WO2015107934A1 - Composition d'agent antiseptique - Google Patents

Composition d'agent antiseptique Download PDF

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Publication number
WO2015107934A1
WO2015107934A1 PCT/JP2015/050117 JP2015050117W WO2015107934A1 WO 2015107934 A1 WO2015107934 A1 WO 2015107934A1 JP 2015050117 W JP2015050117 W JP 2015050117W WO 2015107934 A1 WO2015107934 A1 WO 2015107934A1
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WO
WIPO (PCT)
Prior art keywords
methyl
isothiazolin
ppm
preservative composition
added
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PCT/JP2015/050117
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English (en)
Japanese (ja)
Inventor
眞由美 古川
和彦 坂田
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ロンザジャパン株式会社
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Application filed by ロンザジャパン株式会社 filed Critical ロンザジャパン株式会社
Priority to CN201580004833.8A priority Critical patent/CN105916380A/zh
Priority to JP2015557789A priority patent/JPWO2015107934A1/ja
Publication of WO2015107934A1 publication Critical patent/WO2015107934A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • emulsions, latexes, water-based paints, water-based inks, paper coating agents, starch pastes, pigment slurries, concrete admixtures, cooling water, water treatment, water-based general household products, cosmetics, agricultural chemicals, etc. are altered by microbial contamination.
  • a preservative composition characterized by containing as an active ingredient a compound represented by ON and / or the following general formula (1).
  • the active ingredients are emulsions, latexes, water-based paints, water-based inks, paper coating agents, starch pastes, pigment slurries, concrete admixtures, cooling water, water treatment, water-based general household products, cosmetics, agricultural chemicals, and other water-based systems. It is an antiseptic that is added to industrial products and prevents deterioration and decay of products caused by microorganisms such as bacteria and fungi.
  • bactericides and preservative compositions have been used in many fields of general industrial water-based products, and are used to control harmful microorganisms such as bacteria, molds, yeasts or algae.
  • isothiazoline compounds have long been known as highly effective disinfectants and preservatives.
  • 2-methyl-4,5-trimethylene-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, and the compound represented by the general formula (1) are all known as bactericides and preservatives.
  • it has drawbacks such as insufficient bactericidal and antiseptic effects against certain types of microorganisms and lack of sustainability of effects.
  • Japanese Patent No. 2029853 describes industrial sterilization comprising 5-chloro-2-methylisothiazolin-3-one / 2-methyl-4-isothiazolin-3-one mixture and 1,2-benzisothiazolin-3-one.
  • An antiseptic composition is disclosed.
  • a synergistic industrial disinfectant / preservative composition comprising a combination of 2-methyl-4-isothiazolin-3-one and 1,2-benzisothiazolin-3-one is known as Thorhemegzelshaftmit Beschlenkterhof. It is disclosed in Tung (Thor Chemical GmbH), International Patent PCT / EP98 / 05310.
  • the object of the present invention is to synergize the active ingredient used, so that it can be used at a lower concentration compared to the concentration required when the active ingredient is used alone, Preservatives that have features such as reducing the degree of pollution caused by exposure to the environment, reducing costs, maintaining sterilization and antiseptic effects over a long period of time, and preventing shock when added to water-based industrial products. It is to provide a composition.
  • the antiseptic composition of the present invention having an antibacterial active isothiazoline-based compound, one of which is 2-methyl-4,5-trimethylene-4-isothiazolin-3-one.
  • the present invention is represented by (A) 2-methyl-4,5-trimethylene-4-isothiazolin-3-one and (B) 2-methyl-4-isothiazolin-3-one and / or the general formula (1).
  • a preservative composition characterized by comprising a compound as an active ingredient.
  • R represents an alkyl group or an allyl group having 8 to 22 carbon atoms
  • n + m represents a number of 2 to 12, preferably 3 to 10.
  • the preservative composition containing as an active ingredient has the advantage of not causing a shock when added to an aqueous industrial product because an organic solvent can be kept as low as possible in its production method. Compared with the synergistic action of the antibacterial effect by the combination of the compounds, there is an effect that the antibacterial spectrum is broadened and more antibacterial effect can be expected.
  • the preservative composition of the present invention includes emulsion paints, latex emulsions, water-based paints, metalworking oils, starch pastes, paper coating solutions, fiber oils, concrete admixtures, cooling water, water treatment, water-based general household products, cosmetics.
  • it exhibits a synergistic antiseptic effect for controlling and controlling alteration and contamination by microorganisms such as agricultural chemicals, and is effective in preventing slime damage caused by microorganisms in the papermaking process and factory cooling water system.
