Constitutional isomerism IV. Synthesis and characterization of poly(amide-ester)s from isophthaloyl chloride and 4-aminophenethyl alcohol

The ordered [head-to-head (H-H) or tail-to-tail (T-T)] poly(amide-ester) wa s prepared by direct polycondensation of a symmetric monomer, isophthaloyl chloride with 4-aminophenethyl alcohol as a nonsymmetric monomer. The polym erization was conducted in NMP in the presence of triethylamine (TEA) at Or : by slow addition of isophthaloyl chloride to 4-aminophenethyl alcohol, gi ving the ordered H-H or T-T poly(amide-ester) with an inherent viscosity of 0.30 dL g(-1), measured at a concentration of 0.5 g dL(-1) at 30 degreesC in NMP. The authentic H-H or T-T and random poly(amide-ester)s were prepare d respectively to varify the structure of ordered polymer. The microstructu re of polymers obtained was investigated by H-1 and C-13 spectrascopy, and it was found that the polymers obtained by direct polycondensation had the expected H-H or T-T ordered structure. The model reactions were studied in detail to demonstrate the feasibility of polymer formation. H-H or T-T orde red polymer was crystalline; On the other hand, the random poly(amide-ester ) was amorphous. Furthermore, physical properties of H-H or T-T ordered pol ymer were compared with poly(amide-ester) obtained from isophthaloyl chlori de and 4-(2-aminoethyl)phenol (constitutional isomer of monomer 4-aminophen ethyl alcohol).