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Synthesis and thermoreversible gelation of diblock methylcellulose analogues via Huisgen 1,3-dipolar cycloaddition

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Abstract

A novel synthetic method to link acetylated cellulose derivatives with methylated cellulose derivatives via Huisgen 1,3-dipolar cycloaddition was developed to produce 1,2,3-triazole-linked diblock copolymers consisting of hydrophilic cellobiose or low-molecular-weight cellulose and a hydrophobic 2,3,6-tri-O-methyl-cellulose. Huisgen 1,3-dipolar cycloaddition had the advantage over glycosylation reaction of being able to connect a hydrophilic block having higher molecular weight than cellobiose with a hydrophobic 2,3,6-tri-O-methyl-cellulose block. As a consequence, 2.0 wt% aqueous solutions of the 1,2,3-triazole-linked diblock methylcellulose analogues exhibited the thermoreversible gelation in water at around 25 °C as same as that of β-(1 → 4)-linked diblock methylcellulose. Differential scanning calorimetry measurements of 2.0 wt% aqueous solutions of the diblock copolymers revealed that an important structural factor for its thermoreversible gelation was not a β-(1 → 4)-glycosidic linkage between hydrophilic and hydrophobic blocks of diblock methylcellulose, but a sequence of anhydro 2,3,6-tri-O-methyl-glucopyranosyl units and that of unmodified glucopyranosyl ones.

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Acknowledgments

This investigation was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, and Culture of Japan (Nos. 18680009 and 21580205).

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Authors and Affiliations

  1. Graduate School of Agriculture, Kyoto University, Kitashirakawa-Oiwake-cho, Sakyo-ku, Kyoto, 606-8502, Japan

    Atsushi Nakagawa, Hiroshi Kamitakahara & Toshiyuki Takano

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  1. Atsushi Nakagawa
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  2. Hiroshi Kamitakahara
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  3. Toshiyuki Takano
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Correspondence to Hiroshi Kamitakahara.

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Nakagawa, A., Kamitakahara, H. & Takano, T. Synthesis and thermoreversible gelation of diblock methylcellulose analogues via Huisgen 1,3-dipolar cycloaddition. Cellulose 19, 1315–1326 (2012). https://doi.org/10.1007/s10570-012-9703-7

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  • DOI: https://doi.org/10.1007/s10570-012-9703-7

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