Non-Leaching, Rapid Bactericidal and Biocompatible Polyester Fabrics Finished with Benzophenone Terminated N-halamine

Abstract

Pathogenic bacteria can proliferate rapidly on porous fabrics to form bacterial plaques/biofilms, resulting in potential sources of cross-transmissions of diseases and increasing cross-infection in public environments. Many works on antibacterial modification of cotton fabrics have been reported, while very few works were reported to endow poly(ethylene terephthalate) (PET) fabrics with non-leaching antibacterial function without compromising their innate physicochemical properties though PET is the most widely used fabric. Therefore, it is urgent to impart the PET fabrics with non-leaching antibacterial activity. Herein, a novel N-halamine compound, 1-chloro-3-benzophenone-5,5-dimethylhydantoin (Cl-BPDMH), was developed to be covalently bonded onto PET fabrics, rendering non-leaching antibacterial activity while negligible cytotoxicity based on contact-killing principle. Bacterial was easily adhered to Cl-BPDMH finished PET fabrics, and then it was inactivated quickly within 10 s. Furthermore, the breaking strength, breaking elongation, tearing strength, water vapor permeability, air permeability and whiteness of Cl-BPDMH finished PET fabrics were improved obviously compared to raw PET fabrics. Hence, this work developed a facile approach to fabricate multifunctional synthetic textiles to render outstanding and rapid bactericidal activity without compromising their physicochemical properties and biocompatibility.

Keywords

Poly(ethylene terephthalate) / Fabric / Bactericidal / N-halamine / Photochemical reaction

References

[1] WangML, ZhangMJ, PangLJ, YangCG, ZhangYM, HuJT, WuGZ. Fabrication of highly durable polysiloxane-zinc oxide (ZnO) coated polyethylene terephthalate (PET) fabric with improved ultraviolet resistance, hydrophobicity, and thermal resistance. J Colloid Interf Sci, 2019, 537: 91.

[2] ChenSG, ZhangSB, GalluzziM, LiF, ZhangXC, YangXH, LiuXY, CaiXH, ZhuXL, DuB, LiJN, HuangP. Insight into multifunctional polyester fabrics finished by one-step eco-friendly strategy. Chem Eng J, 2019, 358: 634.

[3] BrownED, WrightGD. Antibacterial drug discovery in the resistance era. Nature, 2016, 529: 336.

[4] LiN, PranantyoD, KangET, WrightDS, LuoHK. In situ self-assembled polyoxotitanate cages on flexible cellulosic substrates: multifunctional coating for hydrophobic, antibacterial, and uv-blocking applications. Adv Funct Mater, 2018, 28: 1800345.

[5] XiaGX, WuYM, BiYF, ChenK, ZhangWW, LiuSQ, ZhangWJ, LiuRH. Antimicrobial properties and application of polysaccharides and their derivatives. Chinese J Polym Sci, 2021, 39: 133.

[6] ZhouM, QianY, XieJ, ZhangW, JiangW, XiaoX, ChenS, DaiC, CongZ, JiZ, ShaoN, LiuL, WuY, LiuR. Poly(2-Oxazoline)-based functional peptide mimics: eradicating MRSA infections and persisters while alleviating antimicrobial resistance. Angew Chem Int Ed, 2020, 59: 6412.

[7] SreejaS, MuraleedharanCV, VarmaPRH, SailajaGS. Surface-transformed osteoinductive polyethylene terephthalate scaffold as a dual system for bone tissue regeneration with localized antibiotic delivery. Mater Sci Eng C, 2020, 109: 16.

[8] WuM, MaB, PanT, ChenS, SunJ. Silver-nanoparticle-colored cotton fabrics with tunable colors and durable antibacterial and self-healing superhydrophobic properties. Adv Funct Mater, 2016, 26: 569.

[9] LiuQX, HuangJ, ZhangJM, HongY, WanYB, WangQ, GongML, WuZG, GuoCF. Thermal, waterproof, breathable, and antibacterial cloth with a nanoporous structure. ACS Appl Mater Interfaces, 2018, 10: 2026.

