Skip to main content
SpringerLink
Log in

Enhancing antibacterial and flame-retardant performance of cotton fabric with an iminodiacetic acid-containing N-halamine

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

Abstract

This research focused on preparing antibacterial and flame-retardant multifunctional cotton fabric to decrease the threat of harmful microorganism and fire, which might have huge potential application in household textiles. A water-soluble N-halamine precursor based on s-triazine (TIAPC) was synthesized by introducing iminodiacetic acid (IDA), which can chelate with metal ions to obtain flame retardancy. After coating with TIAPC, the cotton fabric was chlorinated in dilute bleach solution and chelated in metal salt solution to achieve antibacterial and flame-retardant properties. The surface morphology and chemical state of TIAPC-coated cotton fabric were characterized by FT-IR, XPS, SEM and EDX. The chlorinated TIAPC-coated cotton fabric displayed high-efficacy and rapid bactericidal effect against S. aureus and E. coli O157: H7 with 100% bacterial reduction in 1 min. Meanwhile, the chelated TIAPC-modified cotton fabric presented good thermal stability and char-forming capability. The hydrophobic property of modified cotton fabric was greatly improved after chlorination. Besides, this multifunctional coating had little effect on the cytotoxicity, tensile strength, air permeability, whiteness and drape of cotton fabric.

Graphic abstract

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

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

  • Acikel SM, Senay RH, Akgol S, Aslan A (2017) Removal of acid black 210 dye from leather dyeing effluent using spherical particles of P(HEMA-GMA)IDA-Cr(III) hydrogel membrane. J Soc Leather Technol Chem 101:135–142

    CAS  Google Scholar 

  • Ahmed AI, Hay JN, Bushell ME, Wardell JN, Cavalli G (2009) Optimizing halogenation conditions of N-halamine polymers and investigating mode of bactericidal action. J Appl Polym Sci 113:2404–2412

    CAS  Google Scholar 

  • Bai R, Zhang Q, Li L, Li P, Wang YJ, Simalou O, Dong A (2016) N-Halamine-Containing electrospun fibers kill bacteria via a contact/release co-determined antibacterial pathway. ACS Appl Mater Int 8:31530–31540

    CAS  Google Scholar 

  • Cerkez I, Kocer HB, Worley SD, Broughton RM, Huang TS (2012) N-halamine copolymers for biocidal coatings. React Funct Polym 72:673–679

    CAS  Google Scholar 

  • Chen H, Li Q, Wang M, Ji D, Tan W (2020a) XPS and two-dimensional FTIR correlation analysis on the binding characteristics of humic acid onto kaolinite surface. Sci Total Environ 724:138154

    CAS  PubMed  Google Scholar 

  • Chen W, Zhu Y, Zhang Z, Gao Y, Liu W, Borjihan Q, Dong A (2020b) Engineering a multifunctional N-halamine-based antibacterial hydrogel using a super-convenient strategy for infected skin defect therapy. Chem Eng J 379:122238

    CAS  Google Scholar 

  • Demir B, Broughton RM, Qiao M, Huang TS, Worley SD (2017) N-halamine biocidal materials with superior antimicrobial efficacies for wound dressings. Molecules 22(10):1582

    PubMed Central  Google Scholar 

  • El-Nahhal IM, Zaggout FR, Nassar MA, El-Ashgar NM, Maquet J, Babonneau F, Chehimi MM (2003) Synthesis, characterization and applications of immobilized iminodiacetic acid-modified silica. J Sol-Gel Sci Technol 28(2):255–265

    CAS  Google Scholar 

  • Hanshaw RG, Stahelin RV, Smith BD (2008) Noncovalent keystone interactions controlling biomembrane structure. Chem-Eur J 14(6):1690–1697

    CAS  PubMed  Google Scholar 

  • Hisaki I, Sasaki T, Tohnai N, Miyata M (2012) Supramolecular-tilt-chirality on twofold helical assemblies. Chem-Eur J 18(33):10066–10073

    CAS  PubMed  Google Scholar 

  • Huang Y, Zhu Q, Sheng T, Hu S, Fu R, Shen C, Wu X (2013) Lanthanide coordination polymers assembled from triazine-based flexible polycarboxylate ligands and their luminescent properties. CrystEngComm 15(18):3560–3567

    CAS  Google Scholar 

  • Jahangiri A, Ghoreishian SM, Akbari A, Norouzi M, Ghasemi M, Ghoreishian M, Shafiabadi E (2018) Natural dyeing of wool by madder (Rubia tinctorum L.) root extract using tannin-based biomordants: colorimetric, fastness and tensile assay. Fiber Polym 19(10):2139–2184

