Thermal decomposition behavior of bis‐aminimides and their application to polymerization of epoxide

Bis‐aminimide compounds [bis‐N, N,‐dimethyl‐N,‐(2‐hydroxypropyl)‐amine‐N,′‐adipimide (1) and bis‐trimethylamine adipimide (2)] were found to exhibit different thermal decomposition behavior and polymerization efficiency for an epoxide (phenyl glycidyl ether, PGE). The thermal decomposition rate of 1 was much higher than that of 2. It seemed that hydrogen bonding enhanced the decomposition rate. Compound 1 was thermolyzed to give a diisocyanate and a tertiary aminoalcohol, which subsequently reacted with each other to give a urethane. When 2 was heated, the isocyanate generated from 2 remained unreacted. PGE reacted with thoseaminimides to give different products, depending on their thermolyzed products. Mixtures of diisocyanate, tertiary amine, and PGE were used in the model reactions, and the thermal reaction between the expected decomposition products of aminimides was investigated in the presence and absence of PGE. The amount of high molecular weight fraction in PGE + 2 is greater than that of PGE + 1. In the former, the free isocyanate groups may act as a chain extender to give higher molecular weight fractions.