Development of Polymer Emulsion Utilizing Radical Ring-Opening Polymerization

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This work dealt with synthesis of novel polymer emulsion utilizing radical ring-opening polymerization. We examined the synthesis and radical polymerization of vinylcyclopropanes having cyclic thioacetal, amide, ester, trimethylsilyl groups. The monomer with cyclic thioacetal moiety showed low polymerizability, while the monomers with amide and ester groups underwent radical polymerization efficiently to afford the polymers consisting of 1,5-ring-opened units quantitatively. A bifunctional vinylcyclopropane afforded a crosslinked polymer. A trimethylsilylated polymer was reacted with electrophiles to afford the corresponding adducts. We examined the radical emulsion polymerization of vinylcyclopropanes, 1,1-bis(ethoxycar-bonyl)-2-vinylcyclopropane (ECVCP) and 1,1-dichloro-2-vinylcyclopropane (CVCP). ECVCP underwent soap-free and soap-in emulsion polymerization satisfactorily to afford the ring-opened polymer in good yields. Polymer emulsions were obtained in a spherical shape with single particle size distribution. Meanwhile, emulsion polymerization of CVCP proceeded in only a low conversion.