Eugenol‐derived bio‐benzoxazine resins: Synthesis, characterization, and exceptional thermal stability

Abstract

In this study, we succesfully synthesized bio‐benzoxazine resins using eugenol, a bio‐based phenolic compound, in combination with three distinct functional amines: ethanamine, aniline, and hexane‐1,6‐diamine. Characterization of the resulting bio‐benzoxazine resins, namely E‐ea (eugenol, ethanamine), E‐a (eugenol, aniline), and E‐dh (eugenol, hexane‐1,6‐diamine), was performed through 1H NMR spectroscopy, FTIR spectroscopy, high‐resolution mass spectrometry, and elemental analysis. Thermal properties were investigated using thermogravimetric analysis (TGA) for both the eugenol‐derived bio‐benzoxazines (E‐ea, E‐a, E‐dh) and their corresponding polybenzoxazines (PE‐ea, PE‐a, PE‐dh). Notably, all eugenol‐based polybenzoxazines exhibited excellent thermal stability with very similar characteristics. Our findings suggest that the presence of allyl groups in eugenol promoted a more cross‐linked network structure compared to other functional groups on amines. As a result, eugenol‐derived bio‐benzoxazines demonstrated superior thermal properties, illustrated by their impressive char yields: PE‐ea; 45.6%, PE‐a; 45.1%, and PE‐dh; 44.1%.