Synthesis and Free Radical Copolymerization of a Vinyl Monomer from Soybean Oil

Abstract

A one-step method that converts soybean oil into (acryloylamino)­ethyl soyate, a new vinyl monomer of free radical polymerization, was developed. The synthesized monomer combines a vinyl double bond (acryloyl functional group) and nonconjugated (isolated) double bonds of fatty acids. The double bond of the acryloyl group is reactive in a free radical chain polymerization that yields linear macromolecules containing isolated double bonds in side chains. Monomer reactivity ratios (<i>r</i>₁, <i>r</i>₂) in copolymerization of the new soybean oil-based acrylic monomer (SBA) with styrene, methyl methacrylate, and vinyl acetate, as well as the <i>Q</i>–<i>e</i> parameters of the SBA, were determined. The obtained results indicate that copolymerization can be described with the classical Mayo–Lewis equation. In terms of polymerizability, the SBA can be classified as an acrylic monomer. The double bonds of the fatty acid chains remain mainly unaffected during the free radical polymerization. The remaining unsaturated fragments in the side chains make the resulting macromolecules capable of further oxidative cross-linking and the development of cross-linked polymer coatings