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Antibacterial finishing of cotton fabrics based on thiol-maleimide click chemistry

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Abstract

Cotton fabrics with durable antibacterial properties were prepared by a novel method of thiol-maleimide click reaction. Firstly, 3-Mercaptopropyltriethoxysilane was utilized as a modifier to generate thiol groups on the cotton surface. Then, these thiol groups reacted with N-phenyl-male-imide through thiol-maleimide click chemistry. The surface morphology of the treated fabrics and the reaction mechanism were characterized by FT-IR, Raman, EDS, XPS and SEM. Antibacterial activities, mechanical properties and thermal performance of treated cotton fabrics were also investigated. The Escherichia coli antibacterial rate of treated cotton was 99.56% and the Staphylococcus aureus antibacterial rate of treated cotton was 98.91%, with only a slight decrease after 10 cycles of standard washing, to 88.69 and 87.66%, respectively. These results demonstrated that this treatment effectively endowed cotton fabrics with durable antibacterial properties due to the chemical bonding formed between the antibacterial agent and the substrate. In addition, the treated cotton fabrics maintained good mechanical properties and thermal stability.

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References

  • Baldwin AD, Kiick KL (2011) Tunable degradation of maleimide-thiol adducts in reducing environments. Bioconjugate Chem 22:1946–1953. https://doi.org/10.1021/bc200148v

    Article  CAS  Google Scholar 

  • Bashar MM, Khan MA (2013) An overview on surface modification of cotton fiber for apparel use. J Polym Environ 21:181–190

    Article  Google Scholar 

  • Belbekhouche S, Guerrouache M, Carbonnier B (2016) Thiol-maleimide michael addition click reaction: a new route to surface modification of porous polymeric monolith. Macromol Chem Phys 217:997–1006. https://doi.org/10.1002/macp.201500427

    Article  CAS  Google Scholar 

  • Billiet L, Gok O, Dove AP et al (2011) Metal-free functionalization of linear polyurethanes by thiol-maleimide coupling reactions. Macromolecules 44:7874–7878. https://doi.org/10.1021/ma201323g

    Article  CAS  Google Scholar 

  • Csw B, Al-Azzawi AM, Mahdi SAR et al (2013) Synthesis and evaluation of antimicrobial activity of several new maleimides to benzothiazole moiety. Baghdad Sci J 10:658–672

    Google Scholar 

  • El Shafei A, Abou-Okeil A (2011) ZnO/carboxymethyl chitosan bionano-composite to impart antiacterial and UV protection for cotton fabric. Carbohydr Polym 83:920–925. https://doi.org/10.1016/j.carbpol.2010.08.083

    Article  CAS  Google Scholar 

  • Gargoubi S, Tolouei R, Chevallier P, Levesque L, Ladhari N, Boudokhane C, Mantovani D (2016) Enhancing the functionality of cotton fabric by physical and chemical pre-treatments: a comparative study. Carbohydr Polym 147:28

    Article  CAS  Google Scholar 

  • Gokmen MT, Brassinne J, Prasath RA, Du Prez FE (2011) Revealing the nature of thio-click reactions on the solid phase. Chem Commun (Camb) 47:4652–4654. https://doi.org/10.1039/c0cc05340f

    Article  CAS  Google Scholar 

  • Hassan MS, Ali HE, Ali NM (2017) Antibacterial activity of cotton fabrics treated with poly (vinyl alcohol)/ZnO nanocomposites, photocatalyzed by UV irradiation. J Vinyl Addit Technol 23:E34–E39. https://doi.org/10.1002/vnl.21593

    Article  CAS  Google Scholar 

  • He X, Tao R, Zhou T, Wang C, Xie K (2014) Structure and properties of cotton fabrics treated with functionalized dialdehyde chitosan. Carbohydr Polym 103:558–565

    Article  CAS  Google Scholar 

  • Huang Z et al (2017) Combining orthogonal chain-end deprotections and thiol-maleimide michael coupling: engineering discrete oligomers by an iterative growth strategy. Angew Chem Int Ed Engl 56:13612–13617. https://doi.org/10.1002/anie.201706522

    Article  CAS  Google Scholar 

  • Li J, He J, Huang Y (2016) Role of alginate in antibacterial finishing of textiles. Int J Biol Macromol 94:466–473

    Article  Google Scholar 

  • Li Y, Li W, Qian Z, Zhang L, Dong L, Wang L, Tang S (2017) Synthesis of N-phenylmaleimide/styrene/alpha methyl styrene/maleic anhydride tetrapolymers and its modification to ABS resin. Polym Mater Sci Eng 33:1–6. https://doi.org/10.16865/j.cnki.1000-7555.2017.06.001

  • Liu X, Xu Y (2014) Preparation process and antimicrobial properties of cross-linking chitosan onto periodate-oxidized bamboo pulp fabric. Fibers Polym 15:1887–1894

    Article  CAS  Google Scholar 

  • Navik R, Thirugnanasampanthan L, Venkatesan H, Kamruzzaman M, Shafiq F, Cai Y (2017) Synthesis and application of magnesium peroxide on cotton fabric for antibacterial properties. Cellulose 24:3573–3587. https://doi.org/10.1007/s10570-017-1356-0

    Article  CAS  Google Scholar 

  • Orhan M, Kut D, Gunesoglu C (2009) Improving the antibacterial activity of cotton fabrics finished with triclosan by the use of 1,2,3,4-butanetetracarboxylic acid and citric acid. J Appl Polym Sci 111:1344–1352. https://doi.org/10.1002/app.2508

