Polybenzoxazines (PBz) have been developed by academia and industry as a promising substitute of phenolic and epoxy resins due to their outstanding properties. However, PBz have some shortcomings constraining their industrial applications such as their difficult processability. One strategy to overcome this drawback is the incorporation of benzoxazine groups onto a processable polymer chain. In this communication will be gathered results about the functionalization of the aliphatic hydroxyl groups of ethylene glycol and polyethylene glycol (P)EG, for the elaboration of polybenzoxazines. P(EG) are functionalized by Fischer esterification with phloretic acid, a naturally occurring phenylpropanoid phenol, leading to phenol-terminated molecules. These molecules are further reacted with furfurylamine, a bio-based amine, to form fully bio-based benzoxazine end-capped molecules. Interestingly, the two-step synthesis is performed without solvent and does not require purification. The polymerization of the synthesized end-chain benzoxazines leads to a set of materials with suitable thermal and thermo-mechanical properties for a wide range of applications. This novel approach paves the way toward the benzoxazine functionalization of hydroxyl bearing compounds like (bio)polymers, nanoparticles and even metallic surfaces like steel.

Solventless synthesis of fully bio-based benzoxazine polymers from phloretic acid, polyethylene glycol and furfurylamine

255th National Meeting (2018)

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