Synthesis and styrene copolymerization of novel ring-substituted tert-butyl phenylcyanoacrylates

Abstract

Novel ring-substituted tert-butyl phenylcyanoacrylates, RPhCH=C(CN)CO2C(CH3)3, where R is 2-chloro-6-fluoro, 3-chloro-2-fluoro, 3-chloro-4-fluoro, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2,4,6-trimethyl, 2,3-dimethyl-4-methoxy, 3,5-dimethoxy-4-hydroxy, were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and tret-butyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the acrylates were copolymerized with styrene in solution with radical initiation at 70C. The compositions of the copolymers were calculated from nitrogen analysis.