    CAS  Google Scholar 

  • Jiang Z, Ma K, Du J, Li R, Ren X, Huang TS (2014) Synthesis of novel reactive N-halamine precursors and application in antimicrobial cellulose. Appl Surf Sci 288:518–523

    CAS  Google Scholar 

  • Kagarise RE (1955) Spectroscopic studies on the soaps of phenylstearic acid. I. Infrared absorption spectra and the hydrolysis of soap films. J Phys Chem 59(3):196–205

    Google Scholar 

  • Kang ZZ, Zhang B, Jiao YC, Xu YH, He QZ, Liang J (2013) High-efficacy antimicrobial cellulose grafted by a novel quaternarized N-halamine. Cellulose 20(2):885–893

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  • Lai X, Zeng X, Li H, Liao F, Yin C, Zhang H (2012) Synergistic effect between a triazine-based macromolecule and melamine pyrophosphate in flame retardant polypropylene. Polym Compos 33(1):35–43

    CAS  Google Scholar 

  • Li S, Lin X, Liu Y, Li R, Ren X, Huang TS (2019) Phosphorus-nitrogen-silicon-based assembly multilayer coating for the preparation of flame retardant and antimicrobial cotton fabric. Cellulose 26(6):4213–4223

    CAS  Google Scholar 

  • Ma K, Liu Y, Xie Z, Li R, Jiang Z, Ren X, Huang TS (2013) Synthesis of novel N-halamine epoxide based on cyanuric acid and its application for antimicrobial finishing. Ind Eng Chem Res 52(22):7413–7418

    CAS  Google Scholar 

  • Mazik M, Cavga H (2006) Carboxylate-based receptors for the recognition of carbohydrates in organic and aqueous media. J Organ Chem 71(8):2957–2963

    CAS  Google Scholar 

  • Mu T, Pan N, Wang Y, Ren X, Huang TS (2018) Antibacterial coating of cellulose by Iso-bifunctional reactive N-halamine with the dyeing process of reactive dye. Fiber Polym 19(11):2284–2289

    CAS  Google Scholar 

  • Omer AM, Elgarhy GS, El-Subruiti GM, Khalifa RE, Eltaweil AS (2020) Fabrication of novel iminodiacetic acid-functionalized carboxymethyl cellulose microbeads for efficient removal of cationic crystal violet dye from aqueous solutions. Int J Biol Macromol 148:1072–1083

    CAS  PubMed  Google Scholar 

  • Pan Y, Wang W, Liu L, Ge H, Song L, Hu Y (2017) Influences of metal ions crosslinked alginate based coatings on thermal stability and fire resistance of cotton fabrics. Carbohydr Polym 170:133–139

    CAS  PubMed  Google Scholar 

  • Razak MR, Yusof NA, Haron MJ, Ibrahim N, Mohammad F, Kamaruzaman S, Al-Lohedan HA (2018) Iminodiacetic acid modified kenaf fiber for waste water treatment. Int J Biol Macromol 112:754–760

    CAS  PubMed  Google Scholar 

  • Ren X, Kou L, Liang J, Worley SD, Tzou YM, Huang TS (2008) Antimicrobial efficacy and light stability of N-halamine siloxanes bound to cotton. Cellulose 15(4):593–598

    CAS  Google Scholar 

  • Ren X, Kou L, Kocer HB, Worley SD, Broughton RM, Tzou YM, Huang TS (2009) Antimicrobial modification of polyester by admicellar polymerization. J Biomed Mater Res B 89(2):475–480

    Google Scholar 

  • Richards GN, Zheng G (1991) Influence of metal ions and of salts on products from pyrolysis of wood: applications to thermochemical processing of newsprint and biomass. J Anal Appl Pyrol 21(1–2):133–146

    CAS  Google Scholar 

  • Shi R, Tan L, Zong L, Ji Q, Li X, Zhang K, Xia Y (2017) Influence of Na+ and Ca2+ on flame retardancy, thermal degradation, and pyrolysis behavior of cellulose fibers. Carbohydr Polym 157:1594–1603

    CAS  PubMed  Google Scholar 

  • Sosa GL, Zalts A, Ramirez SA (2016) Complexing capacity of electroplating rinsing baths-a twist to the resolution of two ligand families of similar strength. J Anal Sci Technol. https://doi.org/10.1186/s40543-016-0088-3

