EP2212465B1 - Agent de traitement de textiles biocide - Google Patents
Agent de traitement de textiles biocide Download PDFInfo
- Publication number
- EP2212465B1 EP2212465B1 EP08852385.7A EP08852385A EP2212465B1 EP 2212465 B1 EP2212465 B1 EP 2212465B1 EP 08852385 A EP08852385 A EP 08852385A EP 2212465 B1 EP2212465 B1 EP 2212465B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- treatment agent
- textile treatment
- biocidal
- quaternary ammonium
- textile
- 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.)
- Active
Links
- 239000004753 textile Substances 0.000 title claims description 96
- 230000003115 biocidal effect Effects 0.000 title claims description 43
- 239000003795 chemical substances by application Substances 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 60
- 239000002736 nonionic surfactant Substances 0.000 claims description 43
- 239000004744 fabric Substances 0.000 claims description 37
- 239000002304 perfume Substances 0.000 claims description 36
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000002191 fatty alcohols Chemical class 0.000 claims description 13
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 10
- 239000002979 fabric softener Substances 0.000 claims description 8
- 244000005700 microbiome Species 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 8
- 235000019270 ammonium chloride Nutrition 0.000 claims 4
- 125000000524 functional group Chemical group 0.000 claims 3
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- 238000012546 transfer Methods 0.000 description 9
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- 231100000027 toxicology Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- HFTAFOQKODTIJY-UHFFFAOYSA-N umbelliferone Natural products Cc1cc2C=CC(=O)Oc2cc1OCC=CC(C)(C)O HFTAFOQKODTIJY-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000003253 viricidal effect Effects 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000011276 wood tar Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 239000001841 zingiber officinale Substances 0.000 description 1
Classifications
-
- 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
- D06M13/005—Compositions containing perfumes; Compositions containing deodorants
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- 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
-
- 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
-
- 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
- D06M13/10—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 oxygen
- D06M13/165—Ethers
- D06M13/17—Polyoxyalkyleneglycol ethers
-
- 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
- D06M13/46—Compounds containing quaternary nitrogen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
Definitions
- the invention relates to a textile treatment composition containing a specific biocidal compound, a perfume composition and a nonionic surfactant in an amount between 0.75 and 1.5 wt .-%, wherein the nonionic surfactant has an HLB value between 10.5 and 15 and a turbidity temperature of at least 50 ° C.
- the invention also relates to the use of the textile treatment agent and a process for its preparation.
- adhesion of microorganisms to surfaces is undesirable, especially in pathogenic microorganisms.
- Adherent microorganisms often lead to infections or reinfection in humans, animals and plants.
- contaminated textiles can not be sterilized to the required extent by the changed washing behavior with viruses, bacteria, mold or yeast fungi, so that under certain circumstances a (re-) infection can occur during renewed contact of the consumer with the supposedly pure laundry.
- Antimicrobially active compositions and their use in detergents or cleaners are known in the art. These are, for example, textile treatment agents which contain one or more biocidal agents and are added to the rinse cycle.
- biocidal compounds used or their commercially available forms on offer often have a pungent odor, the consumer on the product itself, but also on the treated textiles, often negative.
- the addition of a perfume composition leads to unstable products, especially at low storage temperatures.
- the international application WO 99/55813 A1 describes a fabric treatment composition containing a perfume, a biocidal agent and a surfactant, but these fabric treatment agents are not storage stable, unlike the compositions of the present invention.
- It is therefore an object of the present invention to provide a stable fabric treatment composition comprising a biocidal compound and a perfume composition.
- nonionic surfactant in an amount between 0.75 and 1.5 wt .-%, which has an HLB value (according to Griffin) between 10.5 and 15 and a certain turbidity temperature of at least 50 ° C ( determined according to DIN 53917), can effectively stabilize a textile treatment agent containing a particular biocidal, quaternary ammonium compound and a perfume composition. It has been found that stabilization does not occur when the nonionic surfactant has only one of the two properties.
- nonionic surfactant have an HLB value (according to Griffin) between 11 and 14, and more preferably between 11 and 13.
- Nonionic surfactants having an HLB value (according to Griffin) in this range and a clouding temperature of at least 50 ° C. (determined according to DIN 53917) stabilize textile treatment agents with a particular biocidal, quaternary ammonium compound and a perfume composition particularly effectively.
- the nonionic surfactant is an alkoxylated fatty alcohol. Most preferably, the nonionic surfactant is an ethoxylated and / or propoxylated C 12 -C 18 fatty alcohol.
- alkoxylated fatty alcohols are widely available commercially, and thus are also inexpensive in many cases.
- the ratio of nonionic surfactant to perfume is greater than or equal to 5: 1. It is more preferred that the ratio of nonionic surfactant to perfume be greater than 6: 1, more preferably between 15: 1 and 8: 1, and even more preferably between 12: 1 and 9: 1.
- Particularly advantageous textile treatment agents are obtained when the ratio of nonionic surfactant to perfume composition is within a certain range.
- the textile treatment agents obtained are sufficiently stable, but have no unfavorable foaming behavior.
