US3619119A - Pasty spot-treating compositions for use on textiles - Google Patents

Pasty spot-treating compositions for use on textiles Download PDF

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Publication number
US3619119A
US3619119A US783097A US3619119DA US3619119A US 3619119 A US3619119 A US 3619119A US 783097 A US783097 A US 783097A US 3619119D A US3619119D A US 3619119DA US 3619119 A US3619119 A US 3619119A
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percent
weight
carbon atoms
alcohol mixture
component
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Gunter Felletschin
Josef Hartenstein
Horst-Jurgen Krause
Gunter Reese
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • 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
    • C11D11/00Special methods for preparing compositions containing mixtures of detergents
    • C11D11/02Preparation in the form of powder by spray drying
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/83Mixtures of non-ionic with anionic compounds
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/83Mixtures of non-ionic with anionic compounds
    • C11D1/8305Mixtures of non-ionic with anionic compounds containing a combination of non-ionic compounds differently alcoxylised or with different alkylated chains
    • 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
    • C11D3/02Inorganic compounds ; Elemental compounds
    • C11D3/04Water-soluble compounds
    • C11D3/046Salts
    • 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
    • C11D3/34Organic compounds containing sulfur
    • C11D3/3418Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
    • 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
    • C11D3/3703Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3707Polyethers, e.g. polyalkyleneoxides
    • 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
    • C11D3/39Organic or inorganic per-compounds
    • C11D3/3942Inorganic per-compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/01Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using only solid or pasty agents
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols

Definitions

  • Patented [73] Assignee Nov. 9. 1971 Henkel 8; Cie G.m.b.H. Duesseldort-l-lolthausen, Germany ⁇ 32] Priority D66. 28,1967 1 1 Germany [31] P16171390 [54] PASTY SPOT-TREATING COMPOSITIONS FOR [56] References Cited UNITED STATES PATENTS 2,806,001 9/1957 Fong et al. 252/138 2.877.185 3/1959 Krumrei eta1.... 252/138 2.954.347 9/1960 St. John etal. 252/321 3.156.655 11/1964 Bright 252/89 3,417,023 12/1968 DiSalvo 3.419.500 12/1968 Rytteretal. .1
  • ABSTRACT A pasty spot-treating composition comprising (a) from 2 percent to 10 percent by weight of a primary alcohol mixture containing at least 70 percent of straight-chain C to C, alcohols. ethoxylated with from 8 to 20 mols. of ethylene oxide. (1)) from 0.5 percent to 5 percent by weight of a primary alcohol mixture containing at least 70 percent of straight-chain.
  • the spot-treating compositions have a practically constant viscosity. are easily rubbed on textiles and have foam-suppressing properties.
  • pastes which are pliable and preparations which are liquid at room temperature become so viscous at temperatures below l C. that they can no longer be poured out of the storage bottles or pressed out oftheir tubes.
  • pastes become liquid at temperatures above 25 to 30 C. so that they run out of an open tub easily when it is in a horizontal position.
  • an object of the invention is the preparation of a spottreating composition which distinguishes itself by a high cleaning power as well as by viscosity behavior substantially independent of the temperature.
  • Another object of the present invention is the obtention ofa pasty spot-treating composition
  • a pasty spot-treating composition comprising (a) from 2 to percent by weight of a primary alcohol mixture containing at least 70 percent of straight-chain C to C alcohols, ethoxylated with from 8 to mols of ethylene oxide, (b) from 0.5 to 5 percent by weight ofa primary alcohol mixture containing at least 70 percent of straight-chain, saturated C to C fatty alcohols, ethoxylated with from 1 to 5 mols of ethylene oxide, (c) from 15 to percent by weight of an alcohol mixture of alcohols having 10 to 18 carbon atoms, containing at least 50 percent by weight of straight-chain alkanols, ethoxylated with from I to 4 mols of ethylene oxide and sulfated, in the form of a salt selected from the group consisting of alkali metal and ammonium salts, (d) from 0.3 to 5 percent by weight of a hydrotropic compound selected from the group consisting
  • said polyoxyethyleneglycol monoether containing from 8 to 20. preferably from 10 to 15 ethylene oxide units;
  • an aqueous solution media preferably water with or without water-miscible organic solvents.
  • the pasty spot-treating composition of the invention may, if desired, contain from 0.5 to 10 percent by weight of a foam inhibitor, particularly from 1 to 5 percent of saturated C to C fatty acids or their alkali metal salts.
  • a foam inhibitor particularly from 1 to 5 percent of saturated C to C fatty acids or their alkali metal salts.
  • the spot-treating compositions of the invention may contain additional oligomeric or polymeric polyoxyethyleneglycols, for example, dior trioxyethyleneglycol, and particularly polyoxyethyleneglycols with a molecular weight of 2,000 to 20,000.
  • the polyoxyethyleneglycols may be present in amounts of from 0.l to 5 percent, preferably 0.5 to 3 percent by weight.
  • the addition of the polyoxyethyleneglycols to the pasty spot-treating composition improves its viscosity characteristics.
  • the spot-treating materials of the invention may contain neutral salts, particularly neutral alkali metal salts of strong inorganic acids, such as sodium chloride and sodium sulfate, in amounts of between 0.l to 5 percent by weight.
  • neutral salts particularly neutral alkali metal salts of strong inorganic acids, such as sodium chloride and sodium sulfate, in amounts of between 0.l to 5 percent by weight.
  • aqueous solution media for the components mentioned above, water is preferred, which may be present in amounts of between 50 and 75 percent by weight.
  • organic, water-miscible solvents preferably lower alkanols, such as methanol, ethanol or isopropanol may also be present in the mixture in small amounts, whereby the viscosity of the pasty spot-treating materials can be varied within certain limits as well. In general, however, such solvent additives are not required.
  • the polyoxyethyleneglycol monoethers or ethylene oxide condensates of component (a) are derived by condensing from 8 to 20 mols, preferably from 10 to [5 mols of ethylene oxide with primary alcohols containing at least 70 percent of saturated and/or unsaturated straight-chain C to C ,t alcohols.
  • These primary alcohols may be obtained in known ways, either by hydrogenation of naturally occurring fatty acids such as tallow fatty acids, cottonseed oil fatty acids, soybean oil fatty acids, palm oil fatty acids, rapeseed oil fatty acids, etc. or synthetically, for example, through polymerization of ethylene and subsequent hydration of a terminal double bond.
  • the primary alcohols utilized are preferably alkanols having 12 to 22 carbon atoms, alkenols having 12 to 22 carbon atoms and alkadienols having 12 to 22 carbon atoms wherein at least 70 percent of the alcohol mixture is primary straight-chain alcohols having from 16 to 18 carbon atoms.
  • the amount of alcohol radicals with 12 to 14 or 20 to 22 carbon atoms in these compounds may amount to up to 30 percent.
  • the named polyoxyethyleneglycol monoethers are water soluble and have a cloud point of more than 30 C.
  • the polyoxyethyleneglycol monoethers have the formula wherein R represents primary straight-chain substituents selected from the group consisting of alkyls having 12 to 22 carbon atoms, alkenyls having 12 to 22 carbon atoms and alkadienyls having 12 to 22 carbon atoms, at least 70 percent of said primary substituents having 16 to 18 carbon atoms and m represents an integer from eight to 20.
  • the polyoxyethyleneglycol monoethers or ethylene oxide condensates of component (b) are derived by condensing from 1 to mols, preferably from 2 to 5 mols of ethylene oxide with primary alcohols containing at least 70 percent of saturated, straight-chain C,- to C alcohols.
  • primary alcohols are obtainable in known ways such as by reduction of fatty acids such as coconut or palm kernel fatty acids or through polymerization of ethylene and subsequent hydration of a terminal double bond.
  • the primary alcohols utilized are preferably straight-chain alkanols having eight to 18 carbon atoms wherein at least 70 percent of the alcohol mixture is primary, straight-chain, saturated alcohols having from 12 to 14 carbon atoms. in these compounds the portion of alkyl radicals with eight to or 16 to 18 carbon atoms can amount to 30 percent.
  • the named polyoxyethyleneglycol monoethers are difficulty soluble in water.
  • the polyoxyethyleneglycol monoethers have the formula wherein R represents primary, straight-chain alkyls having eight to 18 carbon atoms, at least 70 percent of said alkyl having 12 to 14 carbon atoms and n represents an integer from 1 to 5.
