EP2408889A1 - Detergent, cleaning agent, aftertreatment agent, or washing aid containing aldehydes and having an antibacterial effect - Google Patents
Detergent, cleaning agent, aftertreatment agent, or washing aid containing aldehydes and having an antibacterial effectInfo
- Publication number
- EP2408889A1 EP2408889A1 EP10707299A EP10707299A EP2408889A1 EP 2408889 A1 EP2408889 A1 EP 2408889A1 EP 10707299 A EP10707299 A EP 10707299A EP 10707299 A EP10707299 A EP 10707299A EP 2408889 A1 EP2408889 A1 EP 2408889A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- silver
- washing
- cleaning
- methyl
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
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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
- C11D3/16—Organic compounds
- C11D3/168—Organometallic compounds or orgometallic complexes
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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
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/046—Salts
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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
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/1206—Water-insoluble compounds free metals, e.g. aluminium grit or flakes
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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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
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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
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3942—Inorganic per-compounds
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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
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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
- C11D3/50—Perfumes
Definitions
- the invention relates to an aldehyde-containing washing, cleaning, aftertreatment or washing aid having an antibacterial effect, comprising elemental silver and / or a silver compound.
- the invention also relates to the use and a method for producing such a washing, cleaning, aftertreatment or washing aid.
- adhesion of microorganisms to surfaces is undesirable, especially in pathogenic microorganisms.
- Adherent microorganisms often lead to infections or reinfection in humans, animals and plants.
- More and more sensitive textiles such as silk or microfibre, are processed into garments that can only be washed at 30 or 40 ° C. As a result, fungi, such as the human pathogenic Candida albicans, are not killed.
- contaminated textiles can not be sterilized to the required extent by the changed washing behavior with viruses, bacteria, mold or yeast fungi, so that a (re-) infection may occur during renewed contact of the consumer with the supposedly pure laundry.
- problems with bad odors can occur because residual germs multiply when drying, carrying or storing on the laundry and produce bad-smelling metabolite products.
- problems with bad odors can occur because residual germs multiply when drying, carrying or storing on the laundry and produce bad-smelling metabolite products.
- inside a washing machine itself can be caused by adhering biofilms a bad smell.
- Antimicrobially active compositions and their use in washing, cleaning, aftertreatment or washing aids are known in the art.
- the disinfectants used are halogen-containing substances or phenol derivatives or other aromatic hydrocarbons, which can be regarded as problematic for reasons of environmental compatibility.
- Other, more compatible microbicides have only a limited spectrum of activity or are effective only under certain physical conditions.
- Natural ingredients are also desirable.
- silver or silver ions have a blocking effect on thiol enzymes in microorganisms and thus have a high bactericidal and fungicidal action.
- silver has a germicidal effect.
- EP 1670885 A1 germ-reducing detergents or cleaners containing silver and / or silver ions are already known.
- compositions containing silver and / or silver ions are not stable because the silver ions contained in the agents can react with impurities such as chloride ions to photosensitive silver chloride salts or as sulfide to poorly soluble silver sulfide salts.
- impurities such as chloride ions to photosensitive silver chloride salts or as sulfide to poorly soluble silver sulfide salts.
- soluble silver ions can first react to AgOH and then further to sparingly soluble Ag 2 O.
- the silver oxides and silver sulfides cause considerable color changes, in particular a brown or black color, of the composition despite small amounts.
- An object of this invention was therefore to provide a stable, aldehyde-containing washing, cleaning, aftertreatment or washing aid with antibacterial activity.
- a washing, cleaning, aftertreatment or washing aid comprising a
- the silver compound is selected from the group consisting of silver acetate, silver citrate, silver diamine chloride complex, silver cyclodextrin complex, silver dicyanokalium complex, silver phthalimide, silver phenylcyanamide, silver (ethylene thiourea) complex, silver imidazolate, transition metal NHC-calix [4] arene Complexes, silver crown ethers, silver nitrate, Silver chloride on a support material and mixtures thereof is selected.
- the washing, cleaning, aftertreatment or washing aid contains silver nitrate or silver chloride on a support material.
