Journal of Applied Polymer Science, Vol.53, No.2, 201-212, 1994
Cyano-Substituted Polyester, Polyurethanes, and Epoxy-Resin Derived from 2,6-bis(4-Hydroxybenzylidene)-1-Dicyanomethylene-Cyclohexane
The condensation of cyclohexanone with 4-hydroxybenzaldehyde utilizing dry HCl as the catalyst afforded 2,6-bis (4-hydroxybenzylidene) cyclohexanone. The latter was condensed with malononitrile to yield 2,6-bis (4-hydroxybenzylidene)-1-dicyanomethylene-cyclohexane, which was used as the starting material for the preparation of a novel class of polyesters, polyurethanes, and epoxy resins. In addition, a model diester and diurethane were synthesized and their spectroscopic data were correlated with those of the corresponding polymers. It was shown that the introduction of the dicyanomethylene groups in the polymer backbone remarkably improved the polymer solubility as well as its thermal stability. The crosslinked polymers obtained upon curing the polyester and polyurethanes at 300-degrees-C for 40 h were stable up to 365-407-degrees-C in N2 or air and afforded anaerobic char yields of 64-70% at 800-degrees-C.
Keywords:HOMOPOLYAMIDE;COPOLYAMIDES