POLY(ARYL ETHER AMIDES) - SELF POLYMERIZATION OF AN A-B MONOMER VIA AMIDE-ACTIVATED ETHER SYNTHESIS

A synthetic approach for the preparation of poly(aryl ether amides) has been developed where the generation of an aryl ether linkage was the polymer-forming reaction. The amide moiety was found to be sufficiently electron withdrawing to activate halo-substituents, towards nucleophilic aromatic substitution polymerizations, analogous to conventional activating groups (i.e, sulfone, ketone etc.). Several new A-B monomers, 4-fluoro-N-(4-hydroxyphenyl)benzamide, 1, and 4-fluoro-N-(3-hydroxyphenyl)benzamide, 2, which contain both an amide-activated fluoro group and a phenol group were prepared and their self polymerization studied. Compounds 1 and 2 were prepared by the condensation of 4-fluorobenzoyl chloride with either 4-or 3-aminophenol, respectively. The polymerizations were carried out in an N-methyl-2-pyrrolidone (NMP)/N-cyclohexyl-2-pyrrolidone (CHP) solvent mixture in the presence of potassium carbonate. Several new high molecular weight poly(aryl ethers) were prepared by this route with Tg's in the 225-degrees-C range.