WO2002030204A1 - Antibacterial agents, and antibacterial and deodorizing solution comprising the same - Google Patents

Antibacterial agents, and antibacterial and deodorizing solution comprising the same Download PDF

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Publication number
WO2002030204A1
WO2002030204A1 PCT/KR2001/000766 KR0100766W WO0230204A1 WO 2002030204 A1 WO2002030204 A1 WO 2002030204A1 KR 0100766 W KR0100766 W KR 0100766W WO 0230204 A1 WO0230204 A1 WO 0230204A1
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WO
WIPO (PCT)
Prior art keywords
silver
antibacterial
water
compounds
complex
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.)
Ceased
Application number
PCT/KR2001/000766
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English (en)
French (fr)
Inventor
Sung Soo Kim
In-Hwan Park
Byung Chul Shin
Soo Hong Lee
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Korea Research Institute of Chemical Technology
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Korea Research Institute of Chemical Technology
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 Korea Research Institute of Chemical Technology filed Critical Korea Research Institute of Chemical Technology
Priority to EP01930295A priority Critical patent/EP1330164B1/en
Priority to JP2002533657A priority patent/JP2004510794A/ja
Priority to DE60120451T priority patent/DE60120451D1/de
Priority to AT01930295T priority patent/ATE311750T1/de
Publication of WO2002030204A1 publication Critical patent/WO2002030204A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders

