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Synthesis of O-(2,3-dihydroxypropyl) cellulose in NaOH/urea aqueous solution: As a precursor for introducing “necklace-like” structure

Authors

  • Chunyu Chang,

    1. Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto, Japan
    2. Guangzhou Sugarcane Industry Research Institute, Guangzhou, China
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  • Yoshikuni Teramoto,

    1. Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto, Japan
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  • Yoshiyuki Nishio

    Corresponding author
    • Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto, Japan
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Correspondence to: Y. Nishio (Email: ynishio@kais.kyoto-u.ac.jp)

ABSTRACT

O-(2,3-dihydroxypropyl) cellulose (DHPC) samples were synthesized by etherification of cellulose with glycidol (GLY) in a NaOH/urea aqueous solution system under different reaction conditions, so that they had different degrees of ether substitution (DS) in both the overall and regional distributions. The characterization was made by NMR spectroscopy in order to clarify the effects of the molar ratio of in-fed GLY to anhydroglucose unit and of the reaction temperature not only on the total and regional DSs but also on the molar substitution (MSdhp) for the multireactive dihydroxypropyl group. The evaluation of MSdhp was performed after complete propionylation of each DHPC sample. Determination of molecular weights was also conducted on the propionylated DHPCs by GPC analysis. As a preliminary extension, butyralization of DHPC was undertaken in aqueous solution by using p-toluenesulfonic acid as catalyst together with butyraldehyde (BuA). Two-dimensional NMR (1H–13C gHSQC) spectra measurements revealed that the products contained butyral groups, owing to dehydration-cyclization between the BuA-carbonyl and the duplicate hydroxyls in the side chain of DHPC. Such butyral derivatives of cellulose are expected to be a promising functional material parallel or superior to poly(vinyl butyral) available for safety glass interlayers, etc. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3590–3597

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