Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 6. Methyl, halogen and oxy ring-disubstituted octyl phenylcyanoacrylates

Abstract

Novel trisubstituted ethylenes, methyl, halogen, and oxy ring-disubstituted octyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2(CH2)6CH3 (where R is 4-methoxy-2-methyl, 4-methoxy-3-methyl, 3-ethoxy-4-methoxy, 4-ethoxy-3-methoxy, 3-benzyloxy-4-methoxy, 4-benzyloxy-3-methoxy, 2,3-(methylenedioxy), 3-bromo-4-methoxy, 5-bromo-2-methoxy, 2-chloro-3-methoxy, 2-chloro-6-methyl, 3-chloro-4-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.