Highly cross-linked thermosetting benzocyclobutene-modified bis-benzoxazine resins from 4-hydroxybenzocyclobutene

In the present study, benzocyclobutene (BCB) was incorporated into the benzoxazine (BOZ) monomers. BCB-functionalized BOZ monomers were synthesized by the reaction of 4-hydroxybenzocyclobutene, aromatic diamine, and paraformaldehyde in dioxane under reflux. The structure of the monomers was characterized by Fourier transform infrared spectroscopy (FTIR) and proton and carbon nuclear magnetic resonance spectroscopies. The monomers possess two kinds of ring-opening polymerizable functional groups, BCB and BOZ. Differential scanning calorimetry and FTIR were used to study the polymerization behavior of the monomers. Dynamic mechanical analysis demonstrates that the related polymers show high storage moduli maintained in a wide range of temperature up to 300°C and high glass transition temperature at about 330°C. The incorporation of BCB improved the thermal stability and mechanical property of the monomer.