WO1994018934A1 - Hair care compositions containing a silicone compound and a quaternary ammonium compound - Google Patents

Hair care compositions containing a silicone compound and a quaternary ammonium compound Download PDF

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Publication number
WO1994018934A1
WO1994018934A1 PCT/EP1994/000551 EP9400551W WO9418934A1 WO 1994018934 A1 WO1994018934 A1 WO 1994018934A1 EP 9400551 W EP9400551 W EP 9400551W WO 9418934 A1 WO9418934 A1 WO 9418934A1
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Prior art keywords
composition
quaternary ammonium
hair
weight
amount
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Application number
PCT/EP1994/000551
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French (fr)
Inventor
Susan Victoria Cooper
Diane Catherine Powell
Original Assignee
The Boots Company Plc
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 The Boots Company Plc filed Critical The Boots Company Plc
Priority to AU62064/94A priority Critical patent/AU6206494A/en
Publication of WO1994018934A1 publication Critical patent/WO1994018934A1/en

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Classifications

    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • 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
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a toiletries composition in the form of a hair care composition having conditioning properties , and to methods of manufacturing and using such a composition .
  • hair care composition includes so-called “hot oil” treatments , shampoos , conditioners , hair dyes , mousses , foams , gels , creams , lotions and rinses , all suitable for use on the human head .
  • Hair care compositions comprising water soluble quaternary ammonium compounds, as conditioning agents, are well known in the art.
  • GB-A-1538768 (Alberto Culver) discloses a method of treating hair to improve its manageability, by contacting the hair with an aqueous composition comprising a water soluble quaternary ammonium compound (having one or two nitrogen atoms and at least one long chain alkyl group linked to one or both of the nitrogen atom(s)), and then shampooing the hair.
  • a water soluble quaternary ammonium compound having one or two nitrogen atoms and at least one long chain alkyl group linked to one or both of the nitrogen atom(s)
  • Silicone copolyols are also known for use in hair care compositions.
  • P Union Carbide has described the use of dimethicone copolyols (available under the registered trade name "Silwet”) in hair sprays (as plasticisers and as wetting and levelling agents) , in shampoos (to give profoaming activity and improved wettability and lubricity) , in after shampoo preparations (to give improved wettability and lubricity) , and in hair fixatives/dressings (as wetting agents and pump valve lubricants) .
  • Dimethicone copolyols available under the registered trade name "Silwet”
  • hair sprays as plasticisers and as wetting and levelling agents
  • shampoos to give profoaming activity and improved wettability and lubricity
  • after shampoo preparations to give improved wettability and lubricity
  • hair fixatives/dressings as wetting agents and pump valve lubricants
  • Avon cosmetics have marketed a so-called "hot oil” conditioning treatment comprising a dimethicone copolyol.
  • the product is in the form of a lotion which is designed to turn from cloudy to clear when immersed in hot water prior to use.
  • the Boots Company PLC has marketed another so-called "hot oil" conditioning treatment comprising the agent available under the CTFA designation stearalkonium chloride.
  • the packaged product is intended to be heated by immersion in hot water prior to use.
  • the product turns from cloudy to clear at the optimum temperature for use and this transition indicates to the user that the product is at the correct temperature.
  • GB-A-2205 747 (Colgate - Palmolive) discloses a stable easily removable hair rinse conditioner comprising a short chain quaternary ammonium compound, a c i4-22 alkanol and about 0.5 to 1.5% by weight of a cyclic or linear silicone.
  • EP-A-0155806 (Procter and Gamble) discloses a hair conditioning composition comprising inter alia 0.01% to
  • silicone copolyols having a cloud point (in water at 4% by weight) of between 20°C and 60°C provide improved substantivity in hair care compositions when included in an amount of at least about 4% by weight of the composition.
  • a hair care composition comprising a cosmetically acceptable silicone copolyol having a cloud point (in water at 4% by weight) of between about 20°C and about 60°C, in an amount of at least about 4% by weight of the composition and a conditioning amount of a cosmetically acceptable quaternary ammonium compound.
  • cloud point denotes the temperature at which there is a sudden change in solubility at a given concentration (typically about 4% w/w) .
  • the silicone copolyol has a cloud point of between about 20°C and about 55°C, preferably between about 23°C and about 50°C, preferably between about 27°C and about 45°C.
  • the silicone copolyol is present in an amount of from about 4% to about 20%, preferably about 5% to about 10%, preferably about 6% to about 7% by weight of the composition.
