SpringerLink
Log in

Synthesis and antibacterial activity of Schiff base-pyridine quaternary ammonium salt-halamine compounds on cotton fabrics

  • Original Research
  • Published:
Cellulose Aims and scope Submit manuscript

Abstract

The incorporation of a single antimicrobial agent on textiles has been proven to be effective to enhance the antibacterial efficacy against single bacteria family. However, the daily usage of textile products face challenges from multiple microbes, i.e., bacterial, fungal, or/and viral, which threaten human’s safety and health. A “combination” of antimicrobial agents could be efficient and accessible to against several microbes at one time. In this study, a Schiff base-pyridinium quaternary ammonium salt-halamine precursor compound (E)-3-(((2,4-dioxoimidazolidin-1-yl)imino)methyl)pyridin-1-ium (4-DMPY) was synthesized and grafted onto MPTES-treated cotton fabric by thiol-ene click chemistry. The results of NRM, FTIR, Raman, EDX, XPS and SEM tests showed that 4-DMPY was synthesized and grafted onto cotton fabrics. The antibacterial test results showed that 4-DMPY had antibacterial activity against both Staphylococcus aureus and Escherichia coli. The antibacterial activity of 4-DMPY-finished cotton fabric was significantly enhanced after chlorination treatment, which could kill 98% of S. aureus and 98.9% of E. coli at a concentration of 5 g/L, confirming the enhanced synergistic effect between 4-DMPY and N-chloramine. The antimicrobial substance on the cotton fabric is non-soluble, which kills 98.4% E. coli and 98.3% S. aureus within 1 min by a direct contact. In addition, the produced fabric retained 81% and 63% of active chlorine content after 30 washes and 30 days of storage, indicating a good antimicrobial durability. Herein, we anticipate the technology can be used to enhance antibacterial function of cellulose products and thus resist the potential threats from microbes to ensure human’s health.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  • Chen Y, Wang Y, Wang Z, Wang Y, Han Y, Zhang Q, Han Q (2021) Engineering of super bactericidal cotton using pyridinium/di-N-chloramine siloxane with intensified synergism. Cellulose 28(10):6713–6725

    Article  CAS  Google Scholar 

  • Correia VG, Ferraria AM, Pinho MG, Aguiar-Ricardo A (2015) Antimicrobial contact-active oligo(2-oxazoline)s-grafted surfaces for fast water disinfection at the point-of-use. Biomacromolecules 16(12):3904–3915

    Article  CAS  PubMed  Google Scholar 

  • Dai L, Lou JF, Baek NW, Zhang X, Yuan JG, Xu J, Fan XR (2022) A rapid way of preparing switchable bacteria-killing and bacteria-releasing cellulosic material with anti-bacteria adhesion capability. Cellulose 29(9):5305–5323

    Article  CAS  Google Scholar 

  • DeForest CA, Anseth KS (2011) Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions. Nat Chem 3(12):925–931

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Demir B, Cerkez I, Worley SD, Broughton RM, Huang TS (2015) N-Halamine-modified antimicrobial polypropylene nonwoven fabrics for use against airborne bacteria. ACS Appl Mater Interfaces 7(3):1752–1757

    Article  CAS  PubMed  Google Scholar 

  • Dong A, Wang YJ, Gao Y, Gao T, Gao G (2017) Chemical Insights into Antibacterial N-Halamines. Chem Rev 117(6):4806–4862

    Article  CAS  PubMed  Google Scholar 

  • Fahs S, Rowther FB, Dennison SR, Patil-Sen Y, Warr T, Snape TJ (2014) Development of a novel, multifunctional, membrane-interactive pyridinium salt with potent anticancer activity. Bioorg Med Chem Lett 24(15):3430–3433

    Article  CAS  PubMed  Google Scholar 

  • Frolov N, Detusheva E, Fursova N, Ostashevskaya I, Vereshchagin A (2022) Microbiological evaluation of novel bis-quaternary ammonium compounds: clinical strains, biofilms, and resistance study. Pharmaceuticals (Basel) 15(5):1–12

    Article  Google Scholar 

  • Fu XR, Shen Y, Jiang X, Huang D, Yan YQ (2011) Chitosan derivatives with dual-antibacterial functional groups for antimicrobial finishing of cotton fabrics. Carbohydr Polym 85(1):221–227

