WO2001079405A1 - Use of n-octyl salicylic acid amide and/or n-decyl salicylic acid amide as antimicrobial active ingredient - Google Patents

Use of n-octyl salicylic acid amide and/or n-decyl salicylic acid amide as antimicrobial active ingredient Download PDF

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Publication number
WO2001079405A1
WO2001079405A1 PCT/EP2001/003692 EP0103692W WO0179405A1 WO 2001079405 A1 WO2001079405 A1 WO 2001079405A1 EP 0103692 W EP0103692 W EP 0103692W WO 0179405 A1 WO0179405 A1 WO 0179405A1
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WIPO (PCT)
Prior art keywords
acid amide
decylsalicylic
octylsalicylic
salicylic acid
test
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PCT/EP2001/003692
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German (de)
French (fr)
Inventor
Michael Heinzel
Hans Dolhaine
Regine Scholtyssek
Christine Schröder
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU62154/01A priority Critical patent/AU6215401A/en
Publication of WO2001079405A1 publication Critical patent/WO2001079405A1/en

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    • 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
    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/12—Nitrogen containing compounds organic derivatives of hydrazine
    • C04B24/124—Amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0058—Biocides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/521—Carboxylic amides (R1-CO-NR2R3), where R1, R2 and R3 are alkyl or alkenyl groups
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • 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
    • D06M13/415—Amides of aromatic carboxylic acids; Acylated aromatic amines
    • 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
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
    • C04B2103/60—Agents for protection against chemical, physical or biological attack
    • C04B2103/67—Biocides
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/00008—Obtaining or using nanotechnology related materials
    • 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

Definitions

  • N-octylsalicylic acid amide and / or N-decylsalicylic acid amide as an antimicrobial agent
  • the present invention relates to the use of N-octylsalicylic acid amide and / or N-decylsalicylic acid amide as an antimicrobial agent in detergents; Cleaning agents; Hand washing; Hand dishwashing detergents; Machine dishwashing detergents and agents for finishing textiles, furs, paper, skins or leather and in building materials, and agents and building materials containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
  • 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, due to use. Such germs are especially bacteria and 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.
  • N-octylsalicylic acid amide and N-Decylsacylic acid amide have antimicrobial activity in washing, cleaning and finishing agents and in building materials
  • the present invention therefore relates to the use of N-octylsaic acid amide and / or N-decylsalicyl acid amide as an antimicrobial, in particular antimycotic active ingredient in detergents, cleaning agents, hand detergents, hand dishwashing detergents, machine dishwashing detergents and agents for finishing textiles, fur, paper, archive materials, skins or furs
  • N-octylsaic acid amide and / or N-decylsalicyl acid amide as an antimicrobial, in particular antimycotic active ingredient in detergents, cleaning agents, hand detergents, hand dishwashing detergents, machine dishwashing detergents and agents for finishing textiles, fur, paper, archive materials, skins or furs
  • the compounds which can be used according to the invention are prepared by processes known per se from the prior art, in particular as described in EP-B-0 262 587, to which reference is hereby made in full
  • N-Octyl-sahcylsaureamid and N-Decyl-salicylsaureamid are prepared from Salicylsalemethylester and the corresponding amine by reacting methyl salicylate with n-octylamine and / or n-Decylamine according to known methods, which in the course of the amidation reaction The methanol formed is removed and the reaction products are purified in a manner known per se. It is possible to react methyl salicylate with one or both primary amines.
  • the respective amide When reacting with an amine, the respective amide is essentially obtained in one form, while when methyl salicylate is reacted with any mixture of the two n-alkylamines the two salicylic acid amides are formed in the ratio in which the n-alkylamines were used in the reaction. According to the invention, however, it is preferred that only one of the two n-alkylamines is used for amide formation in order to obtain the respective salicylic acid amides essentially in one form In a preferred export In the form of the production process for the two N-alkylsahcyl acid amides, the reaction is carried out at elevated temperature in order to accelerate it. The reaction temperatures are usually between 100 ° C. and 200 ° C. and are preferably set in a range from 130 ° C. to 170 ° C.
  • the reaction of the formation of the salicylic acid amides can be carried out in a solvent.
  • Aprotic organic solvents such as, for example, diethyl ether, are used as the solvent.
  • it is possible to carry out the amidation reaction in the absence of a solvent since both starting materials are liquid and without Allow others to react with one another under the specified reaction conditions.
  • the removal of the solvent for example by distillation, is saved as one operation.
  • the methanol formed in the course of the reaction is removed from the reaction mixture. This is done according to known methods.
  • the reaction product methanol is preferably distilled off and, in order to remove even the last methanol residues, a vacuum is applied and the temperature is raised to above 100 ° C., preferably above 130 ° C.
  • the reaction products formed are cleaned in a known manner. This is advantageously done by removing any unreacted amine, which is usually used in the reaction in equimolar amounts with the methyl salicylate, by washing with aqueous acid and then treating the reaction mixture with sodium bicarbonate solution, and the so obtained Crystals of the reaction products cleaned by recrystallization in a suitable solvent or solvent mixture.
  • Non-polar hydrocarbons or aprotic organic solvents are usually used as solvents; from the large class of these solvents, n-alkanes such as n-hexane or ethers such as diethyl ether are particularly suitable.
  • solvent mixtures for recrystallization as such, mixtures of methanol and water have proven themselves.
  • N-octyl- and N-decylsalicylic acid amides are formed in high yields in the process described: it is thus possible to obtain salicylic acid decylamide after recrystallization in a total yield of 75% of theory in pure form.
  • the starting material used in the process according to the invention is usually salicylic acid methyl ester from native sources: so-called “wintergreen oil”, which consists of over 99% of salicylic acid methyl ester, is outstandingly suitable as a starting material for the amidation reaction.
  • so-called “wintergreen oil” which consists of over 99% of salicylic acid methyl ester
  • N-octyl- and N-decylsalicylic acid amides which can be used according to the invention are added in a manner known to the person skilled in the art to the liquid agents in which they are to have their effect.
  • the N-octyl- and N-decyisalicylic acid ami- de 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 N-octyl- and N-decylsalicylic acid amides which can be used according to the invention are detergents; Cleaning agents; Hand washing; Hand dishwashing detergents; Machine dishwashing detergents and agents for finishing textiles, furs, paper, archival materials, skins or leather are added 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 N-octyl- and N-decylsalicylic acid amides which can be used according to the invention is about 5 to 500 nm, preferably 10 to 150 nm.
  • the term "nanoparticulate” is also used synonymously with the term “nanoscale”.
  • 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:
  • polyol and in particular polyglycene nests such as, for example, polyglycine polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycine 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 as well as 12-hydroxystearic acid and glycerin, polyglycene, pentaerythne, dipentaerythne, sugar alcohols (e.g. sorbitol), sucrose, alkyl glucosides (e.g. Methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycine mono- and diesters and sorbitan mono- and diesters of fatty acids or with castor oil are known, im Commercially available products are homologue mixtures whose average degree of alkoxyation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out corresponds to C 2 / i 8 fatty acid mono- and -these of adducts of ethylene oxide with Glycenn 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 having 8 to 18 carbon atoms.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products lies
  • anionic emulsifiers are soaps, Alkylbenzolsulfona- te, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, Glyce ⁇ nethersulfonate, ⁇ -methyl ester sulfonates Sulfofettsauren, alkyl sulfates, fatty alcohol ether sulfates, Glyce ⁇ nethersulfate, Hydroxymischethersulfate, Monoglyce ⁇ d (ether) sulfates, Fettsauream ⁇ d (ether) sulfates, mono- and dialkyl -sulfosuccinate, mono- and dialkylsulfosuccinamate, Sulfot ⁇ glyce ⁇ de, amide soaps, ether carboxylic acids and their salts, fatty acid icethionate, fatty acid sarcosinate, fatty acid tau ⁇ de
  • Zwitterionic surfactants are those surface-active compounds which carry 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 N-alkyl-N, N -d ⁇ methylammon ⁇ umglyc ⁇ nate, for example the T ⁇ methylammoniumgly- cinat, Kokosalkyldimethylammoniumglycinat, N-Acylam ⁇ no-propyl-N, N-dimethylammoniumglycinate, for example the Kokosacylaminopropyldimethylammonium-glycinate, and 2-alkyl-3-carboxylmethyl with 2-alkyl-3-carboxylmethyl C atoms in the alkyl or acyl group and cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • ampholytic surfactants sub ampholytic surfactants rule be understood to mean those surface active compounds which contain in addition to a C 8 ⁇ 8 alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltau ⁇ ne N-alkylsarcosines, 2- Alkylam ⁇ noprop ⁇ onsauren and alkylene laminoessigsauren containing around 8 to 18 carbon atoms in the alkyl group
  • particularly preferred ampholytic surfactants are N-cocoalkyl aminopropionate, cocoacylaminoethyl aminopropionate and C- ⁇ 2 / ⁇ - acylsarcosine
  • ampholytic emulsifiers are also quaternary , those of the ester quat type, preferably methyl-quaternized D fatty acid anolamine ester salts, particularly preferred are typical examples of anionic emulsifier
  • the active ingredients and the emulsifiers are in a weight ratio of 1 100 to 100 1, preferably 1 25 to 25 1 and in particular 1 10 to 10: 1 used.
  • Emulsifiers which are capable of forming microemulsions are particularly preferred.
  • Suitable protective colloids are e.g. Gelatin, casein, gum arabic, lysalbic acid, starch, carboxymethyl cellulose or modified carboxymethyl cellulose as well as polymers such as polyvinyl alcohols, polyvinyl pyrrolidones, polyalkylene glycols and polyacrylates.
  • N-octyl- and N-decylsalicylic acid amides 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
  • Evaporation technology offers another suitable method for producing the nanoscale particles.
  • the starting materials are first dissolved in a suitable organic solvent (for example alkanes, vegetable oils, ether esters, ketones, acetals and the like).
  • the solutions are then dissolved in water or another Non-solvent, usually in the presence of a surface-active compound dissolved therein, that the homogenization of the two immiscible solvents leads to precipitation of the nanoparticles, the organic solvent preferably evaporating.
  • a suitable organic solvent for example alkanes, vegetable oils, ether esters, ketones, acetals and the like.
  • the solutions are then dissolved in water or another Non-solvent, usually in the presence of a surface-active compound dissolved therein, that the homogenization of the two immiscible solvents leads to precipitation of the nanoparticles, the organic solvent preferably evaporating.
