US20030012685A1 - Microbicidal agents - Google Patents

Microbicidal agents Download PDF

Info

Publication number
US20030012685A1
US20030012685A1 US10/204,821 US20482102A US2003012685A1 US 20030012685 A1 US20030012685 A1 US 20030012685A1 US 20482102 A US20482102 A US 20482102A US 2003012685 A1 US2003012685 A1 US 2003012685A1
Authority
US
United States
Prior art keywords
opp
active compound
mit
active
phenylphenol
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.)
Abandoned
Application number
US10/204,821
Inventor
Peter Wachtler
Martin Kugler
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.)
Lanxess Deutschland GmbH
Original Assignee
Individual
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7632145&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20030012685(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Individual filed Critical Individual
Assigned to BAYER AKTIENGESELLSCHAFT reassignment BAYER AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KUGLER, MARTIN, WACHTLER, PETER
Publication of US20030012685A1 publication Critical patent/US20030012685A1/en
Assigned to LANXESS DEUTSCHLAND GMBH reassignment LANXESS DEUTSCHLAND GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER AG
Priority to US12/469,344 priority Critical patent/US20100093815A1/en
Priority to US13/037,444 priority patent/US8246942B2/en
Abandoned 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system

Definitions

  • the present invention provides microbicidal compositions having improved bactericidal activity.
  • the invention relates to synergistic mixtures of o-phenylphenol (OPP) with other microbicidally active compounds, such as, for example, bronopol (2-bromo-2-nitro-1,3-propanediol), MIT (2-methyl-2H-isothiazol-3-one), Tektamer 38 (1 ,2-dibromo-2,4-dicyanobutane).
  • OPP o-phenylphenol
  • OPP o-Phenylphenol
  • active compound mixtures of OPP and at least one further bactericide have an unexpectedly high, synergistically enhanced activity.
  • the amounts of active compound to be employed for protecting industrial products can be reduced, resulting in more economical use or in a contribution to increased preservation quality.
  • the mixtures according to the invention are an improvement compared to the prior art, i.e. the use of the individual active compounds.
  • the novel active compound mixtures are preferably used to preserve functional liquids and water-containing industrial products susceptible to attack by microorganisms.
  • the active compound mixtures according to the invention can be used, for example, for protecting the following industrial products:
  • starch solutions, dispersions or slurries or other starch-based products such as, for example, thickeners used in printing
  • slurries of other raw materials such as color pigments (for example, iron oxide pigments, carbon black pigments, titanium dioxide pigments) or slurries of fillers such as kaolin or calcium carbonate
  • concrete additives for example those based on molasses or ligninosulfonates
  • bitumen emulsions [0009] bitumen emulsions
  • mineral oils or mineral oil products such as, for example diesel fuels
  • auxiliaries for the leather, textile or photochemical industry are auxiliaries for the leather, textile or photochemical industry.
  • Tektamer 38 (1,2-dibromo-2,4-dicyanobutane).
  • the mixing ratio of o-phenylphenol (OPP) to the other bactericidally active component can be varied within a wide range, the optimum depending, for example, on the bactericidal mixing partner used, but also on the application in question.
  • the weight ratio of o-phenylphenol (OPP) to the mixing partner should be from 99.9:0.1 to 50:50, preferably from 99:1 to 70:30, particularly preferably from 80:20 to 60:40.
  • the active compound combinations according to the invention are highly active against microorganisms.
  • the active compound combinations according to the invention are used in the protection of materials for protecting industrial materials, in particular for protecting aqueous functional liquids; they act against bacteria and molds, and also against yeast and slime organisms.
  • the following microorganisms may be mentioned by way of example, without imposing any limitations:
  • Alternaria such as Alternana tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Fusarium, such as Fusarium solani, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum;
  • Alcaligenes such as Alcaligenes faecalis, Bacillus, such as Bacillus subtilis, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aueruginosa or Pseudomonas fluorescens, Staphylococcus, such as Staphylococcus aureus;
  • Candida such as Candida albicans, Geotrichum, such as Geotrichum candidum;
  • the active compound combinations according to the invention can be added either separately, in the form of the individual active compounds, where it is possible, depending on the present preservation problem, to adjust the concentration ratio individually, or they can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols or microencapsulations in polymeric substances.
  • formulations are prepared in a manner known per se, for example by mixing the active compounds with extenders, i.e. liquid solvents, liquefied gases under pressure and/or solid carriers, if appropriate with the use of surfactants, i.e. emulsifiers and/or dispersants and/or foam formers.
  • extenders i.e. liquid solvents, liquefied gases under pressure and/or solid carriers, if appropriate with the use of surfactants, i.e. emulsifiers and/or dispersants and/or foam formers.
  • surfactants i.e. emulsifiers and/or dispersants and/or foam formers.
  • the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents.
  • suitable liquid solvents include: aromatic compounds, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol or ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and also water; liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons and also butane, propane, nitrogen and carbon dioxide; suitable solid carriers are: for example aero
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other possible additives are mineral and vegetable oils.
  • microbicidal compositions or concentrates used for protecting the industrial materials comprise the active compound combination in a concentration of from 0.1 to 95% by weight, and in particular from 5 to 50% by weight.
  • the use concentrations of the active compound combinations to be used according to the invention depend on the nature and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
  • the optimum amount for use can be determined by test series.
  • the use concentrations are in the range from 0.01 to 5% by weight, preferably from 0.05 to 2.0% by weight, based on the material to be protected.
  • the active compound combinations according to the invention show synergistic effects, i.e. the activity of the mixture is greater than the activity of the individual components.
  • Q a the amount of component A in the active compound mixture which achieves the desired effect, i.e. no microbial growth.
  • Q A the amount of component A which, when used on its own, suppresses the growth of the microorganisms.
  • Q b the amount of component B in the active compound mixture which suppresses the growth of the microorganisms.
  • Q b the amount of component B which, when used on its own, suppresses the growth of the microorganisms.
  • a synergistic index of ⁇ 1 indicates a synergistic effect for the active compound mixture.

