US20160076194A1 - The preparation of N-halamine antibacterial materials based on cyanuric chloride - Google Patents

The preparation of N-halamine antibacterial materials based on cyanuric chloride Download PDF

Info

Publication number
US20160076194A1
US20160076194A1 US14/768,450 US201414768450A US2016076194A1 US 20160076194 A1 US20160076194 A1 US 20160076194A1 US 201414768450 A US201414768450 A US 201414768450A US 2016076194 A1 US2016076194 A1 US 2016076194A1
Authority
US
United States
Prior art keywords
solution
cyanuric chloride
materials
mass percent
sodium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US14/768,450
Inventor
Xuehong Ren
Kaikai MA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangnan University
Original Assignee
Jiangnan University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangnan University filed Critical Jiangnan University
Assigned to JIANGNAN UNIVERSITY reassignment JIANGNAN UNIVERSITY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MA, Kaikai, REN, XUEHONG
Publication of US20160076194A1 publication Critical patent/US20160076194A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35Heterocyclic compounds
    • D06M13/355Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358Triazines
    • D06M13/364Cyanuric acid; Isocyanuric acid; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/661,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2400/00Specific information on the treatment or the process itself not provided in D06M23/00-D06M23/18
    • D06M2400/01Creating covalent bondings between the treating agent and the fibre

