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WO1993006729A1 - Melanges de substances actives a effet antimicrobien - Google Patents

Melanges de substances actives a effet antimicrobien Download PDF

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Publication number
WO1993006729A1
WO1993006729A1 PCT/EP1992/002200 EP9202200W WO9306729A1 WO 1993006729 A1 WO1993006729 A1 WO 1993006729A1 EP 9202200 W EP9202200 W EP 9202200W WO 9306729 A1 WO9306729 A1 WO 9306729A1
Authority
WO
WIPO (PCT)
Prior art keywords
antimicrobial
mixtures according
antimicrobially active
radicals
carbon atoms
Prior art date
Application number
PCT/EP1992/002200
Other languages
German (de)
English (en)
Inventor
Rudolf Lehmann
Hans-Theo Leinen
Harald Kluschanzoff
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to JP5506585A priority Critical patent/JPH07500097A/ja
Priority to EP92920153A priority patent/EP0606290A1/fr
Publication of WO1993006729A1 publication Critical patent/WO1993006729A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/025—Preservatives, e.g. antimicrobial agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C1/00—Chemical treatment prior to tanning
    • C14C1/02—Curing raw hides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Definitions

  • the invention relates to antimicrobial active substance mixtures, in particular fungistatically active mixtures containing chloroacetamide or its derivatives and iodopropynyloxyethanol carbamate compounds.
  • the invention relates to antimicrobial mixtures comprising a) at least one antimicrobial chloroacetamide or substituted chloroacetamide and b) at least one antimicrobially active iodopropynyloxyethanol carbamate compound, components a and b being in a weight ratio of a: b in the range from 300: 1 to 0.05: 1.
  • Chloracetamides which have the formula I are suitable as antimicrobial substances
  • antimicrobial compounds can be contained in the mixtures according to the invention as chemical individuals or as mixtures.
  • antimicrobial compounds are N- (4-bromo-2-methylphenyl) -2-chloroacetamide, according to EP 137 729 A2 or N-methyl-N-heptylchloroacetamide.
  • Suitable antimicrobial iodopropynyloxyethanol carbamate compounds are, in particular, 2- (3-iodo-2-propynyloxy) ethanol carbamates of the general formula (II)
  • R 1 and R 2 are identical or different and are hydrogen, linear or branched alkyl or alkenyl radicals having 1 to 6 carbon atoms or cyclic alkyl radicals having 5 to 7 carbon atoms or R * and R 2 taken together - (CH 2 ) n -, , where n is 4 to 6,
  • R 3 , R 4 , R 5 and R 6 which may be the same or different, are hydrogen, alkyl radicals having 1 to 4 carbon atoms, aryl radicals or CCI 3 or R 3 and R 5 or R 4 and R 6 taken together represent - (CH 2 ) n , where n is 3 to 5, and
  • R 7 is hydrogen, linear or branched alkyl radicals having 1 to 12 carbon atoms or cyclic alkyl radicals having 4 to 8 carbon atoms, aryl radicals, substituted aryl radicals, arylalkyl radicals or arylsulfonyl radicals means.
  • linear or branched alkyl radicals or alkenyl radicals with 1 to 6 carbon atoms for which R 1 and R 2 stand, are the methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec.-butyl , tert-butyl, pentyl, the hexyl radical and their branched isomers such as the vinyl, allyl, propenyl, butenyl, pentenyl and hexenyl radicals and the corresponding isomers of the alkenyls mentioned with 4, 5 and 6 carbon atoms.
  • cyclic alkyl radicals having 5 to 7 carbon atoms for which R 1 and R 2 stand, are the cyclopentane, cyclohexane and cycloheptane radicals.
  • Compounds of the formula (II) in which both substituents R 1 and R 2 are simultaneously hydrogen or simultaneously methyl radicals are preferred, and compounds in which one of R * and R 2 is hydrogen while the other represents a methyl radical.
  • alkyl radicals with 1 to 4 carbon atoms which R 3 , R 4 , R 5 and R 6 represent, are the methyl, ethyl, propyl, isopropyl and n-butyl radical, isobutyl, sec-butyl and tert-butyl, with methyl being preferred.
  • aryl radicals represented by R 3 , R 4 , R 5 and R 6 are the phenyl and the naphthyl radical.
  • cyclic alkyl radicals with 4 to 8 carbon atoms for which R7 stands, are the cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl radical.
  • aryl and substituted aryl which R 7 represents are the phenyl, naphthyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, dichlorophenyl and the trichlorophenyl radical.
  • Examples of aralkyl and arylsulfonyl for which R 7 stands are the benzyl and p-toluenesulfonyl radicals.
  • R 7 is a lower alkyl radical having 1 to 4 carbon atoms and an aryl radical or aryl radical substituted by chlorine or bromine are preferred.
  • R 7 is a propyl, butyl or phenyl radical.
  • N-substituted 2- (3-iodo-2-propynyloxy) ethanol carbamates of the general formula (II) are prepared by methods known per se (Houben-Weyl, Methods of Org. Chemistry, Vol. 8, p. 141 - 144 (1952)) by reacting equimolar amounts of the alcohols with suitable, for example Commercially available isocyanates are synthesized, as described, for example, in DE 32 16 894 Al and in DE 32 16 895 Al.
  • the weight ratio of components a and b is set in the range from 100: 1 to 0.1: 1.
  • the antimicrobial mixtures according to the invention can be provided in the form of powdered or solvent-containing concentrates in which the total concentration of components a and b is from about 0.5 to 100, preferably from 10 to 90,% by weight can.
  • Suitable ready-to-use agents have in particular a concentration of 10 to 50% by weight of the mixture of a and b according to the invention.
  • the mixtures intended for practical use still contain a total of 0 to about 99, preferably 90 to 10% by weight of further commonly used constituents which are selected depending on the intended form of use and the intended use.
  • water-miscible organic solvents are suitable as solvents, for example ethanol, isopropanol and ethylene glycol, propylene glycol, ethylethylene glycol, propylpropylene glycol and water-immiscible solvents such as white spirit, benzene, toluene, ethyl acetate or dimethylene chloride.
  • the mixtures according to the invention can also contain surfactants, in particular nonionic surfactants.
  • suitable surfactants are adducts of 4 to 40, preferably 4 to 20, moles of ethylene oxide with one mole of fatty alcohol, alkylcyclohexanol, alkylphenol, fatty acid, fatty acid amide or alkanesulfonamide.
  • Addition products of 5 to 16 moles of ethylene oxide with coconut oil or tallow fatty alcohols, with oleyl alcohol, a mixture of oleyl alcohol and cetyl alcohol and with mono-, di- or trialkylphenols and with monoalkylcyclohexanols with 6 to 14 carbon atoms in the alkyl radicals are of particular interest.
