WO2014187739A1 - Utilisation cosmétique de particules de silice hydrophobe en tant que principe actif déodorant - Google Patents

Utilisation cosmétique de particules de silice hydrophobe en tant que principe actif déodorant Download PDF

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WO2014187739A1
WO2014187739A1 PCT/EP2014/060060 EP2014060060W WO2014187739A1 WO 2014187739 A1 WO2014187739 A1 WO 2014187739A1 EP 2014060060 W EP2014060060 W EP 2014060060W WO 2014187739 A1 WO2014187739 A1 WO 2014187739A1
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Andrew Greaves
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L'oreal
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    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • 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
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • 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
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/0279—Porous; Hollow
    • 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
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/612—By organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/87—Application Devices; Containers; Packaging
    • A61K2800/874—Roll-on

Definitions

  • the present invention relates to the cosmetic use as a deodorant active agent of particles of hydrophobic silica which has been modified by at least one C8-C20- alkyl trialkoxysilane and optionally an aminoalkyl trial koxysilane and, more particularly, the said particles are present in a composition comprising a cosmetically acceptable medium.
  • the invention also relates to a cosmetic process for treating human body odour, in particular underarm odour and optionally human perspiration, which consists in applying to human keratin materials the said hydrophobic silica particles or a composition containing the same in a cosmetically acceptable medium.
  • the invention also relates to a composition characterized in that it comprises, in a cosmetically acceptable medium, at least the said particles of hydrophobic modified silica and at least one deodorant agent other than the said particles and/or at least one antiperspirant active agent.
  • Eccrine or apocrine sweat has little odour when it is secreted. It is its degradation by bacteria via enzymatic reactions which produces malodorous compounds.
  • the compounds which contribute to unpleasant underarm odour comprise malodorous steroids, volatile fatty acids, especially aliphatic, branched, saturated and/or unsaturated (C2-C12) fatty acids, and sulfanylalkanol compounds (Chem. Biodivers., 1 , 1058-1072, (2004)).
  • Certain precursors of odorous substances and mechanisms for generating them are described in the scientific literature [see, for example, Journal of Investigative Dermatology, 130, 529-540, (2010); Int. J. Cosmet. Sci., 26, 149-156, (2004)].
  • the function of deodorant active agents is to reduce or prevent the formation of unpleasant odours.
  • the various systems proposed hitherto may be grouped mainly into four large families i) to iv).
  • transition-metal-chelating agents such as ethylenediaminetetraacetic acid (EDTA) or diethylenetriaminepentaacetic acid (DTPA);
  • EDTA ethylenediaminetetraacetic acid
  • DTPA diethylenetriaminepentaacetic acid
  • iii) Unpleasant odour absorbers which "capture" or reduce the volatility of odorous compounds. Odour absorbers that may be mentioned include zeolites and cyclodextrins.
  • certain types of solid particles may be used as deodorants, such as the metal oxide silicates of patent application US 2005/063 928, the metal oxide particles modified with a transition metal in patent applications US 2005/084 464 and US 2005/084 474, aluminosilicates such as those described in patent application EP 1 658 863, and nanometric chitosan- based particles such as those described in patent US 6 916 465; and iv)
  • Antiperspirants including aluminium and/or zirconium salts, which are the most commonly used as active agents. These aluminium salts also have intrinsic efficacy since they are antibacterial agents. They thus also play a direct role on the deodorant efficacy by reducing the number of bacteria responsible for the degradation of sweat.
  • solid particle may be used as deodorants, such as the metal oxide silicates of patent application US 2005/063 928; metal oxide particles modified with a transition metal in patents US 2005/084 464 and US 2005/084 474, aluminosilicates such as those described in patent application EP 1 658 863, and nanometric chitosan-based particles such as those described in patent US 6 916 465.
  • Particles of colloidal silica modified with a transition metal and an aminosilane are also known from patent US 7 438 875, for instance 3-aminopropyltriethoxysilane (APTES), which have been used as deodorant active agent.
  • APTES 3-aminopropyltriethoxysilane
  • the invention thus relates to the cosmetic use of particles of hydrophobic silica which has been modified by at least one C 7 -C-2o-alkyl trialkoxysilane of formula (I) which will be defined in detail later and optionally by at least one aminoalkyltrialkoxysilane of formula (II) which will be defined in detail later, as a deodorant active agent and, more particularly, the said particles are present in a composition comprising a cosmetically acceptable medium.
