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Michael reaction of chitosan with acrylamides in an aqueous alkali–urea solution

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Abstract

Michael reaction of chitosan with acryl reagents in acidic media is a facile method to introduce functional groups; however, when acrylamide (AAm) is used only a low degree of substitution was achieved. Here, the reaction was carried out in a new solvent, aqueous LiOH/urea solution. In the alkaline media, hydroxyl groups at the C-6 position, instead of amino groups at the C-2 position, act as Michael donor. The introduced amide groups continue to hydrolyze to give carboxylate groups. The reaction is faster, and the total degree of substitution is higher than the one achieved in acidic media, despite that the reaction temperature is lower and the reaction time is shorter. The total degree of substitution and hydrolysis percentage increases with increasing reaction time and elevated temperature. Increasing the feeding molar ratio of AAm to chitosan increases the total degree of substitution, but reduces hydrolysis percentage.

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Article Open access 02 December 2021

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Acknowledgments

We thank the financial support for this work from the National Natural Science Foundation of China (Grants Nos. 21174070, 21274068, 21228401 and 21374048), Tianjin Public Health Bureau (13KG110), Program for New Century Excellent Talents in University (NCET-11-0264), and PCSIRT program (IRT1257).

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Authors and Affiliations

  1. State Key Laboratory of Medicinal Chemical Biology and Key Laboratory of Functional Polymer Materials, The Co-Innovation Center of Chemistry and Chemical Engineering of Tianjin, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, China

    Chong Li, Qiuyan Han, Ying Guan & Yongjun Zhang

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  1. Chong Li
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  2. Qiuyan Han
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  3. Ying Guan
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  4. Yongjun Zhang
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Correspondence to Yongjun Zhang.

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Li, C., Han, Q., Guan, Y. et al. Michael reaction of chitosan with acrylamides in an aqueous alkali–urea solution. Polym. Bull. 72, 2075–2087 (2015). https://doi.org/10.1007/s00289-015-1390-8

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  • DOI: https://doi.org/10.1007/s00289-015-1390-8

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