- silver compounds have a sufficiently high solubility and are not excluded from the washing, cleaning, aftertreatment or washing aids.
- the amount of elemental silver and / or the silver compound is from 0.0001 to 1% by weight, based on the total washing, cleaning, after-treatment or washing assistant.
- the aldehyde compound is a fragrance. It is particularly preferred that the aldehyde compound is selected from the group consisting of 1, 3-benzodioxole-5-carboxaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 2-methyldecanal, 4- (1-methylethyl) benzaldehyde, 10th Undecenal, 2-methylundecanal, n-propanal, n-butanal, n-pentanal, n-hexanal, n-heptanal, n-octanal, n-nonanal, n-decanal, n-undecanal, n-dodecal, 2- ( Phenylmethylene) heptanal, benzaldehyde, 4-methoxybenzaldehyde, 4-methylbenzaldehyde, 3- (4-tert-butylphenyl) isobutyraldehyde, 2-
- the scent impression of a washing, cleaning, aftertreatment or washing aid itself as well as the fragrance impression left by a washing, cleaning, aftertreatment or washing aid in a textile treated with it, is often a decisive factor for the purchasing decision of consumers.
- the listed aldehyde compounds are customary and frequently used fragrances, which contribute decisively to the fragrance impression of a perfume composition.
- the washing, cleaning, aftertreatment or washing aid additionally contains 0.01 to 3 wt .-%, based on the total washing, cleaning, aftertreatment or washing aid, ammonium hydroxide. Surprisingly, it has been found that particularly clear and thus aesthetically pleasing compositions are obtained by adding even small amounts of ammonium hydroxide.
- the invention also relates to the use of a washing, cleaning, aftertreatment or washing aid according to the invention in the washing, cleaning, pretreatment and / or conditioning of textiles.
- the invention also relates to a process for the preparation of a washing, cleaning, aftertreatment or washing aid, comprising (a) an aldehyde compound and (b) elemental silver and / or a silver compound, wherein the aldehyde compound and the elemental Silver and / or the silver compound can be added by means of a perfume composition which additionally contains hydrogen peroxide.
- Perfume compositions are usually added at the end of a manufacturing process of laundry, cleaning, aftertreatment or washing aids.
- the perfume composition can be used to easily and quickly add the least amount of aldehyde compound, hydrogen peroxide, elemental silver and / or silver compound to a washing, cleaning, after-treatment or washing assistant.
- the invention also relates to the use of hydrogen peroxide to stabilize an aldehyde-containing composition comprising silver and / or a silver compound.
- the invention also relates to a perfume composition, preferably for use in a washing, cleaning, after-treatment or washing aid, comprising (a) elemental silver and / or a silver compound, (b) an aldehyde compound and (c) hydrogen peroxide.
- the washing, cleaning, after-treatment or washing aid contains elemental silver and / or a silver compound.
- silver is used either in elemental form or in the form of its compounds. If the silver is used in elemental form, it preferably has particle sizes of 1 nm to 100 ⁇ m. Even finer particle sizes of silver can be achieved by using the elemental silver in colloidal form, wherein the silver has particle sizes of 0.001 to 0.1 microns.
- the agent contain a silver compound and that silver compound is selected from the group consisting of silver acetate, silver citrate, silver diamine chloride complex, silver cyclodextrin complex, silver dicyanokalium complex, silver phthalimide, silver phenylcyanamide, silver (ethylene thiourea) complex, silver imidazolate, Transition metal NHC-calix [4] arene complexes, silver crown ethers, silver nitrate, silver chloride on a support material and mixtures thereof.
- the silver compounds are preferably used in the form of solutions, suspensions or dispersions.
- the washing, cleaning, aftertreatment or washing aid contains silver nitrate, which in the form an aqueous solution is used, or silver chloride on titanium dioxide as a carrier material, which is used as an aqueous dispersion.
- the amount of elemental silver and / or silver compound is preferably from 0.0001 to 1% by weight, and more preferably from 0.001 to 0.25% by weight, based on the total washing, cleaning, after-treatment or washing aid.
