposites, which facilitates formation of a long-lived silicate network mediated by physisorbed polymer chains. Further, the transient shear stress of the maleic anhydride functionalized nanocomposites in start-up of steady shear is a function of the shear

  4. Cellulose-polyhydroxylated fatty acid ester-based bioplastics with tuning properties: Acylation via a mixed anhydride system.

    PubMed

    Heredia-Guerrero, José A; Goldoni, Luca; Benítez, José J; Davis, Alexander; Ceseracciu, Luca; Cingolani, Roberto; Bayer, Ilker S; Heinze, Thomas; Koschella, Andreas; Heredia, Antonio; Athanassiou, Athanassia

    2017-10-01

    The synthesis of microcrystalline cellulose (MCC) and 9,10,16-hydroxyhexadecanoic (aleuritic) acid ester-based bioplastics was investigated through acylation in a mixed anhydride (trifluoroacetic acid (TFA)/trifluoroacetic acid anhydride (TFAA)), chloroform co-solvent system. The effects of chemical interactions and the molar ratio of aleuritic acid to the anhydroglucose unit (AGU) of cellulose were investigated. The degree of substitution (DS) of new polymers were characterized by two-dimensional solution-state NMR and ranged from 0.51 to 2.60. The chemical analysis by attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR) confirmed the presence of aleuritate groups in the structure induces the formation of new H-bond networks. The tensile analysis and the contact angle measurement confirmed the ductile behavior and the hydrophobicity of the prepared bioplastics. By increasing the aleuritate amounts, the glass transition temperature decreased and the solubility of bioplastic films in most common solvents was improved. Furthermore, this new polymer exhibits similar properties compared to commercial cellulose derivatives. Copyright © 2017 Elsevier Ltd. All rights reserved.

  5. Chitosan: poly( N-vinylpyrrolidone- alt-itaconic anhydride) nanocapsules—a promising alternative for the lung cancer treatment

    NASA Astrophysics Data System (ADS)

    Raţă, Delia Mihaela; Chailan, Jean-François; Peptu, Cătălina Anişoara; Costuleanu, Marcel; Popa, Marcel

    2015-07-01

    This study reports the preparation of novel polymeric nanocapsules based on a natural polymer, chitosan and a synthetic one, poly( N-vinylpyrrolidone- alt-itaconic anhydride) [(poly(NVPAI)] using an interfacial condensation technique. The infrared spectroscopy studies confirmed the crosslinking through the presence of amide bonds, formed between the two polymers chains. The diameter of nanocapsules was found in the range of 126-214 nm and it was determined by dynamic light scattering method. Morphological characterization demonstrated their nano size, the spherical shape of the nanocapsules and the formation of hollow particles. The nanocapsules presented good swelling capacity in aqueous solutions. 5-Fluorouracil (5-FU) loading and release capacity was studied, the processes being controlled by the drug diffusion through the polymeric membrane. The obtained results were encouraging, showing that 5-FU-loaded nanocapsules had 70 % higher apoptotic effect on A549 tumour cells than the drug in free state or mixed with the nanocapsules.

  6. Relationship of airborne trimellitic anhydride concentrations to trimellitic anhydride--induced symptoms and immune responses

    SciTech Connect

    Bernstein, D.I.; Roach, D.E.; McGrath, K.G.; Larsen, R.S.; Zeiss, C.R.; Patterson, R.

    1983-12-01

    Eighteen workers exposed to trimellitic anhydride (TMA) powder were evaluated in 1979. Twelve of these workers were available for longitudinal study until 1982. Annual clinical evaluations and serum radioimmunoassays for total antibody binding and specific IgE binding to /sup 125/I-TM-HSA were performed. In 1979, five workers had antibody against TM-HSA. Of these, three workers were diagnosed with the late respiratory systemic syndrome (LRSS) and one worker with TMA-induced allergic rhinitis. The LRSS workers had significantly elevated total antibody binding of /sup 125/I-TM-HSA and the worker with rhinitis had significantly elevated specific IgE binding of /sup 125/I-TM-HSA per milliliter of serum. Although TMA handling was intermittent throughout the year, average airborne dust concentrations from 1974 to 1978 at job stations of the two heaviest TMA-exposed occupations, operator and assistant operator, were 2.1 and 0.82 mg/m3, respectively. After local exhaust ventilation had been improved, average airborne dust concentrations of TMA at the two latter job stations fell to levels of 0.03 and 0.01 mg/m3, respectively, in 1982. The decrease in TMA exposure coincided with a gradual fall in total antibody binding of /sup 125/I-TM-HSA per milliliter in 1982 and symptomatic improvement in the three individuals with the LRSS. The continuous low-level exposure of the worker with TMA rhinitis was sufficient to elicit a rise in specific IgE against TM-HSA from 1.1 ng of 125I-TM-HSA bound per milliliter in 1979 to 2.12 in 1982.

  7. Properties of polyethylene films with incorporated benzoic anhydride and/or ethyl and propyl esters of 4-hydroxybenzoic acid and their suitability for food packaging.

    PubMed

    Dobiás, J; Chudackova, K; Voldrich, M; Marek, M

    2000-12-01

    Benzoic anhydride and ethyl and propyl esters of 4-hydroxybenzoic acid (ETP and PRP, respectively, also termed parabens) incorporated into low density polyethylene (LDPE) film were studied with regard to migration into food and food simulants at 6 degrees C and 25 degrees C, and changes in selected properties of the film were investigated. Antimicrobials were incorporated into polymer film in concentrations of 5 g/kg and 10 g/kg. The addition of parabens into the polymer was more difficult than benzoic anhydride due to their volatility. For benzoic anhydride, 30-40% and 10-20% of the added amount was found to leach from the film into aqueous and olive oil food simulants, respectively. The migration into both water and olive oil followed a very similar course in the case of parabens. Migration levels over 90% and in the range of 70% to 80%, relative to the amount of agent in the film, were determined for ETP and PRP respectively. The incorporation of antimicrobials into the film significantly changed the functional characteristics of the packaging material, i.e. permeability of oxygen, carbon dioxide and water vapour, tensile strength, coefficient of friction, sealing strength and transparency. Shelf life tests with packaged cheese and toasted bread demonstrated the efficiency of the film containing 10 g/kg of BA against mould growth on the food surface during storage at 6 degrees C.

  8. Particleboard made from waste paper treated with maleic anhydride.

    PubMed

    Nourbakhsh, Amir; Ashori, Alireza

    2010-01-01

    This study evaluates the usage of waste newspaper as a supplement raw material for laboratory-made single-layer particle-boards. The boards were made of various ratios (75/25, 50/50, 25/75 and 0/100) of waste paper flakes to wood particles mixtures (wt/wt). The effects of press temperature and maleic anhydride on the properties of the boards were determined. Evaluated properties were modulus of rupture, modulus of elasticity, internal bonding strength, and thickness swelling. Panels made from waste newspaper satisfied the modulus of rupture, modulus of elasticity and internal bonding strength requirements of European Norms standards. Performing a statistical analysis of the results, press temperature and maleic anhydride content were found to be positively effective on the mechanical properties at a 95% confidence level. The results from this study indicated that technically waste paper could be a potential substitute material for particleboard manufacture.

  9. Design of cycloolefin-maleic-anhydride resist for ArF lithography

    NASA Astrophysics Data System (ADS)

    Jung, Jae Chang; Bok, Cheol-Kyu; Baik, Ki-Ho

    1998-06-01

    Recently reported ArF positive photoresists can be classified into three groups: derivative methacrylate copolymers (methacrylate resist), methacrylate copolymers functionalized with pendant alicyclic moieties (alicyclic resist), and cycloolefin-maleic anhydride copolymers (cycloolefin resist). Each system has its own advantages and drawbacks from the viewpoint of lithographic properties. Methacrylate resist has been used for the assessment of ArF lens performance. However, it is hard to apply them in real device process because of its low plasma-etch resistance. Previous studies have reported that alicyclic resists possess adequate etch resistance with the help of cyclic carbon units, however these resists show poor adhesion and seldom dissolve in 2.38% TMAH developer. The cycloolefin resists will be good candidate for addressing the trade-off between etch resistance and requisite material properties for lithographic performance because these resists, unlike methacrylate-based resists, contain large quantities of alicyclic structures directly in the polymer backbone and such properties as dissolution, adhesion can be readily controlled by incorporation of -COOH and -OH functional groups into cycloolefin structures. We have synthesized poly(2-hydroxylethyl 5-norbornene-2-carboxylate/t-butyl 5- norbornene-2-carboxylate/5-norbornene-2-carboxylic acid/maleic anhydride; HNC/BNC/NC/MA) resists with a variety of functional groups and obtained lithographic performance using ArF stepper (0.6 NA). In this paper, we will describe the basic idea for designing of the novel olefin resist and demonstrate lithographic capabilities, especially in terms of process window for 130 nm feature. We believe that both off-axis illumination and bottom anti-reflective technologies should be applied in order to obtain wider process window.

  10. Experimental and Computational Thermochemistry of 3- and 4-Nitrophthalic Anhydride.

    PubMed

    García-Castro, Miguel Ángel; Amador, Patricia; Hernández-Pérez, Julio Manuel; Medina-Favela, Adrián Eduardo; Flores, Henoc

    2014-05-08

    In order to understand the influence that the position of the nitro group on the aromatic ring has on the relative stability of two isomers, the standard enthalpies of formation of 3- and 4-nitrophthalic anhydride in the gaseous phase, at T = 298.15 K, were obtained by experimental thermochemistry and theoretical studies. The standard enthalpies of formation in the crystalline phase, at T = 298.15 K, were obtained by combustion calorimetry and the enthalpies of sublimation by the Knudsen method. For the theoretical calculations, a standard ab initio molecular orbital method at the G3 level was used. The enthalpies of formation in the gaseous phase were obtained from atomization and isodesmic reactions. A theoretical study of the molecular and electronic structures of these compounds was also performed. Differences of -9.7 kJ•mol-1, for 3-nitrophthalic anhydride, and -2.6 kJ•mol-1 for 4-nitrophthalic anhydride, were found from a comparison between our theoretical and experimental results.

  11. Delayed and immediate allergy caused by methylhexahydrophthalic anhydride.

    PubMed

    Kanerva, L; Hyry, H; Jolanki, R; Hytönen, M; Estlander, T

    1997-01-01

    Epoxy resin compounds (ERC) include a large number of chemicals, such as epoxy resins (ER), reactive diluents and hardeners. Many hardeners, e.g., aliphatic polyamines, are well-known sensitizers. Another type of ER hardeners are the phthalic anhydrides, such as methylhexahydrophthalic anhydride (MHHPA) and methyltetrahydrophthalic anhydride (MTHPA), which have been reported as causing immunologically-mediated respiratory diseases and contact urticaria, but not allergic contact dermatitis. Here, we present a horizontal boring-machine worker who developed allergic contact dermatitis, as well as allergic rhinitis and an immediate contact skin reaction from MHHPA. Patch testing with a dilution series of MHHPA in pet. elicited the following results: 2%, 1% and 0.5%, +2; 0.25% and 0.125%, + (3- to 6-day readings). An immunohistochemical and electron microscopic study also indicated that the patch test reactions were conventional-delayed allergic reactions. Interleukin 8 was observed in the epidermal cells, whereas interleukin 4 immunoreactivity was detected in the dermal cells. Immunoreactivity to-interleukin 5, granulocyte/macrophage-colophony stimulating factor (GM-CSF) or eosinophil cationic protein was not seen. In conclusion, the patient developed both Type I and Type IV allergy to MHHPA. The clinical data, patch test results, immunohistochemical and electron microscopic observations indicated that the MHHPA allergy detected by the patch test reaction was a conventional delayed-type hypersensitivity reaction. The patient also had an allergic patch test reaction to para-phenylenediamine and diaminodiphenylmethane, possibly representing occupational sensitization.

  12. Soy protein polymers: Enhancing the water stability property

    NASA Astrophysics Data System (ADS)

    Srinivasan, Gowrishankar

    Soy protein based plastics have been processed in the past by researchers for various short-term applications; however a common issue is the high water sensitivity of these plastics. This work concentrates on resolving this water sensitivity issue of soy protein polymers by employing chemical and mechanical interaction at the molecular level during extrusion. The primary chemical interactions employed were anhydride chemistries such as maleic anhydride (MA), phthalic anhydride (PTA), and butylated hydroxyanisole (BHA). These were respectively used in conjunction with glycerol as a plasticizer to produce relatively water stable soy protein based plastics. Formulations with varying additive levels of the chemistries were extruded and injection molded to form the samples for characterization. The additive levels of anhydrides were varied between 3-10% tw/tw (total mass). Results indicated that phthalic anhydride formulations resulted in highest water stability. Plastic formulations with concentration up to 10% phthalic anhydride were observed to have water absorption as low as 21.5% after 24 hrs of exposure to water with respect to 250% for the control formulation. Fourier transform infrared spectroscopy (FTIR) was utilized to characterize and confirm the fundamental mechanisms of water stability achieved by phthalic and maleic anhydride chemistries. In addition, the anhydride formulations were modified by inclusion of cotton fibers and pretreated cotton powder in order to improve mechanical properties. The incorporation of cotton fibers improved the dry strength by 18%, but did not significantly improve the wet state strength of the plastics. It was also observed that the butylated-hydroxy anisole (BHA) formulation exhibited high extension values in the dry state and had inferior water absorption properties in comparison with anhydride formulations.

  13. Linear, Mannitol-Based Poly(anhydride-esters) with High Ibuprofen Loading and Anti-Inflammatory Activity.

    PubMed

    Stebbins, Nicholas D; Yu, Weiling; Uhrich, Kathryn E

    2015-11-09

    Sugar alcohols, such as mannitol and xylitol, are biocompatible polyols that have been used to make highly cross-linked polyester elastomers and dendrimers for tissue engineering and drug delivery. However, research that utilizes the secondary hydroxyl groups as sites for pendant bioactive attachment and subsequent polymerization is limited. This work is the first report of a linear, completely biodegradable polymer with a sugar alcohol backbone and chemically incorporated pendant bioactives that exhibits sustained bioactive release and high bioactive loading (∼70%). With four pendant esters per repeat unit, this poly(anhydride-ester) has high loading and biodegrades into three biocompatible products: bioactive, sugar alcohol, and alkyl-based diacid. Ibuprofen serves as a representative bioactive, whereas mannitol is a representative polyol. Polymerization was achieved through reaction with (trimethylsilyl)ethoxyacetylene. Drug release via polymer degradation was quantified by high performance liquid chromatography. Additionally, a cytocompatibility study with fibroblast cells was performed to elucidate the polymer's suitability for in vivo use and a cyclooxygenase-2 (COX-2) assay was performed on the degradation media to ensure that released ibuprofen retained its anti-inflammatory activity. This work enables the future development of novel, biodegradable polymers exhibiting two key features: (i) polymer backbones with easily modified pendant groups, such as targeting moieties, and (ii) high drug loading using a multitude of bioactive classes.

  14. Electron paramagnetic resonance study of radiation-induced paramagnetic centers in succinic anhydride single crystal

    NASA Astrophysics Data System (ADS)

    Caliskan, Betul; Caliskan, Ali Cengiz; Er, Emine

    2017-09-01

    Succinic anhydride single crystals were exposed to 60Co-gamma irradiation at room temperature. The irradiated single crystals were investigated at 125 K by Electron Paramagnetic Resonance (EPR) Spectroscopy. The investigation of EPR spectra of irradiated single crystals of succinic anhydride showed the presence of two succinic anhydride anion radicals. The anion radicals observed in gamma-irradiated succinic anhydride single crystal were created by the scission of the carbon-oxygen double bond. The structure of EPR spectra demonstrated that the hyperfine splittings arise from the same radical species. The reduction of succinic anhydride was identified which is formed by the addition of an electron to oxygen of the Csbnd O bond. The g values, the hyperfine structure constants and direction cosines of the radiation damage centers observed in succinic anhydride single crystal were obtained.

  15. Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation.

    PubMed

    Matos, M Agostinha R; Miranda, Margarida S; Morais, Victor M; Liebman, Joel F

    2003-07-21

    This paper reports the results of our thermochemical/calorimetric determination of the enthalpies of combustion, phase change, and formation of isatin, isatoic anhydride, and N-methylisatin. The density functional calculations accompanied by vibrational and thermal corrections were also performed for these compounds and N-methylisatoic anhydride. Through a combination of theoretical calculations and associated isodesmic reactions, we have deduced that isatin has some antiaromatic character and isatoic anhydride enjoys some aromatic stabilization.

  16. Chain-length-dependent autocatalytic hydrolysis of fatty acid anhydrides in polyethylene glycol.

    PubMed

    Cao, Cao; Wang, Qing-Biao; Tang, Lin-Jun; Ge, Bing-Qiang; Chen, Zhong-Xiu; Deng, Shao-Ping

    2014-03-27

    Autocatalytic hydrolysis of fatty acid anhydrides induced by the spontaneously formed vesicles has been studied for years. However, whether the reaction autocatalyzed by vesicles formed in diluted solutions applies also to macromolecular crowded conditions remains unknown. The aim of this study is to characterize hydrolysis behavior of fatty acid anhydrides and formation of vesicles in crowded media. Inert macromolecular crowding agents such as polyethylene glycol (PEG) and Dextran were used to probe the impact of external crowding on the autocatalytic hydrolysis of fatty acid anhydrides with varied hydrophobic chain length. Under stringent conditions of crowding, hydrolysis rates of octanoic anhydride, nonanoic anhydride, and decanoic anhydride were found to decrease, but the rates of lauric anhydride and oleic anhydride increased. These results suggest that the effect of the crowding agent on the hydrolysis of fatty acid anhydrides was chain-length-dependent. Characterization of the size and polydispersity of vesicles formed from hydrolyzed fatty acid anhydrides in crowding revealed that long-chain fatty acids formed monodisperse vesicles easier at lower concentrations of PEG. Measurement of the critical aggregation concentration of ionized fatty acid in the presence of PEG showed that crowding media promoted vesicle formation from long-chain fatty acids but inhibited those from fatty acids with fewer carbon atoms. Further investigation of the diffusion property of ionized fatty acids in crowding agents suggested that PEG might create more hydrophobic areas for long-chain fatty acids anhydrides, which subsequently promoted the unreacted anhydride in the aqueous phase to be solubilized in the formed vesicles. This research provides information for understanding the autocatalytic reaction accompanied by self-producing aggregates and the behavior of fatty acids in crowding media.

  17. Synthesis and characterization of CdS nanoparticle based multiwall carbon nanotube-maleic anhydride-1-octene nanocomposites

    NASA Astrophysics Data System (ADS)

    Malikov, E. Y.; Altay, M. C.; Muradov, M. B.; Akperov, O. H.; Eyvazova, G. M.; Puskás, R.; Madarász, D.; Kukovecz, Á.; Kónya, Z.

    2015-05-01

    CdS nanoparticles were synthesized by sonication from cadmium chloride and thiourea using a multiwall carbon nanotube (MWCNT)-maleic anhydride (MA)-1-octene system as the matrix. The matrix was obtained by the "grafting from" approach from oxidized carbon nanotubes and maleic anhydride-1-octene. Multiwall carbon nanotubes used for reinforcing the matrix were synthesized by Catalytic Chemical Vapor Deposition using Fe-Co/Al2O3 as the catalyst. The obtained nanostructures were characterized by FTIR, XRD, Raman spectroscopy, TEM, SEM and UV-vis spectroscopy. The average CdS particle diameter was 7.9 nm as confirmed independently by TEM and XRD. UV-vis spectroscopy revealed that the obtained nanostructure is an appropriate base material for making optical devices. The novelty of this work is the use of the MWCNT-MA-1-octene matrix obtained via the "grafting from" approach for the synthesis of uniformly dispersed CdS nanocrystals by ultrasonic cavitation to obtain a polymer nanocomposite.

  18. The properties of poly(lactic acid)/starch blends with a functionalized plant oil: tung oil anhydride.

    PubMed

    Xiong, Zhu; Li, Chao; Ma, Songqi; Feng, Jianxian; Yang, Yong; Zhang, Ruoyu; Zhu, Jin

    2013-06-05

    Bio-sourced polymers, polylactide (PLA) and starch, have been melt-blended by lab-scale co-extruder with tung oil anhydride (TOA) as the plasticizer. The ready reaction between the maleic anhydride on TOA and the hydroxyl on starch led TOA molecules to accumulate on starch and increased the compatibility of PLA/starch blends, which was confirmed by FT-IR analyses and SEM. The TOA could change the mechanical properties and physical behaviors of PLA/starch blends. DSC and DMA analysis show that the TOA layer on starch has an effect on the thermal behavior of PLA in the ternary blend. The enrichment of TOA on starch improves the toughness and impact strength of the PLA/starch blends. The adding amount of TOA in PLA/starch blends primarily determined the compatibility and mechanical properties of the resulted ternary blends. The tensile and impact fracture modes of the PLA/starch blend with or without TOA has also been investigated by SEM analysis.

  19. Tall oil fatty acid anhydrides as corrosion inhibitor intermediates

    SciTech Connect

    Fischer, E.R.; Parker, J.E. III

    1995-12-01

    Electrochemical corrosion of carbon steel tubulars in producing oil wells causes lost production and necessitates costly repairs. Corrosive environments exists where hydrocarbons and an aqueous phase are being extracted from producing wells. Tubing life has been extended four fold with the development of organic corrosion inhibitors and concentric configuration treatment. Anhydrides derived from tall oil fatty acids offer enhanced corrosion inhibition properties as compared to traditional dimer/trimer acids. The chemistry of this intermediate and its use in corrosion inhibition for down hole applications, as well as the synthesis of novel oil and water-soluble derivatives will be discussed.

  20. Separator Membrane from Crosslinked Poly(Vinyl Alcohol) and Poly(Methyl Vinyl Ether-alt-Maleic Anhydride)

    PubMed Central

    Rohatgi, Charu Vashisth; Dutta, Naba K.; Choudhury, Namita Roy

    2015-01-01

    In this work, we report separator membranes from crosslinking of two polymers, such as poly vinyl alcohol (PVA) with an ionic polymer poly(methyl vinyl ether-alt-maleic anhydride) (PMVE-MA). Such interpolymer-networked systems were extensively used for biomedical and desalination applications but they were not examined for their potential use as membranes or separators for batteries. Therefore, the chemical interactions between these two polymers and the influence of such crosslinking on physicochemical properties of the membrane are systematically investigated through rheology and by critical gel point study. The hydrogen bonding and the chemical interaction between PMVE-MA and PVA resulted in highly cross-linked membranes. Effect of the molecular weight of PVA on the membrane properties was also examined. The developed membranes were extensively characterized by studying their physicochemical properties (water uptake, swelling ratio, and conductivity), thermal and electrochemical properties using differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA), thermo-gravimetric analysis (TGA) and electrochemical impedance spectroscopy (EIS). The DSC study shows the presence of a single Tg in the membranes indicating compatibility of the two polymers in flexible and transparent films. The membranes show good stability and ion conductivity suitable for separator applications. PMID:28347019

  1. 40 CFR 180.960 - Polymers; exemptions from the requirement of a tolerance.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...)-, polymer with ethenol and ethenyl acetate, sodium salt, minimum number average molecular weight (in amu...-84-0 Polyvinyl acetate, copolymer with maleic anhydride, partially hydrolyzed, sodium salt, minimum...-1-sulfonic acid sodium salt, polymer with ethenol and ethenyl acetate, number average molecular...

  2. Synthesis and hydrolysis behaviour of poly(ester anhydrides) from polylactone precursors containing alkenyl moieties.

    PubMed

    Korhonen, Harri; Hakala, Risto A; Helminen, Antti O; Seppälä, Jukka V

    2006-07-14

    Hydroxyl-group functional polylactones were prepared and converted to acid- terminated polyesters in a reaction with a series of alkenylsuccinic anhydrides containing 8, 12, or 18 carbons in their alkenyl chains. These polyester precursors were then linked into higher molecular weight poly(ester anhydrides) containing alkenyl moieties in their polyester blocks. The hydrolysis behaviour of the poly(ester anhydrides) was found to depend on the thermal properties of the polyester precursors. For poly(ester anhydrides) prepared from low molecular weight prepolymers with thermal transitions below 37 degrees C, the presence of hydrophobic alkenyl chains in the polyester precursors slowed the rate of weight loss. Poly(ester anhydrides) prepared from higher molecular weight prepolymers showed the opposite weight-loss behaviour; i.e., the crystallinity and thermal transitions of the alkenyl chain-containing poly(ester anhydrides) were low, and the weight loss was faster than for poly(ester anhydrides) without the alkenyl chains. The differences in length of the alkenyl chain, as such, had little effect on the hydrolysis behaviour and thermal properties of the poly(ester anhydrides).

  3. Palladium-catalyzed carbonylation of o-iodoanilines for synthesis of isatoic anhydrides.

    PubMed

    Gao, Sha; Chen, Ming; Zhao, Mi-Na; Du, Wei; Ren, Zhi-Hui; Wang, Yao-Yu; Guan, Zheng-Hui

    2014-05-02

    A novel palladium-catalyzed oxidative double carbonylation of o-iodoanilines for the synthesis of isatoic anhydrides has been developed. The reaction employs readily available o-iodoanilines as the starting materials and proceeds under mild conditions. For extension, palladium-catalyzed oxidative carbonylation of anthranilic acids was developed for the synthesis of substituted isatoic anhydrides in high to excellent yields.

  4. Initiation precursors and initiators in laser-induced copolymerization of styrene and maleic anhydride in acetone

    NASA Technical Reports Server (NTRS)

    Miner, Gilda A.; Meador, Willard E.; Chang, C. Ken

    1990-01-01

    The initiation step of photopolymerized styrene/maleic anhydride copolymer was investigated at 365 nm. UV absorption measurements provide decisive evidence that the styrene/maleic anhydride charge transfer complex is the sole absorbing species; however, key laser experiments suggest intermediate reactions lead to a monoradical initiating species. A mechanism for the photoinitiation step of the copolymer is proposed.

  5. TRIMELLITIC ANHYDRIDE-INDUCED EOSINOPHILIA IN A MURINE MODEL OF OCCUPATIONAL ASTHMA

    EPA Science Inventory

    TRIMELLITIC ANHYDRIDE-INDUCED EOSINOPHILIA IN A MURINE MODEL OF OCCUPATIONAL ASTHMA. J F Regal, ME Mohrman, E Boykin and D Sailstad. Dept. of Pharmacology, University of Minnesota, Duluth, MN, USA and NHEERL, ORD, US EPA, RTP, NC, USA.
    Trimellitic anhydride (TMA) is a small m...

  6. MALEIC ANHYDRIDE HYDROGENATION OF PD/AL2O3 CATALYST UNDER SUPERCRITICAL CO2 MEDIUM

    EPA Science Inventory

    Hydrogenation of maleic anhydride (MA) to either y-butyrolactone of succinic anhydride over simple Pd/Al2O3 impregnated catalyst in supercritical CO2 medium has been studied at different temperatures and pressures. A comparison of the supercritical CO2 medium reaction with the c...

  7. 40 CFR 721.9270 - Reaction product of epoxy with anhydride and glycerol and glycol.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Reaction product of epoxy with... Significant New Uses for Specific Chemical Substances § 721.9270 Reaction product of epoxy with anhydride and... substance identified generically as reaction product of epoxy with anhydride and glycerol and glycol (PMN...

  8. 40 CFR 721.9270 - Reaction product of epoxy with anhydride and glycerol and glycol.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Reaction product of epoxy with... Significant New Uses for Specific Chemical Substances § 721.9270 Reaction product of epoxy with anhydride and... substance identified generically as reaction product of epoxy with anhydride and glycerol and glycol (PMN...

  9. 40 CFR 721.9270 - Reaction product of epoxy with anhydride and glycerol and glycol.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Reaction product of epoxy with... Significant New Uses for Specific Chemical Substances § 721.9270 Reaction product of epoxy with anhydride and... substance identified generically as reaction product of epoxy with anhydride and glycerol and glycol (PMN...

  10. 40 CFR 721.9270 - Reaction product of epoxy with anhydride and glycerol and glycol.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Reaction product of epoxy with... Significant New Uses for Specific Chemical Substances § 721.9270 Reaction product of epoxy with anhydride and... substance identified generically as reaction product of epoxy with anhydride and glycerol and glycol (PMN...

  11. 40 CFR 721.9270 - Reaction product of epoxy with anhydride and glycerol and glycol.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Reaction product of epoxy with... Significant New Uses for Specific Chemical Substances § 721.9270 Reaction product of epoxy with anhydride and... substance identified generically as reaction product of epoxy with anhydride and glycerol and glycol (PMN...

  12. TRIMELLITIC ANHYDRIDE-INDUCED EOSINOPHILIA IN A MURINE MODEL OF OCCUPATIONAL ASTHMA

    EPA Science Inventory

    TRIMELLITIC ANHYDRIDE-INDUCED EOSINOPHILIA IN A MURINE MODEL OF OCCUPATIONAL ASTHMA. J F Regal, ME Mohrman, E Boykin and D Sailstad. Dept. of Pharmacology, University of Minnesota, Duluth, MN, USA and NHEERL, ORD, US EPA, RTP, NC, USA.
    Trimellitic anhydride (TMA) is a small m...

  13. Influence of boric anhydride upon the physical and chemical properties of ferrosilicon slag

    NASA Astrophysics Data System (ADS)

    Yefimets, A. M.; Tesleva, E. P.; Solovyan, A. V.

    2015-09-01

    The authors study the influence of boric anhydride upon the physical and chemical properties of slag in the manufacture of ferrosilicon. It is established that adding boric anhydride to the slag changes its refractory quality and its viscosity and eases pouring slag and metal. Slags with optimal composition and properties are described.

  14. Properties of styrene-maleic anhydride copolymers containing wood-based fillers

    Treesearch

    John Simonsen; Rodney Jacobson; Roger Rowell

    1998-01-01

    Recycled newsprint (ONP) and dry process aspen fiber were combined with styrene maleic anhydride (SMA) copolymers containing either 7 or 14 percent maleic anhydride. The fiber-filled SMA composites were equivalent or superior to unfilled SMA in strength, stiffness, and notched Izod impact strength. ONP performed surprisingly well as a filler. Unnotched Izod impact...

  15. Poly(anhydride-ester) and Poly(N-vinyl-2-pyrrolidone) Blends: Salicylic acid-releasing blends with hydrogel-like properties that reduce inflammation

    PubMed Central

    Ouimet, Michelle A.; Fogaça, Renata; Snyder, Sabrina S.; Sathaye, Sameer; Catalani, Luiz H.; Pochan, Darrin J.

    2015-01-01

    Polymers such as poly(N-vinyl-2-pyrrolidone) (PVP) have been used to prepare hydrogels for wound dressing applications but are not inherently bioactive. For enhanced healing, the release of physically admixed therapeutics from hydrogels has been evaluated, but with limited control over drug release profiles. To overcome these limitations, PVP was blended with salicylic acid-based poly(anhydride-esters) (SAPAE) and shown to exhibit hydrogel properties upon swelling. In vitro release studies demonstrated that the chemically incorporated drug (SA) was released from the polymer blends over 3–4 days in contrast to 3 hours, as observed with diffusion-controlled hydrogels. Generally, blends of higher PVP content displayed greater swelling values and faster SA release. The polymer blends significantly reduce the inflammatory cytokine, TNF-α, in vitro without cytotoxic or anti-proliferative effects, further demonstrating their potential as a wound dressing with enhanced healing and decreased scar tissue formation. PMID:25333420

  16. Indirect rapid prototyping of antibacterial acid anhydride copolymer microneedles.

    PubMed

    Boehm, Ryan D; Miller, Philip R; Singh, Ritika; Shah, Akash; Stafslien, Shane; Daniels, Justin; Narayan, Roger J

    2012-03-01

    Microneedles are needle-like projections with microscale features that may be used for transdermal delivery of a variety of pharmacologic agents, including antibacterial agents. In the study described in this paper, an indirect rapid prototyping approach involving a combination of visible light dynamic mask micro-stereolithography and micromolding was used to prepare microneedle arrays out of a biodegradable acid anhydride copolymer, Gantrez(®) AN 169 BF. Fourier transform infrared spectroscopy, energy dispersive x-ray spectrometry and nanoindentation studies were performed to evaluate the chemical and mechanical properties of the Gantrez(®) AN 169 BF material. Agar plating studies were used to evaluate the in vitro antimicrobial performance of these arrays against Bacillus subtilis, Candida albicans, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus. Large zones of growth inhibition were noted for Escherichia coli, S. aureus, Enterococcus faecalis and B. subtilis. The performance of Gantrez(®) AN 169 BF against several bacteria suggests that biodegradable acid anhydride copolymer microneedle arrays prepared using visible light dynamic mask micro-stereolithography micromolding may be useful for treating a variety of skin infections.

  17. The energetics of isomeric benzoxazine diones: isatoic anhydride revisited.

    PubMed

    Matos, M Agostinha R; Miranda, Margarida S; Morais, Victor M F; Liebman, Joel F

    2004-06-07

    The standard (p(o) = 0.1 MPa) molar enthalpy of formation of crystalline 2H-1,3-benzoxazine-2,4(3H)dione was measured, at T= 298.15 K, by static bomb calorimetry and the standard molar enthalpy of sublimation, at T= 298.15 K, was obtained using Calvet microcalorimetry. These values were used to derive the standard molar enthalpy of formation in the gaseous phase, T= 298.15 K, of -(401.0 +/- 3.5) kJ mol(-1). The standard molar enthalpy of sublimation of isatoic anhydride was recalculated, and our recommended experimental value for the standard molar enthalpy of formation in the gaseous phase, T= 298.15 K, is -(406.2 +/- 3.4) kJ mol(-1). Density functional calculations for the two isomers 2H-1,3-benzoxazine-2,4(3H)dione and isatoic anhydride, in which the ring nitrogen and oxygen have been transposed, confirm the experimental evidence of nearly identical thermochemical stability for these isomers.

  18. Reactive blending of thermoplastic starch and polyethylene-graft-maleic anhydride with chitosan as compatibilizer.

    PubMed

    Jantanasakulwong, Kittisak; Leksawasdi, Noppol; Seesuriyachan, Phisit; Wongsuriyasak, Somchai; Techapun, Charin; Ougizawa, Toshiaki

    2016-11-20

    Cassava starch was melt-blended with glycerol (70/30wt%/wt%) at 140°C to prepare thermoplastic starch (TPS). Chitosan (CTS) was premixed with starch and glycerol, in acidified water (lactic acid 2wt%), at 1, 5 and 10wt%/wt%. TPS/CTS was then melt-blended (160°C) with polyethylene-graft-maleic anhydride (PE-MAH). Phase determination and scanning electron microscopy indicated TPS/PE-MAH/CTS had a co-continuous morphology and CTS-induced phase inversion to give dispersed PE-MAH particles in a TPS matrix. Tensile strength at break and elongation, melt viscosity, fracture toughness and water contact angle of TPS/PE-MAH were improved by CTS incorporation. TPS/PE-MAH/CTS blends decreased the melting temperature of TPS and PE-MAH compared to the neat polymers. FTIR confirmed a reaction had occurred between amino groups (NH2) of CTS and the MAH groups of PE-MAH. This reaction and the enhanced miscibility between TPS and CTS improved the mechanical properties of the TPS/PE-MAH/CTS blend, particularly at 5wt%/wt% CTS. Copyright © 2016 Elsevier Ltd. All rights reserved.

  19. Dinuclear Zinc Salen Catalysts for the Ring Opening Copolymerization of Epoxides and Carbon Dioxide or Anhydrides.

    PubMed

    Thevenon, Arnaud; Garden, Jennifer A; White, Andrew J P; Williams, Charlotte K

    2015-12-21

    A series of four dizinc complexes coordinated by salen or salan ligands, derived from ortho-vanillin and bearing (±)-trans-1,2-diaminocyclohexane (L1) or 2,2-dimethyl-1,3-propanediamine (L2) backbones, is reported. The complexes are characterized using a combination of X-ray crystallography, multinuclear NMR, DOSY, and MALDI-TOF spectroscopies, and elemental analysis. The stability of the dinuclear complexes depends on the ligand structure, with the most stable complexes having imine substituents. The complexes are tested as catalysts for the ring-opening copolymerization (ROCOP) of CO2/cyclohexene oxide (CHO) and phthalic anhydride (PA)/CHO. All complexes are active, and the structure/activity relationships reveal that the complex having both L2 and imine substituents displays the highest activity. In the ROCOP of CO2/CHO its activity is equivalent to other metal salen catalysts (TOF = 44 h(-1) at a catalyst loading of 0.1 mol %, 30 bar of CO2, and 80 °C), while for the ROCOP of PA/CHO, its activity is slightly higher than other metal salen catalysts (TOF = 198 h(-1) at a catalyst loading of 1 mol % and 100 °C). Poly(ester-block-carbonate) polymers are also afforded using the most active catalyst by the one-pot terpolymerization of PA/CHO/CO2.

  20. Locally delivered salicylic acid from a poly(anhydride-ester): impact on diabetic bone regeneration.

    PubMed

    Wada, Keisuke; Yu, Weiling; Elazizi, Mohamad; Barakat, Sandrine; Ouimet, Michelle A; Rosario-Meléndez, Roselin; Fiorellini, Joseph P; Graves, Dana T; Uhrich, Kathryn E

    2013-10-10

    Diabetes mellitus (DM) involves metabolic changes that can impair bone repair, including a prolonged inflammatory response. A salicylic acid-based poly(anhydride-ester) (SA-PAE) provides controlled and sustained release of salicylic acid (SA) that locally resolves inflammation. This study investigates the effect of polymer-controlled SA release on bone regeneration in diabetic rats where enhanced inflammation is expected. Fifty-six Sprague-Dawley rats were randomly assigned to two groups: diabetic group induced by streptozotocin (STZ) injection or normoglycemic controls injected with citrate buffer alone. Three weeks after hyperglycemia development or vehicle injection, 5mm critical sized defects were created at the rat mandibular angle and treated with SA-PAE/bone graft mixture or bone graft alone. Rats were euthanized 4 and 12weeks after surgery, then bone fill percentage in the defect region was assessed by micro-computed tomography (CT) and histomorphometry. It was observed that bone fill increased significantly at 4 and 12weeks in SA-PAE/bone graft-treated diabetic rats compared to diabetic rats receiving bone graft alone. Accelerated bone formation in normoglycemic rats caused by SA-PAE/bone graft treatment was observed at 4weeks but not at 12weeks. This study shows that treatment with SA-PAE enhances bone regeneration in diabetic rats and accelerates bone regeneration in normoglycemic animals.

  1. Locally Delivered Salicylic Acid from a Poly(anhydride-ester): Impact on Diabetic Bone Regeneration

    PubMed Central

    Wada, Keisuke; Yu, Weiling; Elazizi, Mohamad; Barakat, Sandrine; Ouimet, Michelle A.; Rosario-Meléndez, Roselin; Fiorellini, Joseph P.; Graves, Dana T.; Uhrich, Kathryn E.

    2013-01-01

    Diabetes mellitus (DM) involves metabolic changes that can impair bone repair, including a prolonged inflammatory response. A salicylic acid-based poly(anhydride-ester) (SA-PAE) provides controlled and sustained release of salicylic acid (SA) that locally resolves inflammation. This study investigates the effect of polymer-controlled SA release on bone regeneration in diabetic rats where enhanced inflammation is expected. Fifty-six Sprague-Dawley rats were randomly assigned to two groups: diabetic group induced by streptozotocin (STZ) injection or normoglycemic controls injected with citrate buffer alone. Three weeks after hyperglycemia development or vehicle injection, 5 mm critical sized defects were created at the rat mandibular angle and treated with SA-PAE/bone graft mixture or bone graft alone. Rats were euthanized 4 and 12 weeks after surgery, then bone fill percentage in the defect region was assessed by micro-computed tomography (CT) and histomorphometry. It was observed that bone fill increased significantly at 4 and 12 weeks in SA-PAE/bone graft-treated diabetic rats compared to diabetic rats receiving bone graft alone. Accelerated bone formation in normoglycemic rats caused by SA-PAE/bone graft treatment was observed at 4 weeks but not at 12 weeks. This study shows that treatment with SA-PAE enhances bone regeneration in diabetic rats and accelerates bone regeneration in normoglycemic animals. PMID:23827476

  2. Oral delivery of insulin loaded poly(fumaric-co-sebacic) anhydride microspheres.

    PubMed

    Furtado, Stacia; Abramson, Danielle; Burrill, Roxanne; Olivier, Gloria; Gourd, Celinda; Bubbers, Emily; Mathiowitz, Edith

    2008-01-22

    The bioadhesive polymer, poly(fumaric-co-sebacic) anhydride, p(FASA), was used to fabricate small diameter insulin microspheres and evaluate their in vivo performance in a type 1 diabetic rat as well as a type 1 diabetic dog model. The process of phase inversion nanoencapsulation was used to fabricate p(FASA) microspheres containing insulin. Using laser diffraction spectrometry, 90% of the microspheres used in the fed double dose rat experiments were found to have a volumetric diameter of 5.9 microm or smaller. In comparison, 90% of the microspheres used in fed single dose rat experiments were found to have a volumetric diameter of 2.6 microm or smaller while the microspheres used in the diabetic dog experiments were found to have a volumetric diameter of 1.2 microm or smaller. Insulin microspheres administered to diabetic rats in the fed double dose experiment produced a relative bioavailability (RB) of 23.3% while insulin microspheres administered to diabetic rats in the fed single dose experiment produced a RB of 5.5+/-1.7%. Insulin microspheres administered to fasted diabetic dogs produced a RB of 5.5+/-3.4%.

  3. Effect of maleic anhydride treatment on the mechanical properties of sansevieria fiber/vinyl ester composites

    NASA Astrophysics Data System (ADS)

    Pradipta, Rangga; Mardiyati, Steven, Purnomo, Ikhsan

    2017-03-01

    Sanseviera trifasciata commonly called mother-in-law tongue also known as snake plant is native to Indonesia, India and Africa. Sansevieria is a new fiber in composite research and has showed promising properties as reinforcement material in polymer matrix composites. Chemical treatment on reinforcing fiber is crucial to reduce hydrophilic tendency and thus improve compatibility with the matrix. In this study, effect of maleic anhydride as chemical treatment on the mechanical properties of Sansevieria fiber/vinyl ester composite was investigated. Sansevieria fibers were immersed by using NaOH 3% for two hours at 100°C and then treated by using maleic anhydrate for two hours at 120°C. Composites were prepared by solution casting with various volume fractions of fiber; 0%, 2.5%, 5%, 7.5% and 10%. Actual density, volume fraction of void and mechanical properties of composite were conducted according to ASTM standard testing methods D792, D3171 and D3039. It was found that mechanical properties of composites increased as volume fractions of fiber was increased. The highest tensile strength and modulus of elasticity of composites were 57.45 MPa and 3.47 GPa respectively, obtained from composites with volume fraction of fiber 10%.

  4. Preparation and Characterization of Extruded Composites Based on Polypropylene and Chitosan Compatibilized with Polypropylene-Graft-Maleic Anhydride.

    PubMed

    Carrasco-Guigón, Fernando Javier; Rodríguez-Félix, Dora Evelia; Castillo-Ortega, María Mónica; Santacruz-Ortega, Hisila C; Burruel-Ibarra, Silvia E; Encinas-Encinas, Jose Carmelo; Plascencia-Jatomea, Maribel; Herrera-Franco, Pedro Jesus; Madera-Santana, Tomas Jesus

    2017-01-25

    The preparation of composites of synthetic and natural polymers represent an interesting option to combine properties; in this manner, polypropylene and chitosan extruded films using a different proportion of components and polypropylene-graft-maleic anhydride (PPgMA) as compatibilizer were prepared. The effect of the content of the biopolymer in the polypropylene (PP) matrix, the addition of compatibilizer, and the particle size on the properties of the composites was analyzed using characterization by fourier transform-infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), differential scanning calorimetry (DSC), tensile strength, and contact angle, finding that in general, the addition of the compatibilizer and reducing the particle size of the chitosan, favored the physicochemical and morphological properties of the films.

  5. Preparation and Characterization of Extruded Composites Based on Polypropylene and Chitosan Compatibilized with Polypropylene-Graft-Maleic Anhydride

    PubMed Central

    Carrasco-Guigón, Fernando Javier; Rodríguez-Félix, Dora Evelia; Castillo-Ortega, María Mónica; Santacruz-Ortega, Hisila C.; Burruel-Ibarra, Silvia E.; Encinas-Encinas, Jose Carmelo; Plascencia-Jatomea, Maribel; Herrera-Franco, Pedro Jesus; Madera-Santana, Tomas Jesus

    2017-01-01

    The preparation of composites of synthetic and natural polymers represent an interesting option to combine properties; in this manner, polypropylene and chitosan extruded films using a different proportion of components and polypropylene-graft-maleic anhydride (PPgMA) as compatibilizer were prepared. The effect of the content of the biopolymer in the polypropylene (PP) matrix, the addition of compatibilizer, and the particle size on the properties of the composites was analyzed using characterization by fourier transform-infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), differential scanning calorimetry (DSC), tensile strength, and contact angle, finding that in general, the addition of the compatibilizer and reducing the particle size of the chitosan, favored the physicochemical and morphological properties of the films. PMID:28772464

  6. Modification of wheat starch with succinic acid/acetic anhydride and azelaic acid/acetic anhydride mixtures I. Thermophysical and pasting properties.

    PubMed

    Subarić, Drago; Ačkar, Durđica; Babić, Jurislav; Sakač, Nikola; Jozinović, Antun

    2014-10-01

    The aim of this research was to investigate the influence of modification with succinic acid/acetic anhydride and azelaic acid/acetic anhydride mixtures on thermophysical and pasting properties of wheat starch. Starch was isolated from two wheat varieties and modified with mixtures of succinic acid and acetic anhydride, and azelaic acid and acetic anhydride in 4, 6 and 8 % (w/w). Thermophysical, pasting properties, swelling power, solubility and amylose content of modified starches were determined. The results showed that modifications with mixtures of afore mentioned dicarboxylic acids with acetic anhydride decreased gelatinisation and pasting temperatures. Gelatinisation enthalpy of Golubica starch increased, while of Srpanjka starch decreased by modifications. Retrogradation after 7 and 14 day-storage at 4 °C decreased after modifications of both starches. Maximum, hot and cold paste viscosity of both starches increased, while stability during shearing at high temperatures decreased. % setback of starches modified with azelaic acid/acetic anhydride mixture decreased. Swelling power and solubility of both starches increased by both modifications.

  7. Risk factors for sensitisation and respiratory symptoms among workers exposed to acid anhydrides: a cohort study

    PubMed Central

    Barker, R. D.; van Tongeren, M. J.; Harris, J. M.; Gardiner, K.; Venables, K. M.; Newman, T

    1998-01-01

    OBJECTIVES: To examine the relation between exposure to acid anhydrides and the risk of developing immediate skin prick test responses to acid anhydride human serum albumin (AA-HSA) conjugates or work related respiratory symptoms; to assess whether these relations are modified by atopy or smoking. METHODS: A cohort of 506 workers exposed to phthalic (PA), maleic (MA), and trimellitic anhydride (TMA) was defined. Workers completed questionnaires relating to employment history, respiratory symptoms, and smoking habits. Skin prick tests were done with AA-HSA conjugates and common inhalant allergens. Exposure to acid anhydrides was measured at the time of the survey and a retrospective exposure assessment was done. RESULTS: Information was obtained from 401 (79%) workers. Thirty four (8.8%) had new work related respiratory symptoms that occurred for the first time while working with acid anhydrides and 12 (3.2%) were sensitised, with an immediate skin prick test reaction to AA-HSA conjugates. Sensitisation to acid anhydrides was associated with work related respiratory symptoms and with smoking at the time of exposure to acid anhydride. When all subjects were included and all three acid anhydrides were taken into account there was no consistent evidence for an exposure-response relation, but with the analysis restricted to a factory where only TMA was in use there was an increased prevalence of sensitisation to acid anhydrides and work related respiratory symptoms with increasing full shift exposure. This relation was apparent within the current occupational exposure standard of 40 micrograms.m-3 and was not modified significantly by smoking or atopy. CONCLUSIONS: Intensity of exposure and cigarette smoking may be risk factors for sensitisation to acid anhydrides. Exposure is also a risk factor for respiratory symptoms. As there was evidence for sensitisation to TMA at full shift exposures within the occupational exposure standard this standard should be reviewed.

  8. Low Viscosity Imides Based on Asymmetric Oxydiphthalic Anhydride

    NASA Technical Reports Server (NTRS)

    Chuang, Kathy C.; Criss, Jim M., Jr.; Mintz, Eric A.; Scheiman, Daniel A.; Nguyen, Baochau N.; McCorkle, Linda S.

    2008-01-01

    A series of low-melt viscosity imide resins were prepared from asymmetric oxydiphthalic dianhydride (a-ODPA) and 4-phenylethynylphthalic anhydride as the endcap, along with 3,4' - oxydianiline (3,4' -ODA), 3,4' -methylenedianiline (3,4' -MDA), 3,3' -methylenedianiline (3,3' - MDA) and 3,3'-diaminobenzophenone (3,3'-DABP), using a solvent-free melt process. These imide oligomers displays low-melt viscosities (2-15 poise) at 260-280 C, which made them amenable to low-cost resin transfer molding (RTM) process. The a-ODPA based RTM resins exhibits glass transition temperatures (Tg's) in the range of 265-330 C after postcure at 343 C. The mechanical properties of these polyimide/carbon fiber composites fabricated by RTM will be discussed.

  9. Protein-Semisynthese mit Hilfe gemischter Anhydride und Enzyme

    NASA Astrophysics Data System (ADS)

    Zahn, H.; Naithani, V. K.; Gattner, H.-G.; Büllesbach, E. E.; Thamm, P. M.

    1981-02-01

    Proteins play a prominent role in nature and their biosynthesis occurs via stepwise combination of amino acids. One can imitate this method in laboratory or synthesize the polypeptide chain by combining smaller preformed fragments (fragment condensation). Reversible protection of reactive groups and solubility problems arising are the most important features in this regard. Semisynthesis, i.e., coupling of amino acids or peptides to natural material may help to overcome these difficulties. The preparation of hybrid preproinsulin by mixed anhydride synthesis and the conversion of pork insulin to human insulin by enzyme-catalyzed peptide synthesis are two examples of the semisynthesis of proteins. In both cases optimal reaction conditions are essential for maximal yield of the product desired. In spite of the rapid improvement of gene technology, chemical peptide synthesis will retain its value for the preparation of biologically and pharmacologically interesting substances.

  10. Evaluation of copolymer conformation states of vinylchloride-maleic anhydride

    NASA Astrophysics Data System (ADS)

    Ivanov, A. A.

    2016-11-01

    The quantum-chemical analysis and experimental study of alternating vinylchloride-maleic anhydride (VC-MA) copolymer macromolecules with polymerization degree 600 have been carried out. The VC-MA copolymer in solvents of different nature undergoes cycloanhydride-enol tautomerism and the macromolecules take the form of corrugated sticks according to viscometric measurements. The computer simulation has shown that the segment with polymerization degree n < 18 (model compound) is not a helix and rolls while if n = 18 the conformations get distorted. The model molecule optimal structure comprising a random sequence of alternating units of comonomers and their enol tautomers with minimal system total energy has been found by the semiempirical parametric method PM3.

