3-(4-hydroxyphenyl)propanoic acid, so-called phloretic acid (PA), is a naturally occurring phenolic compound which can be produced from the hydrogenation of p-coumaric acid or synthesized from phloretin, a by-product of apple tree leaves. It is explored hereby as a renewable building block for enhancing the reactivity of –OH bearing molecules towards benzoxazine ring formation instead of phenol. PA is used to bring phenolic functionalities by reaction with model molecules (ethylene glycol, as well as two polyethylene glycol molecules with molar masses corresponding to 400 g/mol and 2000 g/mol) via a solvent-free Fischer esterification. These phenolic groups are further reacted with a bio-based amine (furfurylamine) to form almost 100% bio-based benzoxazine end-capped molecules. Very interestingly, the whole synthesis of Bz monomers from PEG400 and PEG2000 does not require both solvent nor purification, and their polymerization led to a set of materials with thermal and thermo-mechanical properties suitable for a wide range of applications.

Phloretic acid as an alternative to the phenolation of aliphatic hydroxyls for the elaboration of polybenzoxazine

255th National Meeting (2018)

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