Synthesis and styrene copolymerization of halogen ring-substituted isopropyl cyanophenyl propanoates
Benjamin Y Killam, Timothy S Bullock II, Juliana Carmichael, Shelby J Carvalho, Anais A Dominguez, Tyler Faith, Jesse Garcia, Andrew D Gould, Emily E Jacobs, Kirsten Kochan, Charles M Rubert Pérez, Sara M Rocus, Gregory B Kharas
Halogen ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 2-Br, 3-Br, 4-Br, 2-Cl, 3-Cl, 4-Cl, 2-F, 3-F, 4-F) were prepared and copolymerized with styrene. The compounds were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate. All the propenoates were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The monomers and copolymers were characterized by elemental analysis, FTIR, 1H and 13C-NMR. Thermal properties of the copolymers were estimated by DSC and TGA analyses.