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I Preparation and Properties of Bio-Based Polyurethane Made from Natural Rubber and Poly(Ε-Caprolactone)

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I Preparation and Properties of Bio-Based Polyurethane Made from Natural Rubber and Poly(Ε-Caprolactone) i Preparation and Properties of Bio-based Polyurethane Made from Natural Rubber and Poly(-caprolactone) Wannarat Panwiriyarat A Thesis Submitted in Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Polymer Science and Technology Prince of Songkla University, Thailand and Le Grade de Docteur de l’Université du Maine (Spécialité: Chimie et Physicochimie des Polymères) Faculté des Sciences et Techniques, Université du Maine, France 2013 Copyright of Prince of Songkla University ii Thesis Title Preparation and Properties of Bio-based Polyurethane Made from Natural Rubber and Poly(-caprolactone) Author Miss Wannarat Panwiriyarat Major Program Polymer Science and Technology Major Advisor : Examining Committee : …………………………………………… ..…........……….……………Chairperson (Assoc. Prof. Dr. Varaporn Tanrattanakul) (Prof. Dr. Fabrice Burel) …………………………………………… ..….....……….………………Committee (Prof. Dr. Jean-François Pilard) (Assoc. Prof. Dr. Varaporn Tanrattanakul) Co-advisor …………………………………………… ..….....……….………………Committee (Dr. Pamela Pasetto) (Prof. Dr. Jean-François Pilard) …………………………………………… ..….....……….………………Committee (Dr. Chuanpit Khaokong) (Dr. Pamela Pasetto) ..….....……….………………Committee (Dr. Chuanpit Khaokong) ..….....……….………………Committee (Dr. Anuwat Saetung) The Graduate School, Prince of Songkla University, Thailand and Faculté des Sciences et Techniques, Université du Maine, Le Mans, France have approved this thesis as fulfillment of the requirements for the Degree of Doctor of Philosophy (Polymer Science and Technology) and the Doctor degree of Université du Maine (Chimie et Physicochimie des Polymères). ……….……………………...………… (Assoc. Prof. Dr. Teerapol Srichana) Dean of Graduate School iii This is to certify that the work here submitted is the result of the candidate’s own investigations. Due acknowledgement has been made of any assistance received. ..……...………………………….Signature (Assoc. Prof. Dr. Varaporn Tanrattanakul) Major Advisor ..……...………………………….Signature (Miss Wannarat Panwiriyarat) Candidate iv I hereby certify that this work has not already been accepted in substance for any degree, and is not being concurrently submitted in candidature for any degree. ……...………………………….Signature (Miss Wannarat Panwiriyarat) Candidate v Thesis Title Preparation and Properties of Bio-based Polyurethane Made from Natural Rubber and Poly(-caprolactone) Author Miss Wannarat Panwiriyarat Major Program Polymer Science and Technology Academic Year 2012 ABSTRACT The aim of this research work was to prepare a novel bio-based polyurethane (PU) composed by chemically modified natural rubber (NR) and poly(-caprolactone) diol (PCL), with and without isocyanate. Hydroxyl telechelic natural rubber (HTNR) was synthesized via epoxidized and carbonyl telechelic natural rubber. The parameters studied included type and relative amount of diisocyanate, molar ratio between diisocyante and diol (NCO:OH), molecular weight of HTNR and PCL diol, 1,4-butane diol (BDO, chain extender) content and molar ratio between HTNR:PCL diols. Three types of diisocyanate were employed: isophorone diisocyanate (IPDI), toluene-2,4-diisocyanate (TDI) and hexamethylene diisocyanate (HDI). The number average molecular weights of HTNR and PCL diol were selected: 1700, 2800 and 2900 g/mol for HTNR and 530 and 2000 g/mol for PCL diol. The NCO:OH molar ratio was in the range 0.75:1.00 – 2.85:1.00. PU was prepared by one-shot method. The chemical structure of HTNR, PCL and PU were identified by 1H-NMR, FTIR and Raman spectroscopy. Tensile properties and tear resistance of PU were investigated. Characterization of mechanical and thermal properties was carried out using DSC, DMTA and TGA. A preliminary study showed that the molecular weight of PU increased with increasing NCO:OH molar ratio and reaction time, and chloroform was not a good solvent for polymer casting. Tetrahydrofuran was an appropriate solvent as it allowed film formation and it was used in all the other experiments. The NCO:OH molar ratio of 1.25:1.00 was suitable for preparing good PU films. FTIR analysis verified the presence of urethane linkages and crosslinking or chain branching. PU demonstrated excellent mechanical properties, which depended on the chemical composition. Excluding the use of PCL2000 and HDI, the tensile behavior seemed to vi have typical elastomeric characteristics. PU became amorphous except in the case of HDI, which was able to crystallize leading to the crystalline PU. The crystallinity increased the Young’s modulus, the tear strength, the hardness and the thermal stability of PU. PU showed a phase separation between the PCL and HTNR segments. The longer and more