WO2007008484A2 - Composition microbicide - Google Patents

Composition microbicide Download PDF

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Publication number
WO2007008484A2
WO2007008484A2 PCT/US2006/025976 US2006025976W WO2007008484A2 WO 2007008484 A2 WO2007008484 A2 WO 2007008484A2 US 2006025976 W US2006025976 W US 2006025976W WO 2007008484 A2 WO2007008484 A2 WO 2007008484A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
composition
glycol
isothiazolone
glycols
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2006/025976
Other languages
English (en)
Other versions
WO2007008484A3 (fr
Inventor
Andrea Wingenfeld
Christiane Ochs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ISP Investments LLC
Original Assignee
ISP Investments LLC
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
Priority claimed from DE102005036314A external-priority patent/DE102005036314A1/de
Application filed by ISP Investments LLC filed Critical ISP Investments LLC
Priority to CN2006800327816A priority Critical patent/CN101257795B/zh
Priority to EP06774460A priority patent/EP1924140A4/fr
Priority to US11/994,854 priority patent/US8338468B2/en
Publication of WO2007008484A2 publication Critical patent/WO2007008484A2/fr
Publication of WO2007008484A3 publication Critical patent/WO2007008484A3/fr
Anticipated expiration legal-status Critical
Priority to US13/714,886 priority patent/US9288987B2/en
Ceased legal-status Critical Current