Abstract

The invention relates to synergistic mixtures of o-phenylphenol and additional bactericides.

Description

  • The present invention provides microbicidal compositions having improved bactericidal activity. The invention relates to synergistic mixtures of o-phenylphenol (OPP) with other microbicidally active compounds, such as, for example, bronopol (2-bromo-2-nitro-1,3-propanediol), MIT (2-methyl-2H-isothiazol-3-one), Tektamer 38 (1 ,2-dibromo-2,4-dicyanobutane). [0001]
  • o-Phenylphenol (OPP) is a known active compound. It is used for industrial preservation and disinfection. The activity spectrum of OPP includes both gram-positive and gram-negative bacteria, and also fungi and yeasts. In spite of this overall good microbiological activity spectrum, the use concentration required in practice for controlling certain types of microorganisms (for example bacteria from the family of the Pseudomonadaceae) is not always entirely satisfactory from an economical and ecological point of view. There is therefore a need for broadly active microbicidal compositions which have a more even action against the microorganisms to be controlled and which can additionally be incorporated without any problems into a large number of substrates to be protected. [0002]
  • Surprisingly, it has now been found that active compound mixtures of OPP and at least one further bactericide, in particular in specific mixing ratios, have an unexpectedly high, synergistically enhanced activity. As a consequence, the amounts of active compound to be employed for protecting industrial products can be reduced, resulting in more economical use or in a contribution to increased preservation quality. In principle, it can be stated that the mixtures according to the invention are an improvement compared to the prior art, i.e. the use of the individual active compounds. The novel active compound mixtures are preferably used to preserve functional liquids and water-containing industrial products susceptible to attack by microorganisms. [0003]
  • The active compound mixtures according to the invention can be used, for example, for protecting the following industrial products: [0004]
  • starch solutions, dispersions or slurries or other starch-based products, such as, for example, thickeners used in printing [0005]
  • slurries of other raw materials such as color pigments (for example, iron oxide pigments, carbon black pigments, titanium dioxide pigments) or slurries of fillers such as kaolin or calcium carbonate [0006]
  • concrete additives, for example those based on molasses or ligninosulfonates [0007]
  • glues and adhesives based on the known raw materials of animal, vegetable or synthetic origin [0008]
  • bitumen emulsions [0009]
  • detergents and cleaners for industrial and domestic use [0010]
  • mineral oils or mineral oil products (such as, for example diesel fuels) [0011]
  • auxiliaries for the leather, textile or photochemical industry [0012]
  • precursors and intermediates of the chemical industry, for example in the production and storage of dyestuffs [0013]
  • solvent borne or water borne inks [0014]
  • wax and clay emulsions [0015]
  • Bacterial mixing partners for OPP that may be mentioned are the compounds [0016]
  • bronopol (2-bromo-2-nitro-1,3-propanediol) [0017]
  • MIT (2-methyl-2H-isothiazol-3-one) [0018]
  • Tektamer 38 (1,2-dibromo-2,4-dicyanobutane). [0019]
  • The mixing ratio of o-phenylphenol (OPP) to the other bactericidally active component can be varied within a wide range, the optimum depending, for example, on the bactericidal mixing partner used, but also on the application in question. [0020]
  • In preservatives having broad antimicrobial action used for protecting functional liquids and water-containing industrial products, the weight ratio of o-phenylphenol (OPP) to the mixing partner should be from 99.9:0.1 to 50:50, preferably from 99:1 to 70:30, particularly preferably from 80:20 to 60:40. [0021]
  • The active compound combinations according to the invention are highly active against microorganisms. The active compound combinations according to the invention are used in the protection of materials for protecting industrial materials, in particular for protecting aqueous functional liquids; they act against bacteria and molds, and also against yeast and slime organisms. The following microorganisms may be mentioned by way of example, without imposing any limitations: [0022]
  • Alternaria, such as [0023] Alternana tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Fusarium, such as Fusarium solani, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum;
  • Alcaligenes, such as [0024] Alcaligenes faecalis, Bacillus, such as Bacillus subtilis, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aueruginosa or Pseudomonas fluorescens, Staphylococcus, such as Staphylococcus aureus;
  • Candida, such as [0025] Candida albicans, Geotrichum, such as Geotrichum candidum;