  11. Acetylation of barnyardgrass starch with acetic anhydride under iodine catalysis.

    PubMed

    Bartz, Josiane; Goebel, Jorge Tiago; Giovanaz, Marcos Antônio; Zavareze, Elessandra da Rosa; Schirmer, Manoel Artigas; Dias, Alvaro Renato Guerra

    2015-07-01

    Barnyardgrass (Echinochloa crus-galli) is an invasive plant that is difficult to control and is found in abundance as part of the waste of the paddy industry. In this study, barnyardgrass starch was extracted and studied to obtain a novel starch with potential food and non-food applications. We report some of the physicochemical, functional and morphological properties as well as the effect of modifying this starch with acetic anhydride by catalysis with 1, 5 or 10mM of iodine. The extent of the introduction of acetyl groups increased with increasing iodine levels as catalyst. The shape of the granules remained unaltered, but there were low levels of surface corrosion and the overall relative crystallinity decreased. The pasting temperature, enthalpy and other gelatinisation temperatures were reduced by the modification. There was an increase in the viscosity of the pastes, except for the peak viscosity, which was strongly reduced in 10mM iodine.

  12. Perylenetetracarboxylic anhydride as a precursor of fluorescent carbon nanoonion rings.

    PubMed

    Baldoví, Herme G; Herance, José Raul; Manuel Víctor, Víctor; Alvaro, Mercedes; Garcia, Hermenegildo

    2015-08-07

    Thermal annealing at 400 °C of perylenetetracarboxylic anhydride in low molecular mass PEG gives rise to the formation of well defined nanoobjects of 2.5 nm height and size distribution from 10 to 65 nm (average 40 nm) after purification of the raw mixture with silicagel chromatography. TEM reveals that the flat nanoobjects are constituted of concentric graphenic rings (0.34 nm interlayer distance). The morphology of the nanoparticles resembles onion rings of nanometric dimensions (nanoonion rings C-NOR). C-NOR particles have an excitation dependent emission with λem from 430 to 570 nm and a maximum emission quantum yield of 0.49. C-NOR particles can be internalized into Hep3B human hepatoma cells as determined by confocal fluorescence microscopy and are remarkably biocompatible affecting slightly cell viability according to the MTT test.

  13. Perylenetetracarboxylic anhydride as a precursor of fluorescent carbon nanoonion rings

    NASA Astrophysics Data System (ADS)

    Baldoví, Herme G.; Herance, José Raul; Manuel Víctor, Víctor; Alvaro, Mercedes; Garcia, Hermenegildo

    2015-07-01

    Thermal annealing at 400 °C of perylenetetracarboxylic anhydride in low molecular mass PEG gives rise to the formation of well defined nanoobjects of 2.5 nm height and size distribution from 10 to 65 nm (average 40 nm) after purification of the raw mixture with silicagel chromatography. TEM reveals that the flat nanoobjects are constituted of concentric graphenic rings (0.34 nm interlayer distance). The morphology of the nanoparticles resembles onion rings of nanometric dimensions (nanoonion rings C-NOR). C-NOR particles have an excitation dependent emission with λem from 430 to 570 nm and a maximum emission quantum yield of 0.49. C-NOR particles can be internalized into Hep3B human hepatoma cells as determined by confocal fluorescence microscopy and are remarkably biocompatible affecting slightly cell viability according to the MTT test.

  14. Coating carbon nanotubes with polymer in supercritical carbon dioxide.

    PubMed

    Wang, Jiawei; Khlobystov, Andrei N; Wang, Wenxin; Howdle, Steven M; Poliakoff, Martyn

    2006-04-21

    A facile and efficient method has been developed for coating MWNTs with solvent resistant polymer in scCO2, which permits the selective deposition of high molecular weight fluorinated graft poly(methyl vinyl ether-alt-maleic anhydride) polymer onto MWNTs in scCO2 under 100-170 bar at 40 degrees C and forms quasi one-dimensional nanostructures with conducting cores and insulating surfaces.

  15. Carboxy terminated rubber based on natural rubber grafted with acid anhydrides and its adhesion properties

    NASA Astrophysics Data System (ADS)

    Klinpituksa, P.; Kongkalai, P.; Kaesaman, A.

    2014-08-01

    The chemical modification of natural rubber by grafting of various polar functional molecules is an essential method, improving the versatility of rubber in applications. This research investigated the preparation of natural rubber-graft-citraconic anhydride (NR-g-CCA), natural rubber-graft-itaconic anhydride (NR-g-ICA), and natural rubber-graft-maleic anhydride (NR-g-MA), with the anhydrides grafted to natural rubber in toluene using benzoyl peroxide as an initiator. Variations of monomer content, initiator content, temperature and reaction time of the grafting copolymerization were investigated. The maximum degrees of grafting were 1.06% for NR-g-CCA, 4.66% for NR-g-ICA, and 5.03% for NR-g-MA, reached using 10 phr citraconic anhydride, 10 phr of itaconic anhydride, or 8 phr of maleic anhydride, 3 phr benzoyl peroxide, at 85, 80 and 80°C for 2, 2 and 3 hrs, respectively. Solvent-based wood adhesives were formulated from these copolymers with various contents of wood resin in the range 10-40 phr. The maximal 289 N/in cleavage peel and 245.7 KPa shear strength for NR-g-MA (5.03% grafting) were obtained at 40 phr wood resin.

  16. Syntheses of Anthracyclines and Fredericamycin A via Strong Base-Induced Cycloaddition Reaction of Homophthalic Anhydrides

    NASA Astrophysics Data System (ADS)

    Kita, Yasuyuki; Fujioka, Hiromichi

    Strong base-induced cycloaddition reactions of homophthalic anhydrides with quinone derivatives afford peri-hydroxyl aromatic compounds in a regioselective manner. The reactions have been applied to the syntheses of biologically important natural products. This review focuses on the following topics: (i) preparation of homophthalic anhydrides from homophthalic acids using (trimethylsilyl)ethoxyacetylene, (ii) strong base-induced cycloaddition of homophthalic anhydrides with the carbon-carbon double bond and the reaction mechanism, especially addressing the regiochemistry of the reaction, and (iii) application of the reaction to the efficient asymmetric syntheses of anthracyclines and fredericamycin A.

  17. Diastereoselective Synthesis of γ- and δ-Lactams from Imines and Sulfone-Substituted Anhydrides

    PubMed Central

    2015-01-01

    Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol. PMID:24552208

  18. 40 CFR 721.10381 - Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether, hydroxy substituted alkane and...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether, hydroxy substituted alkane and carboxylic acid anhydride, methacrylate terminated... Specific Chemical Substances § 721.10381 Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether...

  19. 40 CFR 721.10381 - Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether, hydroxy substituted alkane and...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether, hydroxy substituted alkane and carboxylic acid anhydride, methacrylate terminated... Specific Chemical Substances § 721.10381 Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether...

  20. 40 CFR 721.10381 - Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether, hydroxy substituted alkane and...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether, hydroxy substituted alkane and carboxylic acid anhydride, methacrylate terminated... Specific Chemical Substances § 721.10381 Cyclic carboxylic acid, polymer with dihydroxy dialkyl ether...

  1. Method of Preparing Polymers with Low Melt Viscosity

    NASA Technical Reports Server (NTRS)

    Jensen, Brian J. (Inventor)

    2001-01-01

    This invention is an improvement in standard polymerizations procedures, i.e., addition-type and step-growth type polymerizations, wherein monomers are reacted to form a growing polymer chain. The improvement includes employing an effective amount of a trifunctional monomer (such as a trifunctional amine anhydride, or phenol) in the polymerization procedure to form a mixture of polymeric materials consisting of branced polymers, star-shaped polymers, and linear polymers. This mixture of polymeric materials has a lower melt temperature and a lower melt viscosity than corresponding linear polymeric materials of equivalent molecular weight.

  2. Fire and heat resistant laminating resins based on maleimido substituted aromatic cyclotriphosphazene polymer

    NASA Technical Reports Server (NTRS)

    Kumar, Devendra (Inventor); Fohlen, George M. (Inventor); Parker, John A. (Inventor)

    1987-01-01

    4-Aminophenoxy cyclotriphosphazenes are reacted with maleic anhydride to produce maleamic acids which are converted to the maleimides. The maleimides are polymerized. By selection of starting materials (e.g., hexakis amino or trisaminophenoxy trisphenoxy cyclotriphosphazenes), selection of molar proportions of reactants, use of mixtures of anhydrides and use of dianhydrides as bridging groups a variety of maleimides and polymers are produced. The polymers have high limiting oxygen indices, high char yields and other useful heat and fire resistant properties making them useful as, for example, impregnants of fabrics.

  3. 21 CFR 872.3500 - Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium...

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. 872.3500 Section 872.3500...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. (a) Identification. Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture...

  4. 21 CFR 872.3500 - Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium...

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. 872.3500 Section 872.3500...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. (a) Identification. Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture...

  5. 21 CFR 872.3500 - Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium...

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. 872.3500 Section 872.3500...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. (a) Identification. Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture...

  6. 21 CFR 872.3500 - Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium...

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. 872.3500 Section 872.3500...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. (a) Identification. Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture...

  7. 21 CFR 872.3500 - Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium...

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. 872.3500 Section 872.3500...), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture adhesive. (a) Identification. Polyvinylmethylether maleic anhydride (PVM-MA), acid copolymer, and carboxymethylcellulose sodium (NACMC) denture...

  8. Highly efficient peptide formation from N-acetylaminoacyl-AMP anhydride and free amino acid

    NASA Technical Reports Server (NTRS)

    Mullins, D. W., Jr.; Lacey, J. C., Jr.

    1983-01-01

    The kinetics of formation of the N-blocked dipeptide, N-acetylglycylglycine, from N-acetylglycyl adenylate anhydride and glycine in aqueous solution at 25 C, and at various PH's are reported. The reaction is of interest in that over a physiologically relevant pH range (6-8), peptide synthesis proceeds more rapidly than hydrolysis, even at those pH's at which this compound becomes increasingly susceptible to base-catalyzed hydrolysis. Under similar conditions, the corresponding unblocked aminoacyl adenylate anhydrides are considerably more unstable, and undergo appreciable hydrlysis in the presence of free amino acid. Because N-blocked aminoacyl adenylate anhydrides serve as model compounds of peptidyl adenylate anhydrides, these results suggest that primitive amino acid polymerization systems may have operated by cyclic reactivation of the peptidyl carboxyl group, rather than that of the incoming amino acid.

  9. Highly efficient peptide formation from N-acetylaminoacyl-AMP anhydride and free amino acid

    NASA Technical Reports Server (NTRS)

    Mullins, D. W., Jr.; Lacey, J. C., Jr.

    1983-01-01

    The kinetics of formation of the N-blocked dipeptide, N-acetylglycylglycine, from N-acetylglycyl adenylate anhydride and glycine in aqueous solution at 25 C, and at various PH's are reported. The reaction is of interest in that over a physiologically relevant pH range (6-8), peptide synthesis proceeds more rapidly than hydrolysis, even at those pH's at which this compound becomes increasingly susceptible to base-catalyzed hydrolysis. Under similar conditions, the corresponding unblocked aminoacyl adenylate anhydrides are considerably more unstable, and undergo appreciable hydrlysis in the presence of free amino acid. Because N-blocked aminoacyl adenylate anhydrides serve as model compounds of peptidyl adenylate anhydrides, these results suggest that primitive amino acid polymerization systems may have operated by cyclic reactivation of the peptidyl carboxyl group, rather than that of the incoming amino acid.

  10. Low molecular weight chemicals, hypersensitivity, and direct toxicity: the acid anhydrides.

    PubMed Central

    Venables, K M

    1989-01-01

    The acid anhydrides are a group of reactive chemicals used widely in alkyd and epoxy resins. The major hazards to health are mucosal and skin irritation and sensitisation of the respiratory tract. Most occupational asthma caused by acid anhydrides appears to be immunologically mediated. Immunological mechanisms have been proposed to explain an influenza-like syndrome and pulmonary haemorrhage, but direct toxicity may also be important in the aetiology of these conditions. PMID:2653411

  11. Grafting of chitosan as a biopolymer onto wool fabric using anhydride bridge and its antibacterial property.

    PubMed

    Ranjbar-Mohammadi, Marziyeh; Arami, Mokhtar; Bahrami, Hajir; Mazaheri, Firoozmehr; Mahmoodi, Niyaz Mohammad

    2010-04-01

    Weak binding of chitosan on the wool constitutes the main problem in its application. In this paper, the surface modification of wool fabric using anhydrides to graft the chitosan was studied. Weight gain, antibacterial and antifelting properties of the chitosan grafted-acylated wool fabric were investigated. Wool fabrics were acylated with two anhydrides, succinic anhydride (SA) and phthalic anhydride (PA), using different solvents (dimethylsulfoxide (DMSO) and N,N-dimethyl formamide (DMF)). The effects of anhydrides, solvents, anhydride concentration, liquor ratio (L:R) and reaction time on acylation of wool were investigated. Chitosan was grafted to the acylated wool and the effects of pH, chitosan concentration, and reaction time on chitosan grafting of acylated wool were evaluated. Fourier transform infra-red (FTIR), scanning electron microscope (SEM), differential scanning colorimetry (DSC) and weight gain analyses provided evidence that chitosan was grafted on to the acylated wool through the formation of new covalent bonds. The grafted samples have antibacterial potential due to existence of the antibacterial property of chitosan. In addition, the chitosan grafted-acylated wool samples have antifelting property. The findings of this research support the potential production of new environmentally friendly textile fabrics. Copyright (c) 2009 Elsevier B.V. All rights reserved.

  12. Convergence of Biological Nitration and Nitrosation via Symmetrical Nitrous Anhydride

    PubMed Central

    Vitturi, Dario A.; Minarrieta, Lucia; Salvatore, Sonia R.; Postlethwait, Edward M.; Fazzari, Marco; Ferrer-Sueta, Gerardo; Lancaster, Jack R.; Freeman, Bruce A.; Schopfer, Francisco J.

    2015-01-01

    Current perspective holds that the generation of secondary signaling mediators from nitrite (NO2−) requires acidification to nitrous acid (HNO2) or metal catalysis. Herein, the use of stable isotope-labeled NO2− and LC-MS/MS analysis of products revealed that NO2− also participates in fatty acid nitration and thiol S-nitrosation at neutral pH. These reactions occur in the absence of metal centers and are stimulated by nitric oxide (•NO) autoxidation via symmetrical dinitrogen trioxide (nitrous anhydride, symN2O3) formation. While theoretical models have predicted physiological symN2O3 formation, its generation is now demonstrated in aqueous reaction systems, cell models and in viv, with the concerted reactions of •NO and NO2− shown to be critical for symN2O3 formation. These results reveal new mechanisms underlying the NO2− propagation of •NO signaling and the regulation of both biomolecule function and signaling network activity via NO2−-dependent nitrosation and nitration reactions. PMID:26006011

  13. Hydrolytic properties of phenylalanyl- and N-acetylphenylalanyl adenylate anhydrides

    NASA Technical Reports Server (NTRS)

    Lacey, J. C., Jr.; Mullins, D. W., Jr.; Senaratne, N.

    1984-01-01

    The hydrolysis of phenylalynyl- and N-acetylephenylalanyl adenylate anhydrides (AcPhe-AMP) is studied experimentally using a new spectrophotometric method. The hydrolysis process was analyzed at low concentrations (0.0001 M), constant temperature of 25 C, constant buffer concentration (0.05 M), and as a function of pH. It is found that while Phe-AMP is susceptible to attack by OH(-), AcPhe-AMP is susceptible to acid decomposition as well. At a pH of 4 to 8, Phe-AMP hydolyzes faster than AcPhe-AMP, but at pH less than four or greater than eight, the blocked form hydrolyzes faster. Both forms are attacked by H2O at the same rate. The rate laws for the various hydrolytic mechanisms and the activation energies for the hydrolyses at pH 7.1 are given in a table, and the possible relevance of the findings to the origin and evolution of the process of protein synthesis is discussed.

  14. Hydrolytic properties of phenylalanyl- and N-acetylphenylalanyl adenylate anhydrides

    NASA Technical Reports Server (NTRS)

    Lacey, J. C., Jr.; Mullins, D. W., Jr.; Senaratne, N.

    1984-01-01

    The hydrolysis of phenylalynyl- and N-acetylephenylalanyl adenylate anhydrides (AcPhe-AMP) is studied experimentally using a new spectrophotometric method. The hydrolysis process was analyzed at low concentrations (0.0001 M), constant temperature of 25 C, constant buffer concentration (0.05 M), and as a function of pH. It is found that while Phe-AMP is susceptible to attack by OH(-), AcPhe-AMP is susceptible to acid decomposition as well. At a pH of 4 to 8, Phe-AMP hydolyzes faster than AcPhe-AMP, but at pH less than four or greater than eight, the blocked form hydrolyzes faster. Both forms are attacked by H2O at the same rate. The rate laws for the various hydrolytic mechanisms and the activation energies for the hydrolyses at pH 7.1 are given in a table, and the possible relevance of the findings to the origin and evolution of the process of protein synthesis is discussed.

  15. Chirally selective, intramolecular interaction observed in an aminoacyl adenylate anhydride

    NASA Technical Reports Server (NTRS)

    Lacey, J. C., Jr.; Hall, L. M.; Mullins, D. W., Jr.; Watkins, C. L.

    1985-01-01

    The interaction between amino acids and nucleotide bases is studied. The proton NMR spectrum of N-acetylphenylalanyl-AMP-anhydride is analyzed H8 and H2 signals, two upfield signals of equal size, and five phenylalanine ring proton signals are observed in the spectrum; the upfield movement of the proton and the racemization of the N-acetyl L-phenylalanine material are examined. The differences in the position of the signals due to the diastereoisomers are investigated. The separation of the D and L amino acyl adenylates using HPLC is described. H-1 NMR spectra of the isomers are examined in order to determine which isomer displays the strongest interaction between the phenyl ring and the adenine ring. The spectra reveal that the L isomer shows the highest upfield change of both H8 and H2 signals. It is noted that the phenyl ring lies over C2 of the adenine ring with the phenyl meta and para protons extended past the adenine ring and the phenyl ortho protons.

  16. Mechanistic study of maleic anhydride grafting onto fatty double bonds using mass spectrometry.

    PubMed

    Loutelier-Bourhis, Corinne; Zovi, Ornella; Lecamp, Laurence; Bunel, Claude; Hubert-Roux, Marie; Lange, Catherine M

    2012-06-15

    The grafting of maleic anhydride onto fatty C=C double bonds is a well-known and used method to functionalize triglyceride molecules. Nevertheless, grafted products are not actually structurally well defined. In this work, the thermal grafting of maleic anhydride onto (un)saturated fatty acid esters without the use of an initiator was characterized in order to determine the nature of the products formed during this reaction. Complementary spectrometric techniques, ESI-MS(n) (ion-trap mass spectrometer), IMS-MS(n) (Q-IMS-TOFMS) and GC/MS, were used to identify the grafted products which were prepared using either ethyl oleate (EtO) or methyl linoleate (MeL) as model molecules and maleic anhydride (MA). Lithiated adducts were investigated since they yield useful structural information when subjected to collision-induced dissociation (CID) in tandem mass spectrometry. A high number of products are formed during MA grafting and various reaction types could occur. Radical addition of maleic anhydride followed by combination or elimination reactions led to succinic and maleic anhydride grafting, respectively. The addition occurred with or without double-bond shift; the resulting derivatives showed succinic and maleic anhydride branching in the α-position relative to the double bond or onto the carbon atom of the initial double bond. Some structures obtained by radical addition and combination were also consistent with the Alder ene functionalization reaction. The Diels-Alder addition between di-unsaturated fatty acid chains and maleic anhydride could yield cyclic forms of MA-grafted derivatives. We have shown that ESI-MS(n) and IMS-MS(n) allow the identification of grafted products providing relevant structural information concerning isomers. These methods permit the rapid and direct analyses of 'crude reaction mixtures'. Copyright © 2012 John Wiley & Sons, Ltd.

  17. Allergy to methyltetrahydrophthalic anhydride in epoxy resin workers.

    PubMed Central

    Nielsen, J; Welinder, H; Horstmann, V; Skerfving, S

    1992-01-01

    One hundred and forty four current and 26 former workers in a plant producing barrels for rocket guns from an epoxy resin containing methyltetrahydrophthalic anhydride (MTHPA; time weighted average air concentration up to 150 micrograms/m3) were studied. They showed higher frequencies of work related symptoms from the eyes (31 v 0%; p < 0.001), nose (53 v 9%; p < 0.001), pharynx (26 v 6%; p < 0.01), and asthma (11 v 0%; p < 0.05) than 33 controls. Also they had higher rates of positive skin prick test to a conjugate of MTHPA and human serum albumin (16 v 0%; p < 0.01), and more had specific IgE and IgG serum antibodies (18 v 0%; p < 0.01 and 12 v 0%; p < 0.05 respectively). There were statistically significant exposure-response relations between exposure and symptoms from eyes and upper airways, dry cough, positive skin prick test, and specific IgE and IgG antibodies. There was a non-significant difference in reaction to metacholine between exposed workers and non-smoking controls. In workers with and without specific IgE antibodies, differences existed in frequency of nasal secretion (54 v 23%; p < 0.05) and dry cough (38 v 12%; p < 0.05). Workers with specific IgG had more dry cough (38 v 12%; p < 0.05), but less symptoms of non-specific bronchial hyperreactivity (0 v 26%; p < 0.05). Atopic workers sneezed more than non-atopic workers (65 v 30%; p < 0.01). In a prospective study five sensitised workers who left the factory became less reactive to metacholine, and became symptom free. In 41 workers who stayed, there was no improvement, despite a 10-fold reduction in exposure. The results show the extreme sensitising properties of MTHPA. PMID:1463677

  18. Blending of Low-Density Polyethylene and Poly-Lactic Acid with Maleic Anhydride as A Compatibilizer for Better Environmentally Food-Packaging Material

    NASA Astrophysics Data System (ADS)

    Setiawan, A. H.; Aulia, F.

    2017-05-01

    The common conventional food packaging materialsare using a thin layer plastic or film, which is made of a synthetic polymer, such as Low-Density Poly Ethylene (LDPE). However, the use of these polymers hasan adverse impact on the environment, because the synthetic polymersare difficult to degrade naturally. Poly-Lactic Acid (PLA) is a biodegradable polymer that can be substituted to synthetic polymers. Since LDPE and PLA have a difference in polarity, therefore the first step of research is to graft them with maleic anhydride (MAH) for increasing the properties of its miscibility. The interaction between them is confirmed by FTIR; whereas the environment issueis characterized by the water adsorption and biodegradability. The FTIR spectra indicated that there had been an interaction between LDPE and MAH and LDPE/LDPE-g-MAH/PLA blend. Increasing PLA content in the blend affected to the increasing in their water absorption and biodegradable. Poly-blend with 20% PLA content was the optimum composition for environmentally food packaging.

  19. [Studies on the characters and microstructure of enzyme and octenyl succinic anhydride modified starch].

    PubMed

    Zhang, Xue-chun; Zheng, Wei-wan; Tu, Zong-cai; Lin, Hong-hui; Wang, Zhen-xing; Kong, Ling-wei

    2010-11-01

    Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), UV-Vis spectra, laser nano size detector (LNSD) and scanning electron microscope (SEM) were employed to analyze the characters and structure of enzyme and octenyl succinic anhydride modified starch. The results indicated that the enzymatic starch reacted with octenyl succinic anhydride, bringing only octenyl succinic anhydride groups but not any other groups. The esterification of enzymatic starch only took place in amorphous region, but had no effect on the crystal form of starch granule. The clarity of EOSS increased with the increase in substitution degree. The particle size of oil emulsion made by EOSS was fine and well-distributed, meaning that the emulsion has excellent emulsibility and emulsifying stability. The embedding of oil encapsulated with EOSS is fine. It can be concluded that the properties of EOSS is excellent, and can be used as emulsifier and wall material of microcapsule.

  20. UNIFAC parameters for maleic anhydride and 2-methyl furan in p-dioxane system

    SciTech Connect

    Daumn, K.J.

    1983-01-01

    The purpose of this work was to develop a method for calculating equilibrium concentrations for reversible liquid phase reactions from a minimum of experimental data. The example reaction studied was the Diels Alder reaction between 2-methyl furan and maleic anhydride. Specifically, interaction parameters of the UNIFAC model for groups in the compounds 2-methyl furan, maleic anhydride and the solvent, p-dioxane, were determined. The activity coefficient of each substance was then predicted by the UNIFAC method. Equilibrium constants at 45/sup 0/C for the Diels Alder reaction between 2-methyl furan and maleic anhydride were then calculated from these activity coefficients and two previously determined sets of equilibrium concentrations at 45/sup 0/C. These two equilibrium constants were within 12% of each other, which demonstrated the validity of the method.

  1. Solubility and dissolution thermodynamics of phthalic anhydride in organic solvents at 283-313 K

    NASA Astrophysics Data System (ADS)

    Wang, Long; Zhang, Fang; Gao, Xiaoqiang; Luo, Tingliang; Xu, Li; Liu, Guoji

    2017-08-01

    The solubility of phthalic anhydride was measured at 283-313 K under atmospheric pressure in ethyl acetate, n-propyl acetate, methyl acetate, acetone, 1,4-dioxane, n-hexane, n-butyl acetate, cyclohexane, and dichloromethane. The solubility of phthalic anhydride in all solvents increased with the increasing temperature. The Van't Hoff equation, modified Apelblat equation, λ h equation, and Wilson model were used to correlate the experimental solubility data. The standard dissolution enthalpy, the standard entropy, and the standard Gibbs energy were evaluated based on the Van't Hoff analysis. The experimental data and model parameters would be useful for optimizing of the separation processes involving phthalic anhydride.

  2. Crystal structure of 2,3-di-methyl-maleic anhydride: continuous chains of electrostatic attraction.

    PubMed

    Wiscons, Ren A; Zeller, Matthias; Rowsell, Jesse L C

    2015-08-01

    In the crystal structure of 2,3-di-methyl-maleic anhydride, C6H6O3, the closest non-bonding inter-molecular distances, between the carbonyl C and O atoms of neighboring mol-ecules, were measured as 2.9054 (11) and 3.0509 (11) Å, which are well below the sum of the van der Waals radii for these atoms. These close contacts, as well as packing motifs similar to that of the title compound, were also found in the crystal structure of maleic anhydride itself and other 2,3-disubstituted maleic anhydrides. Computational modeling suggests that this close contact is caused by strong electrostatic inter-actions between the carbonyl C and O atoms.

  3. Modification of cellulose with succinic anhydride in TBAA/DMSO mixed solvent under catalyst-free conditions

    Treesearch

    Ping-Ping Xin; Yao-Bing Huang; Chung-Yun Hse; Huai N. Cheng; Chaobo Huang; Hui. Pan

    2017-01-01

    Homogeneous modification of cellulose with succinic anhydride was performed using tetrabutylammonium acetate (TBAA)/dimethyl sulfoxide (DMSO) mixed solvent. The molar ratio of succinic anhydride (SA) to free hydroxyl groups in the anhydroglucose units (AGU), TBAA dosage, reaction temperature, and reaction time were investigated. The highest degree of substitution (DS)...

  4. Modification of cellulose with succinic anhydride in TBAA/DMSO mixed solvent under catalyst-free conditions

    USDA-ARS?s Scientific Manuscript database

    Homogeneous modification of cellulose with succinic anhydride was performed in tetrabutylammonium acetate (TBAA)/dimethyl sulfoxide (DMSO) mixed solvent. The molar ratio of succinic anhydride (SA) to free hydroxyl groups in the anhydroglucose units (AGU) and TBAA dosage were investigated as paramete...

  5. Photothermal and morphological characterization of PLA/PCL polymer blends

    NASA Astrophysics Data System (ADS)

    Correa-Pacheco, Z. N.; Jiménez-Pérez, J. L.; Sabino, M. A.; Cruz-Orea, A.; Loaiza, M.

    2015-09-01

    Nowadays, some synthetic polymers have been replaced by biodegradable polymers in order to avoid environmental contamination. Among these biodegradables polymers, aliphatic polyesters such as polylactic acid (PLA) and polycaprolactone (PCL) have been widely used. In the present study, solvent-casting films of PLA, PCL and polymer blends with and without compatibilizer (PLA grafted with maleic anhydride) were prepared. The thermal diffusivity ( α) of each sample was obtained by using the open photoacoustic cell technique. Morphology and thermal properties were determined by using scanning electron microscopy, transmission electron microscopy and differential scanning calorimetry (DSC), respectively. The blends showed lower thermal diffusivity compared to pure polymers. However, when the compatibilizer was used, the highest value of thermal diffusivity was obtained. Also, cold crystallization with the highest value of enthalpy of fusion was observed for the compatibilized sample, which was revealed by DSC. To our knowledge, this is the first time that the thermal diffusivity of these biodegradable polymer blends is reported.

  6. Solvothermal process for grafting maleic anhydride onto poly(ethylene 1-octene)

    NASA Astrophysics Data System (ADS)

    Liu, Qiaochu; Qi, Rongrong; Shen, Yanhan; Zhou, Chixing

    2007-11-01

    Solvothermal process was developed to graft maleic anhydride (MAH) onto poly(ethylene 1-octene) (POE). Fourier transform infrared spectra (FT-IR) and 1H NMR spectra confirmed that maleic anhydride was successfully grafted onto the POE. The influences of MAH content, initiator concentration, POE concentration, reaction temperature, reaction time and solvents on the graft copolymerization were investigated through both of the grafting degree (GD) and gel content (GC). The results demonstrated that high grafting degree (up to 10.85%) could be obtained while the gel content was still low. Further studies revealed that POE-g-MAH could also be achieved in poor solvents of POE through this method.

  7. Synthesis of mixed acid anhydrides from methane and carbon dioxide in acid solvents.

    PubMed

    Zerella, Mark; Mukhopadhyay, Sudip; Bell, Alexis T

    2003-09-04

    [reaction: see text] The reaction of CH(4) with CO(2) has been performed in anhydrous acids using VO(acac)(2) and K(2)S(2)O(8) as promoters. NMR analysis establishes that the primary product is a mixed anhydride of acetic acid and the acid solvent. In sulfuric acid, the overall reaction is CH(4) + CO(2) + SO(3) --> CH(3)C(O)-O-SO(3)H. Hydrolysis of the mixed anhydride produces acetic acid and the solvent acid. When trifluoroacetic acid is the solvent, acetic acid is primarily formed via the reaction CH(4) + CF(3)COOH --> CH(3)COOH + CHF(3).

  8. Preparation of High Density Polyethylene/Waste Polyurethane Blends Compatibilized with Polyethylene-Graft-Maleic Anhydride by Radiation

    PubMed Central

    Park, Jong-Seok; Lim, Youn-Mook; Nho, Young-Chang

    2015-01-01

    Polyurethane (PU) is a very popular polymer that is used in a variety of applications due to its good mechanical, thermal, and chemical properties. However, PU recycling has received significant attention due to environmental issues. In this study, we developed a recycling method for waste PU that utilizes the radiation grafting technique. Grafting of waste PU was carried out using a radiation technique with polyethylene-graft-maleic anhydride (PE-g-MA). The PE-g-MA-grafted PU/high density polyethylene (HDPE) composite was prepared by melt-blending at various concentrations (0–10 phr) of PE-g-MA-grafted PU. The composites were characterized using fourier transform infrared spectroscopy (FT-IR), and their surface morphology and thermal/mechanical properties are reported. For 1 phr PU, the PU could be easily introduced to the HDPE during the melt processing in the blender after the radiation-induced grafting of PU with PE-g-MA. PE-g-MA was easily reacted with PU according to the increasing radiation dose and was located at the interface between the PU and the HDPE during the melt processing in the blender, which improved the interfacial interactions and the mechanical properties of the resultant composites. However, the elongation at break for a PU content >2 phr was drastically decreased. PMID:28788022

  9. In vitro release of clomipramine HCl and buprenorphine HCl from poly adipic anhydride (PAA) and poly trimethylene carbonate (PTMC) blends.

    PubMed

    Dinarvand, Rassoul; Alimorad, Mohammed Massoud; Amanlou, Massoud; Akbari, Hamid

    2005-10-01

    Controlled drug-delivery technology is concerned with the systematic release of a pharmaceutical agent to maintain a therapeutic level of the drug in the body for modulated and/or prolonged periods of time. This may be achieved by incorporating the therapeutic agent into a degradable polymer vehicle, which releases the agent continuously as the matrix erodes. In this study, poly trimethylene carbonate (PTMC), an aliphatic polycarbonate, and poly adipic anhydride (PAA), an aliphatic polyanhydride, were synthesized via melt condensation and ring-opening polymerization of trimethylene carbonate and adipic acid, respectively. The release of clomipramine HCl and buprenorphine HCl from discs prepared with the use of PTMC-PAA blends in phosphate buffer (pH 7.4) are also described. Clomipramine HCl and buprenorphine HCl were both used as hydrophilic drug models. Theoretical treatment of the data with the Peppas model revealed that release of clomipramine HCl (5%) in devices containing 70% PTMC or more followed a Fickian diffusion model. However, the releases of buprenorphine HCl (5%) in the same devices were anomalous. For devices containing 50% and more PAA, surface erosion may play a significant role in the release of both molecules.

  10. Metal phthalocyanine intermediates for the preparation of polymers

    NASA Technical Reports Server (NTRS)

    Achar, B. N.; Fohlen, G. M.; Parker, J. A.

    1985-01-01

    Metal 4, 4', 4"",-tetracarboxylic phthalocyanines (MPTC) are prepared by reaction of trimellitic anhydride, a salt or hydroxide of the desired metal (or the metal in powdered form), urea and a catalyst. A purer form of MPTC is prepared than heretofore. These tetracarboxylic acids are then polymerized by heat to sheet polymers which have superior heat and oxidation resistance. The metal is preferably a divalent metal having an atomic radius close to 1.35A.

  11. Enhancement of mechanical and thermal properties of oil palm empty fruit bunch fiber poly(butylene adipate-co-terephtalate) biocomposites by matrix esterification using succinic anhydride.

    PubMed

    Siyamak, Samira; Ibrahim, Nor Azowa; Abdolmohammadi, Sanaz; Yunus, Wan Md Zin Bin Wan; Rahman, Mohamad Zaki Ab

    2012-02-16

    In this work, the oil palm empty fruit bunch (EFB) fiber was used as a source of lignocellulosic filler to fabricate a novel type of cost effective biodegradable composite, based on the aliphatic aromatic co-polyester poly(butylene adipate-co-terephtalate) PBAT (Ecoflex™), as a fully biodegradable thermoplastic polymer matrix. The aim of this research was to improve the new biocomposites' performance by chemical modification using succinic anhydride (SAH) as a coupling agent in the presence and absence of dicumyl peroxide (DCP) and benzoyl peroxide (BPO) as initiators. For the composite preparation, several blends were prepared with varying ratios of filler and matrix using the melt blending technique. The composites were prepared at various fiber contents of 10, 20, 30, 40 and 50 (wt %) and characterized. The effects of fiber loading and coupling agent loading on the thermal properties of biodegradable polymer composites were evaluated using thermal gravimetric analysis (TGA). Scanning Electron Microscopy (SEM) was used for morphological studies. The chemical structure of the new biocomposites was also analyzed using the Fourier Transform Infrared (FTIR) spectroscopy technique. The PBAT biocomposite reinforced with 40 (wt %) of EFB fiber showed the best mechanical properties compared to the other PBAT/EFB fiber biocomposites. Biocomposite treatment with 4 (wt %) succinic anhydride (SAH) and 1 (wt %) dicumyl peroxide (DCP) improved both tensile and flexural strength as well as tensile and flexural modulus. The FTIR analyses proved the mechanical test results by presenting the evidence of successful esterification using SAH/DCP in the biocomposites' spectra. The SEM micrograph of the tensile fractured surfaces showed the improvement of fiber-matrix adhesion after using SAH. The TGA results showed that chemical modification using SAH/DCP improved the thermal stability of the PBAT/EFB biocomposite.

  12. SELECTIVE HYDROGENATION OF ANHYDRIDES TO LACTONES UNDER SUPERCRITICAL CARBON DIOXIDE MEDIUM

    EPA Science Inventory

    Selective Hydrogenation of Anhydrides to Lactones Under Supercritical Carbon Dioxide Medium

    Endalkachew Sahle-Demessie Unnikrishnan R Pillai
    U.S. EPA , 26 W. Martin Luther King Dr. Cincinnati, OH 45268 Phone: 513-569-7739
    Fax: 513-569-7677
    Abstract:
    Hydrogenat...

  13. A green synthesis of isatoic anhydrides from isatins with urea-hydrogen peroxide complex and ultrasound.

    PubMed

    Deligeorgiev, Todor; Vasilev, Aleksey; Vaquero, Juan J; Alvarez-Builla, Julio

    2007-07-01

    The oxidation of isatins at room temperature, using the cheap and environmentally friendly urea-hydrogen peroxide complex and ultrasonic irradiation, has been investigated. The ultrasonic irradiation dramatically reduces the reaction time. With easy and reproducible reaction procedures, different isatoic anhydrides were obtained in excellent yield and with high purity.

  14. Technical note: Tall oil fatty acid anhydrides as corrosion inhibitor intermediates

    SciTech Connect

    Fischer, E.R.; Parker, J.E. III

    1997-01-01

    Anhydrides derived from tall oil fatty acids offer enhanced corrosion inhibition properties compared to traditional dimer/trimer acids. The chemistry of this intermediate, its use in corrosion inhibition for downhole applications, and the synthesis of novel oil- and water-soluble derivatives were studied.

  15. SELECTIVE HYDROGENATION OF ANHYDRIDES TO LACTONES UNDER SUPERCRITICAL CARBON DIOXIDE MEDIUM

    EPA Science Inventory

    Selective Hydrogenation of Anhydrides to Lactones Under Supercritical Carbon Dioxide Medium

    Endalkachew Sahle-Demessie Unnikrishnan R Pillai
    U.S. EPA , 26 W. Martin Luther King Dr. Cincinnati, OH 45268 Phone: 513-569-7739
    Fax: 513-569-7677
    Abstract:
    Hydrogenat...

  16. TRIMELLITIC ANHYDRIDE-INDUCED EOSINOPHILLA IN A MOUSE MODEL OF OCCUPATIONAL ASTHMA

    EPA Science Inventory

    Trimellitic anhydride (TMA) is a low molecular weight chemical known to cause occupational asthma. The present study was designed to determine if TMA could elicit eosinophil infiltration into the lung of a sensitized mouse similarly to previous studies with the protein allergen ...

  17. TRIMELLITIC ANHYDRIDE-INDUCED EOSINOPHILLA IN A MOUSE MODEL OF OCCUPATIONAL ASTHMA

    EPA Science Inventory

    Trimellitic anhydride (TMA) is a low molecular weight chemical known to cause occupational asthma. The present study was designed to determine if TMA could elicit eosinophil infiltration into the lung of a sensitized mouse similarly to previous studies with the protein allergen ...

  18. Spectroscopic study of phthalic anhydride and its thia, selena, and tellura analogues

    NASA Astrophysics Data System (ADS)

    Bigotto, A.; Galasso, V.; Pellizer, G.; Distefano, G.; Pappalardo, G. C.; Bergman, J.; Engman, L.

    The He(I) photoelectron, u.v.-visible absorption, 1H and 13C NMR, i.r. and Raman-laser spectra of selenophthalic and tellurophthalic anhydride have been obtained and compared to those of phthalic and thiophthalic anhydride. The main features of the spectra of these four compounds (the ordering and splitting of the n CO and π x ionizations, the location and nature of the π → π* transitions, the trend and spread of the chemical shifts, and the symmetry assignments of the fundamental vibrations) have been surveyed and discussed in terms of qualitative and correlative arguments, related to the ability of the chalcogen atoms to transmit electronic effects, and also with the aid of semi-empirical MO calculations. A fair correlation between the average ionization energy of the CO lone pair orbitals, the average of the CO stretching frequencies and the 13C carbonyl chemical shift has been found. The electric dipole moment, measured in benzene at 25°C, is 3.30D for selenophthalic anhydride and 2.71 D for tellurophthalic anhydride.

  19. Nano-encapsulation of coenzyme Q10 using octenyl succinic anhydride modified starch

    USDA-ARS?s Scientific Manuscript database

    Octenyl succinic anhydride modified starch (OSA-ST) was used to encapsulate Coenzyme Q10 (CoQ10). CoQ10 was dissolved in rice bran oil (RBO), and incorporated into an aqueous OSA-ST solution. High pressure homogenization (HPH) of the mixture was conducted at 170 MPa for 5-6 cycles. The resulting ...

  20. Position of modifying groups on starch chains of octenylsuccinic anhydride-modified waxy maize starch

    USDA-ARS?s Scientific Manuscript database

    Octenylsuccinic anhydride (OSA)-modified starches with degree of substitution of 0.018 (OS-S-L) and 0.092 (OS-S-H) were prepared from granular native waxy maize starch in an aqueous slurry system. The substitution distribution of OS groups was investigated by enzyme hydrolysis followed by chromatogr...

  1. Formation and stability of Vitamin E enriched nanoemulsions stabilized by Octenyl Succinic Anhydride modified starch

    USDA-ARS?s Scientific Manuscript database

    Vitamin E (VE) is highly susceptible to autoxidation; therefore, it requires systems to encapsulate and protect it from autoxidation.In this study,we developed VE delivery systems, which were stabilized by Capsul® (MS), a starch modified with octenyl succinic anhydride. Influences of interfacial ten...

  2. TRIMELLITIC ANHYDRIDE (TMA) HYPERSENSITIVITY IN MICE AFTER DERMAL AND INTRATRACHAEL (IT) EXPOSURES

    EPA Science Inventory

    ABSTRACT for 2001 DMS213

    TRIMELLITIC ANHYDRIDE (TMA) HYPERSENSITIVITY IN
    MICE AFTER DERMAL AND INTRATRACHEAL (IT) EXPOSURES. E Boykin, M Ward, MJ Selgrade, and D Sailstad. NHEERL, ORD, US EPA, RTP, NC, USA.
    TMA causes respiratory hypersensitivity (RH) responses. W...

  3. TRIMELLITIC ANHYDRIDE (TMA) HYPERSENSITIVITY IN MICE AFTER MULTIPLE INTRATRACHAEL (IT) EXPOSURE

    EPA Science Inventory

    SOT 2001 DMS214

    TRIMELLITIC ANHYDRIDE (TMA) HYPERSENSITIVITY IN
    MICE AFTER MULTIPLE INTRATRACHEAL (IT) EXPOSURES. D Sailstad, E Boykin, M Ward, and MJ Selgrade. NHEERL, ORD, US EPA, RTP, NC, USA.
    TMA causes Th2 related respiratory hypersensitivity (RH) responses. W...

  4. Polymer films

    DOEpatents

    Granick, Steve; Sukhishvili, Svetlana A.

    2008-12-30

    A film contains a first polymer having a plurality of hydrogen bond donating moieties, and a second polymer having a plurality of hydrogen bond accepting moieties. The second polymer is hydrogen bonded to the first polymer.

  5. Polymer films

    DOEpatents

    Granick, Steve; Sukhishvili, Svetlana A.

    2004-05-25

    A film contains a first polymer having a plurality of hydrogen bond donating moieties, and a second polymer having a plurality of hydrogen bond accepting moieties. The second polymer is hydrogen bonded to the first polymer.

  6. Deposition of antibacterial of poly(1,3-bis-(p-carboxyphenoxy propane)-co-(sebacic anhydride)) 20:80/gentamicin sulfate composite coatings by MAPLE

    NASA Astrophysics Data System (ADS)

    Cristescu, R.; Popescu, C.; Socol, G.; Visan, A.; Mihailescu, I. N.; Gittard, S. D.; Miller, P. R.; Martin, T. N.; Narayan, R. J.; Andronie, A.; Stamatin, I.; Chrisey, D. B.

    2011-04-01

    We report on thin film deposition of poly(1,3-bis-(p-carboxyphenoxy propane)-co-sebacic anhydride)) 20:80 thin films containing several gentamicin concentrations by matrix assisted pulsed laser evaporation (MAPLE). A pulsed KrF* excimer laser was used to deposit the polymer-drug composite thin films. Release of gentamicin from these MAPLE-deposited polymer conjugate structures was assessed. Fourier transform infrared spectroscopy was used to demonstrate that the functional groups of the MAPLE-transferred materials were not changed by the deposition process nor were new functional groups formed. Scanning electron microscopy confirmed that MAPLE may be used to fabricate thin films of good morphological quality. The activity of gentamicin-doped films against Escherichia coli and Staphylococcus aureus bacteria was demonstrated using disk diffusion and antibacterial drop test. Our studies indicate that deposition of polymer-drug composite thin films prepared by MAPLE is a suitable technique for performing controlled drug delivery. Antimicrobial thin film coatings have several medical applications, including use for indwelling catheters and implanted medical devices.

  7. [The working environment control of anhydride hardeners from an epoxy resin system].

    PubMed

    Matsumoto, Naomi; Yokota, Kozo; Johyama, Yasushi; Takakura, Toshiyuki

    2003-07-01

    Epoxy resins are widely used in adhesives, coatings, materials for molds and composites, and encapsulation. Acid anhydrides such as methyltetrahydrophthalic anhydride are being used as curing agents for epoxy resins. The anhydride hardeners are well-known industrial inhalant allergens, inducing predominantly type I allergies. In the electronic components industry, these substances have been consumed in large quantities. Therefore, safe use in the industry demands control of the levels of exposure causing allergic diseases in the workshop. We conducted a prospective survey of two electronics plants to clarify how to control the atmospheric level of the anhydrides in the work environment. Measurements of the levels of the anhydrides in air started according to the Working Environment Measurement Standards (Ministry of Labour Notification No. 46, 1976) in April 2000, along with improvements in the work environment. A value of 40 micrograms/m3 was adopted as the administrative control level to judge the propriety of the working environment control. A total of 2 unit work areas in both plants belonged to Control Class III. The exposure originated from manual loading, casting, uncured hot resins, and leaks in an impregnating-machine or curing ovens. In order to achieve the working environment control, complete enclosure of the source, installation of local exhaust ventilation, and improvement or maintenance of the local exhaust ventilation system were performed on the basis of the results of the working environment measurement, with the result that the work environment was improved (Control Class I). It became evident that these measures were effective just like other noxious substances.

  8. Microwave synthesis and thermal properties of polyacrylate derivatives containing itaconic anhydride moieties

    PubMed Central

    2012-01-01

    Background Microwave irradiation as an alternative heat source is now a well-known method in synthetic chemistry. Microwave heating has emerged as a powerful technique to promote a variety of chemical reactions, offering reduced pollution, low cost and offer high yields together with simplicity in processing and handling. On the other hand, copolymers containing both hydrophilic and hydrophobic segments are drawing considerable attention because of their possible use in biological systems. Various copolymer compositions can produce a very large number of different arrangements, producing materials of varying chemical and physical properties. Thus, the hydrophilicity of copolymers can be modified by changing the amount of incorporated itaconic anhydride. Results A series of methyl methacrylate (MMA) and acrylamide (AA) copolymers containing itaconic anhydride (ITA) were synthesized by microwave irradiation employing a multimode reactor (Synthos 3000 Aton Paar, GmbH, 1400 W maximum magnetron) as well as conventional method. The thermal properties of the copolymers were evaluated by different techniques. Structure-thermal property correlation based on changing the itaconic anhydride ratio was demonstrated. Results revealed that the incorporation of itaconic anhydride into the polymeric backbone of all series affect the thermal stability of copolymers. In addition, the use of the microwave method offers high molecular weight copolymers which lead eventually to an increase in thermal stability. Conclusions Microwave irradiation method showed advantages for the produced copolymers compared to that prepared by conventional method, where it can offer a copolymer in short time, high yield, more pure compounds and more thermally stable copolymers, rather than conventional method. Also, microwave irradiation method gives higher molecular weight due to prevention of the chain transfer. Moreover, as the itaconic anhydride content increases the thermal stability and Tg increase

  9. PLA branching with anhydrides and tri-functional aziridine

    NASA Astrophysics Data System (ADS)

    Gu, Liangliang; Xu, Yuewen; Naredla, Rajasekhar; Hoye, Thomas; Macosko, Christopher

    Branched PLA was prepared by melt blending with tri-functional aziridine (T-Az) and pyromellitic dianhydride (PMDA). 1HNMR, gel permeation chromatography (GPC) and rheology were used to characterize the topological structures of branched PLA. Fast reaction between PLA carboxyl end group and T-Az resulted in 3-arm stars and increased the molecular weight. However, the 3-arm stars did not show strain hardening behavior under extensional flow. After modifying PLA hydroxyl end group with PMDA, PLA can react with T-Az on both chain ends and form long chain branched structure, which showed strain hardening in extension. It was found that that only 10% of the PLA hydroxyl end groups reacted with PMDA. This work is supported by Center for Sustainable Polymers.

  10. Physical insights into salicylic acid release from poly(anhydrides).

    PubMed

    Dasgupta, Queeny; Chatterjee, Kaushik; Madras, Giridhar

    2016-01-21

    Salicylic acid (SA) based biodegradable polyanhydrides (PAHs) are of great interest for drug delivery in a variety of diseases and disorders owing to the multi-utility of SA. There is a need for the design of SA-based PAHs for tunable drug release, optimized for the treatment of different diseases. In this study, we devised a simple strategy for tuning the release properties and erosion kinetics of a family of PAHs. PAHs incorporating SA were derived from related aliphatic diacids, varying only in the chain length, and prepared by simple melt condensation polymerization. Upon hydrolysis induced erosion, the polymer degrades into cytocompatible products, including the incorporated bioactive SA and diacid. The degradation follows first order kinetics with the rate constant varying by nearly 25 times between the PAH obtained with adipic acid and that with dodecanedioic acid. The release profiles have been tailored from 100% to 50% SA release in 7 days across the different PAHs. The release rate constants of these semi-crystalline, surface eroding PAHs decreased almost linearly with an increase in the diacid chain length, and varied by nearly 40 times between adipic acid and dodecanedioic acid PAH. The degradation products with SA concentration in the range of 30-350 ppm were used to assess cytocompatibility and showed no cytotoxicity to HeLa cells. This particular strategy is expected to (a) enable synthesis of application specific PAHs with tunable erosion and release profiles; (b) encompass a large number of drugs that may be incorporated into the PAH matrix. Such a strategy can potentially be extended to the controlled release of other drugs that may be incorporated into the PAH backbone and has important implications for the rational design of drug eluting bioactive polymers.

  11. Thermal stability of sulfonated polymers

    SciTech Connect

    Audibert, A.; Argillier, J.F.

