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Functionalization of Polyisoprene: Toward the Mimic of Natural Rubber This Phd Work Focuses on a Better Comprehension of Natural Rubber (NR)

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Functionalization of Polyisoprene: Toward the Mimic of Natural Rubber This Phd Work Focuses on a Better Comprehension of Natural Rubber (NR) Functionalization of polyisoprene : toward the mimic of natural rubber Jeremie Grange To cite this version: Jeremie Grange. Functionalization of polyisoprene : toward the mimic of natural rubber. Polymers. Université de Bordeaux, 2018. English. NNT : 2018BORD0004. tel-01768472 HAL Id: tel-01768472 https://tel.archives-ouvertes.fr/tel-01768472 Submitted on 17 Apr 2018 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. THÈSE PRÉSENTÉE POUR OBTENIR LE GRADE DE DOCTEUR DE L’UNIVERSITÉ DE BORDEAUX ÉCOLE DOCTORALE DES SCIENCES CHIMIQUES SPÉCIALITÉ: Polymères Par Jérémie GRANGE Functionalization of Polyisoprene : Toward the mimic of Natural Rubber Fonctionnalisation de Polyisoprène : Vers un modèle du caoutchouc naturel Sous la direction de : Dr. Frédéric PERUCH et Pr. Stéphane GRELIER Co-encadrant : Dr. Rachid MATMOUR Soutenue le 23 janvier 2018 Membres du jury : Mme. PASETTO, Pamela Maître de conférences, Université du Maine Rapporteur M. CAILLOL, Sylvain Chargé de recherche CNRS, Université de Montpellier Rapporteur M. MATMOUR, Rachid Docteur, Michelin (MFPM) Examinateur M. BONFILS, Frédéric Chercheur, CIRAD Examinateur M. PERUCH, Frédéric Directeur de recherche CNRS, Université de Bordeaux Co-directeur M. GRELIER, Stéphane Professeur, Université de Bordeaux Co-directeur M. CARLOTTI, Stéphane Professeur, Bordeaux INP Président Pendant la rédaction de ce manuscrit, les titres suivants ont été écoutés: A Perfect Circle Chez Vous Flume Rose Le Père Never Be Like You Blue Charlie Foals Imagine L’Anticonformisme London Thunder Adham Shaikh Bon Iver Night Swimmers Water Prayer Holocene Albatross Air Skinny love Mountain At My Gates Alpha Beta Gaga Brigitte Inhaleur Sexy Boy Battez-vous Spanish Sahara Alanis Morissette Ma Benz’ Two Step Twice King Of Pain BRNS GoGo Penguin Alt-J Many Chances All Res Tessellate Interlude Hopopono Archive Slow Heart Branches Break Stay Tribal Bruce Springsteen Good Charlotte The False Foundation Streets of Philadelphia The Anthem Driving In Nails Bullet for My Valentine Lifestyles of the Rich & Famous Blue Faces All These Things I Hate Gorillaz Arctic Monkeys Tears Don’t Fall DARE Do I Wanna Know C2C Green Day R U Mine ? The Cell Americat Idiot Asaf Avidan Caspian Holiday Different Pulses La Cerva Boulevard Of Broken Asgeir Mie Dreams Head In The Snow Casius Hint Higher I <3 U SO Air To Sky Torrent Chez Damier Holy Other Going Home Can You Feel It Know Where Atreyu Chinese Man Hoobastank Right Side of the Bed Post Trauma Same Direction Bigflo&Oli Washington Square Just One Je suis CKY Hozier Dans mon lit Flesh Into Gear Arsonist’s Lullabye Répondez moi 96 Quite Bitter Beings In Veins Trop tard Dave Matthews Band Suicidal Children Alors alors You Might Die Trying Connected With Him Autre part Depeche Mode Never Seen Blink-182 Precious Blurry Road Bored To Death Die Antwoord Crashed Online Songs Baby’s On Fire No Name Sea The Rock Show Dub Inc Magnetic Tree Adam’s Song My Freestyle Jack’s Mannequin Feeling This Elliott Smith The Mixed Tape What’s my age again ? Between The Bars Jamie Cullum Blockhead Eminem Save Your Soul Insomniac Olympics Without Me Jeff Buckley Boards of Canada EZ3kiel Hallelujah Oscar See Through Red Dead In Valhalla Jidenna Eye Lux Long Live the Chief Peacock Tail Dusty Kasabian Chromakey Dreamcoat Born In Valhalla Man of Simple Pleasures Dayvan Cowboy Fakear Bumblebeee Bombay Bicycle Club Kids La Rue Kétanou Luna La Chaleur Des Corps La misère d’en face Bon Entendeur My Own Sun Ma faute à toi Une aventure Silver Les Hurlements d’Léo Ensemble Cheese Naan Salut à toi La Conscience Fauve Lostprophets La Nuit Vieux Frères Wake up L’Optimisme Voyous Burn, Burn M83 Paul Ritch SALM Intro Run Baby Run Rondo Parisiano Outro Phantogram Stupeflip Wait When I’m Small Understup Marilyn Manson Pierce The Veil Les Monstres Tainted Love Circles L.E.C.R.O.U Personal Jesus Prince La Religion du Stup Sweet Dreams Purple Rain The Antidote Miike Snow Rage Against The machine Stupeflip vite !!! Heart Is Full Bullet In The Head Sum 41 Minor Victories Guerilla Radio Underclass Hero Breaking My Light No Shelter No Reason A Hundred Ropes Know Your Enemy Hooch Give up the Ghost Bombtrack Noots Moderat Born of a Broken Man Thylacine Intruder Bulls on Parade Dad Mogwai Ratatat Poly Ether Cream on Chrome Piany Pianino Remurdered Loud Pipes Moskva The Precipice Rise Against Train Scotland’s Shame Behind Closed Doors Unkle Superheroes