Synthesis and styrene copolymerization of novel phenoxy and benzyloxy ring-substituted octyl phenylcyanoacrylates

Novel ring-substituted octyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2(CH2)6CH3 (where R is 3-phenoxy, 4-phenoxy, 4-(4-bromophenoxy), 3-(4-chlorophenoxy), 2-(4-fluorophenoxy), 3-(4-methylphenoxy), 4-(4-methylphenoxy), 4-(4-nitrophenoxy), 3-[3-(trifluoromethyl)phenoxy], 2-benzyloxy, 3-benzyloxy, 4-benzyloxy) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and octyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. 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.