US3928251A - Mild shampoo compositions - Google Patents

Mild shampoo compositions Download PDF

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Publication number
US3928251A
US3928251A US313908A US31390872A US3928251A US 3928251 A US3928251 A US 3928251A US 313908 A US313908 A US 313908A US 31390872 A US31390872 A US 31390872A US 3928251 A US3928251 A US 3928251A
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United States
Prior art keywords
group
polyethoxylated
carbon atoms
composition
alkyl
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Expired - Lifetime
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US313908A
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English (en)
Inventor
Jr Raymond Edward Bolich
Robert Benson Aylor
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to US313908A priority Critical patent/US3928251A/en
Priority to CA187,619A priority patent/CA1019679A/en
Priority to DE2361080A priority patent/DE2361080A1/de
Priority to JP48138520A priority patent/JPS4999104A/ja
Priority to GB5728673A priority patent/GB1443960A/en
Application granted granted Critical
Publication of US3928251A publication Critical patent/US3928251A/en
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • C11D1/29—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
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
    • 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

Definitions

  • compositions of this invention are all extremely mild and have minimum or no eye sting. This is a very desirable combination of characteristics. For example, children cannot keep shampoo out of their eyes and the resulting pain can be extremely damaging to good relations between the parent and child. Yet, one would not want to have a shampoo which didnt sting, but which caused serious damage, since then one needs the pain to encourage a thorough rinsing of the eye. Thus, the combination of mildness and lack of eye sting is extremely desirable.
  • compositions discussed hereinbefore do sting the eyes, but less than conventional shampoos.
  • the compositions of this invention are as mild and in many instances milder than the prior art compositions and in many instances sting the eyes less.
  • zwitterionic compounds, of the type disclosed herein are as mild or milder than the reaction prod uct compositions of the prior art, when used in combination with the anionic and nonionic surfactants of this invention.
  • betaines and sultaines are well known in the art, the ability of applicants three-component compositions to be used as shampoos without stinging eyes was unknown.
  • polyethoxylated fatty alcohol sulfosuccinate monoester wherein said fatty alcohol contains from about 8 to about 16 carbon atoms, preferably from about to about 14 carbon atoms, and said polye-' 2 thoxylated fatty alcohol contains from about 1 to about 10 ethoxy moieties per molecule, preferably from about I to 5;
  • a polyethoxylated nonionic surfactant selected from the group consisting of: l) polyethoxylated alcohols, said alcohols containing an alkyl group, either primary or secondary, and either straight or branched chain, containing from about 8 to about 16 carbon atoms and said polyethoxylated alcohols containing from about 10 to about 45 ethoxy moieties per molecule, (2) polyethoxylated alkylphenols wherein the alkyl group contains from about 6 to about 15 carbon atoms and wherein the polyethoxylated alkylphenol contains from about 10 to about 45 ethoxy moieties per molecule, (3) polyethoxylated mono fatty acid esters of sorbitol wherein said fatty acids contain from about 8 to about 18 carbon atoms and said polyethoxylated mono fatty acid ester of sorbitol contains from about 10 to about 45 ethoxy moieties per molecule, (4) polyethoxylated polypropylene glycol, said polye
  • D water, the molecular ratio of (A) to (B) beingfrom about 1:1 to about 4:1; the weight ratio of(A) (B) to (C) being from about 2:1 to about 1:2; and the pH of the composition being from about 6.0 to about 8.0.
  • composition will contain from.
  • anionic surfactant preferably from about 4 to about 8 7c for a liquid shampoo, and from about 3 to about for a paste shampoo.
  • the sodium salts of the polyethoxylated anionic surfactants are preferred, but any non-toxic, water-soluble salt can be used, including potassium, triethanolammonium. and ammonium salts.