[10] YunG, PanS, WangTY, GuoJ, RichardsonJJ, CarusoF. Synthesis of metal nanoparticles in metal-phenolic networks: Catalytic and antimicrobial applications of coated textiles. Adv Healthcare Mater, 2018, 7: 1700934.

[11] AmaniA, MontazerM, MahmoudiradM. Low starch/corn silk/ZnO as environmentally friendly nanocomposites assembling on PET fabrics. Int J Biol Macromol, 2021, 170: 780.

[12] Zhang T, Yu H, Li J, Song H, Wang S, Zhang Z, Chen S Green light–triggered antimicrobial cotton fabric for wastewater disinfection, Mater Today Phys, 2020;15:100254.

[13] GaoD, LiY, LyuB, LyuL, ChenS, MaJ. Construction of durable antibacterial and anti-mildew cotton fabric based on P(DMDAAC-AGE)/Ag/ZnO composites. Carbohyd Polym, 2019, 204: 161.

[14] RehanM, El-NaggarME, MashalyHM, WilkenR. Nanocomposites based on chitosan/silver/clay for durable multi-functional properties of cotton fabrics. Carbohyd Polym, 2018, 182: 29.

[15] Ding S, Wang Y, Li J, Chen S.Progress and prospects in chitosan derivatives: Modification strategies and medical applications, J Mater Sci Technol2021; in press https://doi.org/10.1016/j.jmst.2020.12.008.

[16] ChenSG, YuanLJ, LiQQ, LiJN, ZhuXL, JiangYG, ShaO, YangXH, XinJH, WangJX, StadlerFJ, HuangP. Durable antibacterial and nonfouling cotton textiles with enhanced comfort via zwitterionic sulfopropylbetaine coating. Small, 2016, 12: 3516.

[17] ChenSG, ChenSJ, JiangS, XiongML, LuoJX, TangJN, GeZC. Environmentally friendly antibacterial cotton textiles finished with siloxane sulfopropylbetaine. ACS Appl Mater Interfaces, 2011, 3: 1154.

[18] XuJ, ZhaoH, XieZ, RuppelS, ZhouX, ChenS, LiangJF, WangX. Stereochemical strategy advances microbially antiadhesive cotton textile in safeguarding skin flora. Adv Healthcare Mater, 2019, 8: 1900232.

[19] LiX, BaiH, YangY, YoonJ, WangS, ZhangX. Supramolecular antibacterial materials for combatting antibiotic resistance. Adv Mater, 2019, 31: 1805092

[20] ZhangSB, YangXH, TangB, YuanLJ, WangK, LiuXY, ZhuXL, LiJN, GeZC, ChenSG. New insights into synergistic antimicrobial and antifouling cotton fabrics via dually finished with quaternary ammonium salt and zwitterionic sulfobetaine. Chem Eng J, 2018, 336: 123.

[21] ZhangSM, LiR, HuangD, RenXH, HuangTS. Antibacterial modification of PET with quaternary ammonium salt and silver particles via electron-beam irradiation. Mater Sci Eng C, 2018, 85: 123.

[22] XuJ, XieZ, DuF, WangX. One-step anti-superbug finishing of cotton textiles with dopamine-menthol. J Mater Sci Technol, 2021, 69: 79.

[23] HanH, ZhuJ, WuDQ, LiFX, WangXL, YuJY, QinXH. Inherent guanidine nanogels with durable antibacterial and bacterially antiadhesive properties. Adv Funct Mater, 2019, 29: 1806594.

[24] CaoYH, GuJW, WangS, ZhangZC, YuHL, LiJN, ChenSG. Guanidine-functionalized cotton fabrics for achieving permanent antibacterial activity without compromising their physicochemical properties and cytocompatibility. Cellulose, 2020, 27: 6027.

