Synthesis and styrene copolymerization of novel phenoxy ring-substituted isopropyl phenylcyanoacrylates

Abstract

Phenoxy ring-substituted isopropyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH(CH3)2, where R is 2-(3-methoxyphenoxy), 2-(4-methoxyphenoxy), 3-(4-methoxyphenoxy), 3-(4-methylphenoxy), 4-(4-bromophenoxy), 4-(4-fluorophenoxy), 2-(4-chlorophenoxy), 3-(4-chlorophenoxy), 4-(3-chlorophenoxy), 4-(4-chlorophenoxy), 3-(3,4-dichlorophenoxy), 3-(3,5-dichlorophenoxy), 4-(2,4-dichlorophenoxy) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of phenoxy ring-substituted benzaldehydes and isopropyl 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 and the structures were analyzed by IR, 1H and 13C-NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 129-500ºC range with residue (2-10% wt.), which then decomposed in the 500-800ºC range.