High‐Performance Polybenzoxazine Derived from Polyfunctional Benzoxazine Composed of an Oligonuclear Phenolic Compound Having a 4,4′‐Dimethylenebiphenyl Linker

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  • Takehiro Kawauchi
    Prof. T. Kawauchi, S. Matsumura Department of Materials Chemistry Faculty of Science and Technology Ryukoku University Oe‐cho, Seta Otsu Shiga 520–2194 Japan
  • Tsubasa Osawa
    T. Osawa, T. Mori, Prof. T. Takeichi Department of Environmental and Life Sciences Toyohashi University of Technology Tempaku‐cho Toyohashi Aichi 441–8580 Japan
  • Shunichiro Matsumura
    Prof. T. Kawauchi, S. Matsumura Department of Materials Chemistry Faculty of Science and Technology Ryukoku University Oe‐cho, Seta Otsu Shiga 520–2194 Japan
  • Takuto Mori
    T. Osawa, T. Mori, Prof. T. Takeichi Department of Environmental and Life Sciences Toyohashi University of Technology Tempaku‐cho Toyohashi Aichi 441–8580 Japan
  • Nobuyuki Furukawa
    Prof. N. Furukawa Department of Chemical and Biological Engineering Sasebo National College of Technology Okishin‐cho Sasebo Nagasaki 857–1193 Japan
  • Kazunori Ishikawa
    Dr. K. Ishikawa, Dr. K. Iwasaki Functional Chemicals R&D Laboratories Nippon Kayaku Co. Ltd. 31‐12 Shimo 3‐chome Kita‐ku Tokyo 115–8588 Japan
  • Koju Iwasaki
    Dr. K. Ishikawa, Dr. K. Iwasaki Functional Chemicals R&D Laboratories Nippon Kayaku Co. Ltd. 31‐12 Shimo 3‐chome Kita‐ku Tokyo 115–8588 Japan
  • Tsutomu Takeichi
    T. Osawa, T. Mori, Prof. T. Takeichi Department of Environmental and Life Sciences Toyohashi University of Technology Tempaku‐cho Toyohashi Aichi 441–8580 Japan

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<jats:title>Abstract</jats:title><jats:p>A novel polyfunctional benzoxazine monomer, <jats:bold>OP‐a</jats:bold>, is synthesized from aniline, formaldehyde, and an oligonuclear phenolic compound (OP) with a 4,4′‐dimethylenebiphenyl group as the phenol linker. After thermal curing of <jats:bold>OP‐a</jats:bold> up to 240 °C, a brown‐colored, transparent polybenzoxazine (<jats:bold>POP‐a</jats:bold>) film is obtained. The mechanical and thermal properties of the <jats:bold>POP‐a</jats:bold> film are investigated by tensile test, dynamic mechanical analysis (DMA), and thermogravimetric analysis (TGA). The <jats:bold>POP‐a</jats:bold> film is extremely tough compared with a typical polybenzoxazine (<jats:bold>PB‐a</jats:bold>) film. The elongation at break of the <jats:bold>POP‐a</jats:bold> film is 7.6%, which is surprisingly large for the highly cross‐linked thermoset. The high cross‐link density is suggested from the very high storage modulus (over 1 GPa) above the glass transition temperature (<jats:italic>T</jats:italic> <jats:sub>g</jats:sub>) observed by DMA. The <jats:italic>T</jats:italic> <jats:sub>g</jats:sub> of <jats:bold>POP‐a</jats:bold> is also improved significantly to <jats:italic>T</jats:italic> <jats:sub>g</jats:sub> = 223 °C, which is approximately 50 °C higher than that of <jats:bold>PB‐a</jats:bold>. Moreover, TGA reveals that the thermal stability of <jats:bold>POP‐a</jats:bold> is also enhanced.</jats:p>

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