  • Depending on their respective physical and/or chemical properties, the active compound combinations according to the invention can be added either separately, in the form of the individual active compounds, where it is possible, depending on the present preservation problem, to adjust the concentration ratio individually, or they can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols or microencapsulations in polymeric substances. [0026]
  • These formulations are prepared in a manner known per se, for example by mixing the active compounds with extenders, i.e. liquid solvents, liquefied gases under pressure and/or solid carriers, if appropriate with the use of surfactants, i.e. emulsifiers and/or dispersants and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents include: aromatic compounds, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol or ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and also water; liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons and also butane, propane, nitrogen and carbon dioxide; suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, aluminum oxide and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol esters, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, and also protein hydrolyzates; suitable dispersants are: for example lignosulfide waste liquors and methyl cellulose. [0027]
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils. [0028]
  • The microbicidal compositions or concentrates used for protecting the industrial materials comprise the active compound combination in a concentration of from 0.1 to 95% by weight, and in particular from 5 to 50% by weight. [0029]
  • The use concentrations of the active compound combinations to be used according to the invention depend on the nature and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimum amount for use can be determined by test series. In general, the use concentrations are in the range from 0.01 to 5% by weight, preferably from 0.05 to 2.0% by weight, based on the material to be protected. [0030]
  • The active compound combinations according to the invention show synergistic effects, i.e. the activity of the mixture is greater than the activity of the individual components. [0031]
  • The observed synergism of the active compound mixtures, claimed in the present application, consisting of o-phenylphenol (OPP) and other bactericides can be determined by the following mathematical equation (see F. C. Kull, P. C. Elisman, H. D. Sylwestrowicz and P. K. Mayer, Appl. Microbiol. 9, 538 (1961)): [0032] synergistic   index ( SI ) = Q a Q A + Q b Q B
    Figure US20030012685A1-20030116-M00001
  • where [0033]
  • Q[0034] a=the amount of component A in the active compound mixture which achieves the desired effect, i.e. no microbial growth.
  • Q[0035] A=the amount of component A which, when used on its own, suppresses the growth of the microorganisms.
  • Q[0036] b=the amount of component B in the active compound mixture which suppresses the growth of the microorganisms.
  • Q[0037] b=the amount of component B which, when used on its own, suppresses the growth of the microorganisms.
  • A synergistic index of <1 indicates a synergistic effect for the active compound mixture. [0038]
  • The synergistically enhanced activity is documented by way of example, without imposing any limitation, by the examples below. [0039]
    • EXAMPLE 1
  • Mixture OPP/BNPD (Bronopol) [0040]
  • Determination of the minimum inhibitory concentration (MIC) of compositions according to the invention against Pseudomonas fluerescens [0041]
    Active compound or active
    compound mixture MIC value against Pseudomonas
    (weight ratios) fluorescens [in mg/l] SI
    OPP 100% active compound 500
    BNPD 100% active compound 35
    OPP/BNPD (9:1) 200 0.93
    OPP/BNPD (4:1) 100 0.73
    OPP/BNPD (2.3:1) 50 0.49
    OPP/BNPD (1.5:1) 50 0.63
  • The mixtures according to the invention have pronounced synergistic activity. [0042]
    • EXAMPLE 2
  • Mixture OPP/Tektamer 38 (1,2-dibromo-2,4-dicyanobutane) [0043]
  • Determination of the minimum inhibitory concentration (MIC) of compositions according to the invention against Pseudomonas fluerescens [0044]
    Active compound or active MIC value against
    compound mixture Pseudomonas
    (weight ratios) fluorescens [in mg/l] SI
    OPP (100% active compound) 500
    Tektamer 38 (100% active 100
    compound)
    OPP/T. 38 (9:1) 200 0.56
    OPP/T. 38 (4:1) 100 0.36
    OPP/T. 38 (2.3:1) 100 0.44
    OPP/T. 38 (1.5:1)  50 0.26
  • The combinations according to the invention have pronounced synergistic activity. [0045]
    • EXAMPLE 3
  • Mixture OPP/MIT (2-methyl-2H-isothiazolin-3-one) [0046]
  • Determination of the minimum inhibitory concentration (MIC) of compositions according to the invention against Pseudomonas fluerescens [0047]
    Active compound or active MIC value against
    compound mixture Pseudomonas
    (weight ratios) fluorescens [in mg/l] SI
    OPP (100% active compound) 500
    MIT (100% active compound) 30
    OPP/MIT (9:1) 100 0.51
    OPP/MIT (4:1) 50 0.41
    OPP/MIT (2.3:1) 35 0.38
    OPP/MIT (1.5:1) 20 0.29
  • The combinations according to the invention have pronounced synergistic activity. [0048]

