WO2013034366A2 - Composition - Google Patents

Composition Download PDF

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Publication number
WO2013034366A2
WO2013034366A2 PCT/EP2012/064923 EP2012064923W WO2013034366A2 WO 2013034366 A2 WO2013034366 A2 WO 2013034366A2 EP 2012064923 W EP2012064923 W EP 2012064923W WO 2013034366 A2 WO2013034366 A2 WO 2013034366A2
Authority
WO
WIPO (PCT)
Prior art keywords
dimethicone
phase
composition
crosspolymers
modified cross
Prior art date
Application number
PCT/EP2012/064923
Other languages
French (fr)
Other versions
WO2013034366A3 (en
Inventor
Masatoshi Sakurai
Jiro Sano
Mitsuru Shimatani
Original Assignee
Unilever Plc
Unilever N.V.
Hindustan Unilever Limited
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 Unilever Plc, Unilever N.V., Hindustan Unilever Limited filed Critical Unilever Plc
Publication of WO2013034366A2 publication Critical patent/WO2013034366A2/en
Publication of WO2013034366A3 publication Critical patent/WO2013034366A3/en

Links

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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/03—Liquid compositions with two or more distinct layers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair

Definitions

  • EP 0 490 750 A1 discloses multi-phase liquid compositions comprising an oil phase and an aqueous phase which are immiscible, and solid particles which are insoluble in these two phases and stay at their interface resulting in a solids phase.
  • FR 2 208642 A1 The oil phase in some of the examples is liquid paraffin
  • FR 2 645740 A1 discloses a tri-phase composition based on an aqueous phase, an oil phase and a powder phase.
  • oil vaseline oil, silicone oil, including decamethylcyclopentasiloxane are considered. All of them are suitable for the hair.
  • JP 58177910 A discloses a three layered type liquid skin cosmetic.
  • the upper layer is an oily layer, for example liquid paraffin
  • the intermediate layer is aqueous
  • the bottom layer is powdery.
  • US 2007/060666 A 1 disclose personal care multi-phase compositions for hair treatment comprising a non aqueous oil phase and an aqueous phase which are immiscible and form patterns.
  • EP 2135596 A1 discloses a multi-phase hair composition comprising an oily phase and a water phase.
  • US 2006/078524 A 1 discloses a multi-phase personal care compositions for hair treatment based on a conditioning phase and a benefit phase. Despite the prior art there remains a need for improved multi-phase hair treatment compositions.
  • the present invention provides a multi-phase hair treatment composition according to claim 1 .
  • composition of the invention has at least three clearly identifiable phases and requires shaking prior to use in order to mix the contents sufficiently to provide the best possible consumer experience in hair treatment.
  • immiscible is meant that before agitation the three phases are visually distinct from one another when viewed through a transparent container.
  • the oil phase comprises from 5 to 60% by volume of the composition.
  • the oil phase of the invention preferably comprises a volatile silicone and an oil.
  • the oil is selected from mineral oils, vegetable oils and silicone oils.
  • the oil is a hydrocarbon oil.
  • the hydrocarbon is an alkane having from 4 to 30 carbon atoms.
  • the oil phase has a specific gravity of from 0.80 to 0.95.
  • the oil phase constitutes the uppermost of the phases when the compositions is left to settle and the phases substantially separate.
  • oils phase is visually clear. Solids Phase
  • the solids phase comprises a silicone in paste or elastomeric or spherical powder form and which comprises silicone in solid form at room temperature and pressure, i.e. at 20°C and 1 atm pressure dispersed in a suitable carrier such as silicone, ester or hydrocarbon oil.
  • a suitable carrier such as silicone, ester or hydrocarbon oil.
  • the solid silicone is a cross-linked silicone polymer.
  • the solids phase comprises from 0.01 to 30% by weight of the composition.
  • the silicone is selected from a polyglycerine-modified cross-linked polymer (e.g. KSG 710 ex. Shinetsu) or a polyether-modified cross-linked polymer (e.g. KSG 210, 240) or a polyether/alkyl co-modified cross-linked polymer (e.g. KSG 310, 320, 330, 340) or a polyglycerine/alkyl co-modified cross-linked polymer (e.g. KSG 810, 820, 830, 840) or Dimethicone/vinyl dimethicone crosspolymer (e.g.
  • a polyglycerine-modified cross-linked polymer e.g. KSG 710 ex. Shinetsu
  • a polyether-modified cross-linked polymer e.g. KSG 210, 240
  • a polyether/alkyl co-modified cross-linked polymer e.g. KSG 310, 320,
