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WO1999047115A1 - Compositions pour soins de la peau - Google Patents

Compositions pour soins de la peau Download PDF

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Publication number
WO1999047115A1
WO1999047115A1 PCT/US1999/005410 US9905410W WO9947115A1 WO 1999047115 A1 WO1999047115 A1 WO 1999047115A1 US 9905410 W US9905410 W US 9905410W WO 9947115 A1 WO9947115 A1 WO 9947115A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
vitamin
skin
compound
aqueous phase
Prior art date
Application number
PCT/US1999/005410
Other languages
English (en)
Inventor
Brent William Mason
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AU30825/99A priority Critical patent/AU3082599A/en
Publication of WO1999047115A1 publication Critical patent/WO1999047115A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—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

Definitions

  • Niacin also known as vitamin B 3
  • the physiologically active form of niacin is niacinamide.
  • Niacin and niacinamide (nicotinic acid amide) function in the body as components of two coenzymes: nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP).
  • NAD nicotinamide adenine dinucleotide
  • NADP nicotinamide adenine dinucleotide phosphate
  • vitamin B 3 compounds act by retarding melanin dispersion or distribution into the epidermis.
  • vitamin B 3 compounds as skin care actives, however, concerns the stability of such compounds in skin care formulations.
  • skin care compositions containing high concentrations of a non-aqueous phase in addition to vitamin B 3 compounds tend to leave a visible white residue on the skin upon application. This residue apparently results from a "salting out" of the vitamin B 3 compound.
  • incorporation of a neutralizing agent along with the vitamin B compound in compositions containing high amounts of a non-aqueous phase provide compositions having improved aesthetics and reduced visible white residue after application.
  • the present invention relates to skin care compositions having improved stability, comprising:
  • the present invention further relates to methods of using the skin care compositions.
  • compositions of the present invention can comprise, consist of, or consist essentially of the essential elements and limitations of the invention described herein, as well any of the additional or optional ingredients, components, or limitations described herein.
  • compositions of the present invention comprise a safe and effective amount of a natural or synthetic vitamin B3 compound.
  • present invention preferably comprise from above 0.1% to about 50%, more preferably from about 1% to about 30%, even more preferably from about 5% to about 20% of the vitamin B3 compound.
  • vitamin B3 compound means a compound having the formula:
  • R is - CO H2 (i.e., niacinamide), - COOH (i.e., nicotinic acid) or - CH2OH
  • nicotinyl alcohol i.e., nicotinyl alcohol
  • derivatives thereof i.e., nicotinyl alcohol
  • salts of any of the foregoing i.e., nicotinyl alcohol
  • Exemplary derivatives of the foregoing vitamin B3 compounds include nicotinic acid esters, including non-vasodilating esters of nicotinic acid, nicotinyl amino acids, nicotinyl alcohol esters of carboxylic acids, nicotinic acid N-oxide and niacinamide N-oxide.
  • Suitable esters of nicotinic acid include nicotinic acid esters of C1-C22, preferably Cj-C ⁇ , more preferably Cj-Cg 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).
  • Non-rubifacient esters of nicotinic acid include tocopherol nicotinate and inositol hexanicotinate; tocopherol nicotinate is preferred.
  • Other derivatives of the vitamin B3 compound are derivatives of niacinamide resulting from substitution of one or more of the amide group hydrogens.
  • Nonlimiting examples of derivatives of niacinamide useful herein include nicotinyl amino acids, derived, for example, from the reaction of an activated nicotinic acid compound (e.g., nicotinic acid azide or nicotinyl chloride) with an amino acid, and nicotinyl alcohol esters of organic carboxylic acids (e.g., Cl - C18).
  • an activated nicotinic acid compound e.g., nicotinic acid azide or nicotinyl chloride
  • nicotinyl alcohol esters of organic carboxylic acids e.g., Cl - C18.
  • Specific examples of such derivatives include nicotinuric acid and nicotinyl hydroxamic acid, which have the following chemical structures: nicotinuric acid: o o