Claims (4)

1. A microbicidal composition comprising o-phenylphenol and at least one further compound from the group consisting of
bronopol (2-bromo-2-nitro-1,3-propanediol)
MIT (2-methyl-2H-isothiazol-3-one) and
Tektamer 38 (1,2-dibromo-2,4-dicyanobutane).
2. The use of a composition as claimed in claim 1 for protecting industrial materials against attack by fungi and algae.
3. A method for protecting industrial materials against attack by fungi and algae, characterized in that the industrial materials are admixed or treated with a composition as claimed in claim 1.
4. A process for preparing a composition as claimed in claim 1, characterized in that o-phenylphenol and at least one further compound from the group consisting of bronopol (2-bromo-2-nitro-1,3-propanediol), MIT (2-methyl-2H-isothiazol-3-one) and Tektamer 38 (1,2-dibromo-2,4-dicyanobutane) and, if appropriate, extenders-and, if-appropriate, surfactants are mixed.
US10/204,821 2000-02-24 2001-02-12 Microbicidal agents Abandoned US20030012685A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US12/469,344 US20100093815A1 (en) 2000-02-24 2009-05-20 Microbicidal compositions
US13/037,444 US8246942B2 (en) 2000-02-24 2011-03-01 Microbicidal compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10008507.5 2000-02-24
DE10008507A DE10008507A1 (en) 2000-02-24 2000-02-24 Microbicidal agent containing o-phenylphenol and bronopol, MIT and/or tektamer 38, is useful for control of fungi and algae on industrial materials

