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Abstract
Cyclohexanone was condensed with a double molar amount of 3-nitrobenzaldehyde in the presence of dry HCl as catalyst to yield 2,6-bis(3-nitrobenzylidene)cyclohexanone. The latter was catalytically hydrogenated to 2,6-bis(3-aminobenzylidene)cyclohexanone (BABC) by means of hydrazine hydrate. New unsaturated polyamides and polyimides were prepared by reacting BABC with terephthaloyl dichloride and pyromellitic dianhydride or benzophenone tetracarboxylic dianhydride, respectively. Model diamide and diimide were synthesized from the reactions of BABC with benzoyl chloride and phthalic anhydride, respectively. In addition, BABC reacted with maleic and nadic anhydride to yield a bismaleimide and bisnadimide which were utilized as new polymer precursors. Monomers and model compounds were characterized by i.r. and 1H-NMR spectroscopy. Characterization of polymers was accomplished by i.r., DTA and inherent viscosity measurements. Cured resins were obtained by heating the unsaturated polymers and polymer precursors at 265° for 27 hr. They were stable up to 345–363° in N 2 or air and afforded anaerobic char yields of 52–61% at 800°.
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