Polybenzoxazine is obtained by ring-opening polymerization of monomers via thermal curing. Benzoxazine monomers can be prepared from phenols, primary amines and formaldehyde through Mannich condensation reaction either in solution or in melt state. They have considerable molecular design flexibility for monomers. Consequently, polybenzoxazine with desired properties may be obtained by tailoring the benzoxazine monomers. In this work, a variety of natural and unnatural amino acids, which could be readily available from plants, animals and the by-products of present agricultural and food-processing streams, was used as amino resource to prepare the fully bio-based benzoxazine monomers. The amino acid was firstly esterified, and then reacted with bio-based biphenol. The chemical structure of novel benzoxazine was characterized by FTIR and <sup>1</sup>H NMR spectroscopy. The curing behavior of the monomers was examined via FTIR and differential scanning calorimetry (DSC). The curing temperature of the novel monomers was more or less the same as that of traditional bisphenol A-aniline (BA-a) benzoxazine monomer. The thermal stability and mechanical property of the obtained polybenzoxazine were evaluated through thermogravimetric analysis (TGA) and tensile test. The results showed that the fully bio-based polybenzoxazine possessed the competitive thermal and mechanical properties as the petroleum-based polybenzoxazine. Furthermore, the raw materials are renewable and low cost compared with other commercial petroleum feedstock. The synthesis process of the new bio-based benzoxazine could expand the type of amino resource and extend the field of sustainable biomass polybenzoxazine resin.

Design and preparation of fully bio-based polybenzoxazine from amino acid

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.