High performance thermoset polybenzoxazine has a hydroxyl group on each repeat unit. Yet, it is highly hydrophobic due to the hydroxyl groups forming intramolecular six-membered hydrogen bonding with the Mannich base. By exchanging the oxygen for the isoelectric sulfur, benzothiazene can be synthesized. Many previous reports utilize benzothiazene as a monomer in pharmaceuitical applications. Yet, the polymerized form of benzothiazene has not been studied to date. Due to the inclusion of sulfur, benzothiazene undergoes ring-opening polymerization at a lower temperature than benzoxazine. Polymerization of benzothiazene forms thiol instead of hydroxyl groups, which cause the nature of hydrogen bonding to be different. Properties of newly synthesized polybenzothiazene are studied, showing comparable mechanical strength, stability, and reduced polymerization temperature.

Synthesis and polymerization of 1,3-benzothiazine and the properties of the derived polybenzothiazine

246th National Meeting (2013)

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