WO2018235269A1 - Composition antiseptique industrielle - Google Patents

Composition antiseptique industrielle Download PDF

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Publication number
WO2018235269A1
WO2018235269A1 PCT/JP2017/023227 JP2017023227W WO2018235269A1 WO 2018235269 A1 WO2018235269 A1 WO 2018235269A1 JP 2017023227 W JP2017023227 W JP 2017023227W WO 2018235269 A1 WO2018235269 A1 WO 2018235269A1
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WO
WIPO (PCT)
Prior art keywords
preservative
water
pyrithione
hydrogen peroxide
isothiazoline
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PCT/JP2017/023227
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English (en)
Japanese (ja)
Inventor
和彦 坂田
眞由美 古川
Original Assignee
ロンザ リミテッド
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Priority to PCT/JP2017/023227 priority Critical patent/WO2018235269A1/fr
Publication of WO2018235269A1 publication Critical patent/WO2018235269A1/fr

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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
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • 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
    • 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
    • A01N59/14—Boron; Compounds thereof

Definitions

  • the present invention relates to a preservative composition for water-based industrial products containing an isothiazoline preservative and a pyrithione preservative.
  • Preservatives are added to prevent the product from deterioration or decay due to contamination with microorganisms such as fungi and reproduction.
  • Isothiazoline compounds such as 2-methyl-4-isothiazolin-3-one and pyrithione compounds such as sodium pyrithione are used as preservatives and disinfectants in a wide range of subjects including such industrial products because of their high safety (Patent Documents 1 to 8).
  • Patent Documents 9 to 12 Some bactericidal or preservative compositions comprising both an isothiazoline compound and a pyrithione compound have also been proposed.
  • Patent Document 12 discloses a metal bromate as a stabilizer for chloroisothiazolone compounds
  • Patent Document 1 discloses a chloroisothiazolone compound to iodic acid, periodic acid, or salts thereof
  • Patent Document 2 And sodium bromate, potassium bromate and the like are disclosed as stabilizers for compositions containing 1,2-benzoisothiazolin-3-one and 2-methyl-4-isothiazolin-3-one.
  • Patent Document 4 discloses 2-2 ′ dithiobis (pyridine N-oxide) as a stabilizer of isothiazolone derivative.
  • Patent Document 5 discloses a complex in which an isothiazolone compound is adsorbed on the surface of an inorganic oxide.
  • rosin amine and rosin amide are disclosed as a stabilizer of a composition containing cuprous oxide and zinc pyrithione, and in Patent Document 8, pyrithione or a salt thereof is used.
  • Dehydroacetic acid is disclosed as a discoloration inhibitor.
  • Japanese Patent Application Laid-Open No. 05-170608 Japanese Patent Application Publication No. 2005-232070 Japanese Patent Application Laid-Open No. 2008-37811 JP 2005-82596 A JP 2007-332111 A Special Table 2006-510713 JP-H08-510286 Patent No. 57854581 Japanese Patent Application Laid-Open No. 08-099909 Special Publication 2004-524263 Japanese Patent Publication No. 2004-507475 Japanese Patent Application Laid-Open No. 05-221813
  • the present inventor has intensively studied a composition for stabilizing both components in a composition containing both an isothiazoline-based preservative and a pyrithione-based preservative. It has been found that not only isothiazoline based preservatives but also pyrithione based preservatives have a stabilizing effect, leading to the present invention. That is, the present invention provides the following preservative composition.
  • a preservative composition typically for water-based industrial products, comprising at least one stabilizer.
  • the antiseptic composition of the present invention contains an isothiazoline based antiseptic and a pyrithione based antiseptic as active ingredients, and thus a synergetic effect can be expected from both the ingredients and a stabilizer capable of stabilizing both of these ingredients. As a result, the control composition can maintain its stability over a long period as a whole.
  • the preservative for industrial products of the present invention contains an isothiazoline-based preservative and a pyrithione-based preservative as active ingredients, and includes a stabilizer that stabilizes these active ingredients.
