Synthesis and styrene copolymerization of benzyloxy, methylphenyl, acetoxy, acetyl, cyano, and amino ring-substituted 2-methoxyethyl phenylcyanoacrylates

Novel ring-substituted 2-methoxyethyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2CH2OCH3 (where R is 2-benzyloxy, 3-benzyloxy, 4-benzyloxy, 3-(4-methylphenyl), 4-(4-methylphenyl), 4-acetoxy, 2-acetyl, 3-acetyl, 4-acetamido, 2-cyano, 3-cyano, 4-cyano, 4-dimethylamino, 4-diethylamino) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted 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.