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Synthesis and characterization of polyaryleneetherketone triphenylphosphine oxides incorporating cycloaliphatic/cage hydrocarbon structural units
Authors:Thuy D. Dang  Matthew J. Dalton  N. Venkatasubramanian  Joel A. Johnson  Clifford A. Cerbus  William A. Feld
Abstract:New high temperature polyaryleneetherketone triphenylphosphine oxides incorporating trans‐1,4‐cyclohexane, 1,3‐adamantane, and 4,9‐diamantane structural units were synthesized by the base‐promoted polymerization reaction between 4,4′‐difluorotriphenylphosphine oxide and the novel dihydroxy monomers trans‐1,4‐bis(4‐hydroxybenzoyl)cyclohexane, 1,3‐bis(4‐hydroxybenzoyl)adamantane, and 4,9‐bis(4‐hydroxybenzoyl)diamantane. The monomers were synthesized in a good yield by a two‐step procedure involving the Friedel–Crafts acylation of anisole by the diacid chlorides trans‐1,4‐cyclohexanedicarbonyl chloride, 1,3‐adamantanedicarbonyl chloride, and 4,9‐diamantanedicarbonyl chloride, followed by demethylation with pyridine hydrochloride. The polymers, which could be processed into tough, free standing films from organic solvents, exhibited high Tg's in the range of 192–239° as well as thermooxidative stabilities (5% weight loss in air) in the range of 445–490°. Preliminary results from a UV–visible spectroscopic study of dilute solutions of the polymers in chloroform showed absorption maxima in the 263–274 nm region and transparency to spectral radiation in the 300–800 nm range, indicating that these triphenylphosphine oxide polymers could have potential applications for space thermal control coatings. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 6134–6142, 2004
Keywords:polycondensation  triphenylphosphine oxides  poly(etherketones)  cage hydrocarbons  high performance polymers  thermal control coatings  high temperature materials  thin films
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