Preparation of 2‐ethyl‐4‐methylimidazole derivatives as latent curing agents and their application in curing epoxy resin

Abstract

ABSTRACT Three kinds of 2‐ethyl‐4‐methylimidazole (EMI) derivatives ( N ‐acetyl EMI, N ‐benzoyl EMI, and N ‐benzenesulfonyl EMI) were synthesized through the reaction of EMI with acetyl chloride, benzoyl chloride, and benzenesulfonyl chloride, respectively. And the structure was confirmed by Fourier transform infrared spectroscopy (FTIR) and 1 H‐nuclear magnetic resonance spectroscopy ( 1 H NMR) spectra. Furthermore, the synthesized EMI derivatives were applied in diglycidyl ether of bisphenol A epoxy resin (DGEBA) as latent curing agent. Differential scanning calorimeter (DSC) was used to analyze the curing behavior of DGEBA/EMI derivative systems, indicating DGEBA could be efficiently cured by the EMI derivatives at 110∼160°C, and the corresponding curing activation energy ranged from 71 to 86 kJ/mol. Viscosity data proves that the storage life of DGEBA with N ‐acetyl EMI (NAEMI), N ‐benzoyl EMI (NBEMI), and N ‐benzenesulfonyl EMI (NBSEMI) at room temperature was 38 d, 50 d, and 80 d, and that at 10°C was 90 d, 115 d, and 170 d, respectively. Besides, thermogravimetry (TG), izod impact strength (IIS), and tensile shear strength (TSS) were tested to characterize the thermal stability and mechanical properties of DGEBA cured by EMI derivatives. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132 , 42563.