Novel Copolymers of Styrene. 2. Oxy Ring-Substituted 2-Cyano-3-phenyl 2-propenamides

Abstract

Novel electrophilic trisubstituted ethylene monomers, oxy ring substituted 2-cyano-3-phenyl-2-propenamides, RC6H4CH˭ C(CN)CONH2 (where R is 2-CH3O, 3-CH3O, 4-CH3O, 2-C2H5O, 3-C2H5O, 4-C2H5O, 4-C3H7O, 4-C4H9O, 4-C6H13O, 3-C6H5O, 4-C6H5O, 3-C6H5CH2O, 4-C6H5CH2O), were synthesized by potassium hydroxide catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and cyanoacetamide, and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. Novel copolymers of the ethylenes and styrene were prepared at equimolar monomer feed composition by solution copolymerization in the presence of a radical initiator, AIBN 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. High Tg of the copolymers in comparison with that of polystyrene indicates a substantial decrease in chain mobility of the copolymer due to the high dipolar character of the trisubstituted ethylene monomer unit. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200–500°C range with residue (0.2–1.2 wt%), which then decomposed in the 500–800°C range.