Definitions

  • the present invention relates to novel antibacterial agents wherin the lone pair electrons of nitrogen atoms of amine compounds with high boiling point or water-soluble polymer with basic nitrogen at the backbone or side chain are coordinated with silver ion, and antibacterial and deodorizing solution comprising them.
  • Bacteria and molds produce low-molecular compounds emitting offensive odor by decomposing organic compounds like food with the secretion of enzymes. Also, bacteria and molds are sources of offensive odor in clothes, shoes, basement, pets and ditches. Accordingly, there have been continuous attempts to develop antibacterial and deodorizing agents which are effective for deodorization, agricultural deodorizing agent, skin-related antibacterial agent, green algae prevention and cockroach extermination by exterminating microbes like bacteria.
  • General organic antibacterial agents among currently used antibacterial agents, exterminate microbes by infiltrating into the microbial body and transforming its DNA. So, there is a possibility to generate resistant microbes.
  • silver (Ag) compounds exterminate microbes by disturbing the electron-transfer system of the cell membrane outside the microbial body, there is no concern of resistant microbes. Also, there is another advantage that many silver (Ag) compounds usable for antibacterial agents have much lower toxicity than general organic antibacterial agents.
  • silver (Ag) compounds have good antibacterial effect and lower toxicity compared with organic antibacterial agents, and does not induce the generation of resistant microbes.
  • insoluble silver (Ag) compounds like silver chloride (AgCl) and silver iodide (Agl) form uniform colloids and exist in ionic phase in water, precipitates are formed with time due to the inter-colloidal bond. So, they cannot be used in spray or solution form, and therefore the antibacterial effect becomes insufficient.
  • Soluble silver (Ag) compounds form insoluble salts like silver chloride or silver sulfide by binding with chloride or sulfate ion generally present in water. These silver compounds transform to silver metal through reduction and oxidation by light, and then blackens to silver oxide. If soluble silver (Ag) compounds are dissolved in pure water, the discoloration is delayed. But, color changes after long-time exposure to light. Accordingly, these soluble silver (Ag) compounds are not suitable for use as everyday antibacterial agents.
  • silver dichloride (AgCl ) by adding silver salt in chloride salts such as ammonium chloride, alkali metal chloride or alkaline earth metal chloride solution [International Patent Publication W099/ 09833].
  • chloride salts such as ammonium chloride, alkali metal chloride or alkaline earth metal chloride solution
  • International Patent Publication W099/ 09833 silver monochloride which discolors in light is not formed when the concentration of chloride salts is at least 60 times larger than that of silver salt. Accordingly, it is not suitable for spray -type antibacterial agent since it can induce discomfort or ski irritation due to the too high salt concentration.
  • silver compounds cannot be used for oral antibiotics because they are not absorbed well into the body, they can be used for antibacterial agents not required to be absorbed into the body, e.g. for the treatment of skin diseases and burns caused by bacteria and molds, since they have a wide antibacterial spectrum.
  • general soluble silver compounds have problems of discoloration tlirough the binding with skin protein, and insoluble silver compounds are not suitable for use as antibacterial agents due to their low antibacterial effect.
  • silver compounds are easily discolored by light, they may cause discoloration or stain when used for everyday antibacterial agents. Their colors also change when they are dissolved in water to be used for spray, skin-related antibacterial agent, agricultural fungicide, etc.
  • the cause of discoloration is that silver ion is reduced to silver metal by light, and then this silver metal is oxidized to silver oxide by the ambient oxygen.
  • the silver compounds can discolor skins when used as skin-related antibacterial agents.
  • the reduction-oxidation reactions of soluble silver compounds in pure water without anions like distilled water proceed slowly, and therefore the discoloration time is rather long.
  • general industrial water and tap water contain anions like chloride ion or sulfate ion, and they react with silver compounds to produce insoluble silver chloride or silver sulfide.
  • These insoluble silver compounds reduce to silver metal due to the light energy of UN etc., and then oxidize by ambient oxygen to produce silver oxide and discolor the solution. So, they are not suitable for use as antibacterial deodorizing agent, agricultural antibacterial agent, green algae inhibitor, etc.
  • the soluble silver compounds may discolor the skin by binding with the skin protein and producing silver oxide when they are used for skin-related treatments.
  • the inventors made efforts to resolve the problems of discoloration due to light and skin discoloration while utilizing the unique antibacterial effect, low toxicity and nonresistance of silver compounds or silver ions.
  • aiming at the properties of silver (Ag) compounds and silver ions we prepared silver complex with novel structure.
  • This novel compounds has superior antibacterial effect, low toxicity, good solubility to water and stable silver ion. So, since it neither discolors by light nor discolors the skin, it can be prepared as antibacterial deodorizing solution suitable for antibacterial agents for clothes or skin treatment.
  • an object of the present invention is to provide novel antibacterial agents and antibacterial and deodorizing solution comprising them, which have superior antibacterial effect and low toxicity, and hardly discolor by light.
  • FIG. 1 is a photograph which shows the discoloration of the silver nitrate solution and silver-polyethyleneimine complex solution after exposing them for 2hr in UN.
  • FIG. 2 is a photograph which shows the behavior of cockroaches in the part where 2% -diluted solution of silver-polyethyleneimine complex was sprayed and in the non-treated part.
  • the present invention is characterized by a silver complex antibacterial agent wherin the lone pair electrons of nitrogen atoms of amine compounds with high boiling point or water-soluble polymer with basic nitrogen at the backbone or side chain are coordinated with silver ion.
  • Another characteristic of the present invention is an antibacterial and deodorizing solution comprising the said silver complex antibacterial agent.
  • the present invention relates to: a silver complex antibacterial agent which stabilizes silver ion to prevent its reaction with anions like chloride ion. or sulfate ion present in water and prevents the reduction-oxidation reaction, and therefore does not discolor in general water other than distilled water; and antibacterial and deodorizing solution comprising it.
  • Formula (1) represents a silver complex wherein the polyethyleneimine polymer is coordinated with silver ion, and it is a typical example of many antibacterial agents included in the present invention.
  • ammonia NH3
  • the silver complex according to the present invention provides the silver ion stabilization effect as in the addition of ammonia (NH3) and does not emit the offensive odor. So, it is useful for spray-type antibacterial and deodorizing agent.
  • amine compounds with high boiling point or water-soluble polymers with plenty of basic nitrogen atoms having lone pair electrons at the polymer backbone or side chain are used.