[25] ChenW, ZhuY, ZhangZ, GaoY, LiuW, BorjihanQ, QuH, ZhangY, ZhangY, WangY, ZhangL, DongA. Engineering a multifunctional N-halamine-based antibacterial hydrogel using a super-convenient strategy for infected skin defect therapy. Chem Eng J, 2020, 379: 122238.

[26] TangX, XuH, ShiY, WuM, TianH, LiangJ. Porous antimicrobial starch particles containing N-halamine functional groups. Carbohyd Polym, 2020, 229: 115546.

[27] BaiR, KangJ, SimalouO, LiuWX, RenH, GaoTY, GaoYY, ChenWJ, DongA, JiaR. Novel N-Br bond-containing N-halamine nanofibers with antibacterial activities. ACS Biomater Sci Eng, 2018, 4: 2193.

[28] DongA, WangY, GaoY, GaoT, GaoG. Chemical insights into antibacterial N-halamines. Chem Rev, 2017, 117: 4806.

[29] Liang M, Wang F, Liu M, Yu J, Si Y, Ding B N-halamine functionalized electrospun poly(vinyl alcohol-co-ethylene) nanofibrous membranes with rechargeable antibacterial activity for bioprotective applications, Adv Fiber Mater2019; 1:126.

[30] ChenYJ, WorleySD, KimJ, WeiCI, ChenTY, SantiagoJI, WilliamsJF, SunG. Biocidal poly(styrenehydantoin) beads for disinfection of water. Ind Eng Chem Res, 2003, 42: 280.

[31] ChenY, WangYY, FengCY, HeQK, ChenQ, WangZD, HanQX. Novel quat/di-N-halamines silane unit with enhanced synergism polymerized on cellulose for development of superior biocidability. Int J Biol Macromol, 2020, 154: 173.

[32] TsaoTC, WilliamsDE, WorleyCG, WorleySD. Novel N-halamine disinfectant compounds. Biotech Prog, 1991, 7: 60.

[33] KovacicP, LoweryMK, FieldKW. Chemistry of N-bromamines and N-chloramines. Chem Rev, 1970, 70: 639.

[34] RenT, HaydenM, QuoM, HuangTS, RenX, WeeselJ. Absorbent pads containing N-halamine compound for potential antimicrobial use for chicken breast and ground chicken. J Agric Food Chem, 2018, 66: 1941.

[35] MaY, LiJ, SiY, HuangK, NitinN, SunG. Rechargeable antibacterial N-halamine films with antifouling function for food packaging applications. ACS Appl Mater Interfaces, 2019, 11: 17814.

[36] Wang YF, Yin ML, Ma W, Li ZG, Xu ZZ, Ren XH N-halamine modified mesoporous silica coated cotton as multipurpose protective fibrous materials, Cellulose, 2020; 27: 10461.

[37] SunX, ZhangL, CaoZ, DengY, LiuL, FongH, SunY. Electrospun composite nanofiber fabrics containing uniformly dispersed antimicrobial agents as an innovative type of polymeric materials with superior antimicrobial efficacy. ACS Appl Mater Interfaces, 2010, 2: 952.

[38] Liang J, Chen Y, Barnes K, Wu R, Worley SD, Huang TS N-halamine/quat siloxane copolymers for use in biocidal coatings, Biomaterials, 2006; 27:2495.

[39] LiuY, LiJ, LiL, McFarlandS, RenX, AcevedoO, HuangTS. Characterization and mechanism for the protection of photolytic decomposition of N-halamine siloxane coatings by titanium dioxide. ACS Appl Mater Interfaces, 2016, 8: 3516.

[40] LiuC, ShanH, ChenX, SiY, YinX, YuJ, DingB. Novel inorganic-based N-halamine nanofibrous membranes as highly effective antibacterial agent for water disinfection. ACS Appl Mater Interfaces, 2018, 10: 44209.

[41] KocerHB, CerkezI, WorleySD, BroughtonRM, HuangTS. Polymeric antimicrobial N-halamine epoxides. ACS Appl Mater Interfaces, 2011, 3: 2845.

