Chavicol benzoxazine: Ultrahigh Tg biobased thermoset with tunable extended network

Published Date
Received 2 May 2016, Revised 21 June 2016, Accepted 23 June 2016, Available online 25 June 2016.

Author
Ludovic Dumas. Author links open the author workspace.Opens the author workspaceOpens the author workspacea. Numbers and letters correspond to the affiliation list. Click to expose these in author workspaceb. Numbers and letters correspond to the affiliation list. Click to expose these in author workspaceLeïla Bonnaud. Author links open the author workspace.a. Numbers and letters correspond to the affiliation list. Click to expose these in author workspaceMarjorie Olivier. Author links open the author workspace.b. Numbers and letters correspond to the affiliation list. Click to expose these in author workspaceMarc Poorteman. Author links open the author workspace.b. Numbers and letters correspond to the affiliation list. Click to expose these in author workspacePhilippe Dubois. Author links open the author workspace.a. Numbers and letters correspond to the affiliation list. Click to expose these in author workspace

a

Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), Materia Nova Research Center & University of Mons, 23 Place du Parc, B-7000 Mons, Belgium

b

Department of Materials Science, Materials Engineering Research Center (CRIM), University of Mons, 23 Place du Parc, B-7000 Mons, Belgium

Highlights

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Robust synthesis of a bio based bis-benzoxazine.

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Allyl functionalized benzoxazine.

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Tunable extended network.

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Excellent thermomechanical properties.

Abstract

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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http://www.sciencedirect.com/science/article/pii/S001430571630355X