Radical ring-opening copolymerization behavior of vinyloxirane: Synthesis of copolymer from 2-isopropenyl-3-phenyloxirane and styrene and its functionalization

Abstract

The radical ring-opening copolymerization of 2-isopropenyl-3-phenyloxirane (1) with styrene (St) was examined to obtain the copolymer [copoly(1-St)] with a vinyl ether moiety in the main chain. The copolymers were obtained in moderate yields by copolymerization in various feed ratios of 1 and St over 120 °C; the number-average molecular weights (Mn) were estimated to be 1800–4200 by gel permeation chromatography analysis. The ratio of the vinyl ether and St units of copoly(1-St) was estimated with the 1H NMR spectra and varied from 1/7 to 1/14 according to the initial feed ratio of 1 and St. The haloalkoxylation of copoly(1-St) with ethylene glycol in the presence of N-chlorosuccinimide produced a new copolymer with alcohol groups and chlorine atoms in the side group in a high yield. The Mn value of the haloalkoxylated polymer was almost the same as that of the starting copoly(1-St). The incorporated halogen was determined by elemental analysis. The analytical result indicated that over 88% of the vinyl ether groups participated in the haloalkoxylation. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 3729–3735, 2000