  • isothiazoline preservatives include 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT), 2-methyl-4-isothiazolin-3-one (MIT), 2-n-octyl-4 -Isothiazolin-3-one, 1,2-benzoisothiazolin-3-one, 2-methyl-4,5-trimethylene-4-isothiazolin-3-one and the like, and an alkylisothiazolone having 15 or less carbon atoms is preferable, MIT Is particularly preferred. MIT is commercially available, for example, as ZONEN MT (manufactured by "Kemiclair") or CODEC 50C (manufactured by "Romand Haas").
  • Pyrithione-based preservatives include pyrithione salts and pyrithione complexes.
  • the pyrithione salt include sodium pyrithione and the like, and it is commercially available, for example, as Sodium Omadine (manufactured by Lonza Co., Ltd.) or Tomicide S (manufactured by Mitsubishi Chemical Co., Ltd.).
  • Examples of pyrithione complexes include zinc pyrithione and pyrithione copper.
  • the preservative composition of the present invention contains a stabilizer effective for both of these two active ingredients.
  • a stabilizer includes at least one selected from hydrogen peroxide, a metal salt of hydrogen peroxide, a compound which releases hydrogen peroxide in an aqueous solution, a peroxy acid and a metal salt of peroxy acid.
  • Hydrogen peroxide and its metal salt include hydrogen peroxide, lithium peroxide (Li 2 O 2 ), sodium peroxide (Na 2 O 2 ), potassium peroxide (K 2 O 2 ), and magnesium peroxide (MgO 2) And calcium peroxide (CaO 2 ), barium peroxide (BaO 2 ), etc., and hydrogen peroxide (H 2 O 2 ) is particularly preferable from the viewpoint of storage stability and safety.
  • Compounds that release hydrogen peroxide in aqueous solution include carbonate / hydrogen peroxide adduct (eg sodium hydrogen peroxide etc), borate / hydrogen peroxide adduct (eg sodium borate / hydrogen peroxide addition) Substances), phosphate / hydrogen peroxide adducts such as tripolyphosphate / hydrogen peroxide adducts (eg Na 2 HPO 4 ⁇ H 2 O 2 etc), pyrophosphates / hydrogen peroxide adducts (eg Na 4 P 2 O 7 ⁇ 2 H 2 O 2 etc.), urea / hydrogen peroxide adducts, hydrates of these compounds, etc. may be mentioned. Among these, urea / hydrogen peroxide adduct, sodium carbonate / hydrogen peroxide adduct and sodium borate / hydrogen peroxide adduct are preferable.
  • Peroxo acids and metal salts thereof include persulfates, persulfates, percarbonates, percarbonates (eg, sodium percarbonate etc.), perborates, perborates (eg sodium perborate etc.), Peroxy acid, perphosphate (eg, sodium perphosphate etc.), hypoperchloric acid, hypoperchlorate (eg sodium hypochlorite etc.), peracetic acid, peracetate (eg sodium peracetate), Perbenzoic acid, perbenzoate salts (eg, sodium perbenzoate and the like), hydrates of these compounds, and the like can be mentioned. Among them, percarbonate, sodium percarbonate, perborate and sodium perborate are preferred.
  • a metal ion such as iron ion when present in the water-based industrial product, a pyrithione salt such as sodium pyrithione may form a complex with the metal ion and change color. . Therefore, when using for such a water-based industrial product, in order to prevent discoloration, it is preferable to contain a discoloration inhibitor.
  • a discoloration inhibitor As a discoloration inhibitor, a chelate compound, a water-soluble zinc compound, etc. can be mentioned, for example.
  • Examples of the chelate compounds include aminocarboxylic acid type chelate compounds and phosphonic acid type chelate compounds.
  • Examples of aminocarboxylic acid chelate compounds include ethylenediaminetetraacetic acid (EDTA) and salts thereof (eg, EDTANa etc.), nitrilotriacetic acid (NTA) and salts thereof (eg, NTANa etc.), diethylenetriaminepentaacetic acid (DTPA) Salts (eg, DTPANA etc.), hydroxyethyl ethylenediaminetriacetic acid (HEDTA) and its salts (eg.
  • EDTA ethylenediaminetetraacetic acid
  • NTA nitrilotriacetic acid
  • DTPA diethylenetriaminepentaacetic acid
  • HEDTA hydroxyethyl ethylenediaminetriacetic acid
  • HEDTANa etc. triethylenetetraamine hexaacetic acid (TTHA) and its salts (eg, TTHANa etc.), 1,3-diamino Propane tetraacetic acid (PDTA) and its salt (eg, PDTANa etc.), 1,3-diamino-2-hydroxypropane tetraacetic acid (DPTA-OH) and its salt (eg, DPTA-ONa etc.), glycol ether diamine tetraacetic acid (GE TA) and its salt (eg, GEDTANa etc.), hydroxyethyliminodiacetic acid (HIDA) and its salt (eg, HIDANa etc.), dihydroxyethylglycine (DHEG) and its salt (eg, DHEGNa etc.), dicarboxymethylglutamic acid (CMGA) and salts thereof (eg, CMGANa etc.), ethylenediamine-N, N′-disuccinic acid (EDDS)
  • Examples of phosphonic acid type chelate compounds include hydroxyethylidene diphosphonic acid (HEDP) and a salt thereof (eg, HEDPNa etc.), nitrilotris methylene phosphonic acid (NTMP) and a salt thereof (eg, NTMPNa etc.), 2-phosphono- 1,2,4-butanetricarboxylic acid (PBTC) and salts thereof (eg, PBTCNa etc.), ethylenediamine tetramethylene phosphonic acid (EDTMP) and salts thereof (eg EDTMMPna etc.) and the like.