- Very particularly preferred washing, cleaning, after-treatment or washing auxiliaries contain from 0.001 to 0.1% by weight of elemental silver and / or a silver compound, based on the total washing, cleaning, after-treatment or washing assistant.
- the washing, cleaning, aftertreatment or washing aid contains an aldehyde compound.
- Aldehydes can be used for a variety of purposes, such as for disinfection, in detergents, cleaners, aftertreatment or washing aids.
- a main field of application is the use as a fragrance in perfume compositions.
- Suitable aldehyde fragrances which may be included in a washing, cleaning, after-treatment or washing aid include, for example, 1,3-benzodioxole-5-carboxaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 2-methyldecanal, 4- (1 - methylethyl) benzaldehyde, 10-undecenal, 2-methylundecanal, n-propanal, n-butanal, n-pentanal, n-hexanal, n-heptanal, n-octanal, n-nonanal, n-decanal, n-undecanal, n Dodecal, 2- (phenylmethylene) heptanal, benzaldehyde, 4-methoxybenzaldehyde, 4-methylbenzaldehyde, 3- (4-tert-butylphenyl) isobutyraldehyde, 2-phenylpropanal,
- the aldehyde is a constituent of a perfume composition and thus enters the washing, cleaning, aftertreatment or washing aid.
- the amount of aldehyde compound may be between 0.001 and 5 wt .-% based on the total washing, cleaning, aftertreatment or washing aid.
- the aldehydes used the primary performance of germicidal agent, here elemental silver or a silver compound, support, that is, even have an antibacterial / germicidal effect.
- the perfume composition may contain, in addition to one or more aldehyde compound (s), other perfume compounds such as ester type synthetic products, ethers, ketones, alcohols, and hydrocarbons. Preferably, mixtures of different fragrances are used, which together produce an attractive fragrance.
- a perfume composition may also contain natural fragrance mixtures as available from plant sources.
- the perfume composition may comprise organic solvents and / or surfactants.
- the composition contains hydrogen peroxide.
- the amount of hydrogen peroxide is preferably between 0.01 and 5 wt .-%, and more preferably between 0.1 and 2.5 wt .-%.
- the hydrogen peroxide serves as a "sacrificial anode" in the aldehyde- and silver-containing agents and prevents undesired reactions between the aldehydes and the silver compound .
- the hydrogen peroxide prevents oxidation of the aldehydes by the silver compounds Reactions with the other ingredients, such as the fragrance compounds, the washing, cleaning, aftertreatment or washing aids, received.
- the washing, cleaning, aftertreatment or washing aid may contain further ingredients which have the performance and / or aesthetic properties of the washing, cleaning, aftertreatment or detergency further improve.
- the washing, cleaning, after-treatment or washing assistant preferably additionally contains one or more substances from the group of surfactants, builders, bleaching agents, bleach catalysts, bleach activators, enzymes, electrolyte, nonaqueous solvents, pH adjusters, perfume compositions , Perfume carriers, fluorescers, dyes, hydrotopes, foam inhibitors, silicone oils, soil release polymers, grayness inhibitors, shrinkage inhibitors, wrinkle inhibitors, dye transfer inhibitors, other antimicrobial agents, germicides, fungicides, antioxidants, preservatives, corrosion inhibitors, antistatic agents, bittering agents, ironing auxiliaries, phobies and Impregnating agent, swelling and anti-slip agents, softening components and UV absorbers.
- surfactants builders, bleaching agents, bleach catalysts, bleach activators, enzymes, electrolyte, nonaqueous solvents, pH adjusters, perfume compositions , Perfume carriers, fluorescers, dyes, hydrotopes, foam inhibitors, silicone oils, soil
- Particularly preferred additional ingredients are surfactants, builders, enzymes, electrolytes, non-aqueous solvents, pH adjusters, perfume compositions, fluorescers, dyes, hydrotopes, foam inhibitors, soil release polymers, grayness inhibitors, dye transfer inhibiting agents, plasticizing components, UV absorbers and mixtures thereof ,
- the washing, cleaning, aftertreatment or washing aid preferably contains 1 to 60 wt .-% of a surfactant selected from the group consisting of anionic, nonionic, cationic and zwitterionic surfactants and mixtures thereof.
