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Development of New Polyesters by Organometallic and Enzymatic Catalysis Thibaud Debuissy

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Development of New Polyesters by Organometallic and Enzymatic Catalysis Thibaud Debuissy Development of new polyesters by organometallic and enzymatic catalysis Thibaud Debuissy To cite this version: Thibaud Debuissy. Development of new polyesters by organometallic and enzymatic catalysis. Poly- mers. Université de Strasbourg, 2017. English. NNT : 2017STRAE003. tel-01610732 HAL Id: tel-01610732 https://tel.archives-ouvertes.fr/tel-01610732 Submitted on 5 Oct 2017 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. UNIVERSITÉ DE STRASBOURG ÉCOLE DOCTORALE Physique – Chimie Physique ICPEES - UMR 7515 THÈSE présentée par : Thibaud DEBUISSY Soutenue le : 10 mai 2017 pour obtenir le grade de : Docteur de l’U niversité de Strasbourg Discipline/ Spécialité : Chimie des Polymères Développement de nouveaux polyesters par catalyse organométallique et enzymatique THÈSE dirigée par : M. AVEROUS Luc Professeur, Université de Strasbourg RAPPORTEURS : M. CRAMAIL Henryi Professeur, Université de Bordeaux M. FLEURY Etienne Professeur, INSA Lyon AUTRES MEMBRES DU JURY : Mme DELAITE Christelle Professeur, Université de Haute-Alsace MEMBRE INVITE : M. POLLET Eric Maître de Conférences, Université de Strasbourg ICPEES, Institut de Chimie et Procédés pour l’Energie, l’Environnement et la Santé – UMR 7515 25 rue Becquerel – 67087 Strasbourg Cedex 2 Communications liées aux travaux de thèse II Communications liées aux travaux de thèse COMMUNICATIONS LIÉES AUX TRAVAUX DE THÈSE III Communications liées aux travaux de thèse IV Communications liées aux travaux de thèse Publications Les résultats présentés dans cette thèse font l’objet de 10 articles et d’une revue bibliographique. Articles publiés : · Debuissy T., Pollet E., Avérous L. – “Synthesis of potentially biobased copolyesters based on adipic acid and butanediols: kinetic study between 1,4- and 2,3-butanediol and their influence on crystallization and thermal properties”, Polymer, 2016, 99, 204-213. · Debuissy T., Pollet E., Avérous L. – “Enzymatic synthesis of a biobased copolye ster from poly(butylene succinate) and poly[( R)-3-hydroxybutyrate]: Study of reaction parameters on the transesterification rate”, Biomacromolecules, 2016, 17 (12), 4054 –4063. · Debuissy T., Pollet E., Avérous L. – “Synthesis and characterization of biobased poly(butylene succinate- ran -butylene adipate). Analysis of the composition-dependent physicochemical properties”, European Polymer Journal, 2017, 87, 84-98. · Perez-Camargo R. A., Fernandez-d'Arlas B., Cavallo D., Debuissy T., Pollet E., Avérous, L., Muller A. J. – “Tailoring the Structure, Morphology, and Crystallization of Isodimorphic Poly(butylene succinate-ran -butylene adipate) Random Copolymers by Changing Composition and Thermal History”, Macromolecules, 2017, 50 (2), 597 –608. · Debuissy T., Pollet E., Avérous L. – “Titanium -catalyzed transesterification as a route to the synthesis of fully biobased poly(3-hydroxybutyurate- co -butylene dicarboxylate) copolyesters, from their homopolyesters”, European Polymer Journal, 2017, 90, 92-104. · Debuissy T., Pollet E., Avérous L., –“Synthesis and characterization of block poly(ester-ether- urethane)s from bacterial poly(3-hydroxybutyrate) oligomers .”, Journal of Polymer Science Part A: Polymer Chemistry, 2017, 55 (11), 1949-1961. · Debuissy T., Pollet E., Avérous L., –“Enzymatic synthesis of biobased poly(1,4-butylene succinate- ran -2,3-butylene succinate) copolyesters and characterization. Influence of 1,4- and 2,3-butanediol contents ”, European Polymer Journal, 2017, 93, 103-115. · Debuissy T., Sangwan P., Pollet E., Avérous L., –“Study on the structure-properties relationship of biodegradable and biobased aliphatic copolyesters based on 1,3-propanediol, 1,4-butanediol, succinic and adipic acids ”, Polymer, 2017, 122, 105-116. · Debuissy T., Pollet E., Avérous L. –“Synthesis and characterization of fully biobased poly(propylene succinate- ran -propylene adipate). Analysis of the architecture-dependent physicochemical behavior ”, Journal of Polymer Science Part A: Polymer Chemistry, 2017, DOI:10.1002/pola.28668. Articles soumis : · Debuissy T., Pollet E., Avérous L., –“Enzymatic synthesis of potentially biobased and biodegradable aliphatic copolyesters: effect of the monomer length on the lipase reactivity and copolyester properties. ” Soumis dans European Polymer Journal . Articles qui seront soumis ultérieurement : · Debuissy T., Pollet E., Avérous L., –“Abiotic and biotic synthesis of biobased polyesters from short building