  • it is a useful preservative composition that is low in toxicity, has no concern about pollution, and does not adversely affect the target composition.
  • 2-Methyl-4,5-trimethylene-4-isothiazolin-3-one which is one of the active ingredients of the present composition, is, for example, skin compared to 5-chloro-2-methyl-4-isothiazolin-3-one. Irritant is notably low. In addition, it is an environmentally friendly antibacterial active substance. By using this compound as one of the active ingredients of this composition, there are no disadvantages that cause allergies to the user, and industrial wastewater. It has the advantage that it is very easy to handle in terms of legal regulations.
  • the preservative composition of the present invention comprises (A) 2-methyl-4,5-trimethylene-4-isothiazolin-3-one and (B) 2-methyl-4-isothiazolin-3-one and / or the above general formula.
  • the mixing ratio with the compound represented by (1) is preferably 50: 1 to 1:50, more preferably 20 to 1: 1 to 20, and most preferably 5 to 1: 1. .
  • the preservative composition of the present invention 2-methyl-4,5-trimethylene-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and / or represented by the above general formula (1)
  • the preservative containing the compound as an active ingredient is preferably 1.0 to 40% by weight, more preferably 2.0% by weight, based on the total amount of the preservative composition. Concentration of ⁇ 10% by weight.
  • Bisaminopropyl dodecylamine is a representative compound represented by the general formula (1).
  • the preservative composition having the composition of the present invention can be diluted with water and / or an organic solvent as necessary.
  • organic solvents include glycols such as ethylene glycol, diethylene glycol, propylene glycol and dipropylene glycol, cellsolves such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether, and carbitols such as diethylene glycol monomethyl ether and diethylene glycol monoethyl ether. Is mentioned.
  • surfactants such as nonionic surfactants such as polyoxyalkylene ether, polyoxyallyl ether, polyoxyalkylene amino ether, glycerin fatty acid ester, sorbitan fatty acid ester, fatty acid sodium, alkyl sulfate, polyoxysulfate
  • Anionic surfactants such as ethylene salts, alkylbenzene sulfonates, ⁇ -olefin sulfonates, alkyl phosphates, amphoteric surfactants such as alkyldimethylamine oxide, alkylcarboxybetaines, alkylsulfobetaines, amide amino acid salts, etc.
  • Additives such as organic acids such as succinic acid, citric acid and tartaric acid and salts thereof, known chelating agents, antifoaming agents and rust preventives can be used.
  • it may contain one or more other antibacterial active substances selected depending on the field of application. Examples of antibacterial active substances are as follows.
  • isothiazoline-based compounds such as 5-chloro-2-methyl-4-isothiazolin-3-one, 4,5-dichloro-2-methylisothiazolin-3-one, 2-n-octylisothiazolin-3-one, Cationic compounds such as 1,2-benzisothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, 2-n-butyl-1,2-benzisothiazolin-3-one, such as N-alkyl-N, N′-dimethylbenzylammonium chloride, di-n-decyldimethylammonium chloride, benzethonium chloride, cetylpyridinium chloride, didecyldiammonium propionate, didecyldimethylammonium carbonate, chlorohexidine (hydrochloride, glucone) Acid salt, acetate salt) Bromine compounds such as hexamethylene biguanide (hydrochlor
  • the process for producing the industrial preservative composition of the present invention includes 2-methyl-4,5-trimethylene-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and / or the above-mentioned general
  • a general method is to add water to the preservative composition containing the compound represented by the formula (1) as an active ingredient and stir and mix as necessary.
  • a method of adding the industrial preservative composition thus obtained to the target general industrial water-based product is general, but depending on the target general industrial water-based product, 2-methyl-4,5-trimethylene -4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, and the compound represented by the general formula (1) can be added separately.
  • the preservative composition of the present invention is a general industrial water-based product such as emulsion, latex, water-based paint, water-based ink, paper coating agent, starch paste, pigment slurry, concrete admixture, cooling water, water treatment, water-based general household products, It is used in cosmetics, agricultural chemicals, etc., but the amount added is the active ingredient (2-methyl-4,5-trimethylene-4-isothiazolin-3-one, 2 -Methyl-4-isothiazolin-3-one, a compound represented by the general formula (1)) is preferably added so that the concentration is 0.001 wt% to 1.0 wt%, more preferably 0. Add to about 005 wt% to 0.5 wt%.
  • a known method such as a dropping method, a coating method, a spraying method, or a dipping method can be used.
  • 2-Methyl-4,5-trimethylene-4-isothiazolin-3-one can be produced by a known production method.