    Article  Google Scholar 

  • Sun G, Xu XJ, Bickett JR, Williams JF (2001) Durable and regenerable antibacterial finishing of fabrics with a new hydantoin derivative. Ind Eng Chem Res 40(4):1016–1021

    CAS  Google Scholar 

  • Sun Y, Sun G (2002) Durable and regenerable antimicrobial textile materials prepared by a continuous grafting process. J Appl Polym Sci 84(8):1592–1599

    CAS  Google Scholar 

  • Tian H, Zhai Y, Xu C, Liang J (2017) Durable antibacterial cotton fabrics containing stable acyclic N-halamine groups. Ind Eng Chem Res 56(28):7902–7909

    CAS  Google Scholar 

  • Viola MN, Ikram M, Rehman S, Ali S, Akhtar MN, Aidamen MA, Schulzke C (2019) A paddle wheel dinuclear Copper(II) carboxylate: crystal structure, thermokinetic and magnetic properties. J Mol Struct 1196:754–759

    CAS  Google Scholar 

  • Wang X, Xu M, Zhang Z, Leng Y, Li B (2018) Synthesis of a novel N-alkoxyamine containing compound and its application as an effective flame retardant for polypropylene film by quenching free radical. J Anal Appl Pyrol 134:243–253

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  • Worley SD, Chen Y, Wang JW, Wu R (2005) Novel N-halamine siloxane monomers and polymers for preparing biocidal coatings. Surf Coat Int B 88(2):93–99

    CAS  Google Scholar 

  • Xu D, Ma X, Zhu P, Jiang Z (2020) A novel durable and water-soluble N-halamine precursor for antibacterial cellulose fabrics. AATCC J Res 7(3):34–41

    CAS  Google Scholar 

  • Yin M, Wang Y, Zhang Y, Ren X, Qiu Y, Huang TS (2020) Novel quaternarized N-halamine chitosan and polyvinyl alcohol nanofibrous membranes as hemostatic materials with excellent antibacterial properties. Carbohydr Polym 232:115823

    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

    CAS  Google Scholar 

  • Zhang K, Zong L, Tan Y, Ji Q, Yun W, Shi R, Xia Y (2016) Improve the flame retardancy of cellulose fibers by grafting zinc ion. Carbohydr Polym 136:121–127

    CAS  PubMed  Google Scholar 

  • Zhang Y, Zhu L, Wang Y, Lou Z, Shan W, Xiong Y, Fan Y (2018) Preparation of a biomass adsorbent for gallium(III) based on corn stalk modified by iminodiacetic acid. J Taiwan Inst Chem E 91:291–298

    CAS  Google Scholar 

  • Zhang S, Demir B, Ren X, Worley SD, Broughton RM, Huang TS (2019) Synthesis of antibacterial N-halamine acryl acid copolymers and their application onto cotton. Appl Polym Sci 136(16):47426

    Google Scholar 

  • Zhou X, Zhou J, Liu Y, Guo J, Ren J, Zhou F (2018) Preparation of iminodiacetic acid-modified magnetic biochar by carbonization, magnetization and functional modification for Cd(II) removal in water. Fuel 233:469–479

    CAS  Google Scholar 

  • Zhu FL, Li X, Feng QQ (2020) Thermal decomposed behavior and kinetic study for untreated and flame retardant treated regenerated cellulose fibers using thermogravimetric analysis. J Therm Anal Calorim. https://doi.org/10.1007/s10973-020-09780-y

    Article  Google Scholar 

Download references

Acknowledgments

The authors would like to thank the National Natural Science Foundation of China (51703101, 51991354).

Author information

Authors and Affiliations

  1. Institute of Functional Textiles and Advanced Materials, College of Textile and Clothing, State Key Laboratory of Bio-Fibers and Eco-Textiles, Qingdao University, Qingdao, 266071, China

    Denghui Xu, Shijie Wang, Jiewen Hu, Yun Liu, Zhiming Jiang & Ping Zhu

Authors
  1. Denghui Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shijie Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jiewen Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yun Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhiming Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ping Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Zhiming Jiang or Ping Zhu.

Ethics declarations

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file 1 (DOCX 1451 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xu, D., Wang, S., Hu, J. et al. Enhancing antibacterial and flame-retardant performance of cotton fabric with an iminodiacetic acid-containing N-halamine. Cellulose 28, 3265–3277 (2021). https://doi.org/10.1007/s10570-021-03716-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-021-03716-x

Keywords

Search

Navigation