WO2005000252A1 - Emulsion cosmetique stable avec polyamide - Google Patents

Emulsion cosmetique stable avec polyamide Download PDF

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Publication number
WO2005000252A1
WO2005000252A1 PCT/US2004/017934 US2004017934W WO2005000252A1 WO 2005000252 A1 WO2005000252 A1 WO 2005000252A1 US 2004017934 W US2004017934 W US 2004017934W WO 2005000252 A1 WO2005000252 A1 WO 2005000252A1
Authority
WO
WIPO (PCT)
Prior art keywords
emulsion
composition
aqueous phase
percent
polyamide
Prior art date
Application number
PCT/US2004/017934
Other languages
English (en)
Other versions
WO2005000252A9 (fr
Inventor
Tian X Wang
Carl C. Orr
Dexin Luo
Paul H. Marotta
Hernando Brieva
Shahan Nazar
Richard J. Castro
Original Assignee
Color Access, Inc.
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 Color Access, Inc. filed Critical Color Access, Inc.
Priority to EP04776319A priority Critical patent/EP1635775A4/fr
Priority to JP2006533576A priority patent/JP2007500749A/ja
Priority to AU2004251705A priority patent/AU2004251705C1/en
Priority to CA002528605A priority patent/CA2528605A1/fr
Publication of WO2005000252A1 publication Critical patent/WO2005000252A1/fr
Publication of WO2005000252A9 publication Critical patent/WO2005000252A9/fr

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • 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
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara

