Synthesis and styrene copolymerization of novel halogen ring-monosubstituted tert-butyl phenylcyanoacrylates

Novel ring-monosubstituted tert-butyl phenylcyanoacrylates, RPhCH=C(CN)CO2C(CH3)3 (where R is 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 3-iodo) 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.