    1995-11-01

    Polyacrylamides which are used in oil applications i.e. polymer flooding and water based muds, are hydrolyzed versus time and temperature. This leads to a lack of tolerance towards electrolyte contamination and to a rapid degradation inducing a loss of their properties. Modifications of polyacrylamide structure have been proposed to postpone their thermal stability to higher temperatures. Monomers such as acrylamido methylpropane sulfonate (AMPS) or sulfonated styrene/maleic anhydride can be used to prevent acrylamide comonomer from hydrolysis. The aim of this work is to study under controlled conditions, i.e. anaerobic atmosphere, neutral pH, the stability of sulfonated polymers in order to distinguish between hydrolysis and radical degradation reactions. It has been observed that up to 100 C, the AMPS group is stable and protects the acrylamide function from hydrolysis up to 80%. At higher temperature, even the hydrolysis of the AMPS group occurs, giving acrylate and {beta},{beta} dimethyl taurine, with a kinetics that depends on temperature and time. Degradation in terms of molecular weight then occurs indicating that it follows a radical decarboxylation reaction. It can be limited either by the use of free radical scavenger or when the polymer is in the presence of a mineral phase such as bentonite. These results provide valuable data for the determination of the limits of use of sulfonated copolymers and guidelines for optimizing chemical structure of sulfonated polymers used in water based formulation, in particular to enhance their thermal stability.

  12. Contributions of polymers to bentonite and saponite fluids

    SciTech Connect

    Guven, N.; Carney, L.L.; Panfil, D.J. . Dept. of Geosciences)

    1991-02-01

    Polymers have been used in drilling fluids for many years. However, the confusion surrounding the use of polymers in the oil field has severely limited their effectiveness. Many oilfield workers simply put all polymers in the same category without regard to the many differences that exist among them. Homopolymers and copolymers of acrylic acid and a copolymer of styrene and maleic anhydride are found to have profound effects on the rheological and filtration properties of clay-based fluids up to 300{degrees}F. These contributions of the polymers are greatly diminished when the clay/polymer fluids were autoclaved at 400{degrees}F. Thus, the effects of these polymers are expected to be negligible at and above 400{degrees}F. Homo- and co-polymers of acrylic acid with molecular weights below 5000 almost eliminate the anomalous viscosity rise of the bentonite fluids at temperatures between 250--450{degrees}F. A homopolymer of acrylic acid with a molecular weight of 60,000 and a co-polymer of styrene and maleic anhydride with very high molecular weight further enhances the anomalous viscosity rise of the bentonite fluid. The original viscosity profile of the saponite fluid is characterized with a high initial viscosity up to 200{degrees}F which is followed by a steep thinning at higher temperatures. The addition of homo- and co-polymer of acrylic acid causes a complete reversal in the fluid viscosity. They become thin at lower temperatures (up to 250{degrees}F) and experience a sudden viscosity rise at higher temperatures. All the above polymers greatly improve the filtration losses of the fluids at room temperatures as indicated by the API test. The filtration tests at high pressure and high temperatures were inconclusive due to the frequent blow-outs that occur during the tests.

  13. Ruthenium-catalyzed decarbonylative addition reaction of anhydrides with alkynes: a facile synthesis of isocoumarins and α-pyrones.

    PubMed

    Prakash, Rashmi; Shekarrao, Kommuri; Gogoi, Sanjib; Boruah, Romesh C

    2015-06-21

    A novel ruthenium catalyzed straightforward and efficient synthesis of isocoumarin and α-pyrone derivatives has been accomplished by the decarbonylative addition reaction of anhydrides with alkynes under thermal conditions.

  14. Palladium-catalyzed regioselective carbonylation of C-H bonds of N-alkyl anilines for synthesis of isatoic anhydrides.

    PubMed

    Guan, Zheng-Hui; Chen, Ming; Ren, Zhi-Hui

    2012-10-24

    A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions.

  15. 1,3-Dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: formation of novel benzodiazepinones.

    PubMed

    D'Souza, Asha M; Spiccia, Nadia; Basutto, Jose; Jokisz, Pawel; Wong, Leon S-M; Meyer, Adam G; Holmes, Andrew B; White, Jonathan M; Ryan, John H

    2011-02-04

    A nonstabilized azomethine ylide reacts with a wide range of substituted isatoic anhydrides to afford novel 1,3-benzodiazepin-5-one derivatives, which are generally isolated in high yield. The transformations involve 1,3-dipolar cycloaddition reactions of the ylide with the anhydrides to give transient, and in a representative case spectroscopically observable, oxazolidine intermediates that undergo ring-opening-decarboxylation-ring-closing reaction cascades to yield the 1,3-benzodiazepin-5-one products.

  16. On the Formation of Maleic Anhydride on a Vanadyl Pyrophosphate Surface: A Theoretical Study of the Mechanism

    DTIC Science & Technology

    1990-05-25

    synthesis of maleic anhydride from n - butane over a vanadium phosphorous oxide surface in the presence of molecular oxygen [equation ( 1 )]. 7 / • 3.5 0 2 (g...active vanadium phosphorous oxide phase in the oxidation of n - butane has been disputed in the literature. 7 0, 0 Generally, it is agreed that the presence...mechanism for the selective oxidation of n - butane to maleic anhydride. Satsuma et al. have described the surface structure in terms of the number of

  17. Preparation and Mechanical Properties of Chitosan-graft Maleic Anhydride Reinforced with Montmorillonite

    NASA Astrophysics Data System (ADS)

    Fajrin, A.; Sari, L. A.; Rahmawati, N.; Saputra, O. A.; Suryanti, V.

    2017-02-01

    The research aims to develop biodegradable composites as bio-based plastics from chitosan. The composites were prepared via solution casting method by introducing the maleic anhydride (MAH) as grafting agent and montmorillonite (MMt) as reinforcement. The grafting process of chitosan was conducted by varying concentrations of MAH which were 10, 20, and 30% w/w. It was observed that the chitosan-graft-maleic anhydride (Cs-g-MAH) containing 10% w/w of MAH increased its tensile strength by 70%. Reinforcement material was added to the Cs-g-MAH by varying MMt concentrations, e.g. 3, 6, 9 and 12% w/w. It was noted that the presence of 9% w/w of MMt in the Cs-g-MAH gave the best mechanical properties of the Cs-g-MAH/MMt composite.

  18. Formic Sulfuric Anhydride: a New Chemical Species with Possible Implications for Atmospheric Aerosol

    NASA Astrophysics Data System (ADS)

    Mackenzie, Becca; Dewberry, Chris; Leopold, Ken

    2015-06-01

    Aerosols are important players in the Earth's atmosphere, affecting climate, cloud formation, and human health. In this work, we report the discovery of a previously unknown molecule, formic sulfuric anhydride (FSA), that may influence the formation and composition of atmospheric aerosol particles. Five isotopologues of FSA have been observed by microwave spectroscopy and further characterized using DFT calculations. The system has dipole moment components along all three inertial axes, and indeed a, b, and c-type transitions have been observed. A π2 + π2 + σ2 cycloaddition reaction between SO3 and HCOOH is proposed as a possible mechanism for the formation of FSA and calculations indicate that the transformation is effectively barrierless. Facile formation of the anhydride followed by hydrolysis in small water-containing clusters or liquid droplets may provide a mechanism of incorporating volatile organics into atmospheric aerosol. We suggest that FSA and its derivatives be considered in future atmospheric and climate models.

  19. Compatibility of anhydride cured epoxies with hexanitroazobenzene (HNAB) and hexanitrostilbene (HNS)

    SciTech Connect

    Massis, T.M.; Wischmann, K.B.

    1985-01-01

    The explosives HNAB (hexanitroazobenzene) and HNS (hexanitrostilbene) have compatibility problems with amine-cured epoxy systems. A program was instituted to find compatible polymeric substitutes for use with these explosives. These polymeric materials must have rigid structures after curing for both adhesive and encapsulant applications. A promising class of epoxy materials using anhydride curing agents with various catalysts to trigger the cure reaction were developed. These polymeric systems have very good compatibility with HNS. Of those tested with HNAB, the anhydride epoxy system that used uranyl nitrate as the catalyst was found to be marginally compatible while the others were incompatible. These results indicated further studies are needed. The CRT (chemical reactivity test) was used to evaluate the compatibility of these materials. 6 references, 2 figures, 5 tables.

  20. Electron paramagnetic resonance and FT-IR spectroscopic studies of glycine anhydride and betaine hydrochloride

    NASA Astrophysics Data System (ADS)

    Halim Başkan, M.; Kartal, Zeki; Aydın, Murat

    2015-12-01

    Gamma irradiated powders of glycine anhydride and betaine hydrochloride have been investigated at room temperature by electron paramagnetic resonance (EPR). In these compounds, the observed paramagnetic species were attributed to the R1 and R2 radicals, respectively. It was determined that the free electron interacted with environmental protons and 14N nucleus in both radicals. The EPR spectra of gamma irradiated powder samples remained unchanged at room temperature for two weeks after irradiation. Also, the Fourier Transform Infrared (FT-IR), FT-Raman and thermal analyses of both compounds were investigated. The functional groups in the molecular structures of glycine anhydride and betaine hydrochloride were identified by vibrational spectroscopies (FT-IR and FT-Raman).

  1. Enhanced activity of immobilized dimethylmaleic anhydride-protected poly- and monoclonal antibodies.

    PubMed

    Hadas, E; Koppel, R; Schwartz, F; Raviv, O; Fleminger, G

    1990-06-27

    The effect of reversible protection of the free amino groups of poly- and monoclonal antibodies by dimethylmaleic anhydride on their binding activity following immobilization onto various carriers was studied. The treatment with dimethylmaleic anhydride resulted in a 1.6-1.8-fold increase in the activity of immobilized goat anti-mouse immunoglobulin antibody immobilized onto different epoxy containing carriers and a 3-10.7-fold increase in the activity of immobilized monoclonal antibodies specific for carboxypeptidase A. The increase in activity was most pronounced at low antigen to carrier loads and over a wide range of modifier to protein ratios. The application of reversible protection of antibodies may permit the development of highly active immobilized antibody preparations for use in immunoaffinity purification.

  2. Effect of impurities in polybutene on the quality of alkenylsuccinic anhydrides

    SciTech Connect

    Yarmolyuk, B.M.; Pustovit, V.E.; Bereza, L.I.; Antonov, V.N.; Shablii, V.I.; Vititneva, L.A.

    1984-03-01

    Synthesis of alkenylsuccini anhydrides (ASAs) was carried out in thermostable ampules at 230/sup 0/C in the course of 12 hours at an MA:PB molar ratio of 1.3:1 in a medium of prepurified petroleum xylene (30%). Freshly distilled maleic anhydride and industrial specimens of polybutene were used in the experiments. It was established that the main impurities which are formed in the production of polybutene and in its processing are ions of sodium, peroxide compounds and products of decomposition of the polymerization catalyst. The concentration of sodium ion was determined by an atomic adsorption method on an A-3000 instrument, the concentration of peroxides was determined by iodometry (3), and the concentration of catalyst decomposition products was determined from the amount of mechanical impurities.

  3. Wheat Gluten Blends with Maleic Anhydride-Functionalized Polyacrylate Cross-Linkers for Improved Properties.

    PubMed

    Diao, Cheng; Xia, Hongwei; Parnas, Richard S

    2015-10-14

    A family of polyacrylate-based cross-linkers was synthesized to maximize the toughness of high Tg, high modulus wheat gluten blends in the glassy state. Mechanical testing and damping measurements were conducted to provide an example where the work of fracture and strength of the blend substantially exceeds polystyrene while maintaining flexure stiffness in excess of 3 GPa. The new rubbery cross-linkers, polymethyl acrylate-co-maleic anhydride and polyethyl acrylate-co-maleic anhydride, improve WG mechanical properties and reduce water absorption simultaneously. MDSC, FTIR, HPLC, and NMR data confirmed the cross-linking reaction with wheat gluten. Flexural, DMA, and water absorption testing were carried out to characterize the property improvements. DMA was conducted to investigate the relationship between energy damping and mechanical property improvement. If the cross-linker damping temperature is close to the testing temperature, the entire sample exhibits high damping, toughness, and strength.

  4. Amino acid dependent formation of phosphate anhydrides in water mediated by carbonyl sulfide.

    PubMed

    Leman, Luke J; Orgel, Leslie E; Ghadiri, M Reza

    2006-01-11

    Carbonyl sulfide (COS), a component of volcanic gas emissions and interstellar gas clouds, is shown to be an efficient condensing agent in the context of phosphate chemistry in aqueous solutions. We report that high-energy aminoacyl-phosphate anhydrides and aminoacyl adenylates are generated in solutions containing amino acids, COS, and the corresponding phosphate molecule. We further show that the mixed anhydrides of amino acids and inorganic phosphate are phosphorylating agents, producing pyrophosphate in better than 30% yield in the presence of Ca2+ precipitates. The amino acid dependent activations of phosphate reported here, which occur in parallel with the production of peptides, suggest that these two reactions may have shared a common intermediate on the prebiotic Earth.

  5. Stereocontrol in Asymmetric γ-Lactam Syntheses from Imines and Cyanosuccinic Anhydrides

    PubMed Central

    Pattawong, Ommidala; Tan, Darlene Q.; Fettinger, James C.; Shaw, Jared T.; Cheong, Paul Ha-Yeon

    2014-01-01

    Computations (SCS-MP2//B3LYP) reveal that the asymmetric synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds through a Mannich reaction between the enol form of the anhydride and the E-imine, followed by a transannular acylation. This new mechanistic picture accounts for both the observed reactivity and stereoselectivity. CH-O and hydrogen bonding interactions in the Mannich step and torsional steering effects in the acylation step are responsible for stereocontrol. It is demonstrated that this new mechanistic picture applies to the related reactions of homophthalic anhydrides with imines and presents new vistas for the design of a new reaction to access complex molecular architectures. PMID:24070216

  6. Palladium-catalyzed decarboxylative coupling of isatoic anhydrides with arylboronic acids.

    PubMed

    Lu, Wei; Chen, Jiuxi; Liu, Miaochang; Ding, Jinchang; Gao, Wenxia; Wu, Huayue

    2011-11-18

    The decarboxylative coupling of isatoic anhydrides with arylboronic acids was realized for the first time in the presence of Pd(2)(dba)(3) and DPEphos, achieving aryl o-aminobenzoates with yields ranging from moderate to good. The efficiency of this procedure was demonstrated by good compatibility with fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, formacyl, acetyl, thienyl, and naphthyl groups. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from dioxygen.

  7. THE REACTIONS OF 2- AND 4-PICOLINE N-OXIDES WITH PHENYLACETIC ANHYDRIDE.

    DTIC Science & Technology

    pyridinemethanol phenylacetate (X) and 2-phenylethylpyridine (XI) in the case of 2-picoline N-oxide and of 4 - pyridinemethanol phenylacetate (XIV) and 4 ...The reactions of 2- and 4 -picoline N-oxide with phenylacetic anhydride yield the oxidation-reduction products, benzaldehyde, carbon dioxide...phenylethylpyridine (XV) in the case of 4 -picoline N-oxide. The product composition is unchanged when the reactions are performed in the presence of the radical

  8. Phthalic anhydride production from hemicellulose solutions: Technoeconomic analysis and life cycle assessment

    SciTech Connect

    Lin, Zhaojia; Ierapetritou, Marianthi; Nikolakis, Vladimiros

    2015-07-14

    The process synthesis, technoeconomic analysis, and life cycle assessment (LCA) of a novel route for phthalic anhydride (PAN) production from hemicellulose solutions are presented. The production contains six steps including dehydration of xylose to furfural, reductive decarbonylation of furfural to furan, oxidation of furfural to maleic anhydride (MA), Diels-Alder cycloaddition of furan, and MA to exo-4,10-dioxa-tricyclo[5.2.1.0]dec-8-ene-3,5-dione followed by dehydration to PAN in the presence of mixture of methanesulfonic acid and acetic anhydride (AAN) which is converted to acetyl methanesulfonate and acetic acid (AAD), and dehydration of AAD to AAN. The minimum selling price of PAN is determined to be $810/metric ton about half of oil-based PAN. The coproduction of high-value products is essential to improve the economics. Biomass feedstock contributes to the majority of cost. LCA results shows that biomass-based PAN has advantages over oil-based PAN to reduce climate change and fossil depletion however requires more water usage.

  9. Novel synthetic method for the preparation of amphiphilic hyaluronan by means of aliphatic aromatic anhydrides.

    PubMed

    Huerta-Angeles, Gloria; Bobek, Martin; Příkopová, Eva; Šmejkalová, Daniela; Velebný, Vladimír

    2014-10-13

    The present work describes a novel and efficient method of synthesis of amphiphilic hyaluronan (HA) by esterification with alkyl fatty acids. These derivatives were synthesized under mild aqueous and well controlled conditions using mixed aliphatic aromatic anhydrides. These anhydrides characterized by the general formula RCOOCOC6H2Cl3 can be easily prepared by the reaction of the corresponding fatty acid (R) with 2,4,6-trichlorobenzoyl chloride (TCBC) in the presence of triethylamine. The aliphatic aromatic anhydrides RCOOCOC6H2Cl3 then react with the polysaccharide and enable the synthesis of aliphatic acid esters of HA in good yields. No hydrolytic degradation of hyaluronic acid could be observed. Parameters controlling the degree of esterification were systematically studied. Fatty acids with different chain lengths can be introduced applying this methodology. The degree of substitution was decreasing with increasing length of hydrophobic chain. The reaction products were fully characterized by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), SEC-MALLS and chromatographic analyses. Although the esterified HA products exhibited aggregation in solution as demonstrated by NMR, microscopy and rheology, they were still water-soluble.

  10. Study on oil absorbency of succinic anhydride modified banana cellulose in ionic liquid.

    PubMed

    Shang, Wenting; Sheng, Zhanwu; Shen, Yixiao; Ai, Binling; Zheng, Lili; Yang, Jingsong; Xu, Zhimin

    2016-05-05

    Banana cellulose contained number of hydrophilic hydroxyl groups which were succinylated to be hydrophobic groups with high oil affinity. Succinic anhydride was used to modify banana cellulose in 1-allyl-3-methylimidazolium chloride ionic liquid in this study. The modified banana cellulose had a high oil absorption capacity. The effects of reaction time, temperature, and molar ratio of succinic anhydride to anhydroglucose on the degree of substitution of modified banana cellulose were evaluated. The optimal reaction condition was at a ratio of succinic anhydride and anhydroglucose 6:1 (m:m), reaction time 60min and temperature 90°C. The maximum degree of acylation reaction reached to 0.37. The characterization analysis of the modified banana cellulose was performed using X-ray diffractometer, Fourier transform infrared spectrometer, scanning electron microscopy and thermogravimetry. The oil absorption capacity and kinetics of the modified banana cellulose were evaluated at the modified cellulose dose (0.025-0.3g), initial oil amount (5-30g), and temperature (15-35°C) conditions. The maximum oil absorption capacity was 32.12g/g at the condition of the cellulose dose (0.05g), initial oil amount (25g) and temperature (15°C). The kinetics of oil absorption of the cellulose followed a pseudo-second-order model. The results of this study demonstrated that the modified banana cellulose could be used as an efficient bio-sorbent for oil adsorption.

  11. Reevaluation of Tetrahydrophthalic Anhydride as an End Cap for Improved Oxidation Resistance in Addition Polyimides

    NASA Technical Reports Server (NTRS)

    Meador, Mary Ann B.; Frimer, Aryeh A.; Johnston, J. Christopher

    2003-01-01

    Several substituted 1,2,3,6-tetrahydrophthalic anhydride end caps - including the 3-phenyl, 3-methoxy, 3-trimethylsilyloxy, and 3,6-diphenyl analogs - were synthesized via the Diels-Alder condensation of the corresponding butadienes and maleic anhydride. These anhydrides, as well as the commercially available 3-hydro and 4-methyl analogs, were each ground together with methylenedianiline in a 2:1 ratio and heated gradually from 204 C to 371 C, with the thermolysis followed by NMR. Generally speaking, a transformation via monoimide to bisimide was observed in the lower temperature range, followed by competition between crosslinking and aromatization. We believe that this competition produces a substantial percentage of aromatic product, with the concomitant lowering of the relative amount of crosslinking and is responsible for improving both thermal oxidative stability of tetrahydrophthalic end capped polyimides and their substantial frangibility. The thermolysis of the tetrahydrophthalimides under inert atmosphere dramatically lowers the amount of aromatization hence, the mechanism for aromatization is an oxidative one.

  12. Synthesis and characterization of maleic anhydride esterified corn starch by the dry method.

    PubMed

    Zuo, Yingfeng; Gu, Jiyou; Yang, Long; Qiao, Zhibang; Tan, Haiyan; Zhang, Yanhua

    2013-11-01

    Maleic anhydride esterified starch was synthesized by a dry method using corn starch as the material and maleic anhydride as the esterifying agent. The esterified starch (ES) was analyzed by Fourier transform infrared spectroscopy (FTIR) and X-ray photoelectron spectroscopy (XPS), which confirmed that there was a successful esterification reaction between the maleic anhydride and corn starch. The effects of reaction temperature and time on the degree of substitution of esterified starch were studied, where the results showed that 80 °C of reaction temperature and 3h of reaction time were optimal conditions. The result of XPS testing demonstrated that the esterification reaction led to increase of ester bonds in starch. The scanning electron microscopy (SEM) and laser particle size analyzer results showed that esterification led to roughness on the surface of the starch particle, and the particle size and distribution rate of esterification starch became larger. X-ray diffraction (XRD) analysis demonstrated that esterification reaction did not change the crystalline type of native starch. The differential scanning calorimeter (DSC) and thermo gravimetric analysis (TGA) confirmed that destruction of the crystal structure resulted in improved thermoplasticity of the starch, decreased the gelatinization temperature and increased the thermogravimetric rate of esterification starch. Copyright © 2013 Elsevier B.V. All rights reserved.

  13. Sub-micronic capsules based on gelatin and poly(maleic anhydride-alt-vinyl acetate) obtained by interfacial condensation with potential biomedical applications.

    PubMed

    Iurea, Delia Mihaela; Peptu, Cătălina Anişoara; Chailan, Jean-François; Carriere, Pascal; Popa, Marcel

    2013-06-01

    New sub-micronic capsules based on a copolymer of maleic anhydride-alt-vinyl acetate and a natural polymer (gelatin) using an interfacial condensation method were obtained. Sub-micronic capsules were characterized by Fourier Transform infrared spectroscopy (FTIR), dynamic light scattering (DLS) method, zeta-potential, scanning electron microscopy (SEM) and atomic force microscopy (AFM). The thermal properties were investigated by thermogravimetric analysis (TGA). According to some parameters of the synthesis reaction (polymer weight ratio, acetone/water ratio, surfactant concentration), the mean diameter of the sub-micronic capsules can be tuned from 200 to 760 nm. The sub-micronic capsules show a higher agglomeration tendency as the amount of gelatin in their composition increases. The swelling capacity in aqueous solutions is dependent on the composition and size of the sub-micronic capsules, decreasing with their diameter and gelatin composition. The drug loading and release capacity was studied using Penicillin G (sodium salt) (PG), and it has been proved that it is influenced by the sub-micronic capsules morphology induced by preparation parameters. Encapsulation and controlled release of small molecule were successfully carried out, demonstrating the potential biomedical applications of these new easily obtained sub-micronic capsules.

  14. Transparent lithiated polymer films for thermal neutron detection

    NASA Astrophysics Data System (ADS)

    Mabe, Andrew N.; Auxier, John D.; Urffer, Matthew J.; Penumadu, Dayakar; Schweitzer, George K.; Miller, Laurence F.

    2013-09-01

    Novel water-soluble 6Li loaded copolymer scintillation films have been designed and fabricated to detect thermal neutrons. Styrene and maleic anhydride were copolymerized to form an alternating copolymer, then the anhydride functionality was hydrolyzed using 6Li hydroxide. The resulting poly(styrene-co-lithium maleate) was mixed with salicylic acid as a fluor and cast as a thin film from water. The maximum 6Li loading obtained that resulted in a transparent film was 4.36% by mass (6Li to polymer). The optimum fluorescence output was obtained for 11.7% salicylic acid by mass, presumably in the form of lithium salicylate, resulting in an optimum film containing 3.85% by mass of 6Li. A facile and robust synthesis method, film fabrication protocol, photoluminescence results, and scintillation responses are reported herein.

  15. Orientation and bonding of benzoic acid, phthalic anhydride and pyromellitic dianhydride on Cu(110)

    NASA Astrophysics Data System (ADS)

    Frederick, B. G.; Ashton, M. R.; Richardson, N. V.; Jones, T. S.

    1993-07-01

    The interaction of the polyimide precursor pyromellitic dianhydride (PMDA), and the related compounds benzoic acid and phthalic anhydride, with Cu(110) has been studied by high resolution electron energy loss spectroscopy (HREELS). For benzoic acid, deprotonation of the carboxylic acid group occurs on adsorption leading to the formation of a surface benzoate species (C 6H 5COO-). Bonding to the surface occurs through a carboxylate linkage via two equivalent oxygen atoms. The HREEL spectrum is characterised by an intense dipole active band, the symmetric OCO stretching vibration, at ˜ 1420 cm -1. The plane of the carboxylate group is aligned perpendicular to the surface as is the plane of the benzene ring. A similar species is found following exposure of Cu(110) to phthalic anhydride. The carboxylate linkage results from disruption of the anhydride ring with loss of the CO character (C 6H 4COO-). In the case of the dianhydride species PMDA, only one of the anhydride units is used in bonding to the surface; the second unit points away from the surface and is characterised by the symmetric anhydride stretch at 1255 cm -1 and weak OO stretching vibrations at ˜ 1850 cm -1. In both cases, changes in the intensity of some of the bands compared with benzoic acid suggest that the carboxylate group is tilted away from the surface normal due to an interaction between one of the carbons of the aromatic ring and the copper surface. This implies that the plane of the aromatic ring is now twisted out of the plane of the carboxylate group and, although still perpendicular to the surface, the axis is tilted to allow one of the β-carbon atoms to interact with the surface. In all cases, off-specular measurements at a primary electron energy of ˜ 8 eV are dominated by the intense CH stretching vibration. Measurements of the intensity of this mode, in the surface benzoate species, as a function of incident electron energy suggest that excitation of this mode occurs via

  16. 40 CFR 721.3635 - Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-propanediol, phosphate, anhydride with silicic acid (H4SiO4). 721.3635 Section 721.3635 Protection of..., ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4). (a) Chemical substance and... with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4) (PMN P-96-1520; CAS No. 177771-31...

  17. 40 CFR 721.3635 - Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-propanediol, phosphate, anhydride with silicic acid (H4SiO4). 721.3635 Section 721.3635 Protection of..., ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4). (a) Chemical substance and... with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4) (PMN P-96-1520; CAS No. 177771-31...

  18. Microgravity Polymers

    NASA Technical Reports Server (NTRS)

    1986-01-01

    A one-day, interactive workshop considering the effects of gravity on polymer materials science was held in Cleveland, Ohio, on May 9, 1985. Selected programmatic and technical issues were reviewed to introduce the field to workshop participants. Parallel discussions were conducted in three disciplinary working groups: polymer chemistry, polymer physics, and polymer engineering. This proceedings presents summaries of the workshop discussions and conclusions.

  19. Biodegradable Polymers

    PubMed Central

    Vroman, Isabelle; Tighzert, Lan

    2009-01-01

    Biodegradable materials are used in packaging, agriculture, medicine and other areas. In recent years there has been an increase in interest in biodegradable polymers. Two classes of biodegradable polymers can be distinguished: synthetic or natural polymers. There are polymers produced from feedstocks derived either from petroleum resources (non renewable resources) or from biological resources (renewable resources). In general natural polymers offer fewer advantages than synthetic polymers. The following review presents an overview of the different biodegradable polymers that are currently being used and their properties, as well as new developments in their synthesis and applications.

  20. Drawbacks in the use of unconventional hydrophobic anhydrides for histone derivatization in bottom-up proteomics PTM analysis

    PubMed Central

    Sidoli, Simone; Yuan, Zuo-Fei; Lin, Shu; Karch, Kelly; Wang, Xiaoshi; Bhanu, Natarajan; Arnaudo, Anna M.; Britton, Laura-Mae; Cao, Xing-Jun; Gonzales-Cope, Michelle; Han, Yumiao; Liu, Shichong; Molden, Rosalynn C.; Wein, Samuel; Afjehi-Sadat, Leila; Garcia, Benjamin A.

    2015-01-01

    Mass spectrometry (MS)-based proteomics has become the most utilized tool to characterize histone post-translational modifications (PTMs). Since histones are highly enriched in lysine and arginine residues, lysine derivatization has been developed to prevent the generation of short peptides (3-6 residues) during trypsin digestion. One of the most adopted protocols applies propionic anhydride for derivatization. However, the propionyl group is not sufficiently hydrophobic to fully retain the shortest histone peptides in reversed-phase liquid chromatography, and such procedure also hampers the discovery of natural propionylation events. In this work we tested 12 commercially available anhydrides, selected based on their safety and hydrophobicity. Performance was evaluated in terms of yield of the reaction, MS/MS fragmentation efficiency and drift in retention time by using the following samples: (i) a synthetic unmodified histone H3 tail, (ii) synthetic modified histone peptides and (iii) a histone extract from cell lysate. Results highlighted that 7 of the selected anhydrides increased peptide retention time as compared to propionic, and several anhydrides such as benzoic and valeric led to high MS/MS spectra quality. However, propionic anhydride derivatization still resulted in our opinion as the best protocol to achieve high MS sensitivity and more even ionization efficiency among the analyzed peptides. PMID:25641854

  1. Crystal structure of γ-ethyl-l-glutamate N-carb-oxy anhydride.

    PubMed

    Kanazawa, Hitoshi; Inada, Aya

    2015-01-01

    In the title compound (alternative name N-carboxy-l-glutamic anhydride γ-ethyl ester), C8H11NO5, the oxazolidine ring is essentially planar, with a maximum deviation of 0.019 (2) Å. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds between the imino group and the carbonyl O atom in the ethyl ester group, forming a tape structure along the c-axis direction. The oxazolidine rings of adjacent tapes are arranged into a layer parallel to the ac plane. This arrangement is favourable for the polymerization of the title compound in the solid state.

  2. Electrospun mats from styrene/maleic anhydride copolymers: modification with amines and assessment of antimicrobial activity.

    PubMed

    Ignatova, Milena; Stoilova, Olya; Manolova, Nevena; Markova, Nadya; Rashkov, Iliya

    2010-08-11

    New antimicrobial microfibrous electrospun mats from styrene/maleic anhydride copolymers were prepared. Two approaches were applied: (i) grafting of poly(propylene glycol) monoamine (Jeffamine® M-600) on the mats followed by formation of complex with iodine; (ii) modification of the mats with amines of 8-hydroxyquinoline or biguanide type with antimicrobial activity. Microbiological screening against S. aureus, E. coli and C. albicans revealed that both the formation of complex with iodine and the covalent attachment of 5-amino-8-hydroxyquinoline or of chlorhexidine impart high antimicrobial activity to the mats. In addition, S. aureus bacteria did not adhere to modified mats.

  3. Effect of xylene concentration of the activation energy of viscous flow for alkenylsuccinic anhydride solutions

    SciTech Connect

    Elishin, A.I.; Grichenko, A.A.

    1983-08-10

    Alkenylsuccinic anhydride (ASA) is an intermediate in the production of certain oil and fuel additives and of substances used as thickeners, desiccants, hydrophobic media, etc. Since ASA is a highly viscous liquid, a series of problems must be solved in the production and processing of oil additives in order to reduce its viscosity. This technologically urgent problem can be solved by diluting ASA with a solvent such as xylene and raising the temperature of the solution. However, how the physicochemical properties of ASA solutions depend on temperature in order to select rational temperature and dilutions must be known. ASA solutions in xylene between 20 and 150/sup 0/C were studied.

  4. Space charge behaviour in maleic anhydride grafted polyethylene/ethylene - vinyl - acetate copolymer laminates

    NASA Astrophysics Data System (ADS)

    Lee, Seung Hyung; Park, Jung Ki; Han, Jae Hong; Suh, Kwang S.

    1997-01-01

    Charge distributions in maleic anhydride (MAH) grafted polyethylene (g-PE)/ethylene - vinyl - acetate (EVA) copolymer laminates have been measured with materials of different composition. All laminates showed interfacial charge, the polarity and the magnitude of which are explained by interfacial polarization. It was found that the interfacial charge increased with the increase of MAH content in the g-PE, whereas it decreased with the increase of vinyl - acetate content in the EVA. This feature was attributed to the differences in electrical conductivity of the materials. Details of the experimental results are described.

  5. Adsorption of alkenyl succinic anhydride from solutions in carbon tetrachloride on a fine magnetite surface

    NASA Astrophysics Data System (ADS)

    Balmasova, O. V.; Ramazanova, A. G.; Korolev, V. V.

    2016-06-01

    The adsorption of alkenyl succinic anhydride from a solution in carbon tetrachloride on a fine magnetite surface at a temperature of 298.15 K is studied using fine magnetite, which forms the basis of magnetic fluids, as the adsorbent. An adsorption isotherm is recorded and interpreted in terms of the theory of the volume filling of micropores (TVFM). Adsorption process parameters are calculated on the basis of the isotherm. It is shown that at low equilibrium concentrations, the experimental adsorption isotherm is linear in the TVFM equation coordinates.

  6. The modification and characterization of maleic anhydride-styrene-methyl metacrylate terpolymer by poly(ethylene adipate)

    NASA Astrophysics Data System (ADS)

    Boztuğ, Ali; Basan, Satilmiş

    2007-03-01

    In this study, the functionality of maleic anhydride was utilized in the maleic anhydride-styrene-methyl metacrylate (MAStMMA) terpolymer. First, the polyester of poly(ethylene adipate), PEA, polycondensation copolymer was synthesized from ethylene glycol and adipic acid monomers. PEA was then modified on its maleic anhydride units in the MAStMMA terpolymer which has been synthesized previously. This modified copolymer was characterized by FTIR (Fourier Transform Infrared spectroscopy). The viscosimetric and thermomechanical characterization of MAStMMA terpolymer and its modified copolymer were also performed and the results were compared. The modified copolymer obtained was found to be more elastic and more soluble, and had lower viscosity and density.

  7. A self-crosslinking thermosetting monomer with both epoxy and anhydride groups derived from Tung oil fatty acids: Synthesis and properties

    USDA-ARS?s Scientific Manuscript database

    A self-crosslinking compound with epoxy groups and anhydride groups (GEMA) has been successfully synthesized from Tung oil fatty acid by reacting with maleic anhydride via the Diels-Alder reaction. GEMA has very good storage stability and can be cured with trace amounts of tertiary amine. This advan...

  8. A self-crosslinking thermosetting monomer with both epoxy and anhydride groups derived from tung oil fatty acids: Synthesis and properties

    USDA-ARS?s Scientific Manuscript database

    A self-crosslinking compound with epoxy groups and anhydride groups (GEMA) has been successfully synthesized from tung oil fatty acid by reacting with maleic anhydride via the Diels-Alder reaction. GEMA has very good storage stability and could be cured with trace amounts of tertiary amine. This ad...

  9. SELECTIVE HYDROGENATION OF MALEIC ANHYDRIDE TO Y-BUTYROLACTONE OVER PD/AL(2)O(3) CATALYST USING SUPERCRITICAL CO(2) AS SOLVENT

    EPA Science Inventory

    A selective hydrogenation of maleic anhydride to either y-butyrolactone or succinic anhydride over simple Pd/Al(2)O(3) catalyst under supercritical CO(2) medium is described for the first time which has considerable promise for obht lab-scale as well as industrial selective hydro...

  10. Soluble Synthetic Analogs of Malaria Pigment: Structure of Mesohematin Anhydride [FeIII(MP-IX)]2 and Solution Interaction with Chloroquine

    SciTech Connect

    D Bohle; E Dodd; A Kosar; L Sharma; P Stephens; L Suarez; D Tazoo

    2011-12-31

    Changing the vinyl groups of hematin anhydride to either ethyl or hydrogen groups results in increased solubility (Por=porphyrin). Determination of the weak binding constants of the antimalarial drug chloroquine to dimers of these hematin anhydride analogues suggests that solution-phase heme/drug interactions alone are unlikely to be the origin of the action of the drug.

  11. Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst.

    PubMed

    Shiina, Isamu; Ono, Keisuke; Nakahara, Takayoshi

    2013-11-25

    A practical protocol is developed to directly provide chiral α-acyloxyphosphonates and α-hydroxyphosphonates from (±)-α-hydroxyphosphonates utilizing the transacylation process to generate the mixed anhydrides from acid components and pivalic anhydride in the presence of organocatalysts (s-value = 33-518).

  12. Effect of reagent access on the reactivity of coals. Final report. [Maleic anhydride; dialkylmaleates

    SciTech Connect

    Larsen, J.W.

    1983-04-01

    The objective of this work is to determine the extent to which the mass transport of reagents into solid coals limits the reactivity of those coals. The purpose of task one is to determine the effect of reagent access on the acid catalyzed depolymerization of coals using phenols and/or alkyl phenyl ethers. For task two, the purpose is to determine the effect of coal swelling on its rate of reaction with a dienophile. Work on depolymerization of coals in hot, acidic phenol has been completed. The conclusion is that due to incomplete depolymerization, the complications of competing Friedel-Crafts alkylation, and the condensation reactions of the solvent, the depolymerization of coals in hot, acidic phenol is not a useful technique for solubilizing coals for structural investigations. In task two, the rate of the Diels-Alder reaction between bituminous coals and maleic anhydride was found to be diffusion controlled. The observations of simple Fickian diffusion and reaction rate constants much slower than the Diels-Alder reaction of maleic anhydride and anthracene have no other reasonable explanation than rate limiting mass transport. The diffusion rates were found to be independent of the degree of solvent swelling of the coal. In addition, the dependence of the observed rates on temperature and the size of the dienophile were measured. Results obtained using a series of dialkylmaleates are presented. Size was found to play only a small role as long as the reagent is planar. 2 tables.

  13. Dual-Functional Hydrazide-Reactive and Anhydride-Containing Oligomeric Hydrogel Building Blocks.

    PubMed

    Kascholke, Christian; Loth, Tina; Kohn-Polster, Caroline; Möller, Stephanie; Bellstedt, Peter; Schulz-Siegmund, Michaela; Schnabelrauch, Matthias; Hacker, Michael C

    2017-03-13

    Biomimetic hydrogels are advanced biomaterials that have been developed following different synthetic routes. Covalent postfabrication functionalization is a promising strategy to achieve efficient matrix modification decoupled of general material properties. To this end, dual-functional macromers were synthesized by free radical polymerization of maleic anhydride with diacetone acrylamide (N-(1,1-dimethyl-3-oxobutyl)acrylamide) and pentaerythritol diacrylate monostearate. Amphiphilic oligomers (Mn < 7.5 kDa) with anhydride contents of 7-20% offered cross-linking reactivity to yield rigid hydrogels with gelatinous peptides (E = 4-13 kPa) and good cell adhesion properties. Mildly reactive methyl ketones as second functionality remained intact during hydrogel formation and potential of covalent matrix modification was shown using hydrazide and hydrazine model compounds. Successful secondary dihydrazide cross-linking was demonstrated by an increase of hydrogel stiffness (>40%). Efficient hydrazide/hydrazine immobilization depending on solution pH, hydrogel ketone content as well as ligand concentration for bioconjugation was shown and reversibility of hydrazone formation was indicated by physiologically relevant hydrazide release over 7 days. Proof-of-concept experiments with hydrazido-functionalized hyaluronan demonstrated potential for covalent aECM immobilization. The presented dual-functional macromers have perspective as reactive hydrogel building blocks for various biomedical applications.

  14. Pomelo peel modified with acetic anhydride and styrene as new sorbents for removal of oil pollution.

    PubMed

    Chai, Wenbo; Liu, Xiaoyan; Zou, Junchen; Zhang, Xinying; Li, Beibei; Yin, Tiantian

    2015-11-05

    Pomelo peel (PP), as one of the well-known agricultural wastes, is cost-effective and environmentally friendly. Based on PP, two new kinds of oil sorbents were prepared by using acetic anhydride and styrene. The structures of raw pomelo peel (RP), acetic anhydride-treated pomelo peel (AP) and styrene-treated pomelo peel (SP) were characterized by Fourier transform infrared (FTIR) spectroscopy and scanning electron microscopy (SEM), contact-angle (CA) measurements. The optimum reaction conditions for preparation of AP and SP were also investigated. The resulting products exhibited better oil sorption capacity than that of RP for diesel and lubricating oil, also SP had better oil sorption capacity than AP, while the oil sorption capacities of SP for diesel and lubricating oil reached 18.91 and 26.36 g/g, respectively. Adsorption kinetics was well described by the pseudo-second-order model. The results indicated that AP and SP, especially SP could be used as the substitute for non-biodegradable oil sorption materials. Copyright © 2015 Elsevier Ltd. All rights reserved.

  15. Magnetic nanoparticles with functional silanes: evolution of well-defined shells from anhydride containing silane†

    PubMed Central

    Huang, Xinlei; Schmucker, Abrin; Dyke, Jason; Hall, Sara M.; Retrum, John; Stein, Barry; Remmes, Nicholas; Baxter, David V.; Dragnea, Bogdan; Bronstein, Lyudmila M.

    2009-01-01

    Modification of iron oxide nanoparticles (NPs) synthesized by high temperature solvothermal routes is carried out using two silanes: (i) N-(6-aminohexyl)-aminopropyltrimethoxysilane (AHAPS) where only one end of the molecule reacts with the surface Fe-OH groups and (ii) 3-(triethoxysilyl)propylsuccinic anhydride (SSA) where both ends are reactive with Fe-OH. Depending on the NP synthesis protocol, the amount of surface OH groups on the NPs may differ, however, for all the cases presented here, the comparatively low OH group density prevents a high density of AHAPS coverage, yielding NP aggregates instead of single particles in aqueous solutions. Alternatively, use of SSA containing two terminal functionalities, anhydride and siloxy, which are both reactive towards the NP surface, results in the formation of discrete dense polymeric shells, providing stability of individual NPs in water. The mechanism of the SSA shell formation is discussed. The evolution of the chemical transformations leads to shells of different thickness and density, yet this evolution can be halted by hydrolysis, after which the NPs are water soluble, negatively charged and exhibit excellent stability in aqueous media. PMID:19763240

  16. Catalytic behavior of Sn/Bi metal powder in anhydride-based epoxy curing.

    PubMed

    Jang, Keon-Soo; Eom, Yong-Sung; Moon, Jong-Tae; Oh, Yong-Soo; Nam, Jae-Do

    2009-12-01

    In this paper, we report the catalytic activity of the Sn/Bi alloy beads and its acceleration of the exothermic epoxy curing reactions in various thermal conditions and bead compositions. As being used as low-melting solder balls in electronic interconnection processes with various epoxy systems, it was found that the Sn/Bi beads substantially lowered the exothermic peak temperature of the diglycidyl ether of bisphenol A (DGEBA)/anhydride systems in up to ca. 140 degrees C depending on different types of anhydride curing agents. The catalytic activation of Sn/Bi powder was initiated with a small amount of Sn/Bi powder, for example, lowering ca. 50 degrees C of the exothermic peak temperature by adding only 0.1 vol% of Sn/Bi powder. The catalytic capability of the powder was increased by using smaller sized beads corresponding to larger catalytic surface area at the same volume fraction. Exhibiting a latent catalytic effect, the catalytic activity of Sn/Bi powder was remained latent at temperatures lower than 100 degrees C in isothermal conditions.

  17. Flexible Polyimide Aerogel Cross-linked by Poly(maleic Anhydride-alt-alkylene)

    NASA Technical Reports Server (NTRS)

    Guo, Haiquan; Meador, Mary Ann B.; Wilkewitz, Brittany Marie

    2014-01-01

    Aerogels are potential materials for aerospace applications due to their lower thermal conductivity, lighter weight, and low dielectric constant. However, silica aerogels are restricted due to their inherent fragility, hygroscopic nature, and poor mechanical properties, especially in extreme aerospace environments. In order to fit the needs of aerospace applications, developing new thermal insulation materials that are flexible, and moisture resistant is needed. To this end, we fabricated a series of polyimide aerogels crosslinked with different poly(maleic anhydride-alt-alkylene)s as seen in Scheme 1. The polyimide oligomers were made with 3,3,4,4-biphenyltetracarboxylic dianhydride (BPDA), and different diamines or diamine combinations. The resulting aerogels have low density (0.06 gcm3 to 0.16 gcm3) and high surface area (240-440 m2g). The effect of the different backbone structures on density, shrinkage, porosity, surface area, mechanical properties, moisture resistance and thermal properties will be discussed. These novel polyalkylene-imide aerogels may be potential candidates for applications such as space suit insulation for planetary surface missions, insulation for inflatable structures for habitats, inflatable aerodynamic decelerators for entry, descent and landing (EDL) operations, and cryotank insulation for advance space propulsion systems. Scheme 1. Network of polyimide aerogels crosslinked with deifferent poly(maleic anhydride).

  18. Preparation, characterization and antibacterial activity of octenyl succinic anhydride modified inulin.

    PubMed

    Zhang, Xiaoyun; Zhang, Ye-Wang; Zhang, Hongyin; Yang, Qiya; Wang, Haiying; Zhang, Guochao

    2015-01-01

    Octenyl succinic anhydride modified inulin (In-OSA) was synthesized via chemical modification of inulin with octenyl succinic anhydride (OSA). The esterification of inulin with OSA was confirmed by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), and degree of substitution (DS) calculation. Antibacterial activity of In-OSA against Staphylococcus aureus and Escherichia coli was investigated by minimum inhibitory concentration (MIC) and inhibition rate determination. The results showed that inhibition rates against both E.coli and S. aureus increased with the increase of the In-OSA concentration. And the MICs against E. coli and S. aureus were 1% and 0.5% (w/v), respectively. The antibacterial mechanism was analyzed with the results of the proteins and nucleic acids leakage, SEM and negative staining transmission electron microscopy (TEM). Both the leakages of proteins and nucleic acids increased with the increase of the In-OSA concentration. The leakage occurred mainly in the early stage which indicated that cell membrane and wall were destroyed by In-OSA quickly. The images of SEM and negative staining TEM suggested that the cell membranes and cell walls of S. aureus were damaged more severely and even destroyed completely; but only pores appeared on the surface of E. coli.

  19. Efficient photochemical generation of peroxycarboxylic nitric anhydrides with ultraviolet light-emitting diodes

    NASA Astrophysics Data System (ADS)

    Rider, N. D.; Taha, Y. M.; Odame-Ankrah, C. A.; Huo, J. A.; Tokarek, T. W.; Cairns, E.; Moussa, S. G.; Liggio, J.; Osthoff, H. D.

    2015-07-01

    Photochemical sources of peroxycarboxylic nitric anhydrides (PANs) are utilized in many atmospheric measurement techniques for calibration or to deliver an internal standard. Conventionally, such sources rely on phosphor-coated low-pressure mercury (Hg) lamps to generate the UV light necessary to photo-dissociate a dialkyl ketone (usually acetone) in the presence of a calibrated amount of nitric oxide (NO) and oxygen (O2). In this manuscript, a photochemical PAN source in which the Hg lamp has been replaced by arrays of ultraviolet light-emitting diodes (UV-LEDs) is described. The output of the UV-LED source was analyzed by gas chromatography (PAN-GC) and thermal dissociation cavity ring-down spectroscopy (TD-CRDS). Using acetone, diethyl ketone (DIEK), diisopropyl ketone (DIPK), or di-n-propyl ketone (DNPK), respectively, the source produces peroxyacetic (PAN), peroxypropionic (PPN), peroxyisobutanoic (PiBN), or peroxy-n-butanoic nitric anhydride (PnBN) from NO in high yield (> 90 %). Box model simulations with a subset of the Master Chemical Mechanism (MCM) were carried out to rationalize product yields and to identify side products. The present work demonstrates that UV-LED arrays are a viable alternative to current Hg lamp setups.

  20. A novel reactive processing technique: using telechelic polymers to reactively compatibilize polymer blends

    SciTech Connect

    Ashcraft, Earl C; Ji, Haining; Mays, Jimmy; Dadmun, Mark D

    2009-01-01

    Difunctional reactive polymers, telechelics, were used to reactively form multiblock copolymers in situ when melt-blended with a blend of polystyrene and polyisoprene. To quantify the ability of the copolymer to compatibilize the blends, the time evolution of the domain size upon annealing was analyzed by SEM. It was found that the most effective parameter to quantify the ability of the copolymer to inhibit droplet coalescence is Kreltstable, the relative coarsening constant multiplied by the stabilization time. These results indicate that intermediate-molecular-weight telechelic pairs of both highly reactive Anhydride-PS-Anhydride/NH2-PI-NH2 and slower reacting Epoxy-PS-Epoxy/COOH-PI-COOH both effectively suppress coalescence, with the optimal molecular weight being slightly above the critical molecular weight of the homopolymer,Mc. The effects of telechelic loading were also investigated, where the optimal loading concentration for this system was 0.5 wt %, as higher concentrations exhibited a plasticizing effect due to the presence of unreacted low-molecular-weight telechelics present in the blend. A determination of the interfacial coverage of the copolymer shows that a conversion of 1.5-3.0% was required for 20% surface coverage at 5.0 wt % telechelic loading, indicating a large excess of telechelics in this system. At the optimal loading level of 0.5 wt %, a conversion of 15% was required for 20% surface coverage. The results of these experiments provide a clear understanding of the role of telechelic loading and molecular weight on its ability to reactively form interfacial modifiers in phase-separated polymer blends and provide guidelines for the development of similar reactive processing schemes that can use telechelic polymers to reactively compatibilize a broad range of polymer blends.

  1. Preparation and characterization of poly(methyl methacrylate) and poly(maleic anhydride-co-diallyl phthalate) grafted carbon black through γ-ray irradiation

    NASA Astrophysics Data System (ADS)

    Bo, Yang; Cui, Jiayang; Cai, Yangben; Xu, Shiai

    2016-02-01

    In this study, the grafting polymerization of methyl methacrylate (MMA) monomer and maleic anhydride/diallyl phthalate (MAH/DAP) co-monomer onto the surface of carbon black (CB) were carried out at room temperature and normal pressure by γ-ray irradiation. The surface chemistry of grafted CBs were characterized by infrared spectroscopy (IR), thermo-gravimetric analysis (TGA) and X-ray photoelectron spectroscopy (XPS). The results show that there are some remanent polymers on the surface of modified CBs after extract for 48 h, indicating that poly(methyl methacrylate) (PMMA) and poly(MAH-co-DAP) have been successfully grafted onto the surface of CB without using initiator due to the high energy of γ-ray irradiation. Dynamic light scattering (DLS), scanning electron microscopy (SEM) and transmission electron microscopy (TEM) reveal that the grafted CBs have smaller average aggregate size and better dispersibility than that of CB in absolute ethanol. In addition, it was found that the amount of oxygen groups and the irradiation doses/dose rates have little effect on the grafting degree of CB.

  2. Preparation and characterization of mucoadhesive nanoparticles of poly (methyl vinyl ether-co-maleic anhydride) containing glycyrrhizic acid intended for vaginal administration.