  • KSG-15, 16 Dimethicone/phenyl vinyl dimethicone crosspolymer (e.g. KSG-18A), Vinyl dimethicone/lauryl dimethicone crosspolymer (e.g. KSG-41 , 42, 43, 44) [Shinetsu chemical] or Dimethicone crosspolymer (e.g. DC 9040, 9041 , 9045 and 9546) [Dow Corning] or C30-45 alkyl cetearyl dimethicone crosspolymer (e.g. Velvesil 125, 034) or Cetearyl Dimethicone Crosspolymer (e.g. Velvesil DM) [Momentive] etc.
  • Dimethicone/phenyl vinyl dimethicone crosspolymer e.g. KSG-18A
  • Vinyl dimethicone/lauryl dimethicone crosspolymer e.g. KSG-41 , 42, 43, 44
  • the solid phase has a specific gravity of from 0.85 to 1 .00.
  • the solids phase constitutes a middle layer of the phases when the compositions is left to settle and the phases substantially separate and settles between the solids phase and the aqueous phase.
  • the solids phase presents a visual contrast to the oil phase and is opaque.
  • spherical powder may also be incorporated in the solids phase.
  • the spherical powder is selected from polyethylene, dimethicone closs- polymer (ex. EP-9215) [Dowcorning], hydrophobic silica, vinyl
  • dimethicone/methicone silsesquioxane crosspolymer e.g. KSP-100, 101 , 102, 105
  • crosspolymer e.g. KSP-300 [Shinetsu chemical] and Polymethylsilsesquioxane (e.g. Tospearl 120A, 145A, 2000B, 1 1 10B, 150KA, AQ, E-Pearl) [Momentive].
  • Such a preferred embodiment provides a multi-phase product which comprises solids phase for improved tactile performance but without leaving any white residue for the consumer. This is particularly beneficial for consumers with dark coloured hair.
  • the aqueous phase comprises from 10 to 95% by weight of the composition.
  • the aqueous phase comprises a water-soluble benefit agent.
  • Preferred water-soluble benefit agents include fibre actives such as dicarboxylic acids (such as adipic acid), saccharides (such as trehalose), lactones (such as
  • gluconolactone low molecular weight acids (such as lactic acid, citric acid, palmitic acid, succinic acid, etc.), amino acids such as arginine, lysine, glycine etc.
  • the aqueous phase may also incorporate any water soluble cosmetic ingredient if necessary.
  • the aqueous phase has a specific gravity of from 0.90 to 1 .05.
  • the aqueous phase comprises an emulsifier.
  • the emulsifier is capable of emulsifying the composition such that the phases of the composition can be easily mixed by the user sufficiently to be applied to the hair and to remain mixed until the product is no longer to be used.
  • Preferred emulsifiers include sorbeth esters, especially preferred are the sorbeth- 20 to 80. The most preferred emulsifier is sorbeth-60.
  • the aqueous phase comprises from 1 to 40% wt of the aqueous phase alcohol.
  • Preferred alcohols include ethanol.
  • the aqueous phase constitutes the lowermost layer of the phases when the compositions is left to settle.
  • the composition according to the invention is in a container which comprises a transparent or translucent part such that the three phases can be visually discerned prior to any agitation of the composition.
  • composition of the invention is able to deliver improved benefits to the consumer which are not achievable by compositions with the materials without any phase separation.
  • additional ingredients which is commonly used in cosmetics e.g. solvent, other oils, emulsifier, thickener, moisturizer, anti-dandruff agent, antioxidant, chelate agent, UV absorber, fragrance, colour
  • solvent e.g. solvent, other oils, emulsifier, thickener, moisturizer, anti-dandruff agent, antioxidant, chelate agent, UV absorber, fragrance, colour
  • composition according to the table is ordinarily immiscible if left to stand for more than 60 minutes and would settle such that the top phase is the oil phase, the middle phase is the solids phase and the bottom phase is the aqueous phase.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)

Abstract

A multi-phase hair treatment composition comprising: - an oil phase; - a solids phase comprising a silicone polymer which is a paste or elastomer and is a solid at room temperature and pressure, and - an aqueous phase, wherein each phase is immiscible from the other phases and wherein the polymer is selected from polyglycerine-modified cross-linked polymers, polyether- modified cross-linked polymers, polyether/alkyl co-modified cross-linked polymer, polyglycerine/alkyl co-modified cross-linked polymers, dimethicone/vinyl dimethicone crosspolymers, dimethicone/phenyl vinyl dimethicone crosspolymers, vinyl dimethicone/lauryl dimethicone crosspolymers, dimethicone crosspolymers, C30-45 alkyl cetearyl dimethicone crosspolymer and cetearyl dimethicone crosspolymers.