  • O / W Emulsions or O / W microemulsions can be used.
  • GAS process Gas Anti Solvent Recr ystallization
  • the process uses a highly compressed gas or supercritical fluid (e.g. carbon dioxide) as a non-solvent for the crystallization of dissolved substances.
  • the compressed gas phase is introduced into the primary solution of the starting materials and absorbed there, which increases the liquid volume, reduces the solubility and finely divided Particles are excreted
  • the PCA process (Precipitation with a Compressed Fluid Anti-Solvent) is similarly suitable.
  • the primary solution of the starting materials is introduced into a supercritical fluid, with finely divided droplets forming in which diffusion processes take place, so that the finest particles precipitate.
  • Processes (Particles from Gas Saturated Solutions) melt the raw materials by injecting 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 When expanding through a nozzle, cooling effects lead to the formation of very fine particles
  • gas e.g. carbon dioxide or propane
  • Another object of the present invention is the use of N-octylsalicyl acid amide and / or N-decylsalicyl acid amide as an antimicrobial, in particular as an antimycotic active ingredient in building materials, N-octylsahcyl- ⁇ aureamid and / or N-decylsalicyl acid amide being added to the building materials in the form of a Na-n-ion
  • the amides mentioned can be used in all building materials which have to be protected against fungal attack.
  • the building materials are particularly preferably selected from adhesives, sealants, fillers and paints, plastics, paints, paints, plaster, mortar, screed, concrete, insulating materials and Primers
  • the N-octyl- and N-decylsalicylic acid amides which can be used according to the invention are introduced into the liquid or solid building materials, as described above for the agents vary in a wide range depending on the conditions of use of the agents and building materials.
  • the concentration of the N-octyl and N-decylsalicylic acid amides which can be used according to the invention is preferably in the range from 0.01% to 5% by weight. in particular 0.1% by weight to 3% by weight and particularly preferably 0.1% by weight to 2% by weight
  • the present invention furthermore relates to detergents, cleaning agents, rinse aid, hand wash detergent, hand dishwashing detergent, machine dishwashing detergent and agent for finishing textiles, furs, paper, furs or leather which contain N-octylsalicylic acid amide and / or N-decylsalicylic acid amide, in particular those to which N-octylsalicyl acid amide and / or N-decylsalicyl acid amide has been added in the form of a nanodispersion
  • the present invention further relates to building materials, in particular adhesives, sealants, fillers and paints, plastics, paints, paints, plaster, mortar, screed, concrete, insulating materials and primers which contain N-octylsalicylic acid amide and / or N-decylsalicylic acid amide, especially those to which N-octylsalicylic acid amide and / or N-decylsalicylic acid amide has been added
  • textiles, furs, paper, archive materials, skins or leather equipped with an agent according to the invention.
  • the textiles, furs, skins or leather are finished in a manner known to the person skilled in the art, for example by immersing the paper or the textiles, furs, skins or leather in a suitably concentrated solution of an agent according to the invention.
  • test sample had the following composition:
  • Tagat S polyoxyethylene glycerol fatty acid ester
  • an antibacterial and antimycotic formulation was used, which comprised 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), T ⁇ chophyton mentagrophytes, ATCC 9533, (pre-breeding on malt agar , 8d / 25 ° C), Cladosponum cladosponoides, 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
  • 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 each of the above. Vaccine suspensions of the test mushrooms are placed and left in for 15 minutes with repeated turning. 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 an exposure time of 60 and 120 minutes at 20 ° C, 2 of the test specimens were removed and briefly transferred to 10 ml inactivator solution in accordance with the DGHM guideline and inoculated therefrom onto CaSo (Candida) or malt agar plates (other test fungi). The incubation was carried out at 25 ° C for 7 days. Growth yes (+) or no (-).
  • the N-octylsalicylic acid amide shows a very good fungistatic activity against both dermatophytes and fungi which produce mold stains or are harmful to the material
  • test sample (1) had the following composition
  • Tagat S polyoxyethylene glycenn fatty acid ester
  • test sample (2) A 10% aqueous dilution of the nanodispersed active substance preparation (1) was used as the test sample (2).
  • test sample (3) A 1% aqueous dispersion of an antibacterial and antimycotic nanodispersed reference preparation, which had the following composition, was used as test sample (3):
  • test sample (4) was bidest. Water used.
  • the inhibitory activity was tested in the agar hole test according to the following rule:
  • the substance to be tested is filled into a punched-out hole in an agar plate and diffuses into the agar which has been inoculated with a suitable or required test organism. If the test organism is inhibited by the substance, a visible zone of inhibition is created around the hole when the agar plate is subsequently incubated.
  • test organisms The choice of test organisms depends on the specific question. The organisms used in the present case are shown in Table 1.
  • Bacteria are inoculated in standard I nutrient broth and incubated at 37 ° C for 18-24 hours.
  • the overgrown culture is diluted 1 100 with standard I nutrient broth.
  • Mushrooms are pre-grown on root agar for 7 days at 30 ° C and the growth of a plate with 2 x 5 ml of root broth is washed away.
  • the washed-off material is filtered through glass wool and homogenized by rubbing in a glass stopper bottle with glass beads (the bottom is approximately covered with glass beads)
  • 1 ml of the test organism suspension is mixed into 200 ml of liquid standard I food agar (bacteria) or root agar (fungi) cooled to 45 ° C.
  • Agar plates are then poured immediately thereafter (approx. 20 ml agar per plate). After the agar has solidified, a 10 mm diameter hole is punched into the center of the plate using a sterile cork bur. The substance to be tested (or, depending on the aim of the experiment, dilutions of the substance) is filled into this hole. It must be ensured that the substance only gets into the hole and not on the agar surface.
  • test plate The plates are incubated at 37 ° C (bacteria) or 30 ° C (fungi) until a test plate with water instead of test substance gives the test organism good lawn growth
  • filter paper or tissue disks of defined sizes can be soaked in a solution of the test substance and placed on the inoculated agar - if a question requires it.
  • the size of the inhibition yards created is measured from the edge of the hole. If the entire plate is without growth, the test substance must be diluted more and tested again f. Result
  • the inhibition radius is given as the result for each test organism.
  • microbicidal activity was tested in accordance with EN 1040 (bactericidal) and EN 1275 (fungicidal), each with an expanded spectrum of test germs, which can be seen in Table 2.
  • the N-octylsalicylic acid amide shows a very good microbistatic and microbicidal activity against both bacteria and fungi.

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Abstract

The invention relates to the use of use of N-octyl salicylic acid amide and/or N-decyl salicylic acid amide as antimicrobial active ingredient in washing agents; detergents; hand detergents; hand dish washing detergents; machine dish washing detergents and agents for finishing textiles, furs, paper, skins or leather and in building materials. The invention also relates to agents and building materials containing N-octyl salicylic acid amide.

Description

Verwendung von N-Octylsalicylsäureamid und/oder N-Decyl- salicylsäureamid als antimikrobieller WirkstoffUse of N-octylsalicylic acid amide and / or N-decylsalicylic acid amide as an antimicrobial agent
Beschreibung:Description:
Die vorliegende Erfindung betrifft die Verwendung von N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid als antimikrobieller Wirkstoff in Waschmitteln; Reinigungsmitteln; Handwaschmitteln; Handgeschirrspülmitteln; Maschi- nengeschirrspülmitteln und Mitteln zur Ausrüstung von Textilien, Pelzen, Papier, Fellen oder Leder und in Baustoffen sowie Mittel und Baustoffe, die N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid enthalten.The present invention relates to the use of N-octylsalicylic acid amide and / or N-decylsalicylic acid amide as an antimicrobial agent in detergents; Cleaning agents; Hand washing; Hand dishwashing detergents; Machine dishwashing detergents and agents for finishing textiles, furs, paper, skins or leather and in building materials, and agents and building materials containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
Hygiene im Wasch- und Reinigungsprozeß bedeutet nicht nur die Beseitigung sichtbarer Verschmutzungen, sondern auch das Unschädlichmachen von Keimen, die gebrauchsbedingt das zu reinigende Gut, beispielsweise Wäsche, kontaminiert haben. Solche Keime sind insbesondere Bakterien und Pilze. Besondere Bedeutung hat die Hygiene, insbesondere die Wäschehygiene daher im gewerblichen Bereich, wo aus Krankenhäusern, Hotels, Gaststätten etc. Textilien wiederaufbereitet werden, die nicht innerhalb eines bestimmten Benutzerkreises zirkulieren, sondern von immer unterschiedlichen Verwendern gebraucht werden. Aber auch im Haushaltsbereich gewinnt der Hygieneaspekt immer größere Bedeutung, vor allem, weil immer mehr Textilien, die direkt auf dem Körper getragen werden, wie Unterwäsche, Dessous oder Strümpfe aus Geweben bestehen, die Waschtemperaturen von 40X oder darüber, Proteasen und bleichaktive Stoffe nicht tolerieren, so daß Feinwaschmittel verwendet werden müssen, deren keimtötende Wirkung nur gering ist.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, due to use. Such germs are especially bacteria and 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. But also in the household area, the hygiene aspect is becoming increasingly important, above all because more and more textiles that are worn directly on the body, such as underwear, lingerie or stockings made of fabrics, do not tolerate washing temperatures of 40X or above, proteases and bleach-active substances , so that mild detergents must be used whose germicidal effect is only slight.
