GB789034A - Homopolymers and copolymers of unsaturated esters of epoxy fatty acids - Google Patents

Abstract

Unsaturated aliphatic esters of epoxy-fatty acids are prepared by treating the corresponding esters of unsaturated fatty acids with peracetic acid at between 10 DEG and 90 DEG C. In examples, wherein the unsaturated fatty acid ester is reacted with per-acetic acid in acetone and the resulting mixture is then stripped of volatiles by being added dropwise to ethylbenzene refluxing under reduced pressure, (1) and (2) allyl or vinyl 9,10-epoxystearate is obtained from allyl or vinyl oleate; (3) allyl esters of mixed epoxy acids are obtained from the allyl esters of a mixture of oleic, linolenic, linoleic, palmitic, myristic and stearic acids or (4) from allyl esters of a mixture of oleic, linoleic and linolenic acids; (5) allyl 9,10-epoxystearate is obtained from allyl elaidate; (6) allyl 10,11-epoxyundecanoate is obtained from allyl 10-undecylenate, the epoxy ester then being converted into 3-cyclohexenylmethyl epoxy-undecanoate by alcoholysis using sodium methylate as catalyst; and (7) allyl or vinyl 9,10,12,13-diepoxystearate is obtained from allyl linoleate. Reference is also made to the allyl and vinyl esters of 5,6-epoxy laurate and of various epoxidized vegetable oil and tall oil fatty acids. Allyl esters of unsaturated fatty acids used as starting materials in the examples are prepared by reacting the unsaturated acid with the alcohol in the presence of sulphuric acid as catalyst and removing water as it is formed by azeotropic distillation with toluene. Linoleic acid is obtained from safflower oil fatty acids by dissolving the acids in hot methanolic urea, cooling the solution to -9 DEG C., filtering, then stripping the filtrate of methanol and adding water and separating the resulting fatty acid layer.ALSO:Polymers are prepared by polymerizing in the presence of a polymerization catalyst an epoxy organic ester having the formula <FORM:0789034/IV (a)/1> where X is an epoxyalkyl group containing from 8 to 16 carbon atoms and 1 or 2 epoxy oxygen atoms, and R is a mono-olefinic aliphatic group having alpha-beta or beta-gamma unsaturation, either alone or in the presence of an organic polymerizable material. Specified epoxy esters are allyl or vinyl 5,6-epoxylaurate, allyl 10,11-epoxyundecanoate, vinyl or allyl 9,10-epoxymyristate, stearate or palmitate, vinyl 9, 10, 12, 13-diepoxystearate, the alkyl and vinyl esters of epoxidized soybean oil-, linseed oil-, safflower oil-, cottonseed oil- and tall oilfatty acids and their mixtures. Specified copolymerizable materials are vinyl or vinylidene chloride, bromide or fluoride, acrylonitrile, methacrylonitrile, methyl or ethyl methacrylate or ethyl acrylate, vinyl formate, acetate, chloroacetate, butyrate or caproate, butadiene, isoprene, dimethyl butadiene, chloroprene, 1-acetoxybutadiene, piperylene, 2-cyano- or fluoro- or methoxy-butadiene, acetylene, alkyl and dialkyl acetylenes, the divinyl, dialkyl and dimethallyl esters of oxalic, maleic, malonic, citric, tartaric, phthalic, isophthalic and terephthalic acids, styrene, chlorostyrene and allylstyrene, or mixtures thereof, or a glycidyl polyether of a polyhydric phenol. Specified catalysts are acetyl, benzoyl, and lauroyl peroxides and potassium persulphate. The polymerization may take place in solution, emulsion, suspension or bulk.