Description

COMPOSITION
The present invention relates to an improved hair treatment composition. EP 0 490 750 A1 discloses multi-phase liquid compositions comprising an oil phase and an aqueous phase which are immiscible, and solid particles which are insoluble in these two phases and stay at their interface resulting in a solids phase. FR 2 208642 A1 The oil phase in some of the examples is liquid paraffin
FR 2 645740 A1 discloses a tri-phase composition based on an aqueous phase, an oil phase and a powder phase. As oil, vaseline oil, silicone oil, including decamethylcyclopentasiloxane are considered. All of them are suitable for the hair.
JP 58177910 A discloses a three layered type liquid skin cosmetic. The upper layer is an oily layer, for example liquid paraffin, the intermediate layer is aqueous, the bottom layer is powdery.
US 2007/060666 A 1 disclose personal care multi-phase compositions for hair treatment comprising a non aqueous oil phase and an aqueous phase which are immiscible and form patterns. EP 2135596 A1 discloses a multi-phase hair composition comprising an oily phase and a water phase.
US 2006/078524 A 1 discloses a multi-phase personal care compositions for hair treatment based on a conditioning phase and a benefit phase. Despite the prior art there remains a need for improved multi-phase hair treatment compositions.
Accordingly, the present invention provides a multi-phase hair treatment composition according to claim 1 .
The composition of the invention has at least three clearly identifiable phases and requires shaking prior to use in order to mix the contents sufficiently to provide the best possible consumer experience in hair treatment.
By immiscible is meant that before agitation the three phases are visually distinct from one another when viewed through a transparent container.
Oil Phase
Preferably, the oil phase comprises from 5 to 60% by volume of the composition.
The oil phase of the invention preferably comprises a volatile silicone and an oil. Preferably, the oil is selected from mineral oils, vegetable oils and silicone oils. Preferably the oil is a hydrocarbon oil. Preferably, the hydrocarbon is an alkane having from 4 to 30 carbon atoms.
Preferably, the oil phase has a specific gravity of from 0.80 to 0.95. Preferably, the oil phase constitutes the uppermost of the phases when the compositions is left to settle and the phases substantially separate.
Preferably the oils phase is visually clear. Solids Phase
The solids phase comprises a silicone in paste or elastomeric or spherical powder form and which comprises silicone in solid form at room temperature and pressure, i.e. at 20°C and 1 atm pressure dispersed in a suitable carrier such as silicone, ester or hydrocarbon oil. Preferably, the solid silicone is a cross-linked silicone polymer.
Preferably, the solids phase comprises from 0.01 to 30% by weight of the composition.
The silicone is selected from a polyglycerine-modified cross-linked polymer (e.g. KSG 710 ex. Shinetsu) or a polyether-modified cross-linked polymer (e.g. KSG 210, 240) or a polyether/alkyl co-modified cross-linked polymer (e.g. KSG 310, 320, 330, 340) or a polyglycerine/alkyl co-modified cross-linked polymer (e.g. KSG 810, 820, 830, 840) or Dimethicone/vinyl dimethicone crosspolymer (e.g. KSG-15, 16), Dimethicone/phenyl vinyl dimethicone crosspolymer (e.g. KSG-18A), Vinyl dimethicone/lauryl dimethicone crosspolymer (e.g. KSG-41 , 42, 43, 44) [Shinetsu chemical] or Dimethicone crosspolymer (e.g. DC 9040, 9041 , 9045 and 9546) [Dow Corning] or C30-45 alkyl cetearyl dimethicone crosspolymer (e.g. Velvesil 125, 034) or Cetearyl Dimethicone Crosspolymer (e.g. Velvesil DM) [Momentive] etc.
Preferably, the solid phase has a specific gravity of from 0.85 to 1 .00.
Preferably, the solids phase constitutes a middle layer of the phases when the compositions is left to settle and the phases substantially separate and settles between the solids phase and the aqueous phase. Preferably, the solids phase presents a visual contrast to the oil phase and is opaque. To improve tactile benefit of the composition spherical powder may also be incorporated in the solids phase. Preferably the spherical powder is selected from polyethylene, dimethicone closs- polymer (ex. EP-9215) [Dowcorning], hydrophobic silica, vinyl
dimethicone/methicone silsesquioxane crosspolymer (e.g. KSP-100, 101 , 102, 105), Diphenyl dimethicone/vinyl diphenyl dimethicone/silsesquioxane
crosspolymer (e.g. KSP-300) [Shinetsu chemical] and Polymethylsilsesquioxane (e.g. Tospearl 120A, 145A, 2000B, 1 1 10B, 150KA, AQ, E-Pearl) [Momentive].
Such a preferred embodiment provides a multi-phase product which comprises solids phase for improved tactile performance but without leaving any white residue for the consumer. This is particularly beneficial for consumers with dark coloured hair.
Aqueous Phase
The aqueous phase comprises from 10 to 95% by weight of the composition.
Preferably, the aqueous phase comprises a water-soluble benefit agent. Preferred water-soluble benefit agents include fibre actives such as dicarboxylic acids (such as adipic acid), saccharides (such as trehalose), lactones (such as
gluconolactone), low molecular weight acids (such as lactic acid, citric acid, palmitic acid, succinic acid, etc.), amino acids such as arginine, lysine, glycine etc. The aqueous phase may also incorporate any water soluble cosmetic ingredient if necessary.
Preferably, the aqueous phase has a specific gravity of from 0.90 to 1 .05. Preferably, the aqueous phase comprises an emulsifier. Preferably, the emulsifier is capable of emulsifying the composition such that the phases of the composition can be easily mixed by the user sufficiently to be applied to the hair and to remain mixed until the product is no longer to be used.
Preferred emulsifiers include sorbeth esters, especially preferred are the sorbeth- 20 to 80. The most preferred emulsifier is sorbeth-60.
Preferably, the aqueous phase comprises from 1 to 40% wt of the aqueous phase alcohol. Preferred alcohols include ethanol.
Preferably, the aqueous phase constitutes the lowermost layer of the phases when the compositions is left to settle. Preferably, the composition according to the invention is in a container which comprises a transparent or translucent part such that the three phases can be visually discerned prior to any agitation of the composition.
The composition of the invention is able to deliver improved benefits to the consumer which are not achievable by compositions with the materials without any phase separation.
In this formula, additional ingredients which is commonly used in cosmetics (e.g. solvent, other oils, emulsifier, thickener, moisturizer, anti-dandruff agent, antioxidant, chelate agent, UV absorber, fragrance, colour) can be formulated for improve the performance.
The invention will now be described with reference to the following non-limiting example. The following composition is made by standard processes.
The composition according to the table is ordinarily immiscible if left to stand for more than 60 minutes and would settle such that the top phase is the oil phase, the middle phase is the solids phase and the bottom phase is the aqueous phase.
It is shaken by the consumer immediately prior to use and then applied to the hair in a pump-spray applicator.

