WO2012144475A1 - Procédé de conservation du pouvoir bactéricide d'un complexe histidine-argent dans une solution comprenant des ions chlore, et composition antibactérienne liquide - Google Patents

Procédé de conservation du pouvoir bactéricide d'un complexe histidine-argent dans une solution comprenant des ions chlore, et composition antibactérienne liquide Download PDF

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Publication number
WO2012144475A1
WO2012144475A1 PCT/JP2012/060297 JP2012060297W WO2012144475A1 WO 2012144475 A1 WO2012144475 A1 WO 2012144475A1 JP 2012060297 W JP2012060297 W JP 2012060297W WO 2012144475 A1 WO2012144475 A1 WO 2012144475A1
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Prior art keywords
histidine
water
liquid
acid
silver complex
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English (en)
Japanese (ja)
Inventor
直士 大川
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Neos Co Ltd
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Neos Co Ltd
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    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • 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

Definitions

  • the present invention relates to a liquid antibacterial agent composition containing a histidine silver complex having excellent antibacterial properties against a wide range of microorganisms even in the presence of chloride ions, and a method for producing the same, and a process for producing foods, cosmetics and pharmaceuticals,
  • the present invention relates to a liquid antibacterial agent composition useful in many fields such as sanitation and industrial products, and a method for producing the same.
  • this invention relates to the technique of maintaining the bactericidal activity of the histidine silver complex in a chloride ion containing liquid.
  • benzimidazole nitrile, isothiazoline, haloallylsulfone, iodopropargyl, benzoazole
  • Antibacterial agents such as those based on phenol, phenol, pyridine, diphenyl ether and chlorhexidine are used.
  • the efficacy and safety of antibacterial agents are generally contradictory, and strong antibacterial agents are often harmful to the human body. For this reason, when using an antibacterial agent, it is necessary to consider the influence on a human body.
  • Silver is known to be strong and safe. However, since silver ions form insoluble salts with carboxylic acids and chlorine ions, it is difficult to use silver as a liquid disinfectant. As a method for solving this problem, it has been proposed to use silver as a complex with imidazole and its derivatives, histidine, aspartic acid, 2-pyrrolidone-5-carboxylic acid, and 5-oxo-2-tetrafurancarboxylic acid. (Patent Documents 1 to 5). In particular, it has been reported that a silver complex formed by coordination of histidine or 2-pyrrolidone-5-carboxylic acid with a silver ion is water-soluble and stable.
  • the silver histidine complex cannot be stably present for a long time when dissolved in water, and has a problem of causing severe discoloration.
  • a method for solving this problem a method of increasing the histidine / silver to 3 or more and a method of adding hydroxycarboxylic acids and polyvalent carboxylic acids have been proposed (Patent Documents 6 and 7).
  • Patent Documents 6 and 7 a method of adding hydroxycarboxylic acids and polyvalent carboxylic acids.
  • a solution containing chlorine ions such as tap water, there is a problem that the insoluble salt is formed with the chlorine ions and the efficacy is lost.
  • the present invention is to provide a method for maintaining the bactericidal activity of a histidine silver complex in a liquid containing chlorine ions, a liquid additive composition, a liquid antibacterial agent composition, and a method for producing the same.
  • the present inventor conducted extensive research to solve the above problems, and found that the addition of a water-soluble nitrogen-containing polymer stabilizes the histidine silver complex and prevents reaction with chloride ions.
  • the present invention has been completed based on such knowledge, and provides a method for maintaining the bactericidal activity of the silver histidine complex of the following aspect, a liquid additive composition, a liquid antibacterial agent composition, and a method for producing the same. It is.
  • Item 1 A method for maintaining the bactericidal activity of a histidine silver complex in a chloride ion-containing liquid, comprising adding a water-soluble nitrogen-containing polymer.
  • Item 2 A method for maintaining the bactericidal activity of a histidine silver complex in a chloride ion-containing liquid, comprising adding a water-soluble nitrogen-containing polymer.
  • a liquid additive composition for maintaining the activity of a silver histidine complex in a chloride ion-containing liquid comprising at least one water-soluble nitrogen-containing polymer.
  • Item 3. A liquid antibacterial composition containing a histidine silver complex, one or more water-soluble nitrogen-containing polymers and a solvent.
  • Item 4. Item 4. The method according to Item 1, the activity maintaining agent according to Item 2, or the liquid antibacterial agent composition according to Item 3, wherein the water-soluble nitrogen-containing polymer is polyethyleneimine.
  • Item 5. A method for preparing a liquid antibacterial agent composition comprising mixing (a) silver oxide, (b) L-histidine, (c) a water-soluble nitrogen-containing polymer, and (d) a solvent.
  • Item 6. Item 6. The method for preparing a liquid antibacterial agent composition according to Item 5, wherein the water-soluble nitrogen-containing polymer is a carboxylate of polyethyleneimine.
