WO1995017884A1 - Composition cosmetique solide lipophile comprenant un colorant acide - Google Patents

Composition cosmetique solide lipophile comprenant un colorant acide Download PDF

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Publication number
WO1995017884A1
WO1995017884A1 PCT/US1994/014288 US9414288W WO9517884A1 WO 1995017884 A1 WO1995017884 A1 WO 1995017884A1 US 9414288 W US9414288 W US 9414288W WO 9517884 A1 WO9517884 A1 WO 9517884A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
cosmetic composition
dye
lipophilic
solid cosmetic
Prior art date
Application number
PCT/US1994/014288
Other languages
English (en)
Inventor
Yoshinori Endo
Toshimichi Yamamoto
Toshiya Taniguchi
Original Assignee
The Procter & Gamble Company
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 Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AU14006/95A priority Critical patent/AU699995B2/en
Priority to EP95905358A priority patent/EP0742710A1/fr
Publication of WO1995017884A1 publication Critical patent/WO1995017884A1/fr

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
    • A61K8/18—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
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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

Definitions

  • the present invention relates to a lipophilic solid cosmetic composition having good stainability, long-lasting effect, and good color stability, for example, cosmetic compositions suitable for lipsticks, eye shadows, blushers, and foundations.
  • Coloring agents such as pigments and dyes are used in lipophilic solid cosmetic compositions mainly used for the purpose of make-up; for example, lipsticks, eye shadows, blushers, and foundations; in order to provide color to the skin.
  • the coloring agents used here should not only provide an alluring color, but also meet general characteristics required for making a cosmetic composition. Namely, such characteristics are; homogeneity in appearance, good stainability upon application, and long-lasting effect with stable color after application.
  • GB Patent 1,173,743 discloses that it is useful to contain a oil-insoluble dye or a combination of oil-insoluble dye and oil-soluble dye in a cosmetic.
  • JP Laid-open patent S63-11940S discloses a transparent solid cosmetic having good transparency, stability in appearance, and superior usage and dye solubility characterized in comprising 12-hydroxystearic acid, polyhydric alcohol ester of rosin, and a partial ester of polyhydric alcohol and branched fatty acid, or ester of polyhydric alcohol and unsaturated fatty acid.
  • JP Laid-open patent Hl-90110 discloses a transparent solid cosmetic having good transparency, stability in appearance, and superior usage and dye solubility characterized in comprising polyamide resin, pentaerythritot rosin ester, and a partial ester of polyglycerin and branched fatty acid, or an ester of polyglycerin and unsaturated fatty acid.
  • JP Laid-open patent Hl-287011 discloses an emulsified lipstick having a brilliant color comprising water-soluble mineral clay, water, and fluorescent-type dye.
  • JP Laid-open patent H3-86808 discloses a lipstick having superior utility characteristic such as good coming out of color, spreadability, attachment, long-lasting effect, and good appearance as well as stability, comprising 13-21% solid hydrocarbon, 15-60% ester compound made of oxy acid and fatty alcohol, 20-65% liquid or paste-type hydrocarbon, and oil-base dye.
  • JP Laid-open patent H3-90013 discloses a lipstick having superior utility characteristic such as good coming out of color, spreadability, attachment, long-lasting effect, and good appearance as s well as stability, comprising 13-21% solid hydrocarbon, 15-60% ester compound made of polyhydric alcohol and fatty alcohol, 20-65% liquid or paste-type hydrocarbon, and oil-base dye.
  • JP Laid-open patent H3-236307 discloses a lipophilic cosmetic which does not sweat, and has a high chroma color characterized in comprising 0.01-30 wt% of a gamma-alumina having a certain relative surface area, and 0.01-10 wt% oil-base dye.
  • acidic dyes tend to decolor as it is exposed to humidity in the atmosphere, which causes changing of coloring itself. It is not preferable for a make-up cosmetic such as lipstick to decolor.
  • lipophilic cosmetics including acidic dye such as lipsticks tended to be used for dark shades, for decoloring of such shades would not be so obvious.
