Synthesis and styrene copolymerization of novel methyl, methoxy, chloro, and fluorophenoxy ring-substituted 2-methoxyethyl phenylcyanoacrylates

Novel phenoxy ring-substituted 2-methoxyethyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2CH2OCH3 (where R is 3-phenoxy, 3-(4-chlorophenoxy), 4-(4-chlorophenoxy), 2-(4-fluorophenoxy), 4-(4-fluorophenoxy), 2-(3-methoxyphenoxy), 2-(4-methoxyphenoxy), 3-(4-methoxyphenoxy), 4-(4-methoxyphenoxy), 3-(4-methylphenoxy), 4-(4-methylphenoxy), 3-(3,5-dichlorophenoxy), 4-(2,4-dichlorophenoxy), 3-(3-trifluoromethyl)phenoxy) 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 ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The compositions of the copolymers were calculated from nitrogen analysis.