Synthesis and characterization of fluorinated poly(aryl ether ketone)s containing 1,4-naphthalene moieties

The new monomer 2,2-bis[4-(4-{4-fluorobenzoyl}-1-naphthoxy)phenyl]hexafluoropropane (2) was synthesized in a two-step reaction sequence. 2,2-bis[4-(1-naphthoxy)phenyl]hexafluoropropane (1) was prepared using the Ullmann ether synthesis reaction of 4,4-(hexafluoroisopropylidiene)diphenol with 1-bromonaphthalene. Friedel-Crafts acylation of 1 with 4-fluorobenzoyl chloride in methylene chloride containing dimethylsulfone selectively afforded 2 in 82% yield. The polycondensation of 2 with various bisphenols in DMAc in the presence of an excess of potassium carbonate as a condensation reagent was carried out at 165 degrees C to quantitatively afford the corresponding fluorinated poly(aryl ether ketone)s containing 1,4-naphthalene moieties. Thermal analysis of the polymers showed them to have T(g)s ranging from 194 to 230 degrees C and to be thermally stable in air up with initial weight losses at about 500 degrees C. In addition, these novel polymers exhibited excellent solubility in organic solvents including NMP, DMAc, and chloroform. (C) 1997 John Wiley & Sons, Inc.