Characterization of poly(1-methyl-1,4-butanediol-1,4-diyl/2,3,4-trihydro-5-methylfuran-2,5-diyl) prepared from natural rubber through 2D NMR spectroscopy

Authors

  • Takayuki Saito,

    1. Department of Materials Science and Technology, Faculty of Engineering, Nagaoka University of Technology, Nagaoka, Niigata 940-2188, Japan
    2. Chemicals Evaluation and Research Institute, 1600, Shimo-Takano, Sugito-Machi, Kitakatusika-Gun, Saitama, 345-0043, Japan
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  • Yoshimasa Yamamoto,

    1. Department of Materials Science and Technology, Faculty of Engineering, Nagaoka University of Technology, Nagaoka, Niigata 940-2188, Japan
    2. Center for Green-Tech Development in Asia, Nagaoka University of Technology, Nagaoka, Niigata 940-2188, Japan
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  • Seiichi Kawahara,

    Corresponding author
    1. Department of Materials Science and Technology, Faculty of Engineering, Nagaoka University of Technology, Nagaoka, Niigata 940-2188, Japan
    2. Center for Green-Tech Development in Asia, Nagaoka University of Technology, Nagaoka, Niigata 940-2188, Japan
    • Department of Materials Science and Technology, Faculty of Engineering, Nagaoka University of Technology, Nagaoka, Niigata 940-2188, Japan
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  • Yoshito Ohtake

    1. Chemicals Evaluation and Research Institute, 1600, Shimo-Takano, Sugito-Machi, Kitakatusika-Gun, Saitama, 345-0043, Japan
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Abstract

Poly(1-methyl-1,4-butanediol-1,4-diyl/2,3,4-trihydro-5-methylfuran-2,5-diyl) was prepared by epoxidation of deproteinized natural rubber with m-chloroperbenzoic acid followed by hydrolysis with sulfuric acid. Characterization of the resulting product was performed through FT-IR, 1H NMR, and 13C NMR spectroscopies. All signals appearing in the 1H and 13C NMR spectra were assigned by distortionless enhancement by polarization transfer (DEPT), quaternary carbon observation (QUAT), correlation spectroscopy (COSY), and heteronuclear multiple quantum correlation (HMQC) measurements. After proving the primary structure of the product, one pot synthesis of poly(1-methyl-1,4-butanediol-1,4-diyl/2,3,4-trihydro-5-methylfuran-2,5-diyl) from deproteinized natural rubber latex was carried out with peracetic acid and 2-propanol. The resulting product was characterized by 1H NMR spectroscopy on the basis of the assignments established in this study, and its gas permeability was measured for a practical application as a film. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011.

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