LAUSR

A fluorine-containing difunctional benzoxazine is synthesized by hydrosilylation of a monofunctional benzoxazine based on o-allylphenol and p-fluoroaniline. Besides the intramolecular and intermolecular hydrogen bonding associated with the nitrogen and oxygen atoms in the oxazine ring, specific self-complementary intermolecular ArF···HO hydrogen bonding is formed in the polymerization of the benzoxazine, which leads to the resultant polybenzoxazine possessing a broad glass transition temperature range and showing two not well-separated transitions. Based on the two glass transition temperatures, the polybenzoxazine exhibits triple-shape-memory behaviors by manipulating temperature and strain in the shape fixing process under tensile and bending modes. The dynamic mechanical and shape-memory properties of the polybenzoxazine are influenced by the combined effect of the cross-linking density and the ArF···HO hydrogen bonding.