  • the amine compounds with high boiling point are adequate for the purpose of the present invention since they emit hardly any offensive odor.
  • any amine compounds with high boiling point of the present invention including monoethanolamine, diethanolamine and triethanolamine can be used. And, they are not limited to the said examples.
  • any water-soluble polymers including polyvinylamine, polyarylamine, polyethyleneimine, polyhexamethylenebiguanidine and polyvinylpyridine. And, they are not limited to the said examples.
  • polyethylene glycol, polyvinylalchol, polyacrylamide, polyvinylpyrrolidone and polyvinylacrylic acid did not prevent the formation of silver chloride (AgCl), nor did not prevent the photo-discoloration of the solution. Accordingly, amine or imine compounds with basic nitrogen atoms having lone pair electrons are recommended for the strong coordination with the silver ion.
  • the water-soluble polymer with basic nitrogen atom having lone pair electrons at the backbone or side chain of the present invention can be prepared by mixing vinylamine, arylamine, ethyleneimine or vinylpyridine in organic solvents like benzene and toluene in the range of 5-20%, and radical-polymerizing them at 60-80 ° C for 12-24 hrs using BPO as an initiator.
  • the water-soluble silver compound especially soluble in ammonia water
  • the silver compound with low toxicity is more recommendable for the purpose of the present invention.
  • silver nitrate, silver acetate, silver sulfate, silver benzoate, silver salicylate, silver thiosalicylate or silver sulfadiazine are such silver compounds.
  • a content of silver compounds in the antibacterial agent according to the present invention is in the range of 5-50wt% of the water-soluble polymers with basic nitrogen atoms having lone pair electrons at the polymer backbone or side chain. This content can be adjusted by adjusting the number of lone pair electrons of the basic nitrogen containing amine compounds or polymers.
  • the present invention includes an antibacterial and deodorizing solution comprising the said silver complex as effective component.
  • the antibacterial agent according to the present invention is highly soluble in water, water or mixture of water and alcohol can be used for the solvent, and the solvent can be selected depending on the purpose of use.
  • the preparation method of the antibacterial and deodorizing solution or the effective content of the antibacterial agent is not limited specifically.
  • the common additives such as sodium benzoate, sodium salicylate or colloidal silica can be included. And other additives can be easily used with the common knowledge in the art.
  • the silver complex according to the present invention easily forms complex with offensive-smelling compound or pollutant like dioxin, and prevents its vaporization. So, it helps to prevent offensive odor and environmental pollution. Especially, because silver (Ag) compounds easily forms complex with amine and thiol compounds, they can easily remove amine and thiol offensive-smelling compounds. Accordingly, since the antibacterial and deodorizing solution containing these silver complexes as effective component have superior antibacterial effect, they are useful for the removal of offensive odor caused by microbes like bacteria and molds. Also, they help to prevent the environmental pollution since they prevent the vaporization of offensive-smelling compounds and environmental pollutants by forming complex.
  • the silver antibacterial and deodorizing solution of the present invention is useful for the treatment of burns, prevention and treatment of bedsore and treatment of dermatitis because it provides no resistance and very low toxicity.
  • the antibacterial agent of the present invention is suitable for the use as skin-related treatment in spray, ointment or gel form because it forms complex with amine polymers and the silver is kept in ionic form.
  • the silver complex antibacterial agent of the present invention can be applied for the fungicide of vegetables and crops or green algae inhibitor of aquarium because they have superior exterminating effect of molds and algae.
  • microbes proliferate in the stems of flowers with stems, which disturb the supply of nutrients and water through stem and therefore wilt the flowers.
  • the antibacterial agent of the present invention extends the life of flowers by preventing the bacterial infection.
  • the silver complex antibacterial agent of the present invention is also useful for the extermination, of insects like cockroaches. Though its cause is not certain as yet, it may be because the insects have poor digestive function compared with higher animals and can only digest low-molecular weight organic materials. Namely, if the antibacterial agent of the present invention is sprayed on food, the insects may avoid it because they cannot digest it due to the inhibition of microbial growth.
  • Example 2 Silver-polyhexamethylenebiguanidine complex After adding 5g of polyhexamethylenebiguanidine in IL of water, 2g of silver benzoate, lOg of sodium benzoate and lg of sodium salicylate were slowly added while stirring. After stirring sufficiently for 24hr, polyhexamethylenebiguanidine complex containing silver salt was obtained.
  • Example 5 Silver-diethanolamine complex After adding lOg of diethanolamine in aqueous alcohol solution comprising 800mL of water and 200mL of ethanol, and dissolving it completely, 2g of silver nitrate, lOg of sodium benzoate and lg of sodium salicylate were slowly added while stirring. After stirring sufficiently for 24hr, diethanolamine complex containing silver salt was obtained.
  • the silver complexes obtained in the above Examples 1-5 were diluted to 2% (containing 10-40ppm of silver ion) with tap water.
  • Silver compounds including silver nitrate, silver sulfide, silver acetate and silver benzoate were dissolved in tap water to 40ppm to be used as contrast groups.
  • the general silver compound solution forms white colloids and then black precipitates afterwards.
  • the silver complex of the present invention shows little photo-discoloration.
  • the minimum growth inhibition concentration was measured using test-tube dilution method in order to evaluate the antibacterial activity of the silver complexes obtained in Examples 1-5. The result is shown in the following Table 2.
  • the samples used for antibacterial effect evaluation test were lg respectively, and their size was lOXlOXlmm 3 .
  • the antibacterial effect evaluation test followed the bacteria count method (KS K 0693) using E. coli ATCC 25922 and Staphylococcus aureus ATCC 6538.
  • the bacteria culture time was 24hr.
  • the base sample used for fungus resistance evaluation test was 30X30Xlmm 3 .
  • the fungus resistance evaluation test followed the mold resistance test method (KS A 0702) using ATCC 10254 (Aspergillus niger ATCC 10254) black mold.
  • the bacteria culture time was 2 weeks.
  • the mold resistance is presented in the following Table 4.
  • the silver complexes according to the present invention have superior mold resistance of 3.
  • the fungus resistance was investigated with the same method in Experimental Example 4 to evaluate its efficiency. As a result, it showed very superior antibacterial effect with rating 3.
  • the antibacterial agent of the present invention is a silver complex wherein the lone pair electrons of nitrogen atom in the amine compounds with high boiling point or water-soluble polymers with basic nitrogen are coordinated with silver ion, and it has superior discoloration resistance and antibacterial effect, and highly soluble in water.