  • HEDP hydroxyethylidene diphosphonic acid
  • NTMP nitrilotris methylene phosphonic acid
  • PBTC 2-phosphono- 1,2,4-butanetricarboxylic acid
  • EDTMP ethylenediamine tetramethylene phosphonic acid
  • EDTMMPna etc. ethylenediamine tet
  • the water-soluble zinc compound may have a solubility in water of at least 1% by mass at room temperature, and examples include zinc chloride, zinc acetate, zinc sulfate, zinc nitrate, zinc gluconate, zinc fluoride tetrahydrate, zinc iodide, Zinc bromide and the like can be mentioned.
  • the discoloration inhibitor preferably contains at least one selected from the above-mentioned chelate compounds and water-soluble zinc compounds, and may be a combination of two or more.
  • the pH is preferably adjusted to 7.0 to 10.0, more preferably 7.5 to 9.5, for stabilization of the above-mentioned active ingredient. It is more preferable to adjust from .0 to 9.0.
  • Conventional compositions containing only isothiazoline based preservatives and pyrithione based preservatives are stable even at pH 7.0 or less, and in particular, 2-methyl-4-isothiazolin-3-one and pyrithione salts are each alone. When it is used as an active ingredient of the above, no stabilizer is required (see Comparative Examples 4 and 5 described later).
  • compositions containing both tend to be unstable and to be susceptible to pH, and when the pH is 7.0 or less, sufficient stability may not be obtained even when a stabilizer is included (Comparative Example 3).
  • the pH may be adjusted by a general method, and an acid such as hydrochloric acid, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali earth metal hydroxide such as magnesium hydroxide or calcium hydroxide, or the like is added. And adjust.
  • the preservative of the present invention is preferably basically made water as a solvent, but may be replaced with or in addition to the organic solvent of the above active ingredient.
  • the organic solvent include alcohols such as ethanol and isopropyl alcohol, glycols such as ethylene glycol, diethylene glycol, propylene glycol and dipropylene glycol, cellosolves such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether, and diethylene glycol monomethyl Ethers, carbitols such as diethylene glycol monoethyl ether, glycerins such as glycerin and diglycerin and derivatives thereof can be mentioned. These organic solvents may be used alone or in combination of two or more.
  • the preservative of the present invention may contain additives such as surfactants, antifoaming agents, rust inhibitors, etc., depending on the water-based industrial product to be added.
  • surfactants include nonionic surfactants such as polyoxyalkylene ether, polyoxyalkylene allyl ether, polyoxyalkylene amino ether, glycerin fatty acid ester, sorbitan fatty acid ester, sodium fatty acid, alkyl sulfate, alkyl polyoxy sulfate
  • Anionic surfactants such as ethylene salts, alkyl benzene sulfonates, ⁇ -olefin sulfonates, alkyl phosphates, etc.
  • Amphoteric surfactants such as alkyl dimethyl amine oxides, alkyl carboxy betaines, alkyl sulfo betaines and amide amino acid salts These surfactants may be used alone or in combination of two or more.
  • the content of the active ingredient in the preservative composition of the present invention is usually 1% by mass to 20% by mass of the isothiazoline preservative (typically, alkylisothiazolone, preferably 2-methyl-4-isothiazolin-3-one).
  • the pyrithione-based preservative typically a pyrithione salt, preferably sodium pyrithione
  • Mass ratio of isothiazoline preservative (typically alkylisothiazolone, preferably 2-methyl-4-isothiazolin-3-one) and pyrithione preservative (typically pyrithione salt, preferably sodium pyrithione) is preferably 1: 100 to 100: 1, more preferably 1:10 to 10: 1, and particularly preferably 1: 1 to 3: 1.
  • the proportion of both active ingredients in the total composition is preferably 1% by mass to 20% by mass, and more preferably 3% by mass to 15% by mass.
  • the stabilizer used in the present invention can stabilize any of the above two active ingredients in a very small amount, and the content in the preservative is usually 0.001% by mass to 5.0% by mass, preferably Is 0.01% by mass to 2.0% by mass, more preferably 0.1% by mass to 0.5% by mass.
  • the compounding amount of the anti-discoloring agent is usually 0.5% by mass to 50% by mass, preferably 1.0% by mass to 25% by mass. Preferably, it is 3.0 to 15% by mass.
