Synthesis of Schiff base–containing benzoxazine derivatives

ABSTRACT The excellent chemical and physical properties of benzoxazine resins and the functionality of Schiff bases were combined in one compound's structure, creating newly designed benzoxazine derivatives that can form complexes with metals. The new type of benzoxazine monomer was synthesized via the ring‐closure reaction of formaldehyde, aniline, and three newly designed Schiff bases. The presence of the Schiff base in the molecular structure of these novel benzoxazine monomers enables them to trap metals as the functional compounds, like Cu, from a solution. Thermally initiated polymerization occurs at a lower temperature by the formation of intermolecular and intramolecular hydrogen bonds between imine, oxazine, Schiff base hydroxyl groups, and the newly generated hydroxyl groups. The thermal behavior of the bisbenzoxazine monomers was investigated with Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), and differential scanning calorimetry, and then they were cured at 120, 180, and 230°C. According to the magnetic susceptibility, FTIR, scanning electron microscopy with energy dispersive X‐ray spectroscopy, TGA, and microwave plasma atomic emission spectroscopy results, it is shown that Cu(II) complexes of the compounds were also succesfully synthesized, and they proved to be successful in catching metal. This is due to the functionality of Schiff bases forming the metal complexation in the compounds. The poly(bisbenzoxazine)s also showed high limiting oxygen index (31–37), low ring‐opening temperature (150–190°C), high char yield (35%–49%), and excellent thermal stability, due to the highly crosslinked nature of the polymers. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136 , 47908.