Definitions

  • the invention belongs to the technical field of antibacterial materials. It presents a method to produce N-halamine antibacterial materials based on cyanuric chloride.
  • Infections caused by microorganisms are among the greatest threats to human being, and materials including plastics and textiles are ideal carriers and media for microorganisms.
  • Extensive researches on producing antimicrobial materials have focused on biocidal agents, such as quaternary ammonium salts, metal ions, light-activated coatings, phosphonium salts, and N-halamines.
  • N-Halamines are the most promising candidates for use in preparing antimicrobial materials because of their broad-spectrum antibacterial activity, nontoxicity, and low environmental impacts.
  • their antibacterial properties are durable and rechargeable. They have long shelf life once covalently attached to materials, and their chlorine can be regenerated simply by exposure to household bleach in the washing process.
  • the invention discloses a method to prepare N-halamine antibacterial materials based on cyanuric chloride.
  • the processing method in this invention is simple, cheap, and energy-saving. This method only caused very small loss of physical strength. The resulted materials have strong antibacterial efficacy.
  • the aim of invention can be realized by the following technical scheme. Firstly, cyanuric chloride is dissolved in alkaline solution to produce finishing solution. Then the materials are dipped in the finishing solution to absorb liquid. The wetted materials are taken out, cured under 90-120° C. for 10-40 min, chlorinated by bleach solution, washed and dried to get antibacterial materials.
  • the cyanuric chloride concentration is from 0.5-30% and optimized as 1-5%. Concentration of alkalines including NaOH, KOH, Na 2 CO 3 , K 2 CO 3 mentioned above in finishing solution ranges from 1-30% and optimized as 2-5%.
  • the bleaching solution mentioned above includes but not limited to, NaClO, NaBrO, and Ca(ClO) 2 .
  • the concentration of the active halogen is from 0.01-5% and optimized as 0.01-0.05%.
  • the pH value of the bleaching solution is from 4-12.
  • the treated materials mentioned in claim 1 include but not limited to natural fiber or synthetic fiber textiles, plastics, sponge, natural rubber, synthetic rubber, wood, paper, paint, chitosan and chitin.
  • the curing process can be chosen from baking oven, hot pressing, roller handle, and hot air treatment.
  • the treated material is textile, a traditional two-dip-two-rolling process can be used.
  • the wet pick-up is 100%.
  • this invention Compared with the preparation process of existing N-halamine antibacterial materials, this invention has the following advantages.
  • Preparation process and finished product are formaldehyde-free and non-toxic.
  • the processing method in this invention is simple, cheap, and energy-saving. This method only caused very small loss of physical strength. For example, the treated fabric loses less than 20% breaking strength. The resulted materials have strong antibacterial efficacy.
  • the treated cotton fabrics inactivated 99.999% S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) within 1 min of contact time.
  • the treated fabrics provide a total inactivation of S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) with 7-logs within the contact time of 10 and 5 min, respectively, according to AATCC 100 standard testing method.
  • FIG. 1 The schematic diagram of the antibacterial finishing method.
  • FIG. 2 The schematic diagram of antibacterial material's inactivation and bactericidal activity regeneration.
  • FIG. 3 FTIR spectra of (A) untreated cotton, (B) cotton treated with 4% triazine, and (C) cotton treated with 4% triazine after chlorination.
  • N-halamine precursors through controlled hydrolysis of cyanuric chloride, and attach them onto cellulose by covalent bonds.
  • C—Cl groups in cyanuric chloride are quite active because of triazine ring's strong electron withdrawing effect.
  • the first chlorine atom of cyanuric chloride can be replaced by a hydroxyl group in an alkali aqueous solution forming water soluble compounds in the form of sodium salts, as shown in FIG. 1 .
  • the amide and imide of triazine rings immobilized on cotton fibers were transformed to amide and imide N-halamines after bleach treatment, which have efficient and renewable antibacterial property as shown in FIG. 2 .
  • FTIR spectrum of cotton treated with triazine in FIG. 3 shows characteristic absorption bands at 1713 cm ⁇ 1 and at 1610 cm ⁇ 1 , which indicated that triazine was successfully attached to cellulose through covalent bonds because unreacted water-soluble triazine could be easily washed off from the surface of cotton fabric.
  • the chlorinated cotton samples were washed thoroughly with distilled water and dried at 45° C. for 2 h to remove all unbonded chlorine from the surface of the fabric.
  • the concentration of loaded chlorine on the samples was 0.68%, determined by the iodometric/thiosulfate titration method.
  • the chlorinated cotton samples were washed thoroughly with distilled water and dried at 45° C. for 2 h to remove all unbonded chlorine from the surface of the fabric.
  • the concentration of loaded chlorine on the samples was 0.86%, determined by the iodometric/thiosulfate titration method.
  • the chlorinated cotton samples were washed thoroughly with distilled water and dried at 45° C. for 2 h to remove all unbonded chlorine from the surface of the fabric.
  • the concentration of loaded chlorine on the samples was 0.99%, determined by the iodometric/thiosulfate titration method.
  • the chlorinated modified cotton fabrics inactivated 99.999% S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) within 1 min of contact time.
  • the chlorinated modified fabrics provide a total inactivation of S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) with 7-logs within the contact time of 10 and 5 min, respectively.
  • the biocidal efficacy is comparable to amide N-halamine modified fabrics, but better than those amine N-halamines reported previously.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

The invention discloses a method to prepare N-halamine antibacterial materials based on cyanuric chloride. Firstly, cyanuric chloride is dissolved in alkaline solution to produce finishing solution. Then the materials are dipped in the finishing solution to absorb liquid. The wetted materials are taken out, cured under 90˜120° C. for 10˜40 min, chlorinated by bleach solution, washed and dried to get antibacterial materials. The processing method in this invention is simple, cheap, and energy-saving. In addition, it only caused very small loss of physical strength. The resulted materials have strong antibacterial efficacy, are safe for application.

