EP0264825A2 - Préparation pâteuse contenant peu d'eau - Google Patents

Préparation pâteuse contenant peu d'eau Download PDF

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Publication number
EP0264825A2
EP0264825A2 EP87115082A EP87115082A EP0264825A2 EP 0264825 A2 EP0264825 A2 EP 0264825A2 EP 87115082 A EP87115082 A EP 87115082A EP 87115082 A EP87115082 A EP 87115082A EP 0264825 A2 EP0264825 A2 EP 0264825A2
Authority
EP
European Patent Office
Prior art keywords
weight
polyacrylic acid
thickener
combination
fatty acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP87115082A
Other languages
German (de)
English (en)
Other versions
EP0264825A3 (fr
Inventor
Heinz-Manfred Wilsberg
Rolf Dr. Puchta
Klaus Dr. Köster
Ulrich Dr. Jahnke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0264825A2 publication Critical patent/EP0264825A2/fr
Publication of EP0264825A3 publication Critical patent/EP0264825A3/fr
Withdrawn legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0004Non aqueous liquid compositions comprising insoluble particles
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/18Hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2065Polyhydric alcohols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2093Esters; Carbonates
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3746Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3757(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • C11D3/3765(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in liquid compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2041Dihydric alcohols
    • C11D3/2044Dihydric alcohols linear

