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Allyl esters of crambe‐derived long‐chain fatty acids and their polymers
Author(s) -
Chang ShuPei,
Miwa Thomas K.
Publication year - 1979
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1979.070240212
Subject(s) - polymerization , degree of unsaturation , chemistry , organic chemistry , erucic acid , behenic acid , polymer , polymer chemistry , allylic rearrangement , allyl alcohol , crystallinity , fatty acid , palmitic acid , catalysis , crystallography
Allyl esters of erucic, brassidic, behenic, oleo‐erucic, and stearo‐behenic acids, prepared by refluxing benzene solutions of the acids with excess allyl alcohol in the presence of p ‐toluenesulfonic acid monohydrate, polymerize smoothly in the presence of 5 wt. % t ‐butyl perbenzoate at 120°C for 24 hr. Polymerization of the unsaturated acid esters involves a large portion (ca. 84%) of allylic and a small portion (ca. 26%) of ethylenic bonds. The products, saturated and unsaturated, have a degree of polymerization between 6 and 10 and are soluble in typical polymer solvents. Crystallinity, judged by thermal analysis, decreased with increased cis unsaturation. The oligomers melted between −30°C and 59°C and started decomposing at 200°C.