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Preparation of aqueous soluble polyamides from renewable succinic acid and citric acid as a new approach to design bio-inspired polymers

Authors

  • Man Jiang,

    1. Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang Province, China
    2. School of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang Province, China
    3. Zhejiang Provincial Key Laboratory of Alternative Technologies for Fine Chemicals, Shaoxing, Zhejiang Province, China
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  • Guangsong Chen,

    1. School of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang Province, China
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  • Ping Lu,

    1. School of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang Province, China
    2. Zhejiang Provincial Key Laboratory of Alternative Technologies for Fine Chemicals, Shaoxing, Zhejiang Province, China
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  • Jian Dong

    Corresponding author
    1. Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang Province, China
    2. School of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang Province, China
    3. Zhejiang Provincial Key Laboratory of Alternative Technologies for Fine Chemicals, Shaoxing, Zhejiang Province, China
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ABSTRACT

A novel type of aqueous soluble polyamides were prepared as renewable substitutes for ecologically benign poly(aspartic acid) by polymerization of succinic acid ester and hexamethylene diamine in the presence of citric acid ester. The copolymerization resulted in the formation of poly(amide imide) intermediates, which were hydrolyzed to aqueous solutions of polyamides. The hydrolyzed products were confirmed to be copolymers of succinamide and citramide with COOH side chains, similar to poly(aspartic acid). The polyamides showed strong chelating abilities to Ca2+ and Pb2+ metals, comparable to poly(aspartic acid). Interestingly, they also demonstrated antifreeze activities in water by reducing the ice fractions. The polyamides represent a new class of metal chelators and antifreeze protein mimics derived from succinamide and citramide. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 39807.

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