    Article  CAS  Google Scholar 

  • Gutman O, Natan M, Banin E, Margel S (2014) Characterization and antibacterial properties of N-halamine-derivatized cross-linked polymethacrylamide nanoparticles. Biomaterials 35(19):5079–5087

    Article  CAS  PubMed  Google Scholar 

  • Hasan CM, Dutta D, Nguyen ANT (2022) Revisiting antibiotic resistance: mechanistic foundations to evolutionary outlook. Antibiotics-Basel 11(1):1–23

    Google Scholar 

  • Jiang QY, Jiang ZM, Ma KK, Li R, Du JM, **e ZW, Ren XH, Huang TS (2014) Development of cytocompatible antibacterial electro-spun nanofibrous composites. J Mater Sci 49(19):6734–6741

    Article  CAS  Google Scholar 

  • Kaur R, Liu S (2016) Antibacterial surface design-Contact kill. Prog Surf Sci 91(3):136–153

    Article  CAS  Google Scholar 

  • Kocer HB, Akdag A, Worley SD, Acevedo O, Broughton RM, Wu YN (2010) Mechanism of photolytic decomposition of N-Halamine antimicrobial siloxane coatings. ACS Appl Mater Interfaces 2(8):2456–2464

    Article  CAS  PubMed  Google Scholar 

  • Kocer HB, Cerkez I, Worley SD, Broughton RM, Huang TS (2011) Polymeric antimicrobial N-halamine epoxides. ACS Appl Mater Interfaces 3(8):2845–2850

    Article  CAS  PubMed  Google Scholar 

  • Li CH, Hou JJ, Huang Z, Zhao TY, **ao LH, Gao G, Harnoode C, Dong A (2015) Assessment of 2,2,6,6-tetramethyl-4-piperidinol-based amine N-halamine-labeled silica nanoparticles as potent antibiotics for deactivating bacteria. Colloid Surf B-Biointerfaces 126:106–114

    Article  CAS  Google Scholar 

  • Liu Y, Liu Y, Ren X, Huang TS (2014) Antimicrobial cotton containing N-halamine and quaternary ammonium groups by grafting copolymerization. Appl Surf Sci 296:231–236

    Article  CAS  Google Scholar 

  • Liu Y, Li J, Li L, McFarland S, Ren X, Acevedo O, Huang TS (2016) Characterization and mechanism for the protection of photolytic decomposition of N-alamine siloxane coatings by titanium dioxide. ACS Appl Mater Interfaces 8(5):3516–3523

    Article  CAS  PubMed  Google Scholar 

  • Luo J, Chen ZB, Sun YY (2006) Controlling biofilm formation with an N-halamine-based polymeric additive. J Biomed Mater Res Part A 77a(4):823–831

    Article  CAS  Google Scholar 

  • Ma KK, **e ZW, Jiang QY, Li J, Li R, Ren XH, Huang TS, Zhang KQ (2014) Cytocompatible and regenerable antimicrobial cellulose modified by N-halamine triazine ring. J Appl Polym Sci 131(16):40627

    Article  Google Scholar 

  • Mi Y, Chen Y, Tan W, Zhang J, Li Q, Guo Z (2022) The influence of bioactive glyoxylate bearing Schiff base on antifungal and antioxidant activities to chitosan quaternary ammonium salts. Carbohydr Polym 278:118970

    Article  CAS  PubMed  Google Scholar 

  • Morais DS, Guedes RM, Lopes MA (2016) Antimicrobial approaches for textiles: from research to market. Materials 9(6):498

    Article  PubMed  PubMed Central  Google Scholar 

  • Pernak J, Kalewska J, Ksycinska H, Cybulski J (2001) Synthesis and anti-microbial activities of some pyridinium salts with alkoxymethyl hydrophobic group. Eur J Med Chem 36(11–12):899–907

    Article  CAS  PubMed  Google Scholar 

  • Ren X, Akdag A, Kocer HB, Worley SD, Broughton RM, Huang TS (2009) N-Halamine-coated cotton for antimicrobial and detoxification applications. Carbohydr Polym 78(2):220–226

    Article  CAS  Google Scholar 

  • Rong L, Liu H, Wang B, Mao Z, Xu H, Zhang L, Zhong Y, Feng X, Sui X (2019) Durable antibacterial and hydrophobic cotton fabrics utilizing enamine bonds. Carbohydr Polym 211:173–180

