Polymerization by phase transfer catalysis - 23. Synthesis of poly(amide-ester)s derived from diphenols with the amide group in the side chain

The synthesis of poly(amide-ester)s derived from the diphenol-amides N-(2, 6-dichloro-4-nitrophenyl)-2,2-bis(4-hydroxyphenyl)-propanamide, N-(2,6-dichloro-4-nitrophenyl)-3,3-bis(4-hydroxyphenyl)- butanamide, and N-(2,6-dichloro-4-nitrophenyl)-4, 4-bis(4-hydroxyphenyl)-pentanamide and terephthaloyl chloride, isophthaloyl chloride and adipoyl chloride, is described under phase transfer conditions, using several quaternary ammonium salts as phase transfer catalysts. The behaviour of the catalysts was evaluated through the yields and inherent viscosity measurements and compared with those obtained without a catalyst. In general, the phase-transfer process was effective, and the best catalyst was benzyltriethylammonium chloride, which has hydrophilic characteristics and is suitable for transporting lypophilic dianions such as those used in this synthesis. Other catalysts also showed a good behaviour. All poly(amide-ester)s were insoluble in the reaction media, which limited their growth and the molecular wieght.