Synthesis and Characterization of Ordered Poly(amide−ester)s from Isophthaloyl Chloride and 4-(2-Aminoethyl)phenol

• Published in: Macromolecules 1999-06, Vol.32 (12), p.3851-3858
• Main Authors: Li, Seino, Hiroshi, Yonetake, Koichiro, Ueda, Mitsuru
• Format: Article
• Language: English
• Subjects: Applied sciences; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; Polycondensation; Preparation, kinetics, thermodynamics, mechanism and catalysts
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/ma981919u

The ordered [head-to-head (H−H) or tail-to-tail (T−T)] poly(amide−ester) was prepared by polycondensation of a symmetric monomer, isophthaloyl chloride (1), with 4-(2-aminoethyl)phenol (2) as a nonsymmetric monomer. The polymerization was conducted in NMP in the presence of triethylamine (TEA) at −20 °C by slow addition of 1 to 2, giving the ordered H−H or T−T poly(amide−ester) with an inherent viscosity of 0.27 dL/g, measured at a concentration of 0.5 g/dL at 30 °C in NMP. The authentic H−H or T−T, H−T ordered and random poly(amide−ester)s were prepared to verify the structure of ordered polymers. The microstructure of polymers obtained was investigated by 1H and 13C NMR spectroscopy, and it was found that the polymer obtained by polycondensation had the expected H−H or T−T ordered structure. Furthermore, the model reactions were studied in detail to demonstrate the feasibility of polymer formation. The constitutional regularity of polymers influenced the solubility, thermal properties, and crystallinity.