blocks – A review ”. V Communications liées aux travaux de thèse Conférences Les résultats présentés dans cette thèse ont fait l’objet d’une communication orale dans une conférence internationale : · Debuissy T., Pollet E., Avérous L. –“New fully biobased macromolecular architectures: analysis of the structure-properties relationship of synthesized terpolyesters from building blocks ”, communication orale , 23 rd Bio-Environmental Polymer Society, Karlsruhe (Allemagne, 14 octobre 2015). VI Liste des abréviations LISTE DES ABRÉVIATIONS VII Liste des abréviations VIII Liste des abréviations [α] Specific optical rotation 1,10-DCO 1,10-decanediol 1,3-PDO 1,3-propanediol 1,4-BDO 1,4-butanediol 1,6-HDO 1,6-hexanediol 2,3-BDO 2,3-butanediol 4,4’ -MDI 4,4’ -diphenylmethylene diisocyanate AA Adipic acid (ou acide adipique) As Aspartate CALB Candida antarctica lipase B (ou lipase B de Candida antarctica ) CDCl 3 Deuterated chloroform CES Chromatographie d’exclusion stérique Cl-TMDP 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane COOH Carboxylic acid end-group DBE Dibenzyl ether DBTL Dibutyl tin (II) dilaurate DEA Diethyl adipate (ou diéthyle adipate) DEPT Distortionless enhancement by polarization transfer DES Diethyl succinate (ou diéthyle succinate) DMA Dimethyl adipate (ou diméthyle adipate) DMAP 4-dimethylaminopyridine DMS Dimethyl succinate (ou diméthyle succinate) DMSO-d 6 Deuterated dimethyl sulfoxide DPE Diphenyl ether DP n Number-average degree of polymerization DSC Differential scanning calorimetry Dt Degree of biodegradability DTG Derivative thermogravimetric analysis Ɖ Dispersity Ea Energy of activation EDIPA N-ethyl- N,N-diisopropylamine EG Ethylene glycol eq. Molar equivalent (ou equivalent molaire) FTIR Fourrier transform infra-red Glu Glutamate HCl Hydrogen chloride HDI 1,6-hexamethylene diisocyanate HiC Humicola insolens cutinase His Histidine HSQC-NMR Heteronuclear single quantum coherence nuclear magnetic resonance IUPAC International Union of Pure and Applied Chemistry log P Logarithm of the partition coefficient between 1-octanol and water LXX Average sequence length of XX units MALDI-ToF MS Matrix-assisted laser desorption-ionization – time of flight - mass spectrometry mcl Medium-chain-length MHS Mark-Houwink-Sakurada Mn Number-average molar mass (ou masse molaire moyenne en nombre) mol.% Mol percent Mw Weight-average molar mass (ou masse molaire moyenne en poids) N435 Novozym ® 435 NMR Nuclear magnetic resonance OH Hydroxyl end-group p Extent of reaction P(3HB- co -3HHx) Poly(3-hydroxybutyrate- co -3-hydroxyhexanoate) P(3HB- co -3HV) Poly(3-hydroxybutyrate- co -3-hydroxyvalerate) P(3HB- co -4HB) Poly(3-hydroxybutyrate- co -4-hydroxybutyrate) PB’A Poly(2,3-butylene adipate) PB’S Poly(2,3-butylene succinate) PBA Poly(1,4-butylene adipate) IX Liste des abréviations PBAT Poly(butylene adipate-co-butylene terephthalate) PBAT Poly(butylene adipate- co -butylene terephthalate) PBB’A Poly(1,4-butylene adipate- co -2,3-butylene adipate) PBB’S Poly(1,4-butylene succinate- co -2,3-butylene succinate) PBS Poly(1,4-butyene succinate) PBSA Poly(1,4-butylene succinate- co -1,4-butylene adipate) PCL Poly( ε-caprolactone) pds.% Pourcentage en masse PEEU Poly(ester-ether-urethane) (ou poly(ester-éther-uréthane)) PEF Poly(ethylene furanoate) PEG Poly(ethylene glycol) PET Poly(ethylene terephthalate) Pether Polyether-diol PHA Poly(hydroxyalkanoate) (ou poly(hydroxyalcanoate)) PHB Poly[( R)-3-hydrobutyrate] PHB-diol Telechelic hydroxylated poly(3-hydrobutyrate) oligomers PLA Poly(lactic acid) PLA Poly(lactic acid) Poly(HB- co -BA) Poly(3-hydroxybutyrate-co-butylene adipate) Poly(HB- co -BS) Poly(3-hydroxybutyrate-co-butylene succinate) PPA Poly(1,3-propylène adipate) PPBA Poly(1,3-propylene adipate- co -1,4-butylene adipate) PPBS Poly(1,3-propylene succinate- co -1,4-butylene succinate) PPG-PEG-PPG Poly(propylene glycol)- block -poly(ethylene glycol)- block -poly(propylene glycol) PPS Poly(1,3-propylene succinate) PPSA Poly(1,3-propylene succinate- co -1,3-propylene adipate) R Degree of randomness RMN Résonance magnétique nucléaire ROP Ring-opening polymerization rpm Round per minute SA Succinic acid (ou acide succinique) sc Supercirtical fluids scl Short-chain-length SEC Size exclusion chromatography Ser Serine SnCl 2 Tin (II) chloride SSP Solid-state polymerization Tb Boiling temperature Tc Crystallization temperature Tcc Cold-crystallization temperature Td,2% 2 wt.% degradation temperature Td,50% 50 wt.% degradation temperature Tdeg,max Maximal degradation rate temperature TEA Triéthylamine Tébu Température d’ébulittion Tf Température de fusion Tg Glass transition temperature TGA
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