  • the preferred polyethoxylated anionic surfactants are the sodium salt of C -C fatty alcohol polyethoxy(3) ether sulfate, the sodium salt of polyethoxylated(3) C -C mono fatty alcohol sulfosuccinate, and the sodium salt of C -C fatty acyl amido polyethoxy(4) ether sulfate.
  • Other suitable polyethoxylated anionic surfactants are disclosed hereinafter in the examples.
  • the zwitterionic surfactant provides major lather benefits while modifying the nature of the composition so that it is less strongly anionic.
  • the molecular ratio of the anionic to zwitterionic surfactant is from about 1:1 to about 4:1, preferably from about 1:1 to about 3:1, most preferably from about 1:1 to about 2:1.
  • Preferred zwitterionic surfactants are propylamido betaines derived from C -C fatty acids, and the corresponding propylamido sultaines, and C -C alkyl sultaines wherein the cationic and sulfonate anionic groups are separated by a propylene group and the remaining groups are methyl groups.
  • preferred zwitterionic surfactants are (a) those having the formula R7CONH- C H NH (RR)?
  • R Y wherein R is an alkyl group containing from about 9 to about carbon atoms, wherein each R is selected from the group consisting of methyl, ethyl, and 2- hydroxyethyl groups, wherein Y is selected from the group consisting of sulfonate and carboxylate groups, and wherein R is a methylene group when Y is a carboxylate group and is selected from the group consisting of propylene and 2-hydroxypropylene groups when Y is a sulfonate group; and (b) those having the formula R'ONH 1R”)!
  • R contains from about 10 to about 16 carbon atoms, wherein each R is selected from the group consisting of methyl, ethyl, and 2-hydroxyethyl groups, and wherein X is selected from the group consisting of hydrogen and hydroxyl groups.
  • R contains from about 10 to about 16 carbon atoms, wherein each R is selected from the group consisting of methyl, ethyl, and 2-hydroxyethyl groups, and wherein X is selected from the group consisting of hydrogen and hydroxyl groups. Examples of other zwitterionic surfactants are given in the examples hereinafter.
  • the polyethoxylated nonionic surfactant provides a mildness benefit. It also contributes to the character of the lather, although in general, the nonionic surfactant tends to control and diminish the amount of the lather.
  • the ratio of the polyethoxylated anionic surfactant and zwitterionic surfactant to the polyethoxylated nonionic surfactant is from about 2:1 to about 1:2, preferably from about 1:1 to about 1:2, and most preferably from about 1:1 to about 121.2.
  • Preferred nonionic surfactants include polyethoxylated (15-40) sorbitan monoacylate (C -C preferably monolaurate), polyethoxylated (20-100) polypropylene glycol (M.W. 8,000l2,000), and polyethoxylated (15-40) fatty alcohols (C -C Other examples of nonionic surfactants are disclosed hereinafter in the examples.
  • Water Water is used to make up the shampoo compositions to the desired physical form.
  • For a paste shampoo there will normally be from about 30 to about 60% water present, preferably from about 35 to about 55% 5.
  • Other ingredients in addition to the ingredients described hereinbefore, the shampoo compositions of this invention can also contain other conventional shampoo components, including dyes, preservatives such as ethanol, perfumes, thickeners, opacifiers, antibacterial agents, antidandruff agents, buffering agents, conditioning agents, etc. Desirably, only ingredients which are not irritating to the eye are added.
  • buffering agents present to maintain the pH of the composition within the range from about 6.0 to about 8.0, preferably from about 6.5 to about 7.5, and most preferably, about 7.
  • buffering agents include NaOH, NCl, NaHPO,,, boric acid, etc.
  • antidandruff agents such as zinc pyridinethiol N-oxide.
  • Suitable thickening agents include carragenan, hydroxyethyl cellulose (e.g., one with a D3. of about 2,5 whose 1% solution has a viscosity of 3-4,000 centipoises at 25C.), and the compounds disclosed in US. Pat. No. 3,472,840, F. W. Stone and J. M. Rutherford, Jr., as set forth in the application of Roger Clarence Birkofer, Ser. No.
  • Cationic thickener 2 [cationic cellulose L ether of Claim 7 of US. Pat. No. 3.472.840, wherein a is 2, h is 2. q is 0 m p is about l.5. the degree of substitution of the cationic group (and m) are about 0.2. and the viscosity of a Wr aqueous solution is I25-I500 eentipoises at 25C.]
