A naringenin-based benzoxazine with an intramolecular hydrogen bond as both a thermal latent polymerization additive and property modifier for epoxy resins.

Epoxy resins are constantly attracting attention from industrial applications due to their excellent comprehensive properties. However, the traditional curing agents for liquid epoxy resins react with epoxides even at room temperature, which causes difficulties in processing since such mixtures cannot be directly used as single-component materials. In order to improve the shelf life of the mixtures, we have designed an intramolecular hydrogen bond-containing benzoxazine monomer as a smart thermal latent polymerization agent for epoxy resins. The newly obtained benzoxazine, NAR-a, has been synthesized from the Mannich condensation of naringenin, aniline and paraformaldehyde. In addition to playing the role of a curing agent, NAR-a has also performed as an excellent property modifier for epoxy thermosetting systems. The resulting thermoset based on the NAR-a/epoxy thermosetting system exhibits high thermal stability and good intrinsic flame retardance, with a T g temperature of 201 °C, a T d5 temperature of 349 °C, a low CET value (32.4 ppm per °C) and low heat release capacity (HRC of 159.1 J g -1 K -1 ). The combined long-term storage stability and versatility of the intramolecular hydrogen bond-containing benzoxazine/epoxy system provide a new strategy for the development of one-component epoxy-related thermosetting resins for application in high-performance areas.