- Suitable nonionic surfactants include alkoxylated fatty alcohols, alkoxylated fatty acid alkyl esters, fatty acid amides, alkoxylated fatty acid amides, polyhydroxy fatty acid amides, alkylphenol polyglycol ethers, and mixtures thereof.
- the nonionic surfactants used are preferably alkoxylated, advantageously ethoxylated, in particular primary, alcohols having preferably 8 to 18 carbon atoms and on average 1 to 12 moles of ethylene oxide (EO) per mole of alcohol, in which the alcohol radical can be linear or preferably methyl-branched in the 2-position or linear and methyl-branched radicals in the mixture can contain, as they are usually present in Oxoalkoholresten.
- EO ethylene oxide
- alcohol ethoxylates with linear radicals of alcohols of native origin having 12 to 18 carbon atoms, for example of coconut, palm, tallow or oleyl alcohol, and on average 2 to 8 EO per mole of alcohol are preferred.
- Preferred ethoxylated alcohols include, for example, C12 - 14 - alcohols containing 3 EO, 4 EO or 7 EO, C 9 n-alcohol with 7 EO, C-ms alcohols containing 3 EO, 5 EO, 7 EO or 8 EO , C-
- the degrees of ethoxylation given represent statistical means which, for a particular product, may be an integer or a fractional number.
- Preferred alcohol ethoxylates have a narrow homolog distribution (narrow rank ethoxylates, NRE).
- fatty alcohols with more than 12 EO can also be used. Examples of these are tallow fatty alcohol with 14 EO, 25 EO, 30 EO or 40 EO.
- Nonionic surfactants containing EO and PO groups together in the molecule can also be used according to the invention.
- the washing, cleaning, aftertreatment or washing aid contains a C 12 -i 8 -fatty alcohol with 7 EO or a Ci 3 -i 5 -oxo-alcohol with 7 EO as nonionic surfactant.
- Suitable amine oxides include, for example, alkylamine oxides, especially alkyldimethylamine oxides, alkylamidoamine oxides and alkoxyalkylamine oxides. Preferred amine oxides satisfy formula II,
- R 7 , R 8 are independently a C
- Preferred amine oxides are, for example, N-cocoalkyl-N, N-dimethylamine oxide, N-tallowalkyl-N, N-dihydroxyethylamine oxide, myristylcetyldimethylamine oxide or lauryldimethylamine oxide.
- the content of amine oxide is in the washing, cleaning, aftertreatment or washing aid preferably 1 to 15 wt .-%, preferably 2 to 10 wt .-%, each based on the total washing, cleaning, aftertreatment or washing aid ,
- the washing, cleaning, after-treatment or washing assistant may also contain an anionic surfactant as a washing assistant compound.
- the anionic surfactant used is preferably sulfonates, sulfates, soaps, alkyl phosphates, anionic silicotensides and mixtures thereof.
- Suitable surfactants of the sulfonate type are preferably C 9 .i 3 -alkylbenzenesulfonates, olefinsulfonates, ie mixtures of alkene and hydroxyalkanesulfonates and also disulfonates, as are known for example from C 1 2-18 monoolefins with terminal or internal double bond by sulfonation with gaseous sulfur trioxide and subsequent alkaline or acidic hydrolysis of the sulfonation products into consideration.
- C 2 -i 8 alkanesulfonates and the esters of ⁇ -sulfofatty acids for example, the ⁇ -sulfonated Methylester of hydrogenated coconut, palm kernel or tallow fatty acids.
- Alk (en) yl sulfates are the alkali and especially the sodium salts of the Schwefelhoffreraumester C 2 -C 8 fatty alcohols, for example coconut fatty alcohol, tallow fatty alcohol, lauryl, myristyl, cetyl or stearyl alcohol, or d 0 -C 2 o Oxo alcohols and those half-esters of secondary alcohols of these chain lengths are preferred.
