Design, Synthesis, Characterization, and Polymerization of Fused-Ring Naphthoxazine Resins

Fused-ring naphthoxazine monomers are synthesized from 1-naphthols and cycloimines derived from piperidine and pyrrolidine. Their polymerization has been confirmed by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and Fourier transform infrared spectroscopy (FT-IR) as well as by solution and solid-state 1H and 13C nuclear magnetic resonance spectroscopy (NMR). A polymerization reaction similar to the traditional benzoxazine monomers is found with oxazine ring disappearing and hydroxyl group forming by the nonisothermal FT-IR experiment. Fused-ring monomers, studied in this work, polymerize at significantly lower temperatures compared to the ordinary benzoxazine resins.Fil: Arza, Carlos R.. Case Western Reserve University; Estados UnidosFil: Froimowicz, Pablo. Case Western Reserve University; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología en Polímeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología en Polímeros y Nanotecnología; ArgentinaFil: Han, Lu. Case Western Reserve University; Estados UnidosFil: Graf, Robert. Max Planck Institute For Polymer Research; AlemaniaFil: Ishida, Hatsuo. Case Western Reserve University; Estados Unido