Chavicol benzoxazine: Ultrahigh Tg biobased thermoset with tunable extended network

LudovicDumas, LeïlaBonnaud, MarjorieOlivier, MarcPoorteman, PhilippeDubois


A novel biobased benzoxazine monomer containing additional allyl functionality was synthesized using a solventless approach from the reaction of a natural occuring phenol: chavicol, para-phenylene diamine and formaldehyde. The chemical structure of this functionalized benzoxazine monomer was confirmed by 1H NMR and FTIR. Its polymerization was investigated and monitored by DSC showing two well defined exotherms allowing the selective ring-opening polymerization of benzoxazine functions and the preservation of the allyl functionality. The network crosslink density could be further increased via the controlled polymerization of allyl functionalities with a post-cure in order to adjust the thermo-mechanical properties. When both networks were polymerized, the thermoset presented an excellent thermo-mechanical stability with a Tα higher than 350 °C as measured by DMTA. This exceptional behavior for a potentially biobased benzoxazine resin will allow the preparation of sustainable high performance biocomposite materials.

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