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Synthesis, characterization, and thermal properties of alkyl-functional naphthoxazines

Authors

  • Tamer Uyar,

    Corresponding author
    1. Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio 44106
    2. UNAM-Institute of Materials Science & Nanotechnology, Bilkent University, Ankara 06800, Turkey
    • Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio 44106
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  • Jale Hacaloglu,

    1. Department of Chemistry, Middle East Technical University, Ankara 06531, Turkey
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  • Hatsuo Ishida

    Corresponding author
    1. Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio 44106
    • Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio 44106
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Abstract

A series of alkyl-functional naphthoxazine resins having various alkyl chain lengths from C1 to C18 are synthesized with a high yield and high purity by the reactions of 1,5-dihydroxynaphthalene, formaldehyde, and aliphatic amines. The proposed chemical structures of the naphthoxazines are confirmed by high-resolution mass spectrometry, 1H nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and pyrolysis mass spectrometry studies. The alkyl-functional naphthoxazines have shown low polymerization temperature characteristics where polymerization of these monomers is achieved in the range of 150–170°C yielding cross-linked polynaphthoxazines. The low-temperature polymerization characteristics and the associated thermal degradation behaviors are studied. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013

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