  • nicotinyl alcohol esters include nicotinyl alcohol esters of the carboxylic acids salicylic acid, acetic acid, glycolic acid, palmitic acid and the like.
  • vitamin B3 compounds useful herein are 2- chloronicotinamide, 6-aminonicotinamide, 6-methylnicotinamide, n-methyl- nicotinamide, n,n-diethylnicotinamide, n-(hydroxymethyl)-nicotinamide, quinolinic acid imide, nicotinanilide, n-benzylnicotinamide, n-ethylnicotinamide, nifenazone, nicotinaldehyde, isonicotinic acid, methyl isonicotinic acid, thionicotinamide, nialamide, l-(3-pyridylmethyl) urea, 2-mercaptonicotinic acid, nicomol, and niaprazine.
  • 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. (Irvin, CA) and Aldrich Chemical Company (Milwaukee, WI).
  • vitamin B3 compounds may be used herein.
  • Preferred vitamin B3 compounds may be used herein.
  • B3 compounds are niacinamide and tocopherol nicotinate. Niacinamide is more preferred. 5
  • salts, derivatives, and salt derivatives of niacinamide are preferably those having substantially the same efficacy as niacinamide in the methods of regulating skin condition described herein.
  • Salts of the vitamin B3 compound are also useful herein.
  • Nonlimiting examples of salts of the vitamin B3 compound useful herein include organic or inorganic salts, such as inorganic salts with anionic inorganic species (e.g., chloride, bromide, iodide, carbonate, preferably chloride), and organic carboxylic acid salts (including mono-, di- and tri- Cl - C18 carboxylic acid salts, e.g., acetate, salicylate, glycolate, lactate, malate, citrate, preferably monocarboxylic acid salts such as acetate).
  • anionic inorganic species e.g., chloride, bromide, iodide, carbonate, preferably chloride
  • organic carboxylic acid salts including mono-, di- and tri- Cl - C18 carboxylic acid salts, e.g., acetate, salicylate, glycolate, lactate, malate, citrate, preferably monocarboxylic acid salts such
  • Wenner "The Reaction of L- Ascorbic and D-Isoascorbic Acid with Nicotinic Acid and Its Amide", J. Organic Chemistry, VOL. 14, 22-26 (1949), which is incorporated herein by reference. Wenner describes the synthesis of the ascorbic acid salt of niacinamide.
  • the ring nitrogen of the vitamin B3 compound is substantially chemically free (e.g., unbound and/or unhindered), or after delivery to the skin becomes substantially chemically free ("chemically free” is hereinafter alternatively referred to as "uncomplexed”). More preferably, the vitamin B3 compound is essentially uncomplexed.
  • 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.
  • such complex should be substantially reversible at a pH of from about 5.0 to about 6.0.
  • Such reversibility can be readily determined by one having ordinary skill in the art.
  • the vitamin B3 compound is substantially uncomplexed in 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 irreversible 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 6
  • 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 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 B3 compounds which exist in crystalline form are particularly preferred for use herein.
  • Carrier System
  • compositions of the present invention comprise an improved carrier system.
  • the improved carrier is a dermatologically acceptable carrier.
  • dermatologically acceptable carrier means that the carrier is suitable for topical application to the skin, has good aesthetic properties, is compatible with the actives of the present invention and any other components, and will not cause any untoward safety or toxicity concerns.
  • compositions containing vitamin B 3 compounds and high concentrations of a non-aqueous phase tend to leave a visible white residue on the skin upon application. This may be the result of recrystallization of the vitamin B 3 compound due to the increased concentration of the non-aqueous phase in these formulas.
  • non-aqueous phase or “oil phase,” as used herein, means that only an oil or oil like substance is present or, indeed, that the phase contains any hydrocarbon material commonly known by the term “oil.”
  • water phase or “aqueous phase,” as used herein, means the water portion of the carrier. It should be understood, however, that the term “aqueous phase” should not be taken to mean that water is present to the exclusion of all other ingredients in that phase.
