EP1268917A1 - Utilisation de 3-iodo-2-propinyl-carbamates comme principe actif antimicrobien - Google Patents

Utilisation de 3-iodo-2-propinyl-carbamates comme principe actif antimicrobien

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Publication number
EP1268917A1
EP1268917A1 EP01936157A EP01936157A EP1268917A1 EP 1268917 A1 EP1268917 A1 EP 1268917A1 EP 01936157 A EP01936157 A EP 01936157A EP 01936157 A EP01936157 A EP 01936157A EP 1268917 A1 EP1268917 A1 EP 1268917A1
Authority
EP
European Patent Office
Prior art keywords
iodo
propynyl
carbamates
ipbc
several
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Withdrawn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
EP01936157A
Other languages
German (de)
English (en)
Inventor
Michael Heinzel
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
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1268917A1 publication Critical patent/EP1268917A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/164—Organic compounds containing a carbon-carbon triple bond
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/24—Organic compounds containing halogen
    • 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
    • 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
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/12—Processes in which the treating agent is incorporated in microcapsules

Definitions

  • the present invention relates to the use of 3-iodo-2-propynylcarbamates as antimicrobial, in particular antimycotic, active ingredients in detergents; Cleaning agents; Hand washing; Hand dishwashing detergents; Dishwasher detergents and agents for finishing textiles, furs, furs or leather.
  • Hygiene in the washing and cleaning process means not only the removal of visible dirt but also the rendering harmless of germs that have contaminated the items to be cleaned, such as laundry, for use. Such germs are viruses and bacteria, but especially fungi. Hygiene, in particular laundry hygiene, is therefore of particular importance in the commercial sector, where textiles from hospitals, hotels, restaurants, etc. are reprocessed that do not circulate within a specific group of users, but are used by ever different users.
  • washing machines and dishwashers especially those that are not used for a long time, can also lead to hygienic problems and olfactory annoyances due to the strong growth of germs in the hoses, the pump or the dispenser. If laundry remains damp in the washing machine for a longer period of time, it can fungus - this leads to the well-known foxing.
  • EP-B-0 093 962 describes 2- (3-iodo-2-propynyloxy) ethyl carbamates and their use for the preservation of technical products (e.g. paints, glues, dispersions, cooling lubricants) for the antimicrobial finishing of Joint sealants, for combating mold on walls, ceilings or wooden floors, for antimicrobial finishing of plastics such as B. PVC films and known as preservatives for cosmetics.
  • technical products e.g. paints, glues, dispersions, cooling lubricants
  • IPBC 3-Iodine-2-propynyl butyl carbamate
  • the present invention has for its object to provide agents that have an antimicrobial and in particular antimycotic effect and are suitable for overcoming the above-mentioned disadvantages from the prior art.
  • 3-iodo-2-propynylcarbamates in particular IPBC, also have antimicrobial and, in particular, antimycotic activity as a constituent of detergents and cleaning agents.
  • This finding was particularly surprising because the uses of 2- (3-iodo-2-propynyloxy) ethyl carbamates known from the prior art and of IPBC made it necessary to keep the active ingredient permanently in the product to be preserved or to be antimicrobially treated suggest.
  • the present invention therefore relates to the use of 3-iodo-2-propynylcarbamates of the formula (I) as an antimicrobial and in particular antimycotic active ingredient in detergents; Cleaning agents; Hand washing; Hand dishwashing detergents and machine dishwashing detergents as well as textile, fur and leather finishing agents.
  • R 1 and R 2 are the same or different and are hydrogen, linear or branched alkyl radicals having 1 to 6 carbon atoms;
  • R 3 , R 4 , R 5 and R 6 which may be the same or different, are hydrogen or
  • alkyl radicals having 1 to 4 carbon atoms are alkyl radicals having 1 to 4 carbon atoms
  • R is hydrogen, linear or branched alkyl radicals having 1 to 12 carbon atoms. men or a cyclohexyl radical, a phenyl radical, a substituted phenyl radical, a benzyl radical or a p-toluenesulfonyl radical and n is 0 or 1.
  • a carbamate which can preferably be used according to the invention is IPBC, which corresponds to the formula I, where R 1 and R 2 are hydrogen, n is 0 and R is butyl- (-C 4 H 9 ), in particular n-butyl.
  • the 3-iodo-2-propynylcarbamates are prepared, for example, by equimolar amounts of the alcohols of the general formula (II)
  • R 2 , R 3 , R 4 , R 5 , R 6 and R and n have the meanings given for the formula (I).
  • Examples of linear or branched alkyl radicals having 1 to 6 carbon atoms, for which R 1 and R 2 are, are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl and their branched isomers.
  • Compounds of the formula (I) in which both substituents R 1 and R 2 are simultaneously hydrogen or simultaneously methyl are preferably used, so such as those in which one of R 1 and R 2 is hydrogen while the other is methyl.
  • alkyl radicals with 1 to 4 carbon atoms for which R 3 .
  • linear and branched alkyl radicals with 1 to 12 carbon atoms examples include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl. Heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the branched isomers of alkyls with 5 to 12 carbon atoms.
  • substituted phenyl radicals which R represents are chlorophenyl
  • R is a lower alkyl radical having 1 to 4 carbon atoms or a phenyl radical or a phenyl radical substituted by chlorine or bromine are preferably usable.
  • Examples of particularly preferred compounds are those in which R is propyl, butyl or phenyl.