  • the method for producing the preservative of the present invention is not particularly limited, and, for example, the discoloration inhibitor is dissolved in water, and if necessary, hydrochloric acid and / or alkali metal hydroxide or alkaline earth metal hydroxide is added. Then, the pH is adjusted to 7.0 to pH 10.0, an isothiazoline preservative and a pyrithione preservative are added to an aqueous solution of a predetermined pH containing a discoloration inhibitor, and a stabilizer is further added, followed by stirring and mixing. It can be prepared by adding a surfactant, an antifoaming agent, a rust inhibitor and the like as required.
  • the preservative of the present invention is typically used by adding to water-based industrial products.
  • industrial products for example, emulsions, latex, vinyl acetate, water-based paint, water-based ink, coating agent for paper, starch paste, pigment slurry, concrete admixture, cooling water, water treatment, water-based general household products, cosmetics And pesticides.
  • the use thereof is not particularly limited, and in addition, it can be used for biological samples, plastics, leather and the like.
  • the addition amount when added to such an object, typically an industrial product varies depending on the addition object, in the case of a water-based industrial product, generally, the concentration of the active ingredient in the industrial product is 1 to 5000 ppm.
  • Example 1 After adding 13% of hydrochloric acid (reagent special grade, Wako Pure Chemical 1 mol / L, the same shall apply hereinafter) to water, add 10% of ethylenediaminetetraacetic acid tetrasodium tetrahydrate (hereinafter abbreviated as EDTA-4Na), and add 2-methyl- 3.5% of 4-isothiazolin-3-one (hereinafter abbreviated as MIT) is added and stirred, and 1.5% of sodium pyrithione (hereinafter abbreviated as Napt) is added and agitated, and then hydrogen peroxide water (reagent is added A preservative was prepared by adding 0.15% of special grade, 31% purity, and so forth). The pH of the obtained preservative was 9.0.
  • hydrochloric acid solvent special grade, Wako Pure Chemical 1 mol / L, the same shall apply hereinafter
  • MIT 2-methyl- 3.5% of 4-isothiazolin-3-one
  • Napt sodium pyrithi
  • Example 2 After adding 18% hydrochloric acid to water, add 10% EDTA-4Na, add 3.5% of MIT and stir, add 1.5% of Napt and stir, then 0.25% hydrogen peroxide solution In addition, a preservative was prepared. The pH of the obtained preservative was 8.3.
  • Example 3 18% hydrochloric acid is added to water, 10% EDTA-4Na is added, 3.5% MIT is added and stirred, and 1.5% Napt is added and stirred, then urea / hydrogen peroxide adduct ( 0.3% of a Merck reagent (hereinafter also referred to as UHPA) may be added to prepare a preservative.
  • a Merck reagent hereinafter also referred to as UHPA
  • Example 4 After 13% of hydrochloric acid was added to water, 5.0% of hydroxyethylidene diphosphonate tetrasodium (reagent manufactured by Wako Pure Chemical Industries, Ltd., hereinafter sometimes abbreviated as HEDP-4Na hereinafter) was added, and MIT was added 3. After adding 5% and stirring, and adding 1.5% of Napt and stirring, 0.3% of urea / hydrogen peroxide adduct was added to prepare a preservative. The pH of the obtained preservative was 9.4.
  • Example 5 After adding 18% of hydrochloric acid to water, add 10% of EDTA-4Na, add 3.5% of MIT and stir, add 1.5% of Napt and stir, then add sodium perborate tetrahydrate ( A preservative manufactured by Wako Pure Chemical Industries, Ltd., containing 0.3% of a reagent manufactured by Wako Pure Chemical Industries, Ltd., hereinafter, may be abbreviated as SPT hereinafter) was added. The pH of the obtained preservative was 8.3.
  • SPT sodium perborate tetrahydrate
  • Example 6 After adding 18% hydrochloric acid to water, add 10% EDTA-4Na, add 7.0% of MIT and stir, add 3.0% of Napt and stir, then 0.25% hydrogen peroxide solution In addition, a preservative was prepared. The pH of the obtained preservative was 8.3.
  • Example 7 After 19% hydrochloric acid is added to water, 10% EDTA-4Na is added, 3.5% MIT is added and stirred, 1.5% Napt is added and stirred, and 0.25% hydrogen peroxide solution is added. In addition, a preservative was prepared. The pH of the obtained preservative was 7.9.
  • Comparative Example 1 1.5% of Napt was added to water, and 3.5% of MIT was added and stirred to prepare a preservative. The pH of the obtained preservative was 8.9.
  • Residual rate (%) (Y / X) x 100 (X in the formula represents the initial concentration of MIT and Napt, and Y represents the concentration of MIT and Napt after one week, two weeks, and four weeks at 50 ° C)
  • an antiseptic composition in which these active ingredients are stable for a long period of time and the antiseptic effect can be maintained for a long time while synergy between the isothiazoline antiseptic and the pyrithione antiseptic can be expected.

