EP0638638B1 - Composition détergente liquide à base de surfactant non ionique très moussant - Google Patents

Composition détergente liquide à base de surfactant non ionique très moussant Download PDF

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Publication number
EP0638638B1
EP0638638B1 EP94401591A EP94401591A EP0638638B1 EP 0638638 B1 EP0638638 B1 EP 0638638B1 EP 94401591 A EP94401591 A EP 94401591A EP 94401591 A EP94401591 A EP 94401591A EP 0638638 B1 EP0638638 B1 EP 0638638B1
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EP
European Patent Office
Prior art keywords
alkyl
liquid detergent
detergent composition
group
ethylene oxide
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.)
Expired - Lifetime
Application number
EP94401591A
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German (de)
English (en)
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EP0638638A1 (fr
Inventor
Rita Erilli
Gilbert S. Gomes
Stephen Repinec
Ronald Kern
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.)
Colgate Palmolive Co
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Colgate Palmolive Co
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Filing date
Publication date
Priority claimed from US08/091,514 external-priority patent/US5387375A/en
Priority claimed from US08/091,517 external-priority patent/US5389304A/en
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Publication of EP0638638A1 publication Critical patent/EP0638638A1/fr
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Publication of EP0638638B1 publication Critical patent/EP0638638B1/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • a high foaming, nonionic based, liquid detergent composition containing a nonionic surfactant, at least one anionic surfactant, a dialkyl sulfosuccinate and a foaming zwitterionic surfactant selected from betaine type surfactants, wherein the composition does not contain any amine oxide, calcium carbonate, alkali metal carbonate, polymeric or clay thickeners, abrasive, clays, silicas, alkanol amides, (for example cocodiethanol amide), alkyl glycine surfactant, cyclic imidinium surfactant, or more than 3.0 wt. % of a fatty acid or a metal salt of the fatty acid compounds.
  • a high foaming liquid detergent can be formulated with a nonionic surfactant which has desirable cleaning properties, mildness to the human skin.
  • Still another object of this invention is to provide a novel, liquid detergent with desirable high foaming and cleaning properties which is mild to the human skin.
  • the total amount of surfactants may constitute 10% - 55%, preferably 20%-40%, most preferably 25% - 35%, by weight of the liquid composition.
  • the nonionic surfactant which constitutes the major ingredient in the liquid detergent composition is present in amounts of 10 to 30%, preferably 12 to 25% by weight of the composition and provides superior performance in the removal of oily soil and mildness to human skin.
  • the water soluble nonionic surfactants utilized in this invention are commercially well known and include the primary aliphatic alcohol ethoxylates, secondary aliphatic alcohol ethoxylates, alkylphenol ethoxylates and ethylene-oxide-propylene oxide condensates on primary alkanols, such a Plurafacs® (BASF) and condensates of ethylene oxide with sorbitan fatty acid esters such as the Tweens® (ICI).
  • the nonionic synthetic organic detergents generally are the condensation products of an organic aliphatic or alkyl aromatic hydrophobic compound and hydrophilic ethylene oxide groups.
  • any hydrophobic compound having a carboxy, hydroxy, amido, or amino group with a free hydrogen attached to the nitrogen can be condensed with ethylene oxide or with the polyhydration product thereof, polyethylene glycol, to form a water soluble nonionic detergent. Further, the length of the polyethenoxy hydrophobic and hydrophilic elements.
  • Preferred anionic surfactants are the water soluble C 12 -C 16 alkyl sulfates, the C 10 -C 15 alkylbenzene sulfonates, the C 12 -C 17 paraffin sulfonates, C 8 -C 18 ethoxylated alkyl ether sulfates and the alpha C 12 -C 18 olefin sulfonates.
  • Suitable other sulfonated anionic detergents are the higher alkylbenzene sulfonates containing 9 to 18 or preferably 9 to 10 to 15 or 16 carbon atoms in the higher alkyl group in a straight or branched chain.
  • This particular combination of dialkyl sulfosuccinate ester surfactant, at least one anionic surfactant and a betaine surfactant provides a detergent system which coacts with the nonionic surfactant to produce a liquid detergent composition with desirable foaming, foam stability and detersive properties.
  • the resultant homogeneous liquid detergent exhibits the same or better foam performance, both as to initial foam volume and stability of foam in the presence of soils, and cleaning efficacy as an anionic based light duty liquid detergent (LDLD) as shown in the following Examples.
  • LDLD light duty liquid detergent
  • aqueous medium comprising water and optionally, solubilizing ingredients such as alcohols and dihydroxy alcohols such as C2-C3 mono- and di-hydoroxy alkanols, e.g. ethanol isopropanol and propylene glycol.