Claims

A multi-phase hair treatment composition comprising: an oil phase
a solids phase comprising a silicone polymer which is a paste or elastomer and is a solid at room temperature and pressure, and an aqueous phase, wherein each phase is immiscible from the other phases and wherein the polymer is selected from polyglycerine-modified cross-linked polymers, polyether-modified cross-linked polymers, polyether/alkyl co-modified cross- linked polymer, polyglycerine/alkyl co-modified cross-linked polymers, dimethicone/vinyl dimethicone crosspolymers, dimethicone/phenyl vinyl dimethicone crosspolymers, vinyl dimethicone/lauryl dimethicone
crosspolymers, dimethicone crosspolymers, C30-45 alkyl cetearyl dimethicone crosspolymer and cetearyl dimethicone crosspolymers.
Composition according to claim 1 wherein the oil phase comprises a volatile silicone.
Composition according to claim 1 or 2 wherein the oil phase comprises an alkane having from 4 to 20 carbon atoms.
Composition according to any preceding claim wherein the solids phase additionally comprises spherical particles. Composition according to claim 4 wherein the spherical particles are selected from polyethylene dimethicone cross-polymers, hydrophobic silicas, vinyl dimethicone/methicone silsesquioxane crosspolymers, diphenyl dimethicone/vinyl diphenyl dimethicone/silsesquioxane crosspolymers and polymethylsilsesquioxanes.
Composition according to any preceding claim in a container which comprises a transparent or translucent part such that the three phases can be visually discerned prior to any agitation of the composition.
Composition according to any preceding claim wherein the oil phase comprises from 5 to 60% by weight of the composition, the solid phase from 0.01 to 30% wt. of the composition and the aqueous phase from 10 to 95% wt. of the composition.
PCT/EP2012/064923 2011-09-06 2012-07-31 Composition WO2013034366A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP11180274.0 2011-09-06
EP11180274 2011-09-06
EP11191466 2011-12-01
EP11191466.9 2011-12-01