  • the silicone copolyol is a dimethicone copolyol, such as those available commercially under the trade names "Abil” (from T H Goldschmidt) and "Silwet” (from Union Carbide) .
  • the cosmetically acceptable quaternary ammonium compound has the formula + A-, wherein R- ⁇ is g.- ⁇ g alkyl; R2 is C- ] __ 18 alkyl; R3 is c l-18 a lky3- or benzyl; R4 is C- ] __3 alkyl or benzyl; and A is an anion.
  • R- j _ is - ] _o_2o alkyl, suitably C 12 -i6 alkyl, suitably C ⁇ g alkyl; R 2 to R 4 are each methyl and A is a chloride ion or a bromide ion.
  • the quaternary ammonium compound is cetyl trimethyl ammonium chloride (also known under the CTFA designation "cetrimonium chloride”) cetyl trimethyl ammonium bromide, lauryl trimethyl ammonium chloride or lauryl trimethyl ammonium bromide.
  • the quaternary ammonium compound is present in an amount of from about 0.5% to about 5%, preferably from about 0.5% to about 3%, suitably about 0.5% to 1% by weight of the composition.
  • the silicone copolyol is chosen such that the composition undergoes a transition from clear to cloudy at or around the optimum temperature for use, thereby indicating to the user that the optimum temperature for use has been reached.
  • the optimum temperature for use is from about 20°C to about 45°C.
  • the composition further comprises a polymeric quaternary ammonium salt of hydroxyethyl cellulose reacted with a trimethyl ammonium substituted epoxide (also known under the CTFA designation
  • preservatives may be present, such as bronopol, benzyl alcohol, imidazolidinyl urea, methyl paraben and propyl paraben, suitably in an amount of from about 0.01% to about 2% by weight of the composition.
  • Thickeners and viscosity modifying agents may be present, such as amine oxides, block polymers of ethylene oxide and propylene oxide (for example, those available from BASF Wyandotte under the trade name "Pluronic"), polyvinyl alcohols and fatty alcohols, suitably in an amount of from about 0.5% to about 10% by weight of the composition.
  • Sequestering agents may be present, such as ethy enediamine tetraacetic acid and salts thereof, suitably in an amount of from about 0.005 % to about 0.5% by weight of the composition.
  • Perfumes may be present suitably in an amount of from about 0.01% to about 2%, as may water soluble dyes such as tartrazine, suitably in an amount of from about 0.00001% to about 0.1% by weight of the composition.
  • the composition may be buffered by means well known in the art, for example by use of buffer systems comprising succinic acid, citric acid, lactic acid, phosphoric acid, mono- or disodium phosphoric and sodium carbonate.
  • buffer systems comprising succinic acid, citric acid, lactic acid, phosphoric acid, mono- or disodium phosphoric and sodium carbonate.
  • the composition may have a pH between about 3 and about 10, preferably between about 4 and about 6.
  • the composition may also include an antidandruff agent such as salicyclic acid or zinc pyrithione suitably in an amount of from about 0.1% to about 5% by weight.
  • an antidandruff agent such as salicyclic acid or zinc pyrithione suitably in an amount of from about 0.1% to about 5% by weight.
  • the composition is a conditioning treatment substantially free of shampoo surfactants such as soaps and/or sulphate detergents.
  • the composition finds particular application as a so called “hot oil treatment” which may be heated to a desired temperature and applied to the hair either before or after shampooing.
  • the invention further provides a method of treating the hair by heating a composition as defined above, and then applying the heated composition to the hair.
  • the method includes treatment with a separate shampoo product either before or after treatment with the composition, preferably after treatment.
  • the composition is heated at least to the cloud point of the silicone copolyol (in water at 4% w/w) which is suitably between about 20°C and about
  • the present invention also provides the use of a silicone copolyol as defined above in a hair care composition to improve substantivity to the hair.
  • Polyquaternium 10 1 (available from Union Carbide under the trade name "Polymer JR 400")
  • Example 1 The above composition (Example 1) was compared with a sample (Example A) having exactly the same composition except that it did not include the dimethicone copolyol .
  • the two products were evaluated in a half head trial. Each trialist had their hair assessed by 10 trained evaluators for shine, feel, and control after the treatment had been applied and the hair shampooed and dried. Each evaluator assessed each of the two formulations for "shine”, “feel” and “control”, and in each case either "voted” for whichever formulation gave the better result in respect of that characteristic, or reported that there was no difference.
  • Example 1 The composition of Example 1 was also compared in similar manner with a sample (Example B) having exactly the same composition except that it did not include the quaternary ammonium compound (cetrimonium chloride) .
  • the mean results were as follows:- EVALUATORS' SCORES
  • the figures show (for each characteristic) the relative numbers of evaluators preferring each formula and those detecting no difference.

