Synthesis and Styrene Copolymerization of Novel Dihalogen Ring-Substituted Isopropyl Cyanophenylacrylates

Novel dihalogen ring-substituted isopropyl 3-phenyl-2-cyanoacrylates, RPhCH=C(CN)CO₂CH(CH₃)₂ (where R is 2,5-dibromo, 3,5-dibromo, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro) 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 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.