- the textile treatment agent is selected from the group consisting of fabric conditioners, washing auxiliaries and aftertreatment agents.
- the fabric treatment agent is a softener
- the softening component is an alkylated quaternary ammonium compound wherein at least one alkyl chain is interrupted by an ester or amido group.
- Fabric softeners and aftertreatment agents are preferred as textile treatment agents since they come into contact with the textiles only in the last step of a conventional textile washing process, the rinse cycle.
- the biocidal compound is selected from the group consisting of quaternary ammonium compounds.
- biocidal compounds are effective against viruses, bacteria, mold or yeasts.
- the textile treatment agent additionally contains 0.5 to 5, preferably 1 to 2.5 wt .-%, of ethanol and / or isopropanol.
- Ethanol and isopropanol themselves have an antimicrobial effect and thus extend the spectrum of action of the textile treatment agent. In addition, they also act as an emulsifier for the perfume and assist the nonionic surfactant in stabilizing the fabric treatment agent.
- the invention further relates to the use of the textile treatment agent according to the invention for reducing the number of microorganisms on textile fabrics treated therewith.
- the invention also relates to the use of the textile treatment agent according to the invention for reducing the number of microorganisms in a washing or rinsing liquor.
- a biocidal compound is understood as meaning compounds which have an antimicrobial effect and reduce the number of microorganisms on textile fabrics treated therewith and in the rinsing liquor.
- biocidal compounds are differentiated according to bacteriostats and bactericides, fungistats and fungicides.
- Suitable biocidal compounds are preferably selected from the group of quaternary ammonium compounds.
- the biocidal compound is a quaternary ammonium compound.
- the suitable as biocidal agents quaternary ammonium compounds (QAC) have the general formula (R 1 ) (R 2 ) (R 3 ) (R 4 ) N + X - , in which R 1 to R 4 identical or different C 1 -C 22 -alkyl radicals, C 7 -C 28 -aralkyl radicals or heterocyclic radicals, where two or, in the case of an aromatic inclusion as in pyridine, even three radicals together with the nitrogen atom form the heterocycle, for example a pyridinium or imidazolinium compound, and Halide ions, sulfate ions, hydroxide ions or similar anions.
- QACs can be prepared by reacting tertiary amines with alkylating agents, such as, for example, methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
- alkylating agents such as, for example, methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
- alkylating agents such as, for example, methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
- alkylating agents such as, for example, methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
- the alkylation of tertiary amines with a long alkyl radical and two methyl groups succeeds particularly easily, and the quaternization of tertiary
- Suitable QACs are, for example, benzalkonium chloride (N-alkyl-N, N-dimethylbenzyl-ammonium chloride, CAS No. 8001-54-5), benzalkone B ( m, p -dichlorobenzyl-dimethyl-C 12 -alkylammonium chloride, CAS No. 58390 -78-6), benzoxonium chloride (benzyldodecyl-bis (2-hydroxyethyl) ammonium chloride), cetrimonium bromide (N-hexadecyl-N, N, N-trimethyl-ammonium bromide, CAS No.
- benzalkonium chloride N-alkyl-N, N-dimethylbenzyl-ammonium chloride, CAS No. 8001-54-5
- benzalkone B m, p -dichlorobenzyl-dimethyl-C 12 -alkylammonium chloride, CAS
- Benzetonium chloride N, N-dimethyl-N- [2- [2- [p- (1,1,3,3-tetramethylbutyl) phenoxy] ethoxy] ethyl] benzyl ammonium chloride, CAS No. 121-54-0
- dialkyldimethylammonium chlorides such as di-n-decyl dimethyl ammonium chloride (CAS No. 7173-51-5-5), didecyldimethylammonium bromide (CAS No. 2390-68-3), dioctyl, 1-cetylpyridinium chloride (CAS No. 123-03- 5) and thiazoline iodide (CAS No.
- QACs are dialkyldimethylammonium chlorides, in particular di-n-decyldimethylammonium chloride, N-octadecyl-N, N, N-trimethylammonium chloride, N-hexadecyl-N, N, N-trimethylammonium chloride and the benzalkonium chlorides having C 8 -C 18 -alkyl radicals, in particular C 12 -C 14 -alkylbenzyl-dimethylammonium chloride.
- Another preferred biocidal compound is methyl N- (2-hydroxyethyl) -N, N-di (caprocyloxyethyl) ammonium methosulfate.
- these biocidal compounds act effectively against numerous microorganisms, the cationic compounds attract particularly well on cotton-containing fabrics and blended fabrics.
- dialkyldimethylammonium halides the benzalkonium halides and / or substituted benzalkonium halides are, for example, commercially available as Barquat® ex Lonza, Marquat® ex Mason, Variquat® ex Evonik Industries and Hyamine® ex Lonza.
- the biocidal quaternary ammonium compound is used in an amount of from 0.1% to 20%, preferably from 0.5% to 10%, and most preferably from 1% to 5% % By weight used. It is particularly preferred from a toxicological and ecological point of view that the amount of biocidal compound is less than 2.5% by weight.