Links

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

Definitions

  • the invention relates to a microbicidal composition which comprises a mixture of at least two components, the first component being 2-methyl-3-isothiazolone (MIT) .
  • MIT 2-methyl-3-isothiazolone
  • MIT is also described by the CAS No. 2682-20-4.
  • microbicidal compositions have been disclosed, for example, by European patent 1 332 675 in which a commercially available microbicidal benzoic acid is used as second component.
  • a microbicidal composition as described at the outset and proposes that this comprises a mixture of at least two components, the first component being 2-methyl-3- isothiazolone and the second component being at least one active compound selected from the following groups of active compounds: a) compounds having activated methylol groups b) guats or polyquats c) carbamates d) organic acids e) aromatic alcohols
  • the abovementioned groups of active compounds are in each case likewise biocidal or microbicidal . They frequently have an altered antimicrobial spectrum. Precisely in combination with MIT, resultant synergistic effects are produced thereby, since a greater bandwidth of organisms can be actively combated.
  • the selection of the proposed active compounds is such that they can also be used in a wide pH range in accordance with the desired use. The invention therefore combines a broad antimicrobial activity spectrum with a wide pH application range.
  • inventive composition is usable, for example, in the pH range from 4 to 10.
  • inventive microbicidal composition is used in domestic products, for example cleaners, dishwashing agents, cleaning agents, cosmetic products, shampoos, soaps, wet wipe uses, for example using moist cloths and the like.
  • inventive composition can also be used in industrial applications, for example in coatings, paints, plasters, emulsions, dispersions, glues, latex and the like.
  • the composition is a mixture of at least two components.
  • the invention does not exclude the microbicidal composition also having more than two components, MIT then being combinable with two or more further active compounds from the said group selected compounds .
  • a plurality of active compounds of one group of active compounds are used in an inventive composition.
  • the field of application of such a microbicidal composition can thereby be further optimized and adapted for the specific application.
  • the previously described mechanisms with respect to pH and different possibilities of attacking the harmful organisms apply here in an unmodified manner.
  • composition comprises one or more different solvents.
  • a variant of the invention provides that water, glycols and/or glycol ethers are provided as solvent.
  • a further development according to the invention proposes that a synergistic action of the components present in the mixture is provided.
  • a preferred variant of the invention provides that an activity enhancement is provided by the solvent, in particular the glycols and/or glycol ethers.
  • inventive compositions are used in specific applications which contain, for example, various liquid phases.
  • an oil phase occurs in addition to a water phase.
  • the harmful organisms to be attacked are situated in the water phase or the boundary layer.
  • the use of the proposed solvents means that the active compounds also preferably remain in the aqueous phase and can destroy microorganisms there. Improved activities of the active compounds used finally result from improved active compound uptakes into the respective organisms with the proposed solvents.
  • the concentration of the active compounds used can be restricted, which decreases costs.
  • bronopol, diazolidinylurea or imidazolidinylurea are provided as compounds having activated methylol groups .
  • a further development of the invention proposes that polyaminopropyl biguanide, cetrimonium bromide or benzalconium chloride are provided as quats or polyquats .
  • a preferred variant of the invention provides that iodopropynyl butylcarbamate or dithiocarbamate are provided as carbamates .
  • An inventive variant provides that dehydroacetic acid, undecylenic acid or salicylic acid are provided as organic acids .
  • a further development of the invention proposes that phenoxyethanol , phenylethanol, phenoxypropanol , phenylpropanol or dichlorobenzyl alcohol are provided as aromatic alcohols .
  • a preferred variant of the invention provides that polypropylene glycol 2-methyl ether, 1, 2-octanediol, propylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, dipropylene glycol r ⁇ onomethyl ether, oligo- or polyethylene glycols or polypropylene glycols are provided as glycols or glycol ethers .
  • Polypropylene glycol is also called PPG-2-methyl ether.
  • weight ratio between 2-methyl-3-isothiazolone and the other components is between 1:1000 and 200:1, preferably between 2:100 and 5:1.
  • the weight ratio between the components and the solvent is between 1:100 and 100:1, preferably 1:10 to 3:2.
  • a preferred variant of the invention provides the weight percentage of glycol or glycol ether of the composition is from 0% to 85%.
  • An inventive variant provides that the weight percentage of 1, 2-octanediol of the composition is from 0% to 10%.
  • a further development of the invention proposes that the weight percentage of 2-methyl-3-isothiazolone in the composition is from 0.1% to 20%, preferably approximately 2% to 8%.
  • a preferred variant of the invention provides that the weight percentage of aromatic alcohols of the total composition is from 0% to 99.9%, preferably 0.1% to 80%.
  • An inventive variant provides that the weight percentage of water of the total composition is from 0% to 99.9%.
  • composition is essentially free from halogenated isothiazolone.
  • microbicidal compositions of the present invention are essentially free from halogenated isothiazolones .
  • "Essentially” free is taken to mean that the composition has from 0 to at most 3%, preferably from 0 to 1%, and further preferably from 0 to only 0.5%, halogenated isothiazolones (based on the weight) , based on the combined weight of halogenated isothiazolone and MIT.
  • a further concentration of halogenated isothiazolone is unstable and requires additional stabilization components. These can be, for example, metal salts and the like which, however, cause additional costs and also can lead to undesirable side effects in subsequent formulation. It is therefore expedient, based on the MIT, to provide a weight percentage as low as possible, as described, of halogenated isothiazolone.
  • the finished use formulation is sought to have at maximum a halogenated isothiazolone content of 1000 ppm.
  • the reported weight percentages relate to the total weight of the composition.
  • the table above gives an overview of the inventive compositions which exhibit the desired properties.
  • the table is to be taken to mean that the compositions having the reported weight percentages (in the 3rd column) lead to a stable composition.
  • the weight percentages are to be taken to mean preferred embodiment of the invention and likewise do not restrict the more broadly worded bandwidth of the weight percentages belonging to the invention.
  • Synergy tests were conducted using microbiological tandard methods. Ringer's Solution (Merck, VWR) was used for testing bacteria, yeast and mould species. In jars 100 ml aliguots of sterile Ringer Solution are dosed with the preservatives and a known inoculum of the single test species is added. A control sample containing no preservative is also used to ascertain the biocide effect on the inoculum. The prepared jars were incubated at 30 0 C.
  • TSA tryptic soy agar
  • MEA malt extract agar
  • the synergy of the combinations of the present invention was determined against four bacteria, Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, AND Staphylococcus aureus, a yeast, Candida albicans and two moulds Trichoderma viride and Aspergillus niger.
  • the single micro-organisms were used at a concentration of about 10 5 microbes per ml. these micro-organisms are standard reference organisms and representative of natural contaminants in many consumer and industrial applications.
  • test results for demonstration of synergy of the preservative combinations of the present invention are shown below.
  • first component (A) was MIT and the second component was phenylethylalcohol (B) .
  • B phenylethylalcohol
  • Aeruginosa Test 2.1 25 12.5 125 2500 0.55
  • Escherichia Test 1 50 25 250 2000 0.63
  • Proteus Test 1 50 25 250 2000 0.63 mirabilis Test 2.1 25 12.5 125 2000 0.56
  • Staphylococcus Test 1 75 25 250 2000 0.46 aureus Test 2.1 50 25 250 1500 0.67
  • Candida Test 1 50 25 250 2000 0.63 albicans Test 2.1 50 25 250 2500 0.60
  • Trichoderma Test 1 75 25 250 2000 0.46 viride Test 2.1 50 25 250 3000 0.58
  • QB concentration of compound B (second component in ppm, acting alone, which produced an end point (MIC of Compound B)
  • Test one was done as single test, Test 2 was performed under statistical conditions with 3 parallel samples

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (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 microbicide comprenant un mélange d'au moins deux constituants, le premier constituant étant une 2-méthyl-3-isothiazolone (MIT) et le second constituant étant au moins un composé actif choisi dans les groupes suivants de composés actifs: (a) composé renfermant des groupes méthylol activés, (b) quats ou polyquats, (c) carbamates, (d) acides organiques, et (e) alcools aromatiques.
PCT/US2006/025976 2005-07-08 2006-06-30 Composition microbicide Ceased WO2007008484A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN2006800327816A CN101257795B (zh) 2005-07-08 2006-06-30 杀微生物组合物
EP06774460A EP1924140A4 (fr) 2005-07-08 2006-06-30 Composition microbicide
US11/994,854 US8338468B2 (en) 2005-07-08 2006-06-30 Microbicidal composition
US13/714,886 US9288987B2 (en) 2005-07-29 2012-12-14 Microbicidal composition