Abstract

A hair care composition comprises a cosmetically acceptable silicone copolyol having a cloud point (in water at 4 % by weight) of between about 20 °C and about 60 °C, in an amount of at least about 4 % by weight of the composition and a conditioning amount of a cosmetically acceptable quaternary ammonium compound.

Description

HAIR CARE COMPOSITIONS CONTAINING A SILICONE COMPOUND AND A QUATERNARY AMMONIUM COMPOUND
The present invention relates to a toiletries composition in the form of a hair care composition having conditioning properties , and to methods of manufacturing and using such a composition .
The term "hair care composition" as used herein includes so-called "hot oil " treatments , shampoos , conditioners , hair dyes , mousses , foams , gels , creams , lotions and rinses , all suitable for use on the human head .
Hair care compositions comprising water soluble quaternary ammonium compounds, as conditioning agents, are well known in the art.
For example, GB-A-1538768 (Alberto Culver) discloses a method of treating hair to improve its manageability, by contacting the hair with an aqueous composition comprising a water soluble quaternary ammonium compound (having one or two nitrogen atoms and at least one long chain alkyl group linked to one or both of the nitrogen atom(s)), and then shampooing the hair.
Silicone copolyols are also known for use in hair care compositions.
For example, in its trade literature, TH Goldschmidt AG has described the use of silicone copolyols in the form of dimethicone copolyols
(available under the registered trade name "Abil") as water soluble additives which improve combing properties. The compounds are recommended for use at levels of from 0.5% to 3%.
P Union Carbide has described the use of dimethicone copolyols (available under the registered trade name "Silwet") in hair sprays (as plasticisers and as wetting and levelling agents) , in shampoos (to give profoaming activity and improved wettability and lubricity) , in after shampoo preparations (to give improved wettability and lubricity) , and in hair fixatives/dressings (as wetting agents and pump valve lubricants) .
Avon cosmetics have marketed a so-called "hot oil" conditioning treatment comprising a dimethicone copolyol. The product is in the form of a lotion which is designed to turn from cloudy to clear when immersed in hot water prior to use.
The Boots Company PLC has marketed another so- called "hot oil" conditioning treatment comprising the agent available under the CTFA designation stearalkonium chloride. The packaged product is intended to be heated by immersion in hot water prior to use. The product turns from cloudy to clear at the optimum temperature for use and this transition indicates to the user that the product is at the correct temperature.
GB-A-2205 747 (Colgate - Palmolive) discloses a stable easily removable hair rinse conditioner comprising a short chain quaternary ammonium compound, a ci4-22 alkanol and about 0.5 to 1.5% by weight of a cyclic or linear silicone.
EP-A-0155806 (Procter and Gamble) discloses a hair conditioning composition comprising inter alia 0.01% to
10% of a dimethicone copolyol, 0.1% to 10% of a silicone conditioning agent and 0.05% to 5% of a cationic surfactant vehicle material. It has now been found that silicone copolyols having a cloud point (in water at 4% by weight) of between 20°C and 60°C provide improved substantivity in hair care compositions when included in an amount of at least about 4% by weight of the composition.