  • Mixed addition products of ethylene oxide and propylene oxide onto the compounds mentioned with an active hydrogen atom are also suitable.
  • the alkoxylation products mentioned can also be end-capped, for example by ether or acetal groups.
  • the amount of surfactant can be about 0.001 to about 2, preferably about 0.01 to 0.15% by weight, based on the compound.
  • Builders may also be present in the mixtures according to the invention; Suitable as such are, for example, alkali metal salts of gluconic acid, in particular sodium gluconate, the alkali metal salts of nitrilotriacetic acid, ethylenediaminetetraacetic acid, hydroxyethane diphosphonic acid, phosphonobutane tricarboxylic acid, lactic acid, citric acid or tartaric acid.
  • the water-soluble salts of higher molecular weight polycarboxylic acids for example polymers of maleic acid, itaconic acid, fumaric acid and citraconic acid, are also suitable as builders. Copolymers of these acids with one another or with other polymerizable monomers, such as e.g.
  • Ethylene, propylene, acrylic acid, vinyl acetate, isobutylene, acrylamide and styrene are useful.
  • the amounts of the builder substances can be about 0.01 to 2, preferably 0.02 to 1.0,% by weight, based on the compound.
  • Cleaning enhancers such as fatty acid mono- and diethanolamides, for example coconut fatty acid monoethanolamide and coconut fatty acid diethanolamide, and addition products of up to 4 moles of ethylene oxide or propylene oxide with fatty alcohols with 8 to 12 carbon atoms and free fatty alcohols with 8 to 12 carbon atoms as well as cleaning enhancers based on cellulose can also be incorporated into the mixtures according to the invention .
  • the amounts of cleaning boosters can be about 0.001 to 0.02, preferably about 0.005 to 0.01% by weight, based on the compound.
  • the mixtures according to the invention contain, in addition to the combination of chloroacetamide compounds and iodopropynyloxyethanol carbamate compounds according to the invention, further antimicrobial substances.
  • Insecticides such as pyrethrofde (permethrin, cypermethrin, decamethrin and fenvalerate) and / or lindane, endosulfan, dieldrin can also be incorporated into the mixtures according to the invention.
  • the amounts of these additives are said to be lower than those of the two components used according to the invention.
  • the amounts of the possible components used to assemble the agents according to the invention are generally based on commercial and price specifications and are in principle not of inventive importance.
  • solid products preferably in powder or granule form, which contain the antimicrobial mixtures according to the invention can also be provided for the production of ready-to-use preservatives.
  • the antimicrobial, synergistically active mixtures according to the invention can be used as disinfectants and preservatives in many areas, for example in households and in trade, such as hospitals, schools, bathing establishments, public transport, commercial plants and industrial plants in the anti-mold finishing of carpets, wall coverings and sealing compounds.
  • the synergistic mixtures can be used to preserve plant propagation material, in particular seeds and flower bulbs.
  • the mixtures according to the invention can be used in the preservation of technical products still to be processed, such as glazes, lacquer and dispersion and emulsion paints, adhesives and pastes, drilling and cutting oils or products from the paper, cardboard or leather-processing industry, and for the preservation of industrial and Find domestic water application.
  • the mixtures according to the invention can also be used for finished material protection, for example for anti-mold finishing of plasters, paints, plastics, floor or wall coverings made of textiles, paper, plastics, leather, cork or for impregnating wood.
  • boxes such as those used in commercial mushroom cultivation can be effectively equipped against attack by the culture mycelium.
  • the application can take place, for example, by spraying, brushing, brushing, knife coating, dipping or pressure or vacuum impregnation.
  • the application concentrations are generally about 0.001 to 5, preferably about 0.01 to 2,% by weight of active substance mixture. Examples
  • the antimicrobial chloroacetamide compounds used were N- (4-bromo-2-methylenephenyl) -2-chloroacetamide (product A).
  • the following compounds of the formula (III) were used as antimicrobial iodopropynyloxyethanol carbamates (product B):
  • microbistatic activity of the mixtures AB 1 to AB 5 according to the invention in comparison with the individual components (products A and B) was determined with respect to the following test germ suspensions: 1. Staphylococcus aureus 2 ⁇ 10 9 germs / ml
  • Candida albicans 1 ⁇ 10 8 germs / ml
  • the inhibitory concentrations of the products to be tested were based on the guidelines for the testing and evaluation of chemical disinfection processes, chapter 2.1, printed in Zbl. Bakt. Hyg., I. Dept. Orig. 172, 536-537 (1981).
  • the substance mixtures AB 1 to AB 5 and di individual components A and B were dissolved in stock solutions in dimethylformamide, from which the corresponding dilution series were prepared by adding wort broth in a volume ratio of 1:50.
  • Mixtures AB 1 to AB 5 each contain the quantities of the individual components men that were used in the weight ratios indicated above.
  • Chloroacetamide (Product C) was used as the antimicrobial chloroacetamide compound.
  • Product B was used as the antimicrobial iodopropynyloxyethanol carbamate compound.
  • Product C was combined with product B to the following mixtures according to the invention:
  • N-Methyl-N-heptylchloroacetamide (product D) was used as the antimicrobial chloracetamide compound.
  • Product B was used as an antimicrobial iodopropynyloxyethanol carbamate compound.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Mélanges de substances actives à effet antimicrobien contenant des composés de chloracétamide et des composés d'iodopropinyloxy-éthanol-carbamate, dans un rapport pondéral de 300:1 à 0,05:1, et leur application pour l'apprêtage fongistatique de produits à usage domestique et industriel.
PCT/EP1992/002200 1991-10-02 1992-09-23 Melanges de substances actives a effet antimicrobien WO1993006729A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP5506585A JPH07500097A (ja) 1991-10-02 1992-09-23 抗菌性混合物
EP92920153A EP0606290A1 (fr) 1991-10-02 1992-09-23 Melanges de substances actives a effet antimicrobien

