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Unveiling the reactivity of epoxides in carbonated epoxidized soybean oil and application in the stepwise synthesis of hybrid poly(hydroxyurethane) thermosets
| dc.rights.license | embargo | en_US |
| hal.structure.identifier | Saint-Gobain Recherche [SGR] | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 2 LCPO : Biopolymers & Bio-sourced Polymers | |
| dc.contributor.author | HELBLING, Peroline | |
| hal.structure.identifier | Saint-Gobain Recherche [SGR] | |
| dc.contributor.author | HERMANT, F. | |
| hal.structure.identifier | Saint-Gobain Recherche [SGR] | |
| dc.contributor.author | PETIT, M. | |
| hal.structure.identifier | Laboratoire de l'intégration, du matériau au système [IMS] | |
| hal.structure.identifier | Institut des Sciences Moléculaires [ISM] | |
| dc.contributor.author | TASSAING, Thierry | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 2 LCPO : Biopolymers & Bio-sourced Polymers | |
| dc.contributor.author | VIDIL, Thomas
IDREF: 187905878 | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 2 LCPO : Biopolymers & Bio-sourced Polymers | |
| hal.structure.identifier | Fédération de recherche INCREASE [INCREASE] | |
| dc.contributor.author | CRAMAIL, Henri | |
| dc.date.accessioned | 2023-01-14T20:47:18Z | |
| dc.date.available | 2023-01-14T20:47:18Z | |
| dc.date.issued | 2023-01-01 | |
| dc.identifier.issn | 1759-9954 | en_US |
| dc.identifier.uri | oai:crossref.org:10.1039/d2py01318e | |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/171666 | |
| dc.description.abstractEn | In this work, the crosslinking reaction of partially carbonated epoxidized soybean oils with different diamines was investigated. To this end, a series of carbonated soybean oils (CSBO), with a carbonation ratio ranging from 45% (CSBO45) to 98% (CSBO98) were synthesized by CO2 carbonation of epoxidized soybean oil (ESBO). The relative aminolysis rate of the carbonate and epoxide functions of CSBO45, and also of the esters of the triglyceride skeleton, was monitored through an unprecedented combination of in situ infrared and Raman spectroscopy at various temperatures T (60 °C ≤ T ≤ 150 °C). Interestingly, two regimes are identified: (i) for T < 100 °C, a PHU regime, during which all the carbonate functions of CSBO45 react to provide an uncrosslinked PHU prepolymer (viscous liquid), (ii) for T ≥ 100 °C, a hybrid regime, during which the epoxide functions react to provide a hybrid thermosetting polymer (elastic solid). For the first time, we report the “conversion vs. time” plots for the aminolysis of epoxide in ESBO and partially carbonated ESBO. They indicate that the initiation of the reaction is thermally delayed as compared to the aminolysis of the corresponding carbonates. Surprisingly, the sol–gel transition of CSBO45 is correlated to the initiation of epoxide aminolysis, a counterintuitive conclusion given that ESBO cannot be crosslinked by a diamine under the same conditions. These results suggest that the combination of reactive carbonates with sluggish epoxides results in a decrease of undesirable side reactions such as ester aminolysis and intramolecular cyclization. Finally, general guidelines can be recommended for the stepwise synthesis of triglyceride-based hybrid poly(hydroxyurethane) thermosets. | |
| dc.language.iso | EN | en_US |
| dc.rights | Attribution-NonCommercial-ShareAlike 3.0 United States | * |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-sa/3.0/us/ | * |
| dc.source | crossref | |
| dc.subject.en | Poly(hydroxyurethane) (PHU) | |
| dc.subject.en | Carbonated soybean oil (CSBO) | |
| dc.subject.en | Biosourced resin | |
| dc.title.en | Unveiling the reactivity of epoxides in carbonated epoxidized soybean oil and application in the stepwise synthesis of hybrid poly(hydroxyurethane) thermosets | |
| dc.type | Article de revue | en_US |
| dc.identifier.doi | 10.1039/d2py01318e | en_US |
| dc.subject.hal | Chimie/Polymères | en_US |
| bordeaux.journal | Polymer Chemistry | en_US |
| bordeaux.page | DOI: D2PY01318E | en_US |
| bordeaux.volume | 14 | en_US |
| bordeaux.hal.laboratories | Laboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629 | en_US |
| bordeaux.hal.laboratories | Institut des Sciences Moléculaires (ISM) - UMR 5255 | en_US |
| bordeaux.institution | Université de Bordeaux | en_US |
| bordeaux.institution | Bordeaux INP | en_US |
| bordeaux.institution | CNRS | en_US |
| bordeaux.peerReviewed | oui | en_US |
| bordeaux.inpress | non | en_US |
| bordeaux.import.source | dissemin | |
| hal.identifier | hal-03939411 | |
| hal.version | 1 | |
| hal.date.transferred | 2023-01-14T20:47:37Z | |
| hal.export | true | |
| workflow.import.source | dissemin | |
| dc.rights.cc | CC BY-NC-SA | en_US |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Polymer%20Chemistry&rft.date=2023-01-01&rft.volume=14&rft.spage=DOI:%20D2PY01318E&rft.epage=DOI:%20D2PY01318E&rft.eissn=1759-9954&rft.issn=1759-9954&rft.au=HELBLING,%20Peroline&HERMANT,%20F.&PETIT,%20M.&TASSAING,%20Thierry&VIDIL,%20Thomas&rft.genre=article |
