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Cyano‐substituted polyester, polyurethanes, and epoxy resin derived from 2,6‐bis(4‐hydroxybenzylidene)‐1‐dicyanomethylene–cyclohexane
Author(s) -
Diakoumakos Constantions D.,
Mikroyannidis John A.
Publication year - 1994
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1994.070530209
Subject(s) - cyclohexanone , cyclohexane , epoxy , polyester , thermal stability , polymer , polymer chemistry , solubility , malononitrile , curing (chemistry) , materials science , thermosetting polymer , polyurethane , chemistry , catalysis , organic chemistry
The condensation of cyclohexanone with 4‐hydroxybenzaldehyde utilizing dry HCI 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°C for 40 h were stable up to 365–407°C in N 2 or air and afforded anaerobic char yields of 64–70% at 800°C. © 1994 John Wiley & Sons, Inc.