    PubMed

    Aguilar-Rosas, Irene; Alcalá-Alcalá, Sergio; Llera-Rojas, Viridiana; Ganem-Rondero, Adriana

    2015-01-01

    Traditional vaginal preparations reside in the vaginal cavity for relatively a short period of time, requiring multiple doses in order to attain the desired therapeutic effect. Therefore, mucoadhesive systems appear to be appropriate to prolong the residence time in the vaginal cavity. In the current study, mucoadhesive nanoparticles based on poly(methyl vinyl ether-co-maleic anhydride) (PVM/MA) intended for vaginal delivery of glycyrrhizic acid (GA) (a drug with well-known antiviral properties) were prepared and characterized. Nanoparticles were generated by a solvent displacement method. Incorporation of GA was performed during nanoprecipitation, followed by adsorption of drug once nanoparticles were formed. The prepared nanoparticles were characterized in terms of size, Z-potential, morphology, drug loading, interaction of GA with PVM/MA (by differential scanning calorimetry) and the in vitro interaction of nanoparticles with pig mucin (at two pH values, 3.6 and 5; with and without GA adsorbed). The preparation method led to nanoparticles of a mean diameter of 198.5 ± 24.3 nm, zeta potential of -44.8 ± 2.8 mV and drug loading of 15.07 ± 0.86 µg/mg polymer. The highest mucin interaction resulted at pH 3.6 for nanoparticles without GA adsorbed. The data obtained suggest the promise of using mucoadhesive nanoparticles of PVM/MA for intravaginal delivery of GA.

  3. Piezoelectric Polymers

    NASA Technical Reports Server (NTRS)

    Harrison, J. S.; Ounaies, Z.; Bushnell, Dennis M. (Technical Monitor)

    2001-01-01

    The purpose of this review is to detail the current theoretical understanding of the origin of piezoelectric and ferroelectric phenomena in polymers; to present the state-of-the-art in piezoelectric polymers and emerging material systems that exhibit promising properties; and to discuss key characterization methods, fundamental modeling approaches, and applications of piezoelectric polymers. Piezoelectric polymers have been known to exist for more than forty years, but in recent years they have gained notoriety as a valuable class of smart materials.

  4. "Graft-to" Protein/Polymer Conjugates Using Polynorbornene Block Copolymers.

    PubMed

    Isarov, Sergey A; Lee, Parker W; Pokorski, Jonathan K

    2016-02-08

    A series of water-soluble polynorbornene block copolymers prepared via Ring-Opening Metathesis Polymerization (ROMP) were grafted to proteins to form ROMP-derived bioconjugates. ROMP afforded low-dispersity polymers and allowed for strict control over polymer molecular weight and architecture. The polymers consisted of a large block of PEGylated monoester norbornene and were capped with a short block of norbornene dicarboxylic anhydride. This cap served as a reactive linker that facilitated attachment of the polymer to lysine residues under mildly alkaline conditions. The generality of this approach was shown by synthesizing multivalent polynorbornene-modified viral nanoparticles derived from bacteriophage Qβ, a protein nanoparticle used extensively for nanomedicine. The conjugated nanoparticles showed no cytotoxicity to NIH 3T3 murine fibroblast cells. These findings establish protein bioconjugation with functionalized polynorbornenes as an effective alternative to conventional protein/polymer modification strategies and further expand the toolbox for protein bioconjugates.

  5. Copolymerization and terpolymerization of carbon dioxide/propylene oxide/phthalic anhydride using a (salen)Co(III) complex tethering four quaternary ammonium salts

    PubMed Central

    Jeon, Jong Yeob; Eo, Seong Chan; Varghese, Jobi Kodiyan

    2014-01-01

    Summary The (salen)Co(III) complex 1 tethering four quaternary ammonium salts, which is a highly active catalyst in CO2/epoxide copolymerizations, shows high activity for propylene oxide/phthalic anhydride (PO/PA) copolymerizations and PO/CO2/PA terpolymerizations. In the PO/PA copolymerizations, full conversion of PA was achieved within 5 h, and strictly alternating copolymers of poly(1,2-propylene phthalate)s were afforded without any formation of ether linkages. In the PO/CO2/PA terpolymerizations, full conversion of PA was also achieved within 4 h. The resulting polymers were gradient poly(1,2-propylene carbonate-co-phthalate)s because of the drift in the PA concentration during the terpolymerization. Both polymerizations showed immortal polymerization character; therefore, the molecular weights were determined by the activity (g/mol-1) and the number of chain-growing sites per 1 [anions in 1 (5) + water (present as impurity) + ethanol (deliberately fed)], and the molecular weight distributions were narrow (M w/M n, 1.05–1.5). Because of the extremely high activity of 1, high-molecular-weight polymers were generated (M n up to 170,000 and 350,000 for the PO/PA copolymerization and PO/CO2/PA terpolymerization, respectively). The terpolymers bearing a substantial number of PA units (f PA, 0.23) showed a higher glass-transition temperature (48 °C) than the CO2/PO alternating copolymer (40 °C). PMID:25161738

  6. Releasable Conjugation of Polymers to Proteins.

    PubMed

    Gong, Yuhui; Leroux, Jean-Christophe; Gauthier, Marc A

    2015-07-15

    Many synthetic strategies are available for preparing well-defined conjugates of peptides/proteins and polymers. Most reports on this topic involve coupling methoxy poly(ethylene glycol) to therapeutic proteins, a process referred to as PEGylation, to increase their circulation lifetime and reduce their immunogenicity. Unfortunately, the major dissuading dogma of PEGylation is that, in many cases, polymer modification leads to significant (or total) loss of activity/function. One approach that is gaining momentum to address this challenge is to release the native protein from the polymer with time in the body (releasable PEGylation). This contribution will present the state-of-the-art of this rapidly evolving field, with emphasis on the chemistry behind the release of the peptide/protein and the means for altering the rate of release in biological fluids. Linkers discussed include those based on the following: substituted maleic anhydride and succinates, disulfides, 1,6-benzyl-elimination, host-guest interactions, bicin, β-elimination, biodegradable polymers, E1cb elimination, β-alanine, photoimmolation, coordination chemistry, zymogen activation, proteolysis, and thioesters.

  7. Silver-containing polymer composition used in spacecraft and semiconductor optoelectronics control systems

    NASA Astrophysics Data System (ADS)

    Ivanov, A. A.; Tuev, V. I.

    2015-10-01

    The copolymer of the vinyl chloride-maleic anhydride and silver nano- and microparticle (70 wt %) composition is offered as a conductive adhesive for fixing various chips on the dielectric substrate. The wiring volume resistivity is up to 3.1×10-8 Ohm×m. The adhesive strength of the silver-containing polymer composition (70% of Ag) applied under a shear on the dielectric substrate is 106 N/mm2. Adhesive layers obtained from these substances have a high thermal conductivity up to λ = 199.93 W/m×K that depends on the amount of Ag in the polymer composition.

  8. Silver-containing polymer composition used in spacecraft and semiconductor optoelectronics control systems

    SciTech Connect

    Ivanov, A. A. Tuev, V. I.

    2015-10-27

    The copolymer of the vinyl chloride-maleic anhydride and silver nano- and microparticle (70 wt %) composition is offered as a conductive adhesive for fixing various chips on the dielectric substrate. The wiring volume resistivity is up to 3.1×10{sup −8} Ohm×m. The adhesive strength of the silver-containing polymer composition (70% of Ag) applied under a shear on the dielectric substrate is 106 N/mm{sup 2}. Adhesive layers obtained from these substances have a high thermal conductivity up to λ = 199.93 W/m×K that depends on the amount of Ag in the polymer composition.

  9. Perfluorosulfonic acid membrane catalysts for optical sensing of anhydrides in the gas phase.

    PubMed

    Ayyadurai, Subasri M; Worrall, Adam D; Bernstein, Jonathan A; Angelopoulos, Anastasios P

    2010-07-15

    Continuous, on-site monitoring of personal exposure levels to occupational chemical hazards in ambient air is a long-standing analytical challenge. Such monitoring is required to institute appropriate health measures but is often limited by the time delays associated with batch air sampling and the need for off-site instrumental analyses. In this work, we report on the first attempt to use the catalytic properties of perfluorosulfonic acid (PSA) membranes to obtain a rapid, selective, and highly sensitive optical response to trimellitic anhydride (TMA) in the gas phase for portable sensor device application. TMA is used as starting material for various organic products and is recognized to be an extremely toxic agent by the National Institute for Occupational Safety and Health (NIOSH). Resorcinol dye is shown to become immobilized in PSA membranes and diffusionally constrain an orange brown product that results from acid-catalyzed reaction with more rapidly diffusing TMA molecules. FTIR, UV/vis, reaction selectivity to TMA versus trimellitic acid (TMLA), and homogeneous synthesis are used to infer 5,7- dihydroxyanthraquinone-2-carboxylic acid as the acylation product of the reaction. The color response has a sensitivity to at least 3 parts per billion (ppb) TMA exposure and, in addition to TMLA, excludes maleic anhydride (MA) and phthalic anhydride (PA). Solvent extraction at long times is used to determine that the resorcinol extinction coefficient in 1100 EW PSA membrane has a value of 1210 m(2)/g at 271.01 nm versus a value of 2010 m(2)/g at 275.22 nm in 50 vol% ethanol/water solution. The hypsochromic wavelength shift and reduced extinction coefficient suggest that the polar perfluorosulfonic acid groups in the membrane provide the thermodynamic driving force for diffusion and immobilization. At a resorcinol concentration of 0.376 g/L in the membrane, a partition coefficient of nearly unity is obtained between the membrane and solution concentrations and a

  10. Evolutionary importance of the intramolecular pathways of hydrolysis of phosphate ester mixed anhydrides with amino acids and peptides.

    PubMed

    Liu, Ziwei; Beaufils, Damien; Rossi, Jean-Christophe; Pascal, Robert

    2014-12-11

    Aminoacyl adenylates (aa-AMPs) constitute essential intermediates of protein biosynthesis. Their polymerization in aqueous solution has often been claimed as a potential route to abiotic peptides in spite of a highly efficient CO2-promoted pathway of hydrolysis. Here we investigate the efficiency and relevance of this frequently overlooked pathway from model amino acid phosphate mixed anhydrides including aa-AMPs. Its predominance was demonstrated at CO2 concentrations matching that of physiological fluids or that of the present-day ocean, making a direct polymerization pathway unlikely. By contrast, the occurrence of the CO2-promoted pathway was observed to increase the efficiency of peptide bond formation owing to the high reactivity of the N-carboxyanhydride (NCA) intermediate. Even considering CO2 concentrations in early Earth liquid environments equivalent to present levels, mixed anhydrides would have polymerized predominantly through NCAs. The issue of a potential involvement of NCAs as biochemical metabolites could even be raised. The formation of peptide-phosphate mixed anhydrides from 5(4H)-oxazolones (transiently formed through prebiotically relevant peptide activation pathways) was also observed as well as the occurrence of the reverse cyclization process in the reactions of these mixed anhydrides. These processes constitute the core of a reaction network that could potentially have evolved towards the emergence of translation.

  11. Kinetics of Hydrolysis of Acetic Anhydride by In-Situ FTIR Spectroscopy: An Experiment for the Undergraduate Laboratory

    ERIC Educational Resources Information Center

    Haji, Shaker; Erkey, Can

    2005-01-01

    A reaction kinetics experiment for the chemical engineering undergraduate laboratory course was developed in which in-situ Fourier Transfer Infrared spectroscopy was used to measure reactant and product concentrations. The kinetics of the hydrolysis of acetic anhydride was determined by experiments carried out in a batch reactor. The results…

  12. Aggregate structure and effect of phthalic anhydride modified soy protein on the mechanical properties of styrene-butadiene copolymer

    USDA-ARS?s Scientific Manuscript database

    The aggregate structure of phthalic anhydride (PA) modified soy protein isolate (SPI) was investigated by estimating its fractal dimension from the equilibrated dynamic strain sweep experiments. The estimated fractal dimensions of the filler aggregates were less than 2, indicating that these partic...

  13. Anhydride formation is not a valid mechanism for peptide cleavage by carboxypeptidase-A: a semiempirical reaction pathway study

    NASA Astrophysics Data System (ADS)

    Vardi-Kilshtain, Alexandra; Shoham, Gil; Goldblum, Amiram

    The mechanism of action of zinc metalloproteinases has been studied by following the direct nucleophilic pathway, which has been frequently suggested but not yet examined by computational methods, and comparing it to other pathways. We computed the reaction enthalpies for the direct nucleophilic attack by Glu270 in the active site model of carboxypeptidase-A on a model substrate's peptide carbonyl and followed this pathway through mixed anhydride formation and subsequent anhydride cleavage by water. The starting molecular coordinates originate in our own high-resolution crystal structure and the computations have been conducted with the minimal neglect of differential overlap (MNDO) Hamiltonian, modified to include the d-orbitals of zinc and the effects of multiple hydrogen bonding, thus labelled MNDO/d/H. Compared to our recent results for two other candidate pathways for this mechanism, both of the General-Acid-General-Base type, we conclude that the direct nucleophilic or 'anhydride' pathway has a much higher energy barrier at the rate determining step, which is a proton transfer, than previously calculated paths. We argue that the 'anhydride' pathway is thus not a valid one for the cleavage of peptides by carboxypeptidase-A.

  14. RAFT copolymerization of itaconic anhydride and 2-methoxyethyl acrylate: a multifunctional scaffold for preparation of "clickable" gold nanoparticles.

    PubMed

    Javakhishvili, Irakli; Kasama, Takeshi; Jankova, Katja; Hvilsted, Søren

    2013-05-25

    RAFT copolymerization of 2-methoxyethyl acrylate and itaconic anhydride - a monomer derived from renewable resources - is carried out in a controlled fashion. The copolymer allows preparation of gold nanoparticles with abundant surficial carboxyl and alkyne functional groups that are dendronized via Cu(I)-mediated "click" reaction.

  15. Evolutionary Importance of the Intramolecular Pathways of Hydrolysis of Phosphate Ester Mixed Anhydrides with Amino Acids and Peptides

    PubMed Central

    Liu, Ziwei; Beaufils, Damien; Rossi, Jean-Christophe; Pascal, Robert

    2014-01-01

    Aminoacyl adenylates (aa-AMPs) constitute essential intermediates of protein biosynthesis. Their polymerization in aqueous solution has often been claimed as a potential route to abiotic peptides in spite of a highly efficient CO2-promoted pathway of hydrolysis. Here we investigate the efficiency and relevance of this frequently overlooked pathway from model amino acid phosphate mixed anhydrides including aa-AMPs. Its predominance was demonstrated at CO2 concentrations matching that of physiological fluids or that of the present-day ocean, making a direct polymerization pathway unlikely. By contrast, the occurrence of the CO2-promoted pathway was observed to increase the efficiency of peptide bond formation owing to the high reactivity of the N-carboxyanhydride (NCA) intermediate. Even considering CO2 concentrations in early Earth liquid environments equivalent to present levels, mixed anhydrides would have polymerized predominantly through NCAs. The issue of a potential involvement of NCAs as biochemical metabolites could even be raised. The formation of peptide–phosphate mixed anhydrides from 5(4H)-oxazolones (transiently formed through prebiotically relevant peptide activation pathways) was also observed as well as the occurrence of the reverse cyclization process in the reactions of these mixed anhydrides. These processes constitute the core of a reaction network that could potentially have evolved towards the emergence of translation. PMID:25501391

  16. Evolutionary Importance of the Intramolecular Pathways of Hydrolysis of Phosphate Ester Mixed Anhydrides with Amino Acids and Peptides

    NASA Astrophysics Data System (ADS)

    Liu, Ziwei; Beaufils, Damien; Rossi, Jean-Christophe; Pascal, Robert

    2014-12-01

    Aminoacyl adenylates (aa-AMPs) constitute essential intermediates of protein biosynthesis. Their polymerization in aqueous solution has often been claimed as a potential route to abiotic peptides in spite of a highly efficient CO2-promoted pathway of hydrolysis. Here we investigate the efficiency and relevance of this frequently overlooked pathway from model amino acid phosphate mixed anhydrides including aa-AMPs. Its predominance was demonstrated at CO2 concentrations matching that of physiological fluids or that of the present-day ocean, making a direct polymerization pathway unlikely. By contrast, the occurrence of the CO2-promoted pathway was observed to increase the efficiency of peptide bond formation owing to the high reactivity of the N-carboxyanhydride (NCA) intermediate. Even considering CO2 concentrations in early Earth liquid environments equivalent to present levels, mixed anhydrides would have polymerized predominantly through NCAs. The issue of a potential involvement of NCAs as biochemical metabolites could even be raised. The formation of peptide-phosphate mixed anhydrides from 5(4H)-oxazolones (transiently formed through prebiotically relevant peptide activation pathways) was also observed as well as the occurrence of the reverse cyclization process in the reactions of these mixed anhydrides. These processes constitute the core of a reaction network that could potentially have evolved towards the emergence of translation.

  17. Improving grafting efficiency of dicarboxylic anhydride monomer on polylactic acid by manipulating monomer structure and using comonomer and reducing agent

    USDA-ARS?s Scientific Manuscript database

    Maleic anhydride (MA) grafted polylactic acid (PLA) acting as reactive compatibilizer for PLA blends and composites has been reported. However, melt free-radical grafting of MA on PLA is often subject to steric and electron effects of the substituents in the monomer and low initiation efficiency, yi...

  18. Kinetics of Hydrolysis of Acetic Anhydride by In-Situ FTIR Spectroscopy: An Experiment for the Undergraduate Laboratory

    ERIC Educational Resources Information Center

    Haji, Shaker; Erkey, Can

    2005-01-01

    A reaction kinetics experiment for the chemical engineering undergraduate laboratory course was developed in which in-situ Fourier Transfer Infrared spectroscopy was used to measure reactant and product concentrations. The kinetics of the hydrolysis of acetic anhydride was determined by experiments carried out in a batch reactor. The results…

  19. Preventing false-negatives in the in vitro skin sensitization testing of acid anhydrides using interleukin-8 release assays.

    PubMed

    Narita, Kazuto; Vo, Phuc Thi Hong; Yamamoto, Kenta; Kojima, Hajime; Itagaki, Hiroshi

    2017-04-11

    In vitro safety tests may be used as replacements for animal tests owing to their accuracy and high-throughput performance. However, several in vitro skin sensitization tests produce false-negative results such as acid anhydride. Here, we investigated the relationship between false-negative results of acid anhydride and its hydrolysis by aqueous vehicle. Differences in the pattern of hydrolysis for phthalic anhydride (PAH) due to addition of 1 drop of stock solution of PAH in liquid paraffin (LP) dispersion medium and PAH in DMSO were analyzed in a cell-free system. The results showed that use of LP dispersion medium stabilized the concentration of PAH in water over 5min by sustained-release, although almost all PAH converted to phthalic acid in water within 5min using DMSO. Additionally, treatment of THP-1 cells with PAH and phthalic acid using LP dispersion medium for 5min resulted in a 32-fold increase in IL-8 release for PAH as compared with that in the vehicle control. In contrast, for PAH using aqueous vehicle and phthalic acid using LP dispersion medium, there were no significant increases in IL-8 release. Similarly, using LP dispersion medium, trimellitic anhydride significantly increased IL-8 release was observed.

  20. Tetrahydrophthalic Anhydrides as Addition Curing Polyimide End Caps: Thermal Isomerization of Methylendianiline 3,6-Diphenyltetrahydrophthalic Bisimides

    NASA Technical Reports Server (NTRS)

    Frimer, Aryeh A.; Gilinsky-Sharon, Pessia; Gottlieb, Hugo E.; Meador, Mary Ann B.; Johnston, J. Christopher

    2005-01-01

    In depth NMR studies confirm that heating a 1:2 mixture of cis, cis, cis 3,6-diphenyltetrahydrophthalic anhydride (end cap 9c) with methylenedianiline at 316 C initially yields the corresponding highly congested cis, cis, cis 3,6-diphenyltetrahydrophthalic bisimide 11, which is converted at this temperature to the observed product, the less hindered trans, cis, trans isomer 12.

  1. Organocatalytic Lewis base functionalisation of carboxylic acids, esters and anhydrides via C1-ammonium or azolium enolates.

    PubMed

    Morrill, Louis C; Smith, Andrew D

    2014-09-07

    This tutorial review highlights the organocatalytic Lewis base functionalisation of carboxylic acids, esters and anhydrides via C1-ammonium/azolium enolates. The generation and synthetic utility of these powerful intermediates is highlighted through their application in various methodologies including aldol-lactonisations, Michael-lactonisations/lactamisations and [2,3]-rearrangements.

  2. Efficient Diacetoxylation of Alkenes via Pd(II)/Pd(IV) Process with Peracetic Acid and Acetic Anhydride

    PubMed Central

    Park, Chan Pil; Lee, Joo Ho; Yoo, Kyung Soo; Jung, Kyung Woon

    2010-01-01

    A palladium-catalyzed diacetoxylation of alkenes in the presence of peracetic acid and acetic anhydride was developed to produce diacetates efficiently and diastereoselectively. Due to its mild conditions, this method was suitable for a broad range of substrates encompassing conjugated and non-conjugated olefins. PMID:20455553

  3. Effects of Amine and Anhydride Curing Agents on the VARTM Matrix Processing Properties

    NASA Technical Reports Server (NTRS)

    Grimsley, Brian W.; Hubert, Pascal; Song, Xiaolan; Cano, Roberto J.; Loos, Alfred C.; Pipes, R. Byron

    2002-01-01

    To ensure successful application of composite structure for aerospace vehicles, it is necessary to develop material systems that meet a variety of requirements. The industry has recently developed a number of low-viscosity epoxy resins to meet the processing requirements associated with vacuum assisted resin transfer molding (VARTM) of aerospace components. The curing kinetics and viscosity of two of these resins, an amine-cured epoxy system, Applied Poleramic, Inc. VR-56-4 1, and an anhydride-cured epoxy system, A.T.A.R.D. Laboratories SI-ZG-5A, have been characterized for application in the VARTM process. Simulations were carried out using the process model, COMPRO, to examine heat transfer, curing kinetics and viscosity for different panel thicknesses and cure cycles. Results of these simulations indicate that the two resins have significantly different curing behaviors and flow characteristics.

  4. Physico-mechanical properties of silanized-montmorillonite reinforced chitosan-co-poly(maleic anhydride) composites

    NASA Astrophysics Data System (ADS)

    Saputra, O. A.; Fajrin, A.; Nauqinida, M.; Suryanti, V.; Pramono, E.

    2017-07-01

    To solve the problems of dependence on petroleum as starting material in the manufacturing of plastics in Indonesia, green plastic from biopolymer like chitosan to be one of promising options and alternative to replace the conventional plastics. However, to overcome the mechanical and physical properties of chitosan, the addition of reinforcement agent was introduced. In this study, silanized-montmorillonite (sMMt) has been prepared as a reinforcement agent in the chitosan-co-poly(maleic anhydride) (referred as Cs-MAH) matrix. Silanizing of montmorillonite is one of strategy to improve the interaction between montmorillonite and chitosan, consequently, the mechanical properties, tensile strength of composites contained 6 phr of sMMt improved 56.5% to chitosan. Moreover, the presence both MAH and sMMt on the comosites also reduced swelling degree and swelling area by 20.6% and 26.7%.

  5. Crystal structure of O-benzyl-l-tyrosine N-carb-oxy anhydride.

    PubMed

    Inada, Aya; Kanazawa, Hitoshi

    2017-04-01

    In the title compound, C17H15NO4 (alternative name; O-benzyl-l-tyrosine N-carb-oxy anhydride), the oxazolidine ring is planer, with an r.m.s. deviation of 0.039 Å. The benz-yloxy and benzyl rings are almost coplanar, making a dihedral angle of 0.078 (10)°, and are inclined to the oxazolidine ring by 59.16 (11) and 58.42 (11)°, respectively. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming ribbons propagating along [010]. The ribbons are linked by C-H⋯π inter-actions, forming a three-dimensional supra-molecular structure. The oxazolidine rings of adjacent ribbons are arranged into a layer parallel to the ab plane. This arrangement is favourable for the polymerization of the compound in the solid state.

  6. Synthesis and paste properties of octenyl succinic anhydride modified early Indica rice starch.

    PubMed

    Song, Xiao-yan; Chen, Qi-he; Ruan, Hui; He, Guo-qing; Xu, Qiong

    2006-10-01

    Octenyl succinic anhydride (OSA) modified early Indica rice starch was prepared in aqueous slurry systems using response surface methodology. The paste properties of the OSA starch were also investigated. Results indicated that the suitable parameters for the preparation of OSA starch from early Indica rice starch were as follows: reaction period 4 h, reaction temperature 33.4 degrees C, pH of reaction system 8.4, concentration of starch slurry 36.8% (in proportion to water, w/w), amount of OSA 3% (in proportion to starch, w/w). The degree of substitution was 0.0188 and the reaction efficiency was 81.0%. The results of paste properties showed that with increased OSA modification, the starch derivatives had higher paste clarity, decreased retrogradation and better freeze-thaw stability.

  7. Effects of hydrothermal pretreatment on subsequent octenylsuccinic anhydride (OSA) modification of cornstarch.

    PubMed

    Chen, Xu; He, Xiaowei; Huang, Qiang

    2014-01-30

    Cornstarch granules were hydrothermally pretreated and then esterified with octenylsuccinic anhydride (OSA). The physicochemical properties of cornstarch and hydrothermally pretreated OS-starch (H-OS-starch) were investigated. Results showed that hydrothermal pretreatments significantly increased the degree of substitution (DS) and reaction efficiency (RE) of H-OS-starch compared with the control. The higher the pretreatment temperature was, the more the OSA could go deep into the internal starch granules. The optimal pretreatment temperature for the OSA modification was 60°C. In addition, the OS groups appeared to be distributed throughout the OS-starch granules, especially on the surface, as shown by confocal laser scanning microscopy (CLSM). H-OS-starch had a slightly higher peak viscosity (Pv) and break down (BD) values, but lower pasting temperature (Tp) compared with the control OS-starch.

  8. Enhanced Activity of Nanocrystalline Beta Zeolite for Acylation of Veratrole with Acetic Anhydride.

    PubMed

    Aisha Mahmood Abdulkareem, Al-Turkustani; Selvin, Rosilda

    2016-04-01

    Friedel-Craft acylation of veratrole using homogeneous acid catalysts such as AlCl3, FeCl3, ZnCl2, and HF etc. produces acetoveratrone, (3',4'-dimethoxyacetophenone), which is the intermediate for synthesis of papavarine alkaloids. The problems associated with these homogeneous catalysts can be overcome by using heterogeneous solid catalysts. Since acetoveratrone is a larger molecule, large pore Beta zeolites with smaller particle sizes are beneficial for the liquid-phase acylation of veratrole, for easy diffusion of reactants and products. The present study aims in the acylation of veratrole with acetic anhydride using nanocrystalline Beta Zeolite catalyst. A systematic investigation of the effects of various reaction parameters was done. The catalysts were characterized for their structural features by using XRD, TEM and DLS analyses. The catalytic activity of nanocrystalline Beta zeolite was compared with commercial Beta zeolite for the acylation and was found that nanocrystalline Beta zeolite possessed superior activity.

  9. Mechanism of highly improved electrical properties in polypropylene by chemical modification of grafting maleic anhydride

    NASA Astrophysics Data System (ADS)

    Zhou, Yao; Hu, Jun; Dang, Bin; He, Jinliang

    2016-10-01

    This paper reports excellent electrical properties in polypropylene grafted with maleic anhydride (PP-g-MAH) and a related mechanism of the enhanced electrical properties. The chemical structure of PP-g-MAH was analyzed and its effect on space charge accumulation, electrical breakdown strength and DC conductivity was studied. Compared with pure PP, the PP-g-MAH exhibits remarkably suppressed space charge accumulation, enhanced electrical breakdown strength and reduced conduction current. The mechanism enhancing the electrical properties was studied by measuring the trap level distribution. It can be explained that abundant deep traps are introduced in PP-g-MAH with the introduction of polar groups in MAH, which reduces the charge mobility and raises the charge injection barrier so as to suppress space charge accumulation. This investigation would contribute to propose a new material modification strategy for designing high-voltage direct current insulation material in addition to the inclusion of nanoparticles.

  10. One-pot synthesis of thermoplastic mixed paramylon esters using trifluoroacetic anhydride.

    PubMed

    Shibakami, Motonari; Tsubouchi, Gen; Sohma, Mitsugu; Hayashi, Masahiro

    2015-03-30

    Mixed paramylon esters prepared from paramylon (a storage polysaccharide of Euglena), acetic acid, and a long-chain fatty acid by one-pot synthesis using trifluoroacetic anhydride as a promoter and solvent were shown to have thermoplasticity. Size exclusion chromatography indicated that the mixed paramylon esters had a weight average molecular weight of approximately 4.9-6.7×10(5). Thermal analysis showed that these esters were stable in terms of the glass transition temperature (>90°C) and 5% weight loss temperature (>320°C). The degree of substitution of the long alkyl chain group, a dominant factor determining thermoplasticity, was controlled by tuning the feed molar ratio of acetic acid and long-chain fatty acid to paramylon. These results implied that the one-pot synthesis is useful for preparing structurally-well defined thermoplastic mixed paramylon esters with high molecular weight. Copyright © 2014 Elsevier Ltd. All rights reserved.

  11. Perfluoroalkylation of Unactivated Alkenes with Acid Anhydrides as the Perfluoroalkyl Source.

    PubMed

    Kawamura, Shintaro; Sodeoka, Mikiko

    2016-07-18

    An efficient perfluoroalkylation of unactivated alkenes with perfluoro acid anhydrides was developed. Copper salts play a crucial role as a catalyst to achieve allylic perfluoroalkylation with the in situ generated bis(perfluoroacyl) peroxides. Furthermore, carboperfluoroalkylation of alkene bearing an aromatic ring at an appropriate position on the carbon side chain was found to proceed under metal-free conditions to afford carbocycles or heterocycles bearing a perfluoroalkyl group. This method, which makes use of readily available perfluoroalkyl sources, offers a convenient and powerful tool for introducing a perfluoroalkyl group onto an sp(3) carbon to construct synthetically useful skeletons. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. Process for the production of 1:4 butanediol from maleic anhydride via ester hydrogenation

    SciTech Connect

    Towers, R.G.; Harris, N.; McKee, D.

    1986-01-01

    A process has been developed for the production of 1:4 butanediol (1:4 BDO from maleic anhydride (MA). The three process steps are:- a) Esterifiction of MA to produce a dialkyl maleate ester based on a modification of commercially proven esterification technology; b) Hydrogenation of the ester, at moderate temperatures and pressures, to 1:4 BD using novel low pressure ester hydrogenation technology. Gamma-Butyrolactone (gamma-BL) and tetrahydrofuran (THF) are produced as co-products. The 1:4 BD/Gamma-BL product ratio can be adjusted to respond to market requirements by recycle of the less desirable product, and THF productivity controlled over wide limits by variation of process parameters; c) Product separation by distillation.

  13. "Push-pull" 1,8-naphthalic anhydride with multiple triphenylamine groups as electron donor

    NASA Astrophysics Data System (ADS)

    Wang, Limin; Shi, Yan; Zhao, Yingyuan; Liu, Heyuan; Li, Xiyou; Bai, Ming

    2014-01-01

    In this paper, the "push-pull" molecules consisting of different number of triphenylamino groups and 1,8-naphthalic anhydride ring were designed and synthesized. The UV-vis absorption and emission spectra of these compounds were recorded. Along with the increase on the number of the electron donating triphenylamino groups, both the absorption and emission bands show significant red shift. More importantly, the fluorescence quantum yields drop sharply along with the increase on the number of triphenylamino groups. The molecular structure, the frontier molecular orbital energies and the energy gaps between the highest occupied molecular orbital (HOMO) and the lowest un-occupied molecular orbital (LUMO) were calculated with DFT method. The calculated results indicate that the connection of more electron donating triphenylamino groups in molecule caused a change for the first excited state from an intramolecular charge transfer (ICT) state to an intramolecular electron transfer state (ET). This change on the first excited state has led to the fluorescence quenching.

  14. Effects of Amine and Anhydride Curing Agents on the VARTM Matrix Processing Properties

    NASA Technical Reports Server (NTRS)

    Grimsley, Brian W.; Hubert, Pascal; Song, Xiaolan; Cano, Roberto J.; Loos, Alfred C.; Pipes, R. Byron

    2002-01-01

    To ensure successful application of composite structure for aerospace vehicles, it is necessary to develop material systems that meet a variety of requirements. The industry has recently developed a number of low-viscosity epoxy resins to meet the processing requirements associated with vacuum assisted resin transfer molding (VARTM) of aerospace components. The curing kinetics and viscosity of two of these resins, an amine-cured epoxy system, Applied Poleramic, Inc. VR-56-4 1, and an anhydride-cured epoxy system, A.T.A.R.D. Laboratories SI-ZG-5A, have been characterized for application in the VARTM process. Simulations were carried out using the process model, COMPRO, to examine heat transfer, curing kinetics and viscosity for different panel thicknesses and cure cycles. Results of these simulations indicate that the two resins have significantly different curing behaviors and flow characteristics.

  15. Surface Functionalization of WO3 Thin Films with (3-Aminopropyl)triethoxysilane and Succinic Anhydride

    NASA Astrophysics Data System (ADS)

    Ta, Thi Kieu Hanh; Tran, Thi Nhu Hoa; Tran, Quang Minh Nhat; Pham, Duy Phong; Pham, Kim Ngoc; Cao, Thi Thanh; Kim, Yong Soo; Tran, Dai Lam; Ju, Heongkyu; Phan, Bach Thang

    2017-06-01

    We report effects of oxygen plasma treatment on the surface functionalization of WO3 thin films with (3-aminopropyl)triethoxysilane (APTES) and succinic anhydride (SA). X-ray diffraction and x-ray photoelectron spectroscopy results indicate the existence of the WO3 phase. Fourier transform infrared spectroscopy measurement shows clear bands at 1040 cm-1 (Si-O-Si), 1556 cm-1 (N-H), 1655 cm-1 (C=O), 2937 cm-1 (C-H) and 3298 cm-1 (N-H), confirming the surface functionalization efficiency enhanced by prior treatment of oxygen plasma. It thus follows that the prior oxygen plasma treatment activates hydroxylation with more -OH groups on the WO3 surface, which can pave a highly efficient way to the surface functionalization by APTES and SA.

  16. Stabilizing alkenyl succinic anhydride (ASA) emulsions with starch nanocrystals and fluorescent carbon dots.

    PubMed

    Gong, Bei; Liu, Wenxia; Chen, Xueshuai; Tan, Hua; Zhang, Xiuli; Wang, Huili; Yu, Dehai; Li, Guodong; Song, Zhaoping

    2017-06-01

    Stabilizing alkenyl succinic anhydride (ASA) emulsions using fine particles instead of cationic starch have attracted much attention in recent years. Herein, starch nanocrystals (SNCs) made from maize starch by H2SO4 hydrolysis were used to co-stabilize ASA emulsions with fluorescent carbon dots (CDs) made hydrothermally from gelatin. The introduction of CDs can significantly enhance the stability and reduce the droplet size of SNC-stabilized ASA-in-water emulsions. Consequently, the sizing performance of the SNC-stabilized ASA emulsion is significantly improved by increasing the CD-to-SNC mass ratio. SNC and CD co-stabilized ASA emulsions show much better sizing performance than starch and CD co-stabilized ASA emulsions, achieving their best sizing performance at a CD-to-SNC mass ratio of 80%. Meanwhile, the morphology of SNC/starch and CD co-stabilized ASA emulsions can be traced under UV excitation. Copyright © 2017 Elsevier Ltd. All rights reserved.

  17. Improved removal of malachite green from aqueous solution using chemically modified cellulose by anhydride.

    PubMed

    Zhou, Yanmei; Min, Yinghao; Qiao, Han; Huang, Qi; Wang, Enze; Ma, Tongsen

    2015-03-01

    Cellulose modified with maleic (M) and phthalic (P) anhydride, to be named CMA and CPA, were tested as feasible adsorbents for the removal of malachite green from aqueous solution. At the same time, the uptake ability of natural cellulose was also studied for comparison. The structure of material was characterized by FT-IR and XRD. The effects of solution pH, initial dye concentration, contact time and temperature were investigated in detail by batch adsorption experiments. The kinetic and isotherm studies suggested that the adsorption followed the pseudo-second-order model and Langmuir isotherm. The maximum adsorption capacity on CMA and CPA were 370 mg g(-1) and 111 mg g(-1), respectively. Furthermore, the thermodynamics studies indicated the spontaneous nature of adsorption of malachite green on adsorbents. All the studied results showed that the modified cellulose could be used as effective adsorption material for the removal of malachite green from aqueous solutions.

  18. Stereodynamic control of star-epoxy/anhydride crosslinking actuated by liquid-crystalline phase transitions.

    PubMed

    Pin, Jean-Mathieu; Mija, Alice; Sbirrazzuoli, Nicolas

    2017-03-08

    The epoxy/anhydride copolymerization kinetics of an original star-epoxy monomer (TriaEP) was explored in dynamic heating mode using a series of isoconversional methods. Negative values of the apparent activation energy (Eα) related to an anti-Arrhenius behavior were observed. The transition from Arrhenius to anti-Arrhenius behavior and vice versa depending on the Eα of polymerization was correlated with the dynamics of mesophasic fall-in/fall-out events, physically induced transition (PIT) and chemically induced transition (CIT). This self-assembly phenomenon induces the generation of an anisotropic crosslinked architecture exhibiting both nematic discotic (ND) and nematic columnar (NC) organization. Particular emphasis was placed on evaluating the juxtaposition/contribution of the liquid-crystalline transitions to crosslinking, considering both the reaction dynamics and the macromolecular vision.

  19. Structure and physicochemical properties of octenyl succinic anhydride modified starches: a review.

    PubMed

    Sweedman, Michael C; Tizzotti, Morgan J; Schäfer, Christian; Gilbert, Robert G

    2013-01-30

    Starches modified with octenyl succinic anhydride (OSA) have been used in a range of industrial applications, particularly as a food additive, for more than half a century. Interest in these products has grown in recent years as a result of new methods and applications becoming available. Due to a combination of OSA's hydrophobic and steric contribution and starch's peculiar highly branched macromolecular structure, these starch derivatives display useful stabilizing, encapsulating, interfacial, thermal, nutritional and rheological properties. We review the synthesis procedures, structural characterization methods and physico-chemical properties, and the influences of the botanical origins and structural parameters of OSA starches on physico-chemical properties. A better understanding of these features has the potential to lead to products with targeted macromolecular structures and optimized properties for specific applications.

  20. Ionic liquids as novel solvents for biosynthesis of octenyl succinic anhydride-modified waxy maize starch.

    PubMed

    Li, Dandan; Zhang, Xiwen; Tian, Yaoqi

    2016-05-01

    Biosynthesis of octenyl succinic anhydride (OSA) starch was investigated using ionic liquids (ILs) as reaction media. Waxy maize starch was pretreated in 1-butyl-3-methylimidazolium chlorine and then esterified with OSA in 1-octyl-3-methylimidazolium nitrate by using Novozyme 435 as catalyst. The degree of substitution of OSA starch reached 0.0130 with 5 wt% starch concentration and 1 wt% lipase dosage based on ILs weight at 50 °C for 3h. The formation of OSA starch was confirmed by fourier transform infrared spectroscopy. Scanning electron microscopy and X-ray diffraction revealed that the morphology and crystal structure of starch were significantly destroyed. Thermogravimetric analysis showed that esterification decreased the thermal stability of starch. The successful lipase-catalyzed synthesis of OSA starch in ILs suggests that ILs are potential replacement of traditional organic solvents for starch ester biosynthesis. Copyright © 2016 Elsevier B.V. All rights reserved.

  1. Crystal structures of alkylperoxo and anhydride intermediates in an intradiol ring-cleaving dioxygenase

    DOE PAGES

    Knoot, Cory J.; Purpero, Vincent M.; Lipscomb, John D.

    2014-12-29

    Intradiol aromatic ring-cleaving dioxygenases use an active site, nonheme Fe3+ to activate O2 and catecholic substrates for reaction. The inability of Fe3+ to directly bind O2 presents a mechanistic conundrum. The reaction mechanism of protocatechuate 3,4-dioxygenase is investigated in this paper using the alternative substrate 4-fluorocatechol. This substrate is found to slow the reaction at several steps throughout the mechanistic cycle, allowing the intermediates to be detected in solution studies. When the reaction was initiated in an enzyme crystal, it was found to halt at one of two intermediates depending on the pH of the surrounding solution. The X-ray crystalmore » structure of the intermediate at pH 6.5 revealed the key alkylperoxo-Fe3+ species, and the anhydride-Fe3+ intermediate was found for a crystal reacted at pH 8.5. Intermediates of these types have not been structurally characterized for intradiol dioxygenases, and they validate four decades of spectroscopic, kinetic, and computational studies. In contrast to our similar in crystallo crystallographic studies of an Fe2+-containing extradiol dioxygenase, no evidence for a superoxo or peroxo intermediate preceding the alkylperoxo was found. This observation and the lack of spectroscopic evidence for an Fe2+ intermediate that could bind O2 are consistent with concerted formation of the alkylperoxo followed by Criegee rearrangement to yield the anhydride and ultimately ring-opened product. Finally, structural comparison of the alkylperoxo intermediates from the intra- and extradiol dioxygenases provides a rationale for site specificity of ring cleavage.« less

  2. Crystal structures of alkylperoxo and anhydride intermediates in an intradiol ring-cleaving dioxygenase

    PubMed Central

    Knoot, Cory J.; Purpero, Vincent M.; Lipscomb, John D.

    2015-01-01

    Intradiol aromatic ring-cleaving dioxygenases use an active site, nonheme Fe3+ to activate O2 and catecholic substrates for reaction. The inability of Fe3+ to directly bind O2 presents a mechanistic conundrum. The reaction mechanism of protocatechuate 3,4-dioxygenase is investigated here using the alternative substrate 4-fluorocatechol. This substrate is found to slow the reaction at several steps throughout the mechanistic cycle, allowing the intermediates to be detected in solution studies. When the reaction was initiated in an enzyme crystal, it was found to halt at one of two intermediates depending on the pH of the surrounding solution. The X-ray crystal structure of the intermediate at pH 6.5 revealed the key alkylperoxo-Fe3+ species, and the anhydride-Fe3+ intermediate was found for a crystal reacted at pH 8.5. Intermediates of these types have not been structurally characterized for intradiol dioxygenases, and they validate four decades of spectroscopic, kinetic, and computational studies. In contrast to our similar in crystallo crystallographic studies of an Fe2+-containing extradiol dioxygenase, no evidence for a superoxo or peroxo intermediate preceding the alkylperoxo was found. This observation and the lack of spectroscopic evidence for an Fe2+ intermediate that could bind O2 are consistent with concerted formation of the alkylperoxo followed by Criegee rearrangement to yield the anhydride and ultimately ring-opened product. Structural comparison of the alkylperoxo intermediates from the intra- and extradiol dioxygenases provides a rationale for site specificity of ring cleavage. PMID:25548185

  3. Crystal structures of alkylperoxo and anhydride intermediates in an intradiol ring-cleaving dioxygenase.

    PubMed

    Knoot, Cory J; Purpero, Vincent M; Lipscomb, John D

    2015-01-13

    Intradiol aromatic ring-cleaving dioxygenases use an active site, nonheme Fe(3+) to activate O2 and catecholic substrates for reaction. The inability of Fe(3+) to directly bind O2 presents a mechanistic conundrum. The reaction mechanism of protocatechuate 3,4-dioxygenase is investigated here using the alternative substrate 4-fluorocatechol. This substrate is found to slow the reaction at several steps throughout the mechanistic cycle, allowing the intermediates to be detected in solution studies. When the reaction was initiated in an enzyme crystal, it was found to halt at one of two intermediates depending on the pH of the surrounding solution. The X-ray crystal structure of the intermediate at pH 6.5 revealed the key alkylperoxo-Fe(3+) species, and the anhydride-Fe(3+) intermediate was found for a crystal reacted at pH 8.5. Intermediates of these types have not been structurally characterized for intradiol dioxygenases, and they validate four decades of spectroscopic, kinetic, and computational studies. In contrast to our similar in crystallo crystallographic studies of an Fe(2+)-containing extradiol dioxygenase, no evidence for a superoxo or peroxo intermediate preceding the alkylperoxo was found. This observation and the lack of spectroscopic evidence for an Fe(2+) intermediate that could bind O2 are consistent with concerted formation of the alkylperoxo followed by Criegee rearrangement to yield the anhydride and ultimately ring-opened product. Structural comparison of the alkylperoxo intermediates from the intra- and extradiol dioxygenases provides a rationale for site specificity of ring cleavage.

  4. Crystal structures of alkylperoxo and anhydride intermediates in an intradiol ring-cleaving dioxygenase

    SciTech Connect

    Knoot, Cory J.; Purpero, Vincent M.; Lipscomb, John D.

    2014-12-29

    Intradiol aromatic ring-cleaving dioxygenases use an active site, nonheme Fe3+ to activate O2 and catecholic substrates for reaction. The inability of Fe3+ to directly bind O2 presents a mechanistic conundrum. The reaction mechanism of protocatechuate 3,4-dioxygenase is investigated in this paper using the alternative substrate 4-fluorocatechol. This substrate is found to slow the reaction at several steps throughout the mechanistic cycle, allowing the intermediates to be detected in solution studies. When the reaction was initiated in an enzyme crystal, it was found to halt at one of two intermediates depending on the pH of the surrounding solution. The X-ray crystal structure of the intermediate at pH 6.5 revealed the key alkylperoxo-Fe3+ species, and the anhydride-Fe3+ intermediate was found for a crystal reacted at pH 8.5. Intermediates of these types have not been structurally characterized for intradiol dioxygenases, and they validate four decades of spectroscopic, kinetic, and computational studies. In contrast to our similar in crystallo crystallographic studies of an Fe2+-containing extradiol dioxygenase, no evidence for a superoxo or peroxo intermediate preceding the alkylperoxo was found. This observation and the lack of spectroscopic evidence for an Fe2+ intermediate that could bind O2 are consistent with concerted formation of the alkylperoxo followed by Criegee rearrangement to yield the anhydride and ultimately ring-opened product. Finally, structural comparison of the alkylperoxo intermediates from the intra- and extradiol dioxygenases provides a rationale for site specificity of ring cleavage.

  5. Studies of phthalocyanine-containing polymers

    NASA Astrophysics Data System (ADS)

    Lee, Pui Sze Priscilla

    This thesis reports the synthesis, spectroscopic and photophysical properties, and in vitro photodynamic activities of several series of phthalocyanine-containing polymers including poly(norbornene), poly(anhydride), and poly(epsilon-caprolactone). Chapter 1 gives a general overview of phthalocyanines including their synthesis and applications. Special emphasis has been placed on hydrophilic and non-aggregated phthalocyanines and their use in photodynamic therapy. In addition, different classes of phthalocyanine-containing polymers will also be mentioned. Chapter 2 discusses the synthesis, characterization, and photophysical properties of a series of poly(norbornene)s with zinc(II) phthalocyanine and amino acid moieties. The copolymers were prepared by copolymerization of 2-(2-norbornenylmethoxy)phthalocyaninatozinc(II) with 5-norbornenes substituted with phenylalanine and tyrosine. As shown by absorption and fluorescence spectroscopy, phthalocyanines in this series of polymer exhibit a rather strong aggregation tendency. Chapter 3 presents the synthesis, characterization, photophysical properties, and in vitro photodynamic activities of a related series of amino acid- and sugar-containing poly(norbornene)s connected axially to a silicon(IV) phthalocyanine core. These polymers exhibit a good solubility in common organic solvents. Due to the axial polymeric substituents, these compounds are free from aggregation and give a high singlet oxygen quantum yield. These polymers in Cremophor EL emulsions also show a high photodynamic activity against HepG2 cells, in particular the polymer with protected galactose moieties. Chapter 4 reports a series of silicon(IV) phthalocyanines substituted with two poly(sebacic anhydride) chains as the axial ligands. The polymers form nanoparticles in water in the presence of surfactants cetyltrimethylammonium bromide (CTAB) and sodium dodecylsulphate (SDS). The degradation of the nanoparticles was carried out in alkaline media and was

  6. Enzyme immobilization on reactive polymer films.

    PubMed

    Cordeiro, Ana L; Pompe, Tilo; Salchert, Katrin; Werner, Carsten

    2011-01-01

    Immobilized enzymes are currently used in many bioanalytical and biomedical applications. This protocol describes the use of thin films of maleic anhydride copolymers to covalently attach enzymes directly to solid supports at defined concentrations. The concentration and activity of the surface-bound enzymes can be tuned over a wide range by adjusting the concentration of enzyme used for immobilization and the physicochemical properties of the polymer platform, as demonstrated here for the proteolytic enzyme Subtilisin A. The versatile method presented allows for the immobilization of biomolecules containing primary amino groups to a broad variety of solid carriers, ranging from silicon oxide surfaces to standard polystyrene well plates and metallic surfaces. The approach can be used to investigate the effects of immobilized enzymes on cell adhesion, and on the catalysis of specific reactions.

  7. Novel thermoresponsive assemblies of co-grafted natural and synthetic polymers for water purification.

    PubMed

    Paneysar, Joginder Singh; Barton, Stephen; Chandra, Sudeshna; Ambre, Premlata; Coutinho, Evans

    2017-03-01

    Water contamination and its purification are a global problem. The current approach to purify water is reduction of impurities to acceptable levels. One of the ways to achieve this is by use of water-soluble polymers that extract organic and metallic contaminants, from water. This paper presents a blend of composite polymers that eliminates both the contaminants simultaneously by the principle of adsorption at lower critical solution temperature. These composite polymers have been synthesized by grafting poly(N,N-diethylacrylamide), poly(N-isopropylacrylamide) and poly(N-vinylcaprolactam) on-to the natural polymer chitosan or its derivatives, giving smart graft polymeric assemblies (GPAs). One of the graft polymers, GPA-2, exhibits excellent adsorption properties able to remove metal ions like cadmium, cobalt, copper, lead, iron and also organic impurities like chlorophenol and phthalic anhydride. Studies reveal that 6 mg/ml GPA-2 is able to effect a 100% removal of organic impurities - chlorophenol (50 ppm) and phthalic anhydride (70 ppm) - from water, while complete removal of the heavy metal ions (Cu(+2), Co(+2) and Cd(+2)) together at 30 ppm concentration has been achieved with 7.5 mg/ml GPA-2. The reduction in level of impurities along with recyclability and reproducibility in the elimination spectrum makes these assemblies promising materials in water treatment.

  8. Polymer adsorption

    NASA Astrophysics Data System (ADS)

    Joanny, Jean-Francois

    2008-03-01

    The aim of this talk is to review Pierre-Gilles deGennes' work on polymer adsorption and the impact that it has now in our understanding of this problem. We will first present the self-consistent mean-field theory and its applications to adsorption and depletion. De Gennes most important contribution is probably the derivation of the self-similar power law density profile for adsorbed polymer layers that we will present next, emphasizing the differences between the tail sections and the loop sections of the adsorbed polymers. We will then discuss the kinetics of polymer adsorption and the penetration of a new polymer chain in an adsobed layer that DeGennes described very elegantly in analogy with a quantum tunneling problem. Finally, we will discuss the role of polymer adsorption for colloid stabilization.

