Synthesis of Novel <i>N</i>-Halamine Epoxide Based on Cyanuric Acid and Its Application for Antimicrobial Finishing

Ma, Kaikai; Liu, Ying; Xie, Zhiwei; Li, Rong; Jiang, Zhiming; Ren, Xiaofeng; Huang, Tung‐Shi

doi:10.1021/ie400122h

Cited by 49 publications

(51 citation statements)

References 31 publications

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“…The shifts to higher wavenumber of the hydantoin carbonyl bands upon chlorination have been also reported for other Nhalamines. 40,41 The band at 1698 cm −1 is observed in cotton coated with PSPH/TiO 2 (as shown in Figure 4D), correspond- Figure 5 shows the XRD patterns of rutile titanium dioxide, cotton coated with PSPH/TiO 2 , and chlorinated cotton coated with PSPH/TiO 2 . The peaks at 27.56°, 36.18°, 41.36°, and 54.42°for rutile titanium dioxide are observed as shown in Figure 5(A) and attributed to the (110), (101), (111), and (211) lattice planes of the rutile phase which is consistent with rutile TiO 2 reported by others.…”

Section: ■ Results and Discussionmentioning

confidence: 79%

Antimicrobial Cellulose Modified with Nanotitania and Cyclic N-Halamine

Liu

Jiang

et al. 2014

Ind. Eng. Chem. Res.

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Organic−inorganic composites have the drawn attention of researchers due to their combined properties. In this work, poly [5,5-dimethyl-3-(3′-triethoxysilylpropyl)hydantoin] (PSPH) was synthesized and coated onto cotton fibers together with titania nanoparticles (TiO 2 ) by chemical binding in a one-bath process. The treated cotton with improved UV stability can produce biocidal properties against S. aureus (ATCC 6538) and E. coli O157:H7 (ATCC 43895) upon chlorination with diluted sodium hypochlorite solutions. The characteristics of the coated cotton were determined by SEM, FTIR, XRD, and XPS, and the washing stability and antibacterial efficacies were tested. Moreover, the N−Cl bond and compound stability under UV irradiation were measured. It was found that the treated cotton showed excellent antimicrobial properties within a brief contact time and great washing stability. The N−Cl bond and compound itself showed excellent stability under UV light irradiation. ■ INTRODUCTIONAs surface antibacterial agents, phosphonium salts, 1−3 quaternary ammonium salts, 4−6 chitosan, 7−9 and N-halamine compounds 10−17 are currently studied and applied in infection control. Among these materials, N-halamine compounds show superior antibacterial properties against a broad spectrum of bacteria within brief contact times with advantages of being environmentally friendly and exhibiting regeneration upon exposure to household bleach solution. The oxidative halogen of N-halamine compounds can be directly transferred to the microbial cell membrane and then inactivate the microorganisms. The poor UV stabilities of some of the N-halamine compounds might limit their practical application. For example, N−Cl bonds of N-halamine siloxanes and covalent bonds between hydantoin siloxanes and cellulose are easily broken under UV light irradiation. 18−20 In our previous work, 21 we have reported that nanotitania was incorporated into the coating of N-halamine diols onto cotton via 1,2,3,4-butanetetracarboxylic acid (BTCA), and the addition of nanotitania in the coatings could dramatically improve the UV stabilities of the N-halamine diols. Therefore, it may be advantageous to bind nanotitania to N-halamine siloxanes and coat onto the fiber surface by covalent bonds to produce antibacterial cotton with improved UV stability and excellent washing stability.Organic−inorganic hybrid materials have received significant interest for a wide range of electronic, 22 magnetic, 23 and optical performances 24−26 because of their better performance properties over the corresponding pure organic or inorganic materials. The usual methods to synthesize the organic−inorganic hybrid compounds are sol−gel, 27−29 in-suit polymerization, 30 and other methods. 31,32 Organosilanes containing one or more alkoxy groups, such as ethyoxy and methoxy groups (−OC 2 H 5 and −OCH 3 ), are widely used as surface modification agents for materials. 33−35 Upon application, alkoxy groups of organosilanes are hydrolyzed to form silanol which can react with OH groups of the subst...

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Section: ■ Results and Discussionmentioning

confidence: 79%

Antimicrobial Cellulose Modified with Nanotitania and Cyclic N-Halamine

Liu

Jiang

et al. 2014

Ind. Eng. Chem. Res.

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“…1A and B), a new wide vibrational band appeared at 1555-1510 cm À1 for the CA-MDI nanofibers, which is probably attributed to the vibrational band of -NH(II) [40] and aromatic ring [41] and the characteristic vibrational band of the cyanate ester group did not appear at 2275 cm À1 . The bond located at 1750 cm À1 was assigned to the vibrational bond of C5 5O group [42], and the intensity of this band increased compared with pure CA nanofibers due to the grafting MDI on CA molecules, as shown in Fig. 1C.…”

Section: Ft-irmentioning

confidence: 89%

Electrospun non-leaching biocombatible antimicrobial cellulose acetate nanofibrous mats

Jiang

Ren

et al. 2015

Journal of Industrial and Engineering Chemistry

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“…Ma et al [40] reports the synthesis of N-halamine epoxide and grafting with cotton fabrics to apply for antimicrobial dressings. N-halamines-based antimicrobial activities depend on the stabilities of the halamine bond and structure (descending order imide > amide > amine).…”

Section: Drug Moleculesmentioning

confidence: 99%

Eco-Friendly Cellulose–Polymer Nanocomposites: Synthesis, Properties and Applications

Karuppusamy

Panneerselvam

Kulandainathan

2015

Advanced Structured Materials

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Grafting or deposition is a powerful tool to modify the cellulose/textile surfaces permanently with precisely controlled structure in nanometer to micrometre scale, which leads to multifunctional applications. The properties that can be imparted through functionalization include superhydrophobicity, superoleopholicity, shape memory effect, high conductivity, drug storage/delivery, flame retardant, heat storage/release, and UV protection. Through this functionalization new applications for textile can be achieved such as waterproof textiles, textile actuators, fire resistive textiles, UV-protective materials, Band-Aids, transdermal batches, medical textiles, supercapacitor electrodes, separator of oil-water mixture, wearable textile electronics, conductive textiles, self-protection cloths. This chapter summarises recent publications about modifying the cellulose surfaces with biopolymers along with nanoparticles and their composites used for superhydrophobicity, oil-water separation, conducting fabrics and drug delivery devices leading to smart bandages. The main objective is to clarify the true significance of functionalization for each application. Thus, another important purpose of this chapter is to establish general guidelines for functionalization and propose future direction for cheaper devices that can elevate the textile industries.

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Synthesis of Novel N-Halamine Epoxide Based on Cyanuric Acid and Its Application for Antimicrobial Finishing

Cited by 49 publications

References 31 publications

Antimicrobial Cellulose Modified with Nanotitania and Cyclic N-Halamine

Antimicrobial Cellulose Modified with Nanotitania and Cyclic N-Halamine

Electrospun non-leaching biocombatible antimicrobial cellulose acetate nanofibrous mats

Eco-Friendly Cellulose–Polymer Nanocomposites: Synthesis, Properties and Applications

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