According to the present invention, there is provided a hair care composition comprising a cosmetically acceptable silicone copolyol having a cloud point (in water at 4% by weight) of between about 20°C and about 60°C, in an amount of at least about 4% by weight of the composition and a conditioning amount of a cosmetically acceptable quaternary ammonium compound. The term "cloud point" as used herein denotes the temperature at which there is a sudden change in solubility at a given concentration (typically about 4% w/w) .
Preferably, the silicone copolyol has a cloud point of between about 20°C and about 55°C, preferably between about 23°C and about 50°C, preferably between about 27°C and about 45°C.
Suitably, the silicone copolyol is present in an amount of from about 4% to about 20%, preferably about 5% to about 10%, preferably about 6% to about 7% by weight of the composition.
Preferably, the silicone copolyol is a dimethicone copolyol, such as those available commercially under the trade names "Abil" (from T H Goldschmidt) and "Silwet" (from Union Carbide) .
Preferably, the cosmetically acceptable quaternary ammonium compound has the formula
Figure imgf000005_0001
+ A-, wherein R-^ is g.-^g alkyl; R2 is C-]__18 alkyl; R3 is cl-18 alky3- or benzyl; R4 is C-]__3 alkyl or benzyl; and A is an anion.
Preferably, R-j_ is -]_o_2o alkyl, suitably C12-i6 alkyl, suitably C^g alkyl; R2 to R4 are each methyl and A is a chloride ion or a bromide ion.
Suitably, the quaternary ammonium compound is cetyl trimethyl ammonium chloride (also known under the CTFA designation "cetrimonium chloride") cetyl trimethyl ammonium bromide, lauryl trimethyl ammonium chloride or lauryl trimethyl ammonium bromide.
Suitably, the quaternary ammonium compound is present in an amount of from about 0.5% to about 5%, preferably from about 0.5% to about 3%, suitably about 0.5% to 1% by weight of the composition.
Preferably, the silicone copolyol is chosen such that the composition undergoes a transition from clear to cloudy at or around the optimum temperature for use, thereby indicating to the user that the optimum temperature for use has been reached.
Normally, the optimum temperature for use is from about 20°C to about 45°C.
Preferably, the composition further comprises a polymeric quaternary ammonium salt of hydroxyethyl cellulose reacted with a trimethyl ammonium substituted epoxide (also known under the CTFA designation
"polyquaternium 10").
Further components may be added to the hair-care composition as is well-known in the art. For example, preservatives may be present, such as bronopol, benzyl alcohol, imidazolidinyl urea, methyl paraben and propyl paraben, suitably in an amount of from about 0.01% to about 2% by weight of the composition.
Thickeners and viscosity modifying agents may be present, such as amine oxides, block polymers of ethylene oxide and propylene oxide (for example, those available from BASF Wyandotte under the trade name "Pluronic"), polyvinyl alcohols and fatty alcohols, suitably in an amount of from about 0.5% to about 10% by weight of the composition.
Sequestering agents may be present, such as ethy enediamine tetraacetic acid and salts thereof, suitably in an amount of from about 0.005 % to about 0.5% by weight of the composition.
Perfumes may be present suitably in an amount of from about 0.01% to about 2%, as may water soluble dyes such as tartrazine, suitably in an amount of from about 0.00001% to about 0.1% by weight of the composition.
The composition may be buffered by means well known in the art, for example by use of buffer systems comprising succinic acid, citric acid, lactic acid, phosphoric acid, mono- or disodium phosphoric and sodium carbonate. Suitably, the composition may have a pH between about 3 and about 10, preferably between about 4 and about 6.
