WO1994024997A1 - Antiperspirant stick compositions exhibiting improved wash-off performance - Google Patents
Antiperspirant stick compositions exhibiting improved wash-off performance Download PDFInfo
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- WO1994024997A1 WO1994024997A1 PCT/US1994/004219 US9404219W WO9424997A1 WO 1994024997 A1 WO1994024997 A1 WO 1994024997A1 US 9404219 W US9404219 W US 9404219W WO 9424997 A1 WO9424997 A1 WO 9424997A1
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- esters
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- 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
- A61K8/0216—Solid or semisolid forms
- A61K8/0229—Sticks
-
- 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
- A61K8/18—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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/05—Stick
Definitions
- the present invention relates to antiperspirant compositions; and more particularly, to antiperspirant stick compositions.
- Personal hygienic habits typically include a means for reducing human body odors. These habits include routine bathing or washing the body; particularly the axilla. Typically, the axilla is also treated with compositions to retard odor formation, such as antiperspirant compositions. Generally, various ingredients from the antiperspirant composition remain on the skin from the previous application at the time washing of the axilla occurs. Thus, it is highly desirable that the ingredients within the antiperspirant composition - particularly those which might impart a sticky, or tacky feel to the axilla - are readily washed off.
- Antiperspirant compositions can take a number of different forms, each dependent on the ingredients used in addition to the above mentioned astringent metallic salts.
- the forms include lotions, solid sticks, and creams; the most popular being solid sticks.
- Solid stick antiperspirant compositions include wax sticks and gel sticks.
- Antiperspirant gel sticks utilize a gellant as a solidifying agent to impart the solid stick structure to the composition.
- antiperspirant wax sticks utilize an aliphatic alcohol wax as a solidifying agent.
- antiperspirant sticks generally include non-volatile emollients to provide desirable aesthetic characteristics (e.g., not having a sticky, tacky and/or wet feel).
- non-volatile emollients to provide desirable aesthetic characteristics (e.g., not having a sticky, tacky and/or wet feel).
- the combination of solidifying agents with the non-volatile emollients can be resistant to being washed off the skin after use. The present invention, however, solves this problem by improving the wash-off performance of such sticks.
- the composition includes: a. a solidifying agent; b. a liquid base material including a non-polar, non- volatile emollient; c. an antiperspirant active; and d.
- a wash-off agent selected from the group consisting of polyoxyethylene ethers having the formula R ] (OCH2CH2) n OH; polyoxyethylene esters having the formula R ⁇ CO(OCH2CH2) n OH; polyoxyethylene diesters having the formula R ⁇ CO(OCH2CH2) n OOCR2; polyoxyethylene glyceryl esters having the formula (R ⁇ COO)CH2CH(OH)CH 2 (OCH2CH 2 ) n OH or having the formula HOCH 2 CH(OOCR 1 )CH2(OCH2CH 2 ) n OH; and polyoxyethylene glyceryl diesters having the formula R 1 COOCH 2 CH(OOCR2)CH 2 (OCH2CH2)nOH wherein:
- Rj is an alkyl, alkenyl, or aromatic hydrocarbon radical having from about 4 to about 50 carbon atoms;
- R2 is an identical or different alkyl, alkenyl, or aromatic hydrocarbon radical having from about 4 to about 22 carbon atoms;
- n is from about 2 to about 80; and wherein the wash-off agent has a solubility parameter of at least about 7.
- Antiperspirant stick compositions of the present invention which exhibit improved wash-off performance may comprise, consist of, or consist essentially of the essential elements described herein as well as one or more of the preferred or optional ingredients described herein.
- solidifying agent means materials which are effective at physically and/or chemically altering the liquid base material so as to form a final stick composition which is a stable stick at ambient conditions and is deposited on the skin during normal use conditions.
- the level of the solidifying agent in antiperspirant stick compositions of the present invention is preferably from about 1% to about 25%.
- the level of solidifying agent is more preferably from about 10% to about 20%; and even more preferably, from about 10% to about 15%.
- the level of the solidifying agent is more preferably from about 3% to about 12%; and even more preferably from about 5% to about 10%.
- Waxes as Solidifying Agents Waxes are frequently used as solidifying agents in antiperspirant stick compositions which are commonly referred to as wax sticks. Particularly useful are waxes having a low melting point, i.e., having a melting point of from about 37°C to 75°C. Such low melting point waxes are well known in the art and include fatty acids, fatty alcohols, fatty acid esters, fatty acid amides; all preferably having fatty chains from about 8 to about 30 carbon atoms, and more preferably from about 12 to about 22 carbon atoms.
- Preferred low melting point waxes include cetyl alcohol, palmitic acid, myristyl alcohol, stearyl alcohol, behenyl alcohol, paraffin, and mixtures thereof.
- the ratio of n-acyl amino acid amide to the 12-hydroxystearic acid, esters of 12-hydroxystearic acid, and/or amides of 12-hydroxystearic acid is preferably from about 1:20 to about 2:1; more preferably from about 1 : 10 to about 1:1;, and most preferably from about 1 :7 to about 1:2; and the level of n-acyl amino acid amide is at least about 0.1% total weight of the gel stick composition.