    Article  CAS  PubMed  Google Scholar 

  • Sohrabi C, Alsafi Z, O’Neill N, Khan M, Kerwan A, Al-Jabir A, Iosifidis C, Agha R (2020) World health organization declares global emergency: a review of the 2019 novel coronavirus (COVID-19). Int J Surg 76:71–76

    Article  PubMed  PubMed Central  Google Scholar 

  • Tan K, Obendorf SK (2007) Fabrication and evaluation of electrospun nanofibrous antimicrobial nylon 6 membranes. J Membr Sci 305(1–2):287–298

    Article  CAS  Google Scholar 

  • Wang P, Zhang MY, Qu JH, Wang LJ, Geng JZ, Fu FY, Liu XD (2022) Antibacterial cotton fabric prepared by a grafting to strategy using a QAC copolymer. Cellulose 29(6):3569–3581

    Article  CAS  Google Scholar 

  • Wen W, Zhang Z, **g L, Zhang T (2020) Synthesis of a Hein–Schiff base compound and its antibacterial activity on cotton fabrics. Cellulose 27(12):7243–7254

    Article  CAS  Google Scholar 

  • Wen W, Zhang ZX, **g LX, Zhang TH (2021) Highly antibacterial efficacy of a cotton fabric treated with Piperazinyl Schiff Base. Fibers Polym 22(12):3298–3308

    Article  CAS  Google Scholar 

  • ** WX, Scott TF, Kloxin CJ, Bowman CN (2014) Click chemistry in materials science. Adv Funct Mater 24(18):2572–2590

    Article  CAS  Google Scholar 

  • Xue Y, **ao H (2015) Antibacterial/Antiviral property and mechanism of dual-functional quaternized pyridinium-type copolymer. Polymers 7(11):2290–2303

    Article  CAS  Google Scholar 

  • Zeng MH, Xu JY, Luo Q, Hou CX, Qiao SP, Fu S, Fan XT, Liu JQ (2020) Constructing antibacterial polymer nanocapsules based on pyridine quaternary ammonium salt. Mater Sci Eng C-Mater Biol Appl 108:110383

    Article  CAS  PubMed  Google Scholar 

  • Zhang B, Jiao Y, Kang Z, Ma K, Ren X, Liang J (2013) Durable antimicrobial cotton fabrics containing stable quaternarized N-halamine groups. Cellulose 20(6):3067–3077

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Prof. Zaixing Zhang and Lingxiao **g contributed equally to this work as co-corresponding authors.

Funding

This work was supported by the Jiangsu Province Social development Projects (Key R & D Projects), (BE2022777). This research was also supported by Autonomous Region Science and Technology Support **njiang Project Plan (2022E02018).

Author information

Authors and Affiliations

  1. College of Sericulture, Textiles and Biomass Sciences, Chongqing Biomass Fiber Materials and Modern Textile Engineering Technology Research Center, State Key Laboratory of Silkworm Genome Biology, Southwest University, Chongqing, 400715, China

    **n Tang, Lingxiao **g & Tonghua Zhang

  2. Chemistry and Material Engineering, School of Huaihua University, Huaihua, 418008, China

    Zaixing Zhang & Sha Zhou

  3. Jiangsu Ruilante New Materials Co., Ltd., Yangzhou, 211400, China

    Zaixing Zhang

  4. State Key Lab of High Performance Ceramics and Superfine Microstructures, Shanghai Institute of Ceramics, Shanghai, 200050, China

    Kun Luan

Authors
  1. **n Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zaixing Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lingxiao **g
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kun Luan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sha Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tonghua Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

XT: Conceptualization, Writing—Original Draft; ZZ: Conceptualization, Writing—Review & Editing, Supervision; LJ: Conceptualization, Writing—Review & Editing, Supervision; KL: Writing—Review; SZ: Investigation; TZ: Conceptualization, Writing—Review & Editing.

Corresponding author

Correspondence to Lingxiao **g.

Ethics declarations

Competing interests

The authors declare no competing interests.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors. In this experiment, we did not collect any samples of humans and animals.

Consent to participate

Not applicable.

Consent for publication

Not applicable.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tang, X., Zhang, Z., **g, L. et al. Synthesis and antibacterial activity of Schiff base-pyridine quaternary ammonium salt-halamine compounds on cotton fabrics. Cellulose 30, 10519–10531 (2023). https://doi.org/10.1007/s10570-023-05510-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-023-05510-3

Keywords

Search

Navigation