Aus ökologischen Gründen - nicht zuletzt aufgrund der Selbstverpflichtung der Industrie zur Senkung des Energieverbrauchs - wurden die Waschverfahren in ihren hygienewirksamen Parametern (Temperatur, Waschzeiten und Flottenverhältnis) immer weiter minimiert. Im Ergebnis können alle diese Faktoren zusammen dazu fuhren, daß Keime, die beim Tragen die Wasche kontaminiert haben, im Waschprozeß nicht mehr ausreichend unschädlich gemacht werden und spater bei der Wiederverwendung zu hygienischen Problemen fuhren Außerdem können Wasch- und Spulmaschinen, vor allem solche, die längere Zeit nicht benutzt werden, durch starkes Keimwachstum in Schlauchen, der Pumpe oder der Einspulkammer ebenfalls zu hygienischen Problemen und zu olfaktoπschen Belästigungen fuhren Verbleibt Wasche über einen längeren Zeitraum feucht in der Waschmaschine, kann sie verpilzen - es kommt zu der bekannten Stockfleckenbildung Daruberhinaus ist Keimbefall, insbesondere Pilzbefall auch ein bekanntes Problem bei einer Vielzahl von Baustoffen sowohl wahrend der Lagerung, als auch nach der Verarbeitung und AnwendungFor ecological reasons - not least because of the voluntary commitment of the industry to reduce energy consumption - the washing processes in their hygienically effective parameters (temperature, washing times and liquor ratio) were continuously minimized. As a result, all of these factors together can lead to the fact that germs which have contaminated the wash when worn are no longer rendered harmless in the washing process and later lead to hygienic problems when reused. Washing machines and dishwashers, especially those which not used for a long time, due to strong germ growth in hoses, the pump or the induction chamber also lead to hygienic problems and to olfactory annoyances. If laundry remains damp in the washing machine for a longer period of time, it can fungal - this leads to the well-known formation of mold stains , in particular fungal infestation, is also a known problem with a large number of building materials, both during storage and after processing and application
Aus der EP-B-0 262 587 sind N-Octylsalicylsaureamid und N-Decylsalicylsaure- amid sowie deren Verwendung als antibakterielle Mittel, insbesondere in Mund- und Zahnpflegemitteln und in Korperdeodorantien bekanntFrom EP-B-0 262 587 N-octylsalicyl acid amide and N-decylsalicyl acid amide and their use as antibacterial agents, in particular in oral and dental care products and in body deodorants, are known
Der vorliegenden Erfindung liegt die Aufgabe zugrunde, neue Wasch-, Reini- gungs- und Ausrustungsmittel Mittel bereitzustellen, die eine antimikrobielle Wirkung aufweisen Eine weitere Aufgabe der vorliegenden Erfindung ist es, Baustoffe bereitzustellen, die widerstandsfähig gegenüber Keimbefall sindThe object of the present invention is to provide new washing, cleaning and finishing agents which have an antimicrobial activity. Another object of the present invention is to provide building materials which are resistant to germ attack
Es wurde gefunden, daß N-Octylsalicylsaureamid und N-Decylsa cylsaureamid in Wasch-, Reinigungs- und Ausrustungsmitteln sowie in Baustoffen antimikrobielle Wirksamkeit aufweisenIt has been found that N-octylsalicylic acid amide and N-Decylsacylic acid amide have antimicrobial activity in washing, cleaning and finishing agents and in building materials
Gegenstand der vorliegenden Erfindung ist daher die Verwendung von N- Octylsa cylsaureamid und/oder N-Decylsalicylsaureamid als antimikrobieller, insbesondere antimycotischer Wirkstoff in Waschmitteln, Reinigungsmitteln, Handwaschmitteln, Handgeschirrspulmitteln, Maschinengeschirrspulmitteln und Mitteln zur Ausrüstung von Textilien Pelzen, Papier, Archivmatenalien, Fellen oder Leder Die erfindungsgemaß verwendbaren Verbindungen werden nach an sich aus dem Stand der Technik bekannten Verfahren hergestellt, insbesondere, wie in der EP-B-0 262 587 beschrieben, auf die hiermit in vollem Umfang Bezug genommen wirdThe present invention therefore relates to the use of N-octylsaic acid amide and / or N-decylsalicyl acid amide as an antimicrobial, in particular antimycotic active ingredient in detergents, cleaning agents, hand detergents, hand dishwashing detergents, machine dishwashing detergents and agents for finishing textiles, fur, paper, archive materials, skins or furs The compounds which can be used according to the invention are prepared by processes known per se from the prior art, in particular as described in EP-B-0 262 587, to which reference is hereby made in full
N-Octyl-sahcylsaureamid und N-Decyl-salicylsaureamid werden aus Salicylsau- remethylester und dem entsprechendem Amin dadurch hergestellt, daß man nach an sich bekannten Methoden Salicylsauremethylester mit n-Octylamin und/oder n-Decylamin umsetzt, das im Zuge der Amidierungs-Reaktion gebildete Methanol entfernt und die Reaktionsprodukte in an sich bekannter Weise reinigt Es ist möglich, Salicylsauremethylester mit einem oder beiden primären Ammen umzusetzen Bei Umsetzung mit einem Amin wird das jeweilige Amid im wesentlichen in einer Form erhalten, wahrend bei Umsetzung von Salicylsauremethylester mit einer beliebigen Mischung beider n-Alkylamine die beiden Salicylsaureamide in dem Mengenverhältnis entstehen in dem die n-Alkylamine in die Reaktion eingesetzt wurden Erfindungsgemaß ist es jedoch bevorzugt, daß zur Amidbildung nur eines der beiden n-Alkylamine eingesetzt wird um die jeweiligen Salicylsaureamide im wesentlichen in einer Form zu erhalten In einer bevorzugten Ausfuhrungsform des Herstellungsverfahrens der beiden N-Alkylsahcylsaureamide wird die Reaktion bei erhöhter Temperatur durchgeführt, um sie zu beschleunigen Die Reaktionstemperaturen hegen üblicherweise zwischen 100 °C und 200 °C und werden bevorzugt auf einen Bereich von 130 °C bis 170 °C eingestelltN-Octyl-sahcylsaureamid and N-Decyl-salicylsaureamid are prepared from Salicylsalemethylester and the corresponding amine by reacting methyl salicylate with n-octylamine and / or n-Decylamine according to known methods, which in the course of the amidation reaction The methanol formed is removed and the reaction products are purified in a manner known per se. It is possible to react methyl salicylate with one or both primary amines. When reacting with an amine, the respective amide is essentially obtained in one form, while when methyl salicylate is reacted with any mixture of the two n-alkylamines the two salicylic acid amides are formed in the ratio in which the n-alkylamines were used in the reaction. According to the invention, however, it is preferred that only one of the two n-alkylamines is used for amide formation in order to obtain the respective salicylic acid amides essentially in one form In a preferred export In the form of the production process for the two N-alkylsahcyl acid amides, the reaction is carried out at elevated temperature in order to accelerate it. The reaction temperatures are usually between 100 ° C. and 200 ° C. and are preferably set in a range from 130 ° C. to 170 ° C.
Die Reaktion der Bildung der Salicylsaureamide kann in einem Losungsmittel durchgeführt werden Als Losungsmittel werden aprotische organische Losungsmittel, wie beispielsweise Diethylether verwendet In einer bevorzugten Ausfuhrungsform der Reaktion ist es jedoch möglich, die Amidierungsreaktion in Abwesenheit eines Losungsmittels durchzufuhren, da beide Ausgangsstoffe flussig sind und sich ohne weiteres unter den angegebenen Reaktionsbedingungen miteinander zur Reaktion bringen lassen In diesem Fall wird das Entfernen des Losungsmitteis, beispielsweise durch Abdestillieren, als Arbeitsgang gespart In einem der eigentlichen Amidbildung nachgelagerten Reaktionsschritt wird das im Verlauf der Reaktion gebildete Methanol aus der Reaktionsmischung entfernt. Dies geschieht nach bekannten Methoden. Bevorzugt wird das Reaktionsprodukt Methanol abdestilliert und dabei - zur Entfernung auch letzter Methanolreste - Vakuum angelegt und die Temperatur auf über 100 °C, bevorzugt über 130 °C, angehoben. Die entstandenen Reaktionsprodukte werden auf bekannte Weise gereinigt. Dies geschieht in vorteilhafter Weise dadurch, daß man eventuell nicht umgesetztes Amin, das in die Reaktion üblicherweise in ä- quimolaren Mengen mit dem Salicylsauremethylester eingesetzt wird, durch Auswaschen mit wäßriger Säure und anschließendes Behandeln der Reaktionsmischung mit Natriumhydrogencarbonat-Lösung entfernt, und die so erhaltenen Kristalle der Reaktionsprodukte durch Umkristallisieren in einem geeigneten Lösungsmittel bzw. Lösungsmittelgemisch reinigt. Als Lösungsmittel werden üblicherweise unpolare Kohlenwasserstoffe oder aprotische organische Lösungsmittel verwendet; aus der großen Klasse dieser Lösungsmittel sind n- Alkane wie n-Hexan oder Ether wie Diethylether besonders gut geeignet. Es ist jedoch auch möglich, Lösungsmittelgemische zur Umkristallisation zu verwenden; als solche haben sich beispielsweise Mischungen von Methanol und Wasser bewährt.The reaction of the formation of the salicylic acid amides can be carried out in a solvent. Aprotic organic solvents, such as, for example, diethyl ether, are used as the solvent. In a preferred embodiment of the reaction, however, it is possible to carry out the amidation reaction in the absence of a solvent, since both starting materials are liquid and without Allow others to react with one another under the specified reaction conditions. In this case, the removal of the solvent, for example by distillation, is saved as one operation. In a reaction step downstream of the actual amide formation the methanol formed in the course of the reaction is removed from the reaction mixture. This is done according to known methods. The reaction product methanol is preferably distilled off and, in order to remove even the last methanol residues, a vacuum is applied and the temperature is raised to above 100 ° C., preferably above 130 ° C. The reaction products formed are cleaned in a known manner. This is advantageously done by removing any unreacted amine, which is usually used in the reaction in equimolar amounts with the methyl salicylate, by washing with aqueous acid and then treating the reaction mixture with sodium bicarbonate solution, and the so obtained Crystals of the reaction products cleaned by recrystallization in a suitable solvent or solvent mixture. Non-polar hydrocarbons or aprotic organic solvents are usually used as solvents; from the large class of these solvents, n-alkanes such as n-hexane or ethers such as diethyl ether are particularly suitable. However, it is also possible to use solvent mixtures for recrystallization; as such, mixtures of methanol and water have proven themselves.
Die N-Octyl- und N-Decylsalicylsäureamide entstehen bei dem beschriebenen Verfahren in hohen Ausbeuten: so ist es möglich, Salicylsäuredecylamid nach dem Umkristallisieren in einer Gesamtausbeute von 75 % der Theorie in reiner Form zu erhalten.The N-octyl- and N-decylsalicylic acid amides are formed in high yields in the process described: it is thus possible to obtain salicylic acid decylamide after recrystallization in a total yield of 75% of theory in pure form.
Als Ausgangsstoff wird in das erfindungsgemäße Verfahren üblicherweise Salicylsauremethylester aus nativen Quellen eingesetzt: sogenanntes „Wintergrün- öl", das zu über 99 % aus Salicylsauremethylester besteht, ist als Edukt für die Arnidierungsreaktion in hervorragender Weise geeignet. Es ist jedoch auch möglich, Salicylsauremethylester synthetischen Ursprungs zu verwenden.The starting material used in the process according to the invention is usually salicylic acid methyl ester from native sources: so-called “wintergreen oil”, which consists of over 99% of salicylic acid methyl ester, is outstandingly suitable as a starting material for the amidation reaction. However, it is also possible to use salicylic acid methyl ester of synthetic origin to use.