  • solubilizing ingredients such as alcohols and dihydroxy alcohols such as C2-C3 mono- and di-hydoroxy alkanols, e.g. ethanol isopropanol and propylene glycol.
  • Suitable water soluble hydrotropic salts include sodium, potassium, ammonium and mono-, di- and triethanolammonium salts of (C 1 -C 3 )alkyl substituted benzene sulfonate hydrotropes.
  • the aqueous medium is primarily water, preferably said solubilizing agents are included in order to control the viscosity of the liquid composition and to control low temperature could clear properties.
  • the proportion of solubilizer generally will be from 0.5% to 8%, preferably 1% to 7%, by weight of the detergent composition with the proportion of ethanol, when present, being 5% of weight or less in order to provide a composition having a flash point above 46°C.
  • the solubilizing ingredient will be propylene glycol.
  • Sodium formate can be included in the formula as a perservative at a concentration of 0.1 to 4.0%.
  • Sodium bisulfite can be used as a color stabilizer at a concentration of 0.01 to 0.2 wt.%.
  • Typical perservatives are dibromodicyano-butane, citric acid, benzylic alcohol and poly (hexamethylene-biguamide) hydr-chloride and mixtures thereof.
  • compositions can contain 1 to 4 wt. %, more preferably 0.5 to 3.0 wt. % of an alkyl polysaccharide surfactant.
  • the alkyl polysaccharides surfactants which are used in conjunction with the aforementioned surfactant have a hydrophobic group containing from 8 to abut 20 carbon atoms, preferably from 10 to 16 carbon atoms, most preferably from 12 to 14 carbon atoms, and polysaccharide hydrophilic group containing from 1.5 to 10, preferably from 1.5 to 4, most preferably from 1.6 to 2.7 saccharide units (e.g., galactoside, glucoside, fructoside, glucosyl, fructosyl; and/or galactosyl units).
  • the number x indicates the number of saccharide units in a particular alkyl polysaccharide surfactant.
  • x can only assume integral values.
  • the physical sample can be characterized by the average value of x and this average value can assume non-integral values. In this specification the values of x are to be understood to be average values.
  • the hydrophobic group (R) can be attached at the 2-, 3-, or 4- positions rather than at the 1-position, (thus giving e.g.
  • Typical hydrophobic groups include alkyl groups, either saturated or unsaturated, branched or unbranched containing from 8 to 20, preferably from 10 to 18 carbon atoms.
  • the alkyl group is a straight chain saturated alkyl group.
  • the alkyl group can contain up to 3 hydroxy groups and/or the polyalkoxide chain can contain up to 30, preferably less than 10, alkoxide moieties.
  • Suitable alkyl polysaccharides are decyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, and octadecyl, di-, tri-, tetra-, penta-, and hexaglucosides, galactosides, lactosides, fructosides, fructosyls, lactosyls, glucosyls and/or galactosyls and mixtures thereof.
  • alkyl polysaccharide surfactant is intended to represent both the preferred glucose and galactose derived surfactants and the less preferred alkyl polysaccharide surfactants.
  • alkyl polyglucoside is used to include alkyl polyglycosides because the stereochemistry of the saccharide moiety is changed during the preparation reaction.
  • APG 625 has: a pH of 6 to 10 (10% of APG 625 in distilled water); a specific gravity at 25°C of 1.1 g/ml; a density at 25°C of 9.1 lbs/gallon; a calculated HLB of 12.1 and a Brookfield viscosity at 35°C, 21 spindle, 5-10 RPM of 3,000 to 7,000 mPa.s (cps).
  • compositions can contain a silk derivatives as part of the composition and generally constitute 0.01 to 3.0 % by weight, preferably 0.1 to 3.0% by weight, most preferably 0.2 to 2.5% by weight of the liquid detergent composition.
  • compositions can contain a viscosity modifying solvent at a concentration of 0.1 to 5.0 weight percent, more preferably 0.5 to 4.0 weight percent.
  • the viscosity modifying agent is an alcohol of the formula wherein
  • the product made will be pourable from a relatively narrow mouth bottle (1.5 cm. diameter) or opening, and the viscosity of the detergent formulation will not be so low as to be like water.
  • the viscosity of the detergent desirably will be at least 100 centipoises (cps) at room temperature, but may be up to 1,000 centipoises as measured with a Brookfield Viscometer using a number 2 spindle rotating at 30 rpm. Its viscosity may approximate those of commercially acceptable detergents now on the market.
  • the detergent viscosity and the detergent itself remain stable on storage for lengthy periods of time, without color changes or settling out of any insoluble materials.
  • the pH of this formation is substantially neutral to skin, e.g., 4.5 to 8 and preferably 5 to 5.5.
  • the compositions of the instant invention are optically clear that is they exhibit a light transmission of at least 95%, more preferably at least 98%.
  • the foam quality and detersive property is equal to or better than standard light duty liquid detergents while using a nonionic surfactant as the primary surfactant and minimal amounts of anionic surfactant, thereby achieving a mild, non-irritating liquid detergent.