Definitions

  • the invention relates to a cosmetic and personal care gel product that is gelled using a polyamide as a gelling agent in the oil phase. More specifically, the invention relates to a stable emulsion based compositions comprising a polyamide gelling agent in the oil phase.
  • the polyamide resin has also been used in a deodorant or antiperspirant gel or stick as disclosed in U.S. Patent Nos. 4,275,054 and 5,500,209 because of its odor absorbing properties. None of these references, however, discloses an emulsion gelled with the non-siloxane based polyamide in combination with an ethylene oxide containing emulsion stabilizer.
  • U.S. Patent Nos. 6,051,216, 5,603,925, and 5,998,570 and European Patent Application Nos. EP 1 068 855 and EP 1 068 856 are unstable emulsions, single phase compositions, or use a siloxane based polyamide.
  • the siloxane polyamides have been developed because of their alleged ability to, in addition to gel the composition, provide a less tacky composition.
  • the siloxane based polyamides are not compatible with a wide variety of oils, for example, hydrocarbon oils, and because they are less tacky, their adhesion properties are significantly impaired, making them less desirable in products that require minimally an initial phase of adhesion during the application of the product to the skin or hair.
  • the emulsion system of the present invention is also desirable because it allows water-soluble ingredients to be incorporated into the product containing the emulsion.
  • the invention relates to gelled cosmetic compositions, and specifically, oil-in-water or water-in- oil emulsions, which comprises at least one sugar-based emulsion stabilizer and at least one non- siloxane based polyamide resin.
  • the prepared emulsions while they are not themselves clear, are substantially transparent after application to the skin.
  • Use of the polyamide resin as a gelling agent per se is not new, however, its incorporation into the color compositions of the present invention containing, for example, alkylglucosides with about 8 to 16 carbon atoms, as an emulsion stabilizer is surprising.
  • the cosmetic emulsions of the present invention also comprise a color component present in an amount greater than about 2.0 percent by weight of the composition.
  • the ability to gel a color cosmetic emulsion with the polyamide resin as the primary gelling agent is particularly challenging because the polyamide is very polar and emulsions containing large quantities of polyamide tend to be tacky and are difficult to stabilize in the presence of colorants.
  • the present invention also includes methods of making the emulsion systems of the present invention which can include multiple emulsion systems.
  • the emulsion products are especially transparent and transfer resistant when they are applied to the skin and allowed to dry.
  • the compositions containing these emulsions have an enhanced brightness and clarity with respect to their color on the skin after application thereon due to the transparent film that adheres to the skin without being tacky.
  • the emulsion systems of the present invention dry faster than other polyamide containing systems, and are long wearing even after the water evaporates.
  • gels and sticks made with the emulsion system of the present invention are less brittle, experience a substantial lack of syneresis, and have a creamier texture because the three-dimensional structure formed by the polyamide resin is interrupted partially by the water phase.
  • the gelling system of the present invention is at least one non-siloxane based polyamide resin and at least one sugar-based emulsion stabilizer.
  • the polyamide resin as used herein is defined to be a polymer having recurring units of amide groups as an integral part of the main chain of the polymer and a terminal end group of acid, amine, or ester.
  • the polyamide gelling agent can be used to produce a soft gel or a stick composition in an emulsified system. Therefore, it is preferable that the polyamide resin not be extensively cross-linked by hydrogen bonds.
  • the polyamides are characterized as thermoplastics as opposed to thermosets.
  • the polyamides used in the present invention are water insoluble.
  • the polyamide is available in a solid form of 100 percent polyamide or as a percentage of polyamide in mineral oil, usually about 80 percent.
  • Examples of commercially available polyamides which are useful in the present invention are Versamid 1655, by Cognis (formerly Henkel Corporation), Ambler, PA which is prepared from dimers of Ci 8 unsaturated fatty acids which are partially hydrogenated, azelaic acid (nonanedioic acid), ethylene diamine, hexamethylene diamine and stearic acid, Unirez and Uniclear, a series of polyamides from Arizona Chemicals Corporation, Jacksonville, FL or Elvamide from DuPont, DE a te ⁇ olymer of nylon 6, nylon 66, and nylon 610.
  • compositions comprise a nonaqueous liquid as solvent, preferably a low-polarity liquid.
  • the water phase of the cosmetic emulsion of the present invention comprises about 0.05 to 90.0 percent, and preferably 1.0 to 70.0 percent by weight of the emulsions. While the water phase is primarily water, it can take the form of a variety of aqueous solutions such as rose water, tea, and the like. Therefore, the water phase is well suited to deliver water-soluble actives and other water dispersible agents, such as for example, film-formers, surfactants, and emollients.
  • the non-aqueous phase can include any type of cosmetically acceptable volatile or non-volatile oil including oily esters depending on the application of the product and the degree of gelling desired.
  • oils such as isododecane
  • silicone oils such as cyclomethicone
  • polyorganosiloxanes such as phenyl-methicones and dimethicones
  • castor oil and hydrogenated vegetable oil.
