EP0500712A1 - Lutte contre des micro-organismes mucilagineux - Google Patents

Lutte contre des micro-organismes mucilagineux

Info

Publication number
EP0500712A1
EP0500712A1 EP90917196A EP90917196A EP0500712A1 EP 0500712 A1 EP0500712 A1 EP 0500712A1 EP 90917196 A EP90917196 A EP 90917196A EP 90917196 A EP90917196 A EP 90917196A EP 0500712 A1 EP0500712 A1 EP 0500712A1
Authority
EP
European Patent Office
Prior art keywords
cysteine
ppm
liquid
weight
derivative
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.)
Withdrawn
Application number
EP90917196A
Other languages
German (de)
English (en)
Inventor
Hans-Joachim Grebe
Rudolf Dr. Lehmann
Klaus-Peter Dr. Bansemir
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 DE3938130A external-priority patent/DE3938130A1/de
Priority claimed from DE4007227A external-priority patent/DE4007227A1/de
Priority claimed from DE4028245A external-priority patent/DE4028245A1/de
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0500712A1 publication Critical patent/EP0500712A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/762—Organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/783—Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/04—Production of frozen sweets, e.g. ice-cream
    • A23G9/22—Details, component parts or accessories of apparatus insofar as not peculiar to a single one of the preceding groups
    • A23G9/30—Cleaning; Keeping clean; Sterilisation