  • high non-aqueous phase means a non-aqueous phase concentration in the carrier of at least about 8%, preferably from about 8% to about 30%, more preferably from about 15% to about 20%, by weight of the total composition.
  • the improved carrier system of the present invention facilitates the dissolution of vitamin B 3 compounds in the non- aqueous phase of the compositions and, additionally, retards the precipitation of the vitamin B 3 compounds in such compositions over time.
  • the ratio of the non-aqueous phase to the aqueous phase is preferably from about 92:8 to about 70:30, preferably from about 90:10 to about 75:25, and more preferably from about 85: 15 to about 80:20.
  • An essential ingredient of the improved carrier system is a neutralizing agent sufficient to neutralize the present compositions to a pH of from about 6 to about 10, preferably from about 7 to about 10, and more preferably from about 8 to about 10.
  • the neutralizing agent of the present invention is preferably a weak base having a pKa from about 6 to about 9.
  • neutralizing agents examples include alkanolamines such as monoethanolamine, diethanolamine and triethanolamine; alkylamines such as triethylamine, diethylamine, monoethylamine, diisopropylamine, trimethylamine and diisobutylamine, alkylalkanolamines such as dimethylaminoethanol; alicyclic amines such as cyclohexylamine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and ammonia. Mixtures of the above neutralizing agents may also be used.
  • Preferred neutralizing agents are alkanolamines.
  • the improved carrier system of the present invention may optionally contain a thickener.
  • suitable thickeners include naturally-occurring polymeric materials such as sodium alginate, xanthan gum, quince seed extract, tragacanth gum, starch and the like, semi-synthetic polymeric materials such as cellulose ethers (e.g.
  • hydroxyethyl cellulose methyl cellulose, carboxymethyl cellulose, hydroxy propylmethyl cellulose
  • polyvinylpyrrolidone polyvinylalcohol
  • guar gum hydroxypropyl guar gum
  • soluble starch cationic celluloses, cationic guars and the like and synthetic polymeric materials such as carboxyvinyl polymers, polyvinylpyrrolidone, polyvinyl alcohol polyacrylic acid polymers, polymethacrylic 8
  • 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.
  • Preferred thickeners are those having a high salt tolerance.
  • the term "high salt tolerance" as used herein means that the thickener maintains its function in the presence of aqueous salt solutions having a salt concentration of at least 0.5%.
  • Particularly preferred for use herein are hydroxyethyl cellulose.
  • the thickener is preferably present at a concentration of from about 0.1 to about 2.0%, preferably from about 0.1 to about 1.0%, and more preferably from about 0.1 to about 0.4%. Mixtures above the above polymers may also be used.
  • Humectants may also be incorporated into the improved carrier system. Suitable humectants include hexylene glycol, PEG-7 glyceryl cocoate, propylene glycol or sorbitol, sodium pyrrolidonecarboxylic acid, glycerin (glycerol), polyethylene glycol wax, D-panthenol, hyaluronic acid, glucosides (e.g., Glucam E10 and E20 available from Amerchol Corporation), lactamide monoethanolamine, and acetamide monoethanolamine and mixtures thereof .
  • Preferred for use herein is glycerin.
  • the humectant is preferably present at a concentration of less than about 10%, preferably from about 2% to about 7%, and more preferably from about 3% to about 5%. Mixtures of the above humectants may also be used.
  • the carrier can be in a wide variety of forms.
  • emulsion carriers including, but not limited to, oil-in-water, water-in-oil, water-in-oil-in-water, and oil- in-water-in-silicone emulsions, are useful herein. These emulsions can cover a broad range of viscosities, e.g, from about 100 cps to about 200,000 cps. These emulsions can also be delivered in the form of sprays using either mechanical pump containers or pressurized aerosol containers using conventional propellants. These carriers can also be delivered in the form of a mousse.
  • suitable topical carriers include anhydrous liquid solvents such as oils, alcohols, and silicones (e.g., mineral oil, ethanol, isopropanol, dimethicone, cyclomethicone, and the like); aqueous-based single phase liquid solvents (e.g., hydro-alcoholic solvent systems); and thickened versions of these anhydrous and aqueous-based single phase solvents (e.g., where the viscosity of 9
