Synthesis and Styrene Copolymerization of Novel Chloro and Fluoro Ring-Disubstituted Isopropyl Cyanophenylacrylates

Novel chloro and fluoro ring-disubstituted isopropyl 3-phenyl-2-cyanoacrylates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 2-chloro-4-fluoro, 2-chloro-6-fluoro, 3-chloro-2-fluoro, 3-chloro-4-fluoro, 4-chloro-3-fluoro) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and isopropyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. All the acrylates 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 IR, 1H and 13C-NMR, GPC, DSC, and TGA.