  • the histidine silver complex does not form insoluble salts with chloride ions even in a 3% sodium chloride solution, and exhibits a bactericidal effect. Therefore, in the present invention, even if the solution of the histidine silver complex contains, for example, chlorine ions having a chlorine concentration of about 2% or less, the bactericidal activity can be maintained.
  • 3% Sodium Chloride Solution In a preferred embodiment of the present invention, the composition is used by appropriately adding to an industrial product or the like, or by directly contacting the composition with an object.
  • the water-soluble nitrogen-containing polymer used in the present invention is not particularly limited as long as it forms a sparingly soluble salt with silver such as a halogen ion as a counter ion, but polyethyleneimine, polyvinylpyrrolidone, quaternized polyvinylpyrrolidone, Examples include polyvinylamine, polyallylamine, peptides (for example, polylysine, polyarginine, polyglutamic acid, polyornithine, protamine, peptone, polypeptone, etc.). Among these, polyethyleneimine is suitable for use in the present invention from the viewpoints of performance and economy.
  • the present invention provides a method for maintaining the bactericidal activity of a histidine silver complex in a chloride ion-containing liquid, wherein a water-soluble nitrogen-containing polymer is added to the histidine silver complex.
  • the histidine silver complex in order to maintain the bactericidal activity of the histidine silver complex in a liquid containing chlorine ions, is preferably used as a liquid additive composition in which the water-soluble nitrogen-containing polymer is dissolved in an appropriate solvent. May be added individually, or a liquid antibacterial composition obtained by mixing them may be added.
  • the weight ratio of the water-soluble nitrogen-containing polymer used in the present invention to the histidine silver complex is not limited because it varies depending on the type of polymer used, but in the case of polyethyleneimine, which is a representative example, 5 to 5 parts per 1 part by weight of the histidine silver complex. 500 parts by weight, preferably 20 to 200 parts by weight, more preferably 50 to 100 parts by weight.
  • polyethyleneimine is added at a smaller ratio, the effect of preventing the reaction between the histidine silver complex and chloride ions is insufficient, and the effect is increased even when polyethyleneimine is added at a larger ratio. There is no.
  • the content of the water-soluble nitrogen-containing polymer in the liquid additive composition in the present invention is 1 to 50% by weight, preferably 5 to 40% by weight, more preferably 10 to 30% by weight in the case of the polyethyleneimine of the representative example. is there.
  • a solvent can be added to the liquid additive composition. Solvents include water, glycerin, methanol, ethanol, propanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, triethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl.
  • Ether ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, glycerin monomethyl ether, glycene monoethyl ether, glycerin monopropyl ether, Glycene monobuchi Ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, diglycerin monomethyl ether, diglycerin monoethyl ether, diglycerin monopropyl ether, diglycerin mono Examples include butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, and water is preferable.
  • liquid antibacterial agent composition of the present invention a histidine silver complex and a water-soluble nitrogen-containing polymer are blended in the above ratio.
  • the amount of polyethyleneimine added to the liquid antibacterial agent composition is 1 to 50% by weight, preferably 5 to 30% by weight, and more preferably 10 to 20% by weight.
  • the liquid antibacterial agent composition contains a solvent together with a histidine silver complex and a water-soluble nitrogen-containing polymer.
  • Solvents contained in the liquid antibacterial agent composition include water, glycerin, methanol, ethanol, propanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, triethylene glycol, ethylene Glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, glycerin monomethyl ether, glycene mono Ethyl ether, glycerol monopropyl Ether, glycene monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, dipropylene glycol monomethyl ether, diprop
  • the pH of the liquid additive composition and the liquid antibacterial agent composition is not particularly limited, but is preferably pH 6 to 8.
  • a carboxylic acid is used. Is added.
  • the carboxylic acid used for neutralization include acetic acid, propionic acid, glycolic acid, lactic acid, pyruvic acid, tartronic acid, glyceric acid, malic acid, tartaric acid, citric acid, isocitric acid, oxalic acid, malonic acid, and itaconic acid.
  • Adipic acid succinic acid, fumaric acid, glutaric acid and the like.
  • the liquid antibacterial agent composition of the present invention is prepared by mixing a histidine silver complex solution and an aqueous solution of a water-soluble nitrogen-containing polymer (for example, carboxylic acid of polyethyleneimine), or when preparing a histidine silver complex (for example, it can be prepared by adding a polyethyleneimine carboxylate).
  • a water-soluble nitrogen-containing polymer for example, carboxylic acid of polyethyleneimine
  • liquid antibacterial agent composition of the present invention are not particularly limited as long as it is intended to have an antibacterial action against microorganisms.
  • industrial products such as paints, inks, water-soluble cutting fluids, foods and cosmetics ⁇ Used in pharmaceutical manufacturing process detergents, tableware sterilization washings, mouth washings, hand washings, antibacterial paper and antibacterial fibers, deodorant / antibacterial sprays, slime control agents in papermaking processes, etc. Can be mentioned.