  • the N-substituted 3-iodo-2-propynylcarbamates of the general formula (I) are obtained by methods known per se (Houben-Weyl, Methods of Org. Chemistry, Vol. 8, pp. 141-144 (1952)) Implementation of equimolar amounts of the alcohols of the general formula (II) with suitable, for. B. synthesized commercially available isocyanates of the general formula (IM). The reaction is carried out at temperatures from about 10 ° C to about 70 ° C. preferably from about 20 ° C to about 30 ° C.
  • the reactions are generally carried out in an inert solvent. Examples are ethylene chloride. Dimethylformamide. Toluene. Chlorobenzene. Methylene chloride and tetrahydrofuran called.
  • Catalysts such as dibutyltin dilaurate have proven suitable.
  • Other catalysts that can be used are: dibutyltin diacetate and tert.
  • Bases such as triethylamine.
  • alcohols of the general formula (II) are:
  • isocyanates are methyl isocyanate, ethyl isocyanate, propyl isocyanate, butyl isocyanate, phenyl isocyanate, 4-chlorophenyl isocyanate, cyclohexyl isocyanate, 4-fluorophenyl isocyanate, 3,4-dichlorophenyl isocyanate, 2,4,5-trichlorophenyl isocyanate and p-toluenesulfonyl isocyanate.
  • the 3-iodo-2-propynylcarbamates which can be used according to the invention are added to the liquid compositions in which they are to have their action in a manner known to those skilled in the art.
  • the 3-iodo-2-propynylcarbamates which can be used according to the invention can either be added to the liquid or pasty base materials from which the solid compositions are made or applied to the solid compositions, for example by spraying.
  • the 3-iodo-2-propynylcarbamates which can be used according to the invention are preferably the detergents; Cleaning agents; Hand washing; hand- schirr Pattersonschn; Machine dishwashing detergents and agents for finishing textiles, furs, skins or leather in an organic solvent, in particular in an alcoholic solution, particularly preferably in an ethanolic solution.
  • the 3-iodo-2-propynylcarbamates which can be used according to the invention are added to the abovementioned agents in nanoscale form.
  • Nanoscale substances are substances whose particle diameter in the direction of the greatest expansion of the particles is less than 1000 nm (nanometers).
  • the particle diameter of the 3-iodo-2-propynylcarbamates which can be used according to the invention is approximately 5 to 500 nm, preferably 10 to 150 nm.
  • nanoparticulate is used synonymously with the term “nanoscale” in the present document.
  • the nanoscale active substances which can be used according to the invention consist of a discrete phase of the active substance, on the surface of which at least one surface-modifying substance is preferably adsorbed.
  • Emulsifiers and / or protective colloids are particularly suitable as surface-modifying substances.
  • the coating of the particles with emulsifiers and / or protective colloids means that there is no subsequent agglomeration of the particles.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil (6) polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several of these classes of substances are also suitable;
  • Partial esters based on linear, branched, unsaturated or saturated C 6/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), sucrose, alkyl glucosides (e.g. Methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (eg cellulose);
  • alkyl glucosides e.g. Methyl glucoside, butyl glucoside, lauryl glucoside
  • polyglucosides eg cellulose
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters, and sorbitan mono- and diesters with fatty acids or with castor oil are known, commercially available products. whose average degree of alkoxylation is the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C 12 18 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 2024051 as refatting agents for cosmetic preparations.
  • C 8 / i 8 alkyl mono- and oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bound to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • anionic emulsifiers are soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether ether sulfates, mono sulfate ether sulfates, mono -sulfosuccinates, mono- and dialkylsulfosuccinamates, sulfotriglycides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acyl amino acids such as acyl amino acids
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the trimethylammonium glycinate, cocoalkyldimethylammonium glycinate, N-acylamino-propyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium, and 2-glycinate, Alkyl-3-carboxylmethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and also the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the trimethylammonium glycinate, cocoalkyldimethylammonium glycinate, N
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ / i ⁇ -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts .
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyl taurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkyl- laminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • ampholytic surfactants are N-cocoalkyl aminopropionate, cocoacylaminoethyl aminopropionate and of C 12/1 8 - sarcosine.
  • ampholytic emulsifiers quaternary emulsifiers are also suitable, those of the ester quat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • anionic emulsifiers are alkyl sulfates, alkyl ether sulfates and monoglyceride (ether) sulfates.
  • the active ingredients and the emulsifiers are used in a weight ratio of 1: 100 to 100: 1, preferably 1:25 to 25: 1 and in particular 1:10 to 10: 1.
  • Emulsifiers which are capable of forming microemulsions are particularly preferred.
  • Suitable protective colloids are, for example, gelatin, casein, gum arabic, lysalbic acid, starch, carboxymethyl cellulose or modified carboxymethyl cellulose.
  • cellulose and polymers such as polyvinyl alcohols, polyvinyl pyrrolidones, polyalkylene glycols and polyacrylates.