  • EXAMPLE VIII Ingredient '/t by Weight 3-( N,N-dimethyl-N-eoeonutalkylammonio Z-hydroxypropane sull'onat'e- Ethoxylated amidosull'ate Tween 20 Natrosol 250 HH Ethanol Water pH adjusted to 7.0 with NaOH.
  • Distilled water balance Adjusted pH to 7.0 with HCl.
  • Distilled water balance Adjusted pH to 7.0 with HCI.
  • Distilled water balance Adjusted pH to 7.0 with NaOH.
  • Polyethoxylated(40)octanol Polyethoxylated( l0 )hexadecanol; Polyethoxylated( 25 )2-ethylnonanol; Polyethoxylated( 1 8 )dodecane-2-ol; Polyethoxylated( 35 )hexylphenol; Polyethoxylated(30)pentadecylphenol; Polyethoxylated(40)tetrapropylenephenol; P0lyethoxylated(25 )3-nonylphenol; Polyethoxylated(35 )sorbitan monostearate; l0. Polyethoxylated( 25 )sorbitan monooctanoate; l l. Polyethoxylated(25 )polypropylene glycol (M.W.
  • a mild shampoo composition comprising surfactants and water, said surfactants consisting of a mixture of:
  • a polyethoxylated nonionic surfactant selected from the group consisting of: (l) polyethoxylated alkyl alcohols, said alkyl alcohols containing an alkyl group containing from about 8 to about 16 carbon atoms and said polyethoxylated alkyl alcohols containing from about 10 to about 45 ethoxy moieties per molecule, (2) polyethoxylated alkylphenols wherein the alkyl group contains from about 6 to about carbon atoms and wherein the polyethoxylated alkylphenol contains from about 10 to about 45 ethoxy moieties per molecule, (3) polyethoxylated mono fatty acid esters of sorbitol wherein said fatty acids contain from about 8 to about 18 carbon atoms and said polyethoxylated mono fatty acid ester of sorbitol contains from about 10 to about 45 ethoxy moieties per molecule, (4) polyethoxylated polypropylene glycol, said glycol polypropylene glycol,
  • composition of claim 2 wherein the molecular ratio of the anionic surfactant to the zwitterionic surfactant is from about 1:1 to about 3:1.
  • composition of claim 2 wherein the molecular ratio of the anionic surfactant to the zwitterionic surfactant is from about 1:1 to about 2:1.
  • composition of claim 1 having a pH of about 7.0.
  • composition of claim 1 wherein the zwitterionic surfactant has the formula wherein R is an alkyl group containing from about 9 to about 15 carbon atoms, wherein each R is selected from the group consisting of methyl, ethyl, and 2- hydroxyethyl groups, wherein Y is selected from the group consisting of sulfonate and carboxylate groups, and wherein R is a methylene group when Y is a carboxylate group and is selected from the group consisting of propylene and 2-hydroxypropylene groups when Y is a sulfonate group.
  • composition of claim 1 wherein the zwitterionic surfactant has the formula R'N"" (R )g CH CHX CH-ZSOKH wherein R contains from about 10 to about 16 carbon atoms, wherein each R is selected from the group consisting of methyl, ethyl, and 2-hydroxyethyl groups, and wherein X is selected from the group consisting of hydrogen and hydroxyl groups.
  • composition of claim 1 wherein the anionic surfactant is a sodium salt of a fatty alcohol polyethoxy ether sulfate containing a fatty alkyl group containing from about 10 to about 14 carbon atoms and about 3 ethoxy moieties per molecule.
  • nonionic surfactant is a polyethoxylataed mono fatty acid ester of sorbitol wherein the fatty acid contains from about 10 to about 16 carbon atoms and wherein there are from about 15 to about 40 ethoxy moieties per molecule.
  • composition of claim 12 wherein the fatty acid is lauric acid.
  • nonionic surfactant is a polyethoxylated alkyl alcohol wherein said alkyl alcohol contains from about 10 to about 14 carbon atoms and wherein there are from l2 16.
  • anionic surfactant is a sodium salt of a polyethoxylated fatty alcohol sulfosuccinate monoestcr. wherein said fatty alcohol contains from about 10 to about 14 carbon atoms and said polyethoxylated fatty alcohol contains about 3 ethoxy moieties per molecule.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
US313908A 1972-12-11 1972-12-11 Mild shampoo compositions Expired - Lifetime US3928251A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US313908A US3928251A (en) 1972-12-11 1972-12-11 Mild shampoo compositions
CA187,619A CA1019679A (en) 1972-12-11 1973-12-06 Mild shampoo compositions
DE2361080A DE2361080A1 (de) 1972-12-11 1973-12-07 Mildes shampoo
JP48138520A JPS4999104A (enrdf_load_stackoverflow) 1972-12-11 1973-12-11
GB5728673A GB1443960A (en) 1972-12-11 1973-12-11 Mild shampoo compositions card system of charge counter

