In this study, imine-containing polybenzoxazine vitrimer (C-ABZ) was synthesized through a condensation reaction between an aldehyde-containing benzoxazine oligomer (O-ABZ) and 1,12-dodecanediamine. The dynamic exchangeable characteristics of imine bonds impart C-ABZ with weldabilities and reprocessabilities. At the same time, the hydrophobic polybenzoxazine backbone significantly improve the water resistance of imine bonds.

Abstract

Traditional polybenzoxazine thermosets cannot be reprocessed or recycled due to the permanent crosslinked networks. The dynamic exchangeable characteristics of imine bonds can impart the networks with reprocessabilities and recyclabilities. This study reported a weldable, reprocessable, and water-resistant polybenzoxazine vitrimer (C-ABZ) crosslinked by dynamic imine bonds. It was synthesized through a condensation reaction between an aldehyde-containing benzoxazine oligomer (O-ABZ) and 1,12-dodecanediamine. The resulting C-ABZ was able to be welded and reprocessed due to the dynamic exchange of imine bonds. The tensile strengths of the welded C-ABZ and the reprocessed C-ABZ after three cycles of hot-pressing were 76.7, 81.3, 70.8, and 58.1 Mpa, with corresponding tensile strength recovery ratios of 74.1 %, 78.6 %, 68.4 %, and 56.1 %, respectively. Furthermore, the polybenzoxazine backbone significantly improved the water resistance of the imine bonds. After immersing in water for 30 days at room temperature, the weight gain of C-ABZ was less than 1 % with corresponding tensile strength and tensile strength retention ratio of 59.5 Mpa and 57.5 %, respectively. Although the heat resistance of C-ABZ decreased slightly with increased hot-pressing cycles, a glass transition temperature (T _{g, tanδ}) of 150 °C was retained after the third hot-pressing. Overall, these findings demonstrate that the C-ABZ possesses excellent comprehensive performances.