Vinyl oil monomers. I. Vicinal methacryloxy‐hydroxy soy oils

New vinyl oil monomers have been prepared by combining epoxidized unsaturated oils with vinyl carboxylic acids. This is accomplished by heating the reactants in the presence of free radical inhibitors and appropriate reaction catalysts. The reaction consists of cleavage of the oxirane ring followed by addition of the vinyl acid through its carboxylic group. By varying the reactants and the conditions of reaction, a large family of related, but different, vinyl oil monomers can be prepared. Vicinal methacryloxy‐hydroxy soy oil monomers are clear, yellow, medium viscosity (2000–2500 cpoise), high molecular weight (1300–1500) liquids. Chemical analyses are presented for typical preparations. The monomers readily homopolymerize by a free radical mechanism to clear, solid, thermoset resins. They are compatible with a variety of commercial vinyl monomers and form copolymers which range from highly viscous liquids through soft gels, to tough rubbery products and hard resins. Data are presented on physical properties of copolymer castings of several specific vicinal methacryloxy‐hydroxy soy oil monomers.