WO2008018386A1 - Composition préservatrice à usages industriels - Google Patents

Composition préservatrice à usages industriels Download PDF

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Publication number
WO2008018386A1
WO2008018386A1 PCT/JP2007/065274 JP2007065274W WO2008018386A1 WO 2008018386 A1 WO2008018386 A1 WO 2008018386A1 JP 2007065274 W JP2007065274 W JP 2007065274W WO 2008018386 A1 WO2008018386 A1 WO 2008018386A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen peroxide
composition
methyl
isothiazoline
preservative composition
Prior art date
Application number
PCT/JP2007/065274
Other languages
English (en)
Japanese (ja)
Inventor
Kazuhiko Sakata
Original Assignee
Arch Chemicals Japan, Inc.
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 Arch Chemicals Japan, Inc. filed Critical Arch Chemicals Japan, Inc.
Priority to KR1020097002390A priority Critical patent/KR101431288B1/ko
Publication of WO2008018386A1 publication Critical patent/WO2008018386A1/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
    • 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
    • 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

Definitions

  • the present invention relates to general industrial water-based products such as emulsion, latex, water-based paint, and water-based ink.
  • Paper coating agents, starch paste, pigments, slurries, concrete admixtures, etc. are used to prevent deterioration and rot due to microbial contamination, especially 2 methyl-4 isothiazoline 3 and 1, 2
  • the present invention relates to an industrial preservative composition having excellent long-term stability of a composition containing nzoisothiazoline 3 -one.
  • 2 Methyl 4 isothiazoline 1 3-one and 1, 2 Benzisothiazoline 1 3 on Containing composition is aqueous such as emulsion, latex, water-based paint, water-based ink, paper coating agent, starch paste, pigment slurry, concrete admixture, etc. It is an industrial preservative that is added to industrial products to prevent product deterioration and spoilage caused by microorganisms such as bacteria and fungi.
  • 2 methyl-4 isothiazoline-3one is water-soluble, it is used by dissolving in water, an alcohol, glycol or a mixed solvent thereof, and the pH of the composition is medium. It is a sex area.
  • 1,2-Benzoisothiazolin-3-one is sparingly soluble in water, so water-soluble salts of alkali metal salts and amine salts can be converted into water-soluble solvents such as water, glycols, amines, or mixed solvents thereof. It is used by dissolving, and the pH of the composition is in the alkaline region.
  • Patent Document 1 describes a composition containing 2 methyl 4 isothiazoline 1 3 -one or 1, 2 benzoisothiazoline 1 3 -one.
  • 2 Methyl-4 isothiazoline-3one and 1,2 benzoisothiazoline-3one alone are stable from acidic to alkaline and wide pH range 2 Methinole 4 Isothiazoline-3one and 1, 2 Benzisothiazoline 3 —Compositions containing ON are poorly stable in the alkaline region at pH 7 or higher, so high concentrations of 1,2 monobenzoisothiazolin-3-one dissolved in water-soluble solvents It was difficult to obtain an antiseptic composition.
  • Patent Document 2 a composition containing a metal bromate in an isothiazolone-based composition 1S
  • Patent Document 3 a composition containing 3-isothiazolone-based compound in iodic acid, periodic acid, or a metal salt thereof, etc.
  • the disclosed force S, the disclosed isothiazolone-based compositions are 5 chloro-2-methyl-4 isothiazoline-3-one and 2 methyl-4-isothiazoline-3-one.
  • Patent Document 4 discloses a method for stabilizing a composition containing 1,2-benzoisothiazolin-3-one.
  • the pH of this composition is limited to the acidic region. Nothing is said about the range of pH from neutral to alkaline.
