Multi-functionalization of gallic acid. Synthesis of a novel bio-based epoxy resin

被引：240

作者：

Aouf, Chahinez ^{[1
,2
,3
]}

Nouailhas, Helene ^{[4
]}

Fache, Maxence ^{[5
]}

Caillol, Sylvain ^{[5
]}

Boutevin, Bernard ^{[5
]}

Fulcrand, Helene ^{[1
,2
,3
]}

机构：

[1] INRA, UMR1083 Sci Oenol, F-34060 Montpellier, France

[2] Montpellier SupAgro, UMR1083 Sci Oenol, F-34060 Montpellier, France

[3] Univ Montpellier I, UMR1083 Sci Oenol, F-34060 Montpellier, France

[4] Innobat, Cap Alpha, F-34830 Clapiers, France

[5] ENSCM, Equipe Ingn & Architectures Macromolr, Inst Charles Gerhardt, UMR CNRS 5253, F-05 Montpellier 05, France

来源：

EUROPEAN POLYMER JOURNAL | 2013年 / 49卷 / 06期

关键词：

Polyphenols; Renewable resources; Thermosetting polymers; Epoxy resins; BISPHENOL-A; ENGINEERING PLASTICS; THERMAL-PROPERTIES; EPOXIDATION; LIGNIN; KETONES; EPICHLOROHYDRIN; DEGRADATION; COPOLYMER; RISK;

D O I：

10.1016/j.eurpolymj.2012.11.025

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Novel biobased epoxy thermoset was synthesized from gallic acid, a phenolic acid encountered in various plants, both in its simple form and as a part of gallotannins. The functionalization of gallic acid was carried out using a two-step synthesis involving the allylation of OH groups followed by the epoxidation of resulting double bonds. The performance of two oxygen transfer agents (meta-chloroperbenzoic acid (mCPBA) and methyl(trifluoromethyl) dioxirane generated in situ from 1,1,1-trifluoroacetone and oxone) was evaluated in the epoxidation of the allylic double bonds. The glycidyl derivative of gallic acid (GEGA) obtained from mCPBA epoxidation was cured in epoxy polymer formulation with isophorone diamine (IPDA). The thermal and mechanical preliminary analyses showed that this new epoxy network based on GEGA displayed interesting properties compared to the epoxy polymer formulated with commercial diglycidyl ether of bisphenol A (DGEBA). A higher glass-transition temperature of GEGA/IPDA epoxy resin indicates a higher crosslinking density of this network. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1185 / 1195

页数：11

共 36 条

[1] DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].