Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 9. Halogen, methyl, methoxy and nitro ring-substituted octyl phenylcyanoacrylates

Abstract

Novel trisubstituted ethylenes, halogen, methyl, methoxy and nitro ring-substituted octyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2(CH2)6CH3 (where R is 2-chloro-6-fluoro, 3-chloro-4-fluoro, 2-chloro-5-nitro, 4-chloro-3-nitro, 5-chloro-2-nitro, 5-iodo-2-methoxy, 2,4,5-trimethyl, 2,4,6-trimethyl, pentamethyl, 2,3-dimethyl-4-methoxy, 2,5-dimethyl-4-methoxy, 2,4-dimethoxy-3-methyl) 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.