  • the sulfated polyoxyethyleneglycol monoethers or sulfated ethylene oxide condensates of component (c) are derived by condensing from 1 to 4 mols of ethylene oxide with an alcohol mixture containing eight to 18 carbon atoms, and at least 50 percent by weight of saturated, straight-chain C to C alcohols, and sulfating the terminal hydroxyl group of the glycol monoether.
  • the alcohols utilized may be obtained in known ways, such as by reduction of fatty acids such as coconut or palm kernel fatty acids or synthetically.
  • the alcohols utilized are preferably primary, straight-chain alkanols having eight to 18 carbon atoms wherein at least 50 percent of the alcohol mixture is alkanols having 12 to 14 carbon atoms.
  • Alkyl radicals with eight to 10 as well as 16 to 18 carbon atoms may be present in smaller amounts as well.
  • the sulfates can be in the form of their sodium, potassium or ammonium salts where the term ammonium salts include as well the salts of the mono-, diand triethanolamines, of morpholines or of other primary secondary or tert. amines with lower alkyl chains.
  • the sulfuric acid esters of the glycol monoethers may be in the form of their salts with alkali metals, ammonia, ethanolamines, morpholine and lower-a]- kylamines.
  • the salts of the sulfuric acid esters of the glycol monoethers have the formula wherein R. represents primary, straight-chain alkyls having eight to 18 carbon atoms, at least 50 percent of said alkyls having 12 to 14 carbon atoms, 2 represents an integer from 1 to 4 and Me represents a member selected from the group consisting of alkali metal, ammonium, ethanolammonium. morpholinium and lower-alkylammonium.
  • hydrotropic compounds of component (d) are available as well in the form of sodium.
  • potassium or ammonium salts where the ammonium salts are salts of alkylamines or alkylolamines according to the above definition as well.
  • the preparation of the substances of theinvention is carried out by means of simple admixing or melting together of the individual components.
  • the spot-treating materials of the invention distinguish themselves by a high cleaning effect, particularly toward persistent fat and oil containing soils. They react neutrally. have a fiber protecting effect and consequently are suitable for sensitive textiles.
  • the products containing behenic acid or other higher fatty acids possess foam inhibiting properties and from that follows that textiles which were treated therewith can be washed in closed-drum washing machines with common, slightly or moderately foaming detergents, without risking a foaming over of the washing liquor. It must be underlined that these spot-treating materials have an almost steady viscosity within the temperature range of 0 and 30. Therefore, even after longer storage periods at relatively high or low temperatures, the spot-treating materials can be removed from their containers and applied to the textiles much easier.
  • EXAMPLE 1 A mixture of the following composition was prepared by admixing at approximately C. The amount of the ingredients is in percent by weight.
  • EXAMPLE 2 A cleaning paste of the following composition was prepared by melting the ingredients together at approximately 80 C. The amount of the ingredients is in percent by weight.
  • the spot-treating material can as well be admixed with a preservation agent, for example, sodium benzoate in amounts of from 0.05 to 0.2 percent, as well as a perfume.
  • a preservation agent for example, sodium benzoate in amounts of from 0.05 to 0.2 percent, as well as a perfume.
  • the viscosity behavior with reference to the temperature was determined by means of a rotation viscometer. The following values were obtained.
  • a pasty spot-treating composition having a substantially steady viscosity within the temperature range of to 40 C. consisting essentially of (a) from 2 to 10 percent by weight of a primary alcohol mixture containing at least 70 percent of straight-chain C to C, alcohols, ethoxylated with from 8 to 20 mols of ethylene oxide, (b) from 0.5 to percent by weight of a primary alcohol mixture containing at least 70 percent of straight-chain, saturated C to C fatty alcohols, ethoxylated with from I to 5 mols of ethylene oxide, (0) from [5 to 30 percent by weight of an alcohol mixture of alcohols having to l8 carbon atoms, containing at least 50 percent by weight of straight-chain alkanols, ethoxylated with from 1 to 4 mols of ethylene oxide and sulfated, in the form of a salt selected from the group consisting of alkali metal and ammonium salts, (d) from 0.3 to 5 percent by weight of a hydrotropic compound selected from the group
  • component (a) is present in an amount of from 3 to 7 percent by weight
  • component (b) is present in an amount of from I to 3 percent by weight
  • component (c) is present in an amount of from 18 to 25 percent by weight
  • component (d) is present in an amount of from 0.5 to 2 percent by weight
  • component (e) is present in an amount of from 0.5 to 3 percent by weight
  • component (f) is water and is present in an amount offrom 63 to 75 percent by weight.
  • the spot-treating composition as defined in any one of claims I and 2, containing as an additional component, from 0.5 to 10 percent by weight of a foam inhibitor selected from the group consisting of saturated fatty acids having 20 to 22 carbon atoms and alkali metal salts thereof.
  • said component (a) is a polyoxyethyleneglycol monoether of a primary alcohol mixture having from 10 to 15 ethylene oxide units in said glycol monoether moiety, said primary alcohol mixture being selected from the group consisting of alkanols having 12 to 22 carbon atoms, alkenols having 12 to 22 carbon atoms and alkadieneols having 12 to 22 carbon atoms wherein at least 70 percent of said alcohol mixture consists of alcohols having from 16 to 18 carbon atoms.
  • said component (b) is a polyoxyethyleneglycol monoether of a primary alcohol mixture having from 2 to 5 ethylene oxide units in said glycol monoether, said primary alcohol mixture being a mixture of straight-chain alkanols having eight to 18 carbon atoms wherein at least 70 percent of said alcohol mixture consists of alkanols having from 12 to 14 carbon atoms.
  • a method of cleaning textiles having concentrated soil spots which comprises rubbing the pasty soil-trcating composition, as defined in claim 1, in said concentrated soil spots, washing and rinsing said textiles.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US783097A 1967-12-28 1968-12-11 Pasty spot-treating compositions for use on textiles Expired - Lifetime US3619119A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19671617140 DE1617140A1 (de) 1967-12-28 1967-12-28 Bleichendes,koerniges Waschmittel und Verfahren zur Herstellung desselben
DE19671617139 DE1617139A1 (de) 1967-12-28 1967-12-28 Pastenfoermiges Fleckenbehandlungsmittel fuer Textilien
DEH0064985 1967-12-28
DEH0064895 1967-12-28
DEH0064894 1967-12-28