  9. New polymer systems: Chain extension by dianhydrides

    NASA Technical Reports Server (NTRS)

    Rhein, R. A.; Ingham, J. D.

    1974-01-01

    Three anhydrides provide effective chain extension of hydroxy-terminated polyalkylene oxides and polybutadienes. Novel feature of these anhydride reactants is that they are difunctional as anhydrides, but they are tetrafunctional if conditions are selected that lead to total esterification or reaction of all carboxyl groups.

  10. Water-soluble metal working fluids additives derived from the esters of acid anhydrides with higher alcohols for aluminum alloy materials.

    PubMed

    Yamamoto, Syutaro; Tomoda, Hideyuki; Watanabe, Shoji

    2007-01-01

    Water-soluble metal working fluids are used for processing of aluminum alloy materials. This short article describes properties of new additives in water-soluble metal working fluids for aluminum alloy materials. Many half esters or diesters were prepared from the reactions of higher alcohols with acid anhydrides. Interestingly, diesters of PTMG (tetrahydrofuran oligomer, MW = 650 and 1000) and polybutylene oxide (MW = 650) with maleic anhydride and succinic anhydride showed both of an excellent anti-corrosion property for aluminum alloy and a good hard water tolerance. The industrial soluble type processing oils including these additives also showed anti-corrosion property and hard water tolerance.

  11. Development of Highly Active and Regioselective Catalysts for the Copolymerization of Epoxides with Cyclic Anhydrides: An Unanticipated Effect of Electronic Variation.

    PubMed

    DiCiccio, Angela M; Longo, Julie M; Rodríguez-Calero, Gabriel G; Coates, Geoffrey W

    2016-06-08

    Recent developments in polyester synthesis have established several systems based on zinc, chromium, cobalt, and aluminum catalysts for the ring-opening alternating copolymerization of epoxides with cyclic anhydrides. However, to date, regioselective processes for this copolymerization have remained relatively unexplored. Herein we report the development of a highly active, regioselective system for the copolymerization of a variety of terminal epoxides and cyclic anhydrides. Unexpectedly, electron withdrawing substituents on the salen framework resulted in a more redox stable Co(III) species and longer catalyst lifetime. Using enantiopure propylene oxide, we synthesized semicrystalline polyesters via the copolymerization of a range of epoxide/anhydride monomer pairs.

  12. Star Polymers.

    PubMed

    Ren, Jing M; McKenzie, Thomas G; Fu, Qiang; Wong, Edgar H H; Xu, Jiangtao; An, Zesheng; Shanmugam, Sivaprakash; Davis, Thomas P; Boyer, Cyrille; Qiao, Greg G

    2016-06-22

    Recent advances in controlled/living polymerization techniques and highly efficient coupling chemistries have enabled the facile synthesis of complex polymer architectures with controlled dimensions and functionality. As an example, star polymers consist of many linear polymers fused at a central point with a large number of chain end functionalities. Owing to this exclusive structure, star polymers exhibit some remarkable characteristics and properties unattainable by simple linear polymers. Hence, they constitute a unique class of technologically important nanomaterials that have been utilized or are currently under audition for many applications in life sciences and nanotechnologies. This article first provides a comprehensive summary of synthetic strategies towards star polymers, then reviews the latest developments in the synthesis and characterization methods of star macromolecules, and lastly outlines emerging applications and current commercial use of star-shaped polymers. The aim of this work is to promote star polymer research, generate new avenues of scientific investigation, and provide contemporary perspectives on chemical innovation that may expedite the commercialization of new star nanomaterials. We envision in the not-too-distant future star polymers will play an increasingly important role in materials science and nanotechnology in both academic and industrial settings.

  13. Polymer Electrolytes

    NASA Astrophysics Data System (ADS)

    Hallinan, Daniel T.; Balsara, Nitash P.

    2013-07-01

    This review article covers applications in which polymer electrolytes are used: lithium batteries, fuel cells, and water desalination. The ideas of electrochemical potential, salt activity, and ion transport are presented in the context of these applications. Potential is defined, and we show how a cell potential measurement can be used to ascertain salt activity. The transport parameters needed to fully specify a binary electrolyte (salt + solvent) are presented. We define five fundamentally different types of homogeneous electrolytes: type I (classical liquid electrolytes), type II (gel electrolytes), type III (dry polymer electrolytes), type IV (dry single-ion-conducting polymer electrolytes), and type V (solvated single-ion-conducting polymer electrolytes). Typical values of transport parameters are provided for all types of electrolytes. Comparison among the values provides insight into the transport mechanisms occurring in polymer electrolytes. It is desirable to decouple the mechanical properties of polymer electrolyte membranes from the ionic conductivity. One way to accomplish this is through the development of microphase-separated polymers, wherein one of the microphases conducts ions while the other enhances the mechanical rigidity of the heterogeneous polymer electrolyte. We cover all three types of conducting polymer electrolyte phases (types III, IV, and V). We present a simple framework that relates the transport parameters of heterogeneous electrolytes to homogeneous analogs. We conclude by discussing electrochemical stability of electrolytes and the effects of water contamination because of their relevance to applications such as lithium ion batteries.

  14. Polymer Chemistry

    NASA Technical Reports Server (NTRS)

    Williams, Martha; Roberson, Luke; Caraccio, Anne

    2010-01-01

    This viewgraph presentation describes new technologies in polymer and material chemistry that benefits NASA programs and missions. The topics include: 1) What are Polymers?; 2) History of Polymer Chemistry; 3) Composites/Materials Development at KSC; 4) Why Wiring; 5) Next Generation Wiring Materials; 6) Wire System Materials and Integration; 7) Self-Healing Wire Repair; 8) Smart Wiring Summary; 9) Fire and Polymers; 10) Aerogel Technology; 11) Aerogel Composites; 12) Aerogels for Oil Remediation; 13) KSC's Solution; 14) Chemochromic Hydrogen Sensors; 15) STS-130 and 131 Operations; 16) HyperPigment; 17) Antimicrobial Materials; 18) Conductive Inks Formulations for Multiple Applications; and 19) Testing and Processing Equipment.

  15. Synthesis of BISGMA derivatives, properties of their polymers and composites.

    PubMed

    Sandner, B; Baudach, S; Davy, K W; Braden, M; Clarke, R L

    1997-01-01

    2,2-Bis[4-(2 hydroxy-3-methacryloyloxy propoxy) phenyl] propane (BisGMA) is commonly the main component of the organic matrix of dental filling materials. Derivatives of BisGMA were synthesized from the diglycidyl ether of Bisphenol A (DGEBA) by the parallel reaction with methacrylic acid (MAA) and isophthalic acid as well as mixtures of methacrylic anhydride with palmitic acid and acetic anhydride, respectively, whereby MAA was partially substituted by the latter components. By this technique the structure of BisGMA monomer could be varied with regard to weight content of C=C double bonds, the hydrophilicity of the molecule as well as its flexibility or stiffness. Free-radical initiated homopolymerization of the monomers was carried out at 80 degrees C. Composites, prepared from mixtures of monomers with triethylene glycol dimethacrylate (TEGDMA) filled with 76% silica were room temperature polymerized using both redox and photoinitiated techniques. The polymerization shrinkage, diffusion coefficients of water in the crosslinked polymer, and some thermal properties of the homopolymers were determined. Mechanical properties of the resulting polymers and composites are compared to those of BisGMA itself.

  16. Effects of shear flow on reactive coupling of polymer chains at melt interfaces

    NASA Astrophysics Data System (ADS)

    Zhang, Jianbin; Lodge, Timothy; Macosko, Christopher

    2006-03-01

    The coupling reaction of functional polymers at static polymer-polymer interfaces is typically much slower than that at interfaces formed during mixing (see, for example, Reference 1). We have demonstrated that the imposed simple shear can accelerate coupling reactions at flat interfaces. For amine-terminal polystyrene (PS-NH2)/anhydride terminal poly(methyl methacrylate) (PMMA-anh), the PMMA-anh conversion under dynamic oscillation even at strain amplitude as small as 1% is seven times that under static conditions. Reaction time and temperature and the total interfacial area were maintained the same. Similar behavior was found for both bilayer and multilayer samples. Under steady simple shear, the reaction conversion and the rate of interfacial area generation are comparable to that of batch mixing. *Macosko, C. W.; Jeon. H. K.; Hoye, T. R. Prog. Polym. Sci. 2005, 30, 939.

  17. Polymers & People

    ERIC Educational Resources Information Center

    Lentz, Linda; Robinson, Thomas; Martin, Elizabeth; Miller, Mary; Ashburn, Norma

    2004-01-01

    Each Tuesday during the fall of 2002, teams of high school students from three South Carolina counties conducted a four-hour polymer institute for their peers. In less than two months, over 300 students visited the Charleston County Public Library in Charleston, South Carolina, to explore DNA, nylon, rubber, gluep, and other polymers. Teams of…

  18. Polymers & People

    ERIC Educational Resources Information Center

    Lentz, Linda; Robinson, Thomas; Martin, Elizabeth; Miller, Mary; Ashburn, Norma

    2004-01-01

    Each Tuesday during the fall of 2002, teams of high school students from three South Carolina counties conducted a four-hour polymer institute for their peers. In less than two months, over 300 students visited the Charleston County Public Library in Charleston, South Carolina, to explore DNA, nylon, rubber, gluep, and other polymers. Teams of…

  19. A biotin-conjugated pyridine-based isatoic anhydride, a selective room temperature RNA-acylating agent for the nucleic acid separation.

    PubMed

    Ursuegui, S; Yougnia, R; Moutin, S; Burr, A; Fossey, C; Cailly, T; Laayoun, A; Laurent, A; Fabis, F

    2015-03-28

    Isatoic anhydride derivatives, including a biotin and a disulfide linker were specifically designed for nucleic acid separation. 2'-OH selective RNA acylation, capture of biotinylated RNA adducts by streptavidin-coated magnetic beads and disulfide chemical cleavage led to isolation of highly enriched RNA samples from an initial 9/1 DNA-RNA mixture. Starting from the parent compound N-methylisatoic anhydride A which was used at 65 °C, we improved the extraction process by designing a new generation of isatoic anhydrides that are able to react under smoother conditions. Among them, a pyridine-based isatoic anhydride derivative 15f was found to be reactive at room temperature, leading to enhance the efficiency and selectivity of the extraction process by significantly reducing DNA side extraction. The extracted and purified RNAs can then be detected by RT-PCR.

  20. Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides.

    PubMed

    Braunstein, Hannah; Langevin, Spencer; Khim, Monique; Adamson, Jonathan; Hovenkotter, Katie; Kotlarz, Lindsey; Mansker, Brandon; Beng, Timothy K

    2016-09-21

    A modular substrate-controlled hexannulation of inherently promiscuous 1,3-azadienes with hexacyclic anhydrides, which affords versatile vicinally functionalized allylic lactams, in high yields, regio- and stereoselectivities is described.

  1. Assessment of 4-nitro-1,8-naphthalic anhydride reductase activity in homogenates of bakers' yeast by reversed-phase high-performance liquid chromatography.

    PubMed

    Xu, Jianqiang; Yang, Qing; Qian, Xuhong; Samuelsson, Jörgen; Janson, Jan-Christer

    2007-03-01

    A simple reversed-phase high-performance liquid chromatographic (RP-HPLC) method was developed for the simultaneous determination of yield and conversion ratio of 4-nitro-1,8-naphthalic anhydride to 4-amino-1,8-naphthalic anhydride following incubation with a crude bakers' yeast homogenate. The analytes were separated on a C18 column in gradient mode. The detection limit of 4-amino-1,8-naphthalic anhydride is 10ng/microl when using a 10microl sample injection volume. The nitroreductase activity in the homogenate system can be assessed during the bioconversion process. The method can be used for the simultaneous detection of 4-hydroxylamino-1,8-naphthalic anhydride, an intermediate with limited stability.

  2. Polymers with complexing properties. Simple poly(amino acids)

    NASA Technical Reports Server (NTRS)

    Roque, J. M.

    1978-01-01

    The free amino (0.3 equiv/residue) and carboxyl (0.5 equiv/residue) groups of thermal polylysine increased dramatically on treatment with distilled water. The total hydrolysis of such a polymer was abnormal in that only about 50% of the expected amino acids were recovered. Poly (lysine-co-alanine-co-glycine) under usual conditions hydrolyzed completely in 8 hours; whereas, when it was pretreated with diazomethane, a normal period of 24 hours was required to give (nearly) the same amounts of each free amino acid as compared with those obtained from the untreated polymer. The amino groups of the basic thermal poly(amino acids) were sterically hindered. The existence of nitrogen atoms linking two or three chains and reactive groups (anhydride, imine) were proposed.

  3. Methylol polyesters of C12-C22 hydrocarbon substituted succinic anhydride or acid, their preparation and use as additives for lubricants and fuels

    SciTech Connect

    Gutierrez, A.; Ryer, J.; Shaub, H.; Winans, E.D.

    1980-06-24

    Methylol polyester derivatives of C12-C22 hydrocarbon substituted succinic anhydride or acid which are the equimolar reaction products of said C12-C22 hydrocarbon substituted succinic anhydride or acid and a cyclic poly(Methylol) compound provide activity: in fuels as rust inhibitors; in automatic transmission fluids as copper corrosion inhibitors; and, in automotive, industrial and lubricating oils as sludge dispersants , rust-inhibitors, friction reducers (Lubricity agents) and copper alloy corrosion inhibitors.

  4. Characterization of the Structure-Processing-Performance Relations of Phenylethynyl Phthalic Anhydride Crosslinked Fluorinated Polyimides (AFR-PEPA-N) and Their Carbon Fiber Composites

    DTIC Science & Technology

    2007-04-12

    FA9550-04-1-0137 Relations of Phenylethynyl Phthalic Anhydride Crosslinked Fluorinated Polyimides (AFR-PEPA-N) and Their Carbon Fiber Composites 5b. GRANT...structure-processing-performance relations of phenylethynyl phthatic anhydride crosslinked fluorinated polyimides (AFR-PEPA-N) and their carbon fiber...composites for applications for future Air Force vehicles and associated propulsion systems . The technical areas that were primarily pursued and

  5. Application of palladium-catalyzed carboxyl anhydride-boronic acid cross coupling in the synthesis of novel bile acids analogs with modified side chains.

    PubMed

    Mayorquín-Torres, Martha C; Flores-Álamo, Marcos; Iglesias-Arteaga, Martin A

    2015-09-01

    Palladium-catalyzed cross coupling of 4-methoxycarbonyl phenyboronic acid with acetylated bile acids in which the carboxyl functions was activated by formation of a mixed anhydride with pivalic anhydride afforded the cross coupled compounds, which were converted in novel side chain modified bile acids by one pot carbonyl reduction/removal of the protecting acetyl groups by Wolff-Kishner reduction. Unambiguous assignments of the NMR signals and crystal characterization of the heretofore unknown compounds are provided.

  6. Kinetics of the reactions of the acid anhydrides with aromatic amines in aprotic solvents. M.S. Thesis. Final Report

    NASA Technical Reports Server (NTRS)

    Sugg, E.; Mason, J. G.

    1983-01-01

    Work has revealed that diamine derivatives of diphenylmethane (IV), diphenyl ether (V), benzophenone (IV), fluorene (VII), and fluorenone (VIII) polymerizations with pyromellitic dianhydride in DMA were dependent on the basicity of the amine compound. The correlation between the basicity of the amine and its reactivity with phthalic anhydride was determined. Basicity measurements were made by potentiometric titration of each amine in an acetonitrile-water solvent system, from which the pKa of the amine could be determined. Reactivity was defined in terms of the second order rate constant derived form spectrophotometric examination of the reaction between each amine and phthalic anhydride in DMA. This reaction was expected to proceed in either one (for a monoamine) or two (for a diamine) stages.

  7. A facile synthesis of deuterium labeled 2,2-dimethyl-[2H6]-succinic acid and its anhydride.

    PubMed

    Srinivas, G; Unny, V K P; Mukkanti, K; Choudary, B M

    2013-05-30

    Deuterium labeled 2,2-dimethyl-[(2)H(6)]-succinic anhydride by a sequence of reactions involving Knoevenagel condensation of [(2)H(6)]-acetone with ethyl cyanoacetate in the presence of piperidine, Michael addition of cyanide, HCl hydrolysis, simultaneous decarboxylation, and subsequent dehydration using acetic anhydride in an overall yield of 34.23% based on [(2)H(6)]-acetone utilized in the reaction is reported. The title compounds were characterized and confirmed spectroscopically by Fourier transform infrared, (1) H-NMR, and Mass. The chemical purity as determined by HPLC was 99%. To the best of our knowledge, the synthesis of these specifically deuterium labeled compounds has not been reported so far. Copyright © 2013 John Wiley & Sons, Ltd.

  8. Octahedral d[sup 6] Bis(maleimide) and Bis(maleic anhydride) complexes of molybdenum

    SciTech Connect

    Lai, Chen-Hsing; Cheng, Chien-Hong; Liao, Fen-Ling; Wang, Sue-Lein )

    1993-12-08

    Mo(CO)[sub 3](CH[sub 3]CN)[sub 3] reacts with 2 equiv of alkene, where the alkene is maleimide (MI), N-phenylmaleimide (PhMI), or N-methylmaleimide, to give the corresponding Mo(CO)[sub 2](alkene)[sub 2](CH[sub 3]CN)[sub 2] complex (1a-c, respectively) in excellent yield. Dissolution of 1 in DMSO led to the substitution of acetonitrile ligands by DMSO to form the corresponding cis bis(DMSO) complexes 2a-c. Addition of 1 equiv of NN to 1 yields MO(CO)[sub 2](alkene)[sub 2](alkene)[sub 2](NN) (NN = en, alkene = PhMI (3b), MeMI (3c); NN = o-phenylenediamine, alkene = PhMI (4)). Treatment of Mo-(CO)[sub 4](NN) (NN = phen or bpy), with 2 equiv of alkene in refluxed acetonitrile for 2 h gave Mo(CO)[sub 2]-(alkene)[sub 2](NN) (NN = phen, alkene = MI (5a), PhMI (5b); NN = bpy, alkene = MI (6a), PhMI (6b)). Treatment of Mo(CO)[sub 3](CH[sub 3]CN)[sub 3] with 2 equiv of maleic anhydride (MA) gave Mo(CO)[sub 2](MA)[sub 2](CH[sub 3]CN)[sub 2] (7). The acetonitrile ligands in 7 were replaced by DMSO molecules to give complex 8 as 7 was dissolved in DMSO. Similarly, the reaction of 7 with a bidentate ligand NN (phen or bpy) gave the substituted product Mo(CO)[sub 2](MA)[sub 2](NN) (9 or 10). The structures and conformations of 1b and 7 were determined by X-ray diffraction. Both molecules adopt an octahedral geometry with mutually perpendicular trans alkene ligands and each alkene ligand eclipses a N-Mo-CO vector. Each PhMI or MA is oriented so that the central nitrogen or oxygen atom points to a carbonyl group. 1b crystallizes in triclinic space group P1. There are three possible conformations for a trans bis(maleimide) or bis(maleic anhydride) complex (I-III). The results of X-ray and NMR studies indicated that the main conformation of complexes 1-10 is I both in the solid state and in solution.

  9. Ficusmicrochlorin A-C, two new methoxy lactone chlorins and an anhydride chlorin from the leaves of Ficus microcarpa.

    PubMed

    Lin, Huan-You; Chiu, Hsi-Lin; Lu, Te-Ling; Tzeng, Chih-Ying; Lee, Tzong-Huei; Lee, Ching-Kuo; Shao, Yi-Yuan; Chen, Chiy-Rong; Chang, Chi-I; Kuo, Yueh-Hsiung

    2011-01-01

    Two new methoxy lactone chlorins ficusmicrochlorin A (1) and ficusmicrochlorin B (2), and one new anhydride chlorin ficusmicrochlorin C (3), along with eight known pheophytins were isolated from the leaves of Ficus microcarpa. Their structures were determined by the extensive 1D- and 2D-NMR techniques. New pheophytin compound was rarely obtained from natural sources. In the past ten years, only three new natural pheophytins were characterized.

  10. Polymer-coated fluorescent CdSe-based quantum dots for application in immunoassay.

    PubMed

    Speranskaya, Elena S; Beloglazova, Natalia V; Lenain, Pieterjan; De Saeger, Sarah; Wang, Zhanhui; Zhang, Suxia; Hens, Zeger; Knopp, Dietmar; Niessner, Reinhard; Potapkin, Dmitry V; Goryacheva, Irina Yu

    2014-03-15

    The paper describes all stages of synthesis and characterization of biocompatible CdSe-based core/shell quantum dots (QDs) and their application as fluorescent label for immunoassay. Special attention was focused on development of maleic anhydride-based amphiphilic polymers for QDs solubilization in aqueous media. In this work two PEG-amines were tried for polymer modification: monoamine Jeffamine M 1000 used previously in some researches and diamine Jeffamine ED-2003 applied for the first time for QDs solubilization. The use of different Jeffamines allows us to obtain QDs with carboxyl or amine functional groups available for conjugation. The influence of polymer composition on optical properties of the nanocrystals and their stability in aqueous solutions as well as on their conjugation with biomolecules was studied. QDs with different coatings were used as biolabels in quantitative fluorescence microtiter plate immunoassay and qualitative on-site column test. It was found that quantum dots covered with amphiphilic polymer prepared from poly(maleic anhydride-alt-1-octadecene) and Jeffamine ED-2003 retained up to 90% of their initial brightness, easily conjugated with protein and showed low non-specific adsorption. In optimized conditions the obtained QDs were successfully used for determination of mycotoxin deoxynivalenol in wheat and maize samples by fluorescence microtiter plate immunoassay with an IC50 of 220 μg kg(-1) and by on-site column test with cut-off of 500 μg kg(-1).

  11. PEG branched polymer for functionalization of nanomaterials with ultralong blood circulation.

    PubMed

    Prencipe, Giuseppe; Tabakman, Scott M; Welsher, Kevin; Liu, Zhuang; Goodwin, Andrew P; Zhang, Li; Henry, Joy; Dai, Hongjie

    2009-04-08

    Nanomaterials have been actively pursued for biological and medical applications in recent years. Here, we report the synthesis of several new poly(ethylene glycol) grafted branched polymers for functionalization of various nanomaterials including carbon nanotubes, gold nanoparticles (NPs), and gold nanorods (NRs), affording high aqueous solubility and stability for these materials. We synthesize different surfactant polymers based upon poly(gamma-glutamic acid) (gammaPGA) and poly(maleic anhydride-alt-1-octadecene) (PMHC18). We use the abundant free carboxylic acid groups of gammaPGA for attaching lipophilic species such as pyrene or phospholipid, which bind to nanomaterials via robust physisorption. Additionally, the remaining carboxylic acids on gammaPGA or the amine-reactive anhydrides of PMHC18 are then PEGylated, providing extended hydrophilic groups, affording polymeric amphiphiles. We show that single-walled carbon nanotubes (SWNTs), Au NPs, and NRs functionalized by the polymers exhibit high stability in aqueous solutions at different pH values, at elevated temperatures, and in serum. Moreover, the polymer-coated SWNTs exhibit remarkably long blood circulation (t(1/2) = 22.1 h) upon intravenous injection into mice, far exceeding the previous record of 5.4 h. The ultralong blood circulation time suggests greatly delayed clearance of nanomaterials by the reticuloendothelial system (RES) of mice, a highly desired property for in vivo applications of nanomaterials, including imaging and drug delivery.

  12. Polymer-organoclay nanocomposites by melt processing

    NASA Astrophysics Data System (ADS)

    Cui, Lili

    2009-12-01

    Polymer-layered silicate nanocomposites based on a variety of polymer matrices and several organoclays were prepared by melt processing. A detailed characterization of the thermal degradation of several commercial and experimental organoclays often used to form polymer nanocomposites was reported. The surfactant type, loading, and purification level of organoclay significantly affect their thermal stability; however, broadly speaking, the results suggest that these differences in thermal stability do not appear to have much effect on the morphology and properties of the nanocomposites formed from them. It seems that the thermal stability of organoclays is not the key factor in organoclay exfoliation in melt processed polymer nanocomposites, since the exfoliation/dispersion process may have been completed on a time scale before the degradation of surfactant progresses to a detrimental level. Polymer nanocomposites have been made from a variety of polymers; however, few matrices have demonstrated the ability to readily exfoliate the organoclay as well as nylon 6, especially for highly hydrophobic materials like polyolefins. Hence, a significant part of this research work was devoted to explore various routes to improve polyolefin-organoclay interactions, and thus, organoclay exfoliation in these systems. Amine grafted polypropylenes and a conventionally used maleic anhydride grafted polypropylene were used as compatibilizers for polypropylene based nanocomposites to improve the organoclay exfoliation. A series of ethylene vinyl acetate copolymers, the polarity of which can be adjusted by varying their vinyl acetate contents, based nanocomposites were prepared as the model system to address the relationship between the polarity of the polymers and their preferences over various organoclay structures. Attempts were made to explore the effect of degree of neutralization of acid groups in ionomers on the morphology and properties of nanocomposites, and it seems that the

  13. Mixed Anhydride Intermediates in the Reaction of 5(4H)-Oxazolones with Phosphate Esters and Nucleotides.

    PubMed

    Liu, Ziwei; Rigger, Lukas; Rossi, Jean-Christophe; Sutherland, John D; Pascal, Robert

    2016-10-10

    5(4H)-Oxazolones can be formed through the activation of acylated α-amino acids or of peptide C termini. They constitute potentially activated intermediates in the abiotic chemistry of peptides that preceded the origin of life or early stages of biology and are capable of yielding mixed carboxylic-phosphoric anhydrides upon reaction with phosphate esters and nucleotides. Here, we present the results of a study aimed at investigating the chemistry that can be built through this interaction. As a matter of fact, the formation of mixed anhydrides with mononucleotides and nucleic acid models is shown to take place at positions involving a mono-substituted phosphate group at the 3'- or 5'-terminus but not at the internal phosphodiester linkages. In addition to the formation of mixed anhydrides, the subsequent intramolecular acyl or phosphoryl transfers taking place at the 3'-terminus are considered to be particularly relevant to the common prebiotic chemistry of α-amino acids and nucleotides. © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

  14. Sensitive detection of proteins in polyacrylamide gel via isatoic anhydride derivatization: Introduction of a low-cost fluorescent prelabeling procedure.

    PubMed

    Asadollahi, Kazem; Rafiee, Saharnaz; Riazi, Gholamhossein

    2016-10-01

    Here, we introduce isatoic anhydride as a sensitive and commodious fluorescent prelabel for detection of proteins in one-dimensional polyacrylamide gels. High reactivity of isatoic anhydride with nucleophiles in mild alkaline environments makes it an appropriate tag for labeling of biomolecules. In this study, we show that preelectrophoresis labeling of proteins with isatoic anhydride for few minutes at room temperature allows detection of 2-4 ng of standard proteins, BSA and lysozyme, per band. Proteins were successfully labeled in the presence of a wide range of common biological reagents and in crude cell extract. The labeled proteins have the same electrophoretic migration in comparison to unlabeled proteins; however the application of saturation labeling method results in slight band broadening. Compatibility of the method with downstream processes was assessed by tryptic digestion of labeled proteins and study of peptide mixture using gel electrophoresis which revealed partial digestion of labeled proteins due to lysine modification. The present procedure is sensitive, rapid, and inexpensive and is a promising alternative for current protein staining procedures, where downstream processes are not desired.

  15. Mixed Anhydride Intermediates in the Reaction of 5(4H)‐Oxazolones with Phosphate Esters and Nucleotides

    PubMed Central

    Liu, Ziwei; Rigger, Lukas; Rossi, Jean‐Christophe; Sutherland, John D.

    2016-01-01

    Abstract 5(4H)‐Oxazolones can be formed through the activation of acylated α‐amino acids or of peptide C termini. They constitute potentially activated intermediates in the abiotic chemistry of peptides that preceded the origin of life or early stages of biology and are capable of yielding mixed carboxylic‐phosphoric anhydrides upon reaction with phosphate esters and nucleotides. Here, we present the results of a study aimed at investigating the chemistry that can be built through this interaction. As a matter of fact, the formation of mixed anhydrides with mononucleotides and nucleic acid models is shown to take place at positions involving a mono‐substituted phosphate group at the 3’‐ or 5’‐terminus but not at the internal phosphodiester linkages. In addition to the formation of mixed anhydrides, the subsequent intramolecular acyl or phosphoryl transfers taking place at the 3’‐terminus are considered to be particularly relevant to the common prebiotic chemistry of α‐amino acids and nucleotides. PMID:27534830

  16. Biomass-derived monomers for performance-differentiated fiber reinforced polymer composites

    DOE PAGES

    Rorrer, Nicholas A.; Vardon, Derek R.; Dorgan, John R.; ...

    2017-03-14

    Nearly all polymer resins used to manufacture critically important fiber reinforced polymer (FRP) composites are petroleum sourced. In particular, unsaturated polyesters (UPEs) are widely used as matrix materials and are often based on maleic anhydride, a four-carbon, unsaturated diacid. Typically, maleic anhydride is added as a reactant in a conventional step-growth polymerization to incorporate unsaturation throughout the backbone of the UPE, which is then dissolved in a reactive diluent (styrene is widely used) infused into a fiber mat and cross-linked. Despite widespread historical use, styrene has come under scrutiny due to environmental and health concerns; in addition, many conceivable UPEsmore » are not soluble in styrene. In this study, we demonstrate that renewably-sourced monomers offer the ability to overcome these issues and improve overall composite performance. The properties of poly(butylene succinate)-based UPEs incorporating maleic anhydride are used as a baseline for comparison against UPEs derived from fumaric acid, cis,cis-muconate, and trans,trans-muconate, all of which can be obtained biologically. The resulting biobased UPEs are combined with styrene, methacrylic acid, or a mixture of methacrylic acid and cinnaminic acid, infused into woven fiberglass and cross-linked with the addition of a free-radical initiator and heat. This process produces a series of partially or fully bio-derived composites. Overall, the muconate-containing UPE systems exhibit a more favorable property suite than the maleic anhydride and fumaric acid counterparts. In all cases at the same olefinic monomer loading, the trans,trans-muconate polymers exhibit the highest shear modulus, storage modulus, and glass transition temperature indicating stronger and more thermally resistant materials. They also exhibit the lowest loss modulus indicating a greater adhesion to the glass fibers. The use of a mixture of methacrylic and cinnaminic acid as the reactive diluent

  17. Effect of surface modified kaolin on properties of polypropylene grafted maleic anhydride

    NASA Astrophysics Data System (ADS)

    Yang, Ni; Zhang, Zuo-Cai; Ma, Ning; Liu, Huan-Li; Zhan, Xue-Qing; Li, Bing; Gao, Wei; Tsai, Fang-Chang; Jiang, Tao; Chang, Chang-Jung; Chiang, Tai-Chin; Shi, Dean

    To achieve reinforcement of mechanical and thermal performances of polypropylene (PP) product, this work aimed at fabrication of surface modified kaolin (M-kaolin) filled polypropylene grafted maleic anhydride (PP-g-MAH) composites with varying contents of fillers and investigation of their mechanical and thermal properties. And the prepared PP-g-MAH/M-kaolin composites were characterized by means of Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM) and thermogravimetric analysis (TGA). Fracture analysis by SEM showed M-kaolin particles were well dispersed in the PP-g-MAH matrix. Mechanical behaviors were determined by tensile strength, tensile strain at break and impact strength analysis. Impact strength of PP-g-MAH/2 wt% M-kaolin composites was improved up to 30% comparing with unfilled composites. Thermostability had been found enhanced when M-kaolin added. The results revealed PP-g-MAH/M-kaolin composites showed the optimal thermal and mechanical properties when 2 wt% of M-kaolin was added.

  18. Granular size of potato starch affects structural properties, octenylsuccinic anhydride modification and flowability.

    PubMed

    Wang, Chan; Tang, Chuan-He; Fu, Xiong; Huang, Qiang; Zhang, Bin

    2016-12-01

    Native potato starch (PS) granules were separated into three size fractions: larger than 30μm (P-L), 15-30μm (P-M), and smaller than 15μm (P-S). The morphological and crystalline structure of fractionated potato starches were investigated by light and scanning electron microscopy (SEM), X-ray diffraction (XRD) and differential scanning calorimetry (DSC). The P-L fraction showed ellipsoidal shape and B-type X-ray pattern, whereas the P-S fraction had spherical shape and A-type pattern. The fluorophore-assisted capillary electrophoresis data showed that the P-L fraction had more B2 chains and less short A and B1 chains than the P-S counterparts. Smaller granules with larger specific surface area had higher degree of substitution when reacted with octenylsuccinic anhydride (OSA), and showed more uniform distribution of octenylsuccinate substituents. Both OSA modified and unmodified P-S samples showed higher flowability compared with the P-L counterparts. Copyright © 2016 Elsevier Ltd. All rights reserved.

  19. Crystal structure of γ-methyl l-glutamate N-carb-oxy anhydride.

    PubMed

    Kanazawa, Hitoshi; Inada, Aya; Sakon, Aya; Uekusa, Hidehiro

    2015-01-01

    In the title compound, C7H9NO5, alternative name N-carb-oxy-l-glutamic anhydride γ-methyl ester, the oxazolidine ring is essentially planar with a maximum deviation of 0.020 (3) Å. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds between the imino group and the carbonyl O atom in the methyl ester group, forming a tape structure along the a-axis direction. The tapes are linked by C-H⋯O inter-actions into a sheet parallel to the ac plane. The tapes are also stacked along the b axis with short contacts between the oxazolidine rings [C⋯O contact distances = 2.808 (4)-3.060 (4) Å], so that the oxazolidine rings are arranged in a layer parallel to the ab plane. This arrangement of the oxazolidine rings is very preferable for the polymerization of the title compound in the solid state.

  20. Differential induction of cytochrome P450-mediated triasulfuron metabolism by naphthalic anhydride and triasulfuron.

    PubMed Central

    Persans, M W; Schuler, M A

    1995-01-01

    Cytochrome P450 monooxygenases play paramount roles in the detoxification of herbicides as well as in the synthesis of lignins, flavonoids, and phenolic acids. Biochemical analysis of triasulfuron metabolism in maize (Zea mays) seedlings has demonstrated that the P450(s) responsible for detoxification of this herbicide is induced by naphthalic anhydride (NA), a plant safener, and by triasulfuron, the herbicide itself. Induction studies conducted with seedlings of different ages suggest that two separate response pathways modulate this P-450 activity. Induction by NA is independent of the developmental age of the seedlings up to 6.5 d; induction by triasulfuron is tightly modulated with respect to developmental age in that triasulfuron metabolism can be induced by triasulfuron in young (2.5 d) but not older (6.5 d) seedlings. Induction by NA administered in combination with triasulfuron synergistically enhances triasulfuron metabolism in younger seedlings to levels substantially above that obtained with either herbicide or safener treatment alone. In older seedlings, NA plus triasulfuron treatment induces triasulfuron metabolism to only the level of NA treatment alone, indicating again that the induction cascade responding to triasulfuron is nonfunctional in later development. MnCl2 studies indicate that the triasulfuron insensitivity of older seedlings does not result from a general limitation in the inducibility of this P-450 detoxification system but rather from specific limitations in the triasulfuron-response pathway. PMID:8539299

  1. Water absorption of poly(methyl methacrylate) containing 4-methacryloxyethyl trimellitic anhydride.

    PubMed

    Unemori, Masako; Matsuya, Yoko; Matsuya, Shigeki; Akashi, Akane; Akamine, Akifumi

    2003-04-01

    The amount of water absorption of poly(methyl methacrylate) (PMMA) containing 0, 1, 3 and 5 wt% of an adhesive monomer, 4-methacryloxyethyl trimellitic anhydride (4-META), was measured at 7 degrees C, 37 degrees C and 60 degrees C. After the water uptake reached equilibrium in specimens, they were desorbed to obtain a constant value and the absorption process was repeated. Mass changes in the second desorption were recorded for the storage temperatures of 37 degrees C and 60 degrees C. Multiple regression analyses were conducted on three independent variables, 4-META concentration, storage temperature and absorption-desorption cycle. A statistically significant relationship was found between the maximum water uptake and 4-META concentration, while there was no relationship between the maximum water uptake and diffusion coefficient obtained using the Fick's law. The negative relationship in the latter did not support the free space theory. The significant and positive relationship between the maximum water uptake and 4-META concentration demonstrates that water molecules diffuse through the formation of a hydrogen bond at polar sites. The maximum water uptake was not influenced by temperature, while the diffusion coefficient increased with the rise in temperature. The activation energy was 41-47 and 50-53 kJ/mol in the first and second absorption tests, respectively.

  2. Kaolinite Nanocomposite Platelets Synthesized by Intercalation and Imidization of Poly(styrene-co-maleic anhydride)

    PubMed Central

    Samyn, Pieter; Schoukens, Gustaaf; Stanssens, Dirk

    2015-01-01

    A synthesis route is presented for the subsequent intercalation, exfoliation and surface modification of kaolinite (Kln) by an imidization reaction of high-molecular weight poly(styrene-co-maleic anhydride) or SMA in the presence of ammonium hydroxide. In a first step, the intercalation of ammonolyzed SMA by guest displacement of intercalated dimethylsulfoxide has been proven. In a second step, the imidization of ammonolyzed SMA at 160 °C results in exfoliation of the kaolinite layers and deposition of poly(styrene-co-maleimide) or SMI nanoparticles onto the kaolinite surfaces. Compared with a physical mixture of Kln/SMI, the chemically reacted Kln/SMI provides more efficient exfoliation and hydrogen bonding between the nanoparticles and the kaolinite. The kaolinite nanocomposite particles are synthesized in aqueous dispersion with solid content of 65 wt %. The intercalation and exfoliation are optimized for a concentration ratio of Kln/SMI = 70:30, resulting in maximum intercalation and interlayer distance in combination with highest imide content. After thermal curing at 135 °C, the imidization proceeds towards a maximum conversion of the intermediate amic acid moieties. The changes in O–H stretching and kaolinite lattice vibrations have been illustrated by infrared and FT-Raman spectroscopy, which allow for a good quantification of concentration and imidization effects. PMID:28793445

  3. Effects of difructose anhydride III (DFA III) administration on rat intestinal microbiota.

    PubMed

    Minamida, Kimiko; Shiga, Kazuki; Sujaya, I Nengah; Sone, Teruo; Yokota, Atsushi; Hara, Hiroshi; Asano, Kozo; Tomita, Fusao

    2005-03-01

    The effects of difructose anhydride III (di-D-fructofuranose-1,2':2,3'-dianhydride; DFA III) administration (3% DFA III for 4 weeks) on rat intestinal microbiota were examined using denaturing gradient gel electrophoresis (DGGE). According to DGGE profiles, the number of bacteria related to Bacteroides acidofaciens and uncultured bacteria within the Clostridium lituseburense group decreased, while that of bacteria related to Bacteroides vulgatus, Bacteroides uniformis and Ruminococcus productus increased in DFA III-fed rat cecum. In the cecal contents of DFA III-fed rats, a lowering of pH and an increase in short chain fatty acids (SCFAs), especially acetic acid, were observed. The DFA III-assimilating bacterium, Ruminococcus sp. M-1, was isolated from the cecal contents of DFA III-fed rats. The strain had 98% similarity with R. productus ATCC 27340T (L76595), and mainly produced acetic acid. These results confirmed that the bacteria harmful to host health were not increased by DFA III administration. Moreover, DFA III stimulated the growth of Ruminococcus sp. M-1 producing acetic acid, which may alter the intestinal microbiota towards a healthier composition. It is expected that DFA III would be a new candidate as a prebiotic.

  4. Cantharidin and Its Anhydride-Modified Derivatives: Relation of Structure to Insecticidal Activity

    PubMed Central

    Sun, Wenbo; Liu, Zhongyi; Zhang, Yalin

    2013-01-01

    Cantharidin is a natural compound of novel structure with ideal insecticidal activity. However, the relationship of structure to insecticidal activity of cantharidin and its derivatives has not been ever clarified. To explore what determines the insecticidal activity structurally of cantharidin-related compounds, two series target compounds 6 and 7 were synthesized by replacing the anhydride ring of norcantharidin with an aromatic amine or fatty amine with different electron density, respectively. The structures of these compounds were characterized by 1H NMR, 13C NMR and HRMS-ESI. A bioassay showed that compounds 6 (a–m) lacked any larvicidal activity against Plutella xylostella; whereas their ring-opened partners 7 (a–m) provided a variety of larvicidal activities against P. xylostella, and compound 7f indicated the highest larvicidal activity with LC50 value of 0.43 mM. The present work demonstrated that the form of the compound (cyclic or ring-opened) or their ability to hydrolyze facilely was the key to determine whether it exhibits larvicidal activity. Moreover, it revealed that the improvement of insecticidal activity required a reasonable combination of both aliphatic amide and aromatic amide moieties, and the type of substituent Y on the aniline ring was critical. PMID:23344017

  5. Gelatinization and pasting properties of rice starch modified with 2-octen-1-ylsuccinic anhydride.

    PubMed

    Shih, Fred F; Daigle, Kim W

    2003-02-01

    Rice starch was modified with various levels of 2-octen-1-ylsuccinic anhydride (OSA). Treatments with OSA at 3, 5, and 10% resulted in starch derivatives with 0.016, 0.033, and 0.070 degrees of substitution (DS), respectively. Thermovisco properties of the derivatives were investigated by differential scanning calorimetry (DSC) and rapid visco analysis (RVA). Water content in the sample was found to have a significant effect on the characteristics of the DSC endotherm. Pasting properties of the OSA-starch and the effect of pH and salt on the RVA profiles were also studied. In general, with increased OSA-modification, the starch derivatives swelled and gelatinized at lower temperatures to achieve higher viscosities. Specifically, based on DSC analysis at 80% water, the peak temperature of gelatinization decreased from 68.5 to 63.2 degrees C as the OSA modification increased in DS from 0 (intact starch) to 0.070. On the other hand, RVA results indicate that, for samples undergoing similar increase in OSA modification, the pasting temperature decreased from 88.7 to 51.5 degrees C and the peak viscosity increased from 668 to 6822 cP.

  6. Highly carbonylated cellulose nanofibrous membranes utilizing maleic anhydride grafting for efficient lysozyme adsorption.

    PubMed

    Ma, Juncheng; Wang, Xueqin; Fu, Qiuxia; Si, Yang; Yu, Jianyong; Ding, Bin

    2015-07-22

    Construction of adsorptive materials for simple, efficient, and high-throughput adsorption of proteins is critical to meet the great demands of highly purified proteins in biotechnological and biopharmaceutical industry; however, it has proven extremely challenging. Here, we report a cost-effective strategy to create carbonyl groups surface-functionalized nanofibrous membranes under mild conditions for positively charged protein adsorption. Our approach allows maleic anhydride to in situ graft on cellulose nanofibrous membranes (CMA) to construct adsorptive membranes with large surface area and tortuous porous structure. Thereby, the resultant CMA membranes exhibited high adsorption capacity of 160 mg g(-1), fast equilibrium within 12 h, and good reversibility to lysozyme. Moreover, the dynamic adsorption was performed under low pressure-drops (750 Pa), with a relatively high saturation adsorption amount of 118 mg g(-1), which matched well with the requirements for proteins purification. Considering the excellent adsorption performance of the as-prepared adsorptive membranes, this simple and intriguing approach may pave a way for the design and development of robust and cost-effective adsorption membranes to meet the great demands for fast and efficient adsorption of positively charged proteins.

  7. Immobilization of modified papain with anhydride groups on activated cotton fabric.

    PubMed

    Xue, Yong; Nie, Huali; Zhu, Limin; Li, Shubai; Zhang, Haitao

    2010-01-01

    Papain (EC 3.4.22.2) has been chemically modified using two novel reagents including different anhydrides of 1,2,4-benzenetricarboxylic and pyromellitic acids. Then, the modified papain was immobilized on the activated cotton fabric by a two-step method. The number of free amino groups in the modified protein was investigated through the 2,4,6-trinitrobenzenesulfonic acid method. Energy dispersive spectrometer was used to characterize papain immobilization. Some parameters of both modified and native papain immobilized on cotton fabric, such as optimum temperature, optimum pH, and the stabilities for reservation in various detergents were studied and compared. The resultant papain had its optimum pH shifted from 6.0 to 9.0. Compared with immobilized native papain, the thermal stability and the resistance to alkali and washing detergent of immobilized modified enzyme were improved considerably. When the concentration of detergent was 20 mg/ml, the activity of the immobilized pyromellitic papain retained about 40% of its original activity, whereas the native papain was almost inhibited. This work demonstrated that the cotton fabric immobilized modified papain has potential applications in the functional textiles field.

  8. Effect of Persimmon Leaf Extract on Phthalic Anhydride-induced Allergic Response in Mice

    PubMed Central

    Mok, Ji Ye; Jeon, In Hwa; Cho, Jung-Keun; Park, Ji Min; Kim, Hyeon Soo; Kang, Hyun Ju; Kim, Hyung Soon; Jang, Seon Il

    2012-01-01

    The purpose of this study was to investigate the anti-allergy activities of persimmon leaf extract (PLE) on a phthalic anhydride (PA)-induced allergic mouse model. A human leukemic mast cell line (HMC-1) was used to examine the inhibitory activity of PLE on the histamine release by human leukemic mast cells. PLE inhibited histamine release from HMC-1 cells in response to cross-linkage of high-affinity IgE receptor-α (FcεRIα). Additionally, a PA-induced allergic mouse model was used to investigate the effects of PLE in vivo. Mice were orally administrated with or without PLE of single dose (250 mg/kg/day) for 31 days. Oral intake of PLE significantly inhibited passive cutaneous reactions. Oral administration of PLE to PA-induced allergic mice also led to a striking suppression of the development of contact dermatitis, ear swelling and lymph node weight. In addition, PA-specific IL-4 production of draining lymph node cells was markedly diminished by PLE oral administration, but not IFN-γ. Furthermore, PLE treatment suppressed PA-induced thymus and activation-regulated chemokine (CCL17) and cutaneous T cell-attracting chemokine (CCL27) expressions in ear tissues. Based on these results, we suggest that PLE may have therapeutic potential as an effective material for management of irritant contact dermatitis or related inflammatory diseases. PMID:24471058

  9. Microwave measurements of the spectra and molecular structure for phthalic anhydride

    NASA Astrophysics Data System (ADS)

    Pejlovas, Aaron M.; Sun, Ming; Kukolich, Stephen G.

    2014-05-01

    The microwave rotational spectrum for phthalic anhydride (PhA) has been measured in the 4-14 GHz microwave region using a pulsed-beam Fourier transform (PBFT) Flygare-Balle type microwave spectrometer. Initially, the molecular structure was calculated using Gaussian 09 suite with mp2/6-311++G** basis and the calculations were used in predicting spectra for the measured isotopologues. The experimental rotational transition frequencies were measured and used to calculate the rotational and centrifugal distortion constants. The rotational constants for the normal isotopologue, four unique 13C substituted isotopologues and two 18O isotologues, were used in a least squares fit to determine nearly all structural parameters for this molecule. Since no substitutions were made at hydrogen sites, the calculated positions of the hydrogen atoms relative to the bonded carbon atoms were used in the structure determination. The rotational constants for the parent isotopologue were determined to be A = 1801.7622(9) MHz, B = 1191.71816(26) MHz, C = 717.44614(28) MHz. Small values for the centrifugal distortion constants were obtained; DJ = 0.0127 kHz, DJK = 0.0652 kHz, and DK = -0.099 kHz, indicating a fairly rigid structure. The structure of PhA is planar with a negative inertial defect of Δ = -0.154 amu Å2. Structural parameters from the mp2 and DFT calculations are in quite good agreement with measured parameters.

  10. Separation of maleic anhydride grafted polypropylene using multidimensional high-temperature liquid chromatography.

    PubMed

    Prabhu, K N; Macko, T; Brüll, R; Remerie, K; Tacx, J; Garg, P; Ginzburg, A

    2016-04-08

    Functionalization addresses a property gap of polyolefins and opens new perspectives due to improved surface properties in applications like composites (e.g., glass fiber reinforced polypropylene) and anti-corrosive coatings for metals. Various techniques have been developed to characterize functionalized polyolefins, yet no analytical approach addressing their chemical heterogeneity exists. Using High Temperature Size Exclusion Chromatography (HT-SEC) coupled to infrared spectroscopy we could show for two model samples of polypropylene grafted maleic anhydride (PP-g-MA), differing in their nominal MA content, that the grafting density increases with decreasing molar mass. Crystallization Analysis Fractionation (CRYSTAF) does not enable to separate these samples according to their composition to the extent required. Yet, when using High Temperature High Performance Liquid Chromatography (HT-HPLC), with either silica gel or Mica as stationary phase and a gradient mobile phase, a deformulation into a grafted and a non-grafted fraction could be achieved. This was confirmed by analyzing the eluted fractions by infrared spectroscopy. Hyphenating the separation according to composition with a separation according to molar mass (HT-HPLC x HT-SEC) enabled for the first time to reveal the bivariate distribution of PP-g-MA with regard to the molar mass and composition. Using on-line infrared detection quantitative information on the compositional and molar mass parameters of the individual fractions could be obtained. Copyright © 2016 Elsevier B.V. All rights reserved.

  11. Effect of acetonitrile on stability of disperse phase of solutions of alkenylsuccinic anhydride in xylene

    SciTech Connect

    El'Shine, A.I.; Grichenko, A.A.

    1984-03-01

    This article reports on work directed toward accelerating the alkenylsuccinic anhydride (ASA) solution cleanup operation by the use of acetonitrile. ASA is an intermediate in the production of the widely used ashless succinimide additives for motor oils. The byproducts that are formed in ASA production, finely dispersed tarry precipitates with a complex composition, contaminate the end product. The stability of the dispersed system in a solution of the ASA in xylene (1:1) was evaluated from the rate at which the tarry products settled out, with and without the addition of acetonitrile, as determined by measurements of the height of the column of clarified liquid as a function of the settling time. The results indicate that acetonitrile, which is highly polar, reduces the stability of the dispersed phase in the ASA solution by a factor of 1.5-2. It is recommended that the quantity of acetonitrile added to the ASA solution should not be greater than 12% by weight, since with larger amounts, the ASA forms a new phase because of its limited solubility in the mixture of xylene and acetonitrile. Acetonitrile does not require any additional equipment, and it does not give any difficulty in the subsequent operation of stripping the solvent from the purified ASA, as the acetonitrile has low boiling point (81.6/sup 0/C) and has a good solubility in xylene.

  12. Four-year evaluation of workers exposed to trimellitic anhydride. A brief report

    SciTech Connect

    McGrath, K.G.; Roach, D.; Zeiss, C.R.; Patterson, R.

