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Unexpected Synthesis of Segmented Poly(hydroxyurea–urethane)s from Dicyclic Carbonates and Diamines by Organocatalysis

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorBOSSION, Amaury
hal.structure.identifierDepartamento de Ciencia y Tecnologıa de Polımeros e Instituto de Materiales Polimericos [POLYMAT]
dc.contributor.authorAGUIRRESAROBE, Roberto
hal.structure.identifierDepartamento de Ciencia y Tecnologıa de Polımeros e Instituto de Materiales Polimericos [POLYMAT]
dc.contributor.authorIRUSTA, Lourdes
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorTATON, Daniel
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorCRAMAIL, Henri
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.identifierDepartamento de Ciencia y Tecnologıa de Polımeros e Instituto de Materiales Polimericos [POLYMAT]
dc.contributor.authorMECERREYES, David
hal.structure.identifierUniversity of Chinese Academy of Sciences [Beijing] [UCAS]
dc.contributor.authorSU, Cui
dc.contributor.authorLIU, Guoming
hal.structure.identifierDepartamento de Ciencia y Tecnologıa de Polımeros e Instituto de Materiales Polimericos [POLYMAT]
dc.contributor.authorMÜLLER, Alejandro
hal.structure.identifierDepartamento de Ciencia y Tecnologıa de Polımeros e Instituto de Materiales Polimericos [POLYMAT]
dc.contributor.authorSARDON, Haritz
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2018
dc.identifier.issn0024-9297
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/19804
dc.description.abstractEnA complete study of the effect of different organocatalysts on the step-growth polyaddition of a five-membered dicyclic carbonate, namely diglycerol dicarbonate, with a poly(ethylene glycol)-based diamine in bulk at 120 °C was first carried out. The reaction was found to be dramatically catalyst-dependent, higher rates being observed in the presence of strong bases, such as phosphazenes (t-Bu-P4 or P4) and 5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Unexpectedly, the as-formed urethane linkages entirely vanished with time, as evidenced by FTIR and 13C NMR spectroscopies, while signals due to urea bond formation progressively appeared. An advantage of the chemical transformation occurring from urethane to urea linkages was further taken by optimizing the polymerization conditions to access a range of poly(hydroxyurea–urethane)s (PHUUs) with precise urethane to urea ratio in a one-pot process. Characterization of the corresponding polymers by rheological measurements showed that the storage modulus reached a plateau at high temperatures and at high urea contents. The application temperature range of poly(hydroxyurea–urethane)s could thus be increased from 30 to 140 °C, as for regular polyurethanes. Furthermore, SAXS and phase-contrast microscopy images demonstrated that increasing the urea content improved the phase separation between soft and hard segments of these PHUUs. Altogether, this novel, straightforward, efficient, and environmentally friendly strategy enables the access to non-isocyanate poly(urea–urethane)s with tunable urethane-to-urea ratio from five-membered dicyclic carbonates following an organocatalytic pathway.
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.title.enUnexpected Synthesis of Segmented Poly(hydroxyurea–urethane)s from Dicyclic Carbonates and Diamines by Organocatalysis
dc.typeArticle de revue
dc.identifier.doi10.1021/acs.macromol.8b00731
dc.subject.halChimie/Polymères
bordeaux.journalMacromolecules
bordeaux.page5556-5566
bordeaux.volume51
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue15
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-01917939
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01917939v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Macromolecules&rft.date=2018&rft.volume=51&rft.issue=15&rft.spage=5556-5566&rft.epage=5556-5566&rft.eissn=0024-9297&rft.issn=0024-9297&rft.au=BOSSION,%20Amaury&AGUIRRESAROBE,%20Roberto&IRUSTA,%20Lourdes&TATON,%20Daniel&CRAMAIL,%20Henri&rft.genre=article


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