- the textile treatment agent necessarily contains a perfume composition in order to impart a pleasant fragrance to the laundry treated therewith and to the textile treatment agent itself.
- the textile treatment composition contains the perfume composition in an amount of usually up to 2 wt .-%, preferably 0.01 to 1 wt .-%, in particular 0.02 to 0.75 wt .-% and particularly preferably 0.04 to 0.4% by weight.
- the perfume composition may contain individual perfume compounds, for example the synthetic products of the ester type, ethers, aldehydes, ketones, alcohols and hydrocarbons. Preferably, however, mixtures of different fragrances are used, which together produce an attractive fragrance.
- the perfume composition may also contain natural fragrance compounds as are available from plant sources.
- the perfume composition of the fabric treatment agent may further contain at least one aromatherapy component.
- an aromatherapy component an essential oil is preferably used.
- essential oils are extracted from flowers, spices, herbs, woods or fibers and are complex mixtures of various organic molecules such as terpenes, ethers, coumarins, esters, aldehydes, phenyl esters, monoterpenols, phenols, monoterpenes, oxides, sesquiterpene ketones, sesquiterpenes and sesquiterpenols. Due to their small molecular structure, essential oils pass through the skin and / or the mucous membrane into the bloodstream and tissue. In this way they can influence the entire organism.
- essential oils can be used in the textile treatment agents according to the invention.
- suitable essential oils include, for example, oils of Abies Sibirica, Amyris balsamifera, anise (Illicium verum), lemon balm (Melissa officinalis), basil (Ocimum basilicum), pimenta acre, bee balm (Monarda didyma), bergamot (citrus aurantium bergamia), birch (betula Aba) Bitter Orange (Citrus Aurantium Amara), Hibiscus, Hundred-leaved Rose (Rosa Centifolia), Calendula Officinalis, Californian Nusseibe (Torreya Californica), Camellia Sinensis, Capsicum Frutescers Oleoresin, Caraway (Carum Carvi), Cardamom (Elettaria Cardamomum), Cedarwood (Cedrus Atlantica) , Chamaecyparis obtus
- the textile treatment agent contains as a further essential component a nonionic surfactant having an HLB value (according to Griffin) between 10.5 and 15 and a clouding temperature of at least 50 ° C. (determined according to DIN 53917) in an amount between 0.75 and 1.5% by weight. ,
- HLB value hydrophilic-lipophilic-balance abbreviation
- the factor 20 is a scaling factor selected by Griffin freely. As a rule, this results in a scale of 1 to 20.
- An HLB value of 1 indicates a lipophilic compound, a chemical compound with an HLB value of 20 has a high hydrophilic content.
- the clouding temperature is the temperature at which an aqueous solution of a surfactant suddenly becomes cloudy on heating. The determination is made according to DIN 53917.
- the turbidity temperature is determined from a 1% aqueous solution. At very high degree of alkoxylation, the determination of the turbidity temperature in a NaCl solution must be carried out.
- nonionic surfactants having an HLB value (according to Griffin) between 10.5 and 15 and a turbidity temperature of at least 50 ° C are preferably alkoxylated, advantageously ethoxylated, in particular primary alcohols having preferably 8 to 18 carbon atoms and used on average 3 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 contain linear and methyl-branched radicals in the mixture.
- alcohol ethoxylates with linear radicals of alcohols of native origin having 12 to 18 carbon atoms, for example coconut, palm, tallow or oleyl alcohol, and on average 4 to 8 EO per mole of alcohol are preferred.
- 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 range ethoxylates, NRE).
- a particularly preferred nonionic surfactant is a C 12-18 alcohol with 7 EO.
- This ethoxylated fatty alcohol has an HLB of 11.9 and a haze temperature in the range of 50 to 56 ° C.
- the amount of nonionic surfactant having an HLB value (according to Griffin) of between 10.5 and 15 and a clouding temperature of at least 50 ° C (determined according to DIN 53917) is in a textile treatment agent between 0.75 and 1.5 wt .-%.
- a nonionic surfactant having an HLB value (according to Griffin) between 10.5 and 15 and a clouding temperature of at least 50 ° C (determined according to DIN 53917) is able to stabilize a perfumed, biocidal textile treatment agent so effectively that it can in low , absolute amount can be used. This has the advantage that the risk is low that forms in the rinse by the presence of the foam-forming nonionic surfactants too much foam, which remains on the laundry.
- the ratio of nonionic surfactant to perfume is greater than or equal to 5: 1, preferably greater than 6: 1, more preferably between 15: 1 and 8: 1 and particularly preferably between 12: 1 and 9: 1.
- the fabric treatment agents may contain other ingredients that further enhance the performance and / or aesthetics of the fabric treatment composition.
- preferred textile treatment agents additionally contain one or more substances from the group of softening components, thickeners, builders, electrolytes, nonaqueous solvents, pH adjusters, fluorescers, dyes, hydrotopes, foam inhibitors, silicone oils, anti redeposition agents, optical brighteners, grayness inhibitors, Anti-shrinkage agents, anti-wrinkling agents, color transfer inhibitors, antioxidants, preservatives, corrosion inhibitors, antistatic agents, bittering agents, ironing auxiliaries, repellents and impregnating agents, swelling and anti-slip agents, skin care compounds and UV absorbers.