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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)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Claims (10)

  1. Une composition détergente liquide très moussante pour lavage délicat à base d'agent tensio-actif non ionique, comprenant, en poids,
    (a) 10 % à 30 % d'un agent tensio-actif non ionique hydrosoluble choisi dans le groupe formé par les produits de condensation d'alcanol en C8-C18 primaire ou secondaire avec 5 à 30 moles d'oxyde d'éthylène, les produits de condensation de (alkyle en C8-C18)phénol avec 5 à 30 moles d'oxyde d'éthylène, les produits de condensation d'alcanol en C8-C20 avec un mélange d'oxyde d'éthylène et d'oxyde de propylène ayant un rapport en poids de l'oxyde d'éthylène à l'oxyde de propylène de 2,5:1 à 4:1 et une teneur totale en oxydes d'alkylène de 60 % à 85 % en poids, et les produits de condensation de 2 à 30 moles d'oxyde d'éthylène avec les mono- et triesters d'acide alcanoïque en C10-C20 du sorbitanne ayant un RHL de 8 à 15 ;
    (b) 1 % à 10 % d'au moins un agent tensio-actif anionique soluble dans l'eau ou dispersable dans l'eau choisi dans le groupe formé par les alkylsulfates en C8-C18, les (alkyle en C8-C16)benzène-sulfonates, les paraffine-sulfonates en C10-C20, les alpha-oléfine-sulfonates en C10-C24 et les (alkyle en C8-C18)-éther-sulfates éthoxylés ;
    (c) 0,5 % à 8 % d'une bétaïne hydrosoluble ;
    (d) 0,5 à 8 % d'un dialkylsulfosuccinate ;
    (e) le reste d'eau sous forme d'un milieu aqueux dans lequel ledit agent tensio-actif non ionique, ledit détergent anionique, ledit dialkylsulfosuccinate et ladite bétaïne sont solubilisés dans ladite eau,
    la composition ne contenant pas d'oxyde d'amine, d'alcanolamide d'acide gras, de carbonate de métal alcalin ou de métal alcalino-terreux, d'épaississants polymères ou argileux, d'argiles, d'abrasifs, d'agents tensio-actifs du type alkylglycine, d'agents tensio-actifs du type imidinium cyclique, de silices, ni plus de 3 % en poids d'acide gras ou de sel métallique d'un acide gras.
  2. Une composition détergente liquide selon la revendication 1, qui comprend, de plus, 1 à 15 % en poids d'un agent solubilisateur choisi dans le groupe formé par les alcanols mono- et dihydroxylés en C2-C3, les sels hydrosolubles d'hydrotropes du type benzène-sulfonate à substitution alkylique en C1-C3, et leurs mélanges.
  3. Une composition détergente liquide selon la revendication 2, dans laquelle de l'éthanol est présent en une quantité de 5 % en poids ou moins.
  4. Une composition détergente liquide selon la revendication 2, dans laquelle ledit agent tensio-actif non ionique est ledit produit de condensation d'un alcanol primaire en C8-C18 avec 5 à 30 moles d'oxyde d'éthylène.
  5. Une composition détergente liquide selon la revendication 4, dans laquelle ledit détergent anionique est choisi dans le groupe formé par les alkylsulfates en C12-C16, les (alkyle en C10-C15)benzène-sulfonates, les paraffine-sulfonates en C12-C17 et les alpha-oléfine-sulfonates en C12-C18.
  6. Une composition détergente liquide selon la revendication 1, dans laquelle ledit détergent anionique est un alkylsulfate en C12-C16.
  7. Une composition détergente liquide selon la revendication 1, contenant de plus un conservateur.
  8. Une composition détergente liquide selon la revendication 1, contenant de plus un stabilisant de couleur.
  9. Une composition détergente liquide selon la revendication 1, dans laquelle la bétaïne est une amidoalkylbétaïne de la formule
    Figure imgb0007
     dans laquelle R est un radical alkyle ayant 9 à 19 atomes de carbone, a est un nombre entier de 1 à 4, chacun de R2 et R3 est un radical alkyle ayant 1 à 3 atomes de carbone et R4 est un radical alkylène ou hydroxyalkylène ayant 1 à 4 atomes de carbone.
  10. Une composition détergente liquide selon la revendication 1, contenant de plus un alkylpolyglucoside de la formule