  • the 3-iodo-2-propynylcarbamates which can be used according to the invention can also be used as nanoparticles which are encased by one or more emulsifiers and / or protective colloids.
  • Corresponding nanoparticles can be produced, for example, by introducing (a) 3-iodo-2-propynyl-carbamates into a liquid phase in which they are not soluble,
  • Evaporation technology offers another suitable method for producing the nanoscale particles.
  • the starting materials are first in a suitable organic solvent (e.g. alkanes, vegetable oils,
  • the PCA method (Precipitation with a Compressed Fluid Anti-Solvent) is similarly suitable.
  • the primary solution of the starting materials is introduced into a supercritical fluid, whereby finely divided droplets form in which diffusion processes take place, so that the finest particles are precipitated.
  • the raw materials are melted by injecting gas (e.g. carbon dioxide or propane). Pressure and temperature reach near or supercritical conditions.
  • gas e.g. carbon dioxide or propane
  • Pressure and temperature reach near or supercritical conditions.
  • the gas phase dissolves in the solid and causes a lowering of the melting temperature, the viscosity and the surface tension.
  • cooling effects lead to the formation of very fine particles.
  • the concentration of the 3-iodo-2-propynylcarbamates which can be used according to the invention in the agents can be varied within a wide range by the person skilled in the art can be varied depending on the conditions in which the agents are used.
  • the amount of dissolved or nanoscale 3-iodo-2-propynyl-carbamates is chosen so that the concentration of 3-iodo-2-propynyl-carbamates is usually in the order of 0.001 to 5, preferably 0.01 to 2 and in particular 0 , 1 to 1 wt .-% based on the preparations.
  • Other objects of the present invention are detergents; Cleaning supplies; rinse; Hand washing; Hand dishwashing detergents; Machine dishwashing detergents and agents for finishing textiles, furs, furs or leather, which contain a 3-iodo-2-propynyl carbamate of the formula (I) or more 3-iodo-2-propynyl carbamates, in particular those that contain IPBC.
  • Preferred objects of the present invention are detergents; Cleaning supplies; rinse; Hand washing; Hand dishwashing detergents; Machine dishwashing detergents and agents for finishing textiles, furs, skins or leather, to which 3-iodine-2-propynyl-carbamates, in particular IPBC, have been added in nanoparticulate form.
  • Another object of the present invention is the use of 3-iodo-2-propynylcarbamates of the formula I, in particular of IPBC, as an antimicrobial and in particular antimycotic active ingredient in agents for the antimicrobial finishing of textiles, furs, skins or leather.
  • the textiles, furs, skins or leather are finished in a manner known to those skilled in the art, for example by immersing the textiles, furs, skins or leather in a suitably concentrated solution of an agent according to the invention.
  • IPBC (30% in dipropylene glycol), obtained from Milker & Grüning GmbH, Horhausen, was prediluted as follows because of the poor water solubility:
  • An alcoholic stock solution with 1% active ingredient was prepared by weighing 3.34 g of 30% IPBC in 100 ml of 99% ethanol and in subsequent dilutions in double dist. H 2 O further diluted to the required test solutions. These were:
  • An antibacterial and antimycotic formulation was used as the reference preparation, comprising 70% by weight didecyldimethylammonium chloride, 15% by weight ethylene glycol, the rest water.
  • the reference preparation was also diluted with double-distilled water.
  • Candida albicans ATCC 10231, (pre-breeding on CaSo agar, 4d / 25 ° C), Aspergillus niger, ATCC 6275, (pre-breeding on malt agar, 8d / 25 ° C), Trichophyton mentagrophytes, ATCC 9533, (pre-breeding on malt agar , 8d / 25 ° C), Cladosporium cladosporioides, DSM 62121, (pre-cultivation on malt agar, 8d / 25 ° C), Epicoccum nigrum, self-isolate, (pre-cultivation on malt agar, 8d / 25 ° C)
  • the inocula were obtained by washing off the pre-cultivated plates with 0.05% Tween ® 80 and had the following germ contents:
  • Candida albicans 1.9 x 10 9 CFU / ml
  • Cladosporium cladosporioides 5.0x10 7 CFU / ml
  • test specimens made from standard cotton fabric according to DIN 53919 (WfK Testgewebe-GmbH, Adlerstrasse 42, Krefeld) were placed in the test sample for 15 minutes. inserted, then removed sterile and dried at room temperature for 14 h.
  • 0.1 ml vaccine suspensions of the above Test mushrooms were inoculated in liquid malt agar in a petri dish and, after the agar had solidified, 0.1 ml was spatulated on the agar surface.
  • the test specimens impregnated with the test solutions were then placed sterile on the agar surface and the dishes were incubated at 25 ° C. for 7 days. The inhibitory effect was then evaluated according to the following scheme:
  • 0 clear zone of inhibition, indication of the zone of inhibition in mm
  • test was carried out in accordance with the guidelines for the testing and evaluation of chemical disinfection processes of the German Society for Hygiene and Microbiology (DGHM), Gustav Fischer Verlag, 1981: 16 pre-washed and autoclaved test specimens were placed in the above-mentioned vaccine pens of the test fungi and included Leave it to be turned over and over for 15 minutes. The test specimens contaminated in this way were then transferred to empty petri dishes and poured over each with 10 ml of the test solutions.
  • DGHM German Society for Hygiene and Microbiology
  • test specimens After 60 and 120 minutes of exposure time at 20 ° C, 2 of the test specimens were removed and briefly transferred to 10 ml of inactivator solution according to the DGHM guideline and inoculated therefrom onto CaSo (Candida) or malt agar plates (other test fungi). The incubation was carried out for 7 days at 25 ° C. Then the evaluation was qualitative, ie growth yes (+) or no (-).
  • IPBC show a very good fungistatic activity against both dermatophytes and fungi that produce mold stains or are harmful to the material.

