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Engineering of super bactericidal cotton using pyridinium/di-N-chloramine siloxane with intensified synergism

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Abstract

Tuning the ratio of complementary biocidal groups in a composite unit is proved to be a tactic to better minimize their weaknesses to realize higher synergism. A silane with precursors of one pyridinium and two N-chloramine sites, 6-(pyridin-4-yl)-3-(3-(trimethoxysilyl)propyl)-1,3,5-triazinane-2,4-dione, was synthesized, hydrolyzed and dehydrocondensed into a silicone modifier on cotton cellulose. Specially, isonicotinaldehyde was ammonolyzed with biuret to produce 6-(pyridin-4-yl)-1,3,5-triazinane-2,4-dione that subsequently reacted with (γ-chloropropyl)trimethoxysilane to synthesize the silane through nucleophilic substitution. The modifier on cotton was quaternized and chlorinated to transform the one pyridine and two amide N–H structures in each unit of the silicone to pyridinium and N-chloramine counterparts. The cationic pyridinium increases the hydrophilicity of the unit and draws anionic bacteria to its two adjacent highly fatal N-chloramine sites, achieving a faster contact-killing rate than not only monofunctionality but also basic synergistic integration of one cationic center and one N-chloramine. This phenomenon is therefore referred to as “intensified synergism” and provides crucial information for the design of more powerful biocides. The pyridinium/di-N-chloramine silicone coating exhibited extraordinary durability towards UV irradiation, washing cycles and long-term storage due to the good UV resistance and chemical inertness of pyridinium and silicone backbone.

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Acknowledgments

This work was supported by the Natural Science Foundation of Shandong Province [Grant No. ZR2020ME083].

Funding

This work was supported by the Natural Science Foundation of Shandong Province [Grant No. ZR2020ME083].

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Authors and Affiliations

  1. Department of Applied Chemistry, College of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao, 266590, People’s Republic of China

    Yong Chen, Yuyu Wang, Zhendong Wang, Yuwen Wang & Yanjie Han

  2. Analytical and Testing Center, School of Materials Science and Engineering, Shandong University of Science and Technology, Qingdao, 266590, People’s Republic of China

    Qiang Zhang

  3. Department of Biological Engineering, College of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao, 266590, People’s Republic of China

    Qiuxia Han

Authors
  1. Yong Chen
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  2. Yuyu Wang
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  4. Yuwen Wang
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  5. Yanjie Han
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  6. Qiang Zhang
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Contributions

Conceptualization, Methodology, Writing- Reviewing and Editing, Supervision, Funding acquisition: Yong Chen. Investigation and Visualization: Yuyu Wang. Investigation: Zhendong Wang. Investigation: Yuwen Wang. Investigation: Yanjie Han. Formal analysis: Qiang Zhang. Investigation, writing and resources: Qiuxia Han.

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Correspondence to Yong Chen or Qiuxia Han.

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Chen, Y., Wang, Y., Wang, Z. et al. Engineering of super bactericidal cotton using pyridinium/di-N-chloramine siloxane with intensified synergism. Cellulose 28, 6713–6725 (2021). https://doi.org/10.1007/s10570-021-03947-y

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