Synthesis and copolymerization of novel oxy ring-substituted isopropyl cyanoarylacrylates

Novel oxy ring-substituted isopropyl 2-cyano-3-arylacrylates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 3-phenoxy, 4-phenoxy, 2-benzyloxy, 3-benzyloxy, 4-benzyloxy, 4-acetyloxy, 3-acetyl, 4-acetyl, 4-acetylamino, 4-methoxy-2-methyl, 4-methoxy-3-methyl, 3-ethoxy-4-methoxy, 3,4-dibenzyloxy, 3-benzyloxy-4-methoxy, 4-benzyloxy-3-methoxy, 2,3-dimethyl-4-methoxy, 2,5-dimethyl-4-methoxy, 2,4-dimethoxy-3-methyl, 2,4-dimethoxy-6-methyl, 3,5-dimethoxy-4-hydroxy) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of oxy ring-substituted benzaldehydes and isopropyl cyanoacetate and characterized by CHN elemental analysis, FTIR, 1H and 13C-NMR. All the acrylates were copolymerized with styrene in solution with radical initiation at 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by FTIR, 1H and 13C-NMR. Thermal properties of the copolymers are characterized by DSC and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500ºC range with a residue, which then decomposed in the 500-800ºC range.