Die erfindungsgemäß verwendbaren N-Octyl- und N-Decylsalicylsäureamide werden in dem Fachmann bekannter Weise den flüssigen Mitteln, in denen sie ihre Wirkung entfalten sollen, zugesetzt. Zur Verwendung in festen Mitteln können die erfindungsgemäß verwendbaren N-Octyl- und N-Decyisalicylsäureami- de entweder den flüssigen oder pastösen Grundstoffen zugesetzt werden, aus denen man die festen Mittel herstellt, oder auf die festen Mittel aufgebracht werden, beispielsweise durch Sprühen.The N-octyl- and N-decylsalicylic acid amides which can be used according to the invention are added in a manner known to the person skilled in the art to the liquid agents in which they are to have their effect. For use in solid agents, the N-octyl- and N-decyisalicylic acid ami- de 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.
In einer nicht einschränkenden Ausführungsform der vorliegenden Erfindung werden die erfindungsgemäß verwendbaren N-Octyl- und N-Decylsalicylsäureamide den Waschmitteln; Reinigungsmitteln; Handwaschmitteln; Handgeschirrspülmitteln; Maschinengeschirrspülmitteln und Mitteln zur Ausrüstung von Textilien, Pelzen, Papier, Archivmaterialien, Fellen oder Leder in nanoskaliger Form zugesetzt.In a non-limiting embodiment of the present invention, the N-octyl- and N-decylsalicylic acid amides which can be used according to the invention are detergents; Cleaning agents; Hand washing; Hand dishwashing detergents; Machine dishwashing detergents and agents for finishing textiles, furs, paper, archival materials, skins or leather are added in nanoscale form.
Unter nanoskaligen Stoffen sind Stoffe zu verstehen, deren Teilchendurchmesser in der Richtung der größten Ausdehnung der Teilchen weniger als 1000 nm (Nanometer) beträgt. Insbesondere beträgt der Teilchendurchmesser der erfindungsgemäß verwendbaren N-Octyl- und N-Decylsalicylsäureamide etwa 5 bis 500 nm, bevorzugt 10 bis 150 nm In der vorliegenden Schrift wird synonym zu dem Begriff "nanoskalig" auch der Begriff "nanopartikulär" benutzt. Die erfindungsgemäß verwendbaren nanoskaligen Wirkstoffe bestehen aus einer diskreten Phase des Wirkstoffs, an dessen Oberfläche vorzugsweise mindestens ein oberflächenmodifizierender Stoff adsorbiert ist. Als oberflächenmodifizierende Stoffe besonders geeignet sind Emulgatoren und/oder Schutzkolloide. Die Ummantelung der Partikel mit Emulgatoren und/oder Schutzkolloiden führt dazu, daß eine nachträgliche Agglomeration der Partikel nicht stattfindet.Nanoscale substances are substances whose particle diameter in the direction of the greatest expansion of the particles is less than 1000 nm (nanometers). In particular, the particle diameter of the N-octyl- and N-decylsalicylic acid amides which can be used according to the invention is about 5 to 500 nm, preferably 10 to 150 nm. In the present document, the term "nanoparticulate" is also used synonymously with the term "nanoscale". 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.
Als Emulgatoren kommen beispielsweise nichtionogene Tenside aus mindestens einer der folgenden Gruppen in Frage:Examples of suitable emulsifiers are nonionic surfactants from at least one of the following groups:
(1) Anlagerungsprodukte von 2 bis 30 Mol Ethylenoxid und/ oder 0 bis 5 Mol Propylenoxid an lineare Fettalkohole mit 8 bis 22 C-Atomen, an Fettsäuren mit 12 bis 22 C-Atomen und an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe;(1) Adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols with 8 to 15 C atoms in the alkyl group;
(2) C12/ι8-Fettsäuremono- und -diester von Anlagerungsprodukten von 1 bis 30 Mol Ethylenoxid an Glyceπn; (3) Glyceπnmono- und -diester und Sorbitanmono- und -diester von gesattigten und ungesättigten Fettsauren mit 6 bis 22 Kohlenstoffatomen und deren Ethylenoxidanlagerungsprodukte,(2) C 12 / ι 8 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with Glyceπn; (3) Glycine mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids with 6 to 22 carbon atoms and their ethylene oxide addition products,
(4) Alkylmono- und -oligoglycoside mit 8 bis 22 Kohlenstoffatomen im Alkyl- rest und deren ethoxylierte Analoga,(4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs,
(5) Anlagerungsprodukte von 15 bis 60 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl;(5) adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil;
(6) Polyol- und insbesondere Polyglycennester, wie z B Polyglycennpolyri- cinoleat, Polyglycerιnpoly-12-hydroxystearat oder Polyglyceπndimerat. Ebenfalls geeignet sind Gemische von Verbindungen aus mehreren dieser Substanzklassen;(6) polyol and in particular polyglycene nests, such as, for example, polyglycine polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycine dimerate. Mixtures of compounds from several of these classes of substances are also suitable;
(7) Anlagerungsprodukte von 2 bis 15 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl;(7) adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil;
(8) Partialester auf Basis linearer, verzweigter, ungesättigter bzw. gesättigter C6/22-Fettsauren, Ricinolsäure sowie 12-Hydroxystearιnsaure und Glyce- rin, Polyglycenn, Pentaerythnt, Dipenta-erythnt, Zuckeralkohole (z.B. Sorbit), Sucrose, Alkylglucoside (z.B Methylglucosid, Butylglucosid, Lau- ryl-glucosid) sowie Polyglucoside (z B. Cellulose);(8) partial esters based on linear, branched, unsaturated or saturated C 6/22 fatty acids, ricinoleic acid as well as 12-hydroxystearic acid and glycerin, polyglycene, pentaerythne, dipentaerythne, sugar alcohols (e.g. sorbitol), sucrose, alkyl glucosides (e.g. Methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (eg cellulose);
(9) Mono-, Di- und Trialkylphosphate sowie Mono-, Di- und/oder Tri-PEG- alkylphosphate und deren Salze;(9) mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and their salts;
(10) Wollwachsalkohole,(10) wool wax alcohols,
(11) Polysiloxan-Polyalkyl-Polyether-Copolymere bzw entsprechende Derivate;(11) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;
(12) Mischester aus Pentaerythnt, Fettsauren, Citronensaure und Fettalkohol gemäß DE-PS 1165574 und/oder Mischester von Fettsauren mit 6 bis 22 Kohlenstoffatomen, Methylglucose und Polyolen, vorzugsweise Glycerin oder Polyglycenn sowie(12) mixed esters of pentaerythn, fatty acids, citric acid and fatty alcohol according to DE-PS 1165574 and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycine and
(13) Polyalkylenglycole(13) Polyalkylene glycols
Die Anlagerungsprodukte von Ethylenoxid und/oder von Propylenoxid an Fettalkohole, Fettsauren, Alkylphenole, Glyceπnmono- und -diester sowie Sorbitanmono- und -diester von Fettsäuren oder an Ricinusöl stellen bekannte, im Handel erhältliche Produkte dar Es handelt sich dabei um Homologen-gemi- sche, deren mittlerer Alkoxy erungsgrad dem Verhältnis der Stoffmengen von Ethylenoxid und/ oder Propylenoxid und Substrat, mit denen die Anlagerungs- reaktion durchgeführt wird entspricht Cι2/i8-Fettsauremono- und -diester von Anlagerungsprodukten von Ethylenoxid an Glycenn sind aus der DE-PS 2024051 als Ruckfettungsmittel für kosmetische Zubereitungen bekanntThe adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycine mono- and diesters and sorbitan mono- and diesters of fatty acids or with castor oil are known, im Commercially available products are homologue mixtures whose average degree of alkoxyation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out corresponds to C 2 / i 8 fatty acid mono- and -these of adducts of ethylene oxide with Glycenn are known from DE-PS 2024051 as refatting agents for cosmetic preparations
C8/i8-Alkylmono- und -oligoglycoside, ihre Herstellung und ihre Verwendung sind aus dem Stand der Technik bekannt Ihre Herstellung erfolgt insbesondere durch Umsetzung von Glucose oder Oligosacchaπden mit primären Alkoholen mit 8 bis 18 C-Atomen Bezüglich des Glycosidrestes gilt, daß sowohl Monogly- coside, bei denen ein cychscher Zuckerrest glycosidisch an den Fettalkohol gebunden ist, als auch o gomere Glycoside mit einem Oligomensationsgrad bis vorzugsweise etwa 8 geeignet sind Der Oligomeπsierungsgrad ist dabei ein statistischer Mittelwert, dem eine für solche technischen Produkte übliche Ho- mologenverteilung zugrunde liegtC 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 having 8 to 18 carbon atoms. The following applies to the glycoside radical: Both monoglycosides, in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol, and also oomeric glycosides with a degree of oligomerization of up to preferably 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 lies
