Integrating plant oils into thermally curable main-chain benzoxazine polymers via ADMET polymerization

• A biobased benzoxazine-containing diene was designed and synthesized.
• ADMET polymerization was applied to produce thermally curable linear polymers.
• The oxazine groups have shown to readily undergo thermal ring-opening polymerization.
• Flexible crosslinked polymer networks were obtained.

A novel biobased α,ω-diene bearing a thermally curable benzoxazine group is synthesized and polymerized via acyclic diene metathesis (ADMET) using Hoveyda–Grubbs second generation catalyst. The benzoxazine-containing diene monomer was designed based on 10-undecenoic acid, a castor oil derived platform chemical. The Mn and crosslinker content can be modulated by using a monofunctional comonomer to end-cap polymer chains. Differential scanning calorimetry was used to demonstrate that obtained thermoplastic prepolymers are able to yield thermosets after thermally activated ring opening polymerization just simply by heating up to around 200 °C. Thermal and mechanical properties of the cured polybenzoxazines are also discussed.

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