  • the oil is volatile, such as for example, a volatile hydrocarbon oil or silicone oil; while a lipstick is a mixture of both volatile and non- olatile oils and the amounts of each depends on the type of lipstick desired.
  • Suitable non-volatile hydrocarbons include, but are not limited, to isoparaffins, squalane, or petrolatum, or mixtures thereof. Regardless of the amount of volatile and/or non-volatile oil, the entire oil phase is present in an amount of about 5 to about 95 percent, preferably 10 to 80 percent by weight of the composition, and more preferably about 10 to 40 percent.
  • the emulsions of the present invention are prepared by adding a gelling sufficient amount of the polyamide resin to the oil phase.
  • the amount of polyamide resin used in the present invention is from about 1 to about 90 percent, preferably about 2 to 40 percent by weight of the composition.
  • the amount of polyamide is a "gelling sufficient amount" and as used herein means an amount of polyamide in the oil phase to bring about an increase in the viscosity of the emulsion; preferably the viscosity increases by 25 percent, more preferably by 50 percent, and most preferably by 75 percent. This increase in viscosity is sufficient to form a thickened gel or form a solid having the hardness of a stick as the thickness of gels and sticks are known in the art. At lower levels, the polyamide aids in forming a gel, whereas, higher levels are used to make stick products.
  • a gel is, in general, more viscous than a liquid; but, it is not as rigid or self-supporting as a stick. It is accepted by one of ordinary skill in the art that a gel maintains a certain degree of deformity, whereas, the stick is free-standing and is substantially rigid.
  • Another component of the present invention is the emulsion stabilizer having a silicone backbone, containing a sugar based moiety, and being free of alkylene oxide units.
  • sugar-based emulsion stabilizer refers to stabilizers that are based on saccharide and/or glyceryl moieties that have a silicone backbone and are free of alkylene oxide units.
  • the sugar-based emulsion stabilizer can be non-ionic, cationic, anionic, or amphoteric.
  • the nonionic sugar-based emulsion stabilizers that may be included in the present invention are selected from the group consisting of alkyl polyglycosides, alkyl glucose esters, aldobionamides, gluconamides, glyceramides, glyceroglycolipids, polyhydroxy fatty acid amides (glucamides), and mixtures thereof.
  • the Glucopon® and Plantaren® series of products from Henkel Corporation are useful emulsion stabilizers in the present invention.
  • Cationic sugar-based emulsion stabilizers are, for example, a cationic sugar surfactant containing at least one hydrocarbon group with 6-24 carbon atoms and at least one quaternary ammonium group where at least one substituent is an alkyleneoxy containing group which is connected to a saccharide residue by a glycosidic bond, as those disclosed in U.S. Patent Nos. 6,503,880, 6,432,907, and 5,773,595.
  • Anionic and amphoteric surfactants are, for example, acylsucrose derivatives such as those disclosed in U.S. 6,184,196.
  • the emulsion stabilizer is one that has a certain ratio of sugar moiety to siloxane units (e.g., about 0.5 to 10 percent). It is su ⁇ risingly discovered with the present invention that a stable emulsion comprising the polyamide resin as the gelling agent can be achieved.
  • a stable emulsion comprising the polyamide resin as the gelling agent can be achieved.
  • gel oil based systems with the polyamide resin until now, these systems have primarily been single phase, i particular, stable dual phase compositions, and especially, stable cosmetic emulsions, have not been known to contain a non-siloxane based polyamide gelling agent as they experience stability problems.
  • the non-siloxane based polyamides are known to be tacky.
  • the method of preparing the emulsions of the present invention entails basic steps known in the art for preparing emulsions.
  • the non-siloxane based polyamide and the other ingredients in the oil phase may be prepared separately but are combined or added to the oil phase before combining with the aqueous phase to make the emulsion.
  • the present emulsions, containing the gelling system can be prepared with the polyamide as the primary gelling agent in the gelling system or with other naturally derived or synthetic gellants or thickening agents, known and commonly used by one skilled in the art, such as for example, cetyl dimethicone copolyol, acrylates copolymer, dextrin fatty acid esters, carbopols, dibenzyl monosorbitol acetal, polyethylene wax, beeswax, carnauba wax, candilla wax, bayberry wax, rice wax, acylglutamic acid diamide, esters, fatty alcohols, and the like can be used in the oil phase of the present invention.
  • other naturally derived or synthetic gellants or thickening agents known and commonly used by one skilled in the art, such as for example, cetyl dimethicone copolyol, acrylates copolymer, dextrin fatty acid esters, carbopols, dibenzyl monosorbito
  • the compositions of the present invention are wax-free.
  • a sugar-based surfactant stabilizes the emulsion system containing the polyamide as the gelling agent.
  • the difficulty of formulating a cosmetic emulsion and in addition, the difficulty of inco ⁇ orating the non-siloxane polyamide gelling agent in the emulsion, it is su ⁇ rising that greater stability is achieved using the sugar-based emulsifier.
  • stability and enhanced gelling is achieved with the sugar-based emulsifier because it is capable of hydrogen bonding with the polyamide gelling agent.
  • the emulsion stabilizer can be a single surfactant or a combination of surfactants.
  • the emulsion stabilizers aid in rendering the polyamide resin compatible in the dual phase system, and enhance not only the stability of the emulsion containing the non-siloxane based polyamide resin as the gelling agent, but may also affect the gelling activity of the polyamide resin.