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PCT/KR2001/000766 2000-10-09 2001-05-11 Antibacterial agents, and antibacterial and deodorizing solution comprising the same Ceased WO2002030204A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP01930295A EP1330164B1 (en) 2000-10-09 2001-05-11 Antibacterial agents and antibacterial and deodorizing solution comprising the same
JP2002533657A JP2004510794A (ja) 2000-10-09 2001-05-11 新規抗菌剤およびそのような抗菌剤を含有する抗菌脱臭性溶液
DE60120451T DE60120451D1 (de) 2000-10-09 2001-05-11 Antibakterielle mittel sowie diese enthaltende antibakterielle und deodorierende lösung
AT01930295T ATE311750T1 (de) 2000-10-09 2001-05-11 Antibakterielle mittel sowie diese enthaltende antibakterielle und deodorierende lösung

Applications Claiming Priority (2)

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KR2000/59345 2000-10-09
KR10-2000-0059345A KR100411178B1 (ko) 2000-10-09 2000-10-09 신규 항균제와 이러한 항균제를 함유하는 항균탈취성 용액

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EP (1) EP1330164B1 (cg-RX-API-DMAC7.html)
JP (1) JP2004510794A (cg-RX-API-DMAC7.html)
KR (1) KR100411178B1 (cg-RX-API-DMAC7.html)
AT (1) ATE311750T1 (cg-RX-API-DMAC7.html)
DE (1) DE60120451D1 (cg-RX-API-DMAC7.html)
WO (1) WO2002030204A1 (cg-RX-API-DMAC7.html)

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EP1584235A3 (en) * 2004-04-08 2006-05-10 Rohm And Haas Company Antibacterial composition containing a metal complexed with a polymer
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US7754197B2 (en) 2003-10-16 2010-07-13 Kimberly-Clark Worldwide, Inc. Method for reducing odor using coordinated polydentate compounds
WO2009150090A3 (de) * 2008-06-12 2010-11-18 Basf Se Kosmetische zubereitungen zur verminderung des hautgeruchs
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US8604073B2 (en) 2006-03-27 2013-12-10 Ethicon, Inc. Antimicrobial composition
US8840876B2 (en) 2005-05-19 2014-09-23 Ethicon, Inc. Antimicrobial polymer compositions and the use thereof
WO2014191631A3 (en) * 2013-05-28 2015-04-09 Argen Lab Oy Low alcohol content disinfection foams
WO2017049453A1 (en) * 2015-09-22 2017-03-30 Rohm And Haas Company Polymer emulsion and antimicrobial coating composition comprising the same
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JP4611722B2 (ja) * 2004-11-30 2011-01-12 ライオン株式会社 抗菌性液体組成物およびその製造方法
JP2006151908A (ja) * 2004-11-30 2006-06-15 Lion Corp ヌメリ抑制用組成物およびヌメリ抑制方法
FR2881656B1 (fr) * 2005-02-09 2007-04-13 Eastman Kodak Co Procede pour controler la croissance microbienne
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DE602006000082T2 (de) 2005-07-07 2008-05-15 Rohm And Haas Co. Faser mit antimikrobiell wirksamer Zusammensetzung
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JP5473740B2 (ja) * 2010-04-20 2014-04-16 ライオン株式会社 硬表面用液体洗浄剤組成物
JP5603702B2 (ja) * 2010-08-02 2014-10-08 株式会社Ｊ−ケミカル 抗菌性組成物及びその用途
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JP5787587B2 (ja) * 2011-04-18 2015-09-30 株式会社ネオス 塩素イオンを含有する溶液中でヒスチジン銀錯体の殺菌活性を維持する方法および液状抗菌剤組成物
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US8901188B2 (en) * 2011-06-16 2014-12-02 Kimberly-Clark Worldwide, Inc. Antimicrobial polyurethane foam and process to make the same
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JP6262434B2 (ja) * 2013-02-12 2018-01-17 小林製薬株式会社 肌着用の抗菌スプレー剤組成物
US11618696B2 (en) 2013-08-15 2023-04-04 Applied Silver, Inc. Antimicrobial batch dilution system
US10640403B2 (en) 2013-08-15 2020-05-05 Applied Silver, Inc. Antimicrobial batch dilution system
US9689106B2 (en) 2013-12-06 2017-06-27 Applied Silver, Inc. Antimicrobial fabric application system
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EP1330164B1 (en) 2005-12-07
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US20030190370A1 (en) 2003-10-09

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