  • a surfactant in the liquid antibacterial agent composition of the present invention, a surfactant, a chelating agent, a humectant, a thickener and the like can be appropriately added.
  • the surfactant used in the present invention is not particularly limited.
  • the anionic surfactant include fatty acid soap (for example, sodium laurate, sodium palmitate), higher alkyl sulfate ester salt (for example, POE- Lauryl sulfate triethanolamine, POE-sodium lauryl sulfate, etc.), higher fatty acid amide sulfonates (for example, N-myristoyl-N-methyl taurine sodium, coconut oil fatty acid methyl tauride sodium, etc.), phosphate ester salts (for example, POE-sodium oleyl ether phosphate, POE-stearyl ether phosphate, etc.), sulfosuccinate (eg, dioctyl sodium sulfosucc
  • Nonionic surfactants include, for example, sorbitan fatty acid esters (for example, sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmite, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate).
  • sorbitan fatty acid esters for example, sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmite, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate.
  • Glycerin fatty acid esters for example, glyceryl monoerucate, glyceryl sesquioleate, glyceryl monosaleate
  • propylene glycol fatty acid esters for example, propylene glycol monostearate
  • hardened castor oil derivatives for example, glycerin alkylate
  • POE -Sorbitan esters eg POE-sorbitol laurate, POE-sorbitol monooleate, POE-sorbitan monostearate, etc.
  • PO Fatty acid esters POE-alkyl ethers (eg POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, etc.), Pluronics, POE • POP-alkyl ethers (eg POE • POP-monocetyl ether) , POE / POP-monobutyl ether, POE / POP-glycerin ether, etc
  • Examples of the cationic surfactant include alkyltrimethylammonium salts (for example, stearyltrimethylammonium chloride, lauryltrimethylammonium chloride, etc.), alkylpyridinium salts (for example, cetylpyridinium chloride, etc.), distearyldimethyldiammonium chloride, dialkyl.
  • alkyltrimethylammonium salts for example, stearyltrimethylammonium chloride, lauryltrimethylammonium chloride, etc.
  • alkylpyridinium salts for example, cetylpyridinium chloride, etc.
  • distearyldimethyldiammonium chloride dialkyl.
  • Examples include dimethylammonium salt, alkyl quaternary ammonium salt, alkyldimethylbenzylammonium salt, dialkylmorphonium salt, POE-alkylamine, alkylamine salt, polyamine fatty acid derivative, amino alcohol fatty acid derivative,
  • amphoteric surfactants examples include imidazoline-based amphoteric surfactants (eg, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide). Side-1-carboxyethyloxy disodium salt), betaine surfactants (for example, 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, amide betaine, lauric acid And amidopropylhydroxysulfobetaine).
  • imidazoline-based amphoteric surfactants eg, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide.
  • Side-1-carboxyethyloxy disodium salt
  • chelating agents include ethylenediaminetetraacetic acid, nitrilotriacetic acid, 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium ethetate, trisodium edetate Edetate tetrasodium, sodium citrate, sodium polyphosphate, potassium pyrophosphate, ascorbic acid, gluconic acid, citric acid, succinic acid, adipic acid, suberic acid, and the like.
  • thickeners examples include gum arabic, carrageenan, gum karaya, gum tragacanth, casein, dextrin, gelatin, sodium alginate, methylcellulose, ethylcellulose, CMC, hydroxyethylcellulose, hydroxypropylcellulose, PVA, sodium polyacrylate, guar gum, tamarind gum, Xanthan gum, magnesium aluminum silicate, bentonite, hectorite, laponite and the like can be mentioned.
  • humectant examples include polyethylene glycol, propylene glycol, glycerin, xylitol, sorbitol, maltitol and the like.
  • liquid antibacterial agent composition of the present invention can be made into a bactericidal agent suitable for each purpose by being appropriately used in combination with one or more of the additives listed above.
  • ⁇ Preparation of silver histidine complex 1.07 g of silver oxide, 2.88 g of L-histidine, 0.4 g of sodium citrate, and 95.646 g of distilled water are placed in a suitable container and stirred at room temperature for 30 minutes or more, containing 2.44% by weight of histidine silver complex. An aqueous solution was obtained.
  • ⁇ Preparation of polyethyleneimine-containing histidine silver complex Place 0.107 g of silver oxide, 0.288 g of L-histidine, 40 g of 50% by weight polyethyleneimine solution (Lugarban G35), 20 g of citric acid, and 39.605 g of distilled water in a suitable container and stir at room temperature for 30 minutes or more. An aqueous solution containing 0.244% by weight of the inventive histidine silver complex and 20% by weight of polyethyleneimine was obtained.
  • Examples 6-7, Comparative Example 3 As shown in Table 2, the polyethyleneimine-containing histidine silver complex solution was added to tap water, physiological saline, or 3% sodium chloride solution. After leaving these liquids for 30 minutes, the presence or absence of cloudiness of the liquids was visually observed.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention fournit un procédé de conservation du pouvoir bactéricide d'un complexe histidine-argent dans un liquide comprenant des ions chlore. Le procédé de l'invention est caractéristique du fait de l'ajout d'un polymère azoté hydrosoluble.
PCT/JP2012/060297 2011-04-18 2012-04-16 Procédé de conservation du pouvoir bactéricide d'un complexe histidine-argent dans une solution comprenant des ions chlore, et composition antibactérienne liquide Ceased WO2012144475A1 (fr)