  • Patent Document 5 discloses sodium bromate, potassium bromate and the like as stabilizers for compositions containing 1,2 benzoisothiazolin-3one and 2methyl-4isothiazolin-3one, but they are stable at 50 ° C.
  • the blending amount of sodium bromate and potassium bromate is required to be 0.1% or more. As a result, the stability at low temperature becomes insufficient. These compounds have been designated as dangerous goods by the Fire Service Act, so it was necessary to reduce their use.
  • Patent Document 1 Special Table 2001—515016
  • Patent Document 2 Japanese Patent Laid-Open No. 05-221813
  • Patent Document 3 Japanese Patent Laid-Open No. 05-170608
  • Patent Document 4 Japanese Patent Laid-Open No. 09-263504
  • Patent Document 5 Japanese Unexamined Patent Publication No. 2005-232232
  • composition containing 2-methyl-4-isothiazoline 3-one and 1,2-benzoisothiazoline 3-one has a composition in the range of 7 to 11. We found that the product can maintain stability over a long period of time.
  • the pH of a composition containing 2-methyl-4-isothiazoline-1-one and 1,2-benzisothiazoline-1-one is in the range of 7 to 11, and hydrogen peroxide, metal salt of hydrogen peroxide, penolexo acid and metal of peroxo acid. At least one selected from the group consisting of salts
  • 2 methyl-4 isothiazoline-3-one and 1,2-benzisothiazolin-3-one-containing composition can maintain stability over a long period of time.
  • the industrial preservative composition of the present invention has a pH in the range of 7 to 11 and contains 2-methyl-4-isothiazoline 3-one and 1,2-benzoisothiazoline 3-one as active ingredients, hydrogen peroxide, and peroxide.
  • hydrogen peroxide and the metal salt thereof according to the present invention include hydrogen peroxide, lithium peroxide (Li0), sodium peroxide (Na0), potassium peroxide (K0), and peroxide.
  • Li0 lithium peroxide
  • Na0 sodium peroxide
  • K0 potassium peroxide
  • MgO magnesium
  • CaO calcium peroxide
  • barium peroxide and the like can be mentioned, and hydrogen peroxide is particularly preferable from the viewpoint of storage stability and safety.
  • Peroxo acids and their metal salts are persulfuric acid, persulfate, percarbonate, percarbonate, phosphoric acid, perphosphate, hypoperchloric acid, hypoperchlorate, peracetic acid, peracetate, Although perbenzoic acid and perbenzoate are mentioned, percarbonate and sodium percarbonate are more preferable.
  • sodium hydroxide is added to the composition. It is preferable to blend an alkali metal hydroxide such as potassium hydroxide or an alkaline earth metal hydroxide such as magnesium hydroxide or calcium hydroxide.
  • organic solvents for improving the solubility of these active ingredients for example, ethanol, isopropylenoles such as isopropylenorenole, ethylene glycol, diethylene gnole, propylene glycol, dipropylene glycol Genoleol such as Nole, etc., Senolesolebu such as Ethylene Glycole Monomethinoleatenore, Ethylene Glycoleo Monoethylenoleateenore g. Diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether It is possible to use carbitols such as tellurium, glycerins such as glycerin and diglycerin and derivatives thereof. These organic solvents can be used alone or in combination of two or more.
  • surfactants such as nonionic surfactants such as polyoxyalkylene ethers, polyoxyalkylene ethers, polyoxyalkylene amino ethers, glycerin fatty acid esters, sorbitan fatty acid esters, and fatty acids.
  • anion surfactant such as alkyl phosphate, alkynol dimethylamine oxide, alkyl carboxybetaine
  • Amphoteric surfactants such as alkylsulfobetaine and amide amino acid salts, organic acids such as succinic acid, succinic acid and tartaric acid and their salts, known chelating agents, antifoaming agents, antifungal agents and other additives can do.
