Biobased Thermosetting Epoxy: Present and Future

被引：928
作者：
Auvergne, Remi [1 ]
Caillol, Sylvain [1 ]
David, Ghislain [1 ]
Boutevin, Bernard [1 ]
Pascault, Jean-Pierre [2 ,3 ]
机构：
[1] Ecole Natl Super Chim Montpellier, Inst Charles Gerhardt, CNRS, Lab Ingn & Architecture Macromol,UMR 5253, F-34296 Montpellier 05, France
[2] INSA Lyon, IMP, UMR5223, F-69621 Villeurbanne, France
[3] Univ Lyon, F-69622 Lyon, France
来源：
CHEMICAL REVIEWS | 2014年 / 114卷 / 02期
关键词：
CARBOXYLIC ACID-DERIVATIVES; LOW-TEMPERATURE RELAXATIONS; EPOXIDIZED NATURAL-RUBBER; INDUCED PHASE-SEPARATION; STRAW LIGNIN POLYMER; BISPHENOL-A; RENEWABLE RESOURCES; THERMAL-PROPERTIES; CURING AGENTS; SOYBEAN OIL;
D O I：
10.1021/cr3001274
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The works undertaken to obtain either partially or fully biobased epoxide materials are studied. The reaction between the phenate ion and ECH 2 reveals two competitive mechanisms, one-step nucleophilic substitution with cleavage of the C-Cl bond and a two-step mechanism based on ring opening of ECH (2) with ArO- (1') followed by intramolecular cyclization (SNi) of the corresponding alcoholate, containing one atom of chlorine in the β-position, formed in situ. Depending on the substituent position or nature in the phenol, it takes 6-20 h at reflux or 24-26 h at room temperature to complete the reaction. The reaction of ECH with an alcohol is more difficult, with many side reactions, since this reaction generates new alcohol groups with similar pKa values which are able to react with the epoxy group of ECH, thus leading to its homopolymerization. Epoxies are able to react with (meth)acrylic acid to give formulations for coating applications or vinyl ester monomers and networks after radical polymerization.
引用
收藏
页码：1082 / 1115
页数：34
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