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US69768105P 2005-07-08 2005-07-08
US60/697,681 2005-07-08
DE102005036314A DE102005036314A1 (de) 2005-07-29 2005-07-29 Mikrobizide Zusammensetzung
DE102005036314.8 2005-07-29

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US11/994,854 A-371-Of-International US8338468B2 (en) 2005-07-08 2006-06-30 Microbicidal composition
US13/714,886 Continuation US9288987B2 (en) 2005-07-29 2012-12-14 Microbicidal composition

Publications (2)

Publication Number Publication Date
WO2007008484A2 true WO2007008484A2 (fr) 2007-01-18
WO2007008484A3 WO2007008484A3 (fr) 2007-04-26

Family

ID=37637702

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/025976 Ceased WO2007008484A2 (fr) 2005-07-08 2006-06-30 Composition microbicide

Country Status (3)

Country Link
EP (1) EP1924140A4 (fr)
CN (1) CN101257795B (fr)
WO (1) WO2007008484A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2640798A4 (fr) * 2010-11-19 2014-04-30 Isp Investments Inc Composition de conservation stable et aqueuse concentrée d'acide déshydroacétique (dha) et de méthylisothiazolinone (mit)
WO2016154511A1 (fr) 2015-03-26 2016-09-29 Isp Investments Inc. Compositions synergiques d'acide déshydroacétique et procédés pour réduire le jaunissement dans diverses compositions d'utilisateur final
EP3346838B1 (fr) 2015-09-09 2020-06-24 THOR GmbH Composition biocide stable au stockage
EP3288380B1 (fr) 2015-04-09 2021-11-24 ISP Investments LLC Compositions de conservateurs synergiques

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120046167A1 (en) * 2009-04-27 2012-02-23 Basf Se Composition containing pesticide, preservative agent and unbranched 1,2-alkanodiol
JP5210360B2 (ja) * 2009-07-30 2013-06-12 ローム アンド ハース カンパニー 相乗的殺微生物組成物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4732905A (en) * 1987-03-13 1988-03-22 Betz Laboratories, Inc. Biocidal compositions and use thereof containing a synergistic mixture of 2-bromo-2-nitropropane-1,3-diol and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one
EP0900525A1 (fr) * 1997-08-20 1999-03-10 Thor Chemie Gmbh Composition biocide synergique
JP4245097B2 (ja) * 1999-05-10 2009-03-25 ソマール株式会社 有害微生物撲滅剤
JP2001048720A (ja) * 1999-08-06 2001-02-20 Asahi Denka Kogyo Kk 化粧料用保湿静菌剤
DE10042894A1 (de) * 2000-08-31 2002-03-14 Thor Chemie Gmbh Synergistische Biozidzusammensetzung mit 2-Methylisothiazolin-3-on
DE10112367A1 (de) * 2001-03-15 2002-09-26 Bayer Ag Mikrobizide Mischungen
EP1332675B2 (fr) * 2002-01-31 2012-11-07 Rohm And Haas Company Association microbicide synergique
JP4226826B2 (ja) * 2002-02-18 2009-02-18 日本エンバイロケミカルズ株式会社 工業用殺菌組成物
DE10318526A1 (de) * 2003-04-24 2004-11-11 Beiersdorf Ag Reinigungsemulsion mit hohem Fettgehalt

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP1924140A4 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2640798A4 (fr) * 2010-11-19 2014-04-30 Isp Investments Inc Composition de conservation stable et aqueuse concentrée d'acide déshydroacétique (dha) et de méthylisothiazolinone (mit)
WO2016154511A1 (fr) 2015-03-26 2016-09-29 Isp Investments Inc. Compositions synergiques d'acide déshydroacétique et procédés pour réduire le jaunissement dans diverses compositions d'utilisateur final
EP3273937A4 (fr) * 2015-03-26 2018-08-08 ISP Investments LLC Compositions synergiques d'acide déshydroacétique et procédés pour réduire le jaunissement dans diverses compositions d'utilisateur final
EP3288380B1 (fr) 2015-04-09 2021-11-24 ISP Investments LLC Compositions de conservateurs synergiques
EP3346838B1 (fr) 2015-09-09 2020-06-24 THOR GmbH Composition biocide stable au stockage

Also Published As

Publication number Publication date
WO2007008484A3 (fr) 2007-04-26
EP1924140A4 (fr) 2012-06-06
EP1924140A2 (fr) 2008-05-28
CN101257795B (zh) 2012-06-06
CN101257795A (zh) 2008-09-03

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