Synthesis and characterization of aromatic poly(ether ketone amide)s

A general method for the preparation of amide-containing aromatic polyether ketones has been developed. Polymerization is based on a ketone-activated halo displacement in amide-containing bis(4-fluorobenzoyl) moieties by phenoxides. N,N-Bis[4-(4-fluorobenzoyl)-(4-phenoxyphenylJ]terephthalamide and 4-[(4-fiuorobenzoyl)-(4-phenoxyphenylcarbamoyl)]-N-[(4-fluorobenzoyl)-(4-phenoxyphenyl)]phthalimide were prepared by reaction of 4-fluoro-benzoyl chloride with N,N.bis(4-phenoxyphenyl)terephthalamide and 4-(4.phenoxy-phenylcarbamoyl)-N-(4-phenoxyphenyl)phthalimide, respectively, in dichloromethane in the presence of aluminum chloride. Reaction of N,N-bis[4-(4-fluorobenzoyl)-(4-phenoxyphenyl)]-terephthalamide and 4-[(4-fluorobenzoyl(4-phenoxyphenylcarbamoyl)]-N-[(4-fluorobenzoyl)-(4-phenoxyphenyl)]phthalimide with diphenols in an aprotic solvent in the presence of potassium carbonate gave a series of aromatic poly(ether ketone amide)s. Films of the aromatic poly(ether ketone amide)s displayed good thermal stability, flexibility, and T, values ranging from 134 to 186 CC. The dielectric constants of the films were characterized as a function of relative humidity (RH).