- the C 12 -C 16 alkyl sulfates and C 12 -C 15 alkyl sulfates and C 14 -C 5 alkyl sulfates are preferred.
- 2,3-alkyl sulfates are also suitable anionic surfactants.
- sulfuric acid monoesters of straight-chain or branched C 7 ethoxylated with 1 to 6 moles of ethylene oxide are suitable.
- 21 -alcohols such as 2-methyl-branched Cg-n-alcohols having an average of 3.5 moles of ethylene oxide (EO) or C 12 . 18 fatty alcohols with 1 to 4 EO are suitable.
- anionic surfactants are soaps.
- Suitable are saturated and unsaturated fatty acid soaps, such as the salts of lauric acid, myristic acid, palmitic acid, stearic acid, (hydrogenated) erucic acid and behenic acid and, in particular, soap mixtures derived from natural fatty acids, for example coconut, palm kernel, olive oil or tallow fatty acids.
- the anionic surfactants including the soaps may be in the form of their sodium, potassium or magnesium or ammonium salts.
- the anionic surfactants are in the form of their sodium salts.
- Further preferred counterions for the anionic surfactants are also the protonated forms of choline, triethylamine or methylethylamine. It may be preferred that a fatty acid soap be present in admixture with the unneutralized fatty acid, since the unneutralized fatty acid may further stabilize the silver-containing washing, cleaning, after-treatment or washing aid, in particular the elemental silver and / or the silver compound, causes.
- Conditioners in the form of fabric softeners preferably contain cationic surfactants which have a softening effect.
- the cationic surfactants include, for example, quaternary ammonium compounds such as monoalk (en) yltrimethylammonium compounds, dialk (en) yldimethylammonium compounds, mono-, di- or triesters of fatty acids with alkanolamines.
- quaternary ammonium compounds are shown, for example, in the formulas (I) to (III):
- R is an acyclic alkyl radical having 12 to 24 carbon atoms
- R 1 is a saturated C 1 -C 4 alkyl or hydroxyalkyl radical
- R 2 and R 3 are either equal to R or R 1 or are an aromatic radical.
- X " represents either a halide, methosulfate, methophosphate or phosphate ion and mixtures of these
- Examples of cationic compounds of the formula (I) are monotaltrimethylammonium chloride, monostearyltrimethylammonium chloride, didecyldimethylammonium chloride, ditallowdimethylammonium chloride or dihexadecylammonium chloride.
- R 4 is an aliphatic alk (en) yl radical having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds and / or optionally with substituents;
- R 5 is H, OH or O (CO) R 7 ,
- R 6 is, independently of R 5, H, OH or O (CO) R 8 , where R 7 and R 8 are each independently an aliphatic alk (ene) ylrest having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds, m, n and p may each independently have the value 1, 2 or 3 have.
- X " can either a halide, methosulfate, methophosphate or phosphate ion, as well as mixtures of these anions. Preference is given to compounds in which R 5 represents the group 0 (CO) R 7 .
- R 5 is the group 0 (CO)
- R 7 and R 4 and R 7 are alk (en) yl radicals having 16 to 18 carbon atoms.
- R 6 is also OH.
- R 12 , R 13 and R 14 are independently of one another a C-. 4 alkyl, alkenyl or hydroxyalkyl group
- R 15 and R 16 each selected independently a C 8-28 alkyl group
- X ⁇ is an anion
- r is a number between 0 and 5.
- Examples include methyl N- (2-hydroxyethyl) -N, N-di (tallowacyloxyethyl) ammonium methosulfate, bis (palmitoyloxyethyl) hydroxyethyl methyl ammonium methosulfate, 1,2-bis (tallowacyloxy) -3- trimethylammoniumpropane chloride, methyl N, N-bis (stearoyloxyethyl) -N- (2-hydroxyethyl) ammonium methosulfate or N, N-dimethyl-N, N-di (tallowacyloxyethyl) ammonium methosulfate.
- ester group 0 (CO) R where R is a long-chain alk (en) yl radical
- softening compounds which have the following groups: RO (CO), N (CO) R or RN (CO), where of these groups, N (CO) R groups are preferred.