    1984-09-01

    In a four-year clinical, immunologic, and environmental study of trimellitic anhydride (TMA) exposure in a single plant, 20 workers exposed to TMA powder were evaluated in 1979 and a total of 32 workers were evaluated from 1979 to 1983. Two distinct groups emerged before and after workplace control improvements were made in 1979. Seventeen of the original 20 workers were available for longitudinal study through 1983. Annual clinical evaluations and serum radioimmunoassays for total antibody binding and specific IgE binding to 125I TM-HSA (human serum albumin) were performed on all 32 workers. In 1979, six workers had antibody against TM-HSA, three had the late respiratory systemic syndrome, and two had TMA-induced allergic rhinitis or allergic rhinitis and asthma. One worker had antibody against TM-HSA without illness. Fifteen additional workers were evaluated longitudinally after institution of several workplace control measures. Four of these 15 workers had TMA exposure prior to environmental improvement and joined the study in 1982. The remaining 11 workers joined the study in 1982 and had at least two years of TMA exposure in the modified workplace. None of these 11 workers developed a TMA-induced immunologic syndrome or significant total or specific IgE antibody binding to 125I TM-HSA.

  13. Dodecenylsuccinic anhydride derivatives of gum karaya (Sterculia urens): preparation, characterization, and their antibacterial properties.

    PubMed

    Padil, Vinod Vellora Thekkae; Senan, Chandra; Černík, Miroslav

    2015-04-15

    Esterifications of the tree-based gum, gum karaya (GK), using dodecenylsuccinic anhydride (DDSA) were carried out in aqueous solutions. GK was deacetylated using alkali treatment to obtain deacetylated gum karaya (DGK). The DGK and its DDSA derivative were characterized using gel permeation chromatography/multiangle laser light scattering (GPC/MALLS), attenuated total reflectance-Fourier transform infrared spectroscopy (ATR-FTIR), scanning electron microscopy (SEM), proton nuclear magnetic resonance spectroscopy ((1)H NMR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) analysis, and rheological studies. The degree of substitution was found to be 10.25% for DGK using (1)H NMR spectroscopy. The critical aggregation concentration of DDSA-DGK was determined using dye solubilization and surface tension methods. The antibacterial activity of the DDSA-DGK derivative was then investigated against Gram-negative Escherichia coli and Pseudomonas aeruginosa and Gram-positive Staphylococcus aureus. The DDSA-DGK derivative has the potential for use as a stabilizing agent in food and nonfood applications. It can also be developed as an antibacterial agent.

  14. Structural properties of pepsin-solubilized collagen acylated by lauroyl chloride along with succinic anhydride.

    PubMed

    Li, Conghu; Tian, Zhenhua; Liu, Wentao; Li, Guoying

    2015-10-01

    The structural properties of pepsin-solubilized calf skin collagen acylated by lauroyl chloride along with succinic anhydride were investigated in this paper. Compared with native collagen, acylated collagen retained the unique triple helix conformation, as determined by amino acid analysis, circular dichroism and X-ray diffraction. Meanwhile, the thermostability of acylated collagen using thermogravimetric measurements was enhanced as the residual weight increased by 5%. With the temperature increased from 25 to 115 °C, the secondary structure of native and acylated collagens using Fourier transform infrared spectroscopy measurements was destroyed since the intensity of the major amide bands decreased and the positions of the major amide bands shifted to lower wavenumber, respectively. Meanwhile, two-dimensional correlation spectroscopy revealed that the most sensitive bands for acylated and native collagens were amide I and II bands, respectively. Additionally, the corresponding order of the groups between native and acylated collagens was different and the correlation degree for acylated collagen was weaker than that of native collagen, suggesting that temperature played a small influence on the conformation of acylated collagen, which might be concluded that the hydrophobic interaction improved the thermostability of collagen.

  15. Effect of maleic anhydride on the damping property of magnetorheological elastomers

    NASA Astrophysics Data System (ADS)

    Fan, Y. C.; Gong, X. L.; Jiang, W. Q.; Zhang, W.; Wei, B.; Li, W. H.

    2010-05-01

    In this study, maleic anhydride (MA) was selected as the compatibilizer to modify the interfaces of magnetorheological elastomers (MREs) for improving the damping property. Several samples of MREs with different contents of MA were prepared. The content of bound-rubber was measured by the extraction method. The microstructures were observed by using an environmental scanning electron microscope (SEM). The dynamic performances of these samples, including shear storage modulus, loss factor and MR effect were measured with a modified dynamic mechanical analyzer (DMA). The tensile strength was tested by using an electronic tensile machine. The experimental results indicate that both the content of bound-rubber and the compatibility between the magnetic particles and rubber matrix were enhanced with the increase of MA. The enhancement of the bond between the two phases resulted in different mechanical properties: the increase of shear storage modulus; the reduction of the loss factor; the stability improvement of the loss factor; the enhancement of the tensile strength; and the reduction of the MR effect.

  16. Cantharidin and its anhydride-modified derivatives: relation of structure to insecticidal activity.

    PubMed

    Sun, Wenbo; Liu, Zhongyi; Zhang, Yalin

    2012-12-20

    Cantharidin is a natural compound of novel structure with ideal insecticidal activity. However, the relationship of structure to insecticidal activity of cantharidin and its derivatives has not been ever clarified. To explore what determines the insecticidal activity structurally of cantharidin-related compounds, two series target compounds 6 and 7 were synthesized by replacing the anhydride ring of norcantharidin with an aromatic amine or fatty amine with different electron density, respectively. The structures of these compounds were characterized by 1H NMR, 13C NMR and HRMS-ESI. A bioassay showed that compounds 6 (a-m) lacked any larvicidal activity against Plutella xylostella; whereas their ring-opened partners 7 (a-m) provided a variety of larvicidal activities against P. xylostella, and compound 7f indicated the highest larvicidal activity with LC(50) value of 0.43 mM. The present work demonstrated that the form of the compound (cyclic or ring-opened) or their ability to hydrolyze facilely was the key to determine whether it exhibits larvicidal activity. Moreover, it revealed that the improvement of insecticidal activity required a reasonable combination of both aliphatic amide and aromatic amide moieties, and the type of substituent Y on the aniline ring was critical.

  17. Analysis of octenylsuccinate rice and tapioca starches: Distribution of octenylsuccinic anhydride groups in starch granules.

    PubMed

    Whitney, Kristin; Reuhs, Bradley L; Ovando Martinez, Maribel; Simsek, Senay

    2016-11-15

    Characterization of the fine structure of octenylsuccinic anhydride (OSA) starch would lead to a better understanding of functional properties. OSA rice and tapioca starches were analyzed using microscopy, liquid chromatography and nuclear magnetic resonance. Chain length distribution of amylopectin changed significantly (P<0.05) after OSA esterification. Weight averaged degree of polymerization (DPw) decreased significantly (P<0.05) from 16.47 to 13.29 and from 14.87 to 12.47 in native and OSA rice and tapioca starches, respectively. The chain length distribution of pure amylopectin fractions suggested that OSA groups were not present in the amylopectin portion of the starch. (1)H NMR analysis of pure amylose and amylopectin fractions indicated that OSA substitution was present only in amylose fractions of rice and tapioca starches. Esterification with 3% OSA results in starch that has OSA substituted mainly on amylose chains or possibly on amylopectin chains that have been hydrolyzed from the amylopectin molecules during esterification. Published by Elsevier Ltd.

  18. Nano-encapsulation of coenzyme Q10 using octenyl succinic anhydride modified starch.

    PubMed

    Cheuk, Sherwin Y; Shih, Frederick F; Champagne, Elaine T; Daigle, Kim W; Patindol, James A; Mattison, Christopher P; Boue, Stephen M

    2015-05-01

    Octenyl succinic anhydride modified starch (OSA-ST) was used to encapsulate coenzyme Q10 (CoQ10). CoQ10 was dissolved in rice bran oil and incorporated into an aqueous OSA-ST solution. High pressure homogenisation of the mixture was conducted at 170 MPa for 56 cycles. The resulting emulsion had a particle size range of 200-300 nm and the absolute zeta potential varied between 8.4 and 10.6 mV. CoQ10 retention of the emulsion and freeze dried products, determined by a hexane rinse, was 98.2%. Reconstitution of the freeze dried product in Mcllvaine citrate-phosphate buffers with pH values of 3-5 and temperatures at 4 and 25 °C had very little effect on the range and distribution of the nanoparticles' size. The inflection point of the zeta potential and pH plot occurred at the first pKa of succinic acid (pH 4.2), indicating succinate as the main influence over zeta potential.

  19. Effect of the degree of substitution of octenyl succinic anhydride-banana starch on emulsion stability.

    PubMed

    Bello-Pérez, Luis A; Bello-Flores, Christopher A; Nuñez-Santiago, María del Carmen; Coronel-Aguilera, Claudia P; Alvarez-Ramirez, J

    2015-11-05

    Banana starch was esterified with octenylsuccinic anhydride (OSA) at different degree substitution (DS) and used to stabilize emulsions. Morphology, emulsion stability, emulsification index, rheological properties and particle size distribution of the emulsions were tested. Emulsions dyed with Solvent Red 26 showed affinity for the oil phase. Backscattering light showed three regions in the emulsion where the emulsified region was present. Starch concentration had higher effect in the emulsification index (EI) than the DS used in the study because similar values were found with OSA-banana and native starches. However, OSA-banana presented greater stability of the emulsified region. Rheological tests in emulsions with OSA-banana showed G'>G" values and low dependence of G' with the frequency, indicating a dominant elastic response to shear. When emulsions were prepared under high-pressure conditions, the emulsions with OSA-banana starch with different DS showed a bimodal distribution of particle size. The emulsion with OSA-banana starch and the low DS showed similar mean droplet diameter than its native counterpart. In contrast, the highest DS led to the highest mean droplet diameter. It is concluded that OSA-banana starch with DS can be used to stabilize specific emulsion types.

  20. Studies in iridoid synthesis. Chemoselective transformations of cis-1,2,4,6-tetrahydrophthalic anhydride.

    PubMed

    Stevens, Anne T; Bull, James R; Chibale, Kelly

    2008-02-07

    In the course of synthetic studies towards the development of diastereoselective routes to secoiridoid aglycones, cis-1,2,4,6-tetrahydrophthalic anhydride was transformed into the corresponding lactone cis-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one, which served as a key precursor for a variety of chemoselective synthetic manipulations. Unsuccessful formylation of an ester intermediate resulted in a (E/Z) mixture of vinyl alcohols which were protected as acetates and as a single p-methoxybenzyl (PMB) ether (E) isomer. Dihydroxylation of the cyclohexene motif using OsO(4) led to the unexpected deprotection of the PMB ether. On the other hand, successful formylation of a suitably silyl protected lactonised intermediate was achieved using tert-butoxybis(dimethylamino)methane, or Bredereck's reagent. Tetrabutylammonium fluoride (TBAF) deprotection of a methoxyethoxymethyl (MEM)-ether intermediate serendipitously afforded an approximately 1 : 1 mixture of pyrano-pyranones, which are products of a seldom encountered intramolecular Michael addition, using an oxygen donor, to the terminus of an alpha,beta-unsaturated system, followed by beta-elimination of the MEM moiety.

  1. Structure of associates of vinyl molecules and maleic anhydride in CCl4 solution

    NASA Astrophysics Data System (ADS)

    Zaitseva, V. V.; Tyurina, T. G.; Shtonda, A. V.; Zaitsev, S. Yu.

    2012-04-01

    The self-association of styrene, acrylonitrile, methylmethacrylate, N-vinylpyrrolidone, and maleic anhydride molecules is considered in dependence on the nature of the monomer, i.e., on the conjugation between functional groups. The AM1, Hartree-Fock (RHF), and density functional theory (DFT) methods of calculation are used in our investigations. Charge distributions on the atoms of interacting groups and contributions from overlapping molecular orbitals to the energy of formation of self-associates are found. The calculated parameters are compared with experimental data on absorption band shifts in IR spectra and on chemical shifts ΔH and ΔC for the hydrogen and carbon atoms of =CH, =CH2, C=O groups of bound molecules in 1H and 13C NMR spectra. The formation of π-H, CH…O, and CH…N bonds is proved. Analysis of CCl4/monomer dependences shows that dimers are present in dilute solutions, while the presence of trimers in concentrated solutions cannot be excluded. Self-association constants are determined along with the degree of self-association, which lies within the range of 40-60% for 50 mol% of a monomer in solution.

  2. Position of modifying groups on starch chains of octenylsuccinic anhydride-modified waxy maize starch.

    PubMed

    Bai, Yanjie; Kaufman, Rhett C; Wilson, Jeff D; Shi, Yong-Cheng

    2014-06-15

    Octenylsuccinic anhydride (OSA)-modified starches with a low (0.018) and high (0.092) degree of substitution (DS) were prepared from granular native waxy maize starch in aqueous slurry. The position of OS substituents along the starch chains was investigated by enzyme hydrolysis followed by chromatographic analysis. Native starch and two OS starches with a low and high DS had β-limit values of 55.9%, 52.8%, and 34.4%, respectively. The weight-average molecular weight of the β-limit dextrin from the OS starch with a low DS was close to that of the β-limit dextrin from native starch but lower than that of the β-limit dextrin from the OS starch with a high DS. Debranching of OS starches was incomplete compared with native starch. OS groups in the OS starch with a low DS were located on the repeat units near the branching points, whereas the OS substituents in the OS starch with a high DS occurred both near the branching points and the non-reducing ends. Copyright © 2013 Elsevier Ltd. All rights reserved.

  3. Reaction of octenylsuccinic anhydride with a mixture of granular starch and soluble maltodextrin.

    PubMed

    Bai, Yanjie; Shi, Yong-Cheng

    2013-11-06

    The reaction of octenylsuccinic anhydride (OSA) with a mixture of granular waxy maize starch and soluble maltodextrin was investigated. OSA was reacted with a 1:1 (w/w) mixture of the granular starch and maltodextrin at OSA levels of 1.5, 3, 9, and 15% (wt% based on starch weight). After the first 0.5h of the reaction, degree of substitution (DS) on maltodextrin reached 0.021, 0.030, 0.080, and 0.10 for 1.5, 3, 9, and 15% OSA, respectively, whereas DS for granular starch was only 0.0020, 0.0087, 0.014, and 0.016. At 2h of the reaction, the bound OS ratio of maltodextrin to granular starch was 10.8 when OSA concentration was 1.5% and the ratio decreased to ca. 5 at higher OSA concentrations. OSA preferred to react with maltodextrin than semi-crystalline granular starch when both existed in the system. OSA reacted with maltodextrin at a much faster rate and to a greater extent than with granular starch, but a significant amount of OSA reacted with granular starch at 3-15% OSA concentrations.

  4. Polymer flooding

    SciTech Connect

    Littmann, W.

    1988-01-01

    This book covers all aspects of polymer flooding, an enhanced oil recovery method using water soluble polymers to increase the viscosity of flood water, for the displacement of crude oil from porous reservoir rocks. Although this method is becoming increasingly important, there is very little literature available for the engineer wishing to embark on such a project. In the past, polymer flooding was mainly the subject of research. The results of this research are spread over a vast number of single publications, making it difficult for someone who has not kept up-to-date with developments during the last 10-15 years to judge the suitability of polymer flooding to a particular field case. This book tries to fill that gap. An indispensable book for reservoir engineers, production engineers and lab. technicians within the petroleum industry.

  5. Semiconducting polymers

    NASA Astrophysics Data System (ADS)

    Hermann, A. M.

    A review is presented of the electrical properties of those polymers whose conductivities occupy the middle ground between polymeric insulators and polymeric superconductors. Attention is confined to polymers in which conduction occurs through electronic, rather than ionic, transport. Four classes of semiconductors are discussed: (1) highly-conjugated polymers, including those formed by pyrolysis; (2) polymeric charge-transfer complexes and radical-ion salts; (3) organometallic polymeric semiconductors; and (4) composite polymer systems containing carbon or other highly conducting media. The possible applications discussed include cathodes in solid-state metal/halogen primary batteries, cathodes in lithium/poly-p-phenylene or polyacetylene secondary batteries, conductive coatings and epoxies, and chemical sensing agents. Other applications are Peltier cooling devices, pressure transducers, photovoltaic devices, infrared radiation detectors, and switches and resistors.

  6. Organometallic Polymers.

    ERIC Educational Resources Information Center

    Carraher, Charles E., Jr.

    1981-01-01

    Reactions utilized to incorporate a metal-containing moiety into a polymer chain (addition, condensation, and coordination) are considered, emphasizing that these reactions also apply to smaller molecules. (JN)

  7. Polymers All Around You!

    ERIC Educational Resources Information Center

    Gertz, Susan

    Background information on natural polymers, synthetic polymers, and the properties of polymers is presented as an introduction to this curriculum guide. Details are provided on the use of polymer products in consumer goods, polymer recycling, polymer densities, the making of a polymer such as GLUEP, polyvinyl alcohol, dissolving plastics, polymers…

  8. Polymers All Around You!

    ERIC Educational Resources Information Center

    Gertz, Susan

    Background information on natural polymers, synthetic polymers, and the properties of polymers is presented as an introduction to this curriculum guide. Details are provided on the use of polymer products in consumer goods, polymer recycling, polymer densities, the making of a polymer such as GLUEP, polyvinyl alcohol, dissolving plastics, polymers…

  9. Cold processed oil-in-water emulsions for dermatological purpose: formulation design and structure analysis.

    PubMed

    Raposo, Sara; Salgado, Ana; Eccleston, Gillian; Urbano, Manuela; Ribeiro, Helena M

    2014-06-01

    The aim of this work is to develop, optimize and characterize cold process emulsions that are stable at acidic pH. The main surfactant was selected according to the hydrophilic lipophilic balance (HLB) concept and surface tension, whereas polymers were selected by viscoelastic measurements and analytical centrifugation. It was showed that the inclusion of methyl vinyl ether/maleic anhydride copolymer crosslinked with decadiene (PVM/MA) increased the storage modulus (G') of the gels (23.9-42.1 Pa) two-fold and the droplet migration decreased from 3.66% to 0.95%/h. Cetrimide was selected as a preservative based on its microbiological results and additional contribution to the stability of the emulsions. Four emulsions were developed that differed by the co-emulsifier used (PEG-20 glyceril laurate and polyglyceryl-4-isostearate) and the glycol (2-methyl-2,4-pentanediol and ethoxydiglycol). Viscoelastic measurements and droplet size/microscopic analysis showed that the structure of PEG-20 glyceril laurate emulsion (η' = 76.0 Pa.s at 0.01 Hz and 32.9 ± 3.7 µm, respectively) was stronger compared to polyglyceryl-4-isostearate (η' = 37.4 Pa.s at 0.01 Hz and 37.8 ± 15.7 µm, respectively). Differential scanning calorimetry (DSC) results were in accordance with the latter and showed that PEG-20 glyceril laurate with 2-methyl-2,4-pentanediol corresponded to the strongest structure (|224.4| W °C g(-1)). This cold process allowed a total production savings of more than 17% when compared to the traditional hot process.

  10. Hydrothermal Synthesis and Processing of Barium Titanate Nanoparticles Embedded in Polymer Films.

    PubMed

    Toomey, Michael D; Gao, Kai; Mendis, Gamini P; Slamovich, Elliott B; Howarter, John A

    2015-12-30

    Barium titanate nanoparticles embedded in flexible polymer films were synthesized using hydrothermal processing methods. The resulting films were characterized with respect to material composition, size distribution of nanoparticles, and spatial location of particles within the polymer film. Synthesis conditions were varied based on the mechanical properties of the polymer films, ratio of polymer to barium titanate precursors, and length of aging time between initial formulations of the solution to final processing of nanoparticles. Block copolymers of poly(styrene-co-maleic anhydride) (SMAh) were used to spatially separate titanium precursors based on specific chemical interactions with the maleic anhydride moiety. However, the glassy nature of this copolymer restricted mobility of the titanium precursors during hydrothermal processing. The addition of rubbery butadiene moieties, through mixing of the SMAh with poly(styrene-butadiene-styrene) (SBS) copolymer, increased the nanoparticle dispersion as a result of greater diffusivity of the titanium precursor via higher mobility of the polymer matrix. Additionally, an aminosilane was used as a means to retard cross-linking in polymer-metalorganic solutions, as the titanium precursor molecules were shown to react and form networks prior to hydrothermal processing. By adding small amounts of competing aminosilane, excessive cross-linking was prevented without significantly impacting the quality and composition of the final barium titanate nanoparticles. X-ray diffraction and X-ray photoelectron spectroscopy were used to verify nanoparticle compositions. Particle sizes within the polymer films were measured to be 108 ± 5 nm, 100 ± 6 nm, and 60 ± 5 nm under different synthetic conditions using electron microscopy. Flexibility of the films was assessed through measurement of the glass transition temperature using dynamic mechanical analysis. Dielectric permittivity was measured using an impedance analyzer.

  11. Evaluation of poly(styrene-alt-maleic anhydride)-ethanol as enteric coating material.

    PubMed

    Lai, Xiaolin; Sun, Chengdong; Tian, Hua; Zhao, Wenjun; Gao, Lin

    2008-03-20

    This study aims at evaluating the potential of SMA-ethanol as enteric coating polymer for erythromycin tablets. SMA-ethanol was synthesized and characterized for physicochemical properties, molecular weight and thermal analysis. Free films were prepared by adding different kinds and amounts of plasticizers, the film surface topography was determined by a SEM, the tensile strength, water vapor transmission rate and moisture absorption were also tested to choose the most promising film. DBP was proved to be the most suitable plasticizer with a best using amount of 20%, such polymer films had low vapor transmission rate and low moisture absorption which were very important to an enteric coating material. The polymer was further characterized for film coating by evaluating the release of erythromycin tablets in vitro, tablets coated with SMA-ethanol can satisfy the drug release requests of USP when the film weight gains were between 4 and 6%; tablets coated with both a subcoat and the polymer showed excellent gastro-resistance, less than 0.2% drug release occurred even with weight gains as less as 2% after 2h exposure to acid (pH 1), while over 90% drug release occurred in pH 6.8 sodium phosphate buffer within 45 min, regardless of weight gains of coating material, moreover, we confirmed that the application of a subcoat could decrease the amount of required coating polymer. In conclusion, the potential use of SMA-ethanol as enteric coating material was demonstrated.

  12. Therapeutic effect of ethyl acetate extract from Asparagus cochinchinensis on phthalic anhydride-induced skin inflammation

    PubMed Central

    Sung, Ji-Eun; Lee, Hyun-Ah; Kim, Ji-Eun; Go, Jun; Seo, Eun-Ji; Yun, Woo-Bin; Kim, Dong-Seob; Son, Hong-Joo; Lee, Chung-Yeoul; Lee, Hee-Seob

    2016-01-01

    Asparagus cochinchinensis has been used to treat various diseases including fever, cough, kidney disease, breast cancer, inflammatory disease and brain disease, while IL-4 cytokine has been considered as key regulator on the skin homeostasis and the predisposition toward allergic skin inflammation. However, few studies have investigated its effects and IL-4 correlation on skin inflammation to date. To quantitatively evaluate the suppressive effects of ethyl acetate extracts of A. cochinchinensis (EaEAC) on phthalic anhydride (PA)-induced skin inflammation and investigate the role of IL-4 during their action mechanism, alterations in general phenotype biomarkers and luciferase-derived signals were measured in IL-4/Luc/CNS-1 transgenic (Tg) mice with PA-induced skin inflammation after treatment with EaEAC for 2 weeks. Key phenotype markers including lymph node weight, immunoglobulin E (IgE) concentration, epidermis thickness and number of infiltrated mast cells were significantly decreased in the PA+EaEAC treated group compared with the PA+Vehicle treated group. In addition, expression of IL-1β and TNF-α was also decreased in the PA+EaEAC cotreated group, compared to PA+Vehicle treated group. Furthermore, a significant decrease in the luciferase signal derived from IL-4 promoter was detected in the abdominal region, submandibular lymph node and mesenteric lymph node of the PA+EaEAC treated group, compared to PA+Vehicle treated group. Taken together, these results suggest that EaEAC treatment could successfully improve PA-induced skin inflammation of IL-4/Luc/CNS-1 Tg mice, and that IL-4 cytokine plays a key role in the therapeutic process of EaEAC. PMID:27051441

  13. Trimellitic anhydride-conjugated serum albumin activates rat alveolar macrophages in vitro

    PubMed Central

    Valstar, Dingena L; Schijf, Marcel A; Stelekati, Erietta; Nijkamp, Frans P; Bloksma, Nanne; Henricks, Paul AJ

    2006-01-01

    Background Occupational exposure to airborne low molecular weight chemicals, like trimellitic anhydride (TMA), can result in occupational asthma. Alveolar macrophages (AMs) are among the first cells to encounter these inhaled compounds and were previously shown to influence TMA-induced asthma-like symptoms in the Brown Norway rat. TMA is a hapten that will bind to endogenous proteins upon entrance of the body. Therefore, in the present study we determined if TMA and TMA conjugated to serum albumin induced the production of the macrophage mediators nitric oxide (NO), tumour necrosis factor (TNF), and interleukin 6 (IL-6) in vitro using the rat AM cell line NR8383 and primary AMs derived from TMA-sensitized and naïve Brown Norway rats. Methods Cells were incubated with different concentrations of TMA, TMA conjugated to bovine serum albumin (BSA), and BSA as a control for 24 h and the culture supernatant was analyzed for mediator content. Results TMA alone was not able to induce the production of mediators by NR8383 cells and primary AMs from sensitized and sham-treated rats. TMA-BSA, on the contrary, dose-dependently stimulated the production of NO, TNF, and IL-6 by NR8383 cells and of NO and TNF, but not IL-6, by primary AMs independent of sensitization. Conclusion Results suggest that although TMA is a highly reactive compound, conjugation to a suitable protein is necessary to induce mediator production by AMs. Furthermore, the observation that effects of TMA-BSA were independent of sensitization suggests involvement of an immunologically non-specific receptor. In the discussion it is argued that a macrophage scavenger receptor is a likely candidate. PMID:16796737

  14. Difructose anhydride III enhances bioavailability of water-insoluble iron in anemic Vietnamese women.

    PubMed

    Nakamori, Masayo; Hien, Vu Thi Thu; Khan, Nguyen Cong; Lam, Nguyen Thi; Dung, Nguyen Tri; Uotsu, Nobuo; Shiomi, Takuya; Okuhara, Yasuhide; Kise, Mitsuo; Shigematsu, Norihiro; Yamamoto, Shigeru

    2010-01-01

    Difructose anhydride III (DFAIII) is an indigestible disaccharide and has been shown to enhance iron absorption in animal studies; however, the effect has not been investigated in anemic subjects. We investigated the efficacy of co-administration of DFAIII with water-insoluble iron in the treatment of iron deficiency anemia in Vietnamese women. One hundred sixty-eight moderately anemic women (80 g/L

  15. Evaporative Derivatization of Phenols with 2-Sulfobenzoic Anhydride for Detection by MALDI-MS

    PubMed Central

    Yao, Yuanyuan; Wang, Poguang; Giese, Roger

    2014-01-01

    RATIONALE Phenols are an important class of analytes, for example as bioactive environmental contaminants. Towards a goal of improving their detection by MALDI-TOF-MS or MALDI-TOF/TOF-MS, we studied their derivatization with 2-sulfobenzoic anhydride (SBA). We chose SBA for this purpose since it is commercially available, inexpensive, and forms an anionic derivative. METHODS In selected conditions developed here for phenols, a reaction mixture of one or more of such compounds in acetonitrile containing SBA and 4-dimethylaminopyridine (DMAP) is evaporated to a solid, heated at 60°C for 1 h, redissolved in 50% acetonitrile containing matrix, spotted onto a MALDI target, and subjected to negative ion MALDI-TOF/TOF-MS. RESULTS While conventional (solution-phase) reaction of 4-phenylphenol (model analyte) with SBA and DMAP only gave a 47% yield of SBA-tagged 4-phenylphenol, evaporative derivatization as above gave a 96% yield, and 25 pmol (4.3 ng) of 4-phenylphenol could be detected in this way by MALDI-TOF/TOF-MS at S/N = 260, whereas even 1 nmol of the nonderivatized phenol was not detected in the absence of derivatization. A wide range of responses was observed when a mixture of 15 phenols was derivatized, with the higher responses coming from phenols with a pKa value above 9. Without derivatization, phenols with pKa values below 5 were the most readily detected. CONCLUSION Evaporative derivatization with SBA (a convenient reagent) can improve the detection of phenols with relatively high pKa values (above 9) by negative ion MALDI-TOF-MS, and accomplish this in the absence of post-derivatization reaction cleanup. PMID:24519828

  16. Inhibitory Effect of Carnosol on Phthalic Anhydride-Induced Atopic Dermatitis via Inhibition of STAT3

    PubMed Central

    Lee, Do Yeon; Hwang, Chul Ju; Choi, Ji Yeon; Park, Mi Hee; Song, Min Ji; Oh, Ki Wan; Son, Dong Ju; Lee, Seung Hwa; Han, Sang Bae; Hong, Jin Tae

    2017-01-01

    Carnosol is a phenolic antioxidant present in rosemary (Rosmarinus officinalis). It is known for anti-inflammatory effects, analgesic activity and anti-cancer effects. However, no study has been dedicated yet to its effect on atopic dermatitis (AD). Here, we show that carnosol effectively inhibited LPS-induced nitric oxide (NO) generation and expression of inflammatory marker proteins (iNOS and COX-2) in RAW 264.7 cells. In addition, carnosol effectively inhibits the phosphorylation of STAT3 and DNA binding activity in RAW 264.7 cells. Pull down assay and docking model analysis showed that carnosol directly binds to the DNA binding domain (DBD) of STAT3. We next examined the anti-atopic activity of carnosol (0.05 μg/cm2) using 5% Phthalic anhydride (PA)-induced AD model in HR1 mice. Carnosol treatment significantly reduced 5% PA-induced AD like skin inflammation in skin tissues compared with control mice. Moreover, carnosol treatment inhibits the expression of iNOS and COX-2 in skin tissue. In addition, the levels of TNF-α, IL-1β, and Immunoglobulin-E in blood serum was significantly decreased in carnosol treated mice compared with those of 5% PA treated group. Furthermore, the activation of STAT3 in skin tissue was decreased in carnosol treated mice compared with control mice. In conclusion, these findings suggest that carnosol exhibited a potential anti-AD activity by inhibiting pro-inflammatory mediators through suppression of STAT3 activation via direct binding to DBD of STAT3. PMID:28655070

  17. Elucidation of substituted ester group position in octenylsuccinic anhydride modified sugary maize soluble starch.

    PubMed

    Ye, Fan; Miao, Ming; Huang, Chao; Lu, Keyu; Jiang, Bo; Zhang, Tao

    2014-12-03

    The octenylsuccinic groups in esterification-modified sugary maize soluble starches with a low (0.0191) or high (0.0504) degree of substitution (DS) were investigated by amyloglucosidase hydrolysis followed by a combination of chemical and physical analysis. The results showed the zeta-potential remained at approximately the same value regardless of excessive hydrolysis. The weight-average molecular weight decreased rapidly and reached 1.22 × 10(7) and 1.60 × 10(7) g/mol after 120 min for low-DS and high-DS octenylsuccinic anhydride (OSA) modified starch, respectively. The pattern of z-average radius of gyration as well as particle size change was similar to that of Mw, and z-average radius of gyration decreased much more slowly, especially for high-DS OSA starch. Compared to native starch, two characteristic absorption peaks at 1726.76 and 1571.83 cm(-1) were observed in FT-IR spectra, and the intensity of absorption peaks increased with increasing DS. The NMR results showed that OSA starch had several additional peaks at 0.8-3.0 ppm and a shoulder at 5.56 ppm for OSA substituents, which were grafted at O-2 and O-3 positions in soluble starch. The even distribution of OSA groups in the center area of soluble starch particle has been directly shown under CLSM. Most substitutions were located near branching points of soluble starch particles for a low-DS modified starch, whereas the substituted ester groups were located near branching points as well as at the nonreducing ends in OSA starch with a high DS.

  18. Involvement of inflammatory mediators in the airway responses to trimellitic anhydride in sensitized guinea-pigs.

    PubMed Central

    Hayes, J. P.; Lotvall, J. O.; Barnes, P. J.; Newman Taylor, A. J.; Chung, K. F.

    1992-01-01

    1. We examined the effect of various pharmacological agents on the acute bronchoconstrictor response and airway microvascular leakage in a model of guinea-pig sensitization to trimellitic anhydride (TMA) a cause of low molecular weight occupational asthma in man. 2. Guinea-pigs were given intradermal injections of 0.1 ml of 0.3% TMA in corn oil; 21-28 days later, anaesthetized guinea-pigs were challenged with TMA conjugated to guinea-pig albumin by tracheal instillation. Changes in lung resistance were measured and airway microvascular leakage was quantified by measuring the extravasation of Evans blue dye into the airway tissue. 3. Sensitized guinea-pig (n = 9 in each group) were pretreated with chlorpheniramine (2.5 mg kg-1, i.v.), WEB 2086 (10 micrograms kg-1, i.v.), BW 4AC (50 mg kg-1, i.p.), nedocromil sodium (2% aerosol for 60 s) or vehicle alone. 4. Pretreatment with chlorpheniramine inhibited both the acute bronchoconstrictor response and the increase in airway microvascular leakage. WEB 2086 and nedocromil sodium partially inhibited the bronchoconstrictor response but had no significant effect on airway microvascular leakage. BW 4AC caused a non-significant reduction of the bronchoconstrictor response and airway microvascular leakage. 5. These results indicate that both the bronchoconstrictor response and the airway microvascular response in this model of sensitization is mediated to a large extent by histamine. PAF but not 5-lipoxygenase products also partially mediates the bronchoconstrictor response but not the airway microvascular leakage. Nedocromil sodium partially inhibits the bronchoconstrictor response only. PMID:1382788

  19. Therapeutic effects of fermented soycrud on phenotypes of atopic dermatitis induced by phthalic anhydride

    PubMed Central

    Sung, Ji-Eun; Kwak, Moon-Hwa; Kim, Ji-Eun; Lee, Young-Ju; Kim, Ro-Ui; Kim, Eun-Ah; Lee, Ga-Young; Kim, Dong-Seob

    2013-01-01

    Atopic dermatitis (AD), which is known as the most common pruritic skin disease, is caused by epidermal barrier dysfunction, allergies, microwave radiation, histamine intolerance, and genetic defects. To investigate the therapeutic effects of fermented soycrud (FSC) on AD pathology, alteration of AD phenotypes induced by phthalic anhydride (PA) treatment was assessed by ear thickness analysis, measurement of immune-related organ weights, ELISA, and histological and pathological analyses of ICR mice after FSC treatment for 2 weeks. Except for water content, the concentrations of most major components were lower in FSC compared to common tofu (CMT). Thymus and lymph node weights were significantly reduced in ICR mice treated with PA+CMT or PA+FSC, whereas spleen and body weights were maintained. Elevation of ear thickness induced by PA treatment was rapidly diminished in the CMT- and FSC-treated groups, although there was no significant difference between the two groups. Furthermore, significant reduction of epidermal thickness was detected in both the PA+CMT- and PA+FSC-treated groups. However, IgE concentration and dermal thickness were reduced only by PA+FSC treatment, whereas PA+CMT treatment maintained levels comparable to PA+vehicle treatment. The number of infiltrated mast cells was higher in the PA+vehicle-treated group compared to the untreated control. Following CMT or FSC treatment, mast cell infiltration was slightly reduced, although the CMT-treated group showed greater cell numbers. These results indicate that FSC may significantly relieve the phenotypes of AD induced by PA treatment and should be considered as a potential candidate for AD therapy. PMID:23825483

  20. Bee venom acupuncture alleviates trimellitic anhydride-induced atopic dermatitis-like skin lesions in mice.

    PubMed

    Sur, Bongjun; Lee, Bombi; Yeom, Mijung; Hong, Ju-Hee; Kwon, Sunoh; Kim, Seung-Tae; Lee, Hyang Sook; Park, Hi-Joon; Lee, Hyejung; Hahm, Dae-Hyun

    2016-01-29

    Bee venom acupuncture (BVA), a novel type of acupuncture therapy in which purified bee venom is injected into the specific acupuncture point on the diseased part of the body, is used primarily for relieving pain and other musculoskeletal symptoms. In the present study, therapeutic potential of BVA to improve atopic dermatitis, a representative allergic dysfunction, was evaluated in the mouse model of trimellitic anhydride (TMA)-induced skin impairment. Mice were treated with 5% TMA on the dorsal flank for sensitization and subsequently treated with 2% TMA on the dorsum of both ears for an additional 12 days after a 3-day interval. From the 7(th) day of 2% TMA treatment, bilateral subcutaneous injection of BV (BV, 0.3 mg/kg) was performed daily at BL40 acupuncture points (located behind the knee) 1 h before 2% TMA treatment for 5 days. BVA treatment markedly inhibited the expression levels of both T helper cell type 1 (Th1) and Th2 cytokines in ear skin and lymph nodes of TMA-treated mice. Clinical features of AD-like symptoms such as ear skin symptom severity and thickness, inflammation, and lymph node weight were significantly alleviated by BV treatment. BV treatment also inhibited the proliferation and infiltration of T cells, the production of Th1 and Th2 cytokines, and the synthesis of interleukin (IL)-4 and immunoglobulin E (IgE)-typical allergic Th2 responses in blood. The inhibitory effect of BVA was more pronounced at BL40 acupoint than non-acupuncture point located at the base of the tail. These results indicate that BV injection at specific acupuncture points effectively alleviates AD-like skin lesions by inhibiting inflammatory and allergic responses in a TMA-induced contact hypersensitivity mouse model.

  1. Role of mast cell in the late phase of contact hypersensitivity induced by trimellitic anhydride

    PubMed Central

    Chai, Ok Hee

    2015-01-01

    Mast cells are known as effector cells of IgE-mediated allergic responses, but role of mast cells in contact hypersensitivity (CHS) has been considered controversial. In this study, we investigated role of mast cell in trimellitic anhydride (TMA)-induced CHS. The mice were sensitized to TMA on the back and repeatedly challenged with TMA on the left ear at 1-week intervals. The ear after challenge showed biphasic responses. The repetition of TMA challenge shifted in time course of ear response and enlarged the extent of early and late phase reactions in proportion to the frequency of TMA challenges in C57BL/6 mice. In late phase reaction, peak of ear response by single challenge showed at 24 hours after challenge, but the peak by repeat challenges at 8 hours after the last challenge. Number of mast cells and eosinophils per unit area increased in proportion to frequency of TMA challenges. However, mast cell-deficient WBB6F1/J-KitW/KitW-v mice developed the late phase reaction without the early phase reaction. The repetition of TMA challenge shifted in time course of ear response and enlarged the extent of ear response and the infiltration of eosinophils. The magnitude of these responses observed according to the frequency of the TMA challenge in mast cell-deficient WBB6F1/J-KitW/KitW-v mice was significantly lower than that in C57BL/6 mice. Also TMA elicited mast cell degranulation and histamine release from rat peritoneal mast cells in a concentration-dependent manner. Conclusively, TMA induces the early and late phase reactions in CHS, and mast cells may be required for TMA-induced CHS. PMID:26770872

  2. Trimellitic anhydride (TMA) dust induces airway obstruction and eosinophilia in non-sensitized guinea pigs.

    PubMed

    Larsen, Christen P; Regal, Jean F

    2002-09-02

    Trimellitic anhydride (TMA) causes asthma after a latency period of sensitization. In non-sensitized humans and animals, limited studies indicate that TMA exposure may also cause symptoms of asthma without a latency period. Our previous studies (J. Pharmacol. Exp. Ther. 296 (2001) 284) in a guinea pig model of TMA-induced asthma demonstrated that sensitization and the complement system were required for eosinophilia. TMA conjugated to guinea pig serum albumin (TMA-GPSA) was used to elicit the response. Since occupational exposure to TMA occurs by inhalation of dust, the present studies determined if exposure to TMA dust in a non-sensitized guinea pig elicited airway obstruction and inflammation, and whether a significantly greater response occurred after a latency period of sensitization. Guinea pigs were intradermally injected with either corn oil (non-sensitized animals) or 30% TMA (sensitized animals). Three weeks later they were challenged by intratracheal insufflation with 1 mg TMA dust or lactose dust (control) using a dry powder delivery device. Pulmonary resistance, dynamic lung compliance, mean arterial blood pressure and heart rate were monitored for 10 min. In non-sensitized guinea pigs, significant increases in pulmonary resistance and decreases in dynamic lung compliance and blood pressure occurred after TMA challenge. In sensitized animals, the same dose of TMA caused significantly greater effects compared to non-sensitized animals. In a separate experiment, cellular infiltration into the lung was determined 24 h after challenge with TMA dust or lactose dust. In both non-sensitized and sensitized animals, eosinophils in the lung tissue were increased after TMA dust challenge compared to controls. Thus, these studies suggest that the response in non-sensitized animals differs depending on whether TMA dust or TMA-GPSA is used to elicit the response. TMA dust elicits significant airway obstruction and eosinophilia in a non-sensitized animal, with even

  3. Polymer inflation

    NASA Astrophysics Data System (ADS)

    Hassan, Syed Moeez; Husain, Viqar; Seahra, Sanjeev S.

    2015-03-01

    We consider the semiclassical dynamics of a free massive scalar field in a homogeneous and isotropic cosmological spacetime. The scalar field is quantized using the polymer quantization method assuming that it is described by a Gaussian coherent state. For quadratic potentials, the semiclassical equations of motion yield a universe that has an early "polymer inflation" phase which is generic and almost exactly de Sitter, followed by an epoch of slow-roll inflation. We compute polymer corrections to the slow-roll formalism, and discuss the probability of inflation in this model using a physical Hamiltonian arising from time gauge fixing. We also show how in this model, it is possible to obtain a significant amount of slow-roll inflation from sub-Planckian initial data, hence circumventing some of the criticisms of standard scenarios. These results show the extent to which a quantum gravity motivated quantization method affects early universe dynamics.

  4. A New Process for Maleic Anhydride Synthesis from a Renewable Building Block: The Gas-Phase Oxidehydration of Bio-1-butanol.

    PubMed

    Pavarelli, Giulia; Velasquez Ochoa, Juliana; Caldarelli, Aurora; Puzzo, Francesco; Cavani, Fabrizio; Dubois, Jean-Luc

    2015-07-08

    We investigated the synthesis of maleic anhydride by oxidehydration of a bio-alcohol, 1-butanol, as a possible alternative to the classical process of n-butane oxidation. A vanadyl pyrophosphate catalyst was used to explore the one-pot reaction, which involved two sequential steps: 1) 1-butanol dehydration to 1-butene, catalysed by acid sites, and 2) the oxidation of butenes to maleic anhydride, catalysed by redox sites. A non-negligible amount of phthalic anhydride was also formed. The effect of different experimental parameters was investigated with chemically sourced 1-butanol, and the results were then confirmed by using genuinely bio-sourced 1-butanol. In the case of bio-1-butanol, however, the purity of the product remarkably affected the yield of maleic anhydride. It was found that the reaction mechanism includes the oxidation of butenes to crotonaldehyde and the oxidation of the latter to either furan or maleic acid, both of which are transformed to produce maleic anhydride.

  5. Design and synthesis of digitally encoded polymers that can be decoded and erased

    PubMed Central

    Roy, Raj Kumar; Meszynska, Anna; Laure, Chloé; Charles, Laurence; Verchin, Claire; Lutz, Jean-François

    2015-01-01

    Biopolymers such as DNA store information in their chains using controlled sequences of monomers. Here we describe a non-natural information-containing macromolecule that can store and retrieve digital information. Monodisperse sequence-encoded poly(alkoxyamine amide)s were synthesized using an iterative strategy employing two chemoselective steps: the reaction of a primary amine with an acid anhydride and the radical coupling of a carbon-centred radical with a nitroxide. A binary code was implemented in the polymer chains using three monomers: one nitroxide spacer and two interchangeable anhydrides defined as 0-bit and 1-bit. This methodology allows encryption of any desired sequence in the chains. Moreover, the formed sequences are easy to decode using tandem mass spectrometry. Indeed, these polymers follow predictable fragmentation pathways that can be easily deciphered. Moreover, poly(alkoxyamine amide)s are thermolabile. Thus, the digital information encrypted in the chains can be erased by heating the polymers in the solid state or in solution. PMID:26006165

  6. Self-healing antimicrobial polymer coating with efficacy in the presence of organic matter

    NASA Astrophysics Data System (ADS)

    Bastarrachea, Luis J.; Goddard, Julie M.

    2016-08-01

    A method to prepare a self-healing, antimicrobial polymer coating that retains efficacy against Escherichia coli O157:H7 in the presence of organic matter is reported. A coating composed of branched polyethyleneimine (PEI) and styrene maleic anhydride copolymer (SMA) was applied to a maleic anhydride functionalized polypropylene support. The chemistry of the polymer coating was designed to impart hydrophobicity due to the styrene subunits, intrinsic antimicrobial character (>99.9% reduction) from the cationic primary amine groups, and enhanced antimicrobial character (> 99.99% reduction) after chlorination of N-halamine forming groups. Antimicrobial effectiveness was demonstrated under conditions of increasing organic load. Up to 500 ppm horse serum, chlorinated coatings retained full antimicrobial character (>99.99% reduction). Even at 50,000 ppm of horse serum, the coating provided ∼90% reduction as prepared, and between ∼75% and ∼80% reduction in the form of N-halamines. Microscopy confirmed no evidence of bacterial adhesion on the coating surface. Finally, the coating exhibited self-healing properties after exposure to acid and alkaline solutions and restoration by heat, as confirmed through spectroscopy from the rebuilding of characteristic chemical bonds. Such robust antimicrobial polymer coatings with efficacy under conditions of increasing organic load may support reducing microbial cross-contamination in food and biomedical industries.

  7. Determination of amines as pentafluoropropionic acid anhydride derivatives in biological samples using liquid chromatography and tandem mass spectrometry.

    PubMed

    Marand, Asa; Karlsson, Daniel; Dalene, Marianne; Skarping, Gunnar

    2004-06-01

    Determination of amines in biological samples as markers of exposure to the amines or the corresponding isocyanates is an important tool for industrial exposure assessment. In this study, a liquid chromatography and tandem mass spectrometry (LC-MS/MS) method for determination of amines in biological samples as perfluorofatty amides derivatives is presented. The method enables determination of diamines such as methylene diamine (MDA), toluene diamine (TDA), naphthalene diamine (NDA), hexamethylene diamine (HDA), isophorone diamine (IPDA), methylenedi(cyclohexylamine)(HMDA) and 4,4'-methylene-(2-chloroaniline)(MOCA) in human urine and plasma. The work-up procedure included hydrolysis of the biological samples with 3 M H(2)SO(4) at 100 degrees C for 16 h and extraction of the amines into toluene, where derivatisation of the amines with perfluorofatty acid anhydride was performed. Following removal of excess reagent and the acid formed and an exchange of solvent, the derivatives were analysed using gradient elution with an acetonitrile/water mobile phase composition and electrospray ionisation (ESI) with multiple reaction monitoring (MRM) of [M - H](-)-->[M - H - 120](-) or [119](-). Several perfluorofatty acid anhydrides were evaluated as derivatisation reagents, but the LC chromatographic properties of the pentafluoropropionic acid anhydride (PFPA) derivatives were favourable. Quantification of amine-PFPA derivatives was performed using deuterium labelled amine-PFPA derivatives as internals standards with good precision and linearity in the investigated range of 0-20 ng ml(-1) urine. The instrumental detection limits for the amine-PFPA derivatives were 0.2-3 fmol for MRM of [M - H](-)-->[119](-) and 0.3-8 fmol for [M - H](-)-->[M - H - 120](-). In 10 urine and 6 plasma samples from workers exposed to isocyanates, determination of TDA and MDA as PFPA derivatives was performed using LC-MS/MS and a reference GC-MS method. No significant difference between the two

  8. Effect of polymer properties and adherend surfaces on adhesion. [titanium, aluminum

    NASA Technical Reports Server (NTRS)

    Dwight, D. W.; Counts, M. E.; Wightman, J. P.

    1975-01-01

    The surface properties associated with good adhesive joints were evaluated in terms of application of adhesive bonding in aerospace technology. The physical and chemical nature was determined of Ti and Al adherend surfaces after various surface treatments, and the effects on fracture surfaces of high temperature aging, and variations in amide, anhydride, and solvent during polymer synthesis. The effects were characterized of (1) high temperature during shear strength testing, (2) fiber-reinforced composites as adherends, (3) acid/base nature of adherends, (4) aluminum powder adhesive filler, and (5) bonding pressure.

  9. Maleic anhydride polypropylene modified cellulose nanofibril polypropylene nanocomposites with enhanced impact strength

    Treesearch

    Yucheng Peng; Sergio A. Gallegos; Douglas J. Gardner; Yousoo Han; Zhiyong Cai

    2014-01-01

    The unique aspect of polymer composites reinforced by various fillers or additives is that the mechanical properties of the material can be tailored to fit a variety of uses: construction, transportation, industrial, and consumer applications. By selecting a specific reinforcement or designing a particular manufacturing process a material with desired properties can be...

  10. Polymer solutions

    DOEpatents

    Krawczyk, Gerhard Erich; Miller, Kevin Michael

    2011-07-26

    There is provided a method of making a polymer solution comprising polymerizing one or more monomer in a solvent, wherein said monomer comprises one or more ethylenically unsaturated monomer that is a multi-functional Michael donor, and wherein said solvent comprises 40% or more by weight, based on the weight of said solvent, one or more multi-functional Michael donor.

  11. Antimicrobial polymers.

    PubMed

    Jain, Anjali; Duvvuri, L Sailaja; Farah, Shady; Beyth, Nurit; Domb, Abraham J; Khan, Wahid

    2014-12-01

    Better health is basic requirement of human being, but the rapid growth of harmful pathogens and their serious health effects pose a significant challenge to modern science. Infections by pathogenic microorganisms are of great concern in many fields such as medical devices, drugs, hospital surfaces/furniture, dental restoration, surgery equipment, health care products, and hygienic applications (e.g., water purification systems, textiles, food packaging and storage, major or domestic appliances etc.) Antimicrobial polymers are the materials having the capability to kill/inhibit the growth of microbes on their surface or surrounding environment. Recently, they gained considerable interest for both academic research and industry and were found to be better than their small molecular counterparts in terms of enhanced efficacy, reduced toxicity, minimized environmental problems, resistance, and prolonged lifetime. Hence, efforts have focused on the development of antimicrobial polymers with all desired characters for optimum activity. In this Review, an overview of different antimicrobial polymers, their mechanism of action, factors affecting antimicrobial activity, and application in various fields are given. Recent advances and the current clinical status of these polymers are also discussed.

  12. Diclofenac sodium (DS) loaded bioerodible polymer based constructs

    NASA Astrophysics Data System (ADS)

    Piras, M.; Chiellini, F.; Nikkola, L.; Ashammakhi, N.; Chiellini, E.