- fabric softening conditioners in addition to the biocidal, quaternary ammonium compound, nonionic surfactant and perfume composition contain a softening component.
- the softening component includes, 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 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) and (II): wherein in (I) 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 R or R 1 or are an aromatic radical , X- represents either a halide, methosulfate, methophosphate or phosphate ion, as well as 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
- 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 can each independently be 1, 2 or 3.
- X - may be either a halide, methosulfate, methophosphate or phosphate ion as well as mixtures of these anions.
- R 5 represents the group O (CO) R 7 .
- R 5 is the group O (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.
- Examples of compounds of the formula (I) are methyl N- (2-hydroxyethyl) -N, N-di (tallow acyloxyethyl) ammonium methosulfate, bis (palmitoyloxyethyl) hydroxyethyl methyl ammonium methosulfate, 1,2-bis - [tallowloxy] -3-trimethylammonium propane chloride or methyl N, N-bis (stearoyloxyethyl) -N- (2-hydroxyethyl) ammonium methosulphate.
- the acyl groups are preferred whose corresponding fatty acids have an iodine number between 1 and 100, preferably between 5 and 80, more preferably between 10 and 60 and in particular between 15 and 45 and which have a cis / trans isomer ratio (in% by weight) of greater than 30:70, preferably greater than 50:50 and in particular equal to or greater than 60:40.
- Stepan under the tradename Stepantex ® methylhydroxyalkyldialkoyloxyalkylammonium or those known under Dehyquart ® Cognis products, known under Rewoquat ® products from Degussa or those known under Tetranyl® products of Kao.
- Further preferred compounds are the diester quats of the formula (III) which are obtainable under the name Rewoquat® W 222 LM or CR 3099.
- R 21 and R 22 are each independently an aliphatic radical having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds.
- ester group O (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.
- q can take integer values between 1 and 4.
- plasticizing compounds are described by formula (V), wherein R 12 , R 13 and R 14 independently represent a C 1-4 alkyl, alkenyl or hydroxyalkyl group, R 15 and R 16 each independently represent a C 8-28 alkyl group, X- is an anion and r is a number between 0 and 5.
- a preferred example of a cationic deposition aid according to formula (V) is 2,3-bis [tallowacyloxy] -3-trimethylammoniumpropane chloride.
- plasticizing components which can be used according to the invention are quaternized protein hydrolyzates or protonated amines.
- cationic polymers are also suitable softening component.
- Suitable cationic polymers include the polyquaternium polymers as described in the CTFA Cosmetic Ingredient Dictionary (The Cosmetic, Toiletry and Fragrance, Inc., 1997), in particular the Polyquaternium-6, Polyquaternium-7, Polyquaternium, also referred to as Merquats.
- polymers Polymer JR, LR and KG series from Amerchol
- polyquaternium-4 copolymers such as graft copolymers having a cellulose backbone and quaternary ammonium groups attached via allyl dimethyl ammonium chloride, cationic cellulose derivatives such as cationic guar such as guar hydroxypropyl triammonium chloride, and similar quaternized guar Derivatives (eg Cosmedia Guar from Cognis or the Jaguar series from Rhodia), cationic quaternary sugar derivatives (cationic alkyl polyglucosides), eg the commercial product Glucquat® 100, according to CTFA nomenclature a "Lauryl Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride", copolymers of PVP and dimethylaminomethacrylate, copolymers of vinylimidazole and vinylpyrrolidone, amine osilicon polymers and copolymers.
- polyquaternized polymers e.g., Luviquat® Care from BASF
- chitin-based cationic biopolymers and their derivatives for example, the polymer available under the trade name Chitosan® (manufacturer: Cognis).
- Some of the cited cationic polymers additionally have skin and / or textile care properties.
- R 17 can be an aliphatic alk (en) yl radical having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds. s can take values between 0 and 5.
- R 18 and R 19 are each independently H, C 1-4 alkyl or hydroxyalkyl and X - is an anion.
- softening components include protonated or quaternized polyamines.
- plasticizing components are alkylated quaternary ammonium compounds of which at least one alkyl chain is interrupted by an ester group and / or amido group.
- alkylated quaternary ammonium compounds of which at least one alkyl chain is interrupted by an ester group and / or amido group.
- Very particular preference is given to N-methyl-N- (2-hydroxyethyl) -N, N- (ditallowacyloxyethyl) ammonium methosulfate or bis (palmitoyloxyethyl) -hydroxyethyl-methylammonium methosulfate.
- the softening component is in amounts of from 0.1 to 80% by weight, usually from 1 to 40% by weight, preferably from 2 to 20% by weight and in particular from 3 to 15% by weight, in each case based on the entire textile treatment agent.
- Builders which may be present in the textile treatment agents include, in particular, carbonates and salts of organic di- and polycarboxylic acids and mixtures of these substances.
- the latter include, for example, polyacrylates and acrylic acid / maleic acid copolymers, polyaspartates and monomeric polycarboxylates such as citrates, gluconates, succinates or malonates, which are preferably used as sodium salts.
