Epoxy resins based on aromatic glycidylamines. II. Preparation of<i>N,N,N′,N′</i>‐tetraglycidyl‐4,4′‐diaminodiphenylmethane from 4,4′‐diaminodiphenylmethane: Analysis of product by GPC and HPLC

Abstract

Abstract N,N,N′,N′ ‐tetrakis(2,3‐epoxypropyl)‐4,4′‐diaminodiphenylmethane ( N,N,N′,N′ ‐tetraglycidyl‐4,4′‐diaminodiphenylmethane, TGDDM) and an intermediate of its synthesis, N,N,N′,N′ ‐tetrakis(2‐hydroxy‐3‐chloropropyl)‐4,4′‐diaminodiphenylmethane ( N,N,N′,N′ ‐tetrachlorohydrin of 4,4′‐diaminodiphenylmethane, TCHDDM), were analyzed by GPC and HPLC. The main impurities were identified by analogy with N,N ‐diglycidylaniline (DGA) and N,N ‐dichlorohydrin of aniline (DCHA) that had been analyzed in our previous work, 1 and by IR, NMR, and mass spectroscopy after their isolation by semipreparative HPLC. Attention was also paid to quantitative determination of the TGDDM content and to GPC elution behavior of TGDDM and TCHDDM‐based oligomers.