SYNTHESIS AND CHARACTERIZATION OF FLUORINATED POLY(ARYL ETHER KETONE)S CONTAINING 1,4-NAPHTHALENE MOIETIES

The new monomer luorobenzoyl}-1-naphthoxy)phenyl]hexafluoropropane (2) was synthesized in a two-step reaction sequence. 2,2-bis[4-(1-naphtho xy)phenyl]hexafluoropropane (1) was prepared using the Ullmann ether s ynthesis reaction of 4,4-(hexafluoroisopropylidiene)diphenol with 1-br omonaphthalene. Friedel-Crafts acylation of 1 with 4-fluorobenzoyl chl oride in methylene chloride containing dimethylsulfone selectively aff orded 2 in 82% yield. The polycondensation of 2 with various bisphenol s in DMAc in the presence of an excess of potassium carbonate as a con densation reagent was carried out at 165 degrees C to quantitatively a fford the corresponding fluorinated poly(aryl ether ketone)s containin g 1,4-naphthalene moieties. Thermal analysis of the polymers showed th em 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. I n addition, these novel polymers exhibited excellent solubility in org anic solvents including NMP, DMAc, and chloroform. (C) 1997 John Wiley & Sons, Inc.