Typische Beispiele für anionische Emulgatoren sind Seifen, Alkylbenzolsulfona- te, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glyceπnethersulfonate, α-Methylestersulfonate, Sulfofettsauren, Alkylsulfate, Fettalkoholethersulfate, Glyceπnethersulfate, Hydroxymischethersulfate, Monoglyceπd(ether)sulfate, Fettsaureamιd(ether)sulfate, Mono- und Dialkyl-sulfosuccinate, Mono- und Dial- kylsulfo-succinamate, Sulfotπglyceπde, Amidseifen, Ethercarbonsauren und deren Salze, Fettsaureisethionate, Fettsauresarcosinate, Fettsauretauπde, N- Acylamiπosauren wie beispielsweise Acyllactylate, Acyltartrate, Acylglutamate und Acylaspartate, Alkyloligoglucosidsulfate, Proteinfettsaurekondensate (ins- be-sondere pflanzliche Produkte auf Weizenbasis) und Alkyl(ether)phosphate Sofern die anionischen Ten-side Polyglycoletherketten enthalten, können diese eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenvertei- lung aufweisen Weiterhin können als Emulgatoren zwitterionische Tenside eingesetzt werden Als zwitterionische Tenside werden solche oberflächenaktiven Verbindungen bezeichnet, die im Molekül mindestens eine quartare Ammoniumgruppe und mindestens eine Carboxylat- und eine Sulfonatgruppe tragen Besonders geeignete zwitterionische Tenside sind die sogenannten Betaine wie die N-Alkyl- N,N-dιmethylammonιumglycιnate, beispielsweise das Tπmethylammoniumgly- cinat, Kokosalkyldimethylammoniumglycinat, N-Acylamιno-propyl-N,N- dimethylammoniumglycinate, beispielsweise das Kokosacylaminopropyldi- methylammonium-glycinat, und 2-Alkyl-3-carboxylmethyl-3-hydroxyethylιmιda- zoline mit jeweils 8 bis 18 C-Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhydroxyethylcarboxymethylglycinat Besonders bevorzugt ist das unter der CTFA-Bezeichnung Cocamidopropyl Betaine bekannte Fett- saureamid-DeπvatTypical examples of anionic emulsifiers are soaps, Alkylbenzolsulfona- te, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, Glyceπnethersulfonate, α-methyl ester sulfonates Sulfofettsauren, alkyl sulfates, fatty alcohol ether sulfates, Glyceπnethersulfate, Hydroxymischethersulfate, Monoglyceπd (ether) sulfates, Fettsaureamιd (ether) sulfates, mono- and dialkyl -sulfosuccinate, mono- and dialkylsulfosuccinamate, Sulfotπglyceπde, amide soaps, ether carboxylic acids and their salts, fatty acid icethionate, fatty acid sarcosinate, fatty acid tauπde, N-acylamino acid such as acyl lactylate, acylglutarate methate, acylglutarate sulfate, acylglutarate sulfate, acylglutarate sulfate, acylglutarate methacrylate, acylglutarate methacrylate, acylglutarate fatty acid, acylglutarate methacrylate, acylglutarate methacrylate, acyl glucosate fate Wheat-based products) and alkyl (ether) phosphates If the anionic ten-side contains polyglycol ether chains, these can have a conventional, but preferably a narrow, homolog distribution Furthermore, zwitterionic surfactants can be used as emulsifiers. Zwitterionic surfactants are those surface-active compounds which carry 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 N-alkyl-N, N -dιmethylammonιumglycιnate, for example the Tπmethylammoniumgly- cinat, Kokosalkyldimethylammoniumglycinat, N-Acylamιno-propyl-N, N-dimethylammoniumglycinate, for example the Kokosacylaminopropyldimethylammonium-glycinate, and 2-alkyl-3-carboxylmethyl with 2-alkyl-3-carboxylmethyl C atoms in the alkyl or acyl group and cocoacylaminoethylhydroxyethylcarboxymethylglycinate. The fatty acid amide derivative known under the CTFA name of Cocamidopropyl Betaine is particularly preferred
Ebenfalls geeignete Emulgatoren sind ampholytische Tenside Unter ampholyti- schen Tensiden werden solche oberflächenaktiven Verbindungen verstanden, die außer einer C8 ι8-Alkyl- oder -Acylgruppe im Molekül mindestens eine freie Aminogruppe und mindestens eine -COOH- oder -SO3H-Gruppe enthalten und zur Ausbildung innerer Salze befähigt sind Beispiele für geeignete ampholytische Tenside sind N-Alkylglycine, N-Alkylpropionsauren, N-Alkylaminobutter- sauren, N-Alkyliminodipropionsauren, N-Hydroxyethyl-N-alkylamidopropylg- lycine, N-Alkyltauπne N-Alkylsarcosine, 2-Alkylamιnopropιonsauren und Alky- laminoessigsauren mit jeweils etwa 8 bis 18 C-Atomen in der Alkylgruppe Besonders bevorzugte ampholytische Tenside sind das N-Kokosalkyl- aminopropionat, das Kokosacylaminoethylaminopropionat und das C-ι2/ιβ- Acylsarcosin Neben den ampholytischen kommen auch quartare Emulgatoren in Betracht, wobei solche vom Typ der Esterquats, vorzugsweise methyl- quaternierte D fettsauretπethanolaminester-Salze, besonders bevorzugt sind Typische Beispiele für anionische Emulgatoren sind Alkylsulfate, Alkylethersul- fate und Monoglycerιd(ether)sulfateLikewise suitable emulsifiers are ampholytic surfactants sub ampholytic surfactants rule be understood to mean those surface active compounds which contain in addition to a C 8 ι 8 alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltauπne N-alkylsarcosines, 2- Alkylamιnopropιonsauren and alkylene laminoessigsauren containing around 8 to 18 carbon atoms in the alkyl group particularly preferred ampholytic surfactants are N-cocoalkyl aminopropionate, cocoacylaminoethyl aminopropionate and C-ι 2 / ιβ- acylsarcosine Besides ampholytic emulsifiers are also quaternary , those of the ester quat type, preferably methyl-quaternized D fatty acid anolamine ester salts, particularly preferred are typical examples of anionic emulsifiers are alkyl sulfates, alkyl ether sulfates and monoglyceride (ether) sulfates
In der Regel werden die Wirkstoffe und die Emulgatoren im Gewichtsverhaltnis 1 100 bis 100 1 , vorzugsweise 1 25 bis 25 1 und insbesondere 1 10 bis 10 : 1 eingesetzt. Besonders bevorzugt sind solche Emulgatoren, welche zur Ausbildung von Mikroemulsionen befähigt sind.As a rule, the active ingredients and the emulsifiers are in a weight ratio of 1 100 to 100 1, preferably 1 25 to 25 1 and in particular 1 10 to 10: 1 used. Emulsifiers which are capable of forming microemulsions are particularly preferred.
Geeignete Schutzkolloide sind z.B. Gelatine, Casein, Gummi arabicum, Lysal- binsäure, Stärke, Carboxymethylcellulose oder modifizierte Carboxymethylcel- lulose sowie Polymere, wie etwa Polyvinylalkohole, Polyvinylpyrrolidone, Poly- alkylenglycoie und Polyacrylate.Suitable protective colloids are e.g. Gelatin, casein, gum arabic, lysalbic acid, starch, carboxymethyl cellulose or modified carboxymethyl cellulose as well as polymers such as polyvinyl alcohols, polyvinyl pyrrolidones, polyalkylene glycols and polyacrylates.
Die erfindungsgemäß verwendbaren N-Octyl- und N-Decylsalicylsäureamide können auch als Nanopartikel eingesetzt werden, die von einem oder mehreren Emulgatoren und/oder Schutzkolloiden ummantelt sind.The N-octyl- and N-decylsalicylic acid amides 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.
Entsprechende Nanopartikel können beispielsweise hergestellt werden, indem manCorresponding nanoparticles can be produced, for example, by
(a) N-Octyl- und N-Decylsalicylsäureamide in eine flüssige Phase, in der sie nicht löslich sind, einbringt,(a) introducing N-octyl- and N-decylsalicylic acid amides into a liquid phase in which they are not soluble,
(b) die resultierende Mischung über den Schmelzpunkt der N-Octyl- und N- Decylsalicylsäureamide erwärmt,(b) the resulting mixture is heated above the melting point of the N-octyl and N-decylsalicylic acid amides,
(c) der resultierenden Ölphase eine wirksame Menge mindestens eines Emul- gators zusetzt und schließlich(c) adding an effective amount of at least one emulsifier to the resulting oil phase and finally
(d) die Emulsion unter den Schmelzpunkt der N-Octyl- und N- Decylsalicylsäureamide abkühlt.(d) the emulsion cools below the melting point of the N-octyl and N-decylsalicylic acid amides.