  • 2-Methyl-4-isothiazolin-3-one is commercially available from Chemicrea under the trade name ZONEN-MT.
  • a compound represented by the above general formula (1), for example, bis (aminopropyl) dodecylamine, is commercially available from Lonza Corporation under the trade name Lonzabac 12.
  • the preservative composition of the present invention comprises 2-methyl-4,5-trimethylene-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and / or a combination of the above general formula (1) However, it is larger than the antibacterial activity exhibited when each of these compounds is used alone, and a synergistic effect can be expected.
  • the following examples show the synergistic action of two antibacterial active substances in the preservative composition of the present invention. Moreover, the following comparative examples show the antibacterial activity of the preservative composition alone and the antibacterial activity of a combination of other isothiazoline compounds.
  • Formulation 1-6 Preparation of Formulation 1-6 (Formulation Example 1) 5 grams of 2-methyl-4,5-trimethylene-4-isothiazolin-3-one (hereinafter abbreviated as MTI) was weighed, and 93 grams of purified water was added and stirred and dissolved. Further, 2 grams of 2-methyl-4-isothiazolin-3-one (Zonen MT manufactured by Chemicrea Co., Ltd., active ingredient concentration: 50%, hereinafter abbreviated as MIT) was added and stirred, and MTI was 5.0% and MIT was 1.0%. An antiseptic composition 1 was obtained.
  • MTI 2-methyl-4,5-trimethylene-4-isothiazolin-3-one
  • Test method Dispense the bacterial solution and spore suspension adjusted to 10 6 cells / ml to a 96-well cell culture plate, add each preparation described above for evaluation to a maximum addition concentration of 3000 ppm and 2000 ppm, and pipette. And mix. After mixing, the same operation is repeated for columns 1 to 11 to mix, and column 12 is blank.
  • the minimum growth inhibitory concentration (hereinafter abbreviated as MIC) is measured by culturing 96-well cell culture plates in a 37 ° C incubator for 24 hours, yeast for 30 hours at 30 ° C, and mold for 28 hours at 28 ° C. did.
  • the MIC is measured by comparing the turbidity of the control sample and each preparation-added sample. The case where no turbidity could be confirmed was evaluated as “ ⁇ ”, and the case where turbidity could be confirmed was evaluated as “+”.
  • Example 1 The evaluation results of Formulation 1 are shown in Table 1.
  • aqueous emulsion was used as a sample for evaluation.
  • Formulations 1 to 6 described above were added to the evaluation samples so that the active ingredient concentrations were 25 ppm, 50 ppm, and 100 ppm.
  • Each sample was inoculated with 4% inoculum and stored in a 30 ° C incubator. Seven days after the inoculation, the remaining state of microorganisms was confirmed by a smear painting method. This was repeated a total of 4 times.
  • the remaining state of the microorganism was determined according to the criteria shown in Table 2 according to the amount of the microorganism remaining on the normal agar medium.
  • Table 3 shows the evaluation results of the samples to which the preservative composition 1 was added to the sample for evaluation at an active ingredient concentration of 25 ppm, 50 ppm, and 100 ppm.
  • Example 3 shows the evaluation results of the samples in which the preservative composition 2 was added to the evaluation samples at 25 ppm, 50 ppm, and 100 ppm as active ingredient concentrations.
  • Example 4 Table 3 shows the evaluation results of the samples to which the preservative composition 3 was added to the evaluation samples at 25 ppm, 50 ppm, and 100 ppm as active ingredient concentrations.
  • Table 3 shows the evaluation results of samples obtained by adding the industrial preservative composition 4 to the evaluation samples at 25 ppm, 50 ppm, and 100 ppm as active ingredient concentrations.
  • Table 3 shows the evaluation results of the samples in which the industrial preservative composition 5 was added to the evaluation samples at 25 ppm, 50 ppm, and 100 ppm as active ingredient concentrations.
  • Test method Dispense the bacterial solution and spore suspension adjusted to 10 6 cells / ml to a 96-well cell culture plate, and add each preparation described above for evaluation to a maximum additive concentration of 3000 ppm, 2000 ppm, 5000 ppm, or 4000 ppm. And mix by pipetting. After mixing, the same operation is repeated for columns 1 to 11 to mix, and column 12 is blank.
  • the minimum growth inhibitory concentration (hereinafter abbreviated as MIC) is measured by culturing 96-well cell culture plates in a 37 ° C incubator for 24 hours, yeast for 30 hours at 30 ° C, and mold for 28 hours at 28 ° C. did.
  • the MIC is measured by comparing the turbidity of the control sample and each preparation-added sample. The case where no turbidity could be confirmed was evaluated as “ ⁇ ”, and the case where turbidity could be confirmed was evaluated as “+”.
  • Tables 4 to 6 show the Psudomonas aeruginosa NBRC 12589, Candida albicans NBRC 1594, Aspergillus niger NBRC 6143 index and the NBRC 6342 index for the MTI, MIT, and Lonzabac-12 single agents and each agent combination system.
