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A thioglycerol route to bio-based bis-cyclic carbonates: poly(hydroxyurethane) preparation and post-functionalization

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorLAMARZELLE, Oceane
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorHIBERT, Geoffrey
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorGRAU, Etienne
IDREF: 187909261
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 3 LCPO : Polymer Self-Assembly & Life Sciences
dc.contributor.authorLECOMMANDOUX, Sebastien
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorCRAMAIL, Henri
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2017
dc.identifier.issn1759-9954
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/19793
dc.description.abstractEnThe present work is dedicated to the design of novel sulfur-substituted cyclic carbonates from thioglycerol, fatty acids and sugar derivatives. In this methodology, a sulfur atom is inserted in the β position of 5-membered ring cyclic carbonates via a two-step synthesis including the thiol–ene coupling of thioglycerol on fatty acid derivatives, followed by a transcarbonation. A similar strategy was adopted to prepare glycolipid-based cyclic carbonates in order to bring biodegradability to the final poly(hydroxyurethane)s. The so-formed monomers were characterized by NMR spectroscopies, HPLC and DSC. The enhanced reactivity of sulfur-substituted cyclic carbonates was demonstrated through a 1H NMR spectroscopy kinetic study of a model reaction with hexylamine. Fatty acid- and glycolipid-based sulfur-substituted bis-cyclic carbonates were then polymerized with diamines in a solvent using a catalyst-free process. FTIR, NMR, SEC, DSC and TGA were performed to investigate the PHUs’ chemical structure, molar masses and thermal properties. Finally, the so-formed PHUs were post-functionalized by sulfonation with m-CPBA taking advantage of thioether functions. The impact of the chemical modification was mostly studied on the polymer solubility and thermal stability.
dc.language.isoen
dc.publisherRoyal Society of Chemistry - RSC
dc.title.enA thioglycerol route to bio-based bis-cyclic carbonates: poly(hydroxyurethane) preparation and post-functionalization
dc.typeArticle de revue
dc.identifier.doi10.1039/c7py00556c
dc.subject.halChimie/Polymères
dc.subject.halChimie/Matériaux
dc.subject.halPhysique [physics]/Matière Condensée [cond-mat]/Science des matériaux [cond-mat.mtrl-sci]
bordeaux.journalPolymer Chemistry
bordeaux.page3438 - 3447
bordeaux.volume8
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue22
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-01611121
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01611121v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Polymer%20Chemistry&rft.date=2017&rft.volume=8&rft.issue=22&rft.spage=3438%20-%203447&rft.epage=3438%20-%203447&rft.eissn=1759-9954&rft.issn=1759-9954&rft.au=LAMARZELLE,%20Oceane&HIBERT,%20Geoffrey&GRAU,%20Etienne&LECOMMANDOUX,%20Sebastien&CRAMAIL,%20Henri&rft.genre=article


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