Novel halogen ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C3H7 (where R is 2-fluoro-5-methyl, 3-iodo-4-methoxy, 5-iodo-2-methoxy, 3,5-dichloro, 3,4-difluoro, 3,5-difluoro, 2-chloro-4-fluoro, 2-chloro-6-fluoro, 3-chloro-2-fluoro, and 3-chloro-4-fluoro) were prepared and copolymerized with styrene. The propenoates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and propyl cyanoacetate, and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. All the propenoates were copolymerized with styrene (M1) 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 200-500ºC range with residue (1-3% wt.), which then decomposed in the 500-800ºC range.
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