  • the composition of the industrial preservative composition of the present invention is as follows.
  • 2 methyl-4 isothiazoline-3-one is 0.1 to 25% by weight, more preferably 1% to 10% by weight
  • 1,2-benzoisothiazolin-3-one is 0.1% to 25% by weight, more preferably 1% to 20% by weight
  • 2 methyl-4 isothiazoline-3 It is preferred that the ratio of ON to 1,2 benzoisothiazoline-3 ON is from 1:20 to 20: 1 on a weight basis.
  • the proportion of both compounds in the composition is 5% by weight to 25% by weight. I prefer the following!
  • At least one compound selected from the group consisting of hydrogen peroxide, metal salts of hydrogen peroxide, peroxo acids and metal salts of peroxo acids is 0.001% by weight when the preservative composition for industrial use is 100% by weight.
  • the above is preferable. More preferably, it is 0.005% by weight to 0.2% by weight.
  • the organic solvent for improving the solubility of the active ingredients of 2 methyl 4 isothiazoline 1 3 on and 1,2 benzisothiazoline 1 3 on is 0.1 to 80% by weight, more preferably 5 to 70% by weight. %.
  • the method for producing the industrial preservative composition of the present invention comprises dissolving alkali metal or / and alkaline earth metal hydroxide and 1,2-benzoisothiazolin-3-one in water, Add 2% methyl-4 isothiazoline-3one after adding organic solvent according to The Furthermore, at least one compound selected from the group consisting of hydrogen peroxide, metal salt of hydrogen peroxide, peroxo acid and metal salt of peroxo acid is added and mixed with stirring. Surfactants, antifoaming agents, etc. are added as necessary.
  • the industrial preservative composition of the present invention is used for general industrial water-based products such as emulsion, latex, water-based paint, water-based ink, paper coating agent, starch paste, pigment slurry, concrete admixture and the like.
  • the amount added is preferably about 50-10 OOppm, more preferably about 10-5000ppm for the effective general industrial water-based product.
  • a method of adding for example, a known method such as a dropping method, a coating method, a spraying method, or a dipping method can be used.
  • the industrial preservative composition of the present invention has a pH in the range of 7 to 11, and contains 2-methyl-4-isothiazoline 3-one and 1,2-benzoisothiazoline 3-one as active ingredients, and hydrogen peroxide.
  • a stable antiseptic effect can be obtained for a long time even in actual use.
  • BIT 1,2 benzoisothiazoline 1-one
  • Example 2 was similarly prepared using 1%. At this time, ⁇ was 8.2.
  • Example 1 hydrogen peroxide solution 0.16% instead of 0.3% hydrogen peroxide solution 0.16%, sodium percarbonate 0.05%, dipropylene glycol 55% instead of diethylene glycol 55.1%
  • the product prepared in Example 3 was designated as Example 3. ⁇ at this time was 9.6.
  • Example:! ⁇ 4 50g of the industrial preservative composition of Comparative Examples 1-3 were collected in a glass bottle and sealed. And stored in an oven at 50 ° C. Over time, the residual concentrations of BIT and MIT were measured by high performance liquid chromatography, and the hue change of the industrial preservative composition was visually judged.
  • the residual rate was calculated by the following formula.
  • Residual rate (%) (Y / X) X 100
  • the industrial preservative composition of the present invention has a pH in the range of 7 to 11, 2-methyl-4-sothiazoline-3-one, 1,2-benzisothiazoline-3-one, hydrogen peroxide, hydrogen peroxide, Contains at least one compound selected from the group consisting of metal oxyhydroxides, peroxoacids and metal salts of peroxoacids, so that the long-term stability of the active ingredient is excellent, and the antiseptic effect as a preparation is maintained over a long period of time. it can.