    2008-02-01

    Pain is a prevalent problem that can raise morbidity of patients. Pain killer releasing biodegradable materials have been developed by using different techniques and biomaterials. The objective of the current study is to evaluate the use of a new bioerodible polymer for release of diclofenac sodium (DS). 1-butanol hemiester poly(maleic anhydride-alt-2-methoxyethyl vinyl ether) (PAM14) was prepared in the university of Pisa and selected as polymer of choice for the study. Polymer solutions of 5-10% (in ethanol or in acetic acid) were prepared, half of them containing 2% DS. The solutions were then electrospun to produce nanomats that were subsequently characterized using SEM. Fiber diameter was 160 nm 1 μm. Increasing polymer concentration increased the size of the fibers but reduced the number of beads (with or without DS). In the specimens obtained from acetic acid solution, the addition of DS resulted in a reduction in fiber diameter and an increase in the inter-bead distance. Corresponding ethanol solutions gave more homogeneous specimens than did acetic acid, having a lower number of beads. With the addition of DS a reduction in fiber diameter was observed for the acetic acid specimens. However, in ethanol, adding DS resulted in increased fiber diameter. Accordingly, it can be concluded that it is feasible to develop electrospun diclofenac releasing bioerodible nanostructures that have potential use in pain management. Their further evaluation is however, needed both in vitro and in vivo.

  13. Design of a multi-dopamine-modified polymer ligand optimally suited for interfacing magnetic nanoparticles with biological systems.

    PubMed

    Wang, Wentao; Ji, Xin; Na, Hyon Bin; Safi, Malak; Smith, Alexandra; Palui, Goutam; Perez, J Manuel; Mattoussi, Hedi

    2014-06-03

    We have designed a set of multifunctional and multicoordinating polymer ligands that are optimally suited for surface functionalizing iron oxide and potentially other magnetic nanoparticles (NPs) and promoting their integration into biological systems. The amphiphilic polymers are prepared by coupling (via nucleophilic addition) several amine-terminated dopamine anchoring groups, poly(ethylene glycol) moieties, and reactive groups onto a poly(isobutylene-alt-maleic anhydride) (PIMA) chain. This design greatly benefits from the highly efficient and reagent-free one-step reaction of maleic anhydride groups with amine-containing molecules. The availability of several dopamine groups in the same ligand greatly enhances the ligand affinity, via multiple coordination, to the magnetic NPs, while the hydrophilic and reactive groups promote colloidal stability in buffer media and allow subsequent conjugation with target biomolecules. Iron oxide nanoparticles ligand exchanged with these polymer ligands have a compact hydrodynamic size and exhibit enhanced long-term colloidal stability over the pH range of 4-12 and in the presence of excess electrolytes. Nanoparticles ligated with terminally reactive polymers have been easily coupled to target dyes and tested in live cell imaging with no measurable cytotoxicity. Finally, the resulting hydrophilic nanoparticles exhibit large and size-dependent r2 relaxivity values.

  14. Catalytic effect of gallium chloride in the diels-alder reaction between maleic anhydride and its derivatives and unsubstituted and substituted anthracenes

    SciTech Connect

    Kiselev, V.D.; Konovalov, A.I.; Shakirov, I.M.

    1985-11-10

    The stability of n, v complexes between gallium chloride and unsubstituted and substituted maleic anhydrides was determined in benzene by a thermochemical method; it was shown that the stability of the complexes decreases in the transition from maleic anhydrides with electron-donating substituents to maleic anhydrides with electron-withdrawing substituents. The reactivity of these dienophiles in the uncatalyzed Diels-Alder reactions with unsubstituted and substituted anthracenes in benzene and in the reactions catalyzed by gallium chloride was studied. The reactivity of the dienophiles varies similarly in the reactions with the investigated dienes, and this rules out treatment of steric hindrances as the reason for the reduced reactivity of the substituted dienophiles. A decrease in the catalytic effect was observed for the unreactive diene-dienophile pairs.

  15. Synthesis of comb-like copolymers from renewable resources: Itaconic anhydride, stearyl methacrylate and lactic acid

    NASA Astrophysics Data System (ADS)

    Shang, Shurui

    The synthesis and properties of comb-like copolymers and ionomers derived from renewable resources: itaconic anhydride (ITA), stearyl methacrylate (SM) and lactic acid (LA) are described. The copolymers based on ITA and SM (ITA-SM) were nearly random with a slight alternating tendency. The copolymers exhibited a nanophase-separated morphology, with the stearate side-chains forming a bilayer, semi-crystalline structure. The crystalline side-chains suppressed molecular motion of the main-chain, so that a glass transition temperature (Tg) was not resolved unless the ITA concentration was sufficiently high so that Tg > the melting point (Tm). The softening point and modulus of the copolymers increased with the increasing ITA concentration, but the thermal stability decreased. The ITA moiety along the main chain of the copolymers was neutralized with metal acetates to produce Na-, Ca- and Zn- random ionomers with comb-like architectures. In general, the incorporation of the ionic groups increased the Tg and suppressed the crystallinity of the side-chain packing. Ionomers with high SM side-chain density had two competing driving forces for self-assembled nano-phase separation: ionic aggregation and side-chain crystalline packing. Upon neutralization, a morphological transition from semi-crystalline lamella to spherical ionic aggregation was observed by small angle X-ray scattering (SAXS) analysis and transmission electron microscopy (TEM). Thermomechanical analysis revealed an increasing resistance to penetration deformation with an increasing degree of neutralization and an apparent rubbery plateau was observed above Tg. A controlled transesterification of PLA in glassware was an effective way to prepare a methacrylate functionalized PLA macromonomer with controlled molecular weight, which was used to synthesize a variety of copolymers. The copolymerization of this functionalized PLA macromonomer with ITA totally suppressed the side-chain crystallinity for the PLA chain

  16. Autoimmune response in MRL+/+ mice following treatment with dichloroacetyl chloride or dichloroacetic anhydride

    SciTech Connect

    Cai Ping; Koenig, Rolf; Khan, M. Firoze; Qiu, Suimin; Kaphalia, Bhupendra S.; Ansari, G.A.S. . E-mail: sansari@utmb.edu

    2006-10-15

    Dichloroacetyl chloride (DCAC) is formed from trichloroethene (TCE), which is implicated in inducing/accelerating autoimmune response. Due to its potent acylating activity, DCAC may convert proteins to neo-antigens and thus could induce autoimmune responses. Dichloroacetic anhydride (DCAA), which is a similar acylating agent, might also induce autoimmune responses. To evaluate if chloroacylation plays a role in the induction of autoimmunity, we have measured the autoimmune responses following treatment with DCAC or DCAA in autoimmune-prone MRL+/+ mice. Five-week-old female mice were injected intraperitoneally (twice weekly) with 0.2 mmol/kg of DCAC or DCAA in corn oil for 6 weeks. Total serum IgG, IgG1, and IgE levels were significantly increased in DCAC-treated mice as compared to controls. These increases corresponded with increases in DCAC-specific IgG and IgG1 levels. Total serum IgM was decreased in both DCAC- and DCAA-treated mice. Antinuclear antibodies, measured as an indication of systemic autoimmune responses, were increased in both DCAC- and DCAA-treated mice. Of eight Th1/Th2 cytokines measured in the serum, only IL-5 was significantly decreased in both treatment groups. The cytokine secretion patterns of splenic lymphocytes after stimulation with antibodies against CD3 (T cell receptor-mediated signal) and CD28 (costimulatory signal) differed between treatment and control groups. Levels of IL-1, IL-3, IL-6, IFN-{gamma}, G-CSF, and KC were higher in cultures of stimulated splenocytes from either DCAC- or DCAA-treated mice than from controls. The level of IL-17 was only increased in cultures from DCAC-treated mice. Increased lymphocytic populations were found in the red pulp of spleens following treatment with either DCAC or DCAA. In addition, thickening of the alveolar septa in the lungs of DCAC- or DCAA-treated mice was observed. The lung histopathology in exposed mice was consistent with the symptomology observed in welders exposed to DCAC

  17. Modelling of crystal structure of cis-1,2,3,6 and 3,4,5,6-tetrahydrophthalic anhydrides using lattice energy calculations.

    PubMed

    Fredj, A Ben; Day, G M

    2015-08-01

    Lattice energy calculations using a model potential were performed to model the crystal structures of cis-1,2,3,6- and 3,4,5,6-tetrahydrophthalic (THP) anhydrides. The optimized molecular models using the DFT method at the B3LYP/6-31G** level were found consistent with the available experimental evidence and allowed all differences observed in crystal packing between cis-1,2,3,6- and 3,4,5,6-THP anhydrides to be reproduced. Calculations provide evidence for the presence of dipole-dipole C=O⋯C=O intermolecular interactions and support the idea that the molecules distort from their ideal geometries, improving packing in both crystals. The search for minima in the lattice energy of both crystals amongst the more common space groups with Z' = 1, using a simulated annealing crystal structure prediction procedure followed by lattice energy minimization showed that the observed structure of 3,4,5,6-THP anhydride (Z' = 2) is the thermodynamically most stable, and allowed us to justify why 3,4,5,6-THP anhydride crystallizes in such a complex structure with 16 molecules in the unit cell. The computational model was successful in predicting the second observed form at 173 K for cis-1,2,3,6-THP anhydride as a polymorph, and could predict several hypothetical structures with Z' = 1 that appear competitive with the observed structures. The results of phonon estimates of zero point intermolecular vibrational energy and entropy suggest that crystal structures of cis-1,2,3,6-THP anhydride cannot be predicted solely on the basis of lattice energy; factors other than thermodynamics favor the observed structures.

  18. Increased oral bioavailability of paclitaxel by its encapsulation through complex formation with cyclodextrins in poly(anhydride) nanoparticles.

    PubMed

    Agüeros, M; Zabaleta, V; Espuelas, S; Campanero, M A; Irache, J M

    2010-07-01

    The aim of this work was to study the oral bioavailability in rats of paclitaxel (PTX) when encapsulated as a complex with cyclodextrins in poly(anhydride) nanoparticles (NP). For this purpose three different cyclodextrins were selected: beta-cyclodextrin (CD), 2-hydroxypropyl-beta-cyclodextrin (HPCD) and 6-monodeoxy-6-monoamino-beta-cyclodextrin (NHCD). A single dose of 10mg paclitaxel per kg body weight as PTX-cyclodextrin nanoparticles was used. Plasma curves were characterised by a plateau of paclitaxel concentration close to the C(max) from T(max) till 24h post-administration. For PTX-CD NP and PTX-HPCD NP, these sustained levels of the anticancer drug were found to be between 27 and 33-fold higher than the reported value of drug activity whereas the relative oral bioavailability of paclitaxel was calculated to be higher than 80%. These facts would be directly related with a synergistic effect obtained by the combination of the bioadhesive properties of poly(anhydride) nanoparticles and the inhibitory effect of cyclodextrins on the activity of P-glycoprotein and cythocrome P450.

  19. Safer one-pot synthesis of the ‘SHAPE’ reagent 1-methyl-7-nitroisatoic anhydride (1m7)

    PubMed Central

    Turner, Rushia; Shefer, Kinneret; Ares, Manuel

    2013-01-01

    Estimating the reactivity of 2′-hydroxyl groups along an RNA chain of interest aids in the modeling of the folded RNA structure; flexible loops tend to be reactive, whereas duplex regions are generally not. Among the most useful reagents for probing 2′-hydroxyl reactivity is 1-methyl-7-nitroisatoic anhydride (1m7), but the absence of a reliable, inexpensive source has prevented widespread adoption. An existing protocol for the conversion of an inexpensive precursor 4-nitroisatoic anhydride (4NIA) recommends the use of NaH in dimethylformamide (DMF), a reagent combination that most molecular biology labs are not equipped to handle, and that does not scale safely in any case. Here we describe a safer, one-pot method for bulk conversion of 4NIA to 1m7 that reduces costs and bypasses the use of NaH. We show that 1m7 produced by this method is free of side products and can be used to probe RNA structure in vitro. PMID:24141619

  20. Derivatization procedures and determination of levoglucosan and related monosaccharide anhydrides in atmospheric aerosols by gas chromatography-mass spectrometry.

    PubMed

    Hsu, Ching-Lin; Cheng, Chin-Yuan; Lee, Chung-Te; Ding, Wang-Hsien

    2007-04-15

    This study evaluated the derivatization procedures for detecting the three most commonly monosaccharide anhydrides (MAs) (levoglucosan, mannosan and galactosan) in atmospheric aerosols using gas chromatography-mass spectrometry (GC-MS). Various silylating agents, mainly trimethylsilylating agents (TMS), were compared and the effects of various contents of trimethylchlorosilane (TMCS, as a stimulator) were evaluated to optimize the conditions for detecting these compounds in aerosol samples. Differences among the abundances of the derivatives were caused by the sterical hindrance of three hydroxyl groups in the structures of monosaccharide anhydrides. The effects of the reaction time and temperature were also examined. The optimal reaction time and temperature were 60min and 80 degrees C with 1% TMCS plus 0.2% 1,4-dithioerythritol (DTE). Under these conditions, the percentages of formation of bis-O-TMS derivatives (as by-products) were 23, 29 and 10% for galactosan, mannosan and levoglucosan, respectively. The concentrations of galactosan, mannosan and levoglucosan in particles of smoke samples ranged from 29 to 88, 23 to 69 and 77 to 380ng/m(3), respectively; and in particles of atmospheric aerosols ranged from 0.06 to 0.75, n.d. to 0.49 and 1.6 to 132ng/m(3), respectively. Levoglucosan was the dominant MAs detected in both type of samples. Less than 10% quantitation difference was obtained when bis-O-TMS derivatives were included in the calculation.

  1. Adsorptive removal of copper (II) and lead (II) using chitosan-g-maleic anhydride-g-methacrylic acid copolymer.

    PubMed

    Lavanya, R; Gomathi, T; Vijayalakshmi, K; Saranya, M; Sudha, P N; Anil, Sukumaran

    2017-11-01

    In the present work, the maleic anhydride and methacrylic acid monomers were grafted one after another onto chitosan by using ceric ammonium nitrate as the initiator. The optimum conditions for grafting were studied by varying the initiator concentration, monomer concentration and reaction temperature. The synthesized grafted samples were subjected to various analytical techniques such as FTIR, XRD, TGA and DSC methods The proof of formation of graft copolymer was ascertained from the results of FTIR analysis and XRD studies. The TGA and DSC results conclude the highly thermally stable behavior of the prepared graft copolymer sample. The prepared graft copolymer was utilized for removing copper and lead from aqueous solutions and optimum adsorption parameters were evaluated under various pH, adsorbent dose, contact time and initial metal ion concentration. The adsorption and kinetic studies have been explained by Langmuir, Freundlich and pseudo - first order, second order and intra particle diffusion models. From the results, it was seen that Freundlich isotherm was best fit in the case of adsorption studies which followed pseudo second order kinetics. The obtained results showed that the chitosan-g-maleic anhydride-g-methacrylic acid copolymer was very efficient in removing the heavy metals copper and lead from aqueous solution. Copyright © 2017 Elsevier B.V. All rights reserved.

  2. Anhydride functionalised calcium ferrite nanoparticles: a new selective magnetic material for enrichment of lead ions from water and food samples.

    PubMed

    Pirouz, Mojgan Jafari; Beyki, Mostafa Hossein; Shemirani, Farzaneh

    2015-03-01

    In this research a sonochemistry route for manufacture of uniform nanocrystalline CaFe2O4 and its anhydride functionalisation were reported. The potential of raw and modified material as a magnetically separable sorbent in selective enrichment of lead ions from water and food samples is outlined. This material was characterised using FT-IR, XRD, SEM and VSM techniques. The SEM and VSM results indicated that the calcium ferrite nanoparticles are sphere-like particles possessing superparamagnetic properties with an average diameter of 40 nm. Various analytical parameters, including pH, contact time, type and concentration of eluent, adsorption capacity, sample volume and interference of ions, were optimised. Following a modification by anhydride, calcium ferrite selectivity toward lead ions was raised more than twofold compared to the unmodified nanoparticles. Finally a pre-concentration procedure was applied for determination of trace Pb(II) in canned tuna fish, canned tomato paste, parsley, milk and well-water samples with satisfactory results.

  3. Advanced Polymer

    NASA Technical Reports Server (NTRS)

    1992-01-01

    In the mid-1980's, Langley developed a polyimide sulfone, combining desirable properties of two classes of polymers. Composites and other products made from polyimide sulfone can be used with solvents and corrosive fluids, are light weight, low cost and can be easily fabricated for a wide range of industrial uses. High Technology Systems, Inc. obtained a license for the polymer and was awarded a Small Business Innovation Research (SBIR) contract for development in a powder form. Although its principal use is as a matrix resin for composites, the material can also be used as a high temperature structural adhesive for aircraft structures and as a coating for protection from heat and radiation for electronic components.

  4. Phthalocyanine polymers

    NASA Technical Reports Server (NTRS)

    Achar, B. N.; Fohlen, G. M.; Parker, J. A. (Inventor)

    1985-01-01

    A method of forming 4,4',4'',4''' -tetraamino phthalocyanines involves reducing 4,4',4'',4''' -tetranitro phthalocyanines, polymerizing the metal tetraamino phthalocyanines with a tetracarboxylic dianhydride (preferably aromatic) or copolymerizing with a tetracarboxylic dianhydride and a diamine (preferably also aromatic) to produce amic acids which are then dehydrocyclized to imides. Thermally and oxidatively stable polymers result which form tough, flexible films, varnishes, adhesives, and fibers.

  5. Theoretical Polymers.

    DTIC Science & Technology

    1976-10-07

    for the correlation length of 3/4, while 0.72 is observed. Then followed several talks on the expansion coefficient a, the virial coefficients and...calculation of the virial coefficient and c~2. These quantities can be considered merely a testing ground for the use of this method to polymer...the second viria]. coefficient , A2, to be zero and the intrinsic viscosity dependent on~VW for polystyrene mole-cular weights between 33,000 and one

  6. Polymer blends

    DOEpatents

    Allen, Scott D.; Naik, Sanjeev

    2017-08-22

    The present invention provides, among other things, extruded blends of aliphatic polycarbonates and polyolefins. In one aspect, provided blends comprise aliphatic polycarbonates such as poly(propylene carbonate) and a lesser amount of a crystalline or semicrystalline polymer. In certain embodiments, provided blends are characterized in that they exhibit unexpected improvements in their elongation properties. In another aspect, the invention provides methods of making such materials and applications of the materials in applications such as the manufacture of consumer packaging materials.

  7. Gratings in nonlinear optical polymers for integrated optical device applications

    NASA Astrophysics Data System (ADS)

    Kardinahl, Thiemo; Franke, Hilmar

    1993-12-01

    The polymer poly(methyl methacrylate) (PMMA) doped with the active photoinitiator dimethoxyphenalacetophenon (DMPA) is a well known material to form permanent gratings by uv-holographie. An additional doping with the photochromic material E-(alpha) (2,5- dimethyl-3-furyl)ethylidene(adamantylidene)succinic anhydride (Aberchrome 670) leads to a one step fabrication of a nonlinear optical grating. After the permanent grating is fixed, the refractive index of the grating can be tuned by a homogenous illumination. The diffraction efficiency of the grating can be tuned because the fulgide Aberchrome 670 undergoes a reversible transition from its bleached to its colored form by homogeneous uv illumination and back again by irradiating the film with a wavelength near the absorption maximum (here (lambda) equals 514.5 nm).

  8. Plasma deposition of polymer composite films incorporating nanocellulose whiskers

    NASA Astrophysics Data System (ADS)

    Samyn, P.; Airoudj, A.; Laborie, M.-P.; Mathew, A. P.; Roucoules, V.

    2011-11-01

    In a trend for sustainable engineering and functionalization of surfaces, we explore the possibilities of gas phase processes to deposit nanocomposite films. From an analysis of pulsed plasma polymerization of maleic anhydride in the presence of nanocellulose whiskers, it seems that thin nanocomposite films can be deposited with various patterns. By specifically modifying plasma parameters such as total power, duty cycle, and monomer gas pressure, the nanocellulose whiskers are either incorporated into a buckled polymer film or single nanocellulose whiskers are deposited on top of a polymeric film. The density of the latter can be controlled by modifying the exact positioning of the substrate in the reactor. The resulting morphologies are evaluated by optical microscopy, AFM, contact angle measurements and ellipsometry.

  9. Periodic Polymers

    NASA Astrophysics Data System (ADS)

    Thomas, Edwin

    2013-03-01

    Periodic polymers can be made by self assembly, directed self assembly and by photolithography. Such materials provide a versatile platform for 1, 2 and 3D periodic nano-micro scale composites with either dielectric or impedance contrast or both, and these can serve for example, as photonic and or phononic crystals for electromagnetic and elastic waves as well as mechanical frames/trusses. Compared to electromagnetic waves, elastic waves are both less complex (longitudinal modes in fluids) and more complex (longitudinal, transverse in-plane and transverse out-of-plane modes in solids). Engineering of the dispersion relation between wave frequency w and wave vector, k enables the opening of band gaps in the density of modes and detailed shaping of w(k). Band gaps can be opened by Bragg scattering, anti-crossing of bands and discrete shape resonances. Current interest is in our group focuses using design - modeling, fabrication and measurement of polymer-based periodic materials for applications as tunable optics and control of phonon flow. Several examples will be described including the design of structures for multispectral band gaps for elastic waves to alter the phonon density of states, the creation of block polymer and bicontinuous metal-carbon nanoframes for structures that are robust against ballistic projectiles and quasi-crystalline solid/fluid structures that can steer shock waves.

  10. In situ compatibilizer-reinforced interface between a flexible polymer (a functionalized polypropylene) and a rodlike polymer (a thermotropic liquid crystalline polymer).

    PubMed

    Seo, Yongsok; Ninh, Tran Hai; Hong, Soon Man; Kim, Sehyun; Kang, Tae Jin; Kim, Hansung; Kim, Jinyeol

    2006-03-28

    We present an investigation of the interfacial reinforcement between a flexible folded-chain polymer (functionalized polypropylene-maleic anhydride-grafted polypropylene, MAPP) and a rodlike polymer (a themotropic liquid crystalline polymer, TCLP - poly(ester amide)). Fracture toughness was measured using an asymmetric double-cantilever beam test (ADCB). High fracture toughness at the bonding temperature of 200 degrees C indicates that a chemical reaction has occurred at the interface to provide a strong interaction between MAPP and TLCP. Despite the higher modulus of TLCP, the fracture was propagated in the TLCP phase because of inherent TLCP domain structure. An analysis on the locus of failure revealed that at constant bonding temperature the fracture toughness between MAPP and TLCP was influenced not only by the bonding temperature but also by the bonding time. The fracture toughness increased with the bonding temperature until 200 degrees C was reached and then decreased at higher bonding temperature. The fracture toughness increased with annealing time until it reached a plateau value. We ascribe the dependence of the fracture toughness on the bonding time to the progressive occurrence of two different failure mechanisms, adhesive failure and cohesive failure. The adhesive strength increased with bonding temperature whereas the cohesive strength decreased because of weaker adhesion between TLCP crystalline domains. The dependence of fracture toughness on bonding time was explained in terms of the TLCP crystalline domain structure.

  11. Hyperbranched polymer films and dendrimers: Their chemistry and applications

    NASA Astrophysics Data System (ADS)

    Zhao, Mingqi

    The research in this dissertation examines the chemistry and applications of dendritic polymers; specifically, hyperbranched polymer thin films and dendrimers. We examined hyperbranched, fluorinated and unfluorinated poly(acrylic acid) (PAA) films on gold substrates, poly(amidoamine) (PAMAM) dendrimer monolayers and dendrimer-alkanethiol mixed monolayers on gold substrates, PAMAM dendrimer/poly(anhydride) and poly(iminopropane-1,3-diyl) (Cascade) dendrimer/poly(anhydride) multilayer films on silicon, gold, and aluminum substrates, PAMAM dendrimer/metal-ion composites, and PAMAM dendrimer-encapsulated metal nanoclusters in solution and on electrode surfaces. Hyperbranched PAA films have pH-dependent blocking abilities: at low pH PAA films effectively passivate Au electrodes while at high pH they are open and permeable. Fluorinated PAA films are far less permeable at any pH. Dendrimers ranging from generation 4 to 8 (G4--G8) can form highly stable and nearly close-packed monolayers and mixed monolayers with hexadecanethiol (C16SH) on surfaces. Moreover, dendrimers embedded within C16SH can act as gates of molecular dimension that control intradendrimer mass transfer of ions. Dendrimer/poly(anhydride) multilayers on surfaces were synthesized and their permeability was investigated. These composite membranes exhibit fully reversible, pH-switchable permselectivity for both cationic and anionic probe molecules because of their pH-dependent electrostatic properties. After heating, such films become highly blocking over the pH range studied due to thermally induced interdendrimer imidization, and other reactions. Finally, we show that PAMAM dendrimers can act first as templates for the preparation of transition-metal nanoclusters, and subsequently as stabilizers. Dendrimers quantitatively complex many transition-metal ions, including Cu 2+, Pt2+, Pd2+, Ru3+, and Ni2+, within their interiors. Chemical reduction of such nanocomposites results in formation of dendrimer

  12. Jeffamine® based polymers as highly conductive polymer electrolytes and cathode binder materials for battery application

    NASA Astrophysics Data System (ADS)

    Aldalur, Itziar; Zhang, Heng; Piszcz, Michał; Oteo, Uxue; Rodriguez-Martinez, Lide M.; Shanmukaraj, Devaraj; Rojo, Teofilo; Armand, Michel

    2017-04-01

    We report a simple synthesis route towards a new type of comb polymer material based on polyether amines oligomer side chains (i.e., Jeffamine® compounds) and a poly(ethylene-alt-maleic anhydride) backbone. Reaction proceeds by imide ring formation through the NH2 group allowing for attachment of side chains. By taking advantage of the high configurational freedoms and flexibility of propylene oxide/ethylene oxide units (PO/EO) in Jeffamine® compounds, novel polymer matrices were obtained with good elastomeric properties. Fully amorphous solid polymer electrolytes (SPEs) based on lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) and Jeffamine®-based polymer matrices show low glass transition temperatures around -40 °C, high ionic conductivities and good electrochemical stabilities. The ionic conductivities of Jeffamine-based SPEs (5.3 × 10-4 S cm-1 at 70 °C and 4.5 × 10-5 S cm-1 at room temperature) are higher than those of the conventional SPEs comprising of LiTFSI and linear poly(ethylene oxide) (PEO), due to the amorphous nature and the high concentration of mobile end-groups of the Jeffamine-based polymer matrices rather than the semi-crystalline PEO The feasibility of Jeffamine-based compounds in lithium metal batteries is further demonstrated by the implementation of Jeffamine®-based polymer as a binder for cathode materials, and the stable cycling of Li|SPE|LiFePO4 and Li|SPE|S cells using Jeffamine-based SPEs.

  13. Efficacy of measures of hygiene in workers sensitised to acid anhydrides and the influence of selection bias on the results

    PubMed Central

    Drexler, H.; Schaller, K. H.; Nielsen, J.; Weber, A.; Weihrauch, M.; Welinder, H.; Skerfving, S.

    1999-01-01

    OBJECTIVES: Organic acid anhydrides are potential sensitisers and cause occupational airway diseases. In an intervention study the efficacy of measures of hygiene at the workplace and possible selection bias were investigated. METHODS: A first investigation with 110 workers exposed to hexahydrophthalic acid anhydride (HHPA) and methyltetrahydrophthalic acid anhydride (MTHPA) was carried out in July 1991. The results (skin prick test, specific serum IgE) showed that 20 people were sensitised, and in a challenge test the clinical relevance of the sensitisation was confirmed in six subjects. In December 1991, the hygiene conditions at the plant were improved. In November 1995 a second investigation of 84 people was performed (anamnesis, skin prick test, specific IgE, spirometry, and ambient and biological monitoring). The 27 people who had left the plant in the meantime were asked their reasons for leaving. RESULTS: The relative risk of people sensitised in 1991 of leaving the plant between 1991 and 1995 was 2.6 (95% confidence interval (95% CI) 1.4 to 4.9) compared with people without any sign of sensitisation. The percentage of people identified as sensitised in 1991, who were still working at the plant and came to the second investigation, was higher than for people without evidence of sensitisation (10/10 v 47/73; p < 0.05). In all the 10 sensitised people in 1991 the findings of the first investigation were confirmed in 1995. The rate of sensitisation in 1995 was 21%. None of the six people employed after 1991 showed evidence of sensitisation. Of the six people with clinically relevant sensitisation confirmed by a challenge test in 1991, five were still at their workplace. From 1991 they were only exposed to MTHPA at a reduced concentration (< 0.5-36 micrograms/m3 in 1995). All of them reported fewer symptoms than in 1991. No signs of bronchial obstruction were detected by spirometry at the workplace. CONCLUSIONS: In cross sectional studies there is a selection

  14. SELECTIVE HYDROGENATION OF MALEIC ANHYDRIDE TO Y-BUTROLACTONE OVER PD/AL2O3 CATALYST USING SUPERCRITICAL CARBON DIOXIDE MEDIUM

    EPA Science Inventory

    Hydrogenation of maleic anhydride to g-butyrolactone over Pd/Al2O3 catalyst under supercritical carbondioxide medium

    Unnikrishnan R. Pillai and Endalkachew Sahle-Demessie
    National Risk Management Research laboratory (NRMRL), Clean Processes Branch, MS 443, United States...

  15. 40 CFR 721.3635 - Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4). 721.3635 Section 721.3635 Protection of... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.3635 Octadecanoic acid...

  16. 40 CFR 721.3635 - Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4). 721.3635 Section 721.3635 Protection of... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.3635 Octadecanoic acid...

  17. 40 CFR 721.3635 - Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Octadecanoic acid, ester with 1,2-propanediol, phosphate, anhydride with silicic acid (H4SiO4). 721.3635 Section 721.3635 Protection of... CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.3635 Octadecanoic acid...

  18. An atom-economic approach to carboxylic acids via Pd-catalyzed direct addition of formic acid to olefins with acetic anhydride as a co-catalyst.

    PubMed

    Wang, Yang; Ren, Wenlong; Shi, Yian

    2015-08-21

    An effective Pd-catalyzed hydrocarboxylation of olefins using formic acid with acetic anhydride as a co-catalyst is described. A variety of carboxylic acids are obtained in good yields with high regioselectivities under mild reaction conditions without the use of toxic CO gas.

  19. Is the 2,3-carbon-carbon bond of indole really inert to oxidative cleavage by Oxone?--synthesis of isatoic anhydrides from indoles.

    PubMed

    Nelson, Amber C; Kalinowski, Emily S; Czerniecki, Nikolas J; Jacobson, Taylor L; Grundt, Peter

    2013-11-21

    A recent report has indicated that the oxidizing agent Oxone does not possess the ability to cleave the 2,3-carbon-carbon bond of indole. Work in our laboratory shows that this is not the case. Indole and a variety of aryl ring substituted derivatives readily react to form synthetically important isatoic anhydrides.

  20. Biotin-conjugated N-methylisatoic anhydride: a chemical tool for nucleic acid separation by selective 2'-hydroxyl acylation of RNA.

    PubMed

    Ursuegui, S; Chivot, N; Moutin, S; Burr, A; Fossey, C; Cailly, T; Laayoun, A; Fabis, F; Laurent, A

    2014-06-01

    An isatoic anhydride derivative conjugated to a biotin and a disulfide linker was specifically designed for the separation of nucleic acids. Starting from a DNA-RNA mixture, a selective 2'-hydroxyl acylation of RNAs followed by capture with streptavidin-coated magnetic beads and cleavage of the disulfide led to elution of RNAs.

  1. Characterization of maleic acid/anhydride copolymer films by low-rate dynamic liquid-fluid contact angle measurements using axisymmetric drop shape analysis.

    PubMed

    Uhlmann, Petra; Skorupa, Sebastian; Werner, Carsten; Grundke, Karina

    2005-07-05

    Thin films of alternating maleic acid/anhydride copolymers (poly(octadecene-alt-maleic acid/anhydride), POMA; poly(propene-alt-maleic acid/anhydride), PPMA; poly(styrene-alt-maleic acid/anhydride), PSMA) were studied to unravel the influence of the comonomer characteristics in the backbone on the surface-energetic properties of the copolymer films in the dry state and in contact with aqueous solutions. Water contact angle measurements revealed a graduation of the wettability of the dry hydrolyzed and annealed copolymer films that was dependent on the comonomer unit. It ranged from moderately hydrophilic (PPMA, annealed gamma(sv) = 39.9 mJ/m2) to very hydrophobic (POMA, annealed, gamma(sv) = 18.4 mJ/m2) surfaces. Liquid-fluid contact angle measurements using captive air bubbles were performed in different aqueous media (pure water, phosphate-buffered saline, and 10(-)(3) M KCl of two different pH values (pH = 3 and pH = 10) to study the copolymer films in their hydrated states relevant for biointerfacial phenomena. It was found that the graduation of the wettability of the copolymer films in the dry state is overall maintained upon immersion in aqueous solutions. The dependence of the wettability on the pH value of the aqueous medium could be related to the (de)protonation of the carboxylic groups.

  2. Asymmetric synthesis of the HMG-CoA reductase inhibitor atorvastatin calcium: an organocatalytic anhydride desymmetrization and cyanide-free side chain elongation approach.

    PubMed

    Chen, Xiaofei; Xiong, Fangjun; Chen, Wenxue; He, Qiuqin; Chen, Fener

    2014-03-21

    An efficient asymmetric synthesis of atorvastatin calcium has been achieved from commercially available diethyl 3-hydroxyglutarate through a novel approach that involves an organocatalytic enantioselective cyclic anhydride desymmetrization to establish C(3) stereogenicity and cyanide-free assembly of C7 amino type side chain via C5+C2 strategy as the key transformations.

  3. SELECTIVE HYDROGENATION OF MALEIC ANHYDRIDE TO Y-BUTROLACTONE OVER PD/AL2O3 CATALYST USING SUPERCRITICAL CARBON DIOXIDE MEDIUM

    EPA Science Inventory

    Hydrogenation of maleic anhydride to g-butyrolactone over Pd/Al2O3 catalyst under supercritical carbondioxide medium

    Unnikrishnan R. Pillai and Endalkachew Sahle-Demessie
    National Risk Management Research laboratory (NRMRL), Clean Processes Branch, MS 443, United States...

  4. Morphology and phase controlled cobalt nanostructures in magnetic polypropylene nanocomposites: the role of alkyl chain-length in maleic anhydride grafted polypropylene.

    PubMed

    He, Qingliang; Yuan, Tingting; Luo, Zhiping; Haldolaarachchige, Neel; Young, David P; Wei, Suying; Guo, Zhanhu

    2013-04-04

    A novel function of maleic anhydride grafted polypropylene (PP) with different backbone chain-lengths was demonstrated, i.e., in controlling the cobalt morphologies (dispersed polyhedral vs. assembled chain nanostructure), crystalline structures (ε- vs. β-phase), and magnetic property (242 vs. 808 Oe) in the synthesized magnetic PP nanocomposites.

  5. Synthesis of both enantiomers of hemiesters by enantioselective methanolysis of meso cyclic anhydrides catalyzed by alpha-amino acid-derived chiral thioureas.

    PubMed

    Manzano, Rubén; Andrés, José M; Muruzábal, María-Dolores; Pedrosa, Rafael

    2010-08-06

    Both ureas and thioureas derived from L- or D-valine act as bifunctional organocatalysts able to induce the enantioselective alcoholysis of mono-, bi-, and tricyclic meso anhydrides. The desymmetrization occurs in near quantitative yields and excellent enantiomeric ratios (up to >99:<1) under low catalyst loading. Both enantiomers of the hemiesters can be directly obtained by changing the configuration of the catalyst.

  6. Reaction of dimethoxycarbene-DMAD zwitterion with 1,2-diones and anhydrides: a novel synthesis of highly substituted dihydrofurans and spirodihydrofurans.

    PubMed

    Nair, Vijay; Deepthi, Ani; Poonoth, Manojkumar; Santhamma, Bindu; Vellalath, Sreekumar; Babu, Beneesh Pattoorpady; Mohan, Resmi; Suresh, Eringathodi

    2006-03-17

    The zwitterion formed by the reaction of dimethoxycarbene and DMAD adds efficiently to one of the carbonyl groups of 1,2-dicarbonyl compounds and anhydrides to generate dihydrofurans and spirodihydrofurans in good yields. In many cases, the carbene inserts into the C-C bond of the dione to yield masked vicinal tricarbonyl systems.

  7. Chiral Polymers.

    DTIC Science & Technology

    1984-10-01

    TITLE (mid Subttlo) 񓂬-JS. TYPE OF REPORT & PERIOD COVERED CHIRAL POLYMERS /~O~~ R E~NNE 7. AUTHOR(e) 11. CONTRACT OR GRANT NUNSIER(e) J. K. Stille...acrylamide monomer containing a chiral 1,3-dioxane unit as well as both racemic and ( R )-6.-methyl ene-vi-methyl -7-butyrol actone were synthesi zed...or ( R )-propylene oxide (10)6. The key step in this synthesis is the palladium catalyzed carbonylation of 4-bromopent-4-en-2-ol. Thus, either racemic or

  8. Ionic Liquids as the MOFs/Polymer Interfacial Binder for Efficient Membrane Separation.

    PubMed

    Lin, Rijia; Ge, Lei; Diao, Hui; Rudolph, Victor; Zhu, Zhonghua

    2016-11-23

    Obtaining strong interfacial affinity between filler and polymer is critical to the preparation of mixed matrix membranes (MMMs) with high separation efficiency. However, it is still a challenge for micron-sized metal organic frameworks (MOFs) to achieve excellent compatibility and defect-free interface with polymer matrix. Thin layer of ionic liquid (IL) was immobilized on micron-sized HKUST-1 to eliminate the interfacial nonselective voids in MMMs with minimized free ionic liquid (IL) in polymer matrix, and then the obtained IL decorated HKUST-1 was incorporated into 4,4'-(hexafluoroisopropylidene)diphthalic anhydride-2,3,5,6-tetramethyl-1,3-phenyldiamine (6FDA-Durene) to fabricate MMMs. Acting as a filler/polymer interfacial binder, the favorable MOF/IL and IL/polymer interaction can facilitate the enhancement of MOF/polymer affinity. Compared to MMM with only HKUST-1 incorporation, MMM with IL decorated HKUST-1 succeeded in restricting the formation of nonselective interfacial voids, leading to an increment in CO2 selectivity. The IL decoration method can be an effective approach to eliminate interfacial voids in MMMs, extending the filler selection to a wide range of large-sized fillers.

  9. Lymphatic trafficking kinetics and near-infrared imaging using star polymer architectures with controlled anionic character

    PubMed Central

    Bagby, Taryn R.; Cai, Shuang; Duan, Shaofeng; Yang, Qiuhong; Thati, Sharadvi; Berkland, Cory; Aires, Daniel J.; Forrest, M. Laird

    2015-01-01

    Targeted lymphatic delivery of nanoparticles for drug delivery and imaging is primarily dependent on size and charge. Prior studies have observed increased lymphatic uptake and retentions of over 48 hrs for negatively charged particles compared to neutral and positively charged particles. We have developed new polymeric materials that extend retention over a more pharmaceutically relevant 7-day period. We used whole body fluorescence imaging to observe in mice the lymphatic trafficking of a series of anionic star poly-(6-O-methacryloyl-D-galactose) polymer-NIR dye (IR820) conjugates. The anionic charge of polymers was increased by modifying galactose moieties in the star polymers with succinic anhydride. Increasing anionic nature was associated with enhanced lymphatic uptake up to a zeta potential of ca. -40 mV; further negative charge did not affect lymphatic uptake. Compared to the 20% acid-conjugate, the 40 to 90% acid-star-polymer conjugates exhibited a 2.5- to 3.5-fold increase in lymphatic uptake in both the popliteal and iliac nodes. The polymer conjugates exhibited node half-lives of 2 to 20 hrs in the popliteal nodes and 19 to 114 hrs in the deeper iliac nodes. These polymer conjugates can deliver drugs or imaging agents with rapid lymphatic uptake and prolonged deep-nodal retention; thus they may provide a useful vehicle for sustained intralymphatic drug delivery with low toxicity. PMID:22546180

  10. Development of repaglinide microspheres using novel acetylated starches of bitter and Chinese yams as polymers.

    PubMed

    Okunlola, Adenike; Adebayo, Amusa Sarafadeen; Adeyeye, Moji Christianah

    2017-01-01

    Tropical starches from Dioscorea dumetorum (bitter) and Dioscorea oppositifolia (Chinese) yams were acetylated with acetic anhydride in pyridine medium and utilized as polymers for the delivery of repaglinide in microsphere formulations in comparison to ethyl cellulose. Acetylated starches of bitter and Chinese yams with degrees of substitution of 2.56 and 2.70 respectively were obtained. Acetylation was confirmed by FTIR, (1)H NMR spectroscopy. A 3(2) factorial experimental design was performed using polymer type and drug-polymer ratio as independent variables. Particle size, swelling, entrapment and time for 50% drug release (t50) were dependent variables. Contour plots showed the relationship between the independent factors and the response variables. All variables except swelling increased with drug: polymer ratio. Entrapment efficiency was generally in the rank of Bitter yam>Ethyl cellulose>Chinese yam. Repaglinide microspheres had size 50±4.00 to 350±18.10μm, entrapment efficiency 75.30±3.03 to 93.10±2.75% and t50 3.20±0.42 to 7.20±0.55h. Bitter yam starch gave longer dissolution times than Chinese yam starch at all drug-polymer ratios. Drug release fitted Korsmeyer-Peppas and Hopfenberg models. Acetylated bitter and Chinese yam starches were found suitable as polymers to prolong release of repaglinide in microsphere formulations.

  11. Ultrathin, flexible, and transparent polymer multilayer composites for the protection of silver surfaces.

    PubMed

    Langecker, Jens; Ritter, Helene; Fichini, Audrey; Rupper, Patrick; Faller, Markus; Hanselmann, Barbara

    2012-02-01

    Silver coatings at the nanoscale became of high interest for the integration of electronic functionalities on all kinds of objects for daily use. In these thin coatings, corrosion is a big problem as it destroys these thin layers and leads to a loss of conductivity due to missing bulk material. For protection of thin silver coatings against H(2)S induced corrosion, we developed nanocoatings based on the covalent layer-by-layer technique. We prepared composites by subsequent deposition of polyamines like polyethylenimine (PEI) or polyallylamine (PAAm) and polyanhydrides like poly(maleic anhydride-alt-methyl vinyl ether) (Gantrez) or poly(styrene-co-maleic anhydride) (PSMA). For the tuning of the hydrophobicity, the layers were terminated by reaction with palmitoylic acid derivatives. Reflectivity measurements, contact angle measurements, and AFM measurements were made to investigate how the coatings affect the surface properties. All coatings show a lower reflectivity below 450 nm compared to pure silver, depending on the number of layers deposited. The addition of a palmitoylic derivative to the surface increases the hydrophobicity, but only in case of the Gantrez-PVAm-composite, this approach leads to real hydrophobicity, reaching contact angles above 90°. AFM measurements show a decrease of the roughness of the polymer coated surfaces compared to the pure metal surfaces. Corrosion tests in a H(2)S atmosphere show a good protective effect of the palmitoyl-terminated composites. Martindale abrasion tests on coated textiles reveal a good stability of the prepared polymer composites.

  12. Effect of succinic anhydride as an electrolyte additive on electrochemical characteristics of silicon thin-film electrode

    NASA Astrophysics Data System (ADS)

    Han, Gi-Beom; Ryou, Myung-Hyun; Cho, Kuk Young; Lee, Yong Min; Park, Jung-Ki

    The effect of an electrolyte additive, succinic anhydride (SA), on the electrochemical performances of a silicon thin-film electrode, which is prepared by radio-frequency magnetron sputtering, is investigated. The introduction of SA into a liquid electrolyte consisting of ethylene carbonate/diethyl carbonate/1 M LiPF 6 significantly enhances the capacity retention and coulombic efficiency of the electrode. This improvement in the electrochemical performance of the electrode is attributed to modification of the solid/electrolyte interphase (SEI) layer by the introduction of SA. The differences in the characteristic properties of SEI layers, with or without SA, are explained by analysis with scanning electron microscopy, electrochemical impedance spectroscopy, and X-ray photoelectron spectroscopy.

  13. Facile Formation of Acetic Sulfuric Anhydride in a Supersonic Jet: Characterization by Microwave Spectroscopy and Computational Chemistry

    NASA Astrophysics Data System (ADS)

    Huff, Anna; Smith, CJ; Mackenzie, Becca; Leopold, Ken

    2017-06-01

    Sulfur trioxide and acetic acid are shown to react under supersonic jet conditions to form acetic sulfuric anhydride, CH_{3}COOSO_{2}OH. Rotational spectra of the parent, ^{34}S, methyl ^{13}C, and fully deuterated isotopologues have been observed by chirped-pulse and conventional cavity microwave spectroscopy. A and E internal rotation states have been observed for each isotopologue studied and the methyl group internal rotation barriers have been determined (241.043(65) \\wn for the parent species). The reaction is analogous to that of our previous report on the reaction of sulfur trioxide and formic acid. DFT and CCSD calculations are also presented which indicate that the reaction proceeds via a π_{2} + π_{2} + σ_{2} cycloaddition reaction. These results support our previous conjecture that the reaction of SO_{3} with carboxylic acids is both facile and general. Possible implications for atmospheric aerosol formation are discussed.

  14. Recovery of uranium(VI) from aqueous solution by 2-picolylamine functionalized poly(styrene-co-maleic anhydride) resin.

    PubMed

    Liu, Shudi; Yang, Ying; Liu, Tonghuan; Wu, Wangsuo

    2017-07-01

    A 2-picolylamine functionalized poly(styrene-co-maleic anhydride) resin was synthesized and characterized by FT-IR, elemental analysis, SEM and XPS. To recover uranium from aqueous solution, the influence factors such as pH values, contact time, temperature and initial uranium concentration were optimized. Adsorption kinetics fitted well with the pseudo-second-order model, whereas adsorption isotherm matched well with the Langmuir isothermal adsorption model, with the maximum sorption capacity of 518.39mgg(-1) at pH 5.30 and 298K. The uptake of uranium could be implied in 0.01M coexisted ions environment. Besides, the resin could be regenerated by 0.1M HNO3 and repeatedly utilized in circles. The study proved that the resin has potential application prospects for disposal of uranium(VI).

  15. The effect of chemical modification with pyromellitic anhydride on structure, function, and thermal stability of horseradish peroxidase.

    PubMed

    Hassani, Leila

    2012-06-01

    The stability of enzymes remains a critical issue in biotechnology. Compared with the strategies for obtaining stable enzymes, chemical modification is a simple and effective technique. In the present study, chemical modification of horseradish peroxidase (HRP) was carried out with pyromellitic anhydride. HRP has achieved a prominent position in the pharmaceutical, chemical, and biotechnological industries. In this study, the effect of chemical modification on thermal stability, structure, and function of the enzyme was studied by fluorescence, circular dichroism, and absorbance measurements. The results indicated a decrease in compactness of the structure and a considerable enhancement in thermal stability of HRP below 60 °C. It seems the charge replacement and introduction of the bulky group bring about the observed structural and the functional changes.

  16. Comparative effect of repeated ingestion of difructose anhydride III and palatinose on the induction of gastrointestinal symptoms in humans.

    PubMed

    Tamura, Akiko; Shiomi, Takuya; Tamaki, Noriko; Shigematsu, Norihiro; Tomita, Fusao; Hara, Hiroshi

    2004-09-01

    We evaluated the safety and change in fermentability from repeated ingestion of difructose anhydride III (DFAIII) in humans. A randomized controlled single-blind crossover study with thirteen subjects was conducted. Each subject ingested 5 g of DFAIII or palatinose daily for 12 days, before and after which the subject was loaded with 10 g of DFAIII and had breath hydrogen measured from 0 to 9 h (DL test) to evaluate the fermentability of DFAIII. The defecation frequency and abdominal symptom score were the same between each ingestion period. Moreover, DFAIII ingestion had no influence on blood test results. Only the breath hydrogen excretion in post-DFAIII ingestion was slightly higher at h 8 than the pre-ingestion. Consequently, repeated ingestion of DFAIII for 12 days was as safe as palatinose ingestion, especially with respect to abdominal symptoms and blood test results, and its high resistance to enterobacterial fermentation in humans was not impaired.

  17. Interpretations of Polymer-Polymer Miscibility.

    ERIC Educational Resources Information Center

    Olabisi, Olagoke

    1981-01-01

    Discusses various aspects of polymeric mixtures, mixtures of structurally different homopolymers, copolymers, terpolymers, and the like. Defines concepts of polymer-polymer miscibility from practical and theoretical viewpoints, and ways of predicting such miscibility. (JN)

  18. Design of amine modified polymer dispersants for liquid-phase exfoliation of transition metal dichalcogenide nanosheets and their photodetective nanocomposites

    NASA Astrophysics Data System (ADS)

    Lee, Jinseong; Hahnkee Kim, Richard; Yu, Seunggun; Babu Velusamy, Dhinesh; Lee, Hyeokjung; Park, Chanho; Cho, Suk Man; Jeong, Beomjin; Sol Kang, Han; Park, Cheolmin

    2017-12-01

    Liquid-phase exfoliation (LPE) of transition metal dichalcogenide (TMD) nanosheets is a facile, cost-effective approach to large-area photoelectric devices including photodetectors and non-volatile memories. Non-destructive exfoliation of nanosheets using macromolecular dispersing agents is beneficial in rendering the TMD nanocomposite films suitable for mechanically flexible devices. Here, an efficient LPE of molybdenum disulfide (MoS2) with an amine modified poly(styrene-co-maleic anhydride) co-polymer (AM-PSMA) is demonstrated, wherein the maleic anhydrides were converted into maleic imides with primary amines using N-Boc-(CH2) n -NH2. The exfoliation of nanosheets was facilitated through Lewis acid-base interaction between the primary amine and transition metal. The results demonstrate that the exfoliation depends upon both the fraction of primary amines in the polymer chain and their distance from the polymer backbone. Under optimized conditions of primary amine content and its distance from the backbone, AM-PSMA gave rise to a highly concentrated MoS2 nanosheet suspension that was stable for over 10 d. Exfoliation of several other TMDs was also achieved using the optimized AM-PSMA, indicating the scope of AM-PSMA applications. Furthermore, a flexible composite film of AM-PSMA and MoS2 nanosheets fabricated by vacuum-assisted filtration showed excellent photoconductive performances including a high I on/I off ratio of 102 and a fast photocurrent switching of 300 ms.

