Constance W. Gould

Copolymerization of methyl esters of unsaturated C18 fatty acids

In order to assay the possibilities of making high polymers from linseed oil, the copolymerizations of styrene with the methyl esters of oleic, linoleic, linolenic, and conjugated linolenic acids were studied at 60–130C and copolymerizations of the last three esters with acrylonitrile were studied at 60C. Appropriate free radical initiators were employed in all cases. The esters without conjugated unsaturation show little tendency to enter a copolymer with styrene, but copolymers containing up to 40% by weight of conjugated linoleate can be obtained. Linoleic, linolenic, and conjugated linoleic esters copolymerize readily with acrylonitrile. Products containing up to 45 mole %, 80 wt %, of the conjugated ester can be made. However, methyl eleostearate, with three conjugated double bonds, inhibits the polymerization of both styrene and acrylonitrile. Quantitative comparisons of the behaviors of the esters are made through the copolymerization equation. The probable performance of these and other vinyl monomers in copolymerization with linseed oil is discussed.

Copolymerizations of esters and glycerides of unsaturated C18 fatty acids with ethyl acrylate and acrylonitrile

This work was undertaken to assay the possibilities of making useful copolymers from linseed and similar oils. Methyl esters of linoleic, conjugated linoleic, linolenic, and alkali-cyclized linolenic acid have been copolymerized with ethyl acrylate at 60C and monomer reactivity ratios have been determined. In comparison with benzene or methyl stearate as inert diluents, all of these esters and several glycerides with conjugated or unconjugated unsaturation, and also 3,5,7-decatriene as a model compound, retard the polymerization of ethyl acrylate. Methyl eleostearate and the decatriene are unusually strong retarders of polymerizations of styrene, acrylonitrile, and ethyl acrylate, increasing retardation in the order given. Several experiments on copolymerizations of acrylonitrile with linseed oil at 60–130C show that the copolymerizations which incorporate much oil in the copolymer are slow but that the isolated copolymers have good drying and film-forming properties.