- n-acyl amino acid amides are prepared from glutamic acid, lysine, glutamine, aspartic acid and mixtures thereof. Particularly preferred are n-acyl glutamic acid amides corresponding to the following formula: 0 0
- R is an aliphatic hydrocarbon radical having from about 12 to about 22 carbon atoms
- R ⁇ is an aliphatic hydrocarbon radical having from about 2 to about 22 carbon atoms.
- Non-limiting examples of these include n-lauroyl-L- glutamic acid dibutyl amide, n-stearoyl-L-glutamic acid diheptyl amide, and mixtures thereof.
- N-lauroyl-L-glutamic acid diethyl amide N- lauroyl-L-glutamic acid dibutyl amide, N-lauroyl-L-glutamic acid diheptyl amide, N-lauroyl-L-glutamic acid dioctyl amide, N-lauroyl-L-glutamic acid didecyl amide, N-lauroyl-L-glutamic acid didecyl amide, N-lauroyl-L-glutamic acid didecyl amide, N-lauroyl-L-glutamic acid ditetradecyl amide, N-lauroyl-L-glutamic acid dihexadecyl amide, N-lauroyl-L-glutamic acid distearyl amide, N-stearoyl-L-glutamic acid diethyl amide, N-stearoyl-L-glutamic acid dibutyl amide, N-ste
- n-lauroyl-L-glutamic acid dibutyl amide Most preferred is n-lauroyl-L-glutamic acid dibutyl amide. Additional information regarding the use of n-acyl amino acids as gellants are found in the following references: U.S. Pat. 3,969,087 issued on July 13, 1976 to Saito et al.; Japanese Patent Application 1-207223 which published August 21, 1989; and Japanese Patent Application 2-180805 which published July 13, 1988.
- the base matrix of antiperspirant stick compositions of the present invention is formed by combining the above solidifying agent with a liquid base material.
- liquid refers to materials which are liquids at ambient conditions and the ternY'liquid base material” includes all liquids within the composition except the wash-off agent described below. It is important that the liquid base material selected is of a type, and at such a level to sufficiently solubilize the solidifying agent when heated, and form a stick when cooled to ambient temperature.
- the liquid base material must be compatible with the solidifying agent so that the mixture of the two does not phase separate during processing.
- liquid base materials are typically selected in order to provide aesthetic benefits, such as emolliency, low tack or minimized visible residue, without substantial interference with the effectiveness of the antiperspirant active component.
- the particular liquid base material should be safe for application to human skin.
- Solubility parameters are common to the art of antiperspirant stick formulation and the means to determine them are disclosed by CD. Vaughan, "Solubility Effects in Product, Package, Penetration and Preservation” 103 Cosmetics and Toiletries 47- 69, October, 1988; and CD. Vaughan, " Using Solubility Parameters in Cosmetics Formulation", 36 J Soc. Cosmetic Chemists 319-333, Sept Oct, 1985.
- the liquid base materials of the present invention are preferably used at levels from about 10% to about 95%; and more preferably from about 30% to about 80%. Included in the liquid base materials are one or more non-polar, non-volatile liquid emollients as described below preferably at levels from about 5% to about 60%; more preferably from about 5% to about 25%; and most preferably from about 7% to about 20%. Furthermore, the liquid base materials may optionally include one or more non-polar, volatile liquid emollients as described below. The volatile liquid emollients, when used, are preferably used at levels from about 10% to about 70%; more preferably, from about 25% to about 60%; and more preferably, from about 40% to about 60%. 2. Non-polar.
- Non-volatile Liquid Emollients Non-polar, non-volatile liquid emollients useful in the present invention are disclosed in Cosmetics, Science, and Technology, Vol. 1, 27-104 edited by Balsam and Sagarin, 1972; U.S. Pat. 4,202,879 issued to Shelton on May 13, 1980; and U.S. Pat. 4,816,261 issued to Luebbe et al. on March 28, 1989.
- Non-volatile refers to materials which exhibit a vapor pressure of no more than about 0.2mm Hg at 25°C at one atmosphere and/or to materials which have a boiling point at one atmosphere of at least about 300°C
- Non-polar, non-volatile liquid emollients useful in the present invention are preferably selected from the group consisting of silicone oils; hydrocarbon oils; fatty alcohols; fatty acids; esters of mono and dibasic carboxylic acids with mono and polyhydric alcohols; polyoxyethylenes; polyoxypropylenes; mixtures of polyoxyethylene and polyoxypropylene ethers of fatty alcohols; and mixtures thereof.
- propoxylated ethers of C 14-C ⁇ g fatty alcohols having a degree of propoxylation below about 50 esters of C2*-Cg alcohols and C*.2 _ C26 carboxylic acids (e.g. ethyl myristate, isopropyl palmitate), esters of C, * ⁇ 26 a ⁇ co ⁇ 10 ⁇ s an ⁇ benzoic acid (e.g.