- the other ingredients and the physical parameters of the washing, cleaning, aftertreatment or washing aids are determined by their field of application (universal detergent, color detergent, softener, etc.). A person skilled in the art is well aware of which ingredients he selects and combines and in what quantities he uses them. For example, ethoxylated fatty acid amides can be added as a detergency booster.
- the washing, cleaning, aftertreatment or washing aids according to the invention are preferably liquid and contain water as the main solvent.
- a washing or cleaning agent is carried out by means of customary and known methods and processes.
- the ingredients may simply be mixed in stirred kettles, with water, the acidic components, if present, such as citric acid, and the nonionic surfactants, if present, conveniently presented.
- the further ingredients including the hydrogen peroxide and the aldehyde compound, preferably in portions, are added.
- the elemental silver or the silver compound is added.
- an aftertreatment agent according to the invention in the form of a fabric conditioner can be obtained by techniques familiar to the person skilled in the art for the preparation of fabric conditioners. This can be done for example by mixing the raw materials, optionally using high-shear mixing equipment. It is recommended to melt the cationic surfactants and subsequently dispersing the melt in a solvent, preferably water.
- Aldehyde compound can be integrated into the softener by simply adding. Again, the elemental silver or the silver compound is added as a last step.
- the aldehyde compound be contained in a perfume composition and added thereto to the compositions.
- Table 1 shows the compositions of a comparative formulation V1 and the compositions of five washing, cleaning, after-treatment or washing aids E1 to E5 according to the invention (all amounts are given in% by weight of active compound based on the composition):
- the perfume composition A contained, based on 1000 parts of the perfume composition, a total of 132 parts of 3- (4-tert-butylphenyl) isobutyraldehyde (Lilial), 35 parts of 2-methylundecanal (aldehyde C12 mna) and 6 parts of 4,6-dimethyl-3-cyclohexene.
- a first batch of laundry was washed with the comparative detergent V1 and a second batch of laundry with the detergent E1 according to the invention.
- the wet laundry was left in the washing machine for 6 hours after completion of the respective wash cycle and then evaluated by trained test persons.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL10707299T PL2408889T3 (en) | 2009-03-20 | 2010-03-10 | Detergent, cleaning agent, aftertreatment agent, or washing aid containing aldehydes and having an antibacterial effect |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009001688A DE102009001688A1 (en) | 2009-03-20 | 2009-03-20 | Aldehyde-containing washing, cleaning, aftertreatment or washing aid with antibacterial effect |
PCT/EP2010/053018 WO2010105949A1 (en) | 2009-03-20 | 2010-03-10 | Detergent, cleaning agent, aftertreatment agent, or washing aid containing aldehydes and having an antibacterial effect |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2408889A1 true EP2408889A1 (en) | 2012-01-25 |
EP2408889B1 EP2408889B1 (en) | 2012-12-26 |
Family
ID=42136265
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP10707299A Not-in-force EP2408889B1 (en) | 2009-03-20 | 2010-03-10 | Detergent, cleaning agent, aftertreatment agent, or washing aid containing aldehydes and having an antibacterial effect |
Country Status (6)
Country | Link |
---|---|
US (1) | US20120003326A1 (en) |
EP (1) | EP2408889B1 (en) |
DE (1) | DE102009001688A1 (en) |
ES (1) | ES2397913T3 (en) |
PL (1) | PL2408889T3 (en) |
WO (1) | WO2010105949A1 (en) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009045678A1 (en) * | 2009-10-14 | 2011-04-21 | Henkel Ag & Co. Kgaa | hygiene detergent |
