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

Abstract

The ordered [head-to-head (H-H) or tail-to-tail (T-T)] poly(amide-ester) was prepared by direct polycondensation of a symmetric monomer, isophthaloyl chloride with 4-aminophenethyl alcohol as a nonsymmetric monomer. The polymerization was conducted in NMP in the presence of triethylamine (TEA) at 0°C by slow addition of isophthaloyl chloride to 4-aminophenethyl alcohol, giving 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°C in NMP. The authentic H-H or T-T and random poly(amide-ester)s were prepared respectively to varify the structure of ordered polymer. The microstructure of polymers obtained was investigated by 1H and 13C spectroscopy, 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 ordered polymer was crystalline; On the other hand, the random poly(amide-ester) was amorphous. Furthermore, physical properties of H-H or T-T ordered polymer were compared with poly(amide-ester) obtained from isophthaloyl chloride and 4-(2-aminoethyl)phenol (constitutional isomer of monomer 4-aminophenetnyl alcohol).