Definitions

  • the present invention relates to a low-water preparation suitable for spreading on textile substrates.
  • preparations containing active ingredients are applied locally to the substrates to be treated, so that the active ingredients on the substrates can develop their effect.
  • Such preparations are, for example, emulsions, solutions, dispersions, optionally in the form of ointments, creams or pastes. They are used e.g. in the cosmetic, pharmaceutical or printing technology sector or also in the cleaning or laundry industry or in the household and generally serve for the local application of active ingredients. Because of their easy handling, especially when dosed, pastes or creams are particularly popular with the user.
  • the pastes generally contain active substances or auxiliary substances, the viscosity of which is very dependent on the temperature; at low temperatures they are semi-solid to solid, at higher temperatures they become liquid to thin. For storage, transportation and the use of preparations which, because of their content of such constituents, have a strong viscosity / temperature dependence, this property can be a considerable disadvantage in some cases. It is therefore endeavored to give the pastes a consistency which ensures problem-free handling.
  • the person skilled in the art has thickeners and diluents available with which the consistency can be influenced. While the diluents are generally organic solvents or water, thickeners are inorganic or organic compounds which belong to a wide variety of substance classes. They increase or decrease the viscosity of the pastes or give them pseudoplastic properties. They often act either only in aqueous or only in non-aqueous systems and influence the viscosity / temperature dependency only inadequately or not at all.
  • the object of the present invention is therefore to provide a low-water, pasty agent for spreading on textile substrates with the aim of completely or largely eliminating its viscosity / temperature dependency.
  • the term "low in water” is intended to mean a water content of at most 10 percent by weight.
  • Low water should also include “water-free” in the sense that no water is added to such an agent and therefore it contains at most as much water as can get into the agent through the optionally used water-containing components.
  • an agent containing a combination of a thickener and a diluent comprising fatty acid alkanolamides, fatty acid esters, fatty alcohol ethoxylates and polyacrylic acid derivatives and the diluent comprising mono- or polyhydric alcohols having 1 to 6 carbon atoms and / or liquid hydrocarbons and the weight ratio from thickener to diluent is 1: 6 to 6: 1.
  • Fatty acid alkanolamides which are suitable for the purposes of the present invention are, for example, di- or preferably monoethanolamides which are derived from fatty acids or fatty acid mixtures with preferably 10 to 20 carbon atoms.
  • the fatty acids can be straight-chain or branched and saturated or mono- or polyunsaturated.
  • Typical representatives of the class of compounds mentioned are the preferably used stearic acid monoethanolamide and coconut fatty acid ethanolamide.
  • Suitable fatty acid esters are esters of fatty acids or fatty acid mixtures with preferably 10 to 20 carbon atoms with mono- or polyhydric alcohols with 1 to 5 carbon atoms.
  • the fatty acid component of the esters is the same as that of the fatty acid ethanolamides.
  • the alcohol component is either branched or straight-chain and is derived, for example, from ethanol, isopropyl alcohol, glycerol, ethylene glycol, diethylene glycol or pentaerythritol.
  • Typical fatty acid esters are the preferred glycerol monostearate, ethylene glycol monostearate, ethylene glycol distearate and mixtures thereof.
  • suitable fatty alcohol ethoxylates as to the fatty acids.
  • Fatty alcohol ethoxylates suitable as thickeners contain at least about 20 moles of ethylene oxide per mole of fatty alcohol.
  • An example of suitable compounds of this class is cetyl / stearyl alcohol, to which 30 moles of ethylene oxide are attached.
  • Fat derivatives suitable as thickeners in the context of the present invention are also to be understood as the reaction products of fats with hydroxyalkyl polyamines known, for example, from DE AS 19 22 047.
  • polyacrylic acid derivatives which are also suitable as thickeners are water-soluble compounds with a molecular weight between approximately 400,000 and 4,000,000. They can be used in acid form or as salts and are commercially available under the name "Carbopol” ®, company BF Goodrich .
  • Diluents in the sense of this invention are monohydric or polyhydric alcohols with 1 to 6 carbon atoms and liquid hydrocarbons or hydrocarbon mixtures with 6 to 40 carbon atoms; the alcohols and the hydrocarbons can be used either individually or in combination. Mixtures of noncyclic compounds, in particular isoparaffins, are preferred as hydrocarbons.
  • the agent according to the invention preferably contains components of textile detergents.
  • Washing aids can be applied, for example, to stained or heavily soiled items of laundry and improve the cleaning performance of the actual detergents in the subsequent washing process.
  • Washing aids of this type contain at least two customary components of textile detergents.
  • Typical components of textile detergents are, for example, nonionic, anionic, cationic or zwitterionic surfactants, nitrogen-containing detergent boosters, bleaching agents, bleach activators, water-soluble or water-insoluble builder substances, heavy metal complexing agents, foam regulators, graying inhibitors, fabric softeners, dyes, fragrances, enzymes.
  • preparations which contain nonionic surfactants in combination with further detergent constituents can be improved with regard to the viscosity / temperature behavior by the combination according to the invention.
  • Suitable alcohols are ethanol, propanol, butanol, ethylene glycol, diethylene glycol, propylene glycol, diacetone alcohol or glycerol or mixtures thereof, a mixture of mono-, di- and trihydric alcohols being preferred.
  • fatty acid esters for example ethylene glycol mono- and / or distearate
  • thickeners for example ethylene glycol mono- and / or distearate
  • Pasty compositions which contain 5 to 20 percent by weight of thickeners, in particular a combination of polyacrylic acid derivative and fatty acid ester and 30 to 60 percent by weight of diluents, in particular liquid hydrocarbons, are also preferred.
  • the polyacrylic acid derivatives suitable as thickeners are salts, in particular amine salts.
  • the salts are formed either by adding the thickener and the salt-forming basic component to the system to be thickened, or by pre-salting with the salt-forming component the addition to the system to be thickened.
  • Water-free or largely water-free systems can be thickened well with amine salts, while noticeable amounts of water-containing preparations (up to 10% by weight) can be thickened well with alkali salts.
  • Combinations of polyacrylic acid with quaternary ammonium compounds, such as in particular tetradecyl or cetyltrimethylammonium bromide are also suitable for thickening preparations with a water content of up to about 10 percent by weight.