WO2014200656A1 (en) | 2013-06-13 | 2014-12-18 | Danisco Us Inc. | Alpha-amylase from streptomyces umbrinus |
WO2014200657A1 (en) | 2013-06-13 | 2014-12-18 | Danisco Us Inc. | Alpha-amylase from streptomyces xiamenensis |
WO2014200658A1 (en) | 2013-06-13 | 2014-12-18 | Danisco Us Inc. | Alpha-amylase from promicromonospora vindobonensis |
WO2014204596A1 (en) | 2013-06-17 | 2014-12-24 | Danisco Us Inc. | Alpha-amylase from bacillaceae family member |
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US20160160199A1 (en) | 2013-10-03 | 2016-06-09 | Danisco Us Inc. | Alpha-amylases from exiguobacterium, and methods of use, thereof |
US20160186102A1 (en) | 2013-10-03 | 2016-06-30 | Danisco Us Inc. | Alpha-amylases from exiguobacterium, and methods of use, thereof |
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US10000881B2 (en) | 2013-12-06 | 2018-06-19 | Applied Silver, Inc. | Method for antimicrobial fabric application |
US20170050870A1 (en) | 2015-08-21 | 2017-02-23 | Applied Silver, Inc. | Systems And Processes For Treating Textiles With An Antimicrobial Agent |
WO2017084855A1 (en) * | 2015-11-18 | 2017-05-26 | Unilever N.V. | Method of improving personal hygiene |
WO2017084867A1 (en) * | 2015-11-18 | 2017-05-26 | Unilever N.V. | Method of improving personal hygiene |
WO2017173190A2 (en) | 2016-04-01 | 2017-10-05 | Danisco Us Inc. | Alpha-amylases, compositions & methods |
WO2017173324A2 (en) | 2016-04-01 | 2017-10-05 | Danisco Us Inc. | Alpha-amylases, compositions & methods |
WO2017197260A1 (en) | 2016-05-12 | 2017-11-16 | Applied Silver, Inc. | Articles and methods for dispensing metal ions into laundry systems |
US11622557B2 (en) | 2016-10-31 | 2023-04-11 | Applied Silver, Inc. | Dispensing of metal ions into batch laundry washers and dryers |
US10238116B2 (en) * | 2016-12-16 | 2019-03-26 | Dune Sciences, Inc. | Composite laundry additive |
WO2018160708A1 (en) | 2017-03-01 | 2018-09-07 | Applied Silver, Inc. | Systems and processes for treating textiles with an antimicrobial agent |
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DE632825C (en) * | 1931-11-28 | 1936-07-14 | Degussa | Process for the production of disinfecting soaps |
FR2728143A1 (en) * | 1994-12-16 | 1996-06-21 | Sodifra | AQUEOUS COMPOSITION BASED ON H2O2, ACIDS AND AG, PROCESS FOR PREPARATION AND USE IN THE FIELD OF DISINFECTION AND / OR HYGIENE |
US5972858A (en) * | 1998-02-18 | 1999-10-26 | Roche; Joseph M. | Grease cutting composition |
DE10312617A1 (en) * | 2003-03-21 | 2004-10-07 | Henkel Kgaa | Germ-reducing detergent or cleaning agent and process for its production |
US7462590B2 (en) * | 2005-02-25 | 2008-12-09 | Solutions Biomed, Llc | Aqueous disinfectants and sterilants comprising a peroxide/peracid/transition metal mixture |
US20090074881A1 (en) * | 2006-05-02 | 2009-03-19 | Bioneutral Laboratories Corporation Usa | Antimicrobial cidality formulations with residual efficacy, uses thereof, and the preparation thereof |
-
2009
- 2009-03-20 DE DE102009001688A patent/DE102009001688A1/en not_active Withdrawn
-
2010
- 2010-03-10 PL PL10707299T patent/PL2408889T3/en unknown
- 2010-03-10 ES ES10707299T patent/ES2397913T3/en active Active
- 2010-03-10 EP EP10707299A patent/EP2408889B1/en not_active Not-in-force
- 2010-03-10 WO PCT/EP2010/053018 patent/WO2010105949A1/en active Application Filing
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2011
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Also Published As
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WO2010105949A1 (en) | 2010-09-23 |
ES2397913T3 (en) | 2013-03-12 |
PL2408889T3 (en) | 2013-05-31 |
US20120003326A1 (en) | 2012-01-05 |
EP2408889B1 (en) | 2012-12-26 |
DE102009001688A1 (en) | 2010-09-23 |
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