Publications (2)

Publication Number Publication Date
WO2013034366A2 true WO2013034366A2 (en) 2013-03-14
WO2013034366A3 WO2013034366A3 (en) 2013-07-04

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/064923 WO2013034366A2 (en) 2011-09-06 2012-07-31 Composition

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Country Link
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019002579A1 (en) * 2017-06-30 2019-01-03 Capsum Three-phase composition
JP2020033313A (en) * 2018-08-31 2020-03-05 株式会社マンダム Skin cosmetic

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2208642A1 (en) 1972-12-05 1974-06-28 Shiseido Co Ltd Two-phase liquid cosmetic preparation - contg. oil water, a water- and oil-miscible organic liquid and finely divided insoluble solid particles
JPS58177910A (en) 1982-04-12 1983-10-18 Shiseido Co Ltd Three-layered type liquid skin cosmetic
FR2645740A1 (en) 1989-04-12 1990-10-19 Fabre Pierre Cosmetique Three-phase topical compositions which can be emulsified immediately before use and which are useful in cosmetology and/or dermatology
EP0490750A1 (en) 1990-12-12 1992-06-17 L'oreal Liquid two-phase cosmetic composition containing at least a dialkylphthalate, insoluble particulates and a density equilibrating agent
US20060078524A1 (en) 2004-10-08 2006-04-13 Sanjeev Midha Multi phase personal care composition comprising a conditioning phase and an oil continuous benefit phase
US20070060666A1 (en) 2005-09-09 2007-03-15 Toshiya Taniguchi Solid skin care composition comprising multiple layers
EP2135596A1 (en) 2007-04-17 2009-12-23 Kao Corporation Hair cosmetic compositiions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002060397A1 (en) * 2001-01-30 2002-08-08 Unilever Plc Dual-phased styling product that provides styling and conditioning benefits
US20070297996A1 (en) * 2006-06-22 2007-12-27 The Procter & Gamble Company Multi-phase composition comprising a sunscreen

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2208642A1 (en) 1972-12-05 1974-06-28 Shiseido Co Ltd Two-phase liquid cosmetic preparation - contg. oil water, a water- and oil-miscible organic liquid and finely divided insoluble solid particles
JPS58177910A (en) 1982-04-12 1983-10-18 Shiseido Co Ltd Three-layered type liquid skin cosmetic
FR2645740A1 (en) 1989-04-12 1990-10-19 Fabre Pierre Cosmetique Three-phase topical compositions which can be emulsified immediately before use and which are useful in cosmetology and/or dermatology
EP0490750A1 (en) 1990-12-12 1992-06-17 L'oreal Liquid two-phase cosmetic composition containing at least a dialkylphthalate, insoluble particulates and a density equilibrating agent
US20060078524A1 (en) 2004-10-08 2006-04-13 Sanjeev Midha Multi phase personal care composition comprising a conditioning phase and an oil continuous benefit phase
US20070060666A1 (en) 2005-09-09 2007-03-15 Toshiya Taniguchi Solid skin care composition comprising multiple layers
EP2135596A1 (en) 2007-04-17 2009-12-23 Kao Corporation Hair cosmetic compositiions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019002579A1 (en) * 2017-06-30 2019-01-03 Capsum Three-phase composition
FR3068238A1 (en) * 2017-06-30 2019-01-04 Capsum THREE-PHASE COMPOSITION
JP2020033313A (en) * 2018-08-31 2020-03-05 株式会社マンダム Skin cosmetic

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