Applications Claiming Priority (2)

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JP2011092032A JP5787587B2 (ja) 2011-04-18 2011-04-18 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
JP2011-092032 2011-04-18

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019021144A1 (fr) * 2017-07-22 2019-01-31 Rangasamy Naidu Educational Trust Procédé de préparation d'hydrogel à base de molécule de l-histidine par gélification de l'eau
WO2019021143A1 (fr) * 2017-07-22 2019-01-31 Rangasamy Naidu Educational Trust Hydrogel à base de molécules de l-histidine
CN114766520A (zh) * 2022-05-20 2022-07-22 千藤（南京）环保科技有限公司 一种柠檬酸三银组合物、制备方法及用途

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Publication number Priority date Publication date Assignee Title
JP5787589B2 (ja) * 2011-04-19 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発揮させる方法、液状添加剤組成物および液状抗菌性組成物
FI20115816L (fi) 2011-08-22 2013-02-23 Silverphase Oy Antimikrobinen ionomeerikoostumus sekä sen käyttösovellukset
JP6209169B2 (ja) 2012-02-20 2017-10-04 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ポリマーを用いた殺生物剤の抗微生物活性の増強
JP2014150865A (ja) * 2013-02-06 2014-08-25 Neos Co Ltd 液状消臭剤組成物
SG11201604975VA (en) * 2014-01-29 2016-08-30 Unilever Plc Cleansing composition containing oligodynamic metal and efficacy enhancing agent
ES2909880T3 (es) * 2015-09-30 2022-05-10 Nutrition & Biosciences Usa 1 Llc Método de preparación de una composición antimicrobiana

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JP2000256365A (ja) * 1999-03-03 2000-09-19 Meiji Milk Prod Co Ltd 水溶性銀錯体
JP2001335405A (ja) * 2000-05-23 2001-12-04 Meiji Milk Prod Co Ltd 抗菌抗かび剤
JP2004510794A (ja) * 2000-10-09 2004-04-08 コリア　リサーチ　インスティチュート　オブ　ケミカル　テクノロジー 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
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JP2005145923A (ja) * 2003-11-19 2005-06-09 National Institute Of Advanced Industrial & Technology 海洋付着菌用抗菌剤
JP2006151907A (ja) * 2004-11-30 2006-06-15 Lion Corp 抗菌性液体組成物
WO2009098850A1 (fr) * 2008-02-08 2009-08-13 Nippon Soda Co., Ltd. Composition liquide comprenant un complexe histidine-argent, composition d'un agent germicide et procédé de stabilisation d'un complexe histidine-argent

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019021144A1 (fr) * 2017-07-22 2019-01-31 Rangasamy Naidu Educational Trust Procédé de préparation d'hydrogel à base de molécule de l-histidine par gélification de l'eau
WO2019021143A1 (fr) * 2017-07-22 2019-01-31 Rangasamy Naidu Educational Trust Hydrogel à base de molécules de l-histidine
CN114766520A (zh) * 2022-05-20 2022-07-22 千藤（南京）环保科技有限公司 一种柠檬酸三银组合物、制备方法及用途

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