Description

    CROSS-REFERENCE TO RELATED APPLICATIONS
  • This application claims priority from CN Application No. 201310056994.4, filed Feb. 22, 2013 and PCT Application No. PCT/CN2014/072161, filed Feb. 17, 2014, the contents of which are incorporated herein in the entirety by reference.
  • FIELD OF THE INVENTION
  • The invention belongs to the technical field of antibacterial materials. It presents a method to produce N-halamine antibacterial materials based on cyanuric chloride.
  • BACKGROUND OF THE INVENTION
  • Infections caused by microorganisms are among the greatest threats to human being, and materials including plastics and textiles are ideal carriers and media for microorganisms. Extensive researches on producing antimicrobial materials have focused on biocidal agents, such as quaternary ammonium salts, metal ions, light-activated coatings, phosphonium salts, and N-halamines.
  • N-Halamines are the most promising candidates for use in preparing antimicrobial materials because of their broad-spectrum antibacterial activity, nontoxicity, and low environmental impacts. In addition, their antibacterial properties are durable and rechargeable. They have long shelf life once covalently attached to materials, and their chlorine can be regenerated simply by exposure to household bleach in the washing process.
  • However, there are inherent disadvantages in coating these compounds onto fabrics. Because of their poor solubility in water, or organic solvents are needed during the preparation of coating solutions used for some of N-halamine precursors.
  • In this patent, a novel method is used to form N-halamine precursors through controlled hydrolysis of cyanuric chloride, and attach them onto cellulose by covalent bonds. The reactions progressed under a facile condition and employed water as a solvent. They are easy to scale-up in practical applications.
  • SUMMARY OF THE INVENTION
  • The invention discloses a method to prepare N-halamine antibacterial materials based on cyanuric chloride. The processing method in this invention is simple, cheap, and energy-saving. This method only caused very small loss of physical strength. The resulted materials have strong antibacterial efficacy.
  • The aim of invention can be realized by the following technical scheme. Firstly, cyanuric chloride is dissolved in alkaline solution to produce finishing solution. Then the materials are dipped in the finishing solution to absorb liquid. The wetted materials are taken out, cured under 90-120° C. for 10-40 min, chlorinated by bleach solution, washed and dried to get antibacterial materials.
  • More detailed technical scheme is present as follow.
  • The cyanuric chloride concentration is from 0.5-30% and optimized as 1-5%. Concentration of alkalines including NaOH, KOH, Na2CO3, K2CO3 mentioned above in finishing solution ranges from 1-30% and optimized as 2-5%.
  • The bleaching solution mentioned above includes but not limited to, NaClO, NaBrO, and Ca(ClO)2. The concentration of the active halogen is from 0.01-5% and optimized as 0.01-0.05%. The pH value of the bleaching solution is from 4-12.
  • The treated materials mentioned in claim 1 include but not limited to natural fiber or synthetic fiber textiles, plastics, sponge, natural rubber, synthetic rubber, wood, paper, paint, chitosan and chitin.
  • The curing process can be chosen from baking oven, hot pressing, roller handle, and hot air treatment. When the treated material is textile, a traditional two-dip-two-rolling process can be used. The wet pick-up is 100%.
  • Compared with the preparation process of existing N-halamine antibacterial materials, this invention has the following advantages.
  • Preparation process and finished product are formaldehyde-free and non-toxic.
  • The processing method in this invention is simple, cheap, and energy-saving. This method only caused very small loss of physical strength. For example, the treated fabric loses less than 20% breaking strength. The resulted materials have strong antibacterial efficacy. For example, the treated cotton fabrics inactivated 99.999% S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) within 1 min of contact time. The treated fabrics provide a total inactivation of S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) with 7-logs within the contact time of 10 and 5 min, respectively, according to AATCC 100 standard testing method.
  • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1. The schematic diagram of the antibacterial finishing method.
  • FIG. 2. The schematic diagram of antibacterial material's inactivation and bactericidal activity regeneration.
  • FIG. 3. FTIR spectra of (A) untreated cotton, (B) cotton treated with 4% triazine, and (C) cotton treated with 4% triazine after chlorination.
  • DETAILED DESCRIPTION OF PARTICULAR EMBODIMENTS OF THE INVENTION
  • In this patent, a novel method was used to form N-halamine precursors through controlled hydrolysis of cyanuric chloride, and attach them onto cellulose by covalent bonds. When compared to ordinary alkyl halides, the C—Cl groups in cyanuric chloride are quite active because of triazine ring's strong electron withdrawing effect. The first chlorine atom of cyanuric chloride can be replaced by a hydroxyl group in an alkali aqueous solution forming water soluble compounds in the form of sodium salts, as shown in FIG. 1. The amide and imide of triazine rings immobilized on cotton fibers were transformed to amide and imide N-halamines after bleach treatment, which have efficient and renewable antibacterial property as shown in FIG. 2.