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

Abstract

La présente invention concerne un composition préservatrice à usages industriels, contenant de la 2-méthyl-4-isothiazolin-3-one et de la 1,2-benzoisothiazolin-3-one, ayant une valeur de pH variant de 7 à 11, et contenant en outre un composé choisi parmi le groupe constitué de peroxyde d'hydrogène, d'un sel métallique de peroxyde d'hydrogène, d'un acide peroxo et d'un sel métallique d'acide peroxo. La composition présente une excellent stabilité à long terme.
PCT/JP2007/065274 2006-08-08 2007-08-03 Composition préservatrice à usages industriels WO2008018386A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020097002390A KR101431288B1 (ko) 2006-08-08 2007-08-03 공업용 방부제 조성물

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006215250A JP5108264B2 (ja) 2006-08-08 2006-08-08 工業用防腐剤組成物
JP2006-215250 2006-08-08

Publications (1)

Publication Number Publication Date
WO2008018386A1 true WO2008018386A1 (fr) 2008-02-14

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Application Number Title Priority Date Filing Date
PCT/JP2007/065274 WO2008018386A1 (fr) 2006-08-08 2007-08-03 Composition préservatrice à usages industriels

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JP (1) JP5108264B2 (fr)
KR (1) KR101431288B1 (fr)
WO (1) WO2008018386A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011039088A2 (fr) 2009-10-02 2011-04-07 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Concentres microbicides stables au stockage et leur utilisation en tant que conservateurs
CN103910506A (zh) * 2012-12-28 2014-07-09 辽宁奥克化学股份有限公司 一种用作混凝土外加剂的防腐剂

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013129739A (ja) * 2011-12-21 2013-07-04 Toagosei Co Ltd 水性重合体エマルション組成物の製造方法
WO2018235269A1 (fr) * 2017-06-23 2018-12-27 ロンザ リミテッド Composition antiseptique industrielle

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01224306A (ja) * 1988-03-01 1989-09-07 Osamu Umekawa 工業用殺菌組成物
JPH03188071A (ja) * 1989-11-10 1991-08-16 Thor Chem Gmbh 安定化３―イソチアゾロン水溶液
JP2000038306A (ja) * 1998-07-23 2000-02-08 Katayama Chem Works Co Ltd 工業的防腐防かび方法
JP2000327506A (ja) * 1999-04-16 2000-11-28 Rohm & Haas Co 安定な殺微生物剤組成物
JP2001515016A (ja) * 1997-08-20 2001-09-18 トール ヘミー ゲゼルシャフト ミット ベシュレンクテル ハフツング 相乗作用を有する生物致死性組成物
JP2001302418A (ja) * 2000-04-28 2001-10-31 Permachem Asia Ltd 工業用殺菌剤
JP2002518355A (ja) * 1998-06-15 2002-06-25 ナルコ ケミカル カンパニー 過酢酸および非酸化性殺虫剤を含む微生物の増殖を抑制するための方法および組成物
JP2005232070A (ja) * 2004-02-19 2005-09-02 Shinto Fine Co Ltd 工業用抗菌組成物

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01224306A (ja) * 1988-03-01 1989-09-07 Osamu Umekawa 工業用殺菌組成物
JPH03188071A (ja) * 1989-11-10 1991-08-16 Thor Chem Gmbh 安定化３―イソチアゾロン水溶液
JP2001515016A (ja) * 1997-08-20 2001-09-18 トール ヘミー ゲゼルシャフト ミット ベシュレンクテル ハフツング 相乗作用を有する生物致死性組成物
JP2002518355A (ja) * 1998-06-15 2002-06-25 ナルコ ケミカル カンパニー 過酢酸および非酸化性殺虫剤を含む微生物の増殖を抑制するための方法および組成物
JP2000038306A (ja) * 1998-07-23 2000-02-08 Katayama Chem Works Co Ltd 工業的防腐防かび方法
JP2000327506A (ja) * 1999-04-16 2000-11-28 Rohm & Haas Co 安定な殺微生物剤組成物
JP2001302418A (ja) * 2000-04-28 2001-10-31 Permachem Asia Ltd 工業用殺菌剤
JP2005232070A (ja) * 2004-02-19 2005-09-02 Shinto Fine Co Ltd 工業用抗菌組成物

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011039088A2 (fr) 2009-10-02 2011-04-07 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Concentres microbicides stables au stockage et leur utilisation en tant que conservateurs
WO2011039088A3 (fr) * 2009-10-02 2011-05-26 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Concentres microbicides stables au stockage et leur utilisation en tant que conservateurs
US8592358B2 (en) 2009-10-02 2013-11-26 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Storage-stable, synergistic microbicidal concentrates containing an isothiazolone, an amine and an oxidizing agent
CN104970043A (zh) * 2009-10-02 2015-10-14 乔治洛德方法研究和开发液化空气有限公司 贮存稳定的包含异噻唑啉酮、胺和氧化剂的协同杀微生物浓缩物
CN104970043B (zh) * 2009-10-02 2018-01-23 乔治洛德方法研究和开发液化空气有限公司 贮存稳定的包含异噻唑啉酮、胺和氧化剂的协同杀微生物浓缩物
CN103910506A (zh) * 2012-12-28 2014-07-09 辽宁奥克化学股份有限公司 一种用作混凝土外加剂的防腐剂

Also Published As

Publication number Publication date
KR101431288B1 (ko) 2014-08-20
KR20090051166A (ko) 2009-05-21
JP5108264B2 (ja) 2012-12-26
JP2008037811A (ja) 2008-02-21

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