Definitions

  • the present invention relates to the use of cysteine and / or cysteine derivatives for combating slime-forming microorganisms, a method for combating slime-forming microorganisms and a slime-fighting antimicrobial agent which contains cysteine and / or a cysteine derivative, alone or in combination with microbicides, for use in such a process.
  • bio-mucilages are to be understood as the sticky emissions of microorganisms, in particular bacteria, and the microorganisms themselves which produce these secretions, insofar as they are part of the sticky mass.
  • microorganisms to solid surfaces and the development of bio-mucilages is a process that plays a significant role both in nature and in man-made systems, for example in pipelines, water treatment systems and pipelines for cooling liquids.
  • the microorganisms which, depending on their environmental conditions, produce mucus layers enveloping the cells, which are responsible for their adhesion to surfaces of the most varied types, include both pathogenic and non-pathogenic species.
  • Such microorganisms lead to the formation of microcolonies and to the formation of biofilms, which often prove to be firmly adhering structures.
  • An essential factor for the relatively favorable growth conditions of microorganisms in the industrial sector is the high proportion of reused or in a closed system circulating fluid.
  • substances which have an anti-microbial action against freely moving bacteria and which do not influence the flow properties of the flowing medium in liquid-carrying systems can also be used to control mucus-forming bacteria.
  • the addition of chlorine, quaternary ammonium compounds, tin compounds, sulfones, thiocarbates, guanidine derivatives and thiocyanates to the liquids in industrial cooling systems has been proposed (L.E. Palmer, Che. -Anl. Verf. 1980, 78).
  • the cysteine derivatives which can be used according to the invention are in particular N- and / or S-acyl derivatives, among which N-acetyl-L-cysteine, S-acetyl-L-cysteine and N, S-diacetyl-L-cysteine and mixtures thereof are particularly preferred are preferred.
  • cysteine and / or cysteine derivatives limits the slime formation capacity of bacterial populations which usually occur in practice in such a way that the slime formation is generally noticeably reduced even at concentrations of 500 ppm of such compounds, but without the growth capacity of those without them Mucus production often hinder tolerable bacteria to the same extent.
  • cysteine and / or the cysteine derivative in particular L-cysteine, N-acetyl-L-cysteine, S-acetyl-L-cysteine and N, S-diacetyl-L-cysteine and mixtures thereof, with N-acetyl-L-cysteine being particularly preferred, a microbicidal active ingredient selected from the group comprising aldehydic active ingredients, quaternary ammonium compounds, phenolic active ingredients , Isothiazolinone and their mixtures, added to the liquid. It is observed that such microbicidal active substances are effective in significantly lower concentrations than is the case in the absence of the cysteine derivative. The mucus-fighting property of the cysteine derivative is also unexpectedly enhanced by the addition of such microbicides.
  • the process according to the invention essentially consists in adding cysteine and / or a cysteine derivative in combination with one or more of the above-mentioned microbicidal active ingredients in amounts effective for controlling abrasion to the liquid of the liquid-carrying system. It is preferably carried out in such a way that concentrations of cysteine and / or cysteine derivative in the liquid of 50 ppm to 5000 ppm and more microbicidal active ingredient from 5 ppm to 5000 ppm are present.
  • the concentrations are preferably 50 ppm to 3000 ppm, in particular 300 ppm to 1000 ppm, of aldehyde agent and 50 ppm to 2000 ppm, in particular 200 ppm to 1000 ppm, of cysteine and / or cysteine derivative.
  • the concentrations are preferably 10 ppm to 500 ppm, in particular 50 ppm to 250 ppm, of quaternary ammonium compound and 50 ppm to 1000 ppm, in particular 100 ppm to 500 ppm, of cysteine and / or cysteine derivative.
  • the concentrations are preferably 5 ppm to 3000 ppm, in particular 10 ppm to 2000 ppm, of phenolic active ingredient and 50 ppm to 1000 ppm, in particular 100 ppm to 500 ppm, of cysteine and / or cysteine derivative.
  • the concentrations are preferably from 5 ppm to 500 ppm, in particular from 10 ppm to 100 ppm, of the isothiazolinone and 25 ppm ppm to 1000, especially 50 ppm "to 250 ppm, of cysteine and / or cysteine.
  • concentrations can be increased by adding the individual components, both in substance and in particular in aqueous solution, but advantageously by using an agent according to the invention which is a combination of cysteine or cysteine derivatives, in particular L-cysteine, N-acetyl-L-cysteine, S- Acetyl-L-cysteine, NS-diacetyl-L-cysteine and mixtures thereof, with a microbicidal active ingredient, selected from the group comprising aldehydic active ingredients, quaternary ammonium compounds, phenolic active ingredients and isothiazolinones and their mixtures, are achieved the.
  • cysteine or cysteine derivatives in particular L-cysteine, N-acetyl-L-cysteine, S- Acetyl-L-cysteine, NS-diacetyl-L-cysteine and mixtures thereof, with a microbicidal active ingredient, selected from the group comprising alde
  • L-cysteine is a naturally occurring amino acid and is usually obtained from protein hydrolyzates.
  • N-Acetyl-L-cysteine can be prepared from L-cysteine or its salts by the process specified in US Pat. No. 3,091,569.
  • S-acetyl-L-cysteine for example, * according to the method described by Y. Trudelle and A. Caille in Int. J. Peptide Prot. Res. 10 (1977), 291.
  • the production of N, S-diacetyl-cysteine is described, for example, by HA Smith and G. Gorin in J. Org. Chem. 26 (1961), 828.
  • Cysteine and the cysteine derivatives can be used as such or in the form of their salts, in particular their alkali salts.
  • the amounts of cysteine or cysteine derivatives given in the context of the present invention each relate to the free compounds of this type.
  • the aldehydic active substance which can be used in the process according to the invention is preferably a compound from the group comprising the saturated aliphatic aldehydes having 1 to 6 C atoms, the saturated aliphatic dialdehydes having 2 to 6 C atoms, the aromatic dialdehydes and their mixtures.
  • Formaldehyde, acetaldehyde, propionaldehyde, glyoxal, malondialdehyde, succinedialdehyde, glutardialdehyde and phthalaldehyde, alone or in mixtures, are particularly suitable.
  • the aldehyde active ingredient may be present as such or in the form of an adduct which cleaves it under the conditions of use, for example with amines or aids.
  • Such aldehydic active substances are contained in the agents according to the invention preferably in amounts of 1% by weight to 25% by weight, in particular 5% by weight to 15% by weight.
