A New Enone-Containing Triglyceride Derivative as Precursor of Thermosets from Renewable Resources

被引:39
作者
de Espinosa, L. Montero [1 ]
Ronda, J. C. [1 ]
Galia, M. [1 ]
Cadiz, V. [1 ]
机构
[1] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, Tarragona 43007, Spain
关键词
aza-Michael; biopolymers; crosslinking; curing of polymers; renewable resources; triglycerides;
D O I
10.1002/pola.22992
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A novel triglyceride containing alpha,beta-unsaturated ketone was prepared through photoperoxidation from high oleic sunflower oil by two steps one pot environmentally friendly procedure. This new enone-containing triglyceride was crosslinked with diaminodiphenylmethane (DDM) via aza-Michael addition. A kinetic study of the reaction of p-toluidine with either enone-containing methyl oleate or epoxidized methyl oleate, as model compounds, allowed us to establish the higher reactivity of the former, thus confirming this curing system as an alternative to amine-cured epoxidized vegetable oils. The thermal properties of thermosets from enone- and epoxy-containing triglycerides with DDM have been evaluated. (c) 2008 Wiley Periodicals, Inc.
引用
收藏
页码:6843 / 6850
页数:8
相关论文
共 33 条
[1]   Development of amine-acid cured Annona squamosa oil epoxy anticorrosive polymeric coatings [J].
Ahmad, S ;
Naqvi, F ;
Sharmin, E ;
Verma, KL .
PROGRESS IN ORGANIC COATINGS, 2006, 55 (03) :268-275
[2]  
Biermann U, 2000, ANGEW CHEM INT EDIT, V39, P2206, DOI 10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO
[3]  
2-P
[4]  
Bozell J. J., 2006, ACS S SERIES, V921
[5]   Synthesis and characterization of monomers and polymers for adhesives from methyl oleate [J].
Bunker, SP ;
Wool, RP .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2002, 40 (04) :451-458
[6]  
Corley LS, 1990, U.S. Patent, Patent No. [4962179, US 4.962.179]
[7]   Amine-cured ω-epoxy fatty acid triglycerides:: Fundamental structure-property relationships [J].
Earls, Jim D. ;
White, Jerry E. ;
Lopez, Leonardo C. ;
Lysenko, Zenon ;
Dettloff, Marvin L. ;
Null, Marty J. .
POLYMER, 2007, 48 (03) :712-719
[8]   Photolytic and free-radical polymerization of cinnamate esters of epoxidized plant oil triglycerides [J].
Esen, H ;
Küsefoglu, SH .
JOURNAL OF APPLIED POLYMER SCIENCE, 2003, 89 (14) :3882-3888
[9]   REACTION OF SINGLET OXYGEN WITH OLEFINS - QUESTION OF MECHANISM [J].
FRIMER, AA .
CHEMICAL REVIEWS, 1979, 79 (05) :359-387
[10]   Christopher Foote's discovery of the role of singlet oxygen [1O2 (1Δg)] in photosensitized oxidation reactions [J].
Greer, Alexander .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (11) :797-804