Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 11. Acetyl, methoxy, and halogen ring-substituted octyl phenylcyanoacrylates

Abstract

Novel trisubstituted ethylenes, acetyl, methoxy, and halogen ring-substituted octyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2(CH2)6CH3 (where R is 2-acetyl, 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,5,6-tetrafluoro, 2,3,4,5,6-pentafluoro, 3-bromo-4,5-dimethoxy, 5-bromo-2,3-dimethoxy, 3-chloro-2,6-difluoro) were prepared and copolymerized with styrene. The ethylenes 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. 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.