Saint-Étienne-de-Chigny, France
Saint-Étienne-de-Chigny, France

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Annunziata L.,CNRS Chemistry Institute of Rennes | Fouquay S.,BOSTIK S.A. | Michaud G.,BOSTIK CRD | Simon F.,BOSTIK CRD | And 2 more authors.
Polymer Chemistry | Year: 2013

The ring-opening metathesis polymerization (ROMP) of cyclooctene (COE) has been achieved with Grubbs 2nd generation ruthenium catalyst in the presence of vinyl or acryloyl derivatives of glycerol carbonate. Such asymmetric chain-transfer agents enabled the synthesis in high yields of α-cyclocarbonate,ω-vinyl-poly(cyclooctene) (PCOE) and, more rewardingly, of the highly valuable α,ω-dicyclocarbonate telechelic PCOE. © 2013 The Royal Society of Chemistry.

Cornille A.,Charles Gerhardt Institute | Serres J.,Charles Gerhardt Institute | Michaud G.,BOSTIK CRD | Simon F.,BOSTIK CRD | And 3 more authors.
European Polymer Journal | Year: 2016

Polyepoxyurethane polymers were synthesized from PolyHydroxyUrethane (PHU) prepolymers terminated amine and epoxy multifunctional. In order to ensure this, PHU prepolymers was synthesized from the reaction between α, ω-bis-cyclic-carbonates (poly(propylene)oxide bis-carbonates) and different excess of diamines (ethylenediamine) to terminate these prepolymers by amine with differents chain length. Then, these aminotelechelic PHU oligomers were re-used in formulation with multifunctional epoxy compound (Bisphenol A Diglycidyl Ether, Di-epoxydized Cardanol or Phloroglucinol Tris Epoxy) to synthesize polyepoxyurethane polymers called also hybrid polymers. Firstly, the raw materials were analyzed in order to determine proportion stoichiometry for carbonate/amine and of hybrid materials formulations. Secondly, for the purpose to demonstrate that the reaction carbonate/amine form hydroxyurethane compound, a model study was realized. Then, syntheses and analyzes of prepolymers terminated amine by 1H, 13C NMR, TGA and DSC was conducted. Once these oligomers analyzed, the hybrid polymers were formulated from epoxy compounds at different temperatures to determine the best cross-linking proceed. Epoxyurethane polymers were characterized by ATG, DSC and measurement of their swelling index and gel content. These materials exhibited glass transition temperature between -5°C and 42°C and a thermal stability above 320°C at 30% of weight loss. © 2015 Elsevier Ltd. All rights reserved.

Cornille A.,Charles Gerhardt Institute | Michaud G.,BOSTIK CRD | Simon F.,BOSTIK CRD | Fouquay S.,BOSTIK S.A. 16 32 | And 3 more authors.
European Polymer Journal | Year: 2016

A series of poly(hydroxyurethane) (PHU) materials were synthesized by step growth polymerization of cyclic carbonates and diamines. Trimethylolpropane tris-carbonate and various poly(propylene oxide) bis-carbonates were copolymerized with EDR-148 or 1,3-cyclohexanebis(methylamine) (CBMA). Thermal, mechanical and thermo-mechanical properties of PHU materials were characterized by DSC, TGA, durometer, dynamometer and DMA. Moreover, for the first time, we report adhesive properties of PHU synthesized without isocyanate on wood, aluminum and glass supports. All these properties were compared to reference polyurethane materials, synthesized from poly(propylene oxide) triol polymerized with hexamethylenediisocyante (HDI) or 1,3-bis(isocyanatomethyl)cyclohexane (CBMI), in order to compare the materials properties of similar chemical structure. PHUs exhibit outstanding adhesion properties due to the presence of hydroxyl groups hanging off the main polycarbonate chain. © 2016 Elsevier Ltd

Annunziata L.,CNRS Chemistry Institute of Rennes | Diallo A.K.,CNRS Chemistry Institute of Rennes | Fouquay S.,BOSTIK S.A. | Michaud G.,BOSTIK CRD | And 4 more authors.
Green Chemistry | Year: 2014

α,ω-Di(glycerol carbonate) telechelic poly(propylene glycol) (PPG), poly(ethylene glycol) (PEG), poly(ester ether) (PEE), and poly(butadiene) (PBD) have been synthesized through chemical modification of the corresponding α,ω-dihydroxy telechelic polymers (PPG-OH2, PEG-OH 2, PEE-OH2 and PBD-OH2, respectively). Tosylation of the polymer diols with 4-tosylmethyl-1,3-dioxolan-2-one (GC-OTs) afforded, in high yields, the desired PPG, PEG, PEE and PBD end-capped at both termini with a five-membered ring cyclic glycerol carbonate (4-hydroxymethyl-1, 3-dioxolan-2-one, GC). The GC-functionalization of the polymers at both chain-ends has been confirmed by NMR (1H, 13C, 1D and 2D) and FTIR spectroscopies. Using PPG-GC2 to demonstrate the concept, the corresponding polyhydroxyurethanes (PHUs/non-isocyanate polyurethanes (NIPUs)) have been subsequently prepared following a non-isocyanate method upon ring-opening catalyst-free polyaddition of the PPG-GC2 with JEFFAMINEs (Mn = 230-2000 g mol-1). The effect of various additives introduced during the polyaddition reaction has been studied at different temperatures. In particular, addition of LiBr (5 mol%) to the reaction medium was found to slightly promote the cyclocarbonate/amine reaction. The polymerization process was supported by FTIR and SEC analyses. © the Partner Organisations 2014.

Diallo A.K.,CNRS Chemistry Institute of Rennes | Annunziata L.,CNRS Chemistry Institute of Rennes | Fouquay S.,BOSTIK S.A | Michaud G.,BOSTIK CRD | And 4 more authors.
Polymer Chemistry | Year: 2014

The synthesis of a variety of mono- and di-(glycerol carbonate) telechelic polyolefins has been achieved upon ruthenium-catalyzed ring-opening metathesis polymerization (ROMP) of cyclooctene (COE) derivatives in the presence of a vinyl or acryloyl derivative of glycerol carbonate (GC) acting as a chain-transfer agent (CTA). Reaction monitoring based on SEC and 1H NMR analyses suggested that the ROMP proceeds through the formation of first the α-GC,ω-vinyl-poly(cyclooctene) (PCOE) intermediate, which eventually evolves over time into the α,ω-di(GC)-PCOE. The nature of the solvent was shown to have a significant impact on both the reaction rates and the eventual selectivity for the mono-/di-telechelic PCOE. ROMP of 3-alkyl (methyl, ethyl, n-hexyl)-substituted COEs (3-R-COEs) afforded only the α-GC,ω-vinyl-poly(3-R-COE)s, as a result of the steric hindrance around the active intermediate, while a 5-ethyl substituted COE (5-Et-COE) enabled access to the corresponding α,ω-di(GC)-poly(5-Et-COE). The ROMP of 5,6-epoxy-, 5-hydroxy- and 5-oxo-functionalized COEs in the presence of acryloyl-GC as the CTA has also been achieved, affording from the first two monomers polymers with GC end-groups at both extremities, while a 60 : 40 mixture of mono- and di-GC terminated P(5-OCOE) was observed in the latter case. © 2014 The Royal Society of Chemistry.

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