Synthesis and polymerization of cyano-substituted monomers derived from 4-amino-α-methyl-β,β′-dicyanostyrene

A novel class of polymer precursors of the general formula, where A is an aromatic structure bearing amide or imide linkages, were synthesized. More particularly, 4-aminoacetophenone was condensed with malononitrile to afford 4-amino-α-methyl-β,β′-dicyanostyrene ( 1 ). The condensation of the latter with half molar amount of terephthaloyl dichloride, pyromellitic dianhydride, or benzophenone tetracarboxylic dianhydride yielded the polymer precursors. In addition, compound 1 was condensed with an equimolar amount of maleic anhydride to afford the corresponding maleimide. The monomers were characterized by elemental analyses, FT-IR, ¹H-NMR, and DTA. Crosslinked resins were obtained upon curing the monomers at 300°C for 72 h. They were stable up to 381-422°C in N₂ or air and afforded anaerobic char yields of 64-68% at 800°C. © 1994 John Wiley & Sons, Inc.