1. Novel aliphatic polyesters from an oleic acid based monomer. Synthesis, epoxidation, cross-linking and biodegradation
- Author
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Fabrice Laflèche, Yann Raoul, Nathalie Jarroux, Philippe Guégan, Sylvain Claude, Pierre-Jean Roumanet, Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (LAMBE), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ONIDOL, Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (LAMBE - UMR 8587), Centre National de la Recherche Scientifique (CNRS)-Université Paris-Saclay-Université d'Évry-Val-d'Essonne (UEVE)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Organisation Nationale Interprofessionnelle des Graines et Fruits Oléagineux (ONIDOL), Unité de Nutrition Humaine - Clermont Auvergne (UNH), Institut National de la Recherche Agronomique (INRA)-Université Clermont Auvergne (UCA), Institut Parisien de Chimie Moléculaire (IPCM), Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), and Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Renewable resources ,Condensation polymer ,Materials science ,Polymers and Plastics ,[SDV]Life Sciences [q-bio] ,Diol ,General Physics and Astronomy ,Epoxide ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,chemistry.chemical_compound ,Polymer chemistry ,Materials Chemistry ,Organic chemistry ,Poly(ester) ,chemistry.chemical_classification ,Organic Chemistry ,Fatty acids derivatives ,Polymer ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Polyester ,Oleic acid ,Monomer ,chemistry ,Polymerization ,[PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph] ,0210 nano-technology - Abstract
The synthesis of polymeric materials based on monomers from renewable feedstocks is a steadily growing field. New aliphatic polyesters derived from the 1,18-(Z)-octadec-9-enedioic acid (D18:1), a high oleic sunflower oil fatty acid derivative, and aliphatic diols of different molecular weight (from 1,3-propanediol to 1,12-dodecanediol) have been synthesized and characterized. The polymerization was undertaken by direct bulk polycondensation of a diacid with a diol, with or without a metal catalyst, leading to viscous liquid to solid semi-crystalline polyesters at room temperature, depending on the diol type. The molecular weights of polyesters ranged between 7000 and 20,000 g mol −1 . The main attractive aspects of these polyesters are the renewable biomass origin of the diacid and the presence of double bonds on the polymer backbone (oleic acid derivative) allowing subsequent chemical modifications. The epoxidation of these double bonds was undertaken on the macromolecular chains to induce the photochemical cross-linking of the epoxide functions. Transparent and homogeneous cross-linked films were made by photo-polymerization of the epoxy units with less than 5% of extractible products. Enzymatic degradation of these polyesters (cross-linked) was poor over 8 weeks.
- Published
- 2013
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