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N-glycosylation approach to glucose-functionalized diamine and its use for protection-free synthesis of polyurea bearing glucoside pendant

Authors

  • Atsushi Sudo,

    Corresponding author
    1. Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae 3-4-1, Higashi-Osaka, Osaka 577-8502, Japan
    • Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae 3-4-1, Higashi-Osaka, Osaka 577-8502, Japan
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  • Shou Sugita

    1. Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae 3-4-1, Higashi-Osaka, Osaka 577-8502, Japan
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Abstract

A glucose-functionalized diamine was prepared and used as a new monomer for polyurea synthesis. The diamine was prepared by N-glycosylation of 1,6-hexamethylenediamine with D-glucose. Upon adding diisocyanates to the diamine, isocyanate reacted selectively with the amino groups, not with the hydroxyl groups of the glucose-derived structure, to give the corresponding polyureas. The polyureas exhibited highly hydrophilic nature due to the presence of the glucose-derived side chain. A ternary system consisting of the glucose-functionalized diamine, piperazine, and diisocyanate gave the corresponding polyureas, where content of the glucose-derived moiety was tunable by feed ratio between the diamine and piperazine. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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