Synthesis and styrene copolymerization of novel methoxy and methyl ring-trisubstituted isopropyl cyanophenylacrylates
Joshua J Ludtke, Sara M Rocus, William S Schjerven, Gregory B Kharas
Novel methoxy and methyl ring-trisubstituted isopropyl 3-phenyl-2-cyanoacrylates, RPhCH=C (CN) CO2 CH (CH3)2 (where R is 2, 3-dimethyl-4-methoxy, 2, 5-dimethyl-4-methoxy, 2, 4-dimethoxy-3-methyl, 2, 4-dimethoxy-6-methyl, 3, 5-dimethoxy-4-hydroxy, 4-hydoxy-3, 5-dimethyl) 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.