  • the FIC index (Fractional Inhibition Concentration Index) was calculated by the following equation (1).
  • FIC index Qa / QA + Qb / QB (1) (Where Qa is the MIC value of the A component when the A component and the B component are used in combination. QA is the MIC value of A component alone, Qb is the MIC value of the B component when the A component and the B component are used together. QB represents the MIC value of the B component alone)
  • the FIC index represents the effect of the combined use of the A component and the B component. When the FIC index is 1, it indicates that there is an additive action by the combined use of the A component and the B component.
  • the FIC index When the FIC index is greater than 1, it indicates that there is an antagonistic action by the combined use of the A component and the B component. When the FIC index is less than 1, it indicates that there is a synergistic effect by the combined use of the A component and the B component.
  • Table 4 shows the MIC value and FIC index for MTI, MIT single agent and each mixing ratio.
  • Example 12 Table 5 shows the MIC value and FIC index of MTI, Lonzabac 12 (adjusted to pH 6.4) alone and each mixing ratio.
  • Table 6 shows the MIC value and FIC index when a mixed product of MTI and MIT (MTI / MIT ratio 1: 1) and Lonzabacl 12 (pH adjusted to 6.4) were combined at each mixing ratio. From Table 4, Table 5, and Table 6, 2-methyl-4,5-trimethylene-4-isothiazolin-3-one (MTI) and 2-methyl-4-isothiazolin-3-one (MIT) and / or the above general
  • the preservative composition containing the compound represented by the formula (1) as an active ingredient can be expected to have a synergistic effect as compared with the preservative composition containing each single agent as an active ingredient.
  • Preservative composition 11 was added to 80.0 grams and 20.0 grams of preservative composition 12 was added and stirred to obtain a preservative composition 14 having an MTI of 4.0% and an MIT of 1.0%.
  • Preservative composition 11 was added to 50.0 grams and 50.0 grams of preservative composition 12 was added and stirred to obtain preservative composition 15 having an MTI of 2.5% and an MIT of 2.5%.
  • Preservative composition 11, preservative composition 12, and preservative composition 13 were added in the same amount and stirred, and MTI, MIT and bis (aminopropyl) dodecylamine were 1: 1: 1, and the active ingredient concentration was 5.0%. Of antiseptic composition 17 was obtained.
  • Preservative composition 19 50.0 grams of preservative composition 12 and 50.0 grams of preservative composition 13 were added and stirred to obtain preservative composition 19 having MIT 2.5% and bis (aminopropyl) dodecylamine 2.5%. It was.
  • Example 14 Preservative compositions 14, 15, 16, and 17 described above were added to the aqueous acrylic emulsion so that the active ingredient concentrations were 25 ppm, 50 ppm, and 100 ppm. Each sample was inoculated with 4% inoculum and stored in a 30 ° C incubator. Seven days after the inoculation, the remaining state of the microorganism was confirmed on a normal agar medium by a streak smearing method. This was repeated a total of 4 times.
  • the remaining state of the microorganism was determined according to the criteria shown in Table 7 according to the amount of the microorganism remaining on the normal agar medium.
  • Table 8 shows the evaluation results of the aqueous acrylic emulsion.
  • the bacterial solution was prepared in the same manner as in paragraph 0073.
  • Example 15 Preservative compositions 15, 16, 17, and 18 described above were added to the nonionic surfactant (polyoxyethylene monolaurate 1% aqueous solution) so that the active ingredient concentrations were 25 ppm, 50 ppm, and 100 ppm. Each sample was inoculated with 1% inoculum and stored in a 30 ° C incubator. Seven days after the inoculation, the remaining state of the microorganism was confirmed on a normal agar medium by a streak smearing method. This was repeated a total of 3 times.
  • the nonionic surfactant polyoxyethylene monolaurate 1% aqueous solution
  • Table 9 shows the evaluation results with a nonionic surfactant (polyoxyethylene monolaurate 1% aqueous solution).
  • a bacterial solution of paragraph 0073 was prepared and added to a lignin-based concrete admixture to cause it to decay to 10 6 CFU / ml or more.
  • Example 16 The preservative composition 15, 16, 17 described above is added to the rotten lignin-based concrete admixture so that the active ingredient concentration is 50 ppm and 100 ppm, and the image smearing method is performed 1 day, 3 days, and 7 days after the addition of the preservative. Thus, the remaining state of the microorganism was confirmed on a normal agar medium.
  • Table 10 shows the evaluation results with the lignin-based concrete admixture.
  • the preservative of the present invention includes 2-methyl-4,5-trimethylene-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one and / or a compound represented by the above general formula (1).
  • As an active ingredient rot due to microbial contamination can be significantly avoided at low concentrations.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

