Synthesis and crosslinking of cyano-substituted polyamides and polyimides prepared from 1-(2,2-dicyano-1-hydroxyviyl)-3,5-diaminobenzene,sodium salt

3,5-Dinitrobenzoyl chloide was condensed with malononitrile in the presence of sodium hydroxide under phase-transfer conditions to afford 1-(2,2-dicyano-1-hydroxyvinyl)-3,5-dinitrobenzene, sodium salt, which was catalytically hydrogenated to the corresponding diamine. The latter was used as starting material for the preparation of unsaturated cyanosubstituted polyamides and polyimides. The polymers were soluble in polar aprotic solvents, dilute sodium hydroxide, and certain strong inorganic and organic acids. Upon curing at 300°C for 65 h, crosslinked polymers were obtained that were stable up to 392–404°C in N₂ or air and afforded an anaerobic char yield of 60–71% at 800°C. Their glass transition temperatures as determined by thermal mechanical analysis (TMA) were 221–275°C. © 1995 John Wiley & Sons, Inc.