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/469,344 Continuation US20100093815A1 (en) 2000-02-24 2009-05-20 Microbicidal compositions

Publications (1)

Publication Number Publication Date
US20030012685A1 true US20030012685A1 (en) 2003-01-16

Family

ID=7632145

Family Applications (3)

Application Number Title Priority Date Filing Date
US10/204,821 Abandoned US20030012685A1 (en) 2000-02-24 2001-02-12 Microbicidal agents
US12/469,344 Abandoned US20100093815A1 (en) 2000-02-24 2009-05-20 Microbicidal compositions
US13/037,444 Expired - Lifetime US8246942B2 (en) 2000-02-24 2011-03-01 Microbicidal compositions

Family Applications After (2)

Application Number Title Priority Date Filing Date
US12/469,344 Abandoned US20100093815A1 (en) 2000-02-24 2009-05-20 Microbicidal compositions
US13/037,444 Expired - Lifetime US8246942B2 (en) 2000-02-24 2011-03-01 Microbicidal compositions

Country Status (12)

Country Link
US (3) US20030012685A1 (en)
EP (3) EP1502505B1 (en)
JP (2) JP2003523367A (en)
AT (3) ATE293884T1 (en)
AU (1) AU2001240613A1 (en)
BR (2) BR122012016624B1 (en)
DE (3) DE10008507A1 (en)
DK (1) DK1259110T3 (en)
ES (3) ES2384169T3 (en)
NO (2) NO330035B1 (en)
PT (1) PT1259110E (en)
WO (1) WO2001062081A2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080234387A1 (en) * 2005-10-13 2008-09-25 Lanxess Deutschland Gmbh Active Substance Mixtures Comprising Opp and Amines, Microbicidal Agents
US20090120327A1 (en) * 2005-01-26 2009-05-14 Matthias Buri Method for Controlling Microbial Contamination, Mineral Suspensions Obtained and Uses Thereof
CN103518716A (en) * 2009-09-25 2014-01-22 陶氏环球技术有限公司 Synergistic antimicrobial composition

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10042894A1 (en) * 2000-08-31 2002-03-14 Thor Chemie Gmbh Synergistic biocide composition with 2-methylisothiazolin-3-one
EP1523887B1 (en) * 2002-01-31 2013-02-27 Rohm and Haas Company Synergistic microbicidal combination
US9510597B2 (en) * 2012-05-24 2016-12-06 Dow Global Technologies Llc Microbicidal composition
EP3302055A1 (en) * 2015-05-31 2018-04-11 Dow Global Technologies Llc Microbicidal composition containing ortophenylphenol and isothiazolinone

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3592893A (en) * 1967-04-26 1971-07-13 Henkel & Cie Gmbh Nitro alcohols in synergistic antimicrobic compositions
US3833731A (en) * 1970-12-28 1974-09-03 Merck & Co Inc Dihalomethylglutaronitriles used as antibacterial and antifungal agents
US4800196A (en) * 1985-08-06 1989-01-24 Earth Chemical Co., Ltd. Phenyl salicylate and benzyl salicylate as acaricidal agents
US5464851A (en) * 1990-04-27 1995-11-07 Zeneca Limited Biocide composition and use
US5622546A (en) * 1993-08-20 1997-04-22 Bayer Aktiengesellschaft Mould-resistant emulsion paints
US5681852A (en) * 1993-11-12 1997-10-28 The Procter & Gamble Company Desquamation compositions
US5767137A (en) * 1994-02-08 1998-06-16 Bayer Aktiengesellschaft 1,3,2-benzodithiazol-1-oxides as microbiocides
US6217642B1 (en) * 1995-09-20 2001-04-17 Bayer Aktiengesellschaft Benzothiophene-2-carboxamide s,s-dioxides for use in anti-fouling applications
US6291549B1 (en) * 1996-10-24 2001-09-18 Bayer Aktiengesellschaft Antifouling paints

