Derivatives of linseed oil and camelina oil as monomers for emulsion polymerization

Abstract

Acrylated methyl esters of higher fatty acids derived from camelina oil and linseed oil were synthesized through transesterification, epoxidation, and subsequent acrylation. Methyl methacrylate and butyl acrylate were copolymerized with various amounts of bio-based derivatives (5 - 30 wt% in monomer mixture) to obtain polymeric latexes for coating applications. Successful emulsion polymerizations with up to 25 wt% of the bio-based derivatives were performed with low coagulum (below 2%) and high monomer conversion (around 95%). The incorporation of bio-based derivatives into polymeric latexes was confirmed with infrared spectroscopy. Asymmetric flow field flow fractionation coupled with a multi-angle light scattering was used to analyze the synthesized copolymers in terms of their molar mass distribution. The results revealed that copolymerizing the bio-based derivatives resulted in ultra-high molar mass nanogel fractions formed because of multi-acrylated ingredients derived from polyunsaturated fatty acids. The phenomenon of nanogel formation became more pronounced for the linseed oil-based derivative. Evaluated coating properties showed that latexes comprising the bio-based derivatives provided increased water repellence (about 10 degrees higher water contact angles were achieved for all bio-based coating compositions in contrast to a reference latex). Moreover, latexes comprising chemically modified oils in the content of 25 and 30 wt% provided water whitening-resistant coatings, making the bio-based derivatives promising candidates for replacing petroleum-based monomers in the production of sustainable latex coatings.