  • the polyamide resin is water-insoluble when used as a gelling agent in the emulsion, with commonly used cosmetic oils stability problems are known to arise. In particular, agglomeration occurs or the phases separate in a short time, for example, in about few hours to about a few months.
  • the present invention has discovered that this problem can be remedied with the emulsion stabilizer which can be present in the oil phase, the water phase, or both.
  • the polyamide resin is rendered compatible in the emulsion stabilizer at room temperature and/or at elevated temperature, hi addition, the emulsion is stable for about 6 months, preferably about 1 year,
  • the active ingredients inco ⁇ orated in the emulsions of the present invention having a polyamide as the gelling agent preferably do not include antiperspirant actives especially those that are acidic metal salts.
  • actives examples include, but are not limited to, sunscreen actives, whitening agents, such as for example, antioxidants, antimicrobials, analgesics, anesthetics, anti-acne agents, antidermatitis agents, antipruritic agents, anti-inflammatory agents, antihyperkeratolytic agents, anti-dry skin agents, antipsoriatic agents, antiseborrheic agents, antiaging agents, antiwrinkle agents, self-tanning agents, wound-healing agents, corticosteroids, or hormones.
  • sunscreen actives such as for example, antioxidants, antimicrobials, analgesics, anesthetics, anti-acne agents, antidermatitis agents, antipruritic agents, anti-inflammatory agents, antihyperkeratolytic agents, anti-dry skin agents, antipsoriatic agents, antiseborrheic agents, antiaging agents, antiwrinkle agents, self-tanning agents, wound-healing agents, corticosteroids, or hormones.
  • ultraviolet screen refers to any material which is capable of protecting skin from ultraviolet radiation having a wavelength of from about 280 to about 400 nm, by effectively absorbing such radiation, and/or reflecting or scattering such radiation away from the surface of skin.
  • sunscreens with which the compositions of the present invention can be combined in this context are titanium dioxide, zinc oxide, benzophenones, octyl dimethyl PABA, amyldimethyl PABA, octyl methoxycinnaniate, 2-ethoxy p-methoxycinnamate, oxybenzone, homosalate, phenyl salicylate, avobenzene, glyceryl p-arninobenzoate, ethyl-p-glycosylimido benzoate and the like, hi a formulation, the sunscreen agent is used in the amounts normally used for that agent.
  • the active is non- acidic.
  • the cosmetic product can be, but is not limited to, a lipstick, lip gloss or other lip product, a solid, or gel fragrance or perfume product, cleanser, toner, an eye product, such as a mascara, eyeliner or an eye gel, compact emulsion foundation, concealer, moisturizing skin lotion or cream, hair stick or gel, and any other makeup, or skin or sun care product that is in a gel or stick form.
  • the product is a mascara or lipstick product.
  • the base of the lipstick or mascara has sufficient clarity such that the color is bright and luminous, i.e., they are transparent, semi-transparent, or translucent.
  • the products of the present invention are long wearing, non-smudging, and non-flaking.
  • the clear cosmetic product can contain other optional components as long as they do not interfere with the gelling properties of the polyamide.
  • examples include, but are not limited to, one or more preservatives such as, for example, propyl paraben, butyl paraben, mixtures thereof, or isoforms thereof, as well as butyl hydroxy toluene or butyl hydroxy anisol (BHT or BHA); fragrances (such as pinene); flavoring agents; wate ⁇ roofing agents (such as PVP/eicosene copolymer); surfactants, such as silicone copolyols or fatty acid glycerol esters; and oil-soluble actives, such as tocopherol and its derivatives or retinol and its derivatives; and the like.
  • preservatives such as, for example, propyl paraben, butyl paraben, mixtures thereof, or
  • the lipstick is prepared by combining Phase I ingredients together and heating them to about 99°C for about 2 hours. Phase II ingredients are combined and ground in a homogenizer at about 3000 ⁇ m for about 10 minutes. The homogenized Phase II ingredients are added to Phase I and together the combination is heated to 80°C. Phase HI is added to the combined Phase I and Phase II ingredients at a temperature of about 80°C by mixing. Adjust pH of combination with to about 7.35.
  • the lipstick can be made by pouring the combination into a lipstick mold or by following any known technique for making a lipstick.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical 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)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une émulsion cosmétique gélifiée comprenant une phase huileuse, une phase aqueuse et un système gélifiant qui contient au moins un polyamide à base non siloxane en quantité suffisante pour gélifier l'émulsion. Ce polyamide peut comporter un groupe terminal amine, amide tertiaire, acide ou ester. L'émulsion est stabilisée au moyen d'un agent de stabilisation d'émulsion à base de sucre. Les émulsions de la présente invention sont sensiblement transparentes et, lorsque des colorants sont ajoutés, la couleur est spécialement brillante et claire. Ces émulsions sont utilisées dans des produits de type rouges à lèvre et mascaras ainsi que dans d'autres produits en bâton et gélifiés.
PCT/US2004/017934 2003-06-09 2004-06-07 Emulsion cosmetique stable avec polyamide WO2005000252A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP04776319A EP1635775A4 (fr) 2003-06-09 2004-06-07 Emulsion cosmetique stable avec polyamide
JP2006533576A JP2007500749A (ja) 2003-06-09 2004-06-07 ポリアミドを含む安定な化粧用エマルション
AU2004251705A AU2004251705C1 (en) 2003-06-09 2004-06-07 Stable cosmetic emulsion with polyamide
CA002528605A CA2528605A1 (fr) 2003-06-09 2004-06-07 Emulsion cosmetique stable contenant une resine de polyamide sans siloxane