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3829305A (en) * 1971-07-06 1974-08-13 Betz Laboratories Slime control compositions containing phenolic compounds and their use
GB1505069A (en) * 1974-06-07 1978-03-22 Exxon Research Engineering Co Oil-in-water emulsions with bacteriaresistance
US4939266A (en) 1982-06-01 1990-07-03 Rohm And Haas Company Nitrosamine-free 3-isothiazolone
CA1189514A (en) * 1982-06-01 1985-06-25 Horst O. Bayer Nitrosamine-free 3-isothiazolones and process
GB8334422D0 (en) * 1983-12-23 1984-02-01 Sterwin Ag Composition
JPH03130758A (en) * 1989-10-16 1991-06-04 Fuji Photo Film Co Ltd Silver halide photographic sensitive material
ATE106183T1 (en) * 1990-04-27 1994-06-15 Zeneca Ltd BIOCIDAL COMPOSITION AND ITS USE.
JPH0683720B2 (en) * 1990-06-19 1994-10-26 日本曹達株式会社 Circulating toilet treatment agent
IT1247918B (en) * 1991-05-10 1995-01-05 Germo Spa MULTI-PURPOSE DISINFECTANT COMPOSITIONS
JPH08253404A (en) * 1995-03-17 1996-10-01 Katayama Chem Works Co Ltd Antimicrobial composition for industry
US5641808A (en) 1995-09-01 1997-06-24 Calgon Corporation Synergistic antimicrobial composition of 1,2-dibromo-2,4-dicyanobutane and esters of parahydroxybenzoic acid
JP3855569B2 (en) * 1998-12-04 2006-12-13 コニカミノルタホールディングス株式会社 Inkjet ink
DE60023902T2 (en) * 1999-08-09 2006-08-10 Zelickson, Brian D., Minneapolis STRIP DISPENSER AND METHOD
US7354423B2 (en) 1999-08-09 2008-04-08 J&J Consumer Co., Inc. Skin abrasion system and method
GB2354771A (en) 1999-10-01 2001-04-04 Mcbride Ltd Robert Bactericide combinations in detergents

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3592893A (en) * 1967-04-26 1971-07-13 Henkel & Cie Gmbh Nitro alcohols in synergistic antimicrobic compositions
US3833731A (en) * 1970-12-28 1974-09-03 Merck & Co Inc Dihalomethylglutaronitriles used as antibacterial and antifungal agents
US4800196A (en) * 1985-08-06 1989-01-24 Earth Chemical Co., Ltd. Phenyl salicylate and benzyl salicylate as acaricidal agents
US5464851A (en) * 1990-04-27 1995-11-07 Zeneca Limited Biocide composition and use
US5622546A (en) * 1993-08-20 1997-04-22 Bayer Aktiengesellschaft Mould-resistant emulsion paints
US5681852A (en) * 1993-11-12 1997-10-28 The Procter & Gamble Company Desquamation compositions
US5767137A (en) * 1994-02-08 1998-06-16 Bayer Aktiengesellschaft 1,3,2-benzodithiazol-1-oxides as microbiocides
US6217642B1 (en) * 1995-09-20 2001-04-17 Bayer Aktiengesellschaft Benzothiophene-2-carboxamide s,s-dioxides for use in anti-fouling applications
US6291549B1 (en) * 1996-10-24 2001-09-18 Bayer Aktiengesellschaft Antifouling paints