  • a lipophilic solid cosmetic s composition having good stainability, long-lasting effect, and good color stability, namely, less decoloring over time, was obtained.
  • Dyes are also generally known to be difficult to homogeneously include in lipophilic solid cosmetic compositions because of its tendency to separate from the other 0 lipophilic components, and thus, are desired to be included at its minimum.
  • a lipophilic solid cosmetic composition having good stainability, long-lasting effect, and good color stability, and further with improved homogeneity of appearance was obtained over a wide range of shades with a small total amount of dye.
  • the present invention relates to a lipophilic solid cosmetic composition
  • a lipophilic solid cosmetic composition comprising by weight:
  • the cosmetic composition of the present invention comprises 0.01-1 wt%, preferably 0.01-0.25 wt% of an acidic dye.
  • the acidic dyes used in the present invention are those which are safe enough to be used in cosmetics, such as D&C Red #28 (Red #104-(1) according to Japanese Ministry of Health and Welfare Regulations; hereinafter "MHW"), D&C Red #6 (Red #201 s according to MHW Regulations), FD&C Yellow #5 (Yellow #4 according to MHW Regulations), and FD&C Yellow #6 (Yellow #5 according to MHW Regulations).
  • Acidic dyes can be included in the cosmetic composition as-is, or as a mixture with fatty acid ester.
  • the cosmetic composition of the present invention comprises 0.01-0.5 wt%, preferably 0.05-0.1 wt% of a water-soluble organic acid having one or more functional groups.
  • water- o soluble organic acids are citric acid, anhydrous citric acid, lactic acid, tartaric acid, and malic acid.
  • acidic dyes are generally known to decolor, the stainability and stability of color over time are improved by combining them with organic acid. Such effects can be seen with a small amount of organic acid, but can be significantly seen when the organic acid is included at a level s of at least 0.5 times weight of the acidic dye.
  • the cosmetic composition of the present invention can further comprise 0.01-2 wt%, preferably 0.01-0.5 wt% of an oil-base dye.
  • the oil-base dyes used in the present invention are those which are safe enough to be used in cosmetics, such as D&C Red #21 (Red #223 according to MHW Regulations), D&C Red #27 (Red #218 according to MHW Regulations), and D&C Orange #5 0 (Orange #201 according to MHW Regulations).
  • an oil- base dye by including an oil- base dye, the same level of stainability can be obtained by using less amount of dye in total as compared to ' that when only acidic dye is included. It is desirable that due is included at the minimum level in view of safety to the skin and product stability. Further, with the combination of dyes, the variety of shades are widened.
  • acidic dyes oil-base dyes can be 5 included in the cosmetic composition as-is, or as a mixture with fatty acid ester. Solvent
  • organic acid can be incorporated to the cosmetic composition by dissolving it into 0.1-5 wt%, preferably 0.5-3 wt%, most preferably 0.7-1.5 wt% to cosmetic composition of a solvent
  • Solvents are selected from the group consisting of water, monohydric 0 alcohol having 1 to 6 carbons, and polyhydric alcohol. Examples of solvents are water, ethanol, isopropanol, glycerin, diglycerin, triglycerin, ethylene glycol diethylene glycol, propylene glycol, dipropylene glycol, 1,3 butylene glycol, and 1,4 butylene glycol.
  • the orgamc acid can be dispersed homogeneously in the cosmetic composition, and thus it is preferable from a process point of view. It is also found that some 5 combinations of dye and solvent improve stability of color. Further, as some polyhydric alcohols have good attachment to the skin, the combination of these with dye improve the stainability.
  • the type of solvent is selected in consideration with solubility with other components in the cosmetic composition, and also with the needs of the desired product.
  • the lipophilic solid cosmetic compositions of the present invention can further comprise the following components as usually included in cosmetic compositions, in addition to those already disclosed herein.