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JP (1) JPS4999104A (enrdf_load_stackoverflow)
CA (1) CA1019679A (enrdf_load_stackoverflow)
DE (1) DE2361080A1 (enrdf_load_stackoverflow)
GB (1) GB1443960A (enrdf_load_stackoverflow)

Cited By (48)

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US4087387A (en) * 1973-07-10 1978-05-02 Lever Brothers Company Foam cleaning composition
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US4137191A (en) * 1977-02-14 1979-01-30 Inolex Corporation Low-irritant surfactant composition
US4138371A (en) * 1976-04-07 1979-02-06 Gaf Corporation Washing method using amphoteric surface active agents
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US5529721A (en) * 1993-04-20 1996-06-25 Henkel Corporation Liquid pearlizing composition
US5531933A (en) * 1993-12-30 1996-07-02 The Procter & Gamble Company Liquid hard surface detergent compositions containing specific polycarboxylate detergent builders
US5534198A (en) * 1994-08-02 1996-07-09 The Procter & Gamble Company Glass cleaner compositions having good filming/streaking characteristics and substantive modifier to provide long lasting hydrophilicity
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US5540864A (en) * 1990-12-21 1996-07-30 The Procter & Gamble Company Liquid hard surfce detergent compositions containing zwitterionic detergent surfactant and monoethanolamine and/or beta-aminoalkanol
WO2003010222A1 (de) * 2001-07-25 2003-02-06 Clariant Gmbh Umsetzungsprodukte von langkettigen carbonsäuren
US6677294B2 (en) 2000-11-29 2004-01-13 The Procter & Gamble Company Cleansing compositions
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GB1584364A (en) * 1976-06-21 1981-02-11 Unilever Ltd Shampoo
JPS60197614A (ja) * 1984-03-21 1985-10-07 Shionogi & Co Ltd 低刺激性シヤンプ−組成物
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NZ260848A (en) * 1993-07-09 1996-08-27 Colgate Palmolive Co High foaming liquid detergent comprising as nonionic surfactant an alkyl or fatty acid sorbitan ether with an ethylene oxide condensate, or an alkylphenolether of an ethylene oxide/propylene oxide condensate, a betaine and an ethoxylated alkyl ether sulphate
JP5426213B2 (ja) * 2009-03-31 2014-02-26 花王株式会社 水性毛髪洗浄剤
JP5426212B2 (ja) * 2009-03-31 2014-02-26 花王株式会社 水性毛髪洗浄剤
DE102015207735A1 (de) * 2015-04-28 2016-11-03 Henkel Ag & Co. Kgaa Sulfobetainhaltige Wasch- und Reinigungsmittel

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US5336446A (en) * 1989-02-21 1994-08-09 Goodman Robert M Compositions and process for non-irritating dense foaming of bath water and peri-vaginal cleaning
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US4992266A (en) * 1989-08-14 1991-02-12 S. C. Johnson & Son, Inc. Reducing the ocular irritancy of anionic shampoos
US5342549A (en) * 1990-01-29 1994-08-30 The Procter & Gamble Company Hard surface liquid detergent compositions containing hydrocarbyl-amidoalkylenebetaine
US5540865A (en) * 1990-01-29 1996-07-30 The Procter & Gamble Company Hard surface liquid detergent compositions containing hydrocarbylamidoalkylenebetaine
US5336445A (en) * 1990-03-27 1994-08-09 The Procter & Gamble Company Liquid hard surface detergent compositions containing beta-aminoalkanols
US5540864A (en) * 1990-12-21 1996-07-30 The Procter & Gamble Company Liquid hard surfce detergent compositions containing zwitterionic detergent surfactant and monoethanolamine and/or beta-aminoalkanol
US5454983A (en) * 1992-01-23 1995-10-03 The Procter & Gamble Company Liquid hard surface detergent compositions containing zwitterionic and cationic detergent surfactants and monoethanolamine and/or beta-aminoalkanol
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US5529721A (en) * 1993-04-20 1996-06-25 Henkel Corporation Liquid pearlizing composition
US5536450A (en) * 1993-11-12 1996-07-16 The Procter & Gamble Comany Liquid hard surface detergent compositions containing amphoteric detergent surfactant and perfume
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US6677294B2 (en) 2000-11-29 2004-01-13 The Procter & Gamble Company Cleansing compositions
US20050085405A1 (en) * 2000-11-29 2005-04-21 The Procter & Gamble Company Cleansing compositions
US20060058207A1 (en) * 2000-11-29 2006-03-16 Shaw Gretchen L Cleansing compositions
WO2003010222A1 (de) * 2001-07-25 2003-02-06 Clariant Gmbh Umsetzungsprodukte von langkettigen carbonsäuren
US20040121782A1 (en) * 2002-09-07 2004-06-24 Offshore Data Services, Llc Personal flotation device transceiver tracking system
CN102361628A (zh) * 2009-03-31 2012-02-22 花王株式会社 水性毛发清洗剂
CN102361628B (zh) * 2009-03-31 2013-07-10 花王株式会社 水性毛发清洗剂
EP2583666A4 (en) * 2010-06-18 2015-05-27 Kao Corp AQUEOUS HAIR DETERGENT

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DE2361080A1 (de) 1974-06-12
CA1019679A (en) 1977-10-25
JPS4999104A (enrdf_load_stackoverflow) 1974-09-19
GB1443960A (en) 1976-07-28

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