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Synthesis and Properties of Copolymers of Poly(ether ketone ketone) and Poly(ether ether ketone ketone) Containing Naphthalene Moieties and Pendant Cyano Groups

Department of Chemistry, Jiangxi Normal University, Nanchang 330022, P.R. China

^* To whom correspondence should be addressed.

	Abstract

A new monomer containing naphthalene, 2,6-bis(-naphthoxy)benzonitrile (BNOBN) was synthesized by reaction of -naphthol with 2,6-difluorobenzonitrile in N-methyl-2-pyrrolidone (NMP) in the presence of KOH and K₂CO₃. Novel copolymers of poly(ether ketone ketone) and poly(ether ether ketone ketone) containing naphthalene moieties and pendant cyano groups were prepared by electrophilic Friedel–Crafts solution copolycondensation of terephthaloyl chloride (TPC) with varying mole proportions of diphenyl ether and 2,6-bis(-naphthoxy)benzonitrile (BNOBN) using 1,2-dichloroethane as solvent and NMP as Lewis base in the presence of anhydrous AlCl₃. The crystallinity and melting temperatures of the polymers were found to decrease as the concentration of BNOBN in the polymer increased, whereas the glass transition temperatures of the polymers increased as the concentration of BNOBN in the polymer increased. The copolymers with 20–25 mol% BNOBN had high T_g values of 182–184 °C; moderate T_m values of 324–335 °C; tensile strengths of 101.8–103.2 MPa, Young's moduli of 3.14–3.23 GPa, and elongations at break of 15–18%. The copolymers exhibited outstanding thermal stability and good resistance to organic solvents, acidity and alkali.

Key Words: Poly(aryl ether ketone), 2, 6-bis(-naphthoxy)benzonitrile, terephthaloyl chloride, thermal property, electrophilic polycondensation

First published on January 21, 2009
High Performance Polymers 2009, doi:10.1177/0954008308099531


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