  • the cosmetic compositions of the present invention contain 30-98 wt%, for lipsticks 60-98 wt%, preferably 80-95 wt% lipophilic material, and 0-65 wt%, for lipsticks 0-39wt%, preferably 2-20 wt% pigment.
  • Lipophilic Material for lipsticks 60-98 wt%, preferably 80-95 wt% lipophilic material, and 0-65 wt%, for lipsticks 0-39wt%, preferably 2-20 wt% pigment.
  • the lipophilic material used in the present invention can be selected from the group consisting from solid lipophilic material, liquid oil, oil gelling agent, and mixtures thereof. These components are selected by the one skilled in the art according to the desired cosmetic composition to be made. Preferably, for cosmetic compositions containing more than about 10% pigment such as foundations, eye shadows, and blushers, the mixture of solid lipophilic material, liquid oil, and oil gelling agent is included.
  • the solid lipophilic material act as a solidifying agent in the cosmetic composition. It can assist in the formation of the solid structure of the composition.
  • the solid is a low-melting organic compound or mixture of high molecular weight substances, and is solid or paste at room temperature.
  • the solids can be waxes, hydrocarbons, fatty acids, fatty alcohols, natural fats, or esters, but not limited thereof.
  • Natural, mineral and synthetic waxes can be used herein.
  • natural waxes of animal origin are beeswax, spermaceti, lanolin, shellac wax, or of vegetable origin, such as camauba, candelilla, bay berry, sugarcane wax, and of mineral origin, such as ozokerite, ceresin, montan, paraffin, macrocrystalline, vaseline, petroleum and petrolatum wax.
  • synthetic waxes are polyol ether-esters such as carbowax and hydrocarbon- type waxes, silicone waxes and polyethylene wax. Synthetic triglycerides in wax form such as esters of linear fatty acids are also useful. The most preferred waxes are ozokerite, ceresin, lanolin, microciystalline, camauba, beeswax, and paraffin waxes.
  • the fatty acids used herein can be saturated, unsaturated, linear, or branched.
  • Non-limiting examples are lauric, myristic, palmitic, stearic and behenic acids.
  • Non-limiting examples of fatty alcohols used herein are octyl, decyl, lauryl, myristyl, cetyl, stearyl, and behenyl alcohols.
  • Non-limiting examples of the natural fats useful herein are cocoa butter, palm oil, Japan wax, hydrogenated vegetable oil, hydrogenated castor oil, and cholesterol.
  • esters useful herein are myristyl myristrate, myristyl palmitate, myristyl stearate, cetyl palmitate, cetyl stearate, cetyl lactate, steaiyl lactate, cholesterol stearate, cholesterol oleate, cholesterol palmitate, cholesterol laurate, cholesterol myristate, cholesterol lineolate, and cholesterol ricinoleate.
  • Liquid Oils are myristyl myristrate, myristyl palmitate, myristyl stearate, cetyl palmitate, cetyl stearate, cetyl lactate, steaiyl lactate, cholesterol stearate, cholesterol oleate, cholesterol palmitate, cholesterol laurate, cholesterol myristate, cholesterol lineolate, and cholesterol ricinoleate.
  • liquid oils act as emollients, and imparts tackiness, and drag properties to the cosmetic.
  • Liquid oils are material that freely flow at room temperature. Liquid oils can also be volatile. Said liquid oils can be hydrocarbon oils, natural oils, fatty alcohols, fatty acid esters, and silicone oils, but not limited thereof.
  • Non-limiting examples of the hydrocarbons useful in the present invention are liquid paraffin, squalane, liquid petrolatum, mineral oil, and liquid polybutenes.
  • the natural oils used herein typically are mixtures of saturated and unsaturated fatty acids.
  • Non- limiting examples of natural oils derived from plants include almond oil, olive oil, sesame oil, sa Qower oil, avocado oil, cottonseed oil, jojoba oil, castor bean oil, castor oil, rapeseed oil, soybean oil, palm kernel oil, and coconut oil.
  • Non-limiting examples of natural oils derived from animal sources are mink oil and egg yolk oil.
  • Non-limiting examples of fatty alcohols useful in the present invention are isostearyl alcohol, lanolin alcohol, oleyl alcohol, hexadecyl alcohol, octyldodecanol alcohol, linoleyl alcohol, linolenyl alcohol, and arachidyl alcohol.
  • Fatty acids useful in the present invention can be natural or synthetic, saturated, unsaturated, linear, or branched.
  • Non-limiting examples of fatty acids useful in the present invention are adipic, caprylic, capric, isostearic, linoleic, ricinoleic, oleic, elaidic and erucic acids.