- the fabric treatment agent may contain a thickener.
- the thickener may include, for example, a polyacrylate thickener, xanthan gum, gellan gum, guar gum, alginate, carrageenan, carboxymethyl cellulose, bentonites, wellan gum, locust bean gum, agar-agar, tragacanth, gum arabic, pectins, polyoses, starch, dextrins, gelatin and casein include.
- modified natural products such as modified starches and celluloses, for example, carboxymethylcellulose and Other cellulose ethers, called hydroxyethyl and propyl cellulose and gum ethers, can be used as thickening agents.
- polyacrylic and polymethacrylic thickeners include the high molecular weight homopolymers of acrylic acid crosslinked with a polyalkenyl polyether, in particular an allyl ether of sucrose, pentaerythritol or propylene (INCI name according to the International Dictionary of Cosmetic Ingredients of The Cosmetic, Toiletry and Fragrance Association (CTFA) ": carbomer), also referred to as carboxyvinyl polymers.
- CFA Cosmetic, Toiletry and Fragrance Association
- Such polyacrylic acids are available, inter alia, from 3V Sigma under the trade name Polygel®, for example Polygel DA, and from BF Goodrich under the trade name Carbopol®, for example Carbopol 940 (molecular weight about 4,000,000), Carbopol 941 (molecular weight about 1,250,000) or Carbopol 934 (molecular weight about 3,000,000).
- acrylic acid copolymers are included: (i) Copolymers of two or more monomers from the group of acrylic acid, methacrylic acid and their simple ester, preferably formed with C 1-4 -alkanols (INCI acrylates copolymer), such as the copolymers of methacrylic acid, butyl acrylate and methyl methacrylate (CAS designation according to Chemical Abstracts Service: 25035-69-2) or of butyl acrylate and methyl methacrylate (CAS 25852-37-3) and the example of Rohm & Haas under the trade name Aculyn® and Acusol®, as well as from Degussa (Goldschmidt) under the trade name Tego® Polymer, for example the anionic non-associative polymers Aculyn 22, Aculyn 28, Aculyn 33 (cross-linked), Acusol 810, Acusol 820, Acusol 823 and Acusol 830 (CAS 25852-37-3); (ii) cross-linked),
- Carbopol® eg the hydrophobic Carbopol ETD 2623 and Carbopol 1382 (INCI Acrylates / C 10 -30 alkyl acrylate crosspolymer) and Carbopol Aqua 30 (former Carbopol EX 473).
- Carbopol® eg the hydrophobic Carbopol ETD 2623 and Carbopol 1382 (INCI Acrylates / C 10 -30 alkyl acrylate crosspolymer) and Carbopol Aqua 30 (former Carbopol EX 473).
- Particular preference is given to using cationic poly (meth) acrylic thickeners.
- Preferred textile treatment agents contain from 0.01 to 3 wt .-% and preferably 0.1 to 1 wt .-% thickening agent based on the total fabric treatment agent.
- the amount of thickener used depends on the type of thickener and the desired degree of thickening.
- electrolytes from the group of inorganic salts a wide number of different salts can be used.
- Preferred cations are the alkali and alkaline earth metals, preferred anions are the halides and sulfates.
- the use of NaCl or MgCl 2 in the textile treatment agents is preferred.
- the proportion of electrolytes in the textile treatment agent is usually 0.01 to 2 wt .-%.
- Non-aqueous solvents that can be used in the textile treatment compositions, for example, from the group of monohydric or polyhydric alcohols, alkanolamines or glycol ethers, provided they are miscible in the specified concentration range with water.
- the solvents are selected from ethanol, n- or i-propanol, butanols, glycol, propane or butanediol, glycerol, diglycol, propyl or butyldiglycol, hexylene glycol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether Propylene glycol methyl, ethyl or propyl ether, dipropylene glycol monomethyl or ethyl ether, di-isopropylene glycol monomethyl or ethyl
- the textile treatment agent additionally contains 0.5 to 5 wt .-%, preferably 1 to 2.5 wt .-% ethanol and / or isopropanol.
- Ethanol and isopropanol not only support the stabilization of the perfume composition, but also have a biocidal effect themselves. Thus, not only the stability of the textile treatment agent is improved, but also extends the spectrum of action of the textile treatment agent.
- the viscosity of the textile treatment agents can be measured by conventional standard methods (for example Brookfield LVT-II viscosimeter at 20 rpm and 20 ° C., spindle 2) and is preferably 5 to 4000 mPas, with values between 10 and 2000 mPas being particularly preferred , Most preferably, the viscosity of fabric softeners is from 10 to 1000 mPas.
- pH adjusters In order to bring the pH of the textile treatment agent in the desired range, the use of pH adjusters may be indicated.
- Can be used here are all known acids or alkalis, unless their use is not for technical application or environmental reasons or for reasons of consumer protection prohibited.
- the textile treatment agents can be dyed with suitable dyes.
- Preferred dyes the selection of which presents no difficulty to the skilled person, have a high storage stability and insensitivity to the other ingredients of the textile treatment agents and to light and no pronounced substantivity to textile fibers so as not to stain them.