  • the invention also relates to a cosmetic process for treating human body odour, in particular underarm odour and optionally human perspiration, which consists in applying to human keratin materials the said hydrophobic silica particles or a composition containing the same in a cosmetically acceptable medium.
  • the invention also relates to a composition characterized in that it comprises, in a cosmetically acceptable medium, at least the said particles of hydrophobic modified silica and at least one deodorant agent other than the said particles and/or at least one antiperspirant active agent.
  • physiologically acceptable medium is intended to mean a medium that is suitable for the topical administration of a composition.
  • a physiologically acceptable medium is preferentially a cosmetically or dermatologically acceptable medium, that is to say a medium which is devoid of unpleasant odour or appearance and which is entirely compatible with the topical administration route.
  • composition is intended for topical administration, that is to say for administration by application at the surface of the keratin material under consideration, such a medium is considered in particular to be physiologically acceptable when it does not cause stinging, tightness or redness unacceptable to the user.
  • deodorant active agent is intended to mean, in the context of the present invention, any active agent which, by itself alone, has the effect of masking, absorbing, improving and/or reducing the unpleasant odour resulting from the decomposition of human sweat.
  • antiperspirant active agent is intended to mean any substance which, by itself alone, has the effect of reducing the flow of sweat, of reducing the sensation on the skin of moisture associated with human sweat and of masking human sweat.
  • hydrophobic silica particles in accordance with the invention are hydrophobic silica particles that may be obtained by reaction :
  • Ri denotes a Cs to C20 alkyl group, optionally interrupted in its chain with an O or S atom or with an NH group or a carbonyl group (CO),
  • R 2 denotes a Ci-C 4 alkyl group
  • R 3 denotes a Ci-C 4 alkyl group
  • R 4 denotes a linear or branched, saturated or unsaturated Ci-C 6 , or cyclic C 3 -C 5 hydrocarbon-based group, or denotes a C 6 -C 9 aryl or C 6 -C 9 aryloxy group substituted with an amino group NH 2 or NH R with R denoting a C1-C4 alkyl radical, in an inert solvent, at a temperature ranging from 30°C to 200°C.
  • the porous particles of precipitated amorphous sil ica have a number-average particle size ranging from 1 to 25 ⁇ and preferably ranging from 1 to 20 ⁇ . Preferentially, they have a number-average size ranging from 1 to 10 ⁇ .
  • precipitated amorphous silica means a silica generally obtained by the action of an acid on a sodium silicate solution. This type of silica comprises silanol groups on its surface.
  • porous particles denotes particles having a structure comprising pores.
  • the porosity associated with the size of the particles is characterized quantitatively by their specific surface area.
  • the BET (Brunauer-Emmett-Teller) method is a method that is well known to those skilled in the art. It is described especially in the Journal of the American Chemical Society, vol . 60, page 309, February 1938, and corresponds to international standard ISO 5794/1 (appendix D).
  • the specific surface area measured according to the BET method corresponds to the total specific surface area, i.e. it includes the surface area formed by the pores.
  • the silica particles have a specific surface area measured by BET ranging especially from 300 to 1000 m 2 /g. Preferentially, the specific surface area ranges from 400 to 900 m 2 /g.
  • Spherical porous silica particles that may be used are those sold under the name Silica Beads SB-700 by the company Miyoshi; Sunsphere® H51 , Sunsphere® H33 by the company Asahi Glass.
  • Ri represents a C-s-Cis alkyl group and particularly an alkyl group chosen from n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl and n- octadecyl.
  • R2 represents an alkyl group comprising from 1 to 4 carbon atoms. More preferentially, R 2 represents a linear alkyl group comprising from 1 to 4 carbon atoms and more particularly an ethyl group.
  • compound (I) use may be made of n-octyltrimethoxysilane, n- dodecyltrimethoxysilane, n-octadecyltrimethoxysilane, n-octyltriethoxysilane, n- dodecyltriethoxysilane or n-octadecyltriethoxysilane, and mixtures thereof.
  • compound (I) is n-dodecyltriethoxysilane.
  • compound (I) is n- octadecyltriethoxysilane.
  • compound (I) is n- octyltriethoxysilane.
  • R3 represents an alkyl group comprising from 1 to 4 carbon atoms. More preferentially, R3 represents a linear alkyl group comprising from 1 to 4 carbon atoms and more particularly an ethyl group.
  • the compound of formula (II) is chosen from 3- aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3- aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane and N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.