  • FTIR spectrum of cotton treated with triazine in FIG. 3 shows characteristic absorption bands at 1713 cm−1 and at 1610 cm−1, which indicated that triazine was successfully attached to cellulose through covalent bonds because unreacted water-soluble triazine could be easily washed off from the surface of cotton fabric.
  • Example 1
  • 1 g cyanuric chloride and 2 g sodium hydroxide were added to 97 g distilled water and stirred for 10 min to obtain a clear solution. Then, cotton swatches were soaked in baths for 15 min and padded with a wet pick-up of 100%. The fabrics were dipped and padded twice, then dried at 80° C. for 5 min, followed by curing at 120° C. for 10 min. The treated cotton swatches were soaked in 0.5% detergent solution for 15 min, washed with distilled water, and dried in air. The treated cotton fabric swatches were soaked in a 0.01% commercial aqueous Ca(ClO)2 solution at pH 7 at room temperature for 1 h to produce biocidal materials. The chlorinated cotton samples were washed thoroughly with distilled water and dried at 45° C. for 2 h to remove all unbonded chlorine from the surface of the fabric. The concentration of loaded chlorine on the samples was 0.68%, determined by the iodometric/thiosulfate titration method.
  • Example 2
  • 8 g cyanuric chloride and 7 g potassium hydroxide were added to 87 g distilled water and stirred for 10 min to obtain a clear solution. Then, cotton swatches were soaked in baths for 15 min and padded with a wet pick-up of 100%. The fabrics were dipped and padded twice, then dried at 80° C. for 5 min, followed by curing at 90° C. for 40 min. The treated cotton swatches were soaked in 0.5% detergent solution for 15 min, washed with distilled water, and dried in air. The treated cotton fabric swatches were soaked in a 0.5% commercial aqueous sodium hypochlorite solution at pH 12 at room temperature for 1 h to produce biocidal materials. The chlorinated cotton samples were washed thoroughly with distilled water and dried at 45° C. for 2 h to remove all unbonded chlorine from the surface of the fabric. The concentration of loaded chlorine on the samples was 0.86%, determined by the iodometric/thiosulfate titration method.
  • Example 3
  • 5 g cyanuric chloride and 11 g sodium hydroxide were added to 84 g distilled water and stirred for 10 min to obtain a clear solution. Then, cotton swatches were soaked in baths for 15 min and padded with a wet pick-up of 100%. The fabrics were dipped and padded twice, then dried at then dried at 80° C. for 5 min, followed by curing at 100° C. for 20 min. The treated cotton swatches were soaked in 0.1% detergent solution for 15 min, washed with distilled water, and dried in air. The treated cotton fabric swatches were soaked in a 0.1% commercial aqueous sodium hypochlorite solution at pH 7 at room temperature for 1 h to produce biocidal materials. The chlorinated cotton samples were washed thoroughly with distilled water and dried at 45° C. for 2 h to remove all unbonded chlorine from the surface of the fabric. The concentration of loaded chlorine on the samples was 0.99%, determined by the iodometric/thiosulfate titration method.
  • When compared to the control samples, all of the treated cotton fabrics with triazine showed a small degree of tensile strength loss, and over 84% of the original breaking strength could be maintained after chlorination both in warp and weft directions. This result means this method has a very small effect on physical properties.
  • Antimicrobial Testing
  • Both unchlorinated and chlorinated cotton treated with triazine from the example 2 were challenged with S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) at concentrations of about 107 CFUs (colony-forming units). The antimicrobial test results of the triazine treated cotton samples before and after chlorination are shown in Table III. The unchlorinated cotton samples treated with triazine was used as a control, and showed only 0.98 and 0.12 log reductions of S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) within 10 min of contact time, respectively, mainly due to adhesion of bacteria to the samples. The chlorinated modified cotton fabrics inactivated 99.999% S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) within 1 min of contact time. The chlorinated modified fabrics provide a total inactivation of S. aureus (ATCC 6538) and E. coli 0157:H7 (ATCC43895) with 7-logs within the contact time of 10 and 5 min, respectively. The biocidal efficacy is comparable to amide N-halamine modified fabrics, but better than those amine N-halamines reported previously.
  • TABLE 1
    Biocidal efcacy testing.
    S. aureus b E. coli 0.157:H7c
    Contact Bacterial reduction Bacterial reduction
    Sample Time % Log % Log
    Unchlorinated 10 min 89.58 0.98 27.23 0.14
    Chlorinateda  1 min 99.999 4.82 99.999 5.00
     5 min 99.999 5.13 100 7.43
    10 min 100 7.26 100 7.43
    a0.23% oxidative chlorine content
    bTotal bacteria: 1.80 × 107 (cfu/sample)
    cTotal bacteria: 2.67 × 107 (cfu/sample)
  • The present invention may be embodied in other specific forms without departing from the essential attributes thereof, and it is therefore desired that the present embodiments and examples be considered in all respects as illustrative and not restrictive, reference being made to the appended claims, rather than to the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.