- Suitable foam inhibitors which can be used in the textile treatment compositions are, for example, soaps, paraffins or silicone oils, which may optionally be applied to support materials.
- Suitable soil release polymers also referred to as "anti-redeposition agents" include, for example, nonionic cellulose ethers such as methyl cellulose and methyl hydroxypropyl cellulose having a methoxy group content of 15 to 30 wt% and hydroxypropyl groups of 1 to 15 wt%, respectively based on the nonionic cellulose ether and the known from the prior art polymers of phthalic acid and / or terephthalic acid or derivatives thereof, in particular polymers of ethylene terephthalates and / or polyethylene and / or polypropylene glycol terephthalates or anionic and / or nonionic modified derivatives thereof.
- Suitable derivatives include the sulfonated derivatives of the phthalic and terephthalic acid polymers.
- Optical brighteners can be added to the textile treatment agents to eliminate graying and yellowing of the treated textile fabrics. These fabrics impinge on the fiber and cause whitening and bleaching by transforming invisible ultraviolet radiation into visible longer wavelength light, emitting the ultraviolet light absorbed from the sunlight as faint bluish fluorescence, and pure with the yellowness of the grayed or yellowed wash White results.
- Suitable compounds are derived, for example, from the substance classes of 4,4'-diamino-2,2'-stilbenedisulfonic acids (flavonic acids), 4,4'-distyrylbiphenyls, methylumbelliferones, coumarins, dihydroquinolinones, 1,3-diarylpyrazolines, naphthalimides, benzoxazole , Benzisoxazole and benzimidazole systems as well as heterocyclic substituted pyrene derivatives.
- the optical brighteners are usually used in amounts of between 0% and 0.3% by weight, based on the finished detergent and cleaner.
- Grayness inhibitors have the task of keeping the dirt detached from the fiber suspended in the liquor and thus preventing the dirt from being rebuilt.
- Water-soluble colloids of mostly organic nature are suitable for this purpose, for example glue, gelatine, salts of ether sulfonic acids or cellulose or salts of acidic sulfuric acid esters of cellulose or starch.
- water-soluble polyamides containing acidic groups are suitable for this purpose. It is also possible to use soluble starch preparations and starch products other than those mentioned above, for example degraded starch, aldehyde starches, etc. Polyvinylpyrrolidone is also useful.
- cellulose ethers such as carboxymethylcellulose (Na salt), methylcellulose, hydroxyalkylcellulose and mixed ethers such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose and mixtures thereof in amounts of from 0.1 to 5% by weight, based on the textile treatment agents.
- the fabric treatment agent may contain a dye transfer inhibitor.
- the dye transfer inhibitor is a polymer or copolymer of cyclic amines such as vinylpyrrolidone and / or vinylimidazole.
- Suitable color transfer inhibiting polymers include polyvinylpyrrolidone (PVP), polyvinylimidazole (PVI), copolymers of vinylpyrrolidone and vinylimidazole (PVP / PVI), polyvinylpyridine-N-oxide, poly-N-carboxymethyl-4-vinylpyridium chloride, and mixtures thereof.
- polyvinylpyrrolidone PVP
- polyvinylimidazole PVI
- copolymers of vinylpyrrolidone and vinylimidazole PVP / PVI
- the polyvinylpyrrolidones (PVP) used preferably have an average molecular weight of 2,500 to 400,000 and are commercially available from ISP Chemicals as PVP K 15, PVP K 30, PVP K 60 or PVP K 90 or from BASF as Sokalan® HP 50 or Sokalan® HP 53 available.
- the copolymers of vinylpyrrolidone and vinylimidazole (PVP / PVI) used preferably have a molecular weight in the range from 5,000 to 100,000.
- a PVP / PVI copolymer for example from BASF under the name Sokalan® HP 56th
- the amount of dye transfer inhibitor based on the total amount of the fabric treatment agent is preferably from 0.01 to 2% by weight, preferably from 0.05 to 1% by weight, and more preferably from 0.1 to 0.5% by weight.
- the detergents and cleaners may contain antioxidants.
- This class of compounds includes, for example, substituted phenols, hydroquinones, catechols and aromatic amines, as well as organic sulfides, polysulfides, dithiocarbamates, phosphites, phosphonates and vitamin E.
- Antistatic agents increase the surface conductivity and thus allow an improved drainage of formed charges.
- External antistatic agents are generally substances with at least one hydrophilic molecule ligand and give a more or less hygroscopic film on the surfaces. These mostly surface-active antistatic agents can be subdivided into nitrogen-containing (amines, amides, quaternary ammonium compounds), phosphorus-containing (phosphoric acid esters) and sulfur-containing (alkyl sulfonates, alkyl sulfates) antistatic agents.
- Lauryl (or stearyl) dimethylbenzylammonium chlorides are suitable as antistatics for textile fabrics or as an additive to textile treatment agents, wherein additionally a softening effect is achieved.
- silicone derivatives can be used in the fabric treatment agents. These additionally improve the rinsing behavior of the detergents and cleaning agents by their foam-inhibiting properties.