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47715303P 2003-06-09 2003-06-09
US60/477,153 2003-06-09

Publications (2)

Publication Number Publication Date
WO2005000252A1 true WO2005000252A1 (fr) 2005-01-06
WO2005000252A9 WO2005000252A9 (fr) 2006-02-16

Family

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Family Applications (1)

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PCT/US2004/017934 WO2005000252A1 (fr) 2003-06-09 2004-06-07 Emulsion cosmetique stable avec polyamide

Country Status (5)

Country Link
EP (1) EP1635775A4 (fr)
JP (1) JP2007500749A (fr)
AU (1) AU2004251705C1 (fr)
CA (1) CA2528605A1 (fr)
WO (1) WO2005000252A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2886847A1 (fr) * 2005-06-10 2006-12-15 Oreal Gel fragmente, dispersion et composition contenant un tel gel, procedes de preparation et utilisations
FR2948020A1 (fr) * 2009-07-20 2011-01-21 Oreal Composition de soin et/ou de maquillage de la peau contenant une dispersion d'oxychlorure de bismuth
WO2011010041A3 (fr) * 2009-07-20 2011-04-07 L'oreal Emulsion contenant une dispersion d'oxychlorure de bismuth
FR2960774A1 (fr) * 2010-06-02 2011-12-09 Oreal Composition cosmetique destinee a conferer effet de lumiere et eclat sur les matieres keratiniques
US8221199B2 (en) 2007-01-11 2012-07-17 Smith Abrasives, Inc Abrasive sharpener

Families Citing this family (3)

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Publication number Priority date Publication date Assignee Title
US8317423B2 (en) * 2004-08-11 2012-11-27 Elc Management Llc Mascara for use with a vibrating applicator: compositions and methods
FR2914856B1 (fr) * 2007-04-12 2012-08-03 Arkema France Composition cosmetique comprenant une poudre fine
KR102372698B1 (ko) * 2016-03-21 2022-03-08 로레알 수용성 염료를 포함하는 화장용 조성물

Citations (2)

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Publication number Priority date Publication date Assignee Title
DE4217673A1 (de) * 1992-05-29 1993-12-02 Huels Chemische Werke Ag Elektrolytverdickbare Tensidkombinationen
US6497861B1 (en) * 2001-06-21 2002-12-24 Color Access, Inc. Stable cosmetic emulsion with polyamide gelling agent

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US5047167A (en) * 1987-12-30 1991-09-10 Lever Brothers Company, Division Of Conopco, Inc. Clear viscoelastic detergent gel compositions containing alkyl polyglycosides
US6268466B1 (en) * 1999-01-04 2001-07-31 Arizona Chemical Company Tertiary amide terminated polyamides and uses thereof
ES2300451T3 (es) * 2001-06-21 2008-06-16 Color Access, Inc. Emulsion cosmetica estable con agente gelificante poliamidico.

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
DE4217673A1 (de) * 1992-05-29 1993-12-02 Huels Chemische Werke Ag Elektrolytverdickbare Tensidkombinationen
US6497861B1 (en) * 2001-06-21 2002-12-24 Color Access, Inc. Stable cosmetic emulsion with polyamide gelling agent

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 199349, Derwent World Patents Index; AN 1993:387485, XP002903595, "Surfactant compsn. for bath gel, shampoo and cosmetic cleanser - thickenable with electrolyte, contg. alkyl:poly:glycoside, carboxylated alkanol ethoxylate, mono-alkyl sulpho:succinate and surfactant additive" *
See also references of EP1635775A4 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2886847A1 (fr) * 2005-06-10 2006-12-15 Oreal Gel fragmente, dispersion et composition contenant un tel gel, procedes de preparation et utilisations
US8221199B2 (en) 2007-01-11 2012-07-17 Smith Abrasives, Inc Abrasive sharpener
FR2948020A1 (fr) * 2009-07-20 2011-01-21 Oreal Composition de soin et/ou de maquillage de la peau contenant une dispersion d'oxychlorure de bismuth
WO2011010041A3 (fr) * 2009-07-20 2011-04-07 L'oreal Emulsion contenant une dispersion d'oxychlorure de bismuth
EP2826459A1 (fr) * 2009-07-20 2015-01-21 L'oreal Emulsion contenant une dispersion d'oxychlorure de bismuth
EP2826460A1 (fr) * 2009-07-20 2015-01-21 L'oreal Emulsion contenant une dispersion d'oxychlorure de bismuth
US9452114B2 (en) 2009-07-20 2016-09-27 L'oreal Emulsion containing a dispersion of bismuth oxychloride
US9956147B2 (en) 2009-07-20 2018-05-01 L'oreal Emulsion containing a dispersion of bismuth oxychloride
FR2960774A1 (fr) * 2010-06-02 2011-12-09 Oreal Composition cosmetique destinee a conferer effet de lumiere et eclat sur les matieres keratiniques

Also Published As

Publication number Publication date
AU2004251705B2 (en) 2007-02-22
JP2007500749A (ja) 2007-01-18
AU2004251705A1 (en) 2005-01-06
WO2005000252A9 (fr) 2006-02-16
EP1635775A4 (fr) 2009-04-29
EP1635775A1 (fr) 2006-03-22
CA2528605A1 (fr) 2005-01-06
AU2004251705C1 (en) 2007-02-22

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