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

Abstract

AbstractSummary: 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.Synthesis of poly(amide urethane)s.magnified imageSynthesis of poly(amide urethane)s.