- Preferred silicone derivatives are, for example, polydialkyl or alkylaryl siloxanes in which the alkyl groups have one to five carbon atoms and are completely or partially fluorinated.
- Preferred silicones are polydimethylsiloxanes, which may optionally be derivatized and are then amino-functional or quaternized or have Si-OH, Si-H and / or Si-Cl bonds.
- the textile treatment agent may comprise a skin care compound.
- a skin-care compound is understood to mean a compound or a mixture of compounds which, on contact of a textile with the detergent, draw on the textile and give an advantage on contact of the textile with skin of the skin compared to a textile which is not treated with the textile treatment agent according to the invention has been.
- This benefit may include, for example, the transfer of the skin care compound from the textile to the skin, less water transfer from the skin to the textile, or less friction on the skin surface through the textile.
- the amount of skin-care compound is preferably between 0.01 and 10 wt .-%, preferably between 0.1 and 5 wt .-% and most preferably between 0.3 and 3 wt .-% based on the fabric treatment agent.
- the textile treatment agents may also contain UV absorbers which are applied to the treated fabrics and improve the light fastness of the fibers.
- Compounds having these desired properties are, for example, those by non-radiative deactivation effective compounds and derivatives of benzophenone with substituents in the 2- and / or 4-position.
- Also suitable are substituted benzotriazoles, phenyl-substituted acrylates (cinnamic acid derivatives) in the 3-position, optionally with cyano groups in the 2-position, salicylates, organic Ni complexes and natural substances such as umbelliferone and the body's own urocanic acid.
- the preparation of the textile treatment agents can be obtained by techniques familiar to the person skilled in the art for the preparation of fabric softeners, washing auxiliaries and after-treatment agents. This can be done for example by mixing the raw materials, optionally using high-shear mixing equipment.
- fabric softeners as textile treatment agents, it is recommended to melt the softening component (s) and subsequently to disperse the melt in a solvent, preferably water.
- the other ingredients can be integrated into the softener by simply adding.
- Table 2 shows the HLB values (according to Griffin) and clouding temperatures (determined according to DIN 53917) of the nonionic surfactants used.
- Table 2 Nonionic surfactant HLB value Cloud point [° C] C 12-18 fatty alcohol with 7 EO 11.9 50 - 56 *** C 12-18 fatty alcohol with 5 EO 10.3 - C 13-15 oxofatty alcohol with 7 EO 11.8 43 *** hydrogenated castor oil with 40 EO ** 17.1 76 - 82 **** ** Eumulgin HRE 40 (ex Cognis) *** 1% in H 2 O **** 1% in 5% NaCl solution
- the textile treatment agents E1 to E6 according to the invention were clear or stable at a storage temperature of 0 ° C. for 4 weeks.
- the textile treatment agent E3 according to the invention has been subjected to several microbiological tests:
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- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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Claims (13)
- Agent de traitement de textile comprenant un composé ammonium quaternaire biocide, une composition de parfum et un tensioactif non ionique, le tensioactif non ionique ayant une valeur HLB (selon Griffin) comprise entre 10,5 et 15 et une température de turbidité d'au moins 50°C (déterminée selon la norme DIN 53917) et étant présent dans une quantité comprise entre 0,75 et 1,5% en poids et le composé ammonium quaternaire biocide est(i) un chlorure dialkyldiméthylammonium ou(ii) un chlorure de benzalkonium comportant des radicaux alkyle en C8 à C18.
- Agent de traitement de textile selon la revendication 1, caractérisé en ce que le tensioactif non ionique est un alcool gras alcoxylé.
- Agent de traitement de textile selon l'une des revendications 1 ou 2, caractérisé en ce que le tensio-actif non ionique est un alcool gras en C12 à C18 éthoxylé et/ou propoxylé.
- Agent de traitement de textile selon l'une des revendications 1 à 3, caractérisé en ce que le rapport tensioactif non ionique sur le parfum est supérieur ou égal à 5:1.
- Agent de traitement de textile selon la revendication 4, caractérisé en ce que le rapport tensioactif non ionique sur parfum est supérieur à 6:1, de préférence entre 15:1 et 8:1 1 et plus préférablement entre 12:1 et 9:1.
- Agent de traitement de textile selon la revendication 1, caractérisé en ce que l'agent de traitement de textile est un assouplissant et contient un composant adoucissant.
- Agent de traitement de textile selon la revendication 6, caractérisé en ce que le composant adoucissant est un composé ammonium quaternaire alkylé, au moins une chaîne alkyle étant interrompue par un groupe ester ou amido.
- Agent de traitement de textile selon la revendication 1, caractérisé en ce que l'agent de traitement de textile contient en outre entre 0,5 et 5% en poids, de préférence de 1 à 2,5% d'éthanol et/ou d'isopropanol.
- Utilisation de l'agent de traitement de textile selon l'une des revendications 1 à 8, pour réduire le nombre de microorganismes sur des tissus traités avec ledit agent.