  • the polyacrylic acid salt of fatty amines for example coconut alkyl amine, in particular that of polyacrylic acid and that of the adduct of 2 moles of ethylene oxide with coconut alkyl amine, has proven particularly useful. Good results are also achieved with higher ethoxylated fatty amines or with non-ethoxylated fatty amines with 10 to 20 carbon atoms.
  • a polyacrylic acid derivative in combination with one of the fatty alkyl derivatives already mentioned as thickeners, in particular with a fatty acid ester is particularly preferred.
  • High molecular weight polyacrylic acid derivatives are preferred in the context of this invention, i.e. those polymers which have a molecular weight of at least 500,000, in particular of at least 1,000,000 and preferably of about 4,000,000.
  • Such a polyacrylic acid derivative is, for example, the commercial product "Carbopol 940®" from B.F. Goodrich, United States.
  • Preparations whose viscosity is regulated by a combination of a polyacrylic acid derivative with a cationic surfactant as a thickening component and with liquid hydrocarbons as a diluting component have interesting rheological properties.
  • Preparations according to the invention are suitable, for example, as laundry pretreatment agents with which heavily soiled textiles or parts of textiles, such as e.g. Collar edges can be pretreated to enhance the washing effect of the wash liquor during a subsequent wash.
  • Such preparations therefore contain cleaning, dissolving or bleaching components of the type described above.
  • Good results are obtained with preparations which contain at least one nonionic surfactant and one cationic surfactant.
  • Suitable nonionic surfactants include, in particular, addition products of ethylene oxide with fatty alcohols or, in particular, oxo alcohols with 12 to 18 carbon atoms.
  • Particularly suitable surfactants are derived from alcohols with 14 to 15 carbon atoms.
  • oxo alcohol ethoxylates which contain 3 to 10, preferably 6 to 8 and in particular about 7 moles of ethylene oxide per mole of alcohol.
  • foam regulators are, for example, the known silicone oils.
  • the nonionic surfactant content of the paste promotes the removal of greasy or oily soiling during washing.
  • Suitable cationic surfactants contain long-chain alkyl or alkenyl radicals with 10 to 20, preferably alkyl groups with 10 to 16 and in particular about 14 carbon atoms.
  • the suitable quaternary ammonium compounds contain 3 identical or different alkyl groups with 1 to 4 carbon atoms.
  • these short alkyl groups are methyl groups.
  • a particularly good quaternary ammonium compound is tetradecyltrimethylammonium bromide, which can also be used to enhance the thickening effect of polyacrylic acid derivatives in very low-water preparations.
  • Another agent contains at least one nonionic surfactant of the aforementioned type and a bleach activator for per compounds.
  • activators for per compounds are N-acyl and O-acyl compounds. Examples of this are tetraacetylglycoluril or pentaacetylglucose or in particular tetraacetylethylenediamine.
  • the bleach activators mentioned lead to improved removal of bleachable textile soiling.
  • preferred laundry pretreatment agents according to the invention contain both a nonionic surfactant, a cationic surfactant and a bleach activator of the type described above.
  • the viscosity of particularly effective and therefore preferred agents is regulated by the use of a thickener consisting of a polyacrylic acid derivative and a fatty acid derivative, preferably a fatty acid ester Combination in which the polyacrylic acid derivative has a molecular weight of at least 500,000, preferably at least 1,000,000 and in particular approximately 4,000,000 and a diluting mixture of propylene glycol, glycerol and ethanol.
  • a thickener consisting of a polyacrylic acid derivative and a fatty acid derivative, preferably a fatty acid ester Combination in which the polyacrylic acid derivative has a molecular weight of at least 500,000, preferably at least 1,000,000 and in particular approximately 4,000,000 and a diluting mixture of propylene glycol, glycerol and ethanol.
  • the viscosity of a C14 / C15 oxo alcohol + 7 moles of ethylene oxide and tetraacetylethylene diamine is set by using an amine salt of polyacrylic acid formed from coconut amine + 2 moles of ethylene oxide with a molecular weight of approximately 4,000,000 in combination with ethylene glycol stearate as a thickener and a mixture of propylene glycol, glycerol and ethanol as a diluent in such a way that the viscosity is essentially constant within a temperature range from -5 to +40 ° C, ie that the viscosity is adjusted in this temperature range so that the product is a is easy to handle, especially a well spreadable paste.
  • the agent according to the invention is not always a laundry pretreatment agent, even if the following examples represent laundry treatment agents.
  • a pasty laundry pretreatment was prepared by mixing the following ingredients together: 21.8% by weight of C14 / C15 oxo alcohol + 7 moles of ethylene oxide 15.7% by weight of tetraacetylethylene diamine 8.2% by weight tetradecyltrimethylammonium bromide 15.3% by weight of 1,2-propylene glycol 7.6% by weight glycerin 7.5% by weight coconut amine + 2 moles of ethylene oxide 0.8% by weight polyacrylic acid, molecular weight 4,000,000 12.6% by weight of ethylene glycol stearate 1.2% by weight silicone oil 9.3% by weight of ethanol
  • the mixing was carried out in such a way that 2/3 of the total propylene glycol together with the glycerol, the oxo alcohol ethoxylate and the defoamer were heated to about 65 ° C. with stirring using a propeller stirrer.
  • a premix of the polyacrylic acid and the tetradecyltrimethylammonium bromide was added at this temperature and the mixture was stirred until the mixture was homogeneously mixed, which took about 1 hour.
  • the remaining propylene glycol, the coconut amine ethoxylate and the ethylene glycol stearate were added in a stirrer with an anchor stirrer and Teflon wall wipers.
  • the mixture was allowed to cool with further stirring and, after the temperature had dropped below 40 ° C., the ethanol and the tetraacetylethylenediamine were added and the mixture was cooled to room temperature.
  • This mixture is a beige / gray paste that has excellent effects as a laundry pretreatment agent.
  • the paste in the Temperature range of 5 to 40 ° C, the paste is always easy to spread.
  • a paste of the following composition was produced by mixing the components: 15.4% by weight of C14C15 oxo alcohol + 7 moles of ethylene oxide 46.3% by weight of C12 / C14 isoparaffin-hydrocarbon mixture ("Isopar M", Esso) 0.8% by weight polyacrylic acid, molecular weight 4,000,000 8.0 weight percent tetradecyltrimethylammonium bromide 10.0% by weight of ethylene glycol stearate 16.0% by weight tetraacetylethylenediamine 2.3% by weight water 1.2% by weight silicone oil
  • This mixture was a paste which was always easy to spread in the temperature range from 5 to 40 ° C. and had an excellent effect as a laundry pretreatment agent.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP87115082A 1986-10-23 1987-10-15 Préparation pâteuse contenant peu d'eau Withdrawn EP0264825A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3636085 1986-10-23
DE19863636085 DE3636085A1 (de) 1986-10-23 1986-10-23 Wasserarmes, pastenfoermiges praeparat

