Microstructure and Properties of Poly(amide urethane)s: Comparison of the Reactivity of α-Hydroxy-ω-O-phenyl Urethanes and α-Hydroxy-ω-O-hydroxyethyl Urethanes

Poly(amide urethane)s were prepared from ε-caprolactam, amino alcohols, and diphenyl carbonate or ethylene carbonate in three steps. Polycondensation was performed either with α-hydroxy-ω-O-phenyl urethanes or with α-hydroxy-ω-O-hydroxyethyl urethanes; it was found that the reactivity at 90 °C of the first is much higher than that of the latter. For nearly equal reactivity, the temperature for the polycondensation of α-hydroxy-ω-O-hydroxyethyl urethanes had to be increased from 90 °C to 150 °C. The microstructure of the resulting poly(amide urethane)s differs by the content of urea groups in the polymer chains, which is 5% for poly(amide urethane)s prepared from α-hydroxy-ω-O-phenyl urethanes and 15% for poly(amide urethane)s prepared from α-hydroxy-ω-O-hydroxyethyl urethanes. As a consequence, the thermal properties of the poly(amide urethane)s differ slightly.