  • the carriers of the skin care compositions can comprise from about 50% to about 99% by weight of the compositions of the present invention, preferably from about 75% to about 99%, and most preferably from about 85% to about 95%.
  • the improved carriers can further include hydro-alcoholic systems as well as oil-in-water emulsions.
  • the carrier contains a hydro-alcoholic system
  • the carrier can comprise from about 0% to about 99% of ethanol, isopropanol, or mixtures thereof, and from about 1% to about 99% of water. More preferred is a carrier comprising from about 5% to about 60% of ethanol, isopropanol, or mixtures thereof, and from about 40% to about 95% of water.
  • a carrier comprising from about 20% to about 50% of ethanol, isopropanol, or mixtures thereof, and from about 50% to about 80% of water.
  • the carrier when the carrier is an oil-in- water emulsion, the carrier can include any of the common excipient ingredients for preparing these emulsions.
  • suitable carriers are fount in U.S. Patent 5,605,894 to Blank et al., and in PCT application WO 97/39733, published October 30, 1997, to Oblong et al., both herein incorporated by reference in their entirety.
  • compositions of the present invention may optionally comprise additional skin actives.
  • skin actives include hydroxy acids such as salicylic acid and glycolic acid; keto acids such as pyruvic acid; desquamatory agents such as zwitterionic surfactants; sunscreens such as 2-ethylhexyl-p- methoxycinnamate, 4,4'-t-butyl methoxydibenzoyl-methane, octocrylene, phenyl benzimidazole sulfonic acid; sun-blocks such as zinc oxide and titanium dioxide; anti- 10
  • corticosteroids such as hydrocortisone, methylprednisolone, dexamethasone, triamcinolone acetonide, and desoxametasone
  • anesthetics such as benzocaine, dyclonine, lidocaine and tetracaine
  • antipruitics such as camphor, menthol, oatmeal (colloidal), pramoxine, benzyl alcohol, phenol and resorcinal
  • anti- oxidants/radical scavengers such as tocopherol and esters thereof
  • chelators especially iron chelators
  • retinoids such as retinol, retinyl palmitate, retinyl acetate, retinyl propionate, and retinal
  • benzofuran derivatives slimming agents such as caffeine or theophylline; and skin protectants.
  • Preferred skin actives include hydroxy acids such as salicylic acid, sunscreen, sunblock, antioxidants and mixtures thereof.
  • compositions of the present invention may also be included in the compositions of the present invention.
  • compositions of the present invention are generally prepared by conventional methods such as are known in the art of making topical compositions. Such methods typically involve mixing of the ingredients in one or more steps to a relatively uniform state, with or without heating, cooling, application of vacuum, and the like.
  • Non-limiting examples of the product form can be a gel, emulsion, lotion, cream, ointment, solution, liquid, etc.
  • compositions of the present invention are useful for treating or preventing a variety of skin conditions, especially those associated with dermis and epidermis of mammalian skin.
  • the methods disclosed in the present invention involve topically applying to the skin a safe and effective amount of the skin care composition of the present invention.
  • the amount of the composition which is applied, the frequency of application and the period of use will vary widely depending upon the level of vitamin B3 compound and/or other components of a given composition and the level of treatment desired.
  • the skin care compositions of the present invention can be chronically applied to the skin.
  • chromenic topical application is meant continued topical application of the composition over an extended period during the subject's lifetime, preferably for a period of at least about one week, more preferably for a period of at least about two weeks, even more preferably for a period of at least one month, even more preferably for at least about three months, even more preferably for at least about six months, and more preferably still for at least about one year.
  • benefits are obtainable after various maximum periods of use (e.g., five, ten or twenty years)
  • chronic application continue throughout the subject's lifetime to maintain and/or increase the benefits achieved.
