Synthesis and styrene copolymerization of novel methyl and oxy ring-disubstituted tert-butyl phenylcyanoacrylates

Abstract

Novel ring-disubstituted tert-butyl phenylcyanoacrylates, RPhCH=C(CN)CO2C(CH3)3, where R is 2,5-dimethyl, 3,4-dimethyl, 2,3-dimethoxy, 2,5-dimethoxy, 3,5-dimethoxy, 4-methoxy-2-methyl, 4-methoxy-3-methyl, 3-ethoxy-4-methoxy, 3-ethoxy-4-hydroxy, 3-ethoxy-2-hydroxy, 3-benzyloxy-4-methoxy, 4-benzyloxy-3-methoxy, 2,3-(methylenedioxy) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and tret-butyl 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.