of BMX Injection When Things Explode Nina’school Prayer Of the Refugee No Where to Run Aïla Help Is On The Way Restless Tom Worth Dying For Wolves Of Manchester Punk Rock Star Satellite Psychotown Nu Savior 21h46 Before We Fall All That Sound Robin Foster Krocodil OrtoPilot Finis Terrae Her Meo Okkur 74 – ‘75 Sheriff of Lagatjar Zack Hemsey Pen Had Soothsayer PenInsular Remerciements Par où commencer ? Beaucoup, beaucoup de monde à remercier. Tout d’abord je tiens à remercier le LCPO de m’avoir accueilli et formé. A la longue, le laboratoire est devenu une sorte de seconde maison où il fait bon être, travailler et apprendre. Merci aux deux directeurs, Sébastien Lecommandoux et Henri Cramail de m’en avoir ouvert les portes. Biensûr, je remercie également à la fois les acteurs du projet Rubbex ainsi que l’entreprise Michelin pour tout ce qu’ils ont pu m’apporter tout au long de cette thèse comme connaissances, à la fois sur le caoutchouc naturel mais aussi sur la chimie des polymères en général et sur le milieu industriel. Ensuite vient le tour de mes chefs. Que dire ? Soit beaucoup, soit rien ! Je vais donc tâcher de faire preuve d’esprit de synthèse pour simplement vous dire merci pour tout ce que vous avez su m’apporter tant sur le plan scientifique que sur le plan humain. Je pense que vous en êtes conscients, mais vous êtes tous les deux de sacrés mentors pour moi et j’espère un jour être amené à retravailler avec vous quel que soit le projet, pour apprendre toujours plus à votre contact. Merci encore pour tout. Et puis il y a les collègues. Ceux qui m’ont vu (supporté) pendant ces 3 ans et plus. J’ai hésité à faire une liste, mais je pense que les concernés se reconnaitrons d’eux-mêmes et savent très bien à quel point ils comptent pour moi (#N1-04autenthique). Merci à vous tous pour les rencontres, les discussions, les fous rires, les débats, etc… Pour paraphraser deux artistes que j’aime beaucoup je dirais que « je suis un peu de moi, mais beaucoup de vous tous quand j’y pense ». Bonne route à tous et j’espère vous recroiser rapidement. Enfin, je voudrais remercier ma famille et mon Equipe de vie. Merci d’être là quel que soit l’instant. On en a traversé des choses ensemble…Vous étiez là tout au long de cette aventure de dingue, ces 3 ans de burn-out permanant et vous ne m’avez pas lâché ! Vous avez su me rebooster quand il fallait, m’aider à sortir la tête de l’eau par moment et me donner de la force et du courage quand j’en ai eu besoin. Merci pour ça, merci pour tout. #CROU Résumé en français Résumé en français Ce projet de recherche se propose de générer de nouvelles connaissances sur le caoutchouc naturel (NR) afin d’essayer de gérer au mieux cette ressource renouvelable. En particulier, il a été largement montré que le caoutchouc naturel est composé d’environ 93% de polyisoprène (PI) 1,4-cis de très forte masse molaire, mais également de 7% d’autres composés (lipides, protéines, minéraux, …). Ces derniers sont vraisemblablement responsables de la très grande différence de propriétés observée entre NR et caoutchouc synthétique. De plus, de nos jours, le seul modèle rendant compte de ces observations est le modèle décrit par Tanaka, à savoir que les chaines de PI sont fonctionnalisées en bout de chaine par des protéines et des lipides (Figure 1). Ce modèle qui propose donc que les chaines de PI soient plutôt sous la forme de copolymères est largement admis mais nécessite néanmoins d’être évalué afin de démontrer que la structure d’un tel copolymère peut rendre compte des propriétés supérieures du NR. L’objectif principal de ce projet de thèse est donc la synthèse de copolymères modèles et l’évaluation de leurs propriétés afin de mieux comprendre la structuration du NR lors du stockage et le durcissement généralement observé. La synthèse des macromolécules mimant le modèle de Tanaka peut être décomposée en plusieurs étapes : - L’obtention d’un noyau polyisoprène totalement « 1,4-cis » - Le greffage d’un phospholipide en ω de la chaîne PI - Le greffage d’une protéine en α de la chaîne PI Protéine Polyisoprène 1,4-cis Phospholipide Figure 1: Structure d’un polyisoprène bifonctionnel propose par Tanaka, pouvant modéliser la structure du NR. L’obtention d’un noyau polyisoprène (PI) totalement « 1,4-cis » peut s’envisager de différentes manières. La synthèse chimique a été largement étudiée. Plusieurs voies sont possibles (radicalaire, anioniques, métathèse, coordination, cationique) mais aucune ne permet à la fois un bon contrôle de la microstructure de la chaîne, des extrémités de chaîne et de la masse molaire. En revanche, des travaux sur la dégradation chimique (métathétique ou oxydative) montrent des résultats d’intérêt pour l’application recherchée dans notre travail.
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