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  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • Dentistry (AREA)
  • Biochemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract

L'invention concerne l'utilisation de 3-iodo-2-propinyl-carbamates comme principe actif antimicrobien, en particulier antimycose dans des agents de lavage, détergents, liquides lave-mains, liquides lave-vaisselle manuel, agents détergents pour lave-vaisselle machine et agents d'apprêtage pour textiles, peaux, fourrures ou cuirs.
EP01936157A 2000-04-04 2001-03-30 Utilisation de 3-iodo-2-propinyl-carbamates comme principe actif antimicrobien Withdrawn EP1268917A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10016371 2000-04-04
DE2000116371 DE10016371A1 (de) 2000-04-04 2000-04-04 Verwendung von 3-Iod-2-propinyl-carbamaten als antimikrobieller Wirkstoff
PCT/EP2001/003629 WO2001075213A1 (fr) 2000-04-04 2001-03-30 Utilisation de 3-iodo-2-propinyl-carbamates comme principe actif antimicrobien

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EP1268917A1 true EP1268917A1 (fr) 2003-01-02

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EP (1) EP1268917A1 (fr)
JP (1) JP2003535047A (fr)
AU (1) AU2001262148A1 (fr)
DE (1) DE10016371A1 (fr)
WO (1) WO2001075213A1 (fr)

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JP2010132612A (ja) * 2008-12-05 2010-06-17 Johnson Diversey Co Ltd 手指用殺菌洗浄剤組成物
JP2010132611A (ja) * 2008-12-05 2010-06-17 Johnson Diversey Co Ltd 手指用殺菌剤組成物

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WO2001075213A1 (fr) 2001-10-11
DE10016371A1 (de) 2001-10-18
JP2003535047A (ja) 2003-11-25

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