  • Non-limiting examples of the fatty acid esters useful in the present invention are cetyl ricinoleate, cetyl oleate, cetyl octanoate, cetyl acetate, glyc ⁇ ryl trioctanoate, isopropyl lanolate, isopropyl linoleate, isopropyl myristate, isopropyl palmitate, isopropyl oleate, isopropyl stearate, ethyl lactate, ethyl glutamate, ethyl laurate, ethyl linoleate, ethyl methacrylate, ethyl myristate, ethyl palmitate, diisopropyl adipate, octyl dodecyl myristate, octyl palmitate, octyl isopelargonate, octyl dodecyl lactate
  • Non-volatile and volatile, straight, branched, and cyclic silicone oils such as dimethicone, phenyl dimethicones, and cyclomethicones are also useful.
  • Oil Gelling Agents such as dimethicone, phenyl dimethicones, and cyclomethicones are also useful.
  • oil gelling agents are included for gelatinizing or viscosity controlling of the formulation.
  • oil gelling agents useful in the present invention are condensation products of benzaldehydes and polyhydric alcohols having at least 5 bases such as dibenzylidene xylitol, paratribenzylidene sorbitol, metal soaps such as calcium stearate, calcium palmitate, lithium salt of 2 -ethyl hexane, alminium salt of l,2,hydroxystearate, amide, ester, and amide derivatives of N-acylamino acids such as lauroyl glutamate dibutylamide, lauroyl glutamate stearamide, dicaproyl lysine lauroylamide, dicaproyl lysine lauroylamine salt, dicaproyl lysine lauiyl ester, dicaproyl lysine lauroyl phenylalanine laurylamide; dextrine fatty acid
  • Non-limiting examples of pigments useful in the present invention are talc, mica, clay, kaolin, zinc oxide, nylon powder, ultramarine, pearl pigments (bismuth oxychloride, guanine), iron oxide, titanium oxide, titanated mica, calcium carbonate, tar pigments, and other organic pigments.
  • Pigments which are surface treated with silicones and its derivatives, metal soaps, fluorine compounds and its derivatives, lecithin and its derivatives, amino acids and its salts, etc. can also be used.
  • the pigments can also be dispersed in an oily medium such as those disclosed above under liquid oils prior to use in the making process. Pigments can be purchased pre-dispersed in an oily medium like castor oil, or as dry powders which subsequently are dispersed in a chosen medium by the formulator.
  • compositions made by the process of the present invention can optionally contain components in addition to those already disclosed herein, so long as the lipophilic solid cosmetic composition as a whole has a common pH in the range of 4-7.
  • Optional components include antioxidants, preservatives, antiinflammatoiy agents, astringents, pH buffers, perfumes, ultraviolet and infrared screening agents, nonionic surfactants such as fatty acid esters and polyoxyalkylene fatty acid esters, amphoteric and anionic surfactants such as lecithins and phosphates, vitamins, and skin conditioning agents.
  • Antioxidants and preservatives can be, and usually will be formulated in the composition of the present invention to make products attractive to the consumer.
  • Useful antioxidants and preservatives are tocopherol, dibutylhydroxy toluene, methylparaben, and propylparaben. These components are typically present at levels not more than 1 % respectively.
  • Useful skin conditioning agents are beta-glycyrrhetic acid and its derivatives, vegetation extracts, allantoin, collagen, and extract and treated elastin fibers.
  • compositions of the present invention are not intended to be limiting thereof. All percentages and ratios are based on weight unless otherwise specified.
  • Red pigment (Red #202 according to MHW Regulation)
  • Red pigment (Red #201 according to MHW Regulation)
  • Yellow pigment (Yellow #4 Aluminum lake according to MHW Regulation)
  • the lipsticks as shown as Examples 1-3 in Table 1 can be prepared by a suitable process to one skilled in the art. As a preferred process, the following can be used. Acidic dye, oil-base dye, and pigment are mixed with a certain amount of castor oil respectively. Anhydrous citric acid is dissolved in the solvent to make a 5% solution. The dye mixture, pigment mixture, and organic acid solution thus obtained are mixed with the other components which had been melted and dissolved at 100-120°C. The finally obtained mixture is poured into a mold to obtain a stick-type lipstick.