Publications (2)

Publication Number Publication Date
EP0264825A2 true EP0264825A2 (fr) 1988-04-27
EP0264825A3 EP0264825A3 (fr) 1990-08-08

Family

ID=6312323

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87115082A Withdrawn EP0264825A3 (fr) 1986-10-23 1987-10-15 Préparation pâteuse contenant peu d'eau

Country Status (4)

Country Link
EP (1) EP0264825A3 (fr)
JP (1) JPS63120800A (fr)
DE (1) DE3636085A1 (fr)
DK (1) DK554087A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5298195A (en) * 1992-03-09 1994-03-29 Amway Corporation Liquid dishwashing detergent
EP1894989A1 (fr) * 2006-09-01 2008-03-05 The Procter and Gamble Company Composition pâteuse pour articles sanitaires
WO2015010830A1 (fr) * 2013-07-26 2015-01-29 Buck-Chemie Gmbh Agent adhésif destiné à être appliqué sur un objet sanitaire

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997039175A1 (fr) * 1996-04-16 1997-10-23 Matsumoto Yushi-Seiyaku Co., Ltd. Traitement pour textiles
US8658588B2 (en) * 2012-01-09 2014-02-25 S.C. Johnson & Son, Inc. Self-adhesive high viscosity cleaning composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU44944A1 (fr) * 1962-12-06 1964-02-04
DE2033016A1 (en) * 1970-07-03 1972-01-13 Henkel & Cie GmbH, 4000 Düsseldorf Hand-cleansing pastes - with mild abrasive action contg non-ionic surfactant and alkaline salts
FR2252403A1 (en) * 1973-11-26 1975-06-20 Henkel & Cie Gmbh Shampoo or bubble bath compsn. with regreasing props. - detergent mixture etc. plus separate oil layer
EP0109022A2 (fr) * 1982-11-09 1984-05-23 MIRA LANZA S.p.a. Composition détergente concentrée liquide appropriée pour la préparation de détergents liquides pour lavages délicats de lingerie et pour la vaisselle.
GB2194547A (en) * 1986-09-02 1988-03-09 Colgate Palmolive Co Laundry pre-spotter composition providing oily soil removal

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU44944A1 (fr) * 1962-12-06 1964-02-04
DE2033016A1 (en) * 1970-07-03 1972-01-13 Henkel & Cie GmbH, 4000 Düsseldorf Hand-cleansing pastes - with mild abrasive action contg non-ionic surfactant and alkaline salts
FR2252403A1 (en) * 1973-11-26 1975-06-20 Henkel & Cie Gmbh Shampoo or bubble bath compsn. with regreasing props. - detergent mixture etc. plus separate oil layer
EP0109022A2 (fr) * 1982-11-09 1984-05-23 MIRA LANZA S.p.a. Composition détergente concentrée liquide appropriée pour la préparation de détergents liquides pour lavages délicats de lingerie et pour la vaisselle.
GB2194547A (en) * 1986-09-02 1988-03-09 Colgate Palmolive Co Laundry pre-spotter composition providing oily soil removal

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5298195A (en) * 1992-03-09 1994-03-29 Amway Corporation Liquid dishwashing detergent
US5443757A (en) * 1992-03-09 1995-08-22 Amway Corporation Liquid dishwashing detergent
EP1894989A1 (fr) * 2006-09-01 2008-03-05 The Procter and Gamble Company Composition pâteuse pour articles sanitaires
WO2008026192A1 (fr) * 2006-09-01 2008-03-06 The Procter & Gamble Company Composition pâteuse destinée à des équipements sanitaires
WO2015010830A1 (fr) * 2013-07-26 2015-01-29 Buck-Chemie Gmbh Agent adhésif destiné à être appliqué sur un objet sanitaire

Also Published As

Publication number Publication date
JPS63120800A (ja) 1988-05-25
EP0264825A3 (fr) 1990-08-08
DK554087D0 (da) 1987-10-22
DE3636085A1 (de) 1988-04-28
DK554087A (da) 1988-04-24

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