  • applications would be on the order of one to four times per day over such extended periods, however application rates can be more than four times per day, especially on areas particularly-prone to dry skin such as the hands and legs. 12
  • compositions of the present invention can be employed to provide a skin appearance and/or feel benefit.
  • Quantities of the present compositions which are typically applied per application are, in mg composition/cm ⁇ skin, from about 0.1 mg/cm ⁇ to about 10 mg/cm ⁇ .
  • a particularly useful application amount is about 2 mg/cm ⁇ .
  • the method of treating the various skin conditions is preferably practiced by applying a composition in the form of a skin emulsion, lotion, cream, gel, solution, cosmetic, or the like which is intended to be left on the skin for some esthetic, prophylactic, therapeutic or other benefit (i.e., a "leave-on" composition).
  • a composition in the form of a skin emulsion, lotion, cream, gel, solution, cosmetic, or the like which is intended to be left on the skin for some esthetic, prophylactic, therapeutic or other benefit (i.e., a "leave-on" composition).
  • a composition in the form of a skin emulsion, lotion, cream, gel, solution, cosmetic, or the like which is intended to be left on the skin for some esthetic, prophylactic, therapeutic or other benefit (i.e., a "leave-on" composition).
  • the composition is preferably left on the skin for a period of at least about 15 minutes, more preferably at least about
  • the patch can be occlusive, semi-occlusive or non-occlusive.
  • the vitamin B 3 compound composition can be contained within the patch or be applied to the skin prior to application of the patch.
  • the patch can also include additional actives such as chemical initiators for exothermic reactions such as those described in PCT application WO 9701313 to Burkett et al.
  • the patch is applied at night as a form of night therapy.
  • compositions of the present invention are formed by combining and mixing the ingredients of each column using conventional technology and then applying to the skin from about from about 0.5 g to about 50g.
  • Steareth-21 (Brij 721, ICI 0.366 Americas)
  • Steareth-2 (Brij 72, ICI 1.097 Americas)
  • Distearyldimonium chloride 0.950 (Varisoft TA-100, Sherex)
  • compositions of the present invention are formed by combining and mixing the ingredients of each column using conventional technology and then applying to the skin from about from about 0.5 g to about 50g. 14
  • Caprylic/Capric Triglyceride 1.500 Myritol 318, Henkel
  • PEG-5 Glyceryl Stearate 1.050 (Arlatone 938, ICI Americas)
  • Steareth-2 (Brij 72) 1.050
  • Distearyldimonium chloride 0.250 (Varisoft TA-100)
  • Silicone fluid (Dow Corning 2.000 DC 2-1068)
  • compositions of the present invention are formed by combining and mixing the ingredients of each column using conventional technology and then applying to the skin from about from about 0.5 g to about 50g.
  • SEFA Cottonate (Sucrose 2.0000 ester of fatty acid, Procter and Gamble)
  • compositions of the present invention are formed by combining and mixing the ingredients of each column using conventional technology and then applying to the skin from about from about 0.5 g to about 50g.
  • PEG- 100 Stearate (Myrj 59, 0.1000 ICI Americas Inc.)
  • compositions of the present invention are formed by combining and mixing the ingredients of each column using conventional technology and then applying to the skin from about from about 0.5 g to about 50g.
  • Carbomer (Carbopol 1382, 0.2500 B.F. Goodrich)
  • Sorbitan monostearate (and) 5.5000 Sucrococoate (Arlatone 2121, ICI Americas Inc.)
  • Example VI The following is an example of a skin cream (water in oil) incorporating the compositions of the present invention.
  • the compositions are formed by combining and mixing the ingredients of each column using conventional technology and then applying to the skin from about from about 0.5 g to about 50g. 18
  • Silicone fluid (Goldschmidt 2.500 Abil WE-09)
  • compositions of the present invention are formed by combining and mixing the ingredients of each column using conventional technology and then applying to the skin from about from about 0.5 g to about 50g.
  • Carbomer (Carbopol 954, 0.4000 B.F. Goodrich) 19
  • Silicone fluid (Dow Corning 1.8750 3225C)
  • PEG-100 Stearate (Myrj 59, 0.3125 ICI Americas Inc.)