The composition may also include an antidandruff agent such as salicyclic acid or zinc pyrithione suitably in an amount of from about 0.1% to about 5% by weight. Preferably, the composition is a conditioning treatment substantially free of shampoo surfactants such as soaps and/or sulphate detergents. The composition finds particular application as a so called "hot oil treatment" which may be heated to a desired temperature and applied to the hair either before or after shampooing.
Thus, the invention further provides a method of treating the hair by heating a composition as defined above, and then applying the heated composition to the hair.
Preferably, the method includes treatment with a separate shampoo product either before or after treatment with the composition, preferably after treatment.
Suitably, the composition is heated at least to the cloud point of the silicone copolyol (in water at 4% w/w) which is suitably between about 20°C and about
55°C; preferably between about 23°C and about 50°C; preferably between about 27°C and about 45°C.
The present invention also provides the use of a silicone copolyol as defined above in a hair care composition to improve substantivity to the hair.
The invention will be understood with reference to the following non-limiting test and example: EXAMPLE 1
"HOT OIL" CONDITIONING TREATMENT
COMPONENT CONCENTRATION (% W/W)
Polyquaternium 10 1 (available from Union Carbide under the trade name "Polymer JR 400")
Cetrimonium chloride 0.75 (active)
(available from Henkel under the trade name "Dehyquart A")
Dimethicone copolyol 7
(available from T H Goldschmidt under the trade name
"Abil B 8873") Panthenol 0.1
(available from BASF under the trade name "D-Panthenol 75L")
Polysorbate 20 0.5
(available from ICI PLC under the trade name "Tween 20")
Fragrance 0.5
2-Bromo-2-nitropropane-l,3-diol 0.02
(available from The Boots Company PLC under the name "Bronopol")
Water to 100
COMPARATIVE TEST
The above composition (Example 1) was compared with a sample (Example A) having exactly the same composition except that it did not include the dimethicone copolyol .
The two products were evaluated in a half head trial. Each trialist had their hair assessed by 10 trained evaluators for shine, feel, and control after the treatment had been applied and the hair shampooed and dried. Each evaluator assessed each of the two formulations for "shine", "feel" and "control", and in each case either "voted" for whichever formulation gave the better result in respect of that characteristic, or reported that there was no difference.
The mean results were as follows :-
EVALUATORS' SCORES
EXAMPLE 1 EXAMPLE A
(WITHOUT NO
DIMETHICONE DIFFERENCE
COPOLYOL)
SHINE 2.7 1.7 5.7
FEEL 4.0 3.3 2.7
CONTROL 2.3 1.3 6.3
TOTAL
SCORE 9.0 6.3 14.7
MEAN
SCORE 3.0 2.1 4.9
The composition of Example 1 was also compared in similar manner with a sample (Example B) having exactly the same composition except that it did not include the quaternary ammonium compound (cetrimonium chloride) . The mean results were as follows:- EVALUATORS' SCORES
EXAMPLE 1 EXAMPLE B
(WITHOUT NO
QUATERNARY DIFFERENCE
AMMONIUM
COMPOUND)
SHINE 4.0 2.0 4.0
FEEL 4.5 1.0 4.5
CONTROL 2.0 1.5 6.5
TOTAL
SCORE 10.5 4.5 15.0
MEAN
SCORE 3.5 1.5 5.0
The figures show (for each characteristic) the relative numbers of evaluators preferring each formula and those detecting no difference.
These results show that the combination of a suitable dimethicone copolyol and a water soluble quaternary ammonium compound gives superior conditioning properties suggesting a synergistic effect.