    Article  CAS  Google Scholar 

  • Pounder RJ, Stanford MJ, Brooks P, Richards SP, Dove AP (2008) Metal free thiol-maleimide ‘Click’ reaction as a mild functionalisation strategy for degradable polymers. Chem Commun (Camb). https://doi.org/10.1039/b809167f

    Google Scholar 

  • Ravi S, Krishnamurthy VR, Caves JM, Haller CA, Chaikof EL (2012) Maleimide-thiol coupling of a bioactive peptide to an elastin-like protein polymer. Acta Biomater 8:627–635. https://doi.org/10.1016/j.actbio.2011.10.027

    Article  CAS  Google Scholar 

  • Ravindra S, Murali Mohan Y, Narayana Reddy N, Mohana Raju K (2010) Fabrication of antibacterial cotton fibres loaded with silver nanoparticles via “Green Approach”. Colloids Surf A 367:31–40. https://doi.org/10.1016/j.colsurfa.2010.06.013

    Article  CAS  Google Scholar 

  • Salewska N, Boros-Majewska J, Lacka I, Chylinska K, Sabisz M, Milewski S, Milewska MJ (2012) Chemical reactivity and antimicrobial activity of N-substituted maleimides. J Enzyme Inhib Med Chem 27:117–124. https://doi.org/10.3109/14756366.2011.580455

    Article  CAS  Google Scholar 

  • Sanchez A, Pedroso E, Grandas A (2013) Oligonucleotide cyclization: the thiol-maleimide reaction revisited. Chem Commun (Camb) 49:309–311. https://doi.org/10.1039/c2cc35357a

    Article  CAS  Google Scholar 

  • Singh D, Chauhan NPS, Mozafari M, Hiran BL (2016) High-temperature resistive free radically synthesized chloro-substituted phenyl maleimide antimicrobial polymers. J Macromol Sci Part D—Rev Polym Process 55:1916–1939

    CAS  Google Scholar 

  • Sun D, Wang W, Yu D (2016) Preparation of fluorine-free water repellent finishing via thiol-ene click reaction on cotton fabrics. Mater Lett 185:514–518

    Article  CAS  Google Scholar 

  • Travi M, Cremonesi L, Primignani P, Di BS, Testa R, Schilirò G, Ferrari M (2013) Antibacterial characteristics of electroless plating Ni–P–TiO2 coatings. Appl Surf Sci 274:101–104

    Article  Google Scholar 

  • Wang Y, Wang W, Liu B, Yu D (2017) Preparation of durable antibacterial and electrically conductive polyacrylonitrile fibers by copper sulfide coating. J Appl Polym Sci 134:45496. https://doi.org/10.1002/app.45496

  • Xi W, Scott TF, Kloxin CJ, Bowman CN (2014) Click Chemistry: click Chemistry in Materials Science. Adv Funct Mater 24:2566. https://doi.org/10.1002/adfm.201470113

    Article  Google Scholar 

  • Xu S et al (2016) Preparation and controlled coating of hydroxyl-modified silver nanoparticles on silk fibers through intermolecular interaction-induced self-assembly. Mater Des 95:107–118

    Article  CAS  Google Scholar 

  • Xu L, Wang W, Yu D (2017a) Durable flame retardant finishing of cotton fabrics with halogen-free organophosphonate by UV photoinitiated thiol-ene click chemistry. Carbohydr Polym 172:275–283

    Article  CAS  Google Scholar 

  • Xu L, Wang W, Yu D (2017b) Preparation of a reactive flame retardant and its finishing on cotton fabrics based on click chemistry. RSC Adv 7:2044–2050

    Article  CAS  Google Scholar 

  • Yu D, Xu L, Hu Y, Li Y, Wang W (2017) Durable antibacterial finishing of cotton fabric based on thiol–epoxy click chemistry. RSC Adv 7:18838–18843. https://doi.org/10.1039/c6ra28803k

    Article  CAS  Google Scholar 

  • Yue X, Lin H, Yan T, Zhang D, Lin H, Chen Y (2014) Synthesis of silver nanoparticles with sericin and functional finishing to cotton fabrics. Fibers Polym 15:716–722

    Article  CAS  Google Scholar 

  • Zhang F, Wu X, Chen Y, Lin H (2009) Application of silver nanoparticles to cotton fabric as an antibacterial textile finish. Fibers Polym 10:496–501. https://doi.org/10.1007/s12221-009-0496-8

    Article  CAS  Google Scholar 

  • Zhao C, Dong J, Li S, Fan Z (2012) Synthesis and characterization of heat-resistant N-phenylmaleimide-styrene-maleic anhydride copolymers and application in acrylonitrile–butadiene–styrene resin. J Appl Polym Sci 126:169–178

    Article  CAS  Google Scholar 

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Acknowledgments

The research was supported by the Fundamental Research Funds for the Central Universities (No. 16D110518) and National Natural Science Foundation of China (No. 51403032).

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Authors and Affiliations

  1. State Key Lab for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Road, Songjiang District, Shanghai, 201620, People’s Republic of China

    Zhonglin Fei, Wei Wang & Dan Yu

  2. State Key Lab for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People’s Republic of China

    Zhonglin Fei, Baojiang Liu, Meifang Zhu, Wei Wang & Dan Yu

  3. Saintyear Holding Group Co., Ltd, Hangzhou, People’s Republic of China

    Dan Yu

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  1. Zhonglin Fei
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  2. Baojiang Liu
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  3. Meifang Zhu
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  4. Wei Wang
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  5. Dan Yu
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Correspondence to Dan Yu.

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Fei, Z., Liu, B., Zhu, M. et al. Antibacterial finishing of cotton fabrics based on thiol-maleimide click chemistry. Cellulose 25, 3179–3188 (2018). https://doi.org/10.1007/s10570-018-1771-x

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