- hexyldecanol Even more preferred is hexyldecanol, octyldecanol, octyldodecanol and undecylpentadecanol; and most prefered is octyldodecanol.
- Such preferred aliphatic fatty alcohols are particularly useful in combination with the volatile liquid silicone oils discussed below to adjust the average solubility of the liquid base material.
- non-volatile silicone oils useful in the present invention are essentially non-volatile polyalkylsiloxanes selected from the group consisting of polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, poly-ethersiloxane copolymers, and mixtures thereof.
- polydimethyl siloxanes having viscosities of from about 5 to about 100,000 centistokes at 25 °C examples include polydimethyl siloxanes having viscosities from about 5 to about 100,000 centistokes at 25 °C
- preferred non-volatile silicone emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from about 2 to about 400 centistokes at 25°C
- polyalkylsiloxanes include the Viscasil series (sold by General Electric Company) and the Dow Corning 200 series (sold by Dow Corning Corp.).
- Polyalkylarylsiloxanes include polymethylphenyl siloxanes having viscosities of from about 15 to about 65 centistokes at 25 °C These are available, for example, as SF 1075 methyl-phenyl fluid (sold by General Electric Company) and 556 Cosmetic Grade Fluid (sold by Dow Corning Corp.).
- Useful poly- ethersiloxane copolymers include, for example, a polyoxyalkylene ether copolymer having a viscosity of about 1200 to 1500 centistokes at 25°C Such a fluid is available as SF1066 organosilicone surfactant (sold by General Electric Company).
- Polysiloxane ethylene glycol ether copolymers are preferred copolymers for use in the present compositions.
- Non-volatile paraffinic hydrocarbon oils useful in the present invention include mineral oils and certain branched-chain hydrocarbons. Examples of these fluids are disclosed in U.S. Pat. 5,019,375 issued to Tanner et al. on May 28, 1991. Preferred mineral oils have the following properties:
- Particularly preferred branched-chain hydrocarbons include Permethyl 103 A, which contains an average of about 24 carbon atoms; Permethyl 104 A, which contains an average of about 68 carbon atoms; Permethyl 102A, which contains an average of about 20 carbon atoms; all of which may be purchased from Permethyl
- Ethylflo 364 which contains a mixture of 30 carbon atoms and 40 carbon atoms and may be purchased from Ethyl Corp.
- Non-polar. Volatile Liquid Emollients The optional non-polar, volatile liquid emollients useful in the present invention are known in the art as disclosed, for example, in Cosmetics, Science, and Technology, Vol. 1, 27-104 edited by Balsam and Sagarin, 1972; U.S. Pat. 4,202,879 issued to Shelton on May 13, 1980; and U.S. Pat. 4,816,261 issued to Luebbe et al. on March 28, 1989.
- the term "volatile” as used herein refers to all materials which are not “non-volatile” as previously defined herein.
- Non-polar, volatile liquid emollients particularly useful in the present invention are selected from the group consisting of silicone oils; hydrocarbons; and mixtures thereof.
- the emollients useful in the present invention may be either saturated or unsaturated, have an aliphatic character and be straight or branched chained or contain alicyclic or aromatic rings.
- volatile hydrocarbons include isodecane (such as Permethyl-99A which is available from Presperse Inc.) and the C -Cg through C12-C15 isoparaffins (such as the Isopar Series available from Exxon Chemicals).
- volatile liquid silicone oils are particularly useful as the non- polar emollients in the liquid base material since they endow the antiperspirant stick composition with highly desirable aesthetics.
- Volatile silicone oils preferably comprise from about 10% to about 70%; more preferably, from about 25% to about 60%; more preferably from about 40% to about 60%; and most preferably, about 50%.
- Volatile liquid silicone oils are disclosed in U.S. Pat. 4,781,917 issued to Luebbe et al. on Nov. 1, 1988. Additionally, a description of various volatile silicones materials is found in Todd et al., "Volatile Silicone Fluids for Cosmetics", Cosmetics and Toiletries, 91:27-32 (1976). Particularly preferred volatile silicone oils are selected from the group consisting of cyclic volatile silicones corresponding to the formula: CH 3
- n is from about 3 to about 7; and linear volatile silicones corresponding to the formula:
- compositions of the present invention also contain an astringent antiperspirant active. These actives are used at levels from about 0.5% to about 60%, preferably from about 5% to about 35%, of the antiperspirant gel stick composition. This active may be incorporated either in solubilized or particulate form. These weight percentages are calculated on an anhydrous metal salt basis (exclusive of glycine, the salts of glycine, or other complexing agents).
- the material preferably has a particle size of from about 1 to about 100 microns, preferably from about 1 to about 50 microns, and have a high bulk density (e.g., greater than about 0.7 g/cm3).
- Such materials include, for example, many aluminum or zirconium astringent salts or complexes and are well known in the antiperspirant art. Any aluminum astringent antiperspirant salt or aluminum and/or zirconium astringent complex can be employed herein.
- Salts useful as astringent antiperspirant salts or as components of astringent complexes include aluminum halides, aluminum hydroxy-halides, zirconyl oxyhalides, zirconyl hydroxy-halides, and mixtures of these materials.
- Aluminum salts of this type can be prepared in the manner described more fully in U.S. Patent 3,887,692 issued to Gilman on June 3, 1975, and U.S. Patent 3,904,741 issued to Jones and Rubino on September 9, 1975.
- the above formula is greatly simplified and is intended to represent and include compounds having coordinated and/or bound water in various quantities, as well as polymers, mixtures and complexes of the above.
- the zirconium hydroxy salts actually represent a range of compounds having various amounts of the hydroxy group, varying from about 1.1 to only slightly greater than 0 groups per molecule.
- ZAG complexes useful herein are identified by the specification of both the molar ratio of aluminum to zirconium (hereinafter “Al:Zr” ratio) and the molar ratio of total metal to chlorine (hereinafter “Metal:Cl” ratio).
- ZAG complexes useful herein have an Al:Zr ratio of from about 1.67 to about 12.5 and a Metal :C1 ratio of from about 0.73 to about 1.93.
- Preferred ZAG complexes are formed by
- p parts neutral amino acid selected from the group consisting of glycine, dl-tryptophane, dl-b-phenylalanine, dl-valine, dl-methionine and b-alanine, and where p has a value of from about 0.06 to about 0.53;
- a preferred aluminum compound for preparation of such ZAG type complexes is aluminum chlorhydroxide of the empirical formula
- preferred compounds include the 5/6 basic aluminum salts of the empirical formula Al 2 (OH)5C1.2H 2 O; mixtures of AlCl 3 .6H 2 O and Al 2 (OH) 5 Cl. 2H O with aluminum chloride to aluminum hydroxychloride weight ratios of up to about 0.5; ZAG type complexes wherein the zirconium salt is ZrO(OH)C1.3H2O, the aluminum salt is _ ⁇ 2(OH)$Cl 2H- or the aforementioned mixtures of AlCl 3 .6H2 ⁇ and Al2(OH)s CI.2H2O wherein the total metal to chloride molar ratio in the complex is less than about 1.25 and the Al:Zr molar ratio is about 3.3, and the amino acid is glycine; and ZAG-type complexes wherein the zirconium salt is ZrO(OH)2- a Cl .11H2O wherein a is from about 1.5 to about 1.87 and n
- Solubilized antiperspirant actives which may be utilized in the present invention are also well known in the art. These materials utilize monohydric or polyhydric alcohols or water to solubilize the antiperspirant active before it is incorporated into the product. The levels of these polar solvents is less than 25%, and preferably less than 15% of the composition. Examples of such actives are taught, for example, in U.S. Patent 4,137,306 issued to Rubino on January 30, 1979; U.S. Patent Application Serial No. 370,559, Smith and Ward, filed June 23, 1989; and European Patent Application 0295070 which published December 14, 1988.
- the wash-off agent improves the ease with which the ingredients - particularly the solidifying agent and the non-polar, non- volatile oils - may be washed off.
- the wash-off agent is highly preferably a non-liquid. In the case where the wash-off agent is a liquid, the wash-off agent should be miscible in the liquid base material and is not considered part of the liquid base material.
- the wash-off agent is preferably in the antiperspirant stick composition in an amount from about 0.1% to about 10%; preferably, from about 1% to about 5%; and more preferably, from about 1% to about 3%.
- the wash-off agent must be soluble in the amounts described above in the molten product matrix at reasonable process temperatures, i.e., preferably from about 80°C to about 130°C; more preferably from about 80°C to about 110°C
- the solubility parameter of the wash- off agent is at least about 7; more preferably, from about 7.5 to about 11.
- the wash-off agent of the present invention is - highly preferably, a non-liquid - selected from the group consisting of polyoxyethylene ethers having the formula . Rl(OCH2CH2) n H; polyoxyethylene esters having the formula R j CO(OCH2CH2)nOH; polyoxyethylene diesters having the formula
- RlCO(OCH2CH2) n OOCR2 polyoxyethylene glyceryl esters having the formula (R 1 COO)CH2CH(OH)CH 2 (OCH2CH 2 )nOH or having the formula HOCH2CH(OOCR ⁇ )CH2(OCH2CH2) n OH; and polyoxyethylene glyceryl diesters having the formula R 1 COOCH2CH(OOCR2)CH2(OCH 2 CH2) n OH - preferably, the polyoxyethylene ethers - wherein:
- K is an alkyl, alkenyl, or aromatic hydrocarbon radical which may be substituted or unsubstituted - preferably an alkyl radical - having a lower limit of about 4 carbon atoms; preferably, about 12 carbon atoms; more preferably, about 14 carbon atoms; and most preferably, about 16 carbon atoms; and an upper limit of about 50 carbon atoms; more preferably, 35 carbon atoms; even more preferably, 22 carbon atoms; preferably, about 20 carbon atoms; and most preferably, about 18 carbon atoms; and wherein:
- R2 is an identical or different alkyl, alkenyl, or aromatic hydrocarbon radical which may be substituted or unsubstituted - preferably an alkyl radical - having a lower limit of about 4 carbon atoms; preferably, about 12 carbon atoms; more preferably, about 14 carbon atoms; and most preferably, about 16 carbon atoms; and an upper limit of about 22 carbon atoms; preferably, about 20 carbon atoms; and most preferably, about 18 carbon atoms; and wherein: n has a lower limit of about 2; preferably, about 4, more preferably, about 6; even more preferably, about 8; even more preferably, about 10 and most preferably, about 15; and wherein n has an upper limit of about 80; preferably, about 70; more preferably, about 60; even more preferably, about 50; even more preferably, about 40; even more preferably, about 30; and even more preferably, about 25.
- wash-off agents include: ceteth-2 through ceteth-30, steareth-2 through steareth-30, ceteareth-2 through ceteareth- 30, PEG-2 stearate through PEG-30 stearate, PEG-8 distearate, PEG-12 isostearate, C20-40 pareth-10, C20-40 pareth-40, PEG- 16 hydrogenated castor oil, PEG-40 hydrogenated castor oil, and PEG-20 glyceryl stearate; more preferably, ceteareth-20, steareth-21, PEG-20 stearate, and PEG- 16 hydrogenated castor oil; and most preferably, ceteareth-20.
- Antiperspirant stick compositions of the present invention may contain optional components which act as additional active or modify the physical characteristics of the composition or the components making up said compositions.
- optional components are well known in the art.
- a non-limiting group of these optional components include colorants, perfumes, thickeners, distributing agents, emulsifiers, bacteriostats, fungistats, and mixtures thereof.
- Optional components useful herein are described in the following references: U.S. Patent 4,049,792 issued to Elsnau on September 20, 1977; Canadian Patent 1,164,347 which issued to Beckmeyer et al.
- Thickeners are also useful in the present invention; particularly with gel sticks. Their selection and the level they are used at should be so as not to significantly affect the aesthetics of the stick composition. Typical levels of thickeners are at levels of less than about 5%. Examples of said thickeners are disclosed in U.S. Pat. 4,985,238 issued to Tanner et al. on JanJ5, 1991. These thickeners include wax-like materials such as beeswax, cerasin, hydrogenated castor oil, synthetic waxes such as Fisher Tropsch waxes, microcrystalline waxes, polyethylene waxes, and mixtures thereof.
- the solidifying agent Combine the solidifying agent, the liquid base material and the wash-off agent into a vessel equipped with a heat source. Heat the mixture to a temperature from about 80°C to about 130°C with stirring, until the mixture forms a clear homogeneous solution. Once clear, the solution is cooled and held at approximately 65- 120°C at which time the antiperspirant active (and other optional components such as filler powders or perfumes) is added into the above vessel and mixed thoroughly into the composition. The mixture is then poured into containers and allowed to cool. Upon cooling a stable antiperspirant stick is obtained. Alternatively, the antiperspirant active may be added along with the solidifying agent, the liquid base material and the wash-off agent in the first step.
- the present invention provides methods for preventing perspiration and malodor associated with human perspiration. These methods comprise applying to the skin of a human a safe and effective amount of the antiperspirant gel of the present invention.
- a safe and effective amount as used herein, is an amount which is effective in eliminating or substantially reducing malodor associated with human underarm perspiration while being safe for human use at a reasonable rislo'benefit ratio.
- the safe and effective amount used is from about 0.1 gram per axilla to about 1.0 gram per axilla.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6524345A JPH08509729A (en) | 1993-04-27 | 1994-04-11 | Antiperspirant stick composition showing improved wash-off performance |
AU67064/94A AU697551B2 (en) | 1993-04-27 | 1994-04-11 | Antiperspirant stick compositions exhibiting improved wash-off performance |
EP94914816A EP0696188B1 (en) | 1993-04-27 | 1994-04-11 | Antiperspirant stick compositions exhibiting improved wash-off performance |
DE69404646T DE69404646T2 (en) | 1993-04-27 | 1994-04-11 | ANTI-TRANSPIRANT PEN COMPOSITION WITH IMPROVED WASH REMOVAL |
BR9406438A BR9406438A (en) | 1993-04-27 | 1994-04-11 | Antiperspirant stick compositions exhibiting improved washing performance |
NO954258A NO954258L (en) | 1993-04-27 | 1995-10-25 | Antiperspirant stick blends with improved washability |
FI955109A FI955109A (en) | 1993-04-27 | 1995-10-26 | Antiperspirant stick-like compositions with improved wash-off properties |
GR970401655T GR3024320T3 (en) | 1993-04-27 | 1997-07-31 | Antiperspirant stick compositions exhibiting improved wash-off performance |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5361893A | 1993-04-27 | 1993-04-27 | |
US11059693A | 1993-08-23 | 1993-08-23 | |
US08/053,618 | 1993-08-23 | ||
US08/110,596 | 1993-08-23 |
Publications (1)
Publication Number | Publication Date |
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WO1994024997A1 true WO1994024997A1 (en) | 1994-11-10 |
Family
ID=26732057
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1994/004219 WO1994024997A1 (en) | 1993-04-27 | 1994-04-11 | Antiperspirant stick compositions exhibiting improved wash-off performance |
Country Status (14)
Country | Link |
---|---|
US (1) | US5733534A (en) |
EP (1) | EP0696188B1 (en) |
JP (1) | JPH08509729A (en) |
AT (1) | ATE156011T1 (en) |
AU (1) | AU697551B2 (en) |
BR (1) | BR9406438A (en) |
CA (1) | CA2160364A1 (en) |
DE (1) | DE69404646T2 (en) |
DK (1) | DK0696188T3 (en) |
ES (1) | ES2105704T3 (en) |
FI (1) | FI955109A (en) |
GR (1) | GR3024320T3 (en) |
NO (1) | NO954258L (en) |
WO (1) | WO1994024997A1 (en) |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4511554A (en) * | 1980-06-02 | 1985-04-16 | Bristol-Myers Company | Non-staining antiperspirant stick composition |
EP0291334A2 (en) * | 1987-05-15 | 1988-11-17 | Unilever Plc | Transparent antiperspirant stick compositions |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE554681A (en) * | 1956-03-01 | |||
US3255082A (en) * | 1962-04-16 | 1966-06-07 | Procter & Gamble | Method of preparing stable aluminum chlorhydrate-alkali metal- and alkaline earth metal salt complex antiperspirant stick |
US3904741A (en) * | 1970-10-26 | 1975-09-09 | Armour Pharma | Alcohol soluble basic aluminum chlorides and method of making same |
US4137306A (en) * | 1973-06-05 | 1979-01-30 | Armour Pharmaceutical Company | Anhydrous antiperspirant stick compositions |
US4049792A (en) * | 1973-06-26 | 1977-09-20 | The Procter & Gamble Company | Antiperspirant stick |
US3903258A (en) * | 1973-08-06 | 1975-09-02 | Gillette Co | Zirconium aluminum complexes and method of making the same |
US4017599A (en) * | 1973-11-23 | 1977-04-12 | Armour Pharmaceutical Company | Aluminum-zirconium anti-perspirant systems with salts of amino acids |
US3979510A (en) * | 1973-11-23 | 1976-09-07 | Armour Pharmaceutical Company | Aluminum-zirconium anti-perspirant systems with complex aluminum buffers |
US3981896A (en) * | 1974-03-01 | 1976-09-21 | Hoffmann-La Roche Inc. | Phenylsiloxy vanadium oxide catalysts |
US3969087A (en) * | 1974-08-07 | 1976-07-13 | Ajinomoto Co., Ltd. | Gels of nonpolar liquids with N-acyl amino acids and derivatives thereof as gelling agents |
US3970748A (en) * | 1975-02-24 | 1976-07-20 | Schuylkill Chemical Company | Aluminum chlorhydroxy glycinate complexes |
NL183868C (en) * | 1975-10-17 | 1989-02-16 | Naarden International Nv | SOLID, ANHYDROUS, TRANSPARENT GELATED ANTI-TRANSPIRATION COMPOSITIONS, AND A METHOD FOR PREPARING SUCH COMPOSITIONS. |
CA1075158A (en) * | 1976-02-05 | 1980-04-08 | Peter F. Davy | Siloxane with alcohol in antiperspirant stick |
CA1089368A (en) * | 1976-08-02 | 1980-11-11 | Daniel C. Geary | Polyethoxylated fatty alcohol in antiperspirant sticks |
US4202879A (en) * | 1977-07-18 | 1980-05-13 | The Procter & Gamble Company | Three phase antiperspirant stick |
US4722836A (en) * | 1977-12-08 | 1988-02-02 | American Cyanamid Company | Suspension type antiperspirant stick |
US4226889A (en) * | 1978-12-19 | 1980-10-07 | Dragoco, Inc. | Cosmetic stick composition |
DE3068546D1 (en) * | 1979-11-07 | 1984-08-16 | Procter & Gamble | Antiperspirant compositions |
US4371645A (en) * | 1980-04-24 | 1983-02-01 | Milliken Research Corporation | Polyolefin plastic compositions comprising meta- or papa-derivatives (choro- or bromo-) of di-benzyuidene sorbitol |
US4518582A (en) * | 1982-04-30 | 1985-05-21 | American Cyanamid Company | Acid stable dibenzyl monosorbitol acetal gels |
ATE55898T1 (en) * | 1983-01-26 | 1990-09-15 | Procter & Gamble | COSMETIC PENS. |
US4719102A (en) * | 1983-02-15 | 1988-01-12 | American Cyanamid Company | Acid stable dibenzyl monosorbitol acetal gels |
US4725430A (en) * | 1984-04-03 | 1988-02-16 | American Cyanamid Company | Acid stable dibenzyl monosorbitol acetal gels |
US4722835A (en) * | 1984-09-21 | 1988-02-02 | American Cyanamid Company | Dibenzyl monosorbitol acetal gel antiperspirant stick compositions |
US4944937A (en) * | 1984-12-19 | 1990-07-31 | The Procter & Gamble Company | Cosmetic sticks |
US4724139A (en) * | 1985-05-08 | 1988-02-09 | Victor Palinczar | Antiperspirant stick |
US4822603A (en) * | 1986-06-18 | 1989-04-18 | The Procter & Gamble Company | Antiperspirant stick composition and process for preparing the same |
US4822602A (en) * | 1987-04-29 | 1989-04-18 | The Procter & Gamble Company | Cosmetic sticks |
US4948578A (en) * | 1987-05-15 | 1990-08-14 | Lever Brothers Company | Transparent antiperspirant stick compositions |
EP0295071A3 (en) * | 1987-06-11 | 1989-05-10 | The Procter & Gamble Company | Low residue wax emulsion antiperspirant sticks |
US4781917A (en) * | 1987-06-26 | 1988-11-01 | The Proctor & Gamble Company | Antiperspirant gel stick |
US4816261A (en) * | 1987-11-20 | 1989-03-28 | The Procter & Gamble Company | Deodorant gel stick |
JPH01207223A (en) * | 1988-02-12 | 1989-08-21 | Kobayashi Kose Co Ltd | Solid cosmetics |
US4944938A (en) * | 1988-12-16 | 1990-07-31 | Colgate-Palmolive Company | Antiperspirant and deodorant |
JP2744267B2 (en) * | 1988-12-29 | 1998-04-28 | 株式会社資生堂 | External preparation for skin |
US4919934A (en) * | 1989-03-02 | 1990-04-24 | Richardson-Vicks Inc. | Cosmetic sticks |
US5019375A (en) * | 1989-03-14 | 1991-05-28 | The Procter & Gamble Company | Low residue antiperspirant creams |
US4985238A (en) * | 1989-03-14 | 1991-01-15 | The Procter & Gamble Company | Low residue antiperspirant sticks |
JP2791093B2 (en) * | 1989-04-03 | 1998-08-27 | 鐘紡株式会社 | Solid cosmetics |
DE69020949T2 (en) * | 1989-05-03 | 1996-03-21 | Gillette Co | Antiperspirant. |
US5258174A (en) * | 1990-03-21 | 1993-11-02 | Colgate-Palmolive Company | Clear stick anti-perspirant |
AU673672B2 (en) * | 1992-05-12 | 1996-11-21 | Procter & Gamble Company, The | Antiperspirant gel stick composition |
-
1994
- 1994-04-11 AU AU67064/94A patent/AU697551B2/en not_active Withdrawn - After Issue
- 1994-04-11 WO PCT/US1994/004219 patent/WO1994024997A1/en not_active Application Discontinuation
- 1994-04-11 ES ES94914816T patent/ES2105704T3/en not_active Expired - Lifetime
- 1994-04-11 BR BR9406438A patent/BR9406438A/en not_active IP Right Cessation
- 1994-04-11 EP EP94914816A patent/EP0696188B1/en not_active Revoked
- 1994-04-11 CA CA002160364A patent/CA2160364A1/en not_active Abandoned
- 1994-04-11 JP JP6524345A patent/JPH08509729A/en not_active Ceased
- 1994-04-11 DK DK94914816.7T patent/DK0696188T3/en active
- 1994-04-11 AT AT94914816T patent/ATE156011T1/en not_active IP Right Cessation
- 1994-04-11 DE DE69404646T patent/DE69404646T2/en not_active Revoked
-
1995
- 1995-02-16 US US08/390,901 patent/US5733534A/en not_active Expired - Fee Related
- 1995-10-25 NO NO954258A patent/NO954258L/en unknown
- 1995-10-26 FI FI955109A patent/FI955109A/en unknown
-
1997
- 1997-07-31 GR GR970401655T patent/GR3024320T3/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4511554A (en) * | 1980-06-02 | 1985-04-16 | Bristol-Myers Company | Non-staining antiperspirant stick composition |
EP0291334A2 (en) * | 1987-05-15 | 1988-11-17 | Unilever Plc | Transparent antiperspirant stick compositions |
Cited By (29)
Publication number | Priority date | Publication date | Assignee | Title |
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US5516511A (en) * | 1994-05-06 | 1996-05-14 | The Procter & Gamble Company | Antiperspirant gel compositions comprising chelators |
WO1995030405A1 (en) * | 1994-05-06 | 1995-11-16 | The Procter & Gamble Company | Antiperspirant gel compositions comprising chelators |
AU708128B2 (en) * | 1994-05-06 | 1999-07-29 | Procter & Gamble Company, The | Antiperspirant gel compositions comprising chelators |
GB2299270B (en) * | 1995-03-30 | 1998-11-18 | Unilever Plc | Antiperspirant compositions |
GB2299270A (en) * | 1995-03-30 | 1996-10-02 | Unilever Plc | Clear antiperspirant gel comprising zirconium and a polyhydroxy surfactant |
AU719304B2 (en) * | 1995-03-30 | 2000-05-04 | Unilever Plc | Antiperspirant compositions |
US5635165A (en) * | 1995-09-27 | 1997-06-03 | Helene Curtis, Inc. | Antiperspirant deodorant compositions |
WO1997016163A1 (en) * | 1995-10-31 | 1997-05-09 | The Procter & Gamble Company | Deodorant cosmetic stick composition |
US5837872A (en) * | 1995-11-13 | 1998-11-17 | Hoechst Celanese Corporation | Process for preparation of N-acyl-aminodiacids |
DE19643238A1 (en) * | 1996-10-19 | 1998-04-23 | Beiersdorf Ag | Antiperspirant and deodorant sticks with high water content |
WO1998028008A1 (en) * | 1996-12-20 | 1998-07-02 | The Procter & Gamble Company | Pharmaceutical compositions containing gellants in the form of alkyl amides of di- and tri-carboxylic acids |
WO1998027954A1 (en) * | 1996-12-20 | 1998-07-02 | The Procter & Gamble Company | Antiperspirant compositions containing gellants in the form of alkyl amides of di- and tri-carboxylic acids |
WO1998027948A1 (en) * | 1996-12-20 | 1998-07-02 | The Procter & Gamble Company | Gel compositions containing gellants in the form of alkyl amides of tri-carboxylic acids |
US5972319A (en) * | 1997-03-31 | 1999-10-26 | The Colgate-Palmolive Company | Antiperspirant stick with improved characteristics |
EP1009372B2 (en) † | 1997-09-04 | 2009-01-21 | Innoscent Ltd. | Method for the prevention and/or for the removal of body odors |
US6531119B1 (en) | 1998-03-05 | 2003-03-11 | Colgate-Palmolive Company | Compositions with low irritancy |
WO1999044576A1 (en) * | 1998-03-05 | 1999-09-10 | Colgate-Palmolive Company | Compositions with low irritancy |
WO2000061082A2 (en) * | 1999-04-12 | 2000-10-19 | Unilever Plc | Antiperspirant compositions |
WO2000061082A3 (en) * | 1999-04-12 | 2001-10-11 | Unilever Plc | Antiperspirant compositions |
US6287544B1 (en) | 1999-04-12 | 2001-09-11 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Antiperspirant compositions |
WO2000067713A1 (en) * | 1999-05-07 | 2000-11-16 | Henkel Kommanditgesellschaft Auf Aktien | Antiperspirant stick |
WO2001095870A2 (en) * | 2000-06-14 | 2001-12-20 | Colgate-Palmolive Company | Compositions with low irritancy |
WO2001095870A3 (en) * | 2000-06-14 | 2002-06-20 | Colgate Palmolive Co | Compositions with low irritancy |
WO2006012971A1 (en) | 2004-07-28 | 2006-02-09 | Henkel Kommanditgesellschaft Auf Aktien | Low-residue deodorant or antiperspirant stick based on an oil-in-water dispersion |
US8574559B2 (en) | 2005-05-11 | 2013-11-05 | Henkel Kommanditgesellschaft Auf Aktien | Low-residue deodorant or antiperspirant stick based on an oil-in-water dispersion/emulsion |
WO2010097205A3 (en) * | 2009-02-27 | 2011-11-10 | Beiersdorf Ag | Use of loaded surfactants for reducing textile spotting due to antiperspirants |
CN102395348A (en) * | 2009-02-27 | 2012-03-28 | 拜尔斯道夫股份有限公司 | Use of charged surfactants to reduce fabric staining by antiperspirants |
EP3111916A1 (en) * | 2009-02-27 | 2017-01-04 | Beiersdorf AG | Use of charged surfactants for reducing textile staining by antiperspirants |
EP3120828A1 (en) * | 2009-02-27 | 2017-01-25 | Beiersdorf AG | Use of charged surfactants for reducing textile staining by antiperspirants |
Also Published As
Publication number | Publication date |
---|---|
GR3024320T3 (en) | 1997-10-31 |
ATE156011T1 (en) | 1997-08-15 |
AU697551B2 (en) | 1998-10-08 |
ES2105704T3 (en) | 1997-10-16 |
FI955109A0 (en) | 1995-10-26 |
FI955109A (en) | 1995-10-26 |
CA2160364A1 (en) | 1994-11-10 |
AU6706494A (en) | 1994-11-21 |
DK0696188T3 (en) | 1997-09-01 |
DE69404646T2 (en) | 1998-03-05 |
EP0696188B1 (en) | 1997-07-30 |
US5733534A (en) | 1998-03-31 |
EP0696188A1 (en) | 1996-02-14 |
BR9406438A (en) | 1996-01-09 |
NO954258L (en) | 1995-12-22 |
JPH08509729A (en) | 1996-10-15 |
NO954258D0 (en) | 1995-10-25 |
DE69404646D1 (en) | 1997-09-04 |
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