Claims (9)

What is claimed is:
1. A method for preparing N-halamine antibacterial materials based on cyanuric chloride, characterized in that: cyanuric chloride is completely dissolved alkaline solution, and the material was immersed in the prepared solution until thoroughly wetted. The wet material was dried and cured for 10˜40 min at 90˜120° C. The antimicrobial material was obtained after halogenation, washing, and drying.
2. The method according to claim 1, wherein the alkalis are sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate solution, with mass percent of 1˜30%.
3. The method according to claim 1, wherein the mass percent of cyanuric chloride in the solution is 0.5˜30%.
4. The method according to claim 1, wherein the halogenation process means the activation of material through soaking the mentioned material in a solution containing the active halogens.
5. The method according to claim 1, wherein the treated materials include natural fiber or synthetic fiber textiles, plastics, sponge, natural rubber, synthetic rubber, wood, paper, paint, chitosan and chitin.
6. The method according to claim 1, wherein the treatment method includes two dipping-padding processes for the treatment of natural fiber or synthetic fiber textiles.
7. The method according to claim 2, wherein the alkaline concentration in solution is 2˜5%.
8. The method according to claim 3, wherein the mass percent of cyanuric chloride is 1˜5%.
9. The method according to claim 4, wherein the halogenation solution contains the active halogen including sodium hypochlorite, sodium bromate or calcium hypochlorite solution, and the mass percent is from 0.01 to 5%.
US14/768,450 2013-02-22 2014-02-17 The preparation of N-halamine antibacterial materials based on cyanuric chloride Abandoned US20160076194A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201310056994.4 2013-02-22
CN201310056994.4A CN103147288B (en) 2013-02-22 2013-02-22 Method for preparing halamine antibacterial material based on cyanuric chloride
PCT/CN2014/072161 WO2014127713A1 (en) 2013-02-22 2014-02-17 Method for preparing cyanuric chloride-based halogenoamine antibacterial material

Publications (1)

Publication Number Publication Date
US20160076194A1 true US20160076194A1 (en) 2016-03-17

Family

ID=48545586

Family Applications (1)

Application Number Title Priority Date Filing Date
US14/768,450 Abandoned US20160076194A1 (en) 2013-02-22 2014-02-17 The preparation of N-halamine antibacterial materials based on cyanuric chloride

Country Status (3)