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914132772 DE4132772A1 (de) 1991-10-02 1991-10-02 Antimikrobielle wirkstoffgemische
DEP4132772.1 1991-10-02

Publications (1)

Publication Number Publication Date
WO1993006729A1 true WO1993006729A1 (fr) 1993-04-15

Family

ID=6441965

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/002200 WO1993006729A1 (fr) 1991-10-02 1992-09-23 Melanges de substances actives a effet antimicrobien

Country Status (5)

Country Link
EP (1) EP0606290A1 (fr)
JP (1) JPH07500097A (fr)
AU (1) AU2640692A (fr)
DE (1) DE4132772A1 (fr)
WO (1) WO1993006729A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0093962A1 (fr) * 1982-05-06 1983-11-16 Henkel Kommanditgesellschaft auf Aktien Carbamate de 2(3-iodo-2-propynyloxy)-éthanol préparation et utilisation comme substance microbicide
EP0299191A1 (fr) * 1987-06-09 1989-01-18 Henkel Kommanditgesellschaft auf Aktien Mélange d'agents actifs fongicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0093962A1 (fr) * 1982-05-06 1983-11-16 Henkel Kommanditgesellschaft auf Aktien Carbamate de 2(3-iodo-2-propynyloxy)-éthanol préparation et utilisation comme substance microbicide
EP0299191A1 (fr) * 1987-06-09 1989-01-18 Henkel Kommanditgesellschaft auf Aktien Mélange d'agents actifs fongicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SEIFEN, OLE, FETTE, WACHSE Bd. 102, Nr. 19, 1976, AUGSBURG DE Seite 557 G.SCHMIDT 'Die in der Kosmetik gebra}chlichen bakteriziden Wirkstoffe' in der Anmeldung erwähnt *

Also Published As

Publication number Publication date
JPH07500097A (ja) 1995-01-05
DE4132772A1 (de) 1993-04-08
EP0606290A1 (fr) 1994-07-20
AU2640692A (en) 1993-05-03

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