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

Novel halogen ring-trisubstituted 2-methoxyethyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2CH2OCH3 (where R is 5-chloro-2,3-dimetoxy, 3-bromo-4,5-dimethoxy, 5-bromo-2,3-dimethoxy, 2-bromo-3-hydroxy-4-methoxy, 4-bromo-2,6-difluoro, 3-chloro-2,6-difluoro, 4-chloro-2,6-difluoro, 2-hydroxy-3,5-diiodo, 2,3,6-trichloro, 2,3,4-trifluoro, 2,4,6-trifluoro) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-trisubstituted 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.