New biobased epoxy hardeners: Thiol-ene addition on oligobutadiene

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• 作者：R&eacute ; mi Auvergne^a ; ^{remi.auvergne@enscm.fr} ; Myriam Desroches^a ; S&eacute ; bastien Clerc^a ; St&eacute ; phane Carlotti^b ; Sylvain Caillol^a ; Bernard Boutevin^a
• 关键词：Polymers functionalization ; Thiol-ene ; Polymeric amines ; Hardeners ; Epoxy resins
• 刊名：Reactive and Functional Polymers
• 出版年：2012
• 期刊代码：92_13815148
• 类别：ch
• 出版时间：June, 2012
• 卷：72
• 期：6
• 页码：393-401
• 文件大小：901 K

摘要

We report the synthesis and characterization of oligobutadienes functionalized with primary amine groups and theirs use as hardeners for epoxy resins. The functionalization of polybutadiene (with 59%of 1,2 double bonds) was carried out by the addition of 2-amino-3-mercaptopropanoic acid (cysteamine) in different ratios through thiol-ene coupling. The thiol-ene addition was performed in tetrahydrofurane solvent with 2,2鈥?azobis(2-methylpropionitrile) as radical initiator at 70 掳C. The ratio polymer/cysteamine was varied in order to obtain several number of amine functions per polymer chain and to compare the reactivity of thiol onto 1,2 and 1,4 double bonds of polybutadiene. The different characterizations of synthesized polymeric amines allowed us to identify the quantities of amine groups grafted onto 1,2 and 1,4 double bonds, the cyclization side reactions of 1,2 double bonds and the unreacted 1,2 and 1,4 double bonds. These polymeric amines were mixed with epoxy resins (BADGE) and led to materials with glass transition temperatures between 20 掳C and 60 掳C depending on the polymeric amines functionalities. The thermal properties of synthesized resins are similar to the ones measured on epoxy resins obtained with commercial hardeners (cycloaliphatic amine and 1,10-diaminodecane).