Country Link
US (1) US20160076194A1 (en)
CN (1) CN103147288B (en)
WO (1) WO2014127713A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111041829A (en) * 2019-12-30 2020-04-21 华侨大学 Preparation method of reactive chitosan-based fabric antibacterial agent
CN111686696A (en) * 2020-04-22 2020-09-22 杭州嘉澍环境监测有限公司 Aminobenzene sulfonic acid modified glutaraldehyde cross-linked chitin gel material, preparation thereof and application thereof as noble metal gold adsorption material
CN114381073A (en) * 2021-12-15 2022-04-22 楷模居品(江苏)有限公司 Anti-ultraviolet aging chitosan-polyvinyl chloride wood-plastic plate and preparation method thereof
CN114672998A (en) * 2022-04-12 2022-06-28 福州大学 Preparation method of antibacterial and mildewproof polypropylene
CN114775264A (en) * 2022-04-22 2022-07-22 安徽大学 Method for preparing N-halamine type antibacterial cotton fabric by ATRP (atom transfer radical polymerization) method
CN116356563A (en) * 2023-02-21 2023-06-30 江苏箭鹿毛纺股份有限公司 Antibacterial fabric and preparation method thereof

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103147288B (en) * 2013-02-22 2015-03-11 江南大学 Method for preparing halamine antibacterial material based on cyanuric chloride
CN104140475B (en) * 2014-08-06 2017-01-18 上海工程技术大学 Method for preparing quaternization chitosan
US10897905B2 (en) 2016-01-26 2021-01-26 Metrex Research, LLC Hypochlorite based hard surface disinfectants
US10986841B2 (en) 2018-11-06 2021-04-27 The Clorox Company Bleach compositions
US11845916B2 (en) 2020-06-24 2023-12-19 The Clorox Company Burstable sporicidal cleaning wipe system containing stabilized hypochlorite
CN115322267B (en) * 2022-07-14 2023-10-24 四川大学 Preparation method of biomass-based amphoteric synthetic tanning agent
CN115888834B (en) * 2022-10-31 2024-07-19 南京邮电大学 Metal organic framework photocatalytic bactericide grafted with N-halamine and preparation method and application thereof
CN117385490B (en) * 2023-11-02 2024-08-16 中拓特纺(常州)纺织科技有限公司 Antibacterial fabric based on modified polyester fiber

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1096169A (en) * 1996-09-20 1998-04-14 Toyobo Co Ltd Skin care fiber product and its production

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06341073A (en) * 1994-01-10 1994-12-13 Kunio Mori Adherent composite material of steel wire and rubber
CN101215267B (en) * 2007-12-26 2011-04-27 东华大学 Ultraviolet ray absorbent with double reaction active groups used for cotton, preparation and application thereof
CN101250815A (en) * 2008-03-24 2008-08-27 王加旺 Method for manufacturing halogen amine antimicrobial material
CN102797150B (en) * 2012-08-17 2014-04-30 江南大学 Halamine antibacterial agent, its preparation method and application
CN103147288B (en) * 2013-02-22 2015-03-11 江南大学 Method for preparing halamine antibacterial material based on cyanuric chloride

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1096169A (en) * 1996-09-20 1998-04-14 Toyobo Co Ltd Skin care fiber product and its production