  • the quaternary ammonium compounds suitable for the agent according to the invention are preferably pyridines N-alkylated with Cio to C22 alkyl groups, optionally halogen and / or substituted with Ci to C4 alkyl groups, to Ci- to Ciss- Alkyl or benzyl groups N.N'-dialkylated idazolines, optionally substituted with C 1 -C 6 -alkyl groups, and compounds of the formula I,
  • R * and R 2 independently of one another alkyl radicals each having 1 to 3 carbon atoms or benzyl, halogenated or alkylated benzyl radicals, R3 and R ⁇ independently of one another alkyl, benzyl or halogenated or alkylated benzyl radicals each having 7 to 22 C.
  • -Atoms and X “an anion from the group comprising sulfate, hydrogen sulfate, the halides and carboxylates, as well their mixtures.
  • Such quaternary ammonium compounds are preferably contained in the compositions according to the invention in amounts of 0.5% by weight to 50% by weight, in particular 2% by weight to 20% by weight, based in each case on the complete composition .
  • the particularly suitable quaternary ammonium salts include C 1 -C 6 -alkyl-substituted N-alkylated pyridinium compounds, N, N'-dialkylated, 2-position C 1 -C-substituted alkyl-2-imidazolinium compounds and / or compounds of the formula I, in which R and R 2 are methyl radicals, R is an alkyl radical with 8 to 18 carbon atoms or a benzyl or chlorinated benzyl est, and R 4 is an alkyl radical with 8 to 18 carbon atoms.
  • N-decylpyridinium chloride N-dodecylpyridinium chloride, N-tetradecylpyridinium chloride, N-hexadecylpyridinium chloride, 1,3-dimethyl-2-heptyl-i ⁇ ' dazolinium chloride, 1,3-dimethyl-2-nonyl-imidazolinium chloride, 1-methyl -2-heptadecyl-3-benz l-imidazolinium chloride, l-dec l-2,3-dimethyl-imidazolinium chloride, l-dodecyl-2-methyl-3-benzyl-imidazolinium chloride, l-benzyl-2-methyl-3-octadecyl -imidazolinium chloride, 1-benzyl-2-methyl-1-3-dodecyl-imidazolinium chloride, dimethyl-dioctyl-ammonium chloride, did
  • Phenolic active substances suitable for the process according to the invention are, in particular, the compounds of the group comprising phenol, o-phenylphenol, cresol, thymol and their mono- or poly-halogenated derivatives, for example p-chloro-m-cresol, 4-chlorothymol, 5-chlorine -2- (2,4-di-chlorophenoxy) phenol and 2,2'-thio-bis- (4-chlorophenol) belong, as well as their mixtures.
  • Such phenolic active ingredients are preferably used in the compositions according to the invention in amounts of 0.5% by weight to 50% by weight, in particular Special from 3 wt .-% to 20 wt .-%, each based on the complete agent.
  • the isothiazolinones suitable for use in the agents according to the invention include, in particular, 1,2-benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3 -on and 2-0ctyl-4-isothiazolin-3-one.
  • Such isothiazolinones are contained in the agents according to the invention preferably in amounts of 0.2% by weight to 20% by weight, in particular from 0.5% by weight to 10% by weight, in each case based on the complete agent .
  • the slime control agent according to the invention preferably contains 0.5% by weight to 75% by weight, in particular 5% by weight to 50% by weight, of cysteine and / or cysteine derivative. This amount can vary depending on the microbicidal active ingredients present at the same time and, in the presence of aldehydic active ingredients, is preferably 0.5% by weight to 25% by weight, in particular 2% by weight to 10% by weight. , in the presence of isothiazolinones preferably 1% by weight to 20% by weight, in particular 2% by weight to 10% by weight and in the presence of phenolic active substances preferably 2% by weight to 50% by weight. -%, in particular 5 wt .-% to 20 wt .-%, each based on the total agent.
  • the pH of the slime control agents according to the invention can be adjusted to a value required for the desired application by adding small amounts, in particular not more than 1% by weight, based on the total agent, of known acids or alkalis.
  • the agents according to the invention are preferably free of acid or alkali additives.
  • the slimicide according to the invention can moreover contain constituents customary in microbicidal agents, such as dyes, corrosion inhibitors, antioxidants, surfactants and / or complexing agents, and, if appropriate, further antimicrobially active compounds. These constituents are preferably present in amounts of not more than 15% by weight, in particular not more than 5% by weight, based on the total composition.
  • the preparation of the agents according to the invention has no special features. It is advantageously carried out by simply mixing the constituents, it being possible to use the individual components in bulk or, preferably in the preparation of liquid agents, in the form of aqueous solutions, some of which are commercially available.
  • compositions of the invention may exist as concentrated aqueous solutions, which are diluted by adding water or the fluid-carrying system liquid flowing through 'to the desired application concentration.
  • agents according to the invention are preferably in solid form, for example as a powder.
  • the unexpectedly advantageous antimicrobial effect of the process according to the invention is expressed in that the use of cysteine and / or a cysteine derivative in combination with a microbicidal active ingredient prevents the formation of bio-mucilages much more effectively, that is to say at lower active ingredient concentrations, than this with knowledge of the effect of the individual components would have been expected.
  • the method according to the invention makes it possible to effectively remove already existing, coated, firmly adhering bacterial colonies and films from the populated surfaces.
  • compositions M1 to M12 characterized by their composition in Table 2 were produced (proportions in% by weight).
  • aqueous solutions with the concentrations given in Table 4 were prepared from agents M5 and M6 and used against slime-forming microorganisms (Enterobacter cloacae) (exposure time 6 hours and 24 hours, respectively).
  • compositions containing the combination of cysteine derivative and microbicidal active ingredient according to the invention have a significantly stronger antimicrobial activity than the compositions containing only the microbicidal active ingredient. This allows the agents according to the invention to be used to control mucus in liquid-carrying systems in technical plants at significantly lower concentrations than would be necessary if the microbicides were used alone.
  • a tubular piece (“Robbins device"), as described by WF McCoy, JD Bryers, J. Robbins and JW Costerton in Can. J. Microbiol. 27. (1981), 910 and into which plastic plastic plugs were inserted.
  • the tube system was filled with a nutrient medium consisting of 5.3 g of glucose, 5.3 g of yeast extract, 13.3 g of malt extract and 0.13 g of calcium carbonate per liter of aqueous solution inoculates mucus-forming bacterial strain which had been isolated from the central disinfectant supply line of a hospital.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)
  • Finger-Pressure Massage (AREA)

