Copper catalyzed ring opening copolymerization of a vinyl cyclopropane and methyl methacrylate

Abstract

Vinyl cyclopropanes are an important class of monomers which on radical ring opening polymerization (RROP) lead to polymers having cyclic moieties, carbon-carbon unsaturation and different other functional groups inside its backbone as in the pendant group. This investigation reports controlled radical ring opening polymerization (CRROP) of 1,1-bis (ethoxy carbonyl)-2-vinylcyclopropane (BCVCP) catalyzed by Cu catalyst. In this case homo and co-polymerization of BCVCP was carried out via ATRP using ethyl-2-bromoisobutyrate as initiator and CuBr as catalyst in combination with Me₆-TREN ligand. Radical polymerization of BCVCP and its copolymerization with methyl methacrylate (MMA) via ATRP led to predominantly 1,5 ring opening polymerization leading to linear polymers with >CC< in the main chain of the polymer. Conventional free radical co-polymerization of BCVCP and MMA led to polymers predominantly with cyclic rings in the main chain. The polymers were characterized by NMR, FT-IR, GPC, DSC and TGA analysis.