Synthesis and styrene copolymerization of halogen ring-disubstituted 2-methoxyethyl phenylcyanoacrylates

Abstract

Novel halogen ring-disubstituted 2-methoxyethyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2CH2OCH3 (where R is 2,5-dibromo, 3,5-dibromo, 2,3-dichloro, 2,4-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2-chloro-6-fluoro, 3-chloro-4-fluoro, 2-chloro-5-nitro, 4-chloro-3-nitro, 2-fluoro-5-iodo) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and 2-methoxyethyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the acrylates were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The compositions of the copolymers were calculated from nitrogen analysis.