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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

La présente invention concerne une composition antiseptique qui est destinée à produire un effet synergique entre un antiseptique d'isothiazoline et un antiseptique de pyrithione, et dans laquelle ces substances actives ont une stabilité à long terme permettant de maintenir un effet antiseptique à long terme. La composition antiseptique contient un agent antiseptique à base d'isothiazoline, un agent antiseptique à base de pyrithione et au moins un stabilisant choisi dans le groupe constitué du peroxyde d'hydrogène, d'un sel métallique de peroxyde d'hydrogène, d'un composé qui élue le peroxyde d'hydrogène dans une solution aqueuse, d'un peroxyacide et d'un sel métallique d'un peroxyacide.
PCT/JP2017/023227 2017-06-23 2017-06-23 Composition antiseptique industrielle WO2018235269A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5210094A (en) * 1990-02-21 1993-05-11 Rohm And Haas Company Sulphur-based stabilizers for 3-isothiazolones
JPH06502386A (ja) * 1988-05-02 1994-03-17 レスター・テクノロジーズ・コーポレーシヨン 殺微生物的物質の組み合わせおよびそれらの使用
JPH0859414A (ja) * 1994-08-19 1996-03-05 Arakawa Chem Ind Co Ltd 工業用防腐防黴剤及び工業用防腐防黴方法
JP2003238319A (ja) * 2002-01-31 2003-08-27 Rohm & Haas Co 相乗的殺微生物配合物
JP2004507475A (ja) * 2000-08-31 2004-03-11 トール　ゲーエムベーハー ２−メチルイソチアゾリン−３−オンを含む相乗殺生剤組成物
JP2004524263A (ja) * 2000-08-21 2004-08-12 トール ゲーエムベーハー 相乗作用のある殺生剤組成物
JP2006075704A (ja) * 2004-09-08 2006-03-23 Asahi Kasei Chemicals Corp 消臭剤および消臭方法
JP2008037811A (ja) * 2006-08-08 2008-02-21 Arch Chemicals Japan Kk 工業用防腐剤組成物

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06502386A (ja) * 1988-05-02 1994-03-17 レスター・テクノロジーズ・コーポレーシヨン 殺微生物的物質の組み合わせおよびそれらの使用
US5210094A (en) * 1990-02-21 1993-05-11 Rohm And Haas Company Sulphur-based stabilizers for 3-isothiazolones
JPH0859414A (ja) * 1994-08-19 1996-03-05 Arakawa Chem Ind Co Ltd 工業用防腐防黴剤及び工業用防腐防黴方法
JP2004524263A (ja) * 2000-08-21 2004-08-12 トール ゲーエムベーハー 相乗作用のある殺生剤組成物
JP2004507475A (ja) * 2000-08-31 2004-03-11 トール　ゲーエムベーハー ２−メチルイソチアゾリン−３−オンを含む相乗殺生剤組成物
JP2003238319A (ja) * 2002-01-31 2003-08-27 Rohm & Haas Co 相乗的殺微生物配合物
JP2006075704A (ja) * 2004-09-08 2006-03-23 Asahi Kasei Chemicals Corp 消臭剤および消臭方法
JP2008037811A (ja) * 2006-08-08 2008-02-21 Arch Chemicals Japan Kk 工業用防腐剤組成物

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