            R2O(CnH2nO)rZx

    où Z est dérivé du glucose, R est un radical hydrophobe choisi dans le groupe formé par les radicaux alkyle, alkylphényle, hydroxyalkylphényle et leurs mélanges, dans lesquels lesdits radicaux alkyle contiennent 10 à 18 atomes de carbone, n est 2 ou 3, r est de 0 à 10, et x est de 1,5 à 8.
EP94401591A 1993-07-09 1994-07-08 Composition détergente liquide à base de surfactant non ionique très moussant Expired - Lifetime EP0638638B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US91517 1979-11-05
US08/091,514 US5387375A (en) 1992-06-03 1993-07-09 High foaming nonionic surfactant based liquid detergent
US91514 1993-07-09
US08/091,517 US5389304A (en) 1992-06-03 1993-07-09 High foaming nonionic surfactant base liquid detergent

Publications (2)

Publication Number Publication Date
EP0638638A1 EP0638638A1 (fr) 1995-02-15
EP0638638B1 true EP0638638B1 (fr) 1997-06-18

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EP94401591A Expired - Lifetime EP0638638B1 (fr) 1993-07-09 1994-07-08 Composition détergente liquide à base de surfactant non ionique très moussant

Country Status (10)

Country Link
EP (1) EP0638638B1 (fr)
AT (1) ATE154631T1 (fr)
AU (1) AU678007B2 (fr)
CA (1) CA2127348C (fr)
DE (1) DE69403868D1 (fr)
GR (1) GR940100341A (fr)
MX (1) MX9404819A (fr)
NZ (1) NZ260847A (fr)
PT (1) PT101540B (fr)
ZA (1) ZA944973B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150063348A (ko) * 2012-09-25 2015-06-09 라이온 가부시키가이샤 액체 세정제

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7263698A (en) * 1997-05-02 1998-11-27 Colgate-Palmolive Company, The High foaming nonionic surfactant based liquid detergent
ES2258479T3 (es) 1999-10-01 2006-09-01 JOHNSON & JOHNSON CONSUMER COMPANIES, INC. Tecnica que permite calmar a las personas con la ayuda de composiciones de tratamientos personales.
GB2384563A (en) 2002-01-29 2003-07-30 Johnson & Johnson Consumer Method of measuring the stress or relaxation level of a mammal
GB0225668D0 (en) * 2002-11-04 2002-12-11 Unilever Plc Laundry detergent composition
DE60325504D1 (de) 2002-11-04 2009-02-05 Unilever Nv Waschmittel
DE102005031193A1 (de) * 2005-07-01 2007-01-04 Henkel Kgaa Viskositätseinstellung bei Handgeschirrspülmittel

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3950417A (en) * 1975-02-28 1976-04-13 Johnson & Johnson High-lathering non-irritating detergent compositions
US4595526A (en) * 1984-09-28 1986-06-17 Colgate-Palmolive Company High foaming nonionic surfacant based liquid detergent
GB8602589D0 (en) * 1986-02-03 1986-03-12 Unilever Plc Detergent compositions
GB8905551D0 (en) * 1989-03-10 1989-04-19 Unilever Plc Detergent compositions
PT101012B (pt) * 1991-11-07 1999-07-30 Procter & Gamble Composicoes detergentes liquidas que compreendem ingredientes detergentes convencionais e compostos estabilizadores de cor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150063348A (ko) * 2012-09-25 2015-06-09 라이온 가부시키가이샤 액체 세정제

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Publication number Publication date
AU6591994A (en) 1995-01-19
PT101540A (pt) 1995-05-04
EP0638638A1 (fr) 1995-02-15
PT101540B (pt) 1999-12-31
AU678007B2 (en) 1997-05-15
CA2127348A1 (fr) 1995-01-10
GR940100341A (en) 1995-10-31
ZA944973B (en) 1996-01-08
MX9404819A (es) 1995-01-31
ATE154631T1 (de) 1997-07-15
NZ260847A (en) 1996-10-28
DE69403868D1 (de) 1997-07-24
CA2127348C (fr) 2003-03-11

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