[42] LvJ, ZhouQ, ZhiT, GaoD, WangC. Environmentally friendly surface modification of polyethylene terephthalate (PET) fabric by low-temperature oxygen plasma and carboxymethyl chitosan. J Clean Prod, 2016, 118: 187.

[43] Del HoyoGS, Pérez ÁlvarezL, Gómez GalvánF, LizundiaE, KuritkaI, SedlarikV, LazaJM, Vila VilelaJL. Construction of antibacterial poly(ethylene terephthalate) films via layer by layer assembly of chitosan and hyaluronic acid. Carbohyd Polym, 2016, 143: 35.

[44] ZhangS, KaiC, LiuB, ZhangS, WeiW, XuX, ZhouZ. Preparation, characterization and antibacterial properties of cellulose membrane containing N-halamine. Cellulose, 2019, 26: 5621.

[45] MaW, LiL, XiaoX, DuH, RenX, ZhangX, HuangT. Construction of chlorine labeled ZnO–chitosan loaded cellulose nanofibrils film with quick antibacterial performance and prominent UV stability. Macromol Mater Eng, 2020, 305: 2000228.

[46] GuJW, YuanLJ, ZhangZ, YangXH, LuoJX, GuiZF, ChenSG. Non-leaching bactericidal cotton fabrics with well-preserved physical properties, no skin irritation and no toxicity. Cellulose, 2018, 25: 5415.

[47] ZhangT, GuJW, LiuXY, WeiD, ZhouHL, XiaoHH, ZhangZC, YuHL, ChenSG. Bactericidal and antifouling electrospun PVA nanofibers modified with a quaternary ammonium salt and zwitterionic sulfopropylbetaine. Mater Sci Eng C, 2020, 111: 110855.

[48] ChenYX, LiJN, LiQQ, ShenYY, GeZC, ZhangWW, ChenSG. Enhanced water-solubility, antibacterial activity and biocompatibility upon introducing sulfobetaine and quaternary ammonium to chitosan. Carbohyd Polym, 2016, 143: 246.

[49] DongA, LanS, HuangJ, WangT, ZhaoT, WangW, XiaoL, ZhengX, LiuF, GaoG, ChenY. Preparation of magnetically separable N-halamine nanocomposites for the improved antibacterial application. J Colloid Interf Sci, 2011, 364: 333.

[50] ZhengY, PanN, LiuY, RenX. Novel porous chitosan/N-halamine structure with efficient antibacterial and hemostatic properties. Carbohyd Polym, 2021, 253: 117205.

[51] KellAJ, StewartG, RyanS, PeytaviR, BoissinotM, HuletskyA, BergeronMG, SimardB. Vancomycin-modified nanoparticles for efficient targeting and preconcentration of Gram-positive and Gram-negative bacteria. ACS Nano, 2008, 2: 1777.

[52] ZhouJ, HuZ, ZabihiF, ChenZ, ZhuM. Progress and perspective of antiviral protective material. Adv Fiber Mater, 2020, 2: 123.

[53] ChenX, WangY, DaiGL, PengJ, LiJQ, ShiMW, ZhaiML. Radiation grafting of glycidyl methacrylate and divinylbenzene onto polyethylene terephthalate fabrics for improving anti-dripping performance. Radiat Phys Chem, 2016, 127: 256.

[54] ChaoP, ChenH, ZhuY, ZhengN, MengH, HeF. Chlorination of conjugated side chains to enhance intermolecular interactions for elevated solar conversion. Macromolecules, 2020, 53: 165.

Funding

the National Natural Science Foundation of China(51773117)

Science and Technology Planning Project of Shenzhen Municipality(JSGG20201102154400001)

the Collaborative Innovation and Nanshan District Key lab for Biopolymers and Safety Evaluation(KC2014ZDZJ0001A)

RIGHTS & PERMISSIONS

Donghua University, Shanghai, China