Claims

1) A hair care composition comprising a cosmetically acceptable silicone copolyol having a cloud point (in water at 4% by weight) of between about 20°C and about 60°C, in an amount of at least about 4% by weight of the composition, and a conditioning amount of a cosmetically acceptable quaternary ammonium compound.
2) A composition as claimed in claim 1 wherein the silicone copolyol has a cloud point of between about 23°C and about 50°C.
3) A composition as claimed in claim 1 or claim 2 wherein the silicone copolyol is present in am amount of from about 4% to about 20% by weight of the composition.
4) A composition as claimed in any one of the preceding claims wherein the silicone copolyol is a dimethicone copolyol.
5) A composition as claimed in any one of the preceding claims wherein the cosmetically acceptable quaternary ammonium compound has the formula
(NR^Rβl^) +A 71 -
wherein R-]_ is Cg_-]_g alkyl; R2 is C^^g alkyl; R is l-18 alky! or benzyl; R4 is C-]__3 alkyl or benzyl; and A is an anion.
6) A composition as claimed in Claim 5 wherein R^ is ci2-16 alkyl, R2 to R4 are each methyl and A is either a chloride ion or a bromide ion. 7) A composition as claimed in any one of the preceding claims wherein the quaternary ammonium compound is present in an amount of from about 0.5 to about 5% by weight of the composition.
8) A composition as claimed in any one of the preceding claims further comprising a polymeric quaternary ammonium salt of hydroxyethyl cellulose reacted with a trimethyl ammonium substituted epoxide.
9) A composition as claimed in any one of the preceding claims which is substantially free of shampoo- type surfactants.
10) A method of treating hair by heating a composition as claimed in any one of claims 1 to 9 to at least the cloud point of the silicone copolyol and then applying the heated composition to the hair.
11) A method as claimed in Claim 9 wherein the hair is subsequently treated with a detergent composition.
PCT/EP1994/000551 1993-02-26 1994-02-24 Hair care compositions containing a silicone compound and a quaternary ammonium compound WO1994018934A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU62064/94A AU6206494A (en) 1993-02-26 1994-02-24 Hair care compositions containing a silicone compound and a quaternary ammonium compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9303889.1 1993-02-26
GB939303889A GB9303889D0 (en) 1993-02-26 1993-02-26 Toiletries composition

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5759527A (en) * 1996-10-02 1998-06-02 Colgate-Palmolive Company Hair conditioning composition
WO2000000170A1 (en) * 1998-06-29 2000-01-06 The Procter & Gamble Company Hair shampoo and conditioner system
FR2785799A1 (en) * 1998-11-12 2000-05-19 Oreal COSMETIC CONDITIONING AND DETERGENT COMPOSITION COMPRISING A CARBOXYLIC SURFACTANT, A SILICONE AND A CATIONIC POLYMER, USE AND METHOD.
US6495498B2 (en) 1999-05-27 2002-12-17 Johnson & Johnson Consumer Companies, Inc. Detergent compositions with enhanced depositing, conditioning and softness capabilities
WO2017165112A1 (en) * 2016-03-22 2017-09-28 Kao Usa, Inc. Clear hair conditioner composition

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JPS63188617A (en) * 1987-01-29 1988-08-04 Shiseido Co Ltd Transparent gelatinous hair treatment composition
GB2211192A (en) * 1987-12-18 1989-06-28 Oreal Composition and process for the treatment and care of the hair
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GB2066659A (en) * 1980-01-09 1981-07-15 Kao Corp Hair rinse compositions
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5759527A (en) * 1996-10-02 1998-06-02 Colgate-Palmolive Company Hair conditioning composition
WO2000000170A1 (en) * 1998-06-29 2000-01-06 The Procter & Gamble Company Hair shampoo and conditioner system
FR2785799A1 (en) * 1998-11-12 2000-05-19 Oreal COSMETIC CONDITIONING AND DETERGENT COMPOSITION COMPRISING A CARBOXYLIC SURFACTANT, A SILICONE AND A CATIONIC POLYMER, USE AND METHOD.
EP1004291A1 (en) * 1998-11-12 2000-05-31 L'oreal Conditioning and detergent composition, its use
US6410493B1 (en) 1998-11-12 2002-06-25 L'oreal S.A. Conditioning and detergent composition comprising an anionic surfactant, a silicone, and a cationic polymer
US6495498B2 (en) 1999-05-27 2002-12-17 Johnson & Johnson Consumer Companies, Inc. Detergent compositions with enhanced depositing, conditioning and softness capabilities
US6858202B2 (en) 1999-05-27 2005-02-22 Johnson & Johnson Consumer Companies, Inc. Detergent compositions with enhanced depositing, conditioning and softness capabilities
US6908889B2 (en) 1999-05-27 2005-06-21 Johnson & Johnson Consumer Companies, Inc. Detergent composition with enhanced depositing, conditioning and softness capabilities
WO2017165112A1 (en) * 2016-03-22 2017-09-28 Kao Usa, Inc. Clear hair conditioner composition
US10624835B2 (en) 2016-03-22 2020-04-21 Kao Usa, Inc. Clear hair conditioner composition

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