Polymerization by phase transfer catalysis. 24. Synthesis of condensation polymers derived from halogenated diphenol-amides with the amide group in the side chain

Poly(amide-ester)s, poly(amide-carbonate)s and poly(amide-thiocarbonate)s d erived from the diphenols-amides N-(2,6-dibromo-4-nitrophenyl)-4,4-bis(4-hy droxyphenyl)-pentanamide (I) and N-(2,6-diiodo-4-nitrophenyl)-4,4-bis(4-hyd roxyphenyl)-pentanamide (II) and terephthaloyl chloride (a), isophthaloyl c hloride (b), and adipoyl chloride (c), and phosgene (d) and thiophosgene (e ) respectively, have been synthesized under phase transfer conditions using several quaternary ammonium salts as phase transfer catalysts. Benzyltriet hylammonium chloride (BTEAC) was effective in practically all cases due to the hydrophilicity of this catalyst. Poly(amido-ester)s derived from II and aromatic diacids were insoluble in all the organic solvents, and the effec tivity of the process was evaluated by the increase of the yields with resp ect to the essays without catalysts.