  19. Rapid microwaves synthesis of CoSi{sub x}/CNTs as novel catalytic materials for hydrogenation of phthalic anhydride

    SciTech Connect

    Zhang, Liangliang; Chen, Xiao; Jin, Shaohua; Guan, Jingchao; Williams, Christopher T.; Peng, Zhijian; Liang, Changhai

    2014-09-15

    CoSi{sub x}/CNTs catalysts with different CoSi{sub x} phases (CoSi, CoSi{sub 2}) have been rapidly synthesized via a microwave-assisted route and applied for the liquid phase hydrogenation of phthalic anhydride. The synthesized catalysts were analyzed and characterized by X-ray diffraction, X-ray photoelectron spectroscopy, transmission electron microscopy-energy dispersive X-ray spectroscopy, thermogravimetric/derivative thermogravimetric analysis. The reaction progress of cobalt silicides and the ratio of Co:Si were monitored at different microwave irradiation times by XRD, giving insight into the formation mechanism. Compared to the Co/CNTs catalyst, all the prepared CoSi{sub x}/CNTs catalysts exhibited excellent activity and good selectivity to phthalide under mild reaction conditions (180–220 °C and 4.0 MPa H{sub 2}). This novel methodology can be applied to the synthesis of other transition metal silicides such as FeSi, Ni{sub 2}Si, and Cu{sub 4}Si. - Graphical abstract: CoSi{sub x}/CNTs catalysts with different CoSi{sub x} phases (CoSi{sub 2}, CoSi) have been rapidly synthesized via microwave-assisted route, which involves the vaporization of CoCl{sub 2} and subsequent reaction of CoCl{sub 2} with Si. - Highlights: • CoSi{sub x}/CNTs catalysts have been rapid synthesized via microwave-assisted route. • The phases of CoSi{sub x} were controlled by varying microwave time and Co:Si ratio. • FeSi, Ni{sub 2}Si and Cu{sub 4}Si were also synthesized via microwave-assisted route. • CoSi{sub x}/CNTs catalysts can be applied in hydrogenation of phthalic anhydride.

  20. Modification of pineapple peel fibre with succinic anhydride for Cu2+, Cd2+ and Pb2+ removal from aqueous solutions.

    PubMed

    Hu, Xiuyi; Zhao, Mouming; Song, Guosheng; Huang, Huihua

    2011-01-01

    Research on chemical modification of pineapple peel fibre with succinic anhydride was carried out to create a novel adsorbent for Cu2+, Cd2+ and Pb2+ removal from aqueous solution. After pretreatment with iso-propyl alcohol and NaOH, pineapple peel fibre was modified via reaction with succinic anhydride for introduction of carboxylic functional groups. The modified pineapple peel fibre was characterized with Fourier transform infrared (FTIR) spectroscopy and evaluated for its adsorptive ability for Cu2+, Cd2+ and Pb2+ from synthetic metal solutions. The FTIR analysis proved the introduction of carboxylic functional groups in the backbone of the modified pineapple peel fibre. The modified pineapple peel fibre showed higher adsorptive capacity for Cu2+, Cd2+ and Pb2+ compared with raw pineapple peel and pineapple peel fibre pretreated with iso-propyl alcohol. The adsorption of Cu2+, Cd2+ and Pb2+ on the modified pineapple peel fibre depended on solution pH value, adsorption time and initial metal concentration. The maximum adsorption capacities of the modified fibre were observed at pH 5.4 for Cu2+ (27.68 +/- 0.83 mg g(-1) or 0.44 mmol g(-1)), at pH 7.5 for Cd2+ (34.18 +/- 1.02 mg g(-1) or 0.30 mmol g(-1)) and at pH 5.6 for Pb2+ (70.29 +/- 2.11 mg g(-1) or 0.34 mmol g(-1)) respectively. The adsorption followed the pseudo-second-order kinetics model and the experimental data coincided well with the Langmuir model.

  1. PolyMorphine: an innovative biodegradable polymer drug for extended pain relief

    PubMed Central

    Rosario-Meléndez, Roselin; Harris, Carolyn L.; Delgado-Rivera, Roberto; Yu, Lei; Uhrich, Kathryn E.

    2012-01-01

    Morphine, a potent narcotic analgesic used for the treatment of acute and chronic pain, was chemically incorporated into a poly(anhydride-ester) backbone. The polymer termed “PolyMorphine”, was designed to degrade hydrolytically releasing morphine in a controlled manner to ultimately provide analgesia for an extended time period. PolyMorphine was synthesized via melt-condensation polymerization and its structure was characterized using proton and carbon nuclear magnetic resonance spectroscopies, and infrared spectroscopy. The weight-average molecular weight and the thermal properties were determined. The hydrolytic degradation pathway of the polymer was determined by in vitro studies, showing that free morphine is released. In vitro cytocompatibility studies demonstrated that PolyMorphine is non-cytotoxic towards fibroblasts. In vivo studies using mice showed that PolyMorphine provides analgesia for 3 days, 20 times the analgesic window of free morphine. The animals retained full responsiveness to morphine after being subjected to an acute morphine challenge. PMID:22877734

  2. From commodity polymers to functional polymers.

    PubMed

    Xiang, Tao; Wang, Ling-Ren; Ma, Lang; Han, Zhi-Yuan; Wang, Rui; Cheng, Chong; Xia, Yi; Qin, Hui; Zhao, Chang-Sheng

    2014-04-08

    Functional polymers bear specified chemical groups, and have specified physical, chemical, biological, pharmacological, or other uses. To adjust the properties while keeping material usage low, a method for direct synthesis of functional polymers is indispensable. Here we show that various functional polymers can be synthesized by in situ cross-linked polymerization/copolymerization. We demonstrate that the polymers synthesized by the facile method using different functional monomers own outstanding pH-sensitivity and pH-reversibility, antifouling property, antibacterial, and anticoagulant property. Our study opens a route for the functionalization of commodity polymers, which lead to important advances in polymeric materials applications.

  3. From Commodity Polymers to Functional Polymers

    PubMed Central

    Xiang, Tao; Wang, Ling-Ren; Ma, Lang; Han, Zhi-Yuan; Wang, Rui; Cheng, Chong; Xia, Yi; Qin, Hui; Zhao, Chang-Sheng

    2014-01-01

    Functional polymers bear specified chemical groups, and have specified physical, chemical, biological, pharmacological, or other uses. To adjust the properties while keeping material usage low, a method for direct synthesis of functional polymers is indispensable. Here we show that various functional polymers can be synthesized by in situ cross-linked polymerization/copolymerization. We demonstrate that the polymers synthesized by the facile method using different functional monomers own outstanding pH-sensitivity and pH-reversibility, antifouling property, antibacterial, and anticoagulant property. Our study opens a route for the functionalization of commodity polymers, which lead to important advances in polymeric materials applications. PMID:24710333

  4. Molecular depth profiling of multilayer polymer films using time-of-flight secondary ion mass spectrometry.

    PubMed

    Wagner, M S

    2005-02-01

    The low penetration depth and high sputter rates obtained using polyatomic primary ions have facilitated their use for the molecular depth profiling of some spin-cast polymer films by secondary ion mass spectrometry (SIMS). In this study, dual-beam time-of-flight (TOF) SIMS (sputter ion, 5 keV SF(5)(+); analysis ion, 10 keV Ar(+)) was used to depth profile spin-cast multilayers of poly(methyl methacrylate) (PMMA), poly(2-hydroxyethyl methacrylate) (PHEMA), and trifluoroacetic anhydride-derivatized poly(2-hydroxyethyl methacrylate) (TFAA-PHEMA) on silicon substrates. Characteristic positive and negative secondary ions were monitored as a function of depth using SF(5)(+) primary ion doses necessary to sputter through the polymer layer and uncover the silicon substrate (>5 x10(14) ions/cm(2)). The sputter rates of the polymers in the multilayers were typically less than for corresponding single-layer films, and the order of the polymers in the multilayer affected the sputter rates of the polymers. Multilayer samples with PHEMA as the outermost layer resulted in lowered sputter rates for the underlying polymer layer due to increased ion-induced damage accumulation rates in PHEMA. Additionally, the presence of a PMMA or PHEMA overlayer significantly decreased the sputter rate of TFAA-PHEMA underlayers due to ion-induced damage accumulation in the overlayer. Typical interface widths between adjacent polymer layers were 10-15 nm for bilayer films and increased with depth to approximately 35 nm for the trilayer films. The increase in interface width and observations using optical microscopy showed the formation of sputter-induced surface roughness during the depth profiles of the trilayer polymer films. This study shows that polyatomic primary ions can be used for the molecular depth profiling of some multilayer polymer films and presents new opportunities for the analysis of thin organic films using TOF-SIMS.

  5. Poly(2-vinylnaphthalene-alt-maleic acid)-graft polystyrene as a photoactive polymer micelle and stabilizer for polystyrene latexes

    SciTech Connect

    Cao, T.; Yin, W.; Webber, S.E. )

    1994-12-05

    Polymerization of maleic anhydride and 2-vinylnaphthalene produces alternating polymers. Imidization of the polymer with amino-terminated polystyrene yields different loadings of an alternating polymer with polystyrene combs''. Upton rigorous hydrolysis one obtains poly(2-vinylnaphthalene-alt-maleic acid)-graft-polystyrene (P2VNMA-PS), which is a fluorescent polymer with unusual solution properties and with significant surface activity. P2VNMA-PS forms a small micelle structure in solution or can be used as a surfactant for an emulsion polymerization of polystyrene (no cosurfactant is required), producing monodisperse latex particles which are stable for pH > 3.9. Centrifugation shows that >90% of the P2VNMA-PS is associated with the latex particles. Fluorescence quenching studies of the naphthalene excimer with Tl[sup +] indicate that approximately 84% and 77% of the naphthalene groups remain exposed to the aqueous phase when this polymer is micellized or incorporated onto a latex particle, respectively. These data imply that the P2VNMA-PS polymer is permanently associated with the exterior of the latex particle, as one would expect given the amphiphilic nature of this polymer.

  6. Shape memory polymers

    DOEpatents

    Wilson, Thomas S.; Bearinger, Jane P.

    2017-08-29

    New shape memory polymer compositions, methods for synthesizing new shape memory polymers, and apparatus comprising an actuator and a shape memory polymer wherein the shape memory polymer comprises at least a portion of the actuator. A shape memory polymer comprising a polymer composition which physically forms a network structure wherein the polymer composition has shape-memory behavior and can be formed into a permanent primary shape, re-formed into a stable secondary shape, and controllably actuated to recover the permanent primary shape. Polymers have optimal aliphatic network structures due to minimization of dangling chains by using monomers that are symmetrical and that have matching amine and hydroxl groups providing polymers and polymer foams with clarity, tight (narrow temperature range) single transitions, and high shape recovery and recovery force that are especially useful for implanting in the human body.

  7. Shape memory polymers

    DOEpatents

    Wilson, Thomas S.; Bearinger, Jane P.

    2015-06-09

    New shape memory polymer compositions, methods for synthesizing new shape memory polymers, and apparatus comprising an actuator and a shape memory polymer wherein the shape memory polymer comprises at least a portion of the actuator. A shape memory polymer comprising a polymer composition which physically forms a network structure wherein the polymer composition has shape-memory behavior and can be formed into a permanent primary shape, re-formed into a stable secondary shape, and controllably actuated to recover the permanent primary shape. Polymers have optimal aliphatic network structures due to minimization of dangling chains by using monomers that are symmetrical and that have matching amine and hydroxyl groups providing polymers and polymer foams with clarity, tight (narrow temperature range) single transitions, and high shape recovery and recovery force that are especially useful for implanting in the human body.

  8. The role of nanoclay on the deformation behavior of polypropylene/maleic anhydride modified polypropylene films and fibers in full and partially molten state processing

    NASA Astrophysics Data System (ADS)

    Fujiyama-Novak, Jane Hitomi

    The behavior of polypropylene nanocomposite fibers and films under uniaxial deformation in a partial and fully molten state was investigated. A fiber that exits the die was found to contain orientation gradient in the radial direction that is preserved even after solidification without application of a take up. The shearing effect in the die results in a band of oriented outer layers in which broad surfaces of the clay particles become parallel to the surface of the fibers. The polymer phase trapped between these particles exhibit moderate to high preferential orientation levels. Conversely, in the core low levels of preferred orientation were found in both the clay and the polymer phases. Upon application of take up, the presence of clay particles substantially enhances the orientation of amorphous and crystalline phases in PP/PPgMA (maleic anhydride modified polypropylene) fibers. This is due to the substantial decrease in chain relaxation in the proximity of the clay platelets and enhancement of orientation in the polymer phase in the vicinity of particles that create amplified deformation field by their relative motions. Measurements of the clay orientation in the melt-spun fibers as they undergo "confined melting" in constrained state revealed that these naturally anisotropic nanoplatelets contribute positively to the birefringence of the fibers. A hybrid real-time spectral birefringence technique depolarized light intensity method was used to capture the mechanistic changes that take place during heating, stretching, holding and cooling cycles of PP/PPGMA and nanocomposite films in a partially molten state. During the heating stage, the birefringence and the degree of melting of the as-cast films were determined by real-time depolarizing light intensity technique. The results indicate the initial fraction of crystallites, which govern the deformation behavior of the PP films, remains in dynamic equilibrium with the molten phase prior to the deformation after

  9. 54 FR 38044: National Emission Standards for Hazardous Air Pollutants; Benzene Emissions From Maleic Anhydride Plants, Ethylbenzene/Styrene Plants, Benzene Storage Vessels, Benzene Equipment Leaks, and Coke By- Product Recovery Plants

    EPA Pesticide Factsheets

    Final Rule on National Emission Standards for Hazardous Air Pollutants; Benzene Emissions From Maleic Anhydride Plants, Ethylbenzene/Styrene Plants, Benzene Storage Vessels, Benzene Equipment Leaks, and Coke By-Product Recovery Plants.

  10. Mixed anhydrides (phosphoric-carboxyl) are also formed in the esterification of 5'-amp with n-acetylaminoacyl imidazolides - Implications regarding the origin of protein synthesis

    NASA Technical Reports Server (NTRS)

    Wickramasinghe, Nalinie S. M. D.; Lacey, James C., Jr.

    1992-01-01

    Procedure for the formation of aminoacyl esters of monoribonucleotides with aminoacyl imidazolides were first reported by Gottikh et al. (1970) and summarized in 1970. This reaction has been widely used by us and numbers of other workers as a convenient means of preparing aminoacyl esters of nucleotides. We have previously reported that, under conditions of excess imidazolide, large amounts of bis 2', 3' esters are formed in addition to the monoesters. However, to our knowledge, no one has reported that in addition to the esters, relatively large amounts of the mixed anhydride, with the amino acid carboxyl attached to the phosphate, are also formed at short reaction times. We report here on the relative amounts of anhydride and esters formed in this reaction of racemic mixtures of eleven N-acetyl amino acid imidazolides with 5'-AMP and discuss the relevance of the findings to the origin of protein synthesis.

  11. Electronic Effects of Aluminum Complexes in the Copolymerization of Propylene Oxide with Tricyclic Anhydrides: Access to Well-Defined, Functionalizable Aliphatic Polyesters.

    PubMed

    Van Zee, Nathan J; Sanford, Maria J; Coates, Geoffrey W

    2016-03-02

    The synthesis of well-defined and functionalizable aliphatic polyesters remains a key challenge in the advancement of emerging drug delivery and self-assembly technologies. Herein, we investigate the factors that influence the rates of undesirable transesterification and epimerization side reactions at high conversion in the copolymerization of tricyclic anhydrides with excess propylene oxide using aluminum salen catalysts. The structure of the tricyclic anhydride, the molar ratio of the aluminum catalyst to the nucleophilic cocatalyst, and the Lewis acidity of the aluminum catalyst all influence the rates of these side reactions. Optimal catalytic activity and selectivity against these side reactions requires a careful balance of all these factors. Effective suppression of undesirable transesterification and epimerization was achieved even with sterically unhindered monomers using a fluorinated aluminum salph complex with a substoichiometric amount of a nucleophilic cocatalyst. This process can be used to synthesize well-defined block copolymers via a sequential addition strategy.

  12. The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course

    NASA Astrophysics Data System (ADS)

    McDaniel, Keith F.; Weekly, R. Matthew

    1997-12-01

    The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session. The resulting product, which contains four new stereocenters, crystallizes upon cooling of the reaction mixture to give the pure product. Careful analysis of the 1H nuclear magnetic resonance spectrum, which contains a variety of cleanly split signals with no overlapping peaks, allows for assignment of all twelve hydrogens. A COSY spectrum of the product is also presented and interpreted.

  13. Mixed anhydrides (phosphoric-carboxyl) are also formed in the esterification of 5'-amp with n-acetylaminoacyl imidazolides - Implications regarding the origin of protein synthesis

    NASA Technical Reports Server (NTRS)

    Wickramasinghe, Nalinie S. M. D.; Lacey, James C., Jr.

    1992-01-01

    Procedure for the formation of aminoacyl esters of monoribonucleotides with aminoacyl imidazolides were first reported by Gottikh et al. (1970) and summarized in 1970. This reaction has been widely used by us and numbers of other workers as a convenient means of preparing aminoacyl esters of nucleotides. We have previously reported that, under conditions of excess imidazolide, large amounts of bis 2', 3' esters are formed in addition to the monoesters. However, to our knowledge, no one has reported that in addition to the esters, relatively large amounts of the mixed anhydride, with the amino acid carboxyl attached to the phosphate, are also formed at short reaction times. We report here on the relative amounts of anhydride and esters formed in this reaction of racemic mixtures of eleven N-acetyl amino acid imidazolides with 5'-AMP and discuss the relevance of the findings to the origin of protein synthesis.

  14. Peroxycarboxylic Nitric Anhydrides as Markers of Anthropogenic and Biogenic VOC Photo-oxidation in the Alberta Oil Sands

    NASA Astrophysics Data System (ADS)

    Osthoff, H. D.; Huo, J. A.; Tokarek, T. W.; Odame-Ankrah, C. A.; Saowapon, M. T.; Chen, X.

    2014-12-01

    The peroxycarboxylic nitric anhydrides (molecular formula RC(O)O2NO2) are well-known byproducts of the photo-oxidation chemistry between NOx and volatile organic compounds (VOCs) that produces ozone (O3) and photochemical smog. More than 43 different PAN species are known; their relative abundances are chemical markers of the types and quantities of the VOCs involved in the O3-formation process. For example, MPAN (R: CH2=C(CH3)-) is primarily derived from isoprene and thus a marker of biogenic VOC oxidation, whereas PPN (R: C2H5-) is a photo-oxidation byproduct of anthropogenic VOCs. In the summer of 2013 an intensive air quality measurement campaign was conducted to investigate the impacts of emissions from the Alberta oil sands mining operations on the chemical composition of ambient air. As part of this effort, several peroxycarboxylic nitric anhydrides, specifically PAN (R: CH3-), PPN, MPAN, APAN (R: CH2=CH-), and PiBN (R: iC3H7-), were quantified by gas chromatography with electron capture detection at the AMS13 ground site near Fort McKay, Alberta. Furthermore, total peroxyacyl nitrates (ΣPAN) were quantified by thermal dissociation cavity ring-down spectroscopy (TD-CRDS). PAN mixing ratios typically peaked in the mid-afternoon (maximum PAN mixing ratio of 0.85 ppbv), constituting up to 25% of total odd nitrogen (NOy), and were usually below detection limits at night. ΣPAN was generally greater than the amount calculated by summation of individually measured PANs (SPANi) suggesting the presence of PAN species not measured by GC. During times of active photo-oxidation chemistry, the PPN:PAN and MPAN:PAN ratios varied considerably between days, depending on air mass origin and VOC composition. A linear combination model (LCM) was used to assess regional O3 production from the oxidation of biogenic hydrocarbons (via MPAN) relative to that of anthropogenic hydrocarbons (via PPN). The relative contribution of anthropogenic VOCs to regional O3 production varied

  15. Effect of hydrostatic pressure, temperature, and solvent on the rate of the Diels-Alder reaction between 9,10-anthracenedimethanol and maleic anhydride

    NASA Astrophysics Data System (ADS)

    Kiselev, V. D.; Kornilov, D. A.; Anikin, O. V.; Latypova, L. I.; Konovalov, A. I.

    2017-03-01

    The rate of the reaction between 9,10-anthracenedimethanol and maleic anhydride in 1,4-dioxane, acetonitrile, trichloromethane, and toluene is studied at 25, 35, 45°C in the pressure range of 1-1772 bar. The rate constants, enthalpies, entropies and activation volumes are determined. It is shown that the rate of reaction with 9,10-anthracenedimethanol is approximately one order of magnitude higher than with 9-anthracenemethanol.

  16. [Influence of low concentration of sulphuric anhydride on metabolic status of peripheral blood lymphocytes in guinea pigs sensibilised with a biological allergen].

    PubMed

    Dolgushin, M V; Sosedova, L M

    2005-01-01

    The influence of sulphuric anhydride (2-4 mg/m3) on the metabolic status of peripheral blood lymphocytes of sensibilised guinea pigs with different sequence of biological (allergenic) and chemical exposure has been studied. The metabolic state was evaluated by histochemical assay of succinate and lactate dehydrogenases and acid phosphatase. The changes in activities of dehydrogenases were found to indicate a definite relationship with specific responses of combined effects of different factors.

  17. One-pot synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion.

    PubMed

    Ji, Fei; Lv, Mei-Fang; Yi, Wen-Bin; Cai, Chun

    2014-08-14

    An efficient and practical two-step process has been developed for the synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion in one pot. This regioselective procedure could construct a wide range of 2-amino-4(3H)-quinazolinones in moderate to excellent yields. Furthermore, the methodology also had distinct advantages of easily accessible starting materials and operational simplicity.

  18. Polymer Functionalized Nanoparticles in Polymer Nanocomposites

    NASA Astrophysics Data System (ADS)

    Jayaraman, Arthi

    2013-03-01

    Significant interest has grown around the ability to control spatial arrangement of nanoparticles in a polymer nanocomposite to engineer materials with target properties. Past work has shown that one could achieve controlled assembly of nanoparticles in the polymer matrix by functionalizing nanoparticle surfaces with homopolymers. This talk will focus on our recent work using Polymer Reference Interaction Site Model (PRISM) theory and Monte Carlo simulations and GPU-based molecular dynamics simulations to specifically understand how heterogeneity in the polymer functionalization in the form of a) copolymers with varying monomer chemistry and monomer sequence, and b) polydispersity in homopolymer grafts can tune effective interactions between functionalized nanoparticles, and the assembly of functionalized nanoparticles.

  19. Lipid-absorbing Polymers

    NASA Technical Reports Server (NTRS)

    Marsh, H. E., Jr.; Wallace, C. J.

    1973-01-01

    The removal of bile acids and cholesterol by polymeric absorption is discussed in terms of micelle-polymer interaction. The results obtained with a polymer composed of 75 parts PEO and 25 parts PB plus curing ingredients show an absorption of 305 to 309%, based on original polymer weight. Particle size effects on absorption rate are analyzed. It is concluded that crosslinked polyethylene oxide polymers will absorb water, crosslinked polybutadiene polymers will absorb lipids; neither polymer will absorb appreciable amounts of lipids from micellar solutions of lipids in water.

  20. A versatile strategy for grafting polymers to wood cell walls.

    PubMed

    Keplinger, T; Cabane, E; Chanana, M; Hass, P; Merk, V; Gierlinger, N; Burgert, I

    2015-01-01

    The hierarchical structure of wood is composed of a cellulose skeleton of high structural order at various length scales. At the nanoscale and microscale the specific structural features of the cells and cell walls result in a lightweight structure with an anisotropic material profile of excellent mechanical performance. By being able to specifically functionalize wood at the level of cell and cell walls one can insert new properties and inevitably upscale them along the intrinsic hierarchical structure, to a level of large-scale engineering materials applications. For this purpose, however, precise control of the spatial distribution of the modifying substances in the complex wood structure is needed. Here we demonstrate a method to insert methacryl groups into wood cell walls using two different chemistry routes. By using these methacryl groups as the anchor points for grafting, various polymers can be inserted into the wood structure. Strikingly, depending on the methacryl precursor, the spatial distribution of the polymer differs strongly. As a proof of concept we grafted polystyrene as a model compound in the second modification step. In the case of methacryloyl chloride the polymer was located mainly at the interface between the cell lumina and the cell wall covering the inner surface of the cells and being traceable up to 2-3 μm in the cell wall, whereas in the case of methacrylic anhydride the polymer was located inside the whole cell wall. Scanning electron microscopy, Fourier transform infrared spectroscopy and especially Raman spectroscopy were used for an in-depth analysis of the modified wood at the cell wall level. Copyright © 2014 Acta Materialia Inc. Published by Elsevier Ltd. All rights reserved.

  1. Modulated fibronectin anchorage at polymer substrates controls angiogenesis.

    PubMed

    Pompe, Tilo; Markowski, Manuela; Werner, Carsten

    2004-01-01

    A set of maleic anhydride copolymer thin films exhibiting well-defined differences in hydrophobicity and reactivity was compared with respect to the capability of supporting angiogenesis of human endothelial cells grown in contact. The physicochemical surface characteristics of the polymer substrates were found to modulate the anchorage of immobilized fibronectin. This was demonstrated to determine whether endothelial cells grow as a monolayer or form capillary networks. Enhanced reorganization of predeposited fibronectin into cell-matrix adhesions and slightly elevated levels of membrane-type matrix metalloproteinase 14 (MMP-14) occurred with weakly bound fibronectin layers where angiogenesis was most obvious. The key role of fibronectin-substrate binding for angiogenesis-under otherwise constant conditions-was further confirmed by the absence of variations in the expression of angiogenesis-related integrins (alpha(v)beta(3)) and in the secretion of the metalloproteinase MMP-2. Altogether, the results of this study point at the relevance of physicochemical surface characteristics of polymer materials for the stimulation of angiogenesis.

  2. Carbon Nanotubes Embedded in Oriented Polymer Nanofibers by Electrospinning

    NASA Astrophysics Data System (ADS)

    Cohen, Yachin; Dror, Yael; Khalfin, Rafail L.; Salalha, Wael; Yarin, Alexander L.; Zussman, Eyal

    2004-03-01

    The electrospinning process was used successfully to fabricate nanofibers of poly(ethylene oxide) [PEO] in which carbon nanotubes, either multi-walled (MWCNT) or single-walled (SWCNT) are embedded. MWCNTs were dispersed in water using SDS or Gum Arabic - a highly branched polyelectrolyte. Aqueous dispersion of SWCNT's was achieved using an alternating copolymer of styrene and maleic anhydride, hydrolyzed with NaOH. The focus of this work is on the development of axial orientations in the multi-component nanofibers. The degree of orientation of polymers, surfactants and nanotubes was studied using X-ray diffraction and transmission electron microscopy. Individual nanotubes were successfully embedded in the polymer nanofibers with good axial alignment. A high degree of alignment of PEO crystals and SDS layers was also found in the electrospun nanofibers containing SWCNT's. Oriented ropes of the nanofibers were fabricated in a converging electric field by a rotating disc with a tapered edge. These results can lead to further usage of the nanofibers with embedded carbon nanotubes in applications such as nano-scale energy storage devices.

  3. Microencapsulation of white champaca (Michelia alba D.C.) extract using octenyl succinic anhydride (OSA) starch for controlled release aroma.

    PubMed

    Samakradhamrongthai, Rajnibhas; Thakeow, Prodpran; Kopermsub, Phikunthong; Utama-Ang, Niramon

    2016-12-01

    The objective of the study was to optimise the encapsulation of Michelia alba D.C. (MAD) extract using octenyl succinic anhydride (OSA) starch. The MAD extract (5-10 g/100 g of dry starch) and the OSA starch (25-100 g/100 ml of water) was used in microcapsule preparation and analysed for the physicochemical and encapsulation properties. The optimised formula using the MAD extract and the OSA starch were 15.00 g/100 g of dry starch and 96.32 g/100 g water, which provided the highest in yield recovery (40.65% ± 0.99) and encapsulation efficiency (68.91% ± 1.50), with the lowest moisture content (3.19% ± 0.06) and water activity (0.236 ± 0.004). The aroma release from the optimum encapsulated powder in simulated artificial saliva fluid (SSF) suggested that linalool retention in microcapsules was higher than verbenone and 2-methyl butanoic acid. This study shows that the optimised formulation of MAD encapsulated flavour powder was found to be effective for controlling the aroma release.

  4. Novel thermosensitive hydrogels based on methoxy polyethylene glycol-co-poly(lactic acid-co-aromatic anhydride) for cefazolin delivery.

    PubMed

    Lai, Po-Liang; Hong, Ding-Wei; Ku, Kuan-Lin; Lai, Zhi-Teng; Chu, I-Ming

    2014-04-01

    Thermosensitive micelles composed of a copolymer of methoxy polyethylene glycol (mPEG), polylactic acid (PLA), and 1,6-bis (p-carboxyphenoxy) hexane (CPH), namely methoxy polyethylene glycol-co-polylactic acid-co-aromatic anhydride (mPEG-PLCPHA), were fabricated for application as a promising hydrophilic drug carrier. The copolymer can self-assemble into micelles in PBS by hydrophobic interaction. The diameters of these micelles increased as the environmental temperature increased. An increase in viscosity with sol-to-gel transition occurred as temperature increased from room temperature to body temperature. During the in vitro degradation process, hydrogels demonstrated a more stable degradation rate. Both in vitro and in vivo cytotoxicity results showed that the materials had excellent biocompatibility due to less acidic products formation. In vitro cefazolin release profiles showed a stable release for 30 days. The hydrogel encapsulated cefazolin exhibited a good antibacterial effect. Based on these results, mPEG-PLCPHA can serve as an injectable depot gel for drug delivery. In this study, thermosensitive hydrogel encapsulated cefazolin was found to exhibit good antibacterial effects with sustained levels for up to 30 days, enabling the development of an injectable depot gel for long-term drug delivery. © 2013.

  5. Experimental and theoretical study on the reaction of N3-phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride

    NASA Astrophysics Data System (ADS)

    Modzelewska-Banachiewicz, Bożena; Paprocka, Renata; Mazur, Liliana; Saczewski, Jarosław; Kutkowska, Jolanta; Stępień, Dorota K.; Cyrański, Michał

    2012-08-01

    Two new 1,2,4-triazole-containing alkenoic acid derivatives were obtained from the reaction of N-phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride, depending on the reaction conditions. The structures of 2-((4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl)methyl)acrylic acid or (E)-2-methyl-3(4-phenyl-5-(pyridine-2-yl)-4H-1,2,4-triazol-3-yl)acrylic acid were confirmed by means of 1D and 2D NMR spectroscopic data as well as by single-crystal X-ray diffraction analysis. The experiential 1H and 13C chemical shifts were compared with those calculated with B3LYP, EDF1, and EDF2 density functional theories. The theoretical study of the observed terminal-to-internal alkene isomerization was performed with density functional (DFT) B3LYP/6-31+G∗ method using SM8 water and DMF solvation models. Antimicrobial activities of the newly prepared alkenoic acid derivatives were verified experimentally by a broth microdilution method.

  6. Estimating regio and stereoselectivity in [4+2] cycloadditions of vinyl-substituted cyclic dienes with maleic anhydride.

    PubMed

    Gayatri, Gaddamanugu; Sastry, G Narahari

    2009-10-29

    Density functional theory calculations are performed to examine the regio and stereoselective preferences in [4+2] cycloaddition reactions of vinyl cyclopentadiene (1 and 2) and vinyl heterocyclic (1-N, 1-O, 1-S, 2-N, 2-O and 2-S) systems with maleic anhydride. Stepwise and concerted pathways of model systems 1 and 2 as dienes with ethylene as dienophile reveal that the reactions proceed through asynchronous and concerted pathway. 3-Vinyl systems (2) are predicted to be more reactive compared to 2-vinyl systems (1). The regio and stereoselective preferences are evaluated based on activation energies, reaction energies, density functional based descriptors and atoms in molecules analysis. In all cases, extra-annular cycloadducts are more feasible compared to intra-annular cycloadducts. Stereoselectivity depends on the favorable secondary orbital interactions. Solvents such as water, tetrahydrofuran, acetone, and dimethyl sulphoxide are employed to understand the effects of solvents on the cycloadduct formation. The computational results thus obtained are compared with the earlier experimental observations that are available.

  7. Preparation of fenofibrate dry emulsion and dry suspension using octenyl succinic anhydride starch as emulsifying agent and solid carrier.

    PubMed

    Pongsamart, Kasama; Kleinebudde, Peter; Puttipipatkhachorn, Satit

    2016-02-10

    Purpose of this study was to investigate the ability of octenyl succinic anhydride (OSA) starch as emulsifier and solid carrier in dry emulsion (DE) and dry suspension (DS) formulations. Fenofibrate (FF) was loaded at lower and higher than its saturation concentration in oil phase to prepare the DE and DS by spray drying method. The DE and DS were successfully prepared with 36-48% and 46% production yield, respectively. After reconstitution in water, the emulsion with mean droplet size of 1-2 μm was obtained. Solid state characterization revealed the amorphous state of FF and the crystalline state of OSA starch in both DE and DS formulations. Both DE and DS enhanced FF dissolution rate compared to pure material and DS showed the highest dissolution rate. The DE and DS could be compressed to the tablets with acceptable disintegration time and without changeable dissolution profile. Moreover, the dissolution profiles of both DE and DS remained unchanged after 2 months storage at 40 °C. Copyright © 2015 Elsevier B.V. All rights reserved.

  8. Thermal decomposition behaviors and kinetic properties of 1,8-naphthalic anhydride loaded dense nano-silica hybrids

    NASA Astrophysics Data System (ADS)

    Wang, Jinpeng; Sun, Jihong; Wang, Feng; Ren, Bo

    2013-06-01

    A certain amount of (3-aminopropyl)triethoxysilane (APTES) and various capacity of 1,8-naphthalic anhydride (NA) were employed to modify and then graft onto the surface of the dense nano-silica spheres (DNSS) via a post-grafting method, and thereby, a novel luminescent density nano-silica hybrid materials have been successfully synthesized. Meanwhile, the structures and properties of obtained hybrid DNSS were characterized by XRD, TEM, N2 sorption, FT-IR, and TG analysis. Furthermore, the thermal stability of before and after modification were demonstrated by using both Kissinger methods and Ozawa-Flynn-Wall methods. Particularly, the thermal decomposition behaviors of amino-modified groups and NA-grafted organic molecules were emphasized based on the TG and DTG analysis and then the related mechanism was put forward according to Coats and Redfern methods. Finally, as a comparison, the obtained results and the proposed decomposition mechanism of hybrid DNSS with non-pores were discussed with that of mesopores silicas in details.

  9. Study of yellow luminescence of binary terbium complexes based on 3,3',4,4'-biphthalic anhydride.

    PubMed

    Lin, Meijuan; Wang, Xiaoping; Tang, Qiang; An, Qi; Zeng, Huijuan; Ling, Qidan

    2014-01-20

    Three novel binary Tb(III) complexes (TbL2, TbL, and Tb2L; L=3,3',4,4'-biphenyl tetracarboxylic ligand) were synthesized by changing the molar ratio of Tb(III) to 3,3',4,4'-biphthalic anhydride (BPDA) (1∶2, 1∶1, and 2∶1, respectively). IR spectra indicate that there are two coordination modes of the carboxylate ligands with Tb3+ ions in the complexes. Most of them are in bridging mode; the others are in chelating mode. These complexes all have good thermal stability. The photophysical properties of these complexes are studied in detail using UV absorption spectra, fluorescence spectra, and transient fluorescence spectra. The results indicate that the photoluminescence properties of the complexes depend strongly on the molar ratio of Tb(III) to BPDA. When the molar ratio of Tb(III) to BPDA is 1∶1, complex TbL exhibits the strongest yellow light emission among the three Tb(III) complexes. However, complex Tb2L exhibits a weaker yellowish-green light emission when the molar ratio of Tb(III) to BPDA is 2∶1. The phenomenon of the yellow emission from terbium complexes is rarely reported.

  10. Anhydride-functional silane immobilized onto titanium surfaces induces osteoblast cell differentiation and reduces bacterial adhesion and biofilm formation.

    PubMed

    Godoy-Gallardo, Maria; Guillem-Marti, Jordi; Sevilla, Pablo; Manero, José M; Gil, Francisco J; Rodriguez, Daniel

    2016-02-01

    Bacterial infection in dental implants along with osseointegration failure usually leads to loss of the device. Bioactive molecules with antibacterial properties can be attached to titanium surfaces with anchoring molecules such as silanes, preventing biofilm formation and improving osseointegration. Properties of silanes as molecular binders have been thoroughly studied, but research on the biological effects of these coatings is scarce. The aim of the present study was to determine the in vitro cell response and antibacterial effects of triethoxysilypropyl succinic anhydride (TESPSA) silane anchored on titanium surfaces. X-ray photoelectron spectroscopy confirmed a successful silanization. The silanized surfaces showed no cytotoxic effects. Gene expression analyses of Sarcoma Osteogenic (SaOS-2) osteoblast-like cells cultured on TESPSA silanized surfaces reported a remarkable increase of biochemical markers related to induction of osteoblastic cell differentiation. A manifest decrease of bacterial adhesion and biofilm formation at early stages was observed on treated substrates, while favoring cell adhesion and spreading in bacteria-cell co-cultures. Surfaces treated with TESPSA could enhance a biological sealing on implant surfaces against bacteria colonization of underlying tissues. Furthermore, it can be an effective anchoring platform of biomolecules on titanium surfaces with improved osteoblastic differentiation and antibacterial properties.

  11. Rapid microwaves synthesis of CoSix/CNTs as novel catalytic materials for hydrogenation of phthalic anhydride

    NASA Astrophysics Data System (ADS)

    Zhang, Liangliang; Chen, Xiao; Jin, Shaohua; Guan, Jingchao; Williams, Christopher T.; Peng, Zhijian; Liang, Changhai

    2014-09-01

    CoSix/CNTs catalysts with different CoSix phases (CoSi, CoSi2) have been rapidly synthesized via a microwave-assisted route and applied for the liquid phase hydrogenation of phthalic anhydride. The synthesized catalysts were analyzed and characterized by X-ray diffraction, X-ray photoelectron spectroscopy, transmission electron microscopy-energy dispersive X-ray spectroscopy, thermogravimetric/derivative thermogravimetric analysis. The reaction progress of cobalt silicides and the ratio of Co:Si were monitored at different microwave irradiation times by XRD, giving insight into the formation mechanism. Compared to the Co/CNTs catalyst, all the prepared CoSix/CNTs catalysts exhibited excellent activity and good selectivity to phthalide under mild reaction conditions (180-220 °C and 4.0 MPa H2). This novel methodology can be applied to the synthesis of other transition metal silicides such as FeSi, Ni2Si, and Cu4Si.

  12. Olefin-maleic-anhydride copolymer based additives: a novel approach for compatibilizing blends of waste polyethylene and crumb rubber.

    PubMed

    Tóth, Balázs; Varga, Csilla; Bartha, László

    2015-04-01

    In our work processing conditions and mechanical properties of waste polyethylene (PE)/crumb rubber (CR) blends have been improved by new types of compatibilizing additives synthesized from experimental olefin-maleic-anhydride copolymers at our laboratory. Compatibilizing additives have been introduced into the PE/CR blends in 0.2 wt% while CR concentration has been varied between 10 and 50 wt%. For comparison of the effects commercially available MA-g-PO type compatibilizing additives have also been applied. Tensile and Charpy impact tests of the compression moulded samples have been carried out. Several experimental additives have enhanced properties of the PE/CR blends either from the point of view of tensile or Charpy impact strength while commercial additives have had improving effects only on one of the abovementioned mechanical properties but not for both of them simultaneously. Since good mechanical properties could be achieved by our experimental compatibilizers good adhesion in the waste PE/CR samples have been considered and was proven by SEM graphs either.

  13. Modification of bovine heart succinate dehydrogenase with ethoxyformic anhydride and rose bengal: evidence for essential histidyl residues protectable by substrates.

    PubMed

    Hederstedt, L; Hatefi, Y

    1986-06-01

    Purified and membrane-bound succinate dehydrogenase (SDH) from bovine heart mitochondria was inhibited by the histidine-modifying reagents ethoxyformic anhydride (EFA) and Rose Bengal in the presence of light. Succinate and competitive inhibitors protected against inhibition, and decreased the number of histidyl residues modified by EFA. The essential residue modified by EFA was not the essential thiol of SDH, but modification of the essential thiol abolished the protective effect of malonate against inhibition of SDH by EFA. The EFA inhibition was reversed by hydroxylamine nearly completely when the inhibition was less than or equal to 35%, and only partially when the inhibition was more extensive. The uv spectrum of EFA-modified SDH before and after hydroxylamine treatment suggested that extensive inhibition of SDH with EFA may result in ethoxyformylation at both imidazole nitrogens of histidyl residues. Such a modification is not reversed by hydroxylamine. Succinate dehydrogenases and fumarate reductases from several different sources have similar compositions, and the two enzymes from Escherichia coli have considerable homology in the amino acid composition of their respective flavoprotein and iron-sulfur protein subunits. In the former, there is a short stretch containing conserved histidine, cysteine, and arginine residues. These residues, if also conserved in the bovine enzyme, may be the essential active site residues suggested by this work (histidine) and previously (cysteine, arginine).

  14. Interaction of ozone exposure with airway hyperresponsiveness and inflammation induced by trimellitic anhydride in sensitized guinea pigs

    SciTech Connect

    Sun, Jian; Chung, K.Fan

    1997-09-01

    The effect of prior ozone (O{sub 3}) exposure on airway hyperresponsiveness and inflammation induced by trimellitic anhydride (TMA) has been investigated in TMA-sensitized guinea pigs. Airway responsiveness was measured as the concentration of acetylcholine needed to increase baseline lung resistance (RL) by 300% (PC300). Ozone (3 ppm, for 3 h) caused an increase in-log PC300 at 1 h after exposure, with return of -log PC300 to control levels at 8 h. Ozone also increased baseline RL at 8 h. TMA challenge increase -log PC300 in TMA-sensitized guinea pigs at 8 h after challenge from 3.85 {+-} 0.09 to 4.11 {+-} 0.09. Ozone exposure prior to TMA challenge prevented the induction of airway hyperresponsiveness with a mean -log PC300 of 3.51 {+-} 0.20, which was not different from that of control TMA-Sensitized group. Baseline RL was significantly higher in ozone-pretreated animals after TMA challenge when compared to those of either control or challenged with TMA alone. Ozone had no effect on TMA challenge-induced BAL eosinophilia and neutrophilia. We conclude that a single exposure to ozone inhibits the increase in airway responsiveness, but increases the bronchoconstrictor response induced by TMA in TMA-Sensitized guinea pigs; however, the inflammatory airway response to TMA is unchanged by preexposure to ozone. 29 refs., 2 figs., 1 tab.

  15. A 3-week dietary safety study of octenyl succinic anhydride (OSA)-modified starch in neonatal farm piglets.

    PubMed

    Mahadevan, Brinda; Thorsrud, Bjorn A; Brorby, Gregory P; Ferguson, Heather E

    2014-10-01

    Octenyl succinic anhydride (OSA)-modified starch functions as both an emulsifier and emulsion stabilizer in foods, and is intended for use in infant formula, follow-on formula, and formulae for special medical purposes. These formulae predominantly include extensively hydrolyzed protein or free amino acids, rather than intact protein, which otherwise would provide emulsifying functionality. The study objectives were to evaluate (1) the safety of OSA-modified starch after three weeks of administration to neonatal farm piglets, beginning 2 days after birth and (2) the impact of OSA-modified starch on piglet growth. OSA-modified starch was added to formula at concentrations of 2, 4, and 20 g/L. The vehicle control, low-dose, and mid-dose diets were supplemented with Amioca™ Powder to balance the nutritional profiles of all formulations. There were no test article-related effects of any diet containing OSA-modified starch on piglet growth and development (clinical observations, body weight, feed consumption), or clinical pathology parameters (hematology, clinical chemistry, coagulation, urinalysis). In addition, there were no adverse effects at terminal necropsy (macro- and microscopic pathology evaluations). Therefore, dietary exposure to OSA-modified starch at concentrations up to 20 g/L was well tolerated by neonatal farm piglets and did not result in adverse health effects or impact piglet growth. Copyright © 2014 Elsevier Ltd. All rights reserved.

  16. Modification of pineapple peel fiber as metal ion adsorbent through reaction with succinic anhydride in pyridine and dimethyl sulfoxide solvents.

    PubMed

    Hu, Xiuyi; Zhao, Mouming; Huang, Huihua

    2010-08-01

    Reactions between saponified pineapple peel fiber (SPPF) and succinic anhydride were performed in refluxed pyridine and dimethyl sulfoxide to obtain modified pineapple peel fiber in pyridine (MPPF-PY) and modified pineapple peel fiber in dimethyl sulfoxide at room temperature (MPPF-DMRT) and at 70 degrees C (MPPF-DM70) as novel metal ionic adsorbents. The modified pineapple peel fibers were characterized by Fourier transform infrared (FTIR) and X-ray diffraction (XRD). The MPPF-PY, MPPF-DMRT, and MPPF-DM70 showed higher Cu2+, Cd2+, and Pb2+ adsorption capacity than raw pineapple peel fiber (RPPF) and SPPF. Dimethyl sulfoxide favored introduction of a carboxylic function group into pineapple peel fiber compared with pyridine. The elevated reaction temperature of dimethyl sulfoxide could increase the adsorption capacity of the modified pineapple fiber. Optimum pH values for Cu2+, Cd2+, and Pb2+ removal by MPPF-DM70 were pH 5.5, 7.5, and 5.5, respectively. The Cu2+, Cd2+, and Pb2+ adsorptions by MPPF-DM70 followed the pseudo second-order kinetics model and Langmuir model.

  17. Inhaled multiwalled carbon nanotubes modulate the immune response of trimellitic anhydride-induced chemical respiratory allergy in brown Norway rats.

    PubMed

    Staal, Yvonne C M; van Triel, Jos J; Maarschalkerweerd, Thérèse V P; Arts, Josje H E; Duistermaat, Evert; Muijser, Hans; van de Sandt, Johannes J M; Kuper, C Frieke

    2014-10-01

    The interaction between exposure to nanomaterials and existing inflammatory conditions has not been fully established. Multiwalled carbon nanotubes (MWCNT; Nanocyl NC 7000 CAS no. 7782-42-5; count median diameter in atmosphere 61 ± 5 nm) were tested by inhalation in high Immunoglobulin E (IgE)-responding Brown Norway (BN) rats with trimellitic anhydride (TMA)-induced respiratory allergy. The rats were exposed 2 days/week over a 3.5-week period to a low (11 mg/m(3)) or a high (22 mg/m(3)) concentration of MWCNT. Nonallergic animals exposed to MWCNT and unexposed allergic and nonallergic rats served as controls. At the end of the exposure period, the allergic animals were rechallenged with TMA. Histopathological examination of the respiratory tract showed agglomerated/aggregated MWCNT in the lungs and in the lung-draining lymph nodes. Frustrated phagocytosis was observed as incomplete uptake of MWCNT by the alveolar macrophages and clustering of cells around MWCNT. Large MWCNT agglomerates/aggregates were found in granulomas in the allergic rats, suggesting decreased macrophage clearance in allergic rats. In allergic rats, MWCNT exposure decreased serum IgE levels and the number of lymphocytes in bronchoalveolar lavage. In conclusion, MWCNT did not aggravate the acute allergic reaction but modulated the allergy-associated immune response.

  18. Preparation, characterization and luminescent properties of dense nano-silica hybrids loaded with 1,8-naphthalic anhydride.

    PubMed

    Wang, Jinpeng; Sun, Jihong; Li, Yuzhen; Wang, Feng

    2014-03-01

    Novel luminescent dense nano-silica hybrid materials (DNSS) modified with different amounts of (3-aminopropyl)triethoxysilane (APTES) and 1,8-naphthalic anhydride (NA) were successfully synthesized via two steps combined with post-grafting methods. Powder X-ray diffraction (XRD), N2-sorption analysis, Fourier transform infrared (FT-IR) spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), photoluminescence (PL) spectroscopy and elemental analysis, as well as time-resolved decays were employed to characterize the resultant hybrid materials. The results revealed that luminescent organic molecules had been successfully loaded onto the amine-modified surface of nano-silica spheres. In addition, their fluorescence intensity and characteristic peak of emission spectra changed with increasing amount of APTES and NA additive. In particular, the characteristic peak showed a red shift from 390 to 450 nm, however, this was inconsistent with results calculated on the basis of the elemental analysis data, most probably because of the dispersion behaviors of NA molecules from the aggregating to the monolayer state. These observations demonstrated the existence of a quantum confinement effectiveness of NA-DNSS samples, and therefore a possible mechanism was put forward.

  19. Intranasal Administration of Maleic Anhydride-Modified Human Serum Albumin for Pre-Exposure Prophylaxis of Respiratory Syncytial Virus Infection

    PubMed Central

    Sun, Zhiwu; Wang, Qian; Jia, Ran; Xia, Shuai; Li, Yuan; Liu, Qi; Xu, Wei; Xu, Jin; Du, Lanying; Lu, Lu; Jiang, Shibo

    2015-01-01

    Respiratory syncytial virus (RSV) is the leading cause of pediatric viral respiratory tract infections. Neither vaccine nor effective antiviral therapy is available to prevent and treat RSV infection. Palivizumab, a humanized monoclonal antibody, is the only product approved to prevent serious RSV infection, but its high cost is prohibitive in low-income countries. Here, we aimed to identify an effective, safe, and affordable antiviral agent for pre-exposure prophylaxis (PrEP) of RSV infection in children at high risk. We found that maleic anhydride (ML)-modified human serum albumin (HSA), designated ML-HSA, exhibited potent antiviral activity against RSV and that the percentages of the modified lysines and arginies in ML- are correlated with such anti-RSV activity. ML-HSA inhibited RSV entry and replication by interacting with viral G protein and blocking RSV attachment to the target cells, while ML-HAS neither bound to F protein, nor inhibited F protein-mediated membrane fusion. Intranasal administration of ML-HSA before RSV infection resulted in significant decrease of the viral titers in the lungs of mice. ML-HSA shows promise for further development into an effective, safe, affordable, and easy-to-use intranasal regimen for pre-exposure prophylaxis of RSV infection in children at high risk in both low- and high-income countries. PMID:25690799

  20. Slow digestion property of octenyl succinic anhydride modified waxy maize starch in the presence of tea polyphenols.

    PubMed

    Peng, Shanli; Xue, Lei; Leng, Xue; Yang, Ruobing; Zhang, Genyi; Hamaker, Bruce R

    2015-03-18

    The in vivo slow digestion property of octenyl succinic anhydride modified waxy corn starch (OSA-starch) in the presence of tea polyphenols (TPLs) was studied. Using a mouse model, the experimental results showed an extended and moderate postprandial glycemic response with a delayed and significantly decreased blood glucose peak of OSA-starch after cocooking with TPLs (5% starch weight base). Further studies revealed an increased hydrodynamic radius of OSA-starch molecules indicating an interaction between OSA-starch and TPLs. Additionally, decreased gelatinization temperature and enthalpy and reduced viscosity and emulsifiability of OSA-starch support their possible complexation to form a spherical OSA-starch-TPLs (OSAT) complex. The moderate and extended postprandial glycemic response is likely caused by decreased activity of mucosal α-glucosidase, which is noncompetitively inhibited by tea catechins released from the complex during digestion. Meanwhile, a significant decrease of malondialdehyde (MDA) and increased DPPH free radical scavenging activity in small intestine tissue demonstrated the antioxidative functional property of the OSAT complex. Thus, the complex of OSAT, acting as a functional carbohydrate material, not only leads to a flattened and prolonged glycemic response but also reduces the oxidative stress, which might be beneficial to health.