Publications (1)

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US3619119A true US3619119A (en) 1971-11-09

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US783097A Expired - Lifetime US3619119A (en) 1967-12-28 1968-12-11 Pasty spot-treating compositions for use on textiles

Country Status (9)

Country Link
US (1) US3619119A (fr)
AT (1) AT291409B (fr)
BE (2) BE726079A (fr)
CH (2) CH505889A (fr)
DE (2) DE1617139A1 (fr)
DK (2) DK128786C (fr)
FR (2) FR1590350A (fr)
GB (1) GB1191356A (fr)
NL (2) NL6817036A (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
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US3983078A (en) * 1973-10-15 1976-09-28 The Procter & Gamble Company Oil removal detergent compositions
US3985670A (en) * 1973-06-01 1976-10-12 Henkel & Cie G.M.B.H. Liquid regulated-foam detergent compositions
JPS5238508A (en) * 1975-09-22 1977-03-25 Kao Corp Liquid detergent composition
US4083793A (en) * 1973-05-23 1978-04-11 Henkel Kommanditgesellschaft Auf Aktien Washing compositions containing aluminosilicates and nonionics and method of washing textiles
US4129514A (en) * 1976-03-24 1978-12-12 Rhone-Poulenc Industries Surface-active composition based on non-ionic surfactants
US4409136A (en) * 1977-01-31 1983-10-11 Colgate Palmolive Company Molecular sieve zeolite-built detergent paste
US4648987A (en) * 1985-02-13 1987-03-10 The Clorox Company Thickened aqueous prewash composition
US4861516A (en) * 1987-04-25 1989-08-29 Henkel Kommanditgesellschaft Auf Aktien Laundry pretreatment composition for oily and greasy soil
US4877556A (en) * 1986-08-02 1989-10-31 Henkel Kommanditgesellschaft Auf Aktien Cleaning compositions containing an alcohol and fatty acid ester and their use in the pretreatment of fabrics
US5282997A (en) * 1991-04-25 1994-02-01 Betz Paperchem, Inc. Process and composition for deinking dry toner electrostatic printed wastepaper
US5362413A (en) * 1984-03-23 1994-11-08 The Clorox Company Low-temperature-effective detergent compositions and delivery systems therefor
US5648326A (en) * 1994-05-17 1997-07-15 S. C. Johnson & Son, Inc. Laundry pre-spotter with associative polymeric thickener
US5652208A (en) * 1994-05-17 1997-07-29 S. C. Johnson & Son, Inc. Laundry pre-spotter with associative polymeric thickener
US20100294367A1 (en) * 2009-05-19 2010-11-25 Honeywell International Inc. Solar cell with enhanced efficiency
NL2020571B1 (nl) * 2018-03-12 2019-09-20 Sellacq Holland B V Werkwijze voor het maken van een vast betonelement, substantie en cilindrische behuizing welke een opening omvat, zoals een kitspuit, gevuld met de substantie