Abstract

De la cystéine et/ou des dérivés de cystéine sont utilisés pour combattre des biomucilages dans des systèmes véhiculant des liquides dans des installations techniques. Ces substances sont avantageusement utilisées dans le procédé décrit, lequel consiste essentiellement à ajouter de la cystéine et/ou un dérivé de cystéine et une substance active microbicide choisie dans le groupe des substances actives aldhéhydiques, des composés d'ammonium quaternaires, des substances actives phénoliques, des isothiazolinones et des mélanges de ceux-ci, au milieu liquide du système véhiculant des liquides, de sorte que des concentrations efficaces des substances actives soient présentes dans le liquide antisalissure. On y parvient en ajoutant les constituants individuels en quantités dosés, ou avantageusement en ajoutant l'agent décrit qui renferme une combinaison de cystéine et/ou de dérivés de cystéine avec une substance active microbicide appropriée.
EP90917196A 1989-11-16 1990-11-08 Lutte contre des micro-organismes mucilagineux Withdrawn EP0500712A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE3938130A DE3938130A1 (de) 1989-11-16 1989-11-16 Verwendung von cysteinderivaten zur bekaempfung von schleimbildenden mikroorganismen und bioschleimen
DE3938130 1989-11-16
DE4007227 1990-03-07
DE4007227A DE4007227A1 (de) 1990-03-07 1990-03-07 Verfahren zur bekaempfung von schleimbildenden mikroorganismen
DE4028245A DE4028245A1 (de) 1990-09-06 1990-09-06 Verfahren zur bekaempfung von schleimbildenden mikroorganismen
DE4028245 1990-09-06