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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)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

Composition cosmétique solide lipophile comprenant 0,01 à 1 % en poids de colorant acide et 0,01 à 0,5 % en poids d'acide organique hydrosoluble ayant un ou plusieurs groupes fonctionnels. Ladite composition cosmétique présente un bon pouvoir colorant, un effet de longue durée et une bonne stabilité de la couleur. Dans un mode de réalisation préféré de la présente invention, ladite composition comprend en outre un colorant à base d'huile. Dans un autre mode de réalisation préféré, l'acide organique hydrosoluble est introduit dans la composition en tant que solution de solvant.
PCT/US1994/014288 1993-12-24 1994-12-15 Composition cosmetique solide lipophile comprenant un colorant acide WO1995017884A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU14006/95A AU699995B2 (en) 1993-12-24 1994-12-15 Lipophilic solid cosmetic composition comprising acidic dye
EP95905358A EP0742710A1 (fr) 1993-12-24 1994-12-15 Composition cosmetique solide lipophile comprenant un colorant acide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5/328024 1993-12-24
JP5328024A JP2831552B2 (ja) 1993-12-24 1993-12-24 酸性染料を含有する油性固型化粧料

Publications (1)

Publication Number Publication Date
WO1995017884A1 true WO1995017884A1 (fr) 1995-07-06

Family

ID=18205673

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/014288 WO1995017884A1 (fr) 1993-12-24 1994-12-15 Composition cosmetique solide lipophile comprenant un colorant acide

Country Status (7)

Country Link
EP (1) EP0742710A1 (fr)
JP (1) JP2831552B2 (fr)
CN (1) CN1113642C (fr)
AU (1) AU699995B2 (fr)
CA (1) CA2179279A1 (fr)
CZ (1) CZ174996A3 (fr)
WO (1) WO1995017884A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003068176A1 (fr) * 2002-02-14 2003-08-21 Bonne Bell, Inc. Produit cosmetique pour les levres a gout acide

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2735688B1 (fr) * 1995-06-26 1997-08-14 Oreal Utilisation en association d'un alpha-hydroxyacide et d'un oxyde de titane pour le blanchiment de la peau
JP4643366B2 (ja) * 2005-06-06 2011-03-02 株式会社資生堂 油性固形化粧料
JP5944290B2 (ja) * 2012-09-26 2016-07-05 株式会社マンダム 退色が防止された組成物及び化粧品
JP6034986B2 (ja) * 2015-01-21 2016-11-30 株式会社 資生堂 メーキャップ化粧料
WO2016117640A1 (fr) * 2015-01-21 2016-07-28 株式会社 資生堂 Produit cosmétique de maquillage
JP6153275B1 (ja) 2016-04-28 2017-06-28 高級アルコール工業株式会社 化粧料
JP6921504B2 (ja) * 2016-11-21 2021-08-18 ロレアル メイクアップに使用するための固体化粧用組成物
JP7209179B2 (ja) * 2018-12-05 2023-01-20 日本メナード化粧品株式会社 油溶性染料の溶解方法及び油溶性染料溶液

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4305961A (en) * 1978-09-28 1981-12-15 Kao Soap Co., Ltd. Cosmetic composition
US4438140A (en) * 1980-04-18 1984-03-20 Societe Anonyme Dite: L'oreal Salts of acid dyes and copolymers having tertiary amine functions, process for preparing said salts and makeup cosmetic compositions containing them
US4952245A (en) * 1988-07-22 1990-08-28 Kao Corporation Nacreous pigment containing a dye and cosmetic composition comprising the same
US5171572A (en) * 1990-03-07 1992-12-15 Kao Corporation Barium sulfate and cosmetic compositions comprising same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4305961A (en) * 1978-09-28 1981-12-15 Kao Soap Co., Ltd. Cosmetic composition
US4438140A (en) * 1980-04-18 1984-03-20 Societe Anonyme Dite: L'oreal Salts of acid dyes and copolymers having tertiary amine functions, process for preparing said salts and makeup cosmetic compositions containing them
US4952245A (en) * 1988-07-22 1990-08-28 Kao Corporation Nacreous pigment containing a dye and cosmetic composition comprising the same
US5171572A (en) * 1990-03-07 1992-12-15 Kao Corporation Barium sulfate and cosmetic compositions comprising same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003068176A1 (fr) * 2002-02-14 2003-08-21 Bonne Bell, Inc. Produit cosmetique pour les levres a gout acide

Also Published As

Publication number Publication date
JPH07206635A (ja) 1995-08-08
CN1113642C (zh) 2003-07-09
EP0742710A1 (fr) 1996-11-20
CN1138293A (zh) 1996-12-18
AU1400695A (en) 1995-07-17
JP2831552B2 (ja) 1998-12-02
CA2179279A1 (fr) 1995-07-06
AU699995B2 (en) 1998-12-17
CZ174996A3 (en) 1997-01-15

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