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090120327A1 (en) * 2005-01-26 2009-05-14 Matthias Buri Method for Controlling Microbial Contamination, Mineral Suspensions Obtained and Uses Thereof
US8877127B2 (en) 2005-01-26 2014-11-04 Omya International Ag Process for control of microbial contamination, mineral suspensions obtained and their uses
US8889068B2 (en) * 2005-01-26 2014-11-18 Omya International Ag Method for controlling microbial contamination, mineral suspensions obtained and uses thereof
TWI465265B (en) * 2005-01-26 2014-12-21 Omya Int Ag Process for control of microbial contamination, mineral suspensions obtained and their uses
US20080234387A1 (en) * 2005-10-13 2008-09-25 Lanxess Deutschland Gmbh Active Substance Mixtures Comprising Opp and Amines, Microbicidal Agents
US9119395B2 (en) 2005-10-13 2015-09-01 Lanxess Deutschland Gmbh Active substance mixtures comprising OPP and amines, microbicidal agents
CN103518716A (en) * 2009-09-25 2014-01-22 陶氏环球技术有限公司 Synergistic antimicrobial composition
EP2687092A1 (en) * 2009-09-25 2014-01-22 Dow Global Technologies LLC Synergistic antimicrobial composition containing ortho-phenylphenol and tris(hydroxymethyl)nitromethane
CN103518716B (en) * 2009-09-25 2015-05-27 陶氏环球技术有限公司 Synergistic antimicrobial composition

Also Published As

Publication number Publication date
NO333350B1 (en) 2013-05-13
DE50106035D1 (en) 2005-06-02
ATE336894T1 (en) 2006-09-15
WO2001062081A3 (en) 2002-06-20
WO2001062081A2 (en) 2001-08-30
US20100093815A1 (en) 2010-04-15
AU2001240613A1 (en) 2001-09-03
BR122012016624B1 (en) 2015-04-14
NO330035B1 (en) 2011-02-07
EP1259110A2 (en) 2002-11-27
EP1502506A3 (en) 2005-02-16
BR0108692B1 (en) 2013-02-05
EP1502505A2 (en) 2005-02-02
US20120035228A1 (en) 2012-02-09
EP1502506A2 (en) 2005-02-02
EP1502505B1 (en) 2006-08-23
BR0108692A (en) 2002-12-10
JP2011251993A (en) 2011-12-15
DE50110837D1 (en) 2006-10-05
US8246942B2 (en) 2012-08-21
ES2240424T3 (en) 2005-10-16
DE10008507A1 (en) 2001-08-30
ATE293884T1 (en) 2005-05-15
ES2271760T3 (en) 2007-04-16
NO20023972L (en) 2002-08-21
ES2384169T3 (en) 2012-07-02
EP1502506B1 (en) 2012-05-09
ATE556590T1 (en) 2012-05-15
EP1502505A3 (en) 2005-02-16
PT1259110E (en) 2005-08-31
NO20023972D0 (en) 2002-08-21
EP1259110B1 (en) 2005-04-27
NO20110006L (en) 2002-08-21
JP2003523367A (en) 2003-08-05
DK1259110T3 (en) 2005-08-01

Similar Documents

Publication Publication Date Title
US8246942B2 (en) Microbicidal compositions
US20060111410A1 (en) Microbicide substances
EP0611522B1 (en) Synergistic microbicidal combinations
US20080009532A1 (en) Antimicrobially Finished Solid Preparations
US9119395B2 (en) Active substance mixtures comprising OPP and amines, microbicidal agents
US20020164266A1 (en) Microbicidal mixtures
US20190269129A1 (en) Composition containing 1,2-dibromo-2,4-dicyanobutane (dbdcb) and zinc pyrithione (zpt)
US20060205716A1 (en) Microbicidal agents
US20190008147A1 (en) Composition containing 1,2-dibromo-2,4-dicyanobutane (dbdcb) and at least one organic acid and/or the derivatives thereof

Legal Events

Date Code Title Description
AS Assignment

Owner name: BAYER AKTIENGESELLSCHAFT, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WACHTLER, PETER;KUGLER, MARTIN;REEL/FRAME:013374/0425;SIGNING DATES FROM 20020716 TO 20020717

AS Assignment

Owner name: LANXESS DEUTSCHLAND GMBH, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BAYER AG;REEL/FRAME:018584/0319

Effective date: 20061122

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION