Naphthalene-based poly(aryl ether)s. II. Synthesis and characterization of poly(ether ketone)s containing two 1,4-naphthylene moieties in the repeat unit

Abstract

Two new monomers, 4-chloro-1-(4′-fluoro-1-naphthoyl)naphthalene and 1,4-bis(4′-fluoro-1′-naphthoyl)benzene, have been synthesized and polymerized with four different bisphenols to give two series of the naphthalene-based poly(ether ketone)s that are analogous to commercial PEEK and PEEKK. The effect of the introduction of one or two 1,4-naphthylene moieties, in the backbone of the repeat unit, on the glass transition temperatures has been studied. The glass transition temperatures usually increased by 20–45 °C upon replacing one 1,4-phenylene with one 1,4-naphthylene moiety. All new poly (ether ketone)s prepared in tetramethylene sulfone were amorphous, with the glass transition temperatures in a range of 212–273 °C. The polymer produced from 1,4-bis(4′-fluoro-1′-naphthoyl)benzene and 1,4-hydroquinone in phenyl sulfone as a solvent at 300 °C showed semicrystalline properties with a melting temperature of 310 °C. Keywords: naphthalene, poly(ether ketone)s, synthesis, characterization, glass transition temperature.