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

Abstract

L'invention concerne des compositions pour soins de la peau comprenant un composé à la vitamine B3 et un système de support amélioré.
PCT/US1999/005410 1998-03-16 1999-03-12 Compositions pour soins de la peau WO1999047115A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30825/99A AU3082599A (en) 1998-03-16 1999-03-12 Skin care compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7816498P 1998-03-16 1998-03-16
US60/078,164 1998-03-16

Publications (1)

Publication Number Publication Date
WO1999047115A1 true WO1999047115A1 (fr) 1999-09-23

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002069923A1 (fr) * 2001-03-05 2002-09-12 The Procter & Gamble Company Compositions antitranspiration et desodorisantes de type anhydre a base d'agent solide hydrosoluble agissant sur la peau et de glycerine
WO2002069924A1 (fr) * 2001-03-05 2002-09-12 The Procter & Gamble Company Compositions antisudorales et deodorantes contenant des particules solides de vitamines b3 et de la glycerine
WO2005016293A1 (fr) * 2003-08-07 2005-02-24 The Procter & Gamble Company Emulsions huile dans l'eau concentrees
TWI496576B (zh) * 2009-08-17 2015-08-21 Nectar Valley Biopharma Inc 清除自由基、抑制酪胺酸酶、抑制黑色素及抑制多酚氧化酶之化合物、醫藥組合物及方法
WO2021239938A1 (fr) 2020-05-29 2021-12-02 Unilever Ip Holdings B.V. Compositions cosmétiques à stabilité de couleur améliorée pour précurseur d'acide rétinoïque

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6287506A (ja) * 1985-10-15 1987-04-22 Kanebo Ltd 皮膚老化防止化粧料
WO1997039733A1 (fr) * 1996-04-23 1997-10-30 The Procter & Gamble Company Methodes de traitement et d'amelioration de l'aspect de la peau au moyen d'un compose a la vitamine b¿3?

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6287506A (ja) * 1985-10-15 1987-04-22 Kanebo Ltd 皮膚老化防止化粧料
WO1997039733A1 (fr) * 1996-04-23 1997-10-30 The Procter & Gamble Company Methodes de traitement et d'amelioration de l'aspect de la peau au moyen d'un compose a la vitamine b¿3?

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 11, no. 297 (C - 448) 25 September 1987 (1987-09-25) *
WENNINGER AND MCEWEN: "International Cosmetic Ingredient Dictionary and Handbook. Volume 2", 1997, THE COSMETIC, TOILETRY AND FRAGRANCE ASSOCIATION, WASHINGTON DC, USA, XP002103087 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002069923A1 (fr) * 2001-03-05 2002-09-12 The Procter & Gamble Company Compositions antitranspiration et desodorisantes de type anhydre a base d'agent solide hydrosoluble agissant sur la peau et de glycerine
WO2002069924A1 (fr) * 2001-03-05 2002-09-12 The Procter & Gamble Company Compositions antisudorales et deodorantes contenant des particules solides de vitamines b3 et de la glycerine
WO2005016293A1 (fr) * 2003-08-07 2005-02-24 The Procter & Gamble Company Emulsions huile dans l'eau concentrees
TWI496576B (zh) * 2009-08-17 2015-08-21 Nectar Valley Biopharma Inc 清除自由基、抑制酪胺酸酶、抑制黑色素及抑制多酚氧化酶之化合物、醫藥組合物及方法
WO2021239938A1 (fr) 2020-05-29 2021-12-02 Unilever Ip Holdings B.V. Compositions cosmétiques à stabilité de couleur améliorée pour précurseur d'acide rétinoïque

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