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 halosubstituents, 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 °C range. © 1992 Springer-Verlag.