- Utilisation de l'agent de traitement de textile selon l'une des revendications 1 à 8 pour réduire le nombre de microorganismes dans un bain de rinçage ou de lavage.
- Utilisation d'un tensioactif non ionique ayant une valeur HLB (selon Griffin) de 10,5 à 15 et une température de turbidité d'au moins 50°C (déterminée selon la norme DIN 53917) dans une quantité comprise entre 0,75 et 1,5% en poids pour la stabilisation d'un agent de traitement de textile qui contient un composé d'ammonium quaternaire biocide et une composition de parfum, ledit composé ammonium quaternaire biocide étant(i) un chlorure de dialkyldiméthylammonium, ou(ii) un chlorure de benzalkonium comportant des radicaux alkyle en C8 à C18.
- Utilisation d'un agent tensio-actif non ionique ayant une valeur HLB (selon Griffin) de 10,5 à 15 et une température de turbidité d'au moins 50°C (déterminée selon la norme DIN 53917) dans une quantité comprise entre 0,75 et 1,5% en poids pour la stabilisation d'un agent de traitement de textile qui contient un composé ammonium quaternaire biocide et une composition de parfum, le composé ammonium quaternaire biocide étant(i) un chlorure de dialkyldiméthylammonium, ou(ii) un chlorure de benzalkonium comportant des radicaux alkyle en C8 à C18,
lors du stockage de l'agent de traitement de textile à 0°C à 10°C. - Procédé de production d'un agent de traitement de textile limpide comprenant un composé ammonium quaternaire biocide et une composition de parfum, le composé ammonium quaternaire biocide étant(i) un chlorure de dialkyldiméthylammonium, ou(ii) un chlorure de benzalkonium comportant des radicaux alkyle en C8 à C18,
dans lequel on ajoute un tensioactif non ionique ayant une valeur HLB (selon Griffin) de 10,5 à 15 et une température de turbidité d'au moins 50°C (déterminée selon la norme DIN 53917) dans une quantité comprise entre 0,75 et 1,5% en poids.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102007056936A DE102007056936A1 (de) | 2007-11-23 | 2007-11-23 | Biozides Textilbehandlungsmittel |
PCT/EP2008/065741 WO2009065823A2 (fr) | 2007-11-23 | 2008-11-18 | Agent de traitement de textiles biocide |
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EP2212465A2 EP2212465A2 (fr) | 2010-08-04 |
EP2212465B1 true EP2212465B1 (fr) | 2016-06-22 |
EP2212465B2 EP2212465B2 (fr) | 2019-12-25 |
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EP08852385.7A Active EP2212465B2 (fr) | 2007-11-23 | 2008-11-18 | Agent de traitement de textiles biocide |
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US (1) | US8143207B2 (fr) |
EP (1) | EP2212465B2 (fr) |
DE (1) | DE102007056936A1 (fr) |
WO (1) | WO2009065823A2 (fr) |
Families Citing this family (10)
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DE102010043066A1 (de) | 2010-10-28 | 2012-05-03 | Henkel Ag & Co. Kgaa | Wasch- oder Reinigungsmittel mit antimikrobieller Wirkung |
US9439421B2 (en) | 2011-08-04 | 2016-09-13 | University Of Georgia Research Foundation, Inc. | Permanent attachment of ammonium and guanidine-based antimicrobials to surfaces containing -OH functionality |
EP2838982B9 (fr) | 2012-04-17 | 2017-06-14 | Unilever PLC | Améliorations relatives à des conditionneurs de tissus |
WO2014026859A1 (fr) * | 2012-08-13 | 2014-02-20 | Henkel Ag & Co. Kgaa | Agent liquide épaissi de traitement de surface textile ou dure |
US10252945B2 (en) | 2012-09-26 | 2019-04-09 | Multiple Energy Technologies Llc | Bioceramic compositions |
WO2014067783A1 (fr) * | 2012-10-31 | 2014-05-08 | Henkel Ag & Co. Kgaa | Compositions cationiques à base d'eau avec polymères |
MX2016014465A (es) * | 2014-05-05 | 2017-04-27 | Multiple Energy Tech Llc | Composiciones de bioceramica y usos biomoduladores de las mismas. |
EP3194554A4 (fr) * | 2014-05-12 | 2018-04-25 | The Procter and Gamble Company | Composition de nettoyage anti-microbienne |
JP2019104924A (ja) * | 2019-02-19 | 2019-06-27 | ザ プロクター アンド ギャンブル カンパニーThe Procter & Gamble Company | 抗菌洗浄組成物 |
US20230140928A1 (en) * | 2021-11-05 | 2023-05-11 | Henkel IP & Holding GmbH | Method For Determining Stability Of A Liquid Fabric Softener Formulation |
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Also Published As
Publication number | Publication date |
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EP2212465A2 (fr) | 2010-08-04 |
WO2009065823A3 (fr) | 2009-09-24 |
EP2212465B2 (fr) | 2019-12-25 |
WO2009065823A2 (fr) | 2009-05-28 |
US20100227790A1 (en) | 2010-09-09 |
DE102007056936A1 (de) | 2009-05-28 |
US8143207B2 (en) | 2012-03-27 |
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