Ein weiteres Verfahren zur Herstellung von Nanopartikeln durch rasche Entspannung von überkritischen Lösungen (Rapid Expansion of Supercritical Solutions RESS) ist beispielsweise aus dem Aufsatz von S.Chihiar, M.Türk und K.Schaber in Proceedings World Congress on Particle Technology 3, Brighton, 1998 bekannt. Um zu verhindern, daß die Nanopartikel wieder zusammenbacken, empfiehlt es sich, die Ausgangsstoffe in Gegenwart geeigneter Schutzkolloide oder Emulgatoren zu lösen und/oder die kritischen Lösungen in wäßrige und/oder alkoholische Lösungen der Schutzkolloide bzw. Emulgatoren oder aber in kosmetische Ole zu entspannen welche ihrerseits wieder geloste Emulgatoren und/oder Schutzkolloide enthalten könnenAnother method for the production of nanoparticles by rapid relaxation of supercritical solutions (RESS) is, for example, from the article by S.Chihiar, M.Türk and K. Schaber in Proceedings World Congress on Particle Technology 3, Brighton, 1998 known. To prevent the nanoparticles from caking again, it is advisable to dissolve the starting materials in the presence of suitable protective colloids or emulsifiers and / or to dissolve the critical solutions in aqueous and / or alcoholic solutions of the protective colloids or emulsifiers or but to relax in cosmetic oils which in turn can contain dissolved emulsifiers and / or protective colloids
Ein weiteres geeignetes Verfahren zur Herstellung der nanoskaligen Partikel bietet die Evaporationstechnik Hierbei werden die Ausgangsstoffe zunächst in einem geeigneten organischen Losungsmittel (z B Alkane, pflanzliche Ole, Ether Ester, Ketone, Acetale und dergleichen) gelost Anschließend werden die Losungen derart in Wasser oder einem anderen Nicht-Losungsmittel, in der Regel in Gegenwart einer darin gelosten oberflächenaktiven Verbindung gegeben, daß es durch die Homogenisierung der beiden nicht miteinander mischbaren Losungsmittel zu einer Ausfallung der Nanopartikel kommt, wobei das organische Losungsmittel vorzugsweise verdampft Anstelle einer wäßrigen Losung können auch O/W-Emulsionen bzw O/W-Mikroemulsionen eingesetzt werden Als oberflächenaktive Verbindungen können die bereits eingangs erläuterten Emulgatoren und Schutzkolloide verwendet werden Eine weitere Möglichkeit zur Herstellung von Nanopartikeln besteht in dem sogenannten GAS-Verfahren (Gas Anti Solvent Recrystallization) Das Verfahren nutzt ein hochkomprimiertes Gas oder überkritisches Fluid (z B Kohlendioxid) als Nicht- Losungsmittel zur Kristallisation von gelosten Stoffen Die verdichtete Gasphase wird in die Pπmarlosung der Ausgangsstoffe eingeleitet und dort absorbiert, wodurch sich das Flussigkeitsvolumen vergrößert die Los chkeit abnimmt und feinteilige Partikel ausgeschieden werdenEvaporation technology offers another suitable method for producing the nanoscale particles. Here, the starting materials are first dissolved in a suitable organic solvent (for example alkanes, vegetable oils, ether esters, ketones, acetals and the like). The solutions are then dissolved in water or another Non-solvent, usually in the presence of a surface-active compound dissolved therein, that the homogenization of the two immiscible solvents leads to precipitation of the nanoparticles, the organic solvent preferably evaporating. Instead of an aqueous solution, O / W Emulsions or O / W microemulsions can be used. The emulsifiers and protective colloids already explained at the beginning can be used as surface-active compounds. Another possibility for producing nanoparticles is the so-called GAS process (Gas Anti Solvent Recr ystallization) The process uses a highly compressed gas or supercritical fluid (e.g. carbon dioxide) as a non-solvent for the crystallization of dissolved substances. The compressed gas phase is introduced into the primary solution of the starting materials and absorbed there, which increases the liquid volume, reduces the solubility and finely divided Particles are excreted
Ähnlich geeignet ist das PCA-Verfahren (Precipitation with a Compressed Fluid Anti-Solvent) Hier wird die Pπmarlosung der Ausgangsstoffe in ein überkritisches Fluid eingeleitet, wobei sich feinstverteilte Tropfchen bilden, in denen Diffusionsvorgange ablaufen, so daß eine Ausfallung feinster Partikel erfolgt Beim PGSS-Verfahren (Particles from Gas Saturated Solutions) werden die Ausgangsstoffe durch Aufpressen von Gas (z B Kohlendioxid oder Propan) aufgeschmolzen Druck und Temperatur erreichen nahe- oder überkritische Bedingungen Die Gasphase lost sich im Feststoff und bewirkt eine Absenkung der Schmelztemperatur, der Viskosität und der Oberflachenspannung Bei der Expansion durch eine Düse kommt es durch Abkuhlungseffekte zur Bildung feinster Teilchen Die aufgeführten Herstellverfahren für die erfindungsgemaßen Nanopartikel sind lediglich beispielhaft zu verstehen und stellen keine Einschränkung darThe PCA process (Precipitation with a Compressed Fluid Anti-Solvent) is similarly suitable. Here, the primary solution of the starting materials is introduced into a supercritical fluid, with finely divided droplets forming in which diffusion processes take place, so that the finest particles precipitate. Processes (Particles from Gas Saturated Solutions) melt the raw materials by injecting 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 When expanding through a nozzle, cooling effects lead to the formation of very fine particles The production processes listed for the nanoparticles according to the invention are only to be understood as examples and do not constitute any restriction
Ein weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung von N- Octylsalicylsaureamid und/oder N-Decylsalicylsaureamid als antimikrobieller, insbesondere als antimycotischer Wirkstoff in Baustoffen, wobei N-Octylsahcyl- εaureamid und/oder N-Decylsalicylsaureamid den Baustoffen in Form einer Na- nodispersion zugesetzt werden können Verwendbar sind die genannten Amide in allen Baustoffen, die gegen Pilzbefall geschützt werden müssen Besonders bevorzugt sind die Baustoffe ausgewählt unter Klebe-, Dichtungs-, Spachtel- und Anstrichmassen, Kunststoffen Lacken, Farben, Putz, Mörtel, Estrich, Beton, Isoliermateπalien sowie Grundierungen Die erfindungsgemaß verwendbaren N-Octyl- und N-Decylsalicylsaureamide werden in die flussigen oder festen Baustoffe eingebracht, wie oben für die Mittel beschrieben Die Konzentration der erfindungsgemaß verwendbaren N-Octyl- und N- Decylsa cylsaureamide in den Mitteln oder Baustoffen kann durch den Fachmann in einem breiten Bereich variiert werden, abhangig von den Einsatzbedingungen der Mittel und Baustoffe Im Falle der Wasch- Reinigungs- und Nachspulmittel liegt die Konzentration der erfindungsgemaß verwendbaren N- Octyl- und N-Decylsalicylsaureamide vorzugsweise im Bereich von 0,01 Gew - % bis 5 Gew -%, insbesondere 0,1 Gew -% bis 3 Gew -% und besonders bevorzugt 0,1 Gew -% bis 2 Gew -%Another object of the present invention is the use of N-octylsalicyl acid amide and / or N-decylsalicyl acid amide as an antimicrobial, in particular as an antimycotic active ingredient in building materials, N-octylsahcyl-εaureamid and / or N-decylsalicyl acid amide being added to the building materials in the form of a Na-n-ion The amides mentioned can be used in all building materials which have to be protected against fungal attack. The building materials are particularly preferably selected from adhesives, sealants, fillers and paints, plastics, paints, paints, plaster, mortar, screed, concrete, insulating materials and Primers The N-octyl- and N-decylsalicylic acid amides which can be used according to the invention are introduced into the liquid or solid building materials, as described above for the agents vary in a wide range depending on the conditions of use of the agents and building materials. In the case of washing, cleaning and rinsing agents, the concentration of the N-octyl and N-decylsalicylic acid amides which can be used according to the invention is preferably in the range from 0.01% to 5% by weight. in particular 0.1% by weight to 3% by weight and particularly preferably 0.1% by weight to 2% by weight
Weitere Gegenstande der vorliegenden Erfindung sind Waschmittel, Reinigungsmittel, Nachspulmittel Handwaschmittel, Handgeschirrspulmittel, Maschi- nengeschirrspulmittel und Mittel zur Ausrüstung von Textilien, Pelzen, Papier, Fellen oder Leder, die N-Octylsalicylsaureamid und/oder N-Decylsalicylsaure- amid enthalten, insbesondere solche, denen N-Octylsalicylsaureamid und/oder N-Decylsalicylsaureamid in Form einer Nanodispersion zugesetzt wurde Weitere Gegenstände der vorliegenden Erfindung sind Baustoffe, insbesondere Klebe-, Dichtungs-, Spachtel- und Anstrichmassen, Kunststoffe, Lacke, Farben, Putz, Mörtel, Estrich, Beton, Isoliermaterialien sowie Grundierungen, die N- Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid enthalten, insbesondere solche, denen N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid in Form einer Nanodispersion zugesetzt wurde.The present invention furthermore relates to detergents, cleaning agents, rinse aid, hand wash detergent, hand dishwashing detergent, machine dishwashing detergent and agent for finishing textiles, furs, paper, furs or leather which contain N-octylsalicylic acid amide and / or N-decylsalicylic acid amide, in particular those to which N-octylsalicyl acid amide and / or N-decylsalicyl acid amide has been added in the form of a nanodispersion The present invention further relates to building materials, in particular adhesives, sealants, fillers and paints, plastics, paints, paints, plaster, mortar, screed, concrete, insulating materials and primers which contain N-octylsalicylic acid amide and / or N-decylsalicylic acid amide, especially those to which N-octylsalicylic acid amide and / or N-decylsalicylic acid amide has been added in the form of a nanodispersion.
Weitere Gegenstände der vorliegenden Erfindung sind Textilien, Pelze, Papier, Archivmaterialien, Felle oder Leder, ausgerüstet mit einem erfindungsgemäßen Mittel. Die Ausrüstung der Textilien, Pelze, Felle oder Leder erfolgt in dem Fachmann bekannter Weise, beispielsweise durch Eintauchen des Papiers oder der Textilien, Pelze, Felle oder Leder in eine geeignet konzentrierte Lösung eines erfindungsgemäßen Mittels.Further objects of the present invention are textiles, furs, paper, archive materials, skins or leather, equipped with an agent according to the invention. The textiles, furs, skins or leather are finished in a manner known to the person skilled in the art, for example by immersing the paper or the textiles, furs, skins or leather in a suitably concentrated solution of an agent according to the invention.
