Synthesis and Characterization of a Soybean Oil- Based Macromonomer

David Delatte, University of Southern Mississippi
Ethem Kaya, University of Southern Mississippi
James W. Rawlins, University of Southern Mississippi
Shelby F. Thames, University of Southern Mississippi


An acrylate-functional soybean oil-based macromonomer (SoyAA-1) was synthesized in high yields utilizing sequential amidation and acrylation processes to serve as an internal plasticizer in emulsion polymers. The structure and structure-property relationships of this unique macromonomer were validated with FTIR, NMR, and LC-MS. The viability of SoyAA-1 as a comonomer in emulsion polymerization was established via copolymerization with methyl methacrylate (MMA) at varying copolymer weight compositions. The effect of increasing SoyAA-1 levels and concomitantly higher allylic functionality was measured through film coalescence, minimum film forming temperature, and initial and progressively increasing glass transition temperature(s). The results indicate that synthetic modification of a renewable resource, soybean oil, can yield a valuable monomer that can be copolymerized in high yields via emulsion polymerization to produce practical and mechanically stable latexes for a variety of coatings applications. (c) 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40249.