Publications (1)

Publication Number Publication Date
EP0500712A1 true EP0500712A1 (fr) 1992-09-02

Family

ID=27200453

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90917196A Withdrawn EP0500712A1 (fr) 1989-11-16 1990-11-08 Lutte contre des micro-organismes mucilagineux

Country Status (5)

Country Link
EP (1) EP0500712A1 (fr)
JP (1) JPH05503085A (fr)
AU (1) AU6752990A (fr)
FI (1) FI922186L (fr)
WO (1) WO1991007090A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0542489A3 (en) * 1991-11-14 1993-08-04 Rohm And Haas Company Microbicidal compositions comprising 3-isothiazolones and polycations
ATE210975T1 (de) * 1994-06-23 2002-01-15 Procter & Gamble Topisch anzuwendende zubereitungen enthaltend n- acetyl-l-cystein
NZ286510A (en) * 1995-05-15 1998-06-26 Rohm & Haas Method of detoxifying biocide in waste water using a water soluble thio compound
JP3722268B2 (ja) * 1998-09-03 2005-11-30 栗田工業株式会社 抗菌性組成物
AU2042200A (en) 1998-12-07 2000-06-26 Baylor College Of Medicine Preventing and removing biofilm from the surface of medical devices
CN1961666B (zh) 2001-01-04 2011-06-22 拜奥特罗尔股份有限公司 抗微生物组合物
ITMI20021881A1 (it) * 2002-09-04 2004-03-05 Zambon Spa Composizioni farmaceutiche per il trattamento di infezioni da patogeni dell'apparato urinario.
RU2413538C2 (ru) * 2005-03-21 2011-03-10 Сютакоат Аб Противомикробное средство, содержащее цистеиновое соединение, ковалентно связанное с субстратом, в частности, связыванием при помощи s-s мостика через спейсерную молекулу
GB0713799D0 (en) 2007-07-17 2007-08-22 Byotrol Llc Anti-microbial compositions
JP5615708B2 (ja) 2007-09-17 2014-10-29 バイオトロル・ピーエルシー 抗微生物組成物を含む製剤
CN102791262A (zh) * 2010-01-08 2012-11-21 哈佛大学校长及研究员协会 用于处理生物薄膜的d-氨基酸
BR112019027923A2 (pt) * 2017-06-28 2020-07-21 DDP Specialty Electronic Materials US, Inc. composição microbicida sinérgica, método para controlar o crescimento de microrganismos em um meio aquoso, e, método para controlar um biofilme.

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2118925B (en) * 1982-04-19 1985-06-26 Dearborn Chemical Limited Biocide
EP0217339A3 (fr) * 1985-09-30 1988-01-07 Union Carbide Corporation Traitement de l'eau par une composition algicide
DE3722044A1 (de) * 1987-07-03 1989-01-12 Hoechst Ag Mittel zur inaktivierung von sporen sowie verfahren zur verlaengerung der haltbarkeit von produkten, stoffen oder erzeugnissen, die durch bakteriellen sporenbefall verderblich sind
US5004749A (en) * 1989-04-20 1991-04-02 Imperial Chemical Industries Plc Concentrated aqueous solution of glutaraldehyde and 1,2-benzisothiazolin-3-one

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9107090A1 *

Also Published As

Publication number Publication date
FI922186A0 (fi) 1992-05-13
AU6752990A (en) 1991-06-13
FI922186A7 (fi) 1992-05-13
JPH05503085A (ja) 1993-05-27
FI922186L (fi) 1992-05-13
WO1991007090A1 (fr) 1991-05-30

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