Die folgenden Beispiele erläutern die Erfindung, ohne sie jedoch darauf einzuschränken:The following examples illustrate the invention without, however, restricting it thereto:
Beispiel I:Example I:
1.1. Prüfsubstanzen1.1. test substances
Es wurde eine wässrige Nanodispersion von Salicylsäure-N-octylamid mit einem Wirkstoffgehalt von 1 % hergestellt. Das Prüfmuster hatte folgende Zusammensetzung:An aqueous nanodispersion of salicylic acid-N-octylamide with an active ingredient content of 1% was produced. The test sample had the following composition:
1 ,0% N-octylsalicylsäureamid1.0% N-octylsalicylic acid amide
2,15% Tagat S (Polyoxyethylen-glycerin-fettsäureester) 32,25% Wasser2.15% Tagat S (polyoxyethylene glycerol fatty acid ester) 32.25% water
32,25% Tego Betain 215 (Fettsäureamidoalkybetain) 32,25% Polydiol 40032.25% Tego Betaine 215 (fatty acid amido alkyl betaine) 32.25% Polydiol 400
Die Prüflösungen wurden durch Verdünnungen mit bidestilliertem Wasser hergestellt: 0, 1 % = 10,0g Dispersion in 100ml 0,5% = 25,0g Dispersion in 50mlThe test solutions were prepared by dilution with double-distilled water: 0.1% = 10.0g dispersion in 100ml 0.5% = 25.0g dispersion in 50ml
Als Referenzpraparat wurde eine antibakteriell und antimycotisch wirksame Rezeptur verwendet, die 70 Gew-% Didecyldimethylammoniumchlorid, 15 Gew-% Ethylenglycol, Rest Wasser umfasste Das Referenzpraparat wurde gleichfalls mit bidestilliertem Wasser verdünntAs a reference preparation, an antibacterial and antimycotic formulation was used, which comprised 70% by weight didecyldimethylammonium chloride, 15% by weight ethylene glycol, the rest water. The reference preparation was also diluted with double-distilled water
1.2. Prüfpilze1.2. test fungi
Candida albicans, ATCC 10231 , (Vorzucht auf CaSo-Agar, 4d/25°C), Aspergillus niger, ATCC 6275, (Vorzucht auf Malz-Agar, 8d/25°C), Tπchophyton mentagrophytes, ATCC 9533, (Vorzucht auf Malzagar, 8d/25°C), Cladosponum cladosponoides, DSM 62121 , (Vorzucht auf Malzagar, 8d/25°C), Epicoccum nigrum, Eigenisolat, (Vorzucht auf Malzagar, 8d/25°C)Candida albicans, ATCC 10231, (pre-breeding on CaSo agar, 4d / 25 ° C), Aspergillus niger, ATCC 6275, (pre-breeding on malt agar, 8d / 25 ° C), Tπchophyton mentagrophytes, ATCC 9533, (pre-breeding on malt agar , 8d / 25 ° C), Cladosponum cladosponoides, DSM 62121, (pre-cultivation on malt agar, 8d / 25 ° C), Epicoccum nigrum, self-isolate, (pre-cultivation on malt agar, 8d / 25 ° C)
Die Inocula wurden durch Abschwemmen der Vorzuchtplatten mit 0,05%igem Tween® 80 gewonnen und wiesen folgende Keimgehalte auf: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 ,9x 109 KBE/ml,Candida albicans 1.9 x 10 9 CFU / ml,
Aspergillus niger 1 ,0x107 KBE/ml,Aspergillus niger 1, 0x10 7 CFU / ml,
Trichophyton mentagrophytes 3,4x107 KBE/ml,Trichophyton mentagrophytes 3.4x10 7 CFU / ml,
Cladosporium cladosponoides 5 , Ox 107 KB E/m I ,Cladosporium cladosponoides 5, Ox 10 7 KB E / m I,
Epicoccum nigrum 1 , 9x 105 K B E/m I . (KBE: Koloniebildende Einheit)Epicoccum nigrum 1.9 x 10 5 CFU / ml. (KBE: colony forming unit)
1.3. Prüfung der fuπgistatischen Wirksamkeit im Hemmtest1.3. Testing the pediatric effectiveness in the inhibition test
1x1 cm große, vorgewaschene und autoklavierte Prüflinge aus Standardbaumwollgewebe nach DIN 53919 (WfK Testgewebe-GmbH, Adlerstr. 42, Krefeld) werden für 15 Min in die Pruflsgπ eingelegt, dann steril entnommen und 14 h bei Raumtemperatur getrocknet Je 0,1 ml Impfsuspensionen der o g Prüfpilze wurden in flussigen Malzagar einer Petπschale eingeimpft sowie nach Erstar- ren des Agars 0,1 ml auf der Agaroberfläche verspäten. Danach wurden die mit den Prüflösungen imprägnierten Prüflinge steril auf die Agaroberfläche aufgelegt und die Schalen 7 Tage bei 25 °C bebrütet. Danach erfolgte die Auswertung der Hemmwirkung nach folgendem Schema:1x1 cm large, pre-washed and autoclaved test specimens made from standard cotton fabric according to DIN 53919 (WfK Testgewebe-GmbH, Adlerstr. 42, Krefeld) are placed in the Pruflsgπ for 15 min, then removed sterile and dried for 14 h at room temperature. 0.1 ml vaccine suspensions each The above-mentioned test mushrooms were inoculated in liquid malt agar in a pet bowl and after initial Delay 0.1 ml of agar 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 = deutlicher Hemmhof, Angabe der Hemmzone in mm,0 = clear zone of inhibition, indication of the zone of inhibition in mm,
1 = kein Wachstum auf dem Prüfling, aber auch kein Hemmhof,1 = no growth on the test object, but also no inhibition zone,
2 = vereinzeltes Wachstum auf dem Prüfling,2 = isolated growth on the test object,
3 = mäßiges Wachstum auf dem Prüfling,3 = moderate growth on the test object,
4 = ungehemmtes Wachstum auf dem Prüfling.4 = uninhibited growth on the test specimen.
1.4. Prüfung der fungiziden Wirksamkeit im DGHM-Keimträgertest1.4. Examination of the fungicidal effectiveness in the DGHM germ carrier test
Die Prüfung erfolgte in Anlehnung an die Richtlinien für die Prüfung und Bewertung chemischer Desinfektionsverfahren der Deutschen Gesellschaft für Hygiene und Mikrobiologie (DGHM), Gustav Fischer Verlag, 1981 : Je 16 vorgewaschene und autoklavierte Prüflinge wurden in die o.g. Impfsuspensionen der Prüfpilze eingelegt und mit mehrmaligem Umwenden für 15 Min. darin belassen. Danach wurden die so kontaminierten Prüflinge in leere Petri- schalen überführt und mit je 10 ml der Prüflösungen übergössen. Nach 60 und 120 Min. Einwirkzeit bei 20 °C wurden je 2 der Prüflinge entnommen und kurzzeitig in 10 ml Inaktivatorlösung gemäß DGHM-Richtlinie überführt und daraus auf CaSo- (Candida) bzw. Malzagar-Platten (übrige Prüfpilze) verimpft. Die Bebrütung erfolgte 7 Tage bei 25° C. Danach erfolgte die Auswertung qualitativ, d.h. Wachstum ja (+) oder nein (-).The 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 each of the above. Vaccine suspensions of the test mushrooms are placed and left in for 15 minutes with repeated turning. 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. After an exposure time of 60 and 120 minutes at 20 ° C, 2 of the test specimens were removed and briefly transferred to 10 ml inactivator solution in accordance with the DGHM guideline and inoculated therefrom onto CaSo (Candida) or malt agar plates (other test fungi). The incubation was carried out at 25 ° C for 7 days. Growth yes (+) or no (-).
2. Ergebnisse2 results
2.1. Fungistatische Wirksamkeit2.1. Fungistatic effectiveness
2.1.1. Die Prüfung der Hemmwirksamkeit von N-octylsalicylsäureamid (SaINo) erbrachte folgende Ergebnisse:
Figure imgf000016_0001
2.1.1. The test of the inhibitory activity of N-octylsalicylic acid amide (SaINo) yielded the following results:
Figure imgf000016_0001
2.1.3. Im Vergleich die fungistatische Wirksamkeit des Referenzpräparates (R):2.1.3. In comparison the fungistatic effectiveness of the reference product (R):
Figure imgf000016_0002
Figure imgf000016_0002
2.2. Fungizide Wirksamkeit2.2. Fungicidal effectiveness
2.2.1. Die Prüfung der fungiziden Wirksamkeit von N-octylsalicylsäureamid (SaINo) erbrachte folgende Ergebnisse (+= lebende Kultur, -= abgetötete Kultur):
Figure imgf000017_0001
2.2.1. Examination of the fungicidal activity of N-octylsalicylic acid amide (SaINo) yielded the following results (+ = living culture, - = killed culture):
Figure imgf000017_0001
2 2 3 Die Vergleichsprufung mit dem Referenzpraparat ergab für alle Prüfpilze bis zur höchsten Prufkonzentration von 250 ppm positives Wachstum2 2 3 The comparison test with the reference preparation showed positive growth for all test fungi up to the highest test concentration of 250 ppm
3. Ergebnis'3. Result '
Das N-octylsalicylsaureamid zeigt im Vergleich zu dem Referenzpraparat eine sehr gute fungistatische Wirksamkeit sowohl gegen Dermatophyten als auch gegen Stockflecken erzeugende oder Material-schädliche PilzeCompared to the reference preparation, the N-octylsalicylic acid amide shows a very good fungistatic activity against both dermatophytes and fungi which produce mold stains or are harmful to the material
Beispiel II-Example II
1.1 Prufsubstanzen1.1 Test substances
Es wurde eine wassrige Nanodispersion von Salicylsaure-N-octylamid hergestellt Das Prüfmuster (1 ) hatte folgende ZusammensetzungAn aqueous nanodispersion of salicylic acid N-octylamide was produced. The test sample (1) had the following composition
1 ,07 g Salicylsaure-N-octylamid1.07 g of salicylic acid N-octylamide
2,15 g Tagat S (Polyoxyethylen-glycenn-fettsaureester) 32,26 g Wasser2.15 g Tagat S (polyoxyethylene glycenn fatty acid ester) 32.26 g water
32,26 g Tego Betain 215 (Fettsäureamidoalkylbetain)32.26 g Tego Betaine 215 (fatty acid amidoalkyl betaine)
32,26 g Polydiol 40032.26 g Polydiol 400
Als Prüfmuster (2) wurde eine 10 %ige wassrige Verdünnung des nanodispergierten Wirkstoffpräparats (1) eingesetzt.A 10% aqueous dilution of the nanodispersed active substance preparation (1) was used as the test sample (2).
Als Prüfmuster (3) wurde eine 1 %ige wassrige Dispersion eines antibakteriellen und antimycotischen nanodispergierten Referenzpräparates eingesetzt, das folgende Zusammensetzung aufwies:A 1% aqueous dispersion of an antibacterial and antimycotic nanodispersed reference preparation, which had the following composition, was used as test sample (3):
20 % Dehyquart AU 56 20% Plantacare 1200UP 60 % Wasser20% Dehyquart AU 56 20% Plantacare 1200UP 60% water
Als Prüfmuster (4) wurde bidest. Wasser eingesetzt.The test sample (4) was bidest. Water used.
Alle Verdünnungen erfolgten in bidest. WasserAll dilutions were made in bidist. water
1.2. Prüfmethoden1.2. Test Methods
Die Prüfung der Hemmwirksamkeit (Mikrobistase) erfolgte im Agarlochtest nach folgender Vorschrift:The inhibitory activity (microbistase) was tested in the agar hole test according to the following rule:
a. Prinzip der Methodea. Principle of the method
Die zu testende Substanz wird in ein ausgestanztes Loch einer Agarplatte gefüllt und diffundiert in den Agar, welcher mit einem geeigneten oder geforderten Testorganismus beimpft wurde. Wird der Testorganismus durch die Substanz gehemmt, so entsteht beim anschließenden Bebrüten der Agarplatte ein sichtbarer Hemmhof um das Loch herum.The substance to be tested is filled into a punched-out hole in an agar plate and diffuses into the agar which has been inoculated with a suitable or required test organism. If the test organism is inhibited by the substance, a visible zone of inhibition is created around the hole when the agar plate is subsequently incubated.
b. Testorganismen Die Wahl der Testorganismen hangt von der konkreten Fragestellung ab. Die im vorliegenden Fall verwendeten Organismen sind aus Tabelle 1 ersichtlich.b. test organisms The choice of test organisms depends on the specific question. The organisms used in the present case are shown in Table 1.