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5122984B2 (fr) * 1972-07-29 1976-07-14
DE2559225A1 (de) * 1975-01-03 1976-07-15 Procter & Gamble Europ Fluessiges wasch- und reinigungsmittel sowie seine anwendung
GB2041966A (en) 1977-11-29 1980-09-17 Procter & Gamble Detergent tablet having a hydrated salt coating and process for preparing the tablet
EP0002293A1 (fr) * 1977-11-29 1979-06-13 THE PROCTER & GAMBLE COMPANY Détergent sous forme de tablette ayant une enveloppe de sel hydraté et procédé pour la fabrication de cette tablette
DE3823977A1 (de) * 1988-02-08 1990-01-18 Henkel Kgaa Verbessertes maschinenwaschverfahren fuer verschmutztes textilgut
GB9110719D0 (en) * 1991-05-17 1991-07-10 Allied Colloids Ltd Polymeric compositions and methods of making and using them

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US2806001A (en) * 1952-12-05 1957-09-10 Fong Willie Polyethyleneglycols as laundering aids
US2877185A (en) * 1956-06-29 1959-03-10 Procter & Gamble Clear liquid detergent composition
US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition
US3156655A (en) * 1960-08-02 1964-11-10 Lever Brothers Ltd Heavy duty liquid detergent composition
US3417023A (en) * 1965-10-21 1968-12-17 Colgate Palmolive Co Detergent spotting stick
US3419500A (en) * 1965-10-21 1968-12-31 Lever Brothers Ltd Novel process and composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2806001A (en) * 1952-12-05 1957-09-10 Fong Willie Polyethyleneglycols as laundering aids
US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition
US2877185A (en) * 1956-06-29 1959-03-10 Procter & Gamble Clear liquid detergent composition
US3156655A (en) * 1960-08-02 1964-11-10 Lever Brothers Ltd Heavy duty liquid detergent composition
US3417023A (en) * 1965-10-21 1968-12-17 Colgate Palmolive Co Detergent spotting stick
US3419500A (en) * 1965-10-21 1968-12-31 Lever Brothers Ltd Novel process and composition

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Title
Matson, Syndets with Alcohol Derivatives, Soap & Chem. Spec. Nov. 1963, pages 1 8 *

Cited By (16)

* Cited by examiner, † Cited by third party
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Also Published As

Publication number Publication date
AT291409B (de) 1971-07-12
NL6818098A (fr) 1969-07-01
DE1617139A1 (de) 1971-03-11
CH515989A (de) 1971-11-30
FR1602442A (fr) 1970-11-23
DK128786C (fr)
FR1590350A (fr) 1970-04-13
GB1191356A (en) 1970-05-13
BE726106A (fr) 1969-06-27
BE726079A (fr) 1969-06-27
NL6817036A (fr) 1969-07-01
DE1617140A1 (de) 1971-03-11
DK127006A (fr)
CH505889A (de) 1971-04-15

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