flexible chain and non-polarity of HTNR were responsible of a decrease of the mechanical properties and transition temperatures. The very high molar ratio of NCO:OH (2.85:1.00) changed the tensile characteristics from an elastomer to a plastic. The high crosslinking was attributed to there being no phase separation between the hard and the soft segment. Hydrogen bonding between the PCL diol and the hard segment produced a high Tg. Raman spectra were able to identify the urethane linkage of PU containing different diisocyanates by showing the relative absorbance peaks. Synthesis of PU without isocyanate was successfully obtained via a polyaddition polymerization between a cyclic carbonate telechelic PCL/NR and 1,4-butylenediamine. The cyclic carbonate telechelic NR and cyclic carbonate telechelic PCL were prepared via the modification of the hydroxyl end groups of HTNR and PCL diols to carboxylic acid end groups by reacting with succinic anhydride. Then, the carboxylic acid end groups were changed to the cyclic carbonate end groups by using glycerol carbonate. Keyword: Bio-based polymers, bioplastics, natural rubber, polyurethane, poly(- caprolactone), renewable resources vii Titre de la thèse Synthèse et étude des propriétés d’un polyuréthane biosourcé obtenu du caoutchouc naturel et du poly(-caprolactone) Auteur Wannarat Panwiriyarat Spécialisation Science et technologie des polymères Année Académique 2012 RESUME L’objectif de ce travail de thèse était la synthèse d’un nouveau matériau polyuréthane biorsourcé composé par du caoutchouc naturel modifié chimiquement et par du poly(-caprolactone), (PCL), en présence ou absence d’isocyanates. Des oligoisoprènes téléchéliques hydroxylés (HTNR) ont été obtenus après époxidation du caoutchouc naturel et réduction des oligomères carbonyles. Plusieurs paramètres ont été étudiés comme la nature et la quantité relative de diisocyanate, le rapport molaire entre diisocyanate et diol (NCO:OH), l’influence de la masse molaire des diols HTNR et PCL, le pourcentage de 1,4-butane diol (BDO, extenseur de chaîne), et le rapport molaire entre les diols HTNR:PCL. Trois types de diisocyanate ont été employés : isophorone diisocyanate (IPDI), toluène-2,4-diisocyanate (TDI) et hexaméthylène diisocyanate (HDI). Masses molaires différentes ont été utilisées pour les diols HTNR et PCL: 1700, 2800 et 2900 g/mol pour HTNR et 530 et 2000 g/mol pour PCL. Le rapport molaire entre NCO:OH était entre 0,75:1,00 – 2,85:1,00. Les PU ont été préparés par la méthode « one shot » et les structures chimiques des HTNR et PU ont été identifiées par 1H-NMR et FTIR. La résistance à la traction et à la rupture ont été étudiées. La caractérisation a été conduite par DSC, DMTA, ATG et spectroscopie Raman. Une étude préliminaire a montré que la masse molaire du PU augmentait avec le rapport NCO:OH et le temps de réaction, et que le chloroforme n’était pas un bon solvant pour obtenir des films. Le tetrahydrofurane était le solvant le plus approprié et il a été utilisé par la suite pour toutes les polymérisations. Le rapport NCO:OH = 1,25:1,00 s’est révélé optimal pour obtenir des films. L’analyse FTIR a permis de vérifier la présence de liaisons uréthane, de points de réticulation et de branchements. Le polyuréthane a montré des propriétés mécaniques excellentes viii dépendantes de la composition chimique. Si on exclue l’utilisation de PCL2000 et de HDI, le comportement à la traction était caractéristique des élastomères. Les PU étaient amorphes sauf lorsque le HDI a été employé. Duos ce cos été obtenais un PU semi cristallin. Cette cristallinité augmente le module de Young, la résistance à la rupture, la dureté et la stabilité thermique du PU. Pour ce PU ont observé une séparation de phase entre les segments du PCL et du HTNR. Les chaînes plus longues et plus flexibles du HTNR et leur non polarité sont responsables de la diminution des propriétés mécaniques et des températures de transition. Le materiae pane d’un comportement élastomère a un comportement plastique pour un rapport NCO:OH élevé (2,85 :1,00). Le dégréé de réticulation élevé a été retenu comme la cause pour laquelle il n’y avait pas de séparation de phase entre les segments souples et durs. La liaison hydrogène entre le diol PCL et le segment hard a généré des Tg élevées. Les spectres Raman ont montré la formation de la liaison uréthane du PU contenant différents diisocyanates. La synthèse de PU sans diisocyanate a été obtenue grâce à une réaction de polyaddition entre des carbonates cycliques téléchéliques dérivés du PCL et du caoutchouc naturel, et la 1,4-butylène diamine. Les structures contenant des carbonates cycliques ont été obtenues grâce à la modification des groupes OH sur le HTNR et le PCL à groupes carboxyle, utilisant l’anhydride succinique, et a la réaction successive avec le glycérol carbonate. Mots clés: polymères biosourcés, bioplastiques, caoutchouc
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