Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 11. Halogen ring-substituted propyl 2-cyano-3-phenyl-2-propenoates.

Novel trisubstituted ethylenes, ring-substituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C3H7 (where R is 4-chloro-3-fluoro, 2-fluoro-5-iodo, 2-fluoro-6-iodo, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-trifluoromethoxy, 3-trifluoromethoxy, and 4-trifluoromethoxy) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and propyl cyanoacetate and characterized by CHN analysis, FTIR, 1H and 13C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70 °C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by FTIR, 1H and 13C NMR. Decomposition of the copolymers in nitrogen (TGA) occurred in two steps, first in the 250-500 °C range with residue (0.5-3.1% wt.), which then decomposed in the 500-700 °C range. [ABSTRACT FROM AUTHOR]