c. Vorbereitung der Testorganismenc. Preparation of the test organisms
Bakterien werden in Standard I-Nahrbouillon angeimpft und 18-24 Stunden bei 37 °C bebrütet Die bewachsene Kultur wird 1 100 mit Standard I-Nahrbouillon verdünnt. Pilze werden auf Wurzeagar 7 Tage bei 30 °C vorgezuchtet und der Bewuchs einer Platte mit 2 x 5ml Wurzebouillon abgeschwemmt. Das abgeschwemmte Material wird durch Glaswolle filtriert und durch Schuttein in einer Schliffstopfenflasche mit Glasperlen (Boden in etwa mit Glasperlen bedeckt) homogenisiertBacteria are inoculated in standard I nutrient broth and incubated at 37 ° C for 18-24 hours. The overgrown culture is diluted 1 100 with standard I nutrient broth. Mushrooms are pre-grown on root agar for 7 days at 30 ° C and the growth of a plate with 2 x 5 ml of root broth is washed away. The washed-off material is filtered through glass wool and homogenized by rubbing in a glass stopper bottle with glass beads (the bottom is approximately covered with glass beads)
d. Versuchsdurchführungd. Experimental Procedure
1 ml der Testorganismensuspension wird in 200ml verflüssigten auf 45 °C abgekühlten Standard I-Nahragar (Bakterien) bzw. Wurzeagar (Pilze) eingemischt. Sofort anschließend werden davon Agarplatten gegossen (ca. 20ml Agar pro Platte). Nach dem Verfestigen des Agars wird in die Mitte der Platte mit einem sterilen Korkbohrer ein Loch von 10mm Durchmesser gestanzt. In dieses Loch wird die zu testende Substanz (oder je nach Ziel des Versuchs Verdünnungen der Substanz) eingefüllt. Es ist darauf zu achten, daß die Substanz nur in das Loch und nicht auf die Agaroberfläche gelangt Die Platten werden bei 37 °C (Bakterien) bzw 30 °C (Pilze) bebrütet bis auf einer Vergleichsplatte mit Wasser statt Prufsubstanz ein guter Rasenwuchs des Testorganismus zu beobachten ist Alternativ zu diesem Vorgehen können - wenn eine Fragestellung dies erfordert - Filterpapier- oder Gewebescheiben definierter Große in einer Lösung der Prufsubstanz getrankt und auf den beimpften Agar aufgelegt werden.1 ml of the test organism suspension is mixed into 200 ml of liquid standard I food agar (bacteria) or root agar (fungi) cooled to 45 ° C. Agar plates are then poured immediately thereafter (approx. 20 ml agar per plate). After the agar has solidified, a 10 mm diameter hole is punched into the center of the plate using a sterile cork bur. The substance to be tested (or, depending on the aim of the experiment, dilutions of the substance) is filled into this hole. It must be ensured that the substance only gets into the hole and not on the agar surface. The plates are incubated at 37 ° C (bacteria) or 30 ° C (fungi) until a test plate with water instead of test substance gives the test organism good lawn growth As an alternative to this procedure, filter paper or tissue disks of defined sizes can be soaked in a solution of the test substance and placed on the inoculated agar - if a question requires it.
e. Auswertunge. evaluation
Die Große der entstandenen Hemmhofe wird vom Lochrand ausgemessen. Ist die ganze Platte ohne Bewuchs, so muß die Prufsubstanz starker verdünnt und erneut getestet werden f. ErgebnisThe size of the inhibition yards created is measured from the edge of the hole. If the entire plate is without growth, the test substance must be diluted more and tested again f. Result
Als Ergebnis wird für jeden Testorganismus der Hemmhofradius angegeben.The inhibition radius is given as the result for each test organism.
Die Prüfung der mikrobiziden Wirksamkeit erfolgte in Anlehnung an EN 1040 (Bakterizidie) bzw. EN 1275 (Fungizidie) jeweils mit erweitertem Testkeimspektrum, das der Tabelle 2 zu entnehmen ist.The microbicidal activity was tested in accordance with EN 1040 (bactericidal) and EN 1275 (fungicidal), each with an expanded spectrum of test germs, which can be seen in Table 2.
2. Ergebnisse2 results
Die Ergebnisse finden sich in den Tabellen 1 und 2 (Tab. 1 : MikrobistatischeThe results can be found in Tables 1 and 2 (Tab. 1: Microbistatic
Wirksamkeit; Tab. 2: Mikrobizide Wirksamkeit) Effectiveness; Tab. 2: Microbicidal effectiveness)
Tab 1 Prüfung der mikrobistatischen Wirksamkeit im Agarlochtest Angegeben sind die Hemmhofe in mm von 2 ParallelenTab 1 Testing the microbistatic effectiveness in the agar hole test The inhibition zones are given in mm of 2 parallels
Figure imgf000021_0001
Figure imgf000021_0001
Tab.2 Prüfung der mikrobiziden Wirksamkeit gem. EN 1040 bzw. EN 1275 Angegeben sind log. ReduktionsfaktorenTab. 2 Testing the microbicidal effectiveness according to EN 1040 and EN 1275 are given log. reduction factors
Figure imgf000022_0001
Figure imgf000022_0001
3. Ergebnis:3. Result:
Das N-octylsalicylsäureamid zeigt im Vergleich zu dem Referenzpräparat eine sehr gute mikrobistatische und mikrobizide Wirksamkeit sowohl gegen Bakterien als auch gegen Pilze. Compared to the reference preparation, the N-octylsalicylic acid amide shows a very good microbistatic and microbicidal activity against both bacteria and fungi.

Claims

Patentansprüche: claims:
1. Verwendung von N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid als antimikrobieller Wirkstoff in Waschmitteln; Reinigungsmit- teln; Nachspülmitteln; Handwaschmitteln; Handgeschirrspülmitteln; Maschinen- geschirrεpülmitteln und Mitteln zur Ausrüstung von Textilien, Pelzen, Papier, Fellen oder Leder.1. Use of N-octylsalicylic acid amide and / or N-decylsalicylic acid amide as an antimicrobial agent in detergents; Cleaning agents; rinse aid; Hand washing; Hand dishwashing detergents; Machine dishwashing detergents and agents for finishing textiles, furs, paper, furs or leather.
2. Verwendung nach Anspruch 1 , wobei N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid in Form einer Nanodispersion eingesetzt werden.2. Use according to claim 1, wherein N-octylsalicylic acid amide and / or N-decylsalicylic acid amide are used in the form of a nanodispersion.
3. Verwendung von N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid als antimikrobieller, insbesondere antimycotischer Wirkstoff in Baustoffen.3. Use of N-octylsalicylic acid amide and / or N-decylsalicylic acid amide as an antimicrobial, in particular antimycotic active ingredient in building materials.
4. Verwendung nach Anspruch 3, wobei N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid in Form einer Nanodispersion eingesetzt werden.4. Use according to claim 3, wherein N-octylsalicylic acid amide and / or N-decylsalicylic acid amide are used in the form of a nanodispersion.
5. Verwendung nach Anspruch 3 oder 4, wobei die Baustoffe ausgewählt sind unter Klebe-, Dichtungs-, Spachtel- und Anstrichmassen, Kunststoffen, Lacken, Farben, Putz, Mörtel, Estrich, Beton, Isoliermaterialien sowie Grundierungen.5. Use according to claim 3 or 4, wherein the building materials are selected from adhesives, sealants, fillers and paints, plastics, paints, paints, plaster, mortar, screed, concrete, insulating materials and primers.
6. Waschmittel; enthaltend N-Octylsalicylsäureamid und/oder N-Decyl- salicylsäureamid.6. detergent; containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
7. Reinigungsmittel; enthaltend N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid.7. cleaning agents; containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
8. Nachspülmittel; enthaltend N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid. 8. rinse aid; containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
9. Haπdwaschmittel; enthaltend N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid.9. hand detergent; containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
10. Handgeschirrspülmittel; enthaltend N-Octylsalicylsäureamid und/oder N- Decylsalicylsäureamid.10. hand dishwashing liquid; containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
11. Maschinengeschirrspülmittel, enthaltend N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid.11. Machine dishwashing detergent, containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
12. Mittel zur Ausrüstung von Textilien, Pelzen, Papier, Fellen oder Leder, enthaltend N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid.12. Means for finishing textiles, furs, paper, skins or leather, containing N-octylsalicylic acid amide and / or N-decylsalicylic acid amide.
13. Mittel nach einem der Ansprüche 6 bis 12, dadurch gekennzeichnet, daß ihnen N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid in Form einer Nanodispersion zugesetzt wurde.13. Composition according to one of claims 6 to 12, characterized in that N-octylsalicylic acid amide and / or N-decylsalicylic acid amide in the form of a nanodispersion has been added to them.
14. Baustoffe, insbesondere Klebe-, Dichtungs-, Spachtel- und Anstrichmassen, Kunststoffe, Lacke, Farben, Putz, Mörtel, Estrich, Beton, Isoliermaterialien sowie Grundierungen, enthaltend N-Octylsalicylsäureamid und/oder N-Decyl- salicylsäureamid.14. Building materials, in particular adhesives, sealants, fillers and paints, plastics, paints, paints, plaster, mortar, screed, concrete, insulating materials and primers, containing N-octylsalicylic acid amide and / or N-decyl salicylic acid amide.
15. Baustoffe nach Anspruch 14, dadurch gekennzeichnet, daß ihnen N- Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid in Form einer Nanodispersion zugesetzt wurde.15. Building materials according to claim 14, characterized in that N-octylsalicylic acid amide and / or N-decylsalicylic acid amide in the form of a nanodispersion has been added to them.
16. Textilien, Pelze, Papier, Felle oder Leder, ausgerüstet mit einem Mittel nach Anspruch 12 oder 13. 16. Textiles, furs, paper, skins or leather, equipped with an agent according to claim 12 or 13.
PCT/EP2001/003692 2000-04-12 2001-03-31 Use of n-octyl salicylic acid amide and/or n-decyl salicylic acid amide as antimicrobial active ingredient WO2001079405A1 (en)

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DE1593552A1 (en) * 1965-12-07 1970-08-06 Stecker Chemicals Inc Process for the preparation of new salicylamide compounds
DE2430365A1 (en) * 1973-06-25 1975-01-23 Yoshitomi Pharmaceutical SALICYLANILIDES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE IN ANTIFOULING AGENTS
EP0262587A2 (en) * 1986-10-02 1988-04-06 Henkel Kommanditgesellschaft auf Aktien Salicylic acid amides, method for their production and their application

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DE1593552A1 (en) * 1965-12-07 1970-08-06 Stecker Chemicals Inc Process for the preparation of new salicylamide compounds
DE2430365A1 (en) * 1973-06-25 1975-01-23 Yoshitomi Pharmaceutical SALICYLANILIDES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE IN ANTIFOULING AGENTS
EP0262587A2 (en) * 1986-10-02 1988-04-06 Henkel Kommanditgesellschaft auf Aktien Salicylic acid amides, method for their production and their application

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