Synthesis and characterization of vanillin derived bio-based benzoxazine resin for high temperature application

Abstract

Purpose This study aims to synthesize two different benzoxazines (Bz) monomers using bio-based and petroleum-based primary amines, respectively, and they have been compared to study their thermal and mechanical performances. Design/methodology/approach A bio-based bisphenol, Divanillin (DiVa), was formed by reacting two moles of vanillin with one mole of ethylenediamine (EDA) which was then reacted firstly with paraformaldehyde and EDA to form the benzoxazine DiVa-EDA-Bz, and secondly with paraformaldehyde and furfuryl amine (FFA) to form the benzoxazine DiVa-FFA-Bz. The molecular structure and thermal properties of the benzoxazines were characterized by fourier transform infrared spectroscopy and nuclear magnetic resonance (1H,13C) spectroscopies, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), respectively. The benzoxazines were further coated on mild steel panels to evaluate their mechanical properties and chemical resistance. Findings The DSC results of DiVa-FFA-Bz showed two exothermic peaks related to crosslinking compared to the one in DiVa-EDA-Bz. The DiVa-FFA-Bz also showed a higher heat of polymerization than DiVa-EDA-Bz. The TGA results showed that DiVa-FFA-Bz exhibited higher thermal stability with a residual char of 54.10% than 43.24% for DiVa-EDA-Bz. The chemical resistance test results showed that DiVa-FFA-Bz showed better chemical resistance and mechanical properties due to its higher crosslinking density. Originality/value This study shows the use of bio-based materials, vanillin and FFA, for synthesizing a benzoxazine resin and its application at high temperatures.