Methyl-b-cyclodextrin, amphiphilic oligosaccharide, was used to improve the polymerizability of monomers from high oleic soybean and linseed oil in emulsion copolymerization with styrene. Using X-ray diffractometry and differential scanning calorimetry, interactions between the monomers and methyl-b-cyclodextrin were confirmed, while the formation of 1:1 complex from oligosaccharide and each monomer molecules was demonstrated by mass spectrometry. In the presence of “host-guest” complexes, polymer yield increases as the coagulum amount drops during the emulsion polymerization of both plant oil-based monomers with styrene indicating their enhanced aqueous solubility. Remarkably, latex polymers with a consistently higher molecular weight were obtained in the presence of methyl-b-cyclodextrin. The complex formation and incorporation of monomer molecules into the oligosaccharide cavities protect the fatty acid moieties and diminishes chain transfer. This was quantitatively confirmed in 1H NMR spectroscopy by determining the number of protons of the alkyl carbon−carbon double bonds and the bisallylic hydrogen atoms in the unsaturated fatty acid moieties of the latex copolymers. The observed effect is more pronounced for more unsaturated monomer from linseed oil. Based on the obtained results, methyl-b-cyclodextrin plays a twin function role in both enhancing POBM polymerizability as well as protecting against allylic termination chain transfer.

Twin function of methyl-b-cyclodextrin in emulsion polymerization of monomers from plant oils

2019 Spring National Meeting

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