Novel trisubstituted ethylenes, ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C3H7 (where R is 2-bromo-4-methyl, 2-chloro-6-methyl, 3-chloro-4-methyl, 2,5-dibromo, 3,5-dibromo, 2,3-dichloro, and 2,4-dichloro) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and propyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H and 13C-NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, 1H and 13C-NMR, GPC, DSC, and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500C range with residue (7-12% wt.), which then decomposed in the 500-800C range.

Synthesis and copolymerization with styrene of novel bromo and chloro ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates

254th National Meeting (2017)

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