　L'invention concerne une composition d'agent antiseptique, qui est caractérisée en ce qu'elle contient comme ingrédients actifs 2-méthyl -4,5-triméthylène -4-isothiazolin -3-one et 2-méthyl -4-isothiazolin -3-one et/ou un composé représenté par la formule générale (1), ladite composition fournissant un agent antiseptique ayant une action antiseptique exceptionnelle et s'utilisant à faible concentration.
PCT/JP2015/050117 2014-01-15 2015-01-06 Composition d'agent antiseptique WO2015107934A1 (fr)

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CN201580004833.8A CN105916380A (zh) 2014-01-15 2015-01-06 防腐剂组合物
JP2015557789A JPWO2015107934A1 (ja) 2014-01-15 2015-01-06 防腐剤組成物

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JP2014004960 2014-01-15
JP2014-004960 2014-01-15

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017010505A1 (fr) * 2015-07-14 2017-01-19 ロンザ リミテッド Composition d'agent conservateur
CN107712438A (zh) * 2017-09-20 2018-02-23 无为县农园螃蟹养殖专业合作社 一种无毒环保型螃蟹饲料防腐剂
KR20190024968A (ko) * 2016-06-30 2019-03-08 다우 글로벌 테크놀로지스 엘엘씨 카르밤산 3-요오드-2-프로피닐-부틸 및 디아민의 상승작용적 조합

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CN107125249B (zh) * 2017-05-05 2019-11-01 奎克化学（中国）有限公司 一种复合杀菌剂以及含有它的金属切削液及其制备方法
CN107384086A (zh) * 2017-09-22 2017-11-24 苏州振振好新型建材科技有限公司 一种长效抗菌型涂料及其制备及应用方法
CN114767560B (zh) * 2022-05-20 2024-02-02 常州瑞昊环保科技有限公司 一种抗菌组合物及其应用

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JPH0769817A (ja) * 1990-04-27 1995-03-14 Zeneca Ltd 殺微生物組成物及びその使用方法
JPH1171210A (ja) * 1997-08-28 1999-03-16 Sanai Sekiyu Kk 工業用防腐剤
JP2007332111A (ja) * 2006-06-19 2007-12-27 Arch Chemicals Japan Kk 工業用防腐剤組成物
JP2009209044A (ja) * 2008-02-29 2009-09-17 Nippon Soda Co Ltd 安定な殺菌防カビ組成物
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017010505A1 (fr) * 2015-07-14 2017-01-19 ロンザ リミテッド Composition d'agent conservateur
KR20190024968A (ko) * 2016-06-30 2019-03-08 다우 글로벌 테크놀로지스 엘엘씨 카르밤산 3-요오드-2-프로피닐-부틸 및 디아민의 상승작용적 조합
JP2019527195A (ja) * 2016-06-30 2019-09-26 ダウ グローバル テクノロジーズ エルエルシー ３−ヨード−２−プロピニル−ブチルカルバメート及びジアミンの相乗的組み合わせ
KR102529483B1 (ko) 2016-06-30 2023-05-08 다우 글로벌 테크놀로지스 엘엘씨 카르밤산 3-요오드-2-프로피닐-부틸 및 디아민의 상승작용적 조합
CN107712438A (zh) * 2017-09-20 2018-02-23 无为县农园螃蟹养殖专业合作社 一种无毒环保型螃蟹饲料防腐剂

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