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Chen, Zhaobin, Jie Luo, and Yuyu Sun. "Biocidal efficacy, biofilm-controlling function, and controlled release effect of chloromelamine-based bioresponsive fibrous materials." Biomaterials 28.9 (2007): 1597-1609. *
Machine translation for JP-H10-96169, original document published April 1998 *
SciFinder abstract for Higaki et al.; Gijutsu 37(10) 597-601, 2002 *
SciFinder Abstract for JP-H10-96169, original document published April 1998 *
SIDS Initial Assessment Report For SIAM 13 Bern, Switzerland, 6-9 November 2001 on cyanuric chloride *
Yan, Zhi, et al. "Kinetics of cyanuric chloride hydrolysis in aqueous solution." Industrial & Engineering Chemistry Research 47.15 (2008): 5318-5322. *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111041829A (en) * 2019-12-30 2020-04-21 华侨大学 Preparation method of reactive chitosan-based fabric antibacterial agent
CN111686696A (en) * 2020-04-22 2020-09-22 杭州嘉澍环境监测有限公司 Aminobenzene sulfonic acid modified glutaraldehyde cross-linked chitin gel material, preparation thereof and application thereof as noble metal gold adsorption material
CN114381073A (en) * 2021-12-15 2022-04-22 楷模居品(江苏)有限公司 Anti-ultraviolet aging chitosan-polyvinyl chloride wood-plastic plate and preparation method thereof
CN114672998A (en) * 2022-04-12 2022-06-28 福州大学 Preparation method of antibacterial and mildewproof polypropylene
CN114775264A (en) * 2022-04-22 2022-07-22 安徽大学 Method for preparing N-halamine type antibacterial cotton fabric by ATRP (atom transfer radical polymerization) method
CN116356563A (en) * 2023-02-21 2023-06-30 江苏箭鹿毛纺股份有限公司 Antibacterial fabric and preparation method thereof

Also Published As

Publication number Publication date
CN103147288B (en) 2015-03-11
CN103147288A (en) 2013-06-12
WO2014127713A1 (en) 2014-08-28

Similar Documents

Publication Publication Date Title
US20160076194A1 (en) The preparation of N-halamine antibacterial materials based on cyanuric chloride
Cheng et al. Antimicrobial coating of modified chitosan onto cotton fabrics
KR100519551B1 (en) A microbiocidal textile, a textile material, a microbiocidal textile precursor, cotton fabric and a process for prparing them
Jiang et al. Synthesis of novel reactive N-halamine precursors and application in antimicrobial cellulose
JP2020002523A5 (en)
Zhou et al. Plasma-assisted regenerable chitosan antimicrobial finishing for cotton
CN101871167B (en) Preparation method of antibacterial cellulose fabric
CN102877287A (en) Preparation method of halamine-containing antibacterial cellulose fabric
CN105613506A (en) Haloamine/quaternary ammonium olefin antibacterial agent and application of antibacterial agent to biodegradable nanofiber material
US20080102217A1 (en) Process for anti-microbial textiles treatment
CN112647294B (en) Antibacterial cotton fabric with excellent washing fastness and preparation process thereof
CN102875536A (en) Halamine antibacterial agent and synthetic method and application thereof
JP2014525481A5 (en)
Zhang et al. Synthesis of antibacterial N‐halamine acryl acid copolymers and their application onto cotton
CN110644235B (en) Preparation method and application of anti-ultraviolet and antibacterial silk fabric
WO2017063091A1 (en) Compounds, polymers and coating formulations that comprise at least one n-halamine precursor, a cationic center and a coating incorporation group
JP2001278716A (en) Antimicrobial agent for fiber and antimicrobial fiber product
CN111455493A (en) Antibacterial and antiviral fabric and preparation method and application thereof
WO2016043202A1 (en) Method for producing antibacterial/antifungal processed product, and antibacterial/antifungal processed product obtained thereby
Ma et al. N-halamine modified polyester fabrics: preparation and biocidal functions
CN103058945A (en) Halide amine antibacterial agent based on cyanuric acid and synthesis method and application thereof
CN113373691B (en) Preparation method and application of cationic modifier TCTAC
CN106906658A (en) Halogen amine grafting Nature Fibre Textile product and preparation method and application
CN103598187A (en) Carboxylic acid halide amine antibacterial agent as well as synthetic method and application thereof
CN103696229A (en) Fabric setting antibiotic finishing technology based on radiation curing

Legal Events

Date Code Title Description
AS Assignment

Owner name: JIANGNAN UNIVERSITY, CHINA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:REN, XUEHONG;MA, KAIKAI;REEL/FRAME:036353/0114

Effective date: 20150810

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION