EP1152742A1 - Compositions cosmetiques contenant des composes de vitamine b 3? - Google Patents

Compositions cosmetiques contenant des composes de vitamine b 3?

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Publication number
EP1152742A1
EP1152742A1 EP00908589A EP00908589A EP1152742A1 EP 1152742 A1 EP1152742 A1 EP 1152742A1 EP 00908589 A EP00908589 A EP 00908589A EP 00908589 A EP00908589 A EP 00908589A EP 1152742 A1 EP1152742 A1 EP 1152742A1
Authority
EP
European Patent Office
Prior art keywords
weight
vitamin
association
cosmetic composition
acid
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP00908589A
Other languages
German (de)
English (en)
Inventor
David Andrew Jakubovic
Michael Lee Vatter
Magda El-Nokaly
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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 Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP1152742A1 publication Critical patent/EP1152742A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • 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
    • A61K8/0295—Liquid crystals
    • 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
    • A61K8/67—Vitamins
    • A61K8/673—Vitamin B group
    • A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • 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
    • 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
    • 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
    • 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
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing

Definitions

  • the present invention relates to topical cosmetic comDOsitions composed p ⁇ ma ⁇ ly of lipophilic materials as the continuous phase and containing vitamin B 3 compounds
  • Niacin also known as vitamin B 3
  • the physiologically active form of niacin is niacmamide, also a member of the vitamin B 3 family of compounds Niacm and macmamide (nicotmic acid amide) function in the body as components of two coenzymes.
  • nicotmamide adenine dinucleotide (NAD) and nicotmamide adenme dinucleotide phosphate (NADP) Until recently, these vitamm B 3 compounds were used exclusively to treat niacin deficiency and pellegra.
  • vitamm B 3 compounds have also found use in the area of skm care actives
  • British Patent 1,370,236 describes compositions for skin lightening containing 0.5% to 10% niacm.
  • U S Patent 4,096,240 discloses the use of 0 1% to 10% niacmamide for skin lightening.
  • Vitamin B 3 compounds have also been found useful m regulating the texture of human skin. See PCT application WO 97-39733, to Oblong et al
  • the present inventors have found that incorporating solubilized vitamm B 3 compounds into water-in-oil cosmetic carriers improve the penetration of the vitamin B 3 compounds into the skm, thus, enhancing their skm regulating properties.
  • vitamin B 3 compounds are soluble m polar solvents, they can pose stability problems when formulated mto cosmetic compositions composed primarily of lipophilic materials (i.e., forming a lipophilic continuous phase)
  • the polar solvents e.g., polyhyd ⁇ c alcohols, water
  • lipophilic stick compositions e g., lipsticks
  • phase separation manifests itself as liquid beads along the surface of the stick composition This can negatively affect consumer acceptability.
  • compositions comprising vitamin B 3 compounds which provide improved skm penetration of the vitamm B 3 compound and provide good compositional stability.
  • the present inventors have found that the stability of cosmetic compositions compnsrng a vitamm B 3 compound, a polar solvent and a lipophilic continuous phase can be improved by incorporating surfactant or surfactant mixtures which has a Krafft point at or below about 20 C and form association structures such that the association structures thermodynamically bind the moisturizer/polar solvent and homogeneously absorb in the lipophilic matrix.
  • Another aspect of the present invention is to prov ide cosmetic compositions comp ⁇ smg solubilized vitamm B 3 compounds which provide improved skm penetration of the vitamin B 3 compound
  • a further aspect of the present invention is to provide cosmetic stick compositions compnsrng solubilized vitamin B 3 compounds
  • a still further aspect of the present invention is to provide cosmetic stick compositions comprising a lipophilic continuous phase and solubilized vitamin B 3 compounds stabilized by association structures
  • Still another aspect of the present invention is to provide cosmetic stick compositions which enhance the penetration of vitamin B 3 compounds into the skm
  • the present invention relates to topical cosmetic compositions useful for providing enhanced skm penetration of a vitamin B3 compound, comprising from about 0 01% to about 50%, by weight of the composition, of vitamm B 3 compound, from about 1% to about 90%, by weight of the composition, of emollient component comprising from 0 1% to about 100%, by weight of the emollient component, of an oil that is liquid at ambient temperature, from about 0 1% to about 80%, by weight of the composition, of a stabilizing system, comprising thereof, (1) from about 0 1% to about 90%, by weight of the stabilizing system, of a solidifying agent, and ( ⁇ ) from about 0 01% to about 30%, by weight of the stabilizing system, of a surfactant, wherein the surfactant has a Krafft point at or below about 20 Cand forms association structures, and from about 0 01% to about 90%, by weight of the composition, of a polar solvent
  • the term “cosmetics” includes make-up, foundation, and skm care products
  • make-up refers to products that leave color on the face, including foundation, blacks and browns, l e , mascara, eye liners, brow colors, eye shadows, blushers, lip colors, and so forth Sk care products are those used to treat or care for, or somehow moisturize, improve, or clean the skin
  • Products contemplated by the phrase “skin care products” include, but are not limited to, adhesives, bandages, toothpaste, anhydrous occlusive moisturizers, powder laundry detergent, fabric softener towels, occlusive drug delivery patches, antiperspirants, deodorants, nail polish, powders, tissues, wipes, solid emulsion compact, hair conditioners-anhydrous and the like
  • foundation refers to liquid, creme, mousse, pancake, concealer or like product created or remtroduced by cosmetic companies to even out the overall coloring of the skin Foundation is manufactured to work better over moisturized and/or
  • association structure refers to an aggregation of surfactant and/or polymer molecules such that they orient themselves forming a composite ordered structure
  • An association structure is also known in the art as a liquid crystalline phase
  • a requirement for the formation of a liquid crystal is the hydrocarbon portion of an amphiphihc molecule is transformed into a state with disorder as that in the liquid state
  • solid material refers to any solidifying ingredient capable of adsorbing the association structures
  • Solids include waxes, solid fats, clays, fillers, powders, uv-absorbers, suspending agents, waxy emulsifiers or pigments commonly used to thicken or solidify cosmetic compositions
  • color(s) or colorants includes pigments, dyes, colors, lakes, and pearl Colors are measured on an anhydrous weight basis
  • lecithin refers to a material which is a phosphatide
  • Naturally occurring or synthetic phosphatides can be used Phosphatidylcholine or lecithin is a glycerine esterified with a choline ester of phosphoric acid and two fatty acids, usually a long chain saturated or unsaturated fatty acid, having 16-20 carbons and up to 4 double bonds
  • Other phosphatides capable of forming association structures, preferably lamellar or hexagonal liquid crystals can be used m place of the lecithin or in combination with it
  • Other phosphatides are glycerol esters with two fatty acids as in the lecithm, but the choline is replaced by ethanolamine (a cephahn), or serine (a-aminopropanoic acid, phosphatidyl serine) or an mositol (phosphatidyl inositol)
  • surfactant refers to a low molecular weight or monomer non-polymeric organic compound amphiphihc in nature, i.e , it has hydrophihc and hydrophobic groups and exhibits a marked tendency to adsorb on a surface or interface and lower the surface tension
  • Surfactants or emulsifiers are divided into nomomc (no charge), anionic (negative charge), catiomc (positive charge) and amphote ⁇ c (both charges) based on whether or not they ionize in aqueous media
  • Surfactants are monomers and are derived from natural oils and fats and crude oils
  • surfactant refers to mixtures of surfactants as well as a single organic compound
  • polar solvent means a polar material capable of forming an association structure with a surfactant
  • polar solvents include glycerine, panthenol (preferably panthenol mixed with glycerine or alcohol), propylene glycol, butylene glycol, hexylene glycol, water, alcohols, alkanediols, polyethylene glycols. sorbitol, maltilal and mixtures thereof
  • composition can contain other ingredients which are compatible with the composition and which preferably do not substantially disrupt the association structures of the present inv ention
  • term encompasses the terms “consisting of and “consisting essentially of
  • ambient temperature refers to the temperature also known in the art as “room temperature” and typically means about 20°C Generally ambient temperature can range from about 18°C to about 27°C, preferably from about 20°C to about 25°C, depending on such variables as geographical location, l e sub-tropical ⁇ s temperate regions
  • compositions of the present invention comprise a safe and effective amount of a natural or synthetic vitamin B3 compound
  • the compositions of the present invention preferably comprise from above 0 01% to about 50%), more preferably from about 0 1% to about 30%, even more preferably 0 5% to about 20%, most preferably from about 1% to about 10% of the vitamin B3 compound
  • vitamin B3 compound means a compound having the formula
  • R is - CONH2 (1 e , macmamide), - COOH (1 e , nicotinic acid) or - CH2OH (1 e , nicotmyl alcohol), derivatives thereof, and salts of any of the foregoing
  • Exemplary derivatives of the foregoing vitamin B3 compounds mclude nicotinic acid esters, including non-vasodilatmg esters of nicotinic acid, nicotmyl ammo acids, nicotmyl alcohol esters of carboxylic acids, nicotmic acid N-oxide and macmamide N-oxide
  • Suitable esters of nicotinic acid include nicotinic acid esters of C1 -C22. preferably Ci -Ci g, more preferably C1 -C5 alcohols
  • the alcohols are suitably straight-chain or branched chain, cyclic or acyclic, saturated or unsaturated (including aromatic), and substituted or unsubstituted
  • the esters are preferably non-rubifacient
  • non-rubifacient means that the ester does not commonly yield a visible flushing response after application to the skin in the subject compositions (the majority of the general population would not experience a visible flushing response, although such compounds may cause vasodilation not visible to the naked eye)
  • a nicotinic acid material which is rubifacient at higher doses could be used at a lower dose to reduce the rubifacient effect
  • Non-rubifacient esters of nicotinic acid include tocopherol mcotmate and inositol hexani
  • Exemplary nicotmyl alcohol esters include mcotmyl alcohol esters of the carboxylic acids salicylic acid, acetic acid, glycohc acid, palmitic acid and the like
  • vitamin B3 compounds useful herein are 2-chloron ⁇ cot ⁇ nam ⁇ de, 6-am ⁇ non ⁇ cot ⁇ nam ⁇ de, 6-methylmcotmamide, n-methyl- nicotinamide, n,n-d ⁇ ethyln ⁇ cot ⁇ nam ⁇ de, n-(hydroxymethyl)-mcot ⁇ nam ⁇ de, qumohnic acid lmide, mcotinanilide, n-benzylnicotinamide, n-ethylnicotinamide, mfenazone, mcotinaldehyde, isomcotimc acid, methyl isomcotimc acid, thiomcotinamide, malamide, l-(3-pyndylmethyl) urea, 2-mercapton ⁇ cot ⁇ n ⁇ c acid,
  • vitamin B3 compounds are well known in the art and are commercially available from a number of sources, e g , the Sigma Chemical Company (St Louis, MO), ICN Biomedicals, Inc (Irvm, CA) and Ald ⁇ ch Chemical Company (Milwaukee, WI)
  • vitamin B3 compounds may be used herein Preferred vitamm B3 compounds are niacmamide and tocopherol nicotinate Niacmamide is more preferred
  • salts, derivatives, and salt derivatives of niacmamide are preferably those having substantially the same efficacy as macmamide in the methods of regulating skin condition described herein
  • Salts of the vitamin B3 compound are also useful herein
  • Nonlimitmg examples of salts of the vitamin B3 compound useful herein include organic or inorganic salts, such as inorganic salts with aniomc inorganic species (e g , chloride, bromide, iodide, carbonate, preferably chloride), and organic carboxylic acid salts (including mono-, di- and tn- Cl - C18 carboxylic acid salts, e g , acetate, sahcylate, glycolate, lactate, malate, citrate, preferably monocarboxyhc acid salts such as acetate)
  • aniomc inorganic species e g , chloride, bromide, iodide, carbonate, preferably chloride
  • organic carboxylic acid salts including mono-, di- and tn- Cl - C18 carboxylic acid salts, e g , acetate, sahcylate, glycolate, lactate
  • the ring nitrogen of the vitamin B3 compound is substantially chemically free (e g , unbound and/or unliindered), or alter deliveiy to the skm becomes substantially chemically free ("chemically free” is hereinafter alternatively refened to as "uncomplexed")
  • the vitamin B3 compound is essentially uncomplexed Therefore, if the composition contains the vitamin B3 compound in a salt or otherwise complexed form, such complex is preferably substantially reversible, more preferably essentially reversible, upon delivery of the composition to the skin For example, such complex should be substantially reversible at a pH of from about 5 0 to about 6 0 Such re
  • the vitamin B3 compound is substantially uncomplexed m the composition prior to delivery to the skin
  • Exemplary approaches to minimizing or preventing the formation of undesirable complexes include omission of materials which form substantially ineversible or other complexes with the vitamin B3 compound, pH adjustment, ionic strength adjustment, the use of surfactants, and formulating wherein the vitamin B3 compound and materials which complex therewith are in different phases Such approaches are well within the level of ordinary skill in the art
  • the vitamin B3 compound contains a limited amount of the salt form and is more preferably substantially free of salts of a vitamin B3 compound
  • the vitamin B3 compound contains a limited amount of the salt form and is more preferably substantially free of salts of a vitamin B3 compound
  • vitamin B3 compound contains less than about 50% of such salt, and is more preferably essentially free of the salt form
  • the vitamin B3 compound in the compositions hereof having a pH of from about 4 to about 7 typically contain less than about 50% of the salt form
  • the vitamin B3 compound may be included as the substantially pure material, or as an extract obtained by suitable physical and/or chemical isolation from natural (e g , plant) sources
  • the vitamin B3 compound is preferably substantially pure, more preferably essentially pure
  • Vitamin B 3 compounds which exist in crystalline form are particularly prefened for use herein Emollient Component
  • compositions of the present invention further comprise an emollient component, suitable for suspending or otherwise dispersing the crystalline vitamin B 3 compound therein
  • an emollient component suitable for suspending or otherwise dispersing the crystalline vitamin B 3 compound therein
  • Any emollient that is known or otherwise suitable for use in cosmetic applications, and which is also compatible with the vitamin B 3 compound in the composition, may be used in the composition of the present invention
  • Prefened emollients for use in the composition of the present invention are those materials refened to in the personal care arts as fats, oils, fatty alcohols, fatty acids, esters of fatty acids, and combinations thereof, and which aid application and adhesion, yield gloss and most importantly provide occlusive moistu ⁇ zation
  • Suitable emollients for use in compositions of the present inv ention are isosteanc acid derivatives, isopropyl palmitate, lanolin oil, dusopropyl dimerate, maleated soybean oil, octyl palmitate, isopropyl isostearate, cetyl lactate, cetyl ncmoleate, tocopheryl acetate, acetylated lanolin alcohol, cetyl acetate, phenyl tnmethicone, glyceryl oleate, tocopheryl hnoleate, wheat germ glyce ⁇ des, arachidyl propionate, mynstyl lactate, decyl oleate, propylene glycol ncmoleate, isopropyl lanolate, pentaerythntyl tetrastearate, neopentylglycol dicaprylate/dicaprate, hydrogenated coco-glyce
  • Suitable oils for use in compositions of the present invention include esters, tnglycendes, hydrocarbons and sihcones. These can be a single material or a mixture of one or more materials. They will normally comprise from 0 1% to about 100%, preferably from about 5% to about 90%, and most preferably from about 70% to about 90% of the emollient component.
  • Oils act as emollients and also impart viscosity, tackiness, and drag properties to cosmetic compositions such as lipsticks
  • suitable oils include capryhc tnglycendes; capnc tnglycende, isosteanc tnglycende; adipic tnglycende; propylene glycol mynstyl acetate; lanolm, lanolin oil; polybutene; isopropyl palmitate; isopropyl mynstate; isopropyl isostearate, diethyl sebacate; dusopropyl adipate; tocopheryl acetate; tocopheryl hnoleate; hexadecyl stearate; ethyl lactate; cetyl oleate; cetyl ncmoleate; oleyl alcohol; hexadecyl alcohol; octyl hydroxystearate; octyl do
  • the prefened oils for use herein are acetylglyce ⁇ des, octanoates, and decanoates of alcohols and polyalcohols, such as those of glycol and glycerol, the ⁇ cinoleates of alcohols and polyalcohols such as cetyl ncmoleate, PG-3 dnsostearate, polyglycerol ethers, polyglycerol esters, capryhc tnglycendes, capnc tnglycendes, isosteanc tnglycende, adipic tnglycende, phenyl tnmethicone, lanolin oil, polybutene, isopropyl palmitate, isopropyl isostearate, cetyl ncmoleate, octyl dodecanol, oleyl alcohol, hydrogenated vegetable oils, castor oil, modified lanolins, octyl palmitate, lanol
  • the oils used are selected such that the majority (at least about 75%, preferably at least about 80%) and most preferably at least about 99%) of the types of oils used have solubility parameters which do not differ by more than from about 1 to about 0 1, preferably from about 0.8 to about 0.1
  • the emollient component comprises from about 1% to about 90%, preferabh from about 10% to about 80%, more preferably from about 20% to about 70%, and most preferably from about 40%o to about 60%, of the cosmetic composition.
  • compositions of the present invention further comprise a stabilizing system
  • stabilizing system means a system which prevents the coalescence of polar solvent droplets and or, in the case of stick compositions, their migration to the surface of the stick a.
  • the cosmetic compositions of this invention can contain one or more materials, herein singly or collectively refened to as a "solidifying agent" , that are effective to solidify the particular liquid base materials to be used in a cosmetic composition (As used herem, the term “solidify” refers to the physical and/or chemical alteration of the liquid base material so as to form a solid or semi-solid at ambient conditions, 1 e .
  • the selection of the particular solidifying agent for use in the cosmetic compositions will depend upon the particular type of composition desired, 1 e , gel or wax-based, the desired rheology, the liquid base material used and the other materials to be used in the composition
  • the solidifying agent is preferably present at a concentration of from about 0 1% to about 90%, more preferably from about 1 to about 50%, even more preferably from about 5% to about 40%, most preferably from about 3%> to about 20%
  • the wax cosmetic stick embodiments of this invention preferably contain from about 5%> to about 50% (by weight) of a waxy solidifying agent
  • a waxy solidifying agent is meant a solidifying material having wax-like charactenstics
  • Such waxy materials may also serve as emollients
  • the waxy materials useful herein are the high melting point waxes, I e , having a melting point of from about 65°C to about 125°C, such as beeswax, spermaceti, carnauba, baysberry, candehlla, montan, ozokerite, ceresin, paraffin synthetic waxes such as Fisher-Tropsch waxes, microcrystallme wax, and mixtures thereof Ceresin, ozokerite, white beeswax, synthetic waxes, and mixtures thereof, are among the prefened high-meltmg point waxes useful herein Compositions containing waxes among those useful herein are disclosed in
  • biopolymers such as those described in European Application No 522624, to Dunphy et al . herein incorporated by reference in its entirety
  • the gel stick embodiments of this invention preferably contain from about 3% to about 30%, preferably from about 3% to about 10% (by weight), of a solidifying agent
  • a solidifying agent useful in the gel stick embodiments of this invention are, m general, surface-active compounds which form networks immobilizing or solidifying the liquid base materials into a gel
  • Such solidifying agents include soaps, such as the sodium and potassium salts of higher fatty acids, l e , acids having from 12 to 22 carbon atoms, amides of higher fatty acids, higher fatty acid amides of alkylolamines, dibenzaldehyde-monosorbitol acetals, alkali metal and alkaline earth metal salts of the acetates, propionates and lactates, waxes, such as candehlla and carnauba waxes, and mixtures thereof Among those solidifying agents pref
  • thickeners include, but are not limited to, naturally-occumng polymeric materials such as, locust bean gum, sodium alginate, sodium caseinate, egg albumin, gelatin agar, canageenin gum sodium alginate, xanthan gum, quince seed extract, tragacanth gum, starch, chemically modified starches and the like, semi-synthetic polymeric materials such as cellulose ethers (e.g.
  • polyvinylpynolidone polyvinylalcohol, guar gum, hydroxypropyl guar gum, soluble starch, cationic celluloses, cationic guars and the like and synthetic polymeric materials such as carboxyvinyl polymers, polyvinylpynolidone, polyvinyl alcohol polyacrylic acid polymers, polymethacrylic acid polymers, polyvinyl acetate polymers, polyvinyl chloride polymers, polyvmylidene chloride polymers and the like.
  • Inorganic thickeners may also be used such as aluminium silicates, such as, for example, bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • aluminium silicates such as, for example, bentonites
  • a mixture of polyethylene glycol and polyethylene glycol stearate or distearate such as, for example, bentonites
  • a mixture of polyethylene glycol and polyethylene glycol stearate or distearate such as, for example, bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • hydrophilic gelling agents such as the acrylic acid/ethyl acrylate copolymers and the carboxyvinyl polymers sold by the B.F. Goodrich Company under the trademark of Carbopol Registered TM resins.
  • These resins consist essentially of a colloidally water- soluble polyalkenyl polyether crosslinked polymer of acrylic acid crosslinked with from 0.75% to 2.00% of a crosslinking agent such as polyallyl sucrose or polyallyl pentaerythritol. Examples include Carbopol 934,Carbopol 940, Carbopol 950, Carbopol 980, Carbopol 951 and Carbopol 981.
  • Carbopol 934 is a water-soluble polymer of acrylic acid crosslinked with about 1% of a polyallyl ether of sucrose having an average of about 5.8 allyl groups for each sucrose molecule. Also suitable for use herein are carbomers sold under the Trade Name "Carbopol Ultrez 10, Carbopol ETD2020, Carbopol 1382, Carbopol 1342 and Pemulen TR-1 (CTFA Designation: Acrylates/10-30 Alkyl Acrylate Crosspolymer). Combination of the above polymers are also useful herein. Other gelling agents suitable for use herein include oleogels such as trihydroxystearin.
  • Hydrophobically modified celluloses are also suitable for use herein as solidifying agents. These celluloses are described in detail in U.S. Patents 4,228,277 and 5,104,646, both of which are herein incorporated by reference in their entirety.
  • the solidifying agent in combination with the emollient is believed to act as an occlusive on the skin by forming continuous or discontinuous bi-layer or multi-layer films on the skin.
  • occlusive means a preventing or obstructing something, in this case, preventing the removal of moisture (via evaporation) and the vitamin B 3 compound (via film binding) from the surface of the skin.
  • compositions of the present invention further comprise a surfactant
  • Surfactants suitable for use m the compositions of the present invention are those which can lorm association structures, preferably lamellar liquid crystals or reverse hexagonal, at ambient temperamre when mixed with a polar solvent Ambient temperature/room temperature as used herein typically means about 20°C Generally ambient temperamre can range from about 18°C to about 27°C, preferably from about 20°C to about 25°C, depending on such variables as geographical location, 1 e sub-tropical vs temperate regions One of ordinary skill in the art is able to determine if association structures form at ambient temperatures
  • the surfactants suitable for use generally have a Krafft point at or below about ambient temperature about 20°C or generally at or below about 18°C to about 27°C, preferably at or below from about 20°C to about 25°C
  • Krafft point is the melting point of the hydrocarbon chains of the surfactants It can also be expressed as the temperamre at which the solubility of an association colloid in water suddenly increases because critical micelle concentration is exceeded and micelles form.
  • Ekwall , P "Composition, Properties and Strucmre of Liquid Crystalline Phases in Systems of Amphiphi c Compounds" Advances m Liquid Crystals Vol I, Chapter I, p 81
  • the surfactant In preparing a sample combination of surfactant and polar solvent to demonstrate the ability to form association structures, the surfactant needs to be sufficiently soluble in the polar solvent such that an association strucmre can form at ambient temperamre
  • One of ordinary skill in the art is capable of determining compatible interactions
  • any surfactant which forms association structures at ambient temperature and is suitable for use m cosmetics is suitable for use herein
  • Surfactants suitable for use in cosmetics do not present dermatological or toxicological problems
  • Amonic surfactants, nomonic surfactants, cationic surfactants, amphote ⁇ c surfactants and mixtures thereof are suitable for use
  • amonic surfactants, nomonic surfactants, cationic surfactants, amphote ⁇ c surfactants and mixtures thereof having a Krafft point at or below about ambient temperamre are used More preferably, nomonic surfactants, cationic surfactants, amphote ⁇ c surfactants and mixtures thereof having a Krafft point at or below about ambient temperamre are used
  • association structures of the present invention are also useful in improving the skm penetration of the vitamin B 3 compound
  • the association structures are believed to act either as an occlusive or entrapping matrix on the skin by forming continuous or discontinuous bi-layer or multi-layer films on the skm
  • occlusive means a preventing or obstructing something, in this case preventing the removal of moisture (via evaporation) and the vitamin B 3 compound (via film binding) from the surface of the skin
  • entrapping matrix refers to unilamellar, multilamellar vesicles, cylindrical micelles, hexagonal liquid crystals, lamellar liquid crystals, or cubic phase liquid crystals capable of binding to the skin
  • the entrapping matrix entraps the vitamm B 3 compound and thus maintains skm contact with the vitamin B 3 compound
  • the association structures of the present invention are thermodynamically stable, it is believed that the entrapped or bound polar solvent is
  • the surfactants can be used at levels from about 4% to about 97%>, preferably from about 5% to about 95%), more preferably from about 20% to about 90% and most preferably from about 30% to about 70% of the association structure Polar Solvent
  • polar solvents refers to those solvents that contain hydroxyl and/or carbonyl groups and also have high dielectric constants and strong polarity
  • polar solvents include water, alcohols, such as ethanol, propyl alcohol, isopropyl alcohol, hexanol, and benzyl alcohol, polyols, such as propylene glycol, polypropylene glycol, butylene glycol, hexylene glycol, maltitol, sorbitol, and glycerine, panthenol dissolved in glycerine, flavor oils, and mixtures thereof Mixtures of these solvents can also be used
  • Prefened polar solvents are polyhyd ⁇ c alcohols and water Examples of prefened solvents include glycerine, panthenol m glycerine, glycols such as propylene glycol and butylene glycol, polyethylene glycols, water and mixture
  • the cosmetic compositions of the present invention will comprise from about 0 01% to about 90%, preferably from about 0 1% to about 60%, more preferably from about 1% to about 30% and most preferably from about 3% to about 18%) by weight of the composition of polar solvent
  • the solvents are used in relation to the association structures atlevels of from about 3%> to about 96%, preferably from about 5% to about 95%>, more preferably from about 10% to about 80% and most preferably from about 30% to about 70% by weight of the association structure
  • association structure I e
  • concentration at which such association structures occur is dependent upon a variety of factors, including the specific types of surfactant, solvent, temperamre, solubility of the surfactant in the solvent, and concentration of the surfactant in the earner
  • the purity of the surfactant affects the concentration level at which the association structures and particularly the prefened form of lamellar liquid crystals form
  • association strucmre particularly the prefened lamellar or hexagonal liquid crystalline state
  • mechanical agitation Mixing can be performed either by hand (I e , using hand utensils) or with mechamcal equipment useful for home, institutional, or industrial cosmetic preparation Extruders which provide a shearing operation w ith mixing can be used
  • the one -phase liquid crystal is most prefened It is prefened that a substantially two phase liquid crystal, one-phase liquid crystal or single phase liquid crystal component of (preferablv at least 90%) be utilized
  • Ultracentrifugation should be conducted using sufficiently high centrifugal forces (preferably within the range of from about 20,000 rpm to about 60,000 rpm for from about one hour to about sixteen hours utilizing a Beckman L8-80 centrifuge equipped with a SW6OT1 Rotor or by applying about 300,000*g for about one hour) to induce the formation of observable phase boundaries over a period of time Under these conditions a good separation of the individual phases is obtained The volume of each phase is determined by calibration of the centrifuge tube and the volume fraction of the individual phase thus calculated
  • compositions of the present invention may also include additional colloidal strucmres
  • additional colloidal strucmres Nonlimitmg examples of such colloid structures emulsions and gel networks
  • a detailed description of these and other useful colloid strucmres is found in Niels J Krog, Food Emulsifiers. pp 141- 188, Marcel Dekker, Inc , (1997), herein incorporated by reference in its entirety
  • Certain embodiments of the present invention may further comprise from about 0 1%> to about 90%>, preferably from about 1% to about 35%o, more preferably from about 1% to about 20% and most preferably from about 5% to about 15%, of color, on an anhydrous pigment weight basis
  • These are usually aluminum, barium or calcium salts or lakes
  • dyes are present at from about 0 1% to about 4% and pearls from 0% to about 20%
  • Pigments are typically dispersed m emollients for the good dispersion of the pigments when incorporated into the lip compositions, thus providing an even distribution of color Excellent dispersion of the pigment can be achieved by utilizing association structures, preferably lamellar liquid crystals, as a means of incorporating the color/pigments into the cosmetic compositions of the present
  • a prefened method of incorporating dry pigments comprises the steps of
  • a surfactant selected from the group consisting of amphote ⁇ c, cationic, amonic and nomonic surfactants having a Krafft point at or below about ambient temperamre and mixtures thereof, and
  • the prefened method of incorporating the dry pigments is to slurry them in one or more of the liquid emollient ingredients
  • Colors/pigments suitable for use herein are all inorganic and organic colors/pigments suitable for use in lipstick compositions
  • Lakes are either a pigment that is extended or reduced with a solid diluent or an organic pigment that is prepared by the precipitation of a water-soluble dye on an adsorptive surface, which usually is aluminum hydrate
  • a water-soluble dye on an adsorptive surface
  • a lake also forms from precipitation of an insoluble salt from an acid or basic dye
  • Lakes suitable for use in the present invention include Red 3 Aluminum Lake, Red 21 Aluminum Lake, Red 27 Aluminum Lake, Red 28 Aluminum Lake, Red 33 Aluminum Lake, Yellow 5 Aluminum Lake, Yellow 6 Aluminum Lake, Yellow 10 Aluminum Lake, Orange 5 Aluminum Lake and Blue 1 Aluminum Lake, Red 6 Barium Lake, Red 7 Calcium Lake
  • colors and pigments can also be included in the lipsticks, such as dyes and pearls, titanium oxides, Red 6, Red 21, Brown, Russet and Sienna dyes, chalk, talc, iron oxides and titanated micas
  • the color component is water-insoluble particulate solids having an average primary particle size diameter of less than about 5 microns, preferably 2 microns, more preferably 1 microns
  • Dispersants may also be used in conjunction with the colors and pigments of the present invention
  • suitable dispersants include, but are not limited to, those described in U S Patent 5,688,493, herein incorporated by reference in its entirety.
  • compositions of the present invention include the flavor oils,, fat soluble vitamins such as vitamin A and E, esters of vitamin A (e g , acetate, propionate, or palmitate) and of vitamin E (e g , acetate or sorbate), sunscreens such as octyl methoxycinnamate, butyl methoxydibenzoylmethane, titanium dioxide and zinc oxide, germicides such as t ⁇ closan anti-mflammatory agents -uch as hydrocortisone hpid matenals such as ceramides and hposomes and skm care actives
  • the cosmetic compositions can comprise ingredients conventionally employed in cosmetic compositions such as mascara, foundation or hpcare products. This includes skm care active mgredients such as pharmaceutically activ e ingredients
  • Skm care actives ingredients in both water soluble and water insoluble forms can be added to the cosmetic compositions of the present invention.
  • these include, but are not limited to vitamm C and its derivatives (e.g , ascorbyl palmitate, ascorbyl phosphate and its salts such as magnesium or sodium), vitamin D, panthenol, retmoic acid, zinc oxide, beta-glycyerhetic acid, chamomile oil; ginko biloba extract, pyroglutamic acid, salts or esters, sodium hyaluronate, 2-hydroxyoctano ⁇ c acid; sulfur; salicylic acid; carboxymethyl cysteme, and mixtures thereof.
  • vitamm C and its derivatives e.g , ascorbyl palmitate, ascorbyl phosphate and its salts such as magnesium or sodium
  • vitamin D e.g , ascorbyl palmitate, ascorbyl phosphate and its salts such as magnesium or sodium
  • vitamin D e.g
  • additives both fat soluble and water soluble, will normally be present in amounts of less than about 10% by weight, and generally m the range of about 0.01% to about 5%, preferably from about 0.01% to about 3%, most preferably from about 0.1% to about 1%, by weight
  • Flavor oils such as peppermint oil, orange oil, citrus oil, wintergreen oil can be used along with an alcohol or glycerine Flavor oils are usually mixed m a solvent such as ethanol to dilute the flavor.
  • the flavor oils useful herein can be derived from natural sources or be synthetically prepared Generally flavor oils are mixtures of ketones, alcohols, fatty acids, esters and terpenes
  • the term "flavor oil” is generally recognized in the art to be a liquid which is derived from botanical sources, i.e leaves, bark, or skm of fruits or vegetables, and which are usually insoluble in water.
  • the level of flavor oil used can range from 0% to about 5%, preferable from 0%> to about 1%
  • moisturizers include pyrrohdone carboxylic acid, sodium lactate or lactic acid, urea, guamdine, glyce ⁇ c acid and its salts (e.g., calcium salt), petrolatum, collagen, ⁇ -hydroxy propylglyceryl ether, ⁇ -hydroxy acids (e.g., ethylglycohc acid, leucic acid, mandehc acid, glycohc acid), glucosamines, and elastin fibers, D- panthenol, allantom and hyaluronic acid and chondroitm sulfate.
  • suitable moisturizers can be found in Cosmetic Bench Reference, p. 1.30-1.32 ( 1996), herein incorporated by reference.
  • emulsifiers commonly known as coupling agents can also be used herein.
  • the overall concentration of the emulsifier can be from 0%> to about 20%) of the formulation, preferably from 0% to about 15% and most preferably from about 1 % to about 10%.
  • suitable emulsifiers can be found in U.S. Patent 5,085,856 to Dunphy et al.; Japanese Patent Publication Sho 61-83110; European Patent Application EP 522624 to Dunphy et al., U.S patent 5,688,831 to El-Nokaly et al.; and Examples of suitable moistures can be found m Cosmetic Bench Reference, pp 1.22, 1.24-1 26 (1996), all of which are herein incorporated by reference in their entirety
  • a prefened embodiment of the present invention preferably comprises, a ) from about 1% to about 10%, niacmamide, b ) from about 0 1% to about 50%), preferably from about 0 1% to about 15%>, polar solvent c.) from about 0 1% to about 20%, surfactants of the cosmetic composition and d) from about 0 1% to about 50% of an oil that is liquid at ambient temperamre
  • the surfactants are preferably a mixture wherein from about 50% to about 75% of the mixture is made up of surfactants which have a Krafft point of at or below about ambient temperamre and form association strucmres at ambient temperamre and from about 25% to about 50% of the mixture is made up of surfactants which are coupling agents
  • Another prefened mixture of surfactants which can form association strucmres and surfactants which act as coupling agent is lecithin, PG-3 dnsosterate, sorbitan monooleate, cholesterol 12 hydroxy
  • a prefened optional component is ethyl cellulose (Ethocel)
  • Ethyl cellulose generally is prefened for use at levels of about 5% and more preferably 1%
  • silica Silica is generally prefened for use at levels of from about 1% and about 5%
  • Hypoallergemc compositions can be made from the liquid crystal, wax, oil and colors herein These lipsticks should not contain fragrances, flavor oils, lanolin, sunscreens, particularly PABA, or other sensitizers or potential sensitizers and lmtants
  • compositions of the present invention can also be made into long lasting or non- transferable cosmetic compositions Detailed discussions of such lipsticks are found in Japanese Patent Publication Hei No 6-199630 and European Patent Application 748622, both of which are herein incorporated by reference in their entirety
  • compositions of the present invention can be found in PCT application WO 97/39733, to Oblong et al
  • the present invention encompasses methods of preparing stable cosmetic compositions comprising vitamin B 3 compounds
  • Conventional formulation and mixing techniques can be used and generally comprise dissolving vitamin B 3 compounds m a polar solvent and adding the solution to a hydrophobic base composed of an emollient component, and a stabilizing system comprising a solidifying agent and a surfactant, yielding a cosmetic composition comprised as described above
  • this invention provides a method of improving the skin penetration of vitamin B 3 compounds, especially in lips and improving product stability
  • Conventional formulation and mixing techniques are described in detail in Harry's Cosmeticology, pp 119-141 and 314-354 (J B Wilkinson and R J Moore 7 th ed 1982) and Cosmetics Science and Technology, pp 1-104 and 307-422 (M S Balsam and E Sagarin 2 nd ed 1972), both of which are herein incorporated by reference in their entirety
  • the cosmetic compositions of the present invention are ideally suited for use in treating the skm and lips, especially in the form of a lipstick or lip balm for applying to the lips a permanent or semipermanent color, ideally with a gloss or luster finish
  • the cosmetic compositions can also be used in treating the skin and/or lips with a skin care agent for protection against exposure to adverse weather, including the wind and the rain, dry and or hot environments, environmental pollutants (e g , ozone, smoke, and the like), or exposure to excessive doses of sunlight
  • the compositions are also useful in providing sun protection, moisturizing and or conditioning for the hair and skm, improved skin feel, regulating skin texture, reducing fine lines and wrinkles, reducing oily shme on hair or skm, skm lightening and reducing skm or hair odor
  • the cosmetic composition can, accordingly, be applied to the skin and/or lips in the traditional manner using a convenient holder or applicator to provide a decorative and/or protective film thereto
  • compositions can be prepared by conventional formulation and mixing techniques Component amounts are listed as weight percents and exclude mmor materials such as diluents, filler, and so forth.
  • the listed formulations therefore, comprise the listed components and any minor materials associated with such components
  • the above ingredients are added to a stainless steel vessel equipped with a heating source
  • the ingredients are heated to about 85°C and mixed until a homogeneous This mixture is then poured into a mold and cooled to room temperamre.
  • the lipstick is applied to the lips to provide color, moisturization and improved skin penetration of the niacinamide.
  • the ingredients for the Association Structure Phase are mixed until association structures are formed. Once the association structures are formed, the pigments are added and milled on a three roll mill. The mixture is then mixed with the other ingredients and mixed until a homogeneous mixture. (Or, alternatively, the above components are added and mixed together at the same time.) This mixture is heated to 85°C and then poured into a mold at room temperature.
  • the lipstick is applied to the lips to provide color, moisturization and improved skin penetration of the niacinamide.
  • composition is prepared and used as in Example II.
  • composition is prepared as in Example II.
  • An antiperspirant composition comprised as above, is applied to the underarm area of a human subject, and reduces the perspiration m the applied area and improves odor in this area
  • An antiperspirant composition compnsed as above, is applied to the underarm area of a human subject, and reduces the perspiration in the applied area and improves odor in this area.
  • Glycerin 3.0 iso-eicosane 4 13.0
  • the cyclomethicone dimethicone, iso-eicosane and perfume are added to a stainless steel mixing vessel.
  • the Cab-O-Sil is then added, followed by the Microthene and Natrosol and, finally, the antiperspirant active.
  • the composition is thoroughly stirred after addition of each particulate material.
  • the composition is then milled, using a Black & Decker Die Grinder (Model 4420, type 4) with a 6.35 cm diameter Cowles dispersing blade at approximately 6,000 rpm, for approximately 5 minutes.
  • the penetration force value of the milled composition is approximately 300 grams at 25o C. and 50% relative humidity.
  • An antiperspirant cream formulation is applied to the underarm area of a human subject, and reduces the perspiration in the applied area and improves odor in this area.
  • Emerest 2400 available form Henkel/Emery -
  • Centrolex F available from Central Soya, Inc. -
  • the waxes and fats are mixed in a vessel equipped with a heating source.
  • the waxes and fats are heated and mixed at low speed using a conventional blender to liquify the mixture.
  • the mixing is continued until the mixture is homogeneous.
  • To the homogenous mixture is added the pigments.
  • the mixing rate is increased to high and the pigments are mixed into the mixture for about 30-35 minutes until uniformly dispersed.
  • the mixing is continued while adding emulsifiers.
  • a second vessel equipped with a heating source is added water followed by the niacinamide, lecithin and any other water-dispersable components.
  • the mixture is heated and mixed to a temperature of from about 80-95°C. Additional water is added as necessary to account for water loss.
  • aqueous and lipophilic mixtures are combined and mixed using a dispersator type mixer. Mixing is continued until the mixture cools to a temperature of from about 65-70°C. Preservatives are added with mixing, allowing the mixture to cool further to 45-47°C. Any remaining components are added with mixing. The combined mixture is cooled to a temperamre above the solidification point and is then poured into suitable containers.
  • the mascara composition is applied to the lashes and/or eyebrows to provide softening, moisturization and conditioning.
  • Emerest 2400 available form Henkel/Emery -
  • the mascara is prepared and used as in Example VIII.
  • the lipstick is applied to the lips to provide color, moisturization and improved penetration of the niacinamide
  • EA-209 Ethylene Acrylic Acid Copolymer (EA-209) 3 200
  • the ingredients of Part C are combined and milled using a Sih erson L4R at high speed (preferably about 9000-10000 ⁇ m) with 1" disintegrating screen for at least 'A hour or until the mixture is uniform
  • the ingredients of Part A are combined and mix using a Silverson L4R at about 3000 ⁇ m with 2" emulsor screen.
  • the ingredients of Part B are combined separately and, before the propylparaben is completely dissolved, Part B is added to Part A using a Silverson L4R at about 3000-4000 m with 2" emulsor screen.
  • Part C is slowly added the Parts A and B with mixing using a Silverson L4R at about 6000 ⁇ m with 2" emulsor screen. Mixing is continued until mixmre is uniform.
  • Part D is added maintaining adequate turnover (i.e., using a blending speed of about 6000-8000 ⁇ m) and then heated to a temperamre of about 80°C. The oxokerite wax is added to the heated mixmre with mixing until mixture is uniform.
  • the mixmre is deaerated by vacuum and poured into the appropriate mold. The mixture is cooled to ambient temperamre and inco ⁇ orated into the appropriate package.
  • the solid compact emulsion is applied to the skin to reduce fine lines and texture of skin as well as reduce oily shine.
  • Part A An admixture (Part A) is prepared by combining in a suitable vessel the following ingredients:
  • the admixture is mixed using conventional mixing techniques until the MQ Resin is dissolved. Processing:
  • Part B An admixture (Part B) is prepared by combining in a suitable vessel the following ingredients:
  • a cosmetic emulsion composition containing Part A and Part B is prepared by combining the following ingredients:
  • the admixture of Part A along with the pigments, propylparaben and PM99A are combined and mixed using a Ultra Tunax T25 homogemzer at about 8,000 ⁇ ms for about 10 mmutes or until the cosmetic mixture is uniform (taking care not to ignite the PM99A)
  • the Bentone ISD added to the cosmetic mixmre with mixing at about 8, 000 ⁇ ms until the mixmre is uniform
  • the water, niacinamide and lecithin are mixed together in a separate vessel to form association strucmres and then added to the cosmetic mixmre with stimng
  • the Lapomte XLS is added to the mixmre and mixing using a Ross homogemzer at about 3,500 ⁇ ms until uniform
  • the admixture of Part B is added to the cosmetic mixmre and mixed initially at high shear, preferably 1600 ⁇ ms , to facilitate dispersion using an IKA mixer. Once sufficient dispersion is achieved
  • the cosmetic emulsion composition is applied to impart color to the skin, improve skm texture and provide improved skm penetration of the niacinamide.

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Abstract

La présente invention concerne des compositions cosmétiques topiques essentiellement constituées de substances lipophiles pour la phase continue, et qui contiennent des composés de vitamine B3. Ces compositions sont utilisées pour améliorer la stabilité et la pénétration dans la peau de compositions contenant des composés de vitamine B3.
EP00908589A 1999-02-12 2000-02-10 Compositions cosmetiques contenant des composes de vitamine b 3? Withdrawn EP1152742A1 (fr)

Applications Claiming Priority (3)

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US12004699P 1999-02-12 1999-02-12
US120046P 1999-02-12
PCT/US2000/003463 WO2000047182A1 (fr) 1999-02-12 2000-02-10 Compositions cosmetiques contenant des composes de vitamine b¿3?

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EP1152742A1 true EP1152742A1 (fr) 2001-11-14

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JP (1) JP2002536396A (fr)
KR (1) KR20010102077A (fr)
CN (1) CN1344151A (fr)
AU (1) AU769065B2 (fr)
CA (1) CA2360216A1 (fr)
CZ (1) CZ20012926A3 (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1792630A1 (fr) 2005-12-02 2007-06-06 The Procter & Gamble Company Conjugués d'acides aminés et de la vitamine B3 pour l'administration transcutanée de la vitamine B3

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001213723A (ja) * 2000-01-31 2001-08-07 Tokiwa Corp 棒状化粧料
US6878382B2 (en) 2000-09-26 2005-04-12 The Procter & Gamble Company Personal care composition comprising hydrophobic gel
KR20030036817A (ko) * 2000-09-26 2003-05-09 더 프록터 앤드 갬블 캄파니 소수성 젤을 함유하는 퍼스널 케어 조성물
US7033579B1 (en) 2001-03-05 2006-04-25 The Procter & Gamble Company Anhydrous antiperspirant and deodorant compositions containing solid vitamin B3 particulates and glycerin
US6383476B1 (en) 2001-03-05 2002-05-07 The Procter & Gamble Company Anhydrous antiperspirant and deodorant compositions containing a solid, water-soluble, skin active agent
US6403071B1 (en) * 2001-03-05 2002-06-11 The Procter & Gamble Company Anhydrous antiperspirant and deodorant compositions containing solid d-pantothenate salts
GB0109143D0 (en) * 2001-04-11 2001-05-30 Unilever Plc Antiperspirant compositions comprising microemulsions
US7255869B2 (en) * 2001-10-30 2007-08-14 The Procter & Gamble Company Anhydrous cosmetic compositions containing polyols
KR100770113B1 (ko) * 2001-11-02 2007-10-24 주식회사 엘지생활건강 니코틴아미드 함유 나노에멀젼 및 이를 포함하는 화장료
US20040191279A1 (en) * 2003-03-28 2004-09-30 Klofta Thomas James Tacky skin care compositions and articles having tacky skin care compositions disposed thereon
US20050238680A1 (en) * 2004-04-21 2005-10-27 Qing Stella Personal care compositions that deposit hydrophilic benefit agents
EP2071976A3 (fr) * 2007-12-20 2009-07-22 Unilever PLC Produits cosmétiques comprenant des ingredients labiles
EP2071975A3 (fr) * 2007-12-20 2009-07-15 Unilever PLC Produits anti-transpirants ou déodorants comprenant des ingredients labiles et des pigments
US9445975B2 (en) 2008-10-03 2016-09-20 Access Business Group International, Llc Composition and method for preparing stable unilamellar liposomal suspension
WO2010145909A1 (fr) * 2009-06-16 2010-12-23 Unilever Plc Utilisation d'un antitranspirant
FR2975005B1 (fr) * 2011-05-13 2016-03-11 Oreal Composition cosmetique de revetement des fibres keratiniques du type emulsion, procede de revetement des fibres keratiniques et utilisation
US9597271B2 (en) 2013-10-24 2017-03-21 The Procter & Gamble Company Cosmetic compositions and methods
FR3053333B1 (fr) * 2016-06-30 2018-07-27 L'oreal Melange liquide contenant du 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one et un com-pose de niacinamide, et composition cosmetique le contenant
JP2018087149A (ja) * 2016-11-28 2018-06-07 ロレアル ナノ又はマイクロエマルションの形態の組成物
EP3558214A1 (fr) * 2016-12-20 2019-10-30 Chanel Parfums Beauté Composition cosmétique solide à effet hydratant
JP6682495B2 (ja) * 2017-12-18 2020-04-15 三菱鉛筆株式会社 固形化粧料
JP2023546979A (ja) * 2020-10-30 2023-11-08 ロレアル スキンケアのための組成物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU658681B2 (en) * 1991-10-23 1995-04-27 Block Drug Company Inc., The Penetration enhancement of topically applied formulations
WO1995011000A1 (fr) * 1993-10-18 1995-04-27 The Procter & Gamble Company Rouges a levres non exsudants
US5496827A (en) * 1994-07-15 1996-03-05 Patrick; Jay Compositions for the transdermal delivery of nutrients
US5968528A (en) * 1997-05-23 1999-10-19 The Procter & Gamble Company Skin care compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0047182A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1792630A1 (fr) 2005-12-02 2007-06-06 The Procter & Gamble Company Conjugués d'acides aminés et de la vitamine B3 pour l'administration transcutanée de la vitamine B3

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CA2360216A1 (fr) 2000-08-17
JP2002536396A (ja) 2002-10-29
CN1344151A (zh) 2002-04-10
AU769065B2 (en) 2004-01-15
KR20010102077A (ko) 2001-11-15

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