Imidazole derivative with an intramolecular hydrogen bond as thermal latent curing accelerator for epoxy/phenolic resins

Abstract

One‐component epoxy systems with long shelf life during storage or transportation, while high curing reactivity during molding as well as satisfactory mechanical and thermal performances after curing, are extremely essential for industrial application. Herein, we used salicylaldehyde and o‐phenylenediamine to synthesize 2‐(2′‐hydroxyphenyl)‐1H‐benzimidazole (HPBI), an imidazole derivative with an intramolecular hydrogen bond between the phenolic hydroxyl group and the pyridine‐type nitrogen atom of imidazole ring, and further employed HPBI as a thermal latent curing accelerator for epoxy/phenolic resins. The intramolecular hydrogen bond endowed HPBI with inert activity toward resins at room temperature, making the one‐component resin system a long‐term storage stability (21 days of shelf life at 30°C). Once rising the temperature to a high degree, a rather high activity of HPBI to accelerate the curing process of epoxy/phenolic resins. It was attributed to the effective release of high activity of the pyridine‐type nitrogen by breaking the intramolecular hydrogen bond at high temperature. In addition, the resulted thermosets from HPBI also possessed the comparable Tg (>130°C, determined by DMA) and thermostability (Td‐5% > 380°C) with that from common curing accelerators. Therefore, HPBI was proved to be a promising thermal latent curing accelerator applied in electronic packaging field.

Understanding the interaction mechanism of carbazole/anthracene with N,N-dimethylformamide: NMR study substantiated carbazole separation

“…the N–H of carbazole and the proton in H 2 O, moves to the downfield region, which means that the strength of hydrogen bonds between DMF and carbazole becomes stronger. 37 Notably, other chemical shifts from carbazole and anthracene do not change during the cooling process.…”

Accelerated‐curing epoxy structural film adhesive for bonding lightweight honeycomb sandwich structures

“…They found that both 2E4MI and BF 3 accelerated the onset of curing and that increasing the flame retardant content in the modified epoxy resin reduced the glass transition temperature. For simultaneously achieving long shelf life during storage and high reactivity during molding to the epoxy resin, Wei et al 32 synthesized an imidazole derivative, 2-(2 0 -hydroxyphenyl)-1H-benzimidazole (HPBI), as a thermal latent curing accelerator for epoxy/phenolic resins. The intermolecular hydrogen bonds in HPBI render it inert to epoxy resins at room temperature.…”