  • APTES 3- aminopropyltriethoxysilane
  • AETES 3-aminoethyltriethoxysilane
  • 3- aminopropylmethyldiethoxysilane N-(2-aminoethyl)-3-aminopropyltriethoxysilane
  • 3-(m-aminophenoxy)propyltrimethoxysilane 3-
  • compound (II) is chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES) and N-(2-aminoethyl)-3- aminopropyltriethoxysilane. More preferentially still, compound (II) is 3- aminopropyltriethoxysilane (APTES).
  • silica and compound (I) are used in a silica/compound (I) weight ratio ranging from 0.9 to 21 .
  • silica and compound (II) are used in a silica/compound (II) weight ratio ranging from 5 to 21 .
  • toluene alkanes such as pentane, cyclopentane, hexane and cyclohexane, benzene, 1 ,4-dioxane, chloroform, dichloromethane, tetrahydrofuran, esters such as ethyl acetate and butyl acetate, formamides such as ⁇ , ⁇ -dimethylformamide (DMF), acetonitrile, dimethyl sulfoxide (DMSO), propylene carbonate, ketones such as methyl isobutyl ketone (MEK) and acetone, xylene, N-methylpyrrolidone and 1 ,3-dimethyl-3,4,5,6- tetrahydro-2(1 H)-pyrimidinone (DMPU).
  • Toluene will preferably be used as inert solvent.
  • the reaction may be performed for a time ranging from 15 minutes to 2 days.
  • the reaction is performed at a temperature ranging from 20 to 120°C.
  • the grafting reaction performed may be represented schematically in the following manner:
  • the silica obtained thus comprises groups -(0-) 3/2 Si-Ri, the radical Ri being as defined previously.
  • the concentration of particles of hydrophobic modified silica in accordance with the invention preferably ranges from 0.1 % to 100%, more preferentially from 1 % to 70% and even more preferentially from 1 % to 50% by weight relative to the total weight of the composition.
  • composition according to the invention may contain one or more additional deodorant active agents other than the hydrophobic silicas of the invention, for instance:
  • bacteriostatic agents or other bactericidal agents such as 2,4,4'-trichloro-2'- hydroxydiphenyl ether (triclosan), 2,4-dichloro-2'-hydroxydiphenyl ether, 3',4',5'- trichlorosalicylanilide, 1 -(-3',4'-dichlorophenyl)-3-(4'-chlorophenyl)urea (triclocarban) or 3,7,1 1 -trimethyldodeca-2, 5,10-trienol (Farnesol); quaternary ammonium salts, for instance cetyltrimethylammonium salts, cetylpyridinium salts; chlorhexidine and salts; diglyceryl monocaprate, diglyceryl monolaurate or glyceryl monolaurate; polyhexamethylene biguanide salts; zinc salts, such as zinc salicylate, zinc phenolsulfonate, zinc pyrroli
  • - odour absorbers such as zeolites, cyclodextrins, metal oxide silicates, such as those described in Application US 2005/063928, metal oxide particles modified by a transition metal, such as described in Applications US 2005/084464 and US 2005/084474, aluminosilicates, such as those described in Application EP 1 658 863, or particles of chitosan derivatives, such as those described in Patent US 6 916 465;
  • arylsulfatase 5-lipoxygenase, aminocylase or ⁇ -glucuronidase inhibitors
  • the additional deodorant active agents may be present in the composition according to the invention in a proportion of from 0.01 % to 10% by weight and preferably in a proportion of from 0.1 % to 5% by weight relative to the total weight of the composition.
  • composition according to the invention may contain one or more antiperspirant active agents.
  • antiperspirant active agent is intended to mean any substance which, by itself alone, has the effect of reducing the flow of sweat, of reducing the sensation on the skin of moisture associated with human sweat and of masking human sweat.
  • the antiperspirant active agents are preferably chosen from aluminium and/or zirconium salts; complexes of zirconium hydroxychloride and of aluminium hydroxychloride with an amino acid, such as those described in Patent US-3 792 068, commonly known as "ZAG" complexes.
  • ZAG complexes of zirconium hydroxychloride and of aluminium hydroxychloride with an amino acid, such as those described in Patent US-3 792 068, commonly known as "ZAG" complexes.
  • ZAG when the amino acid is glycine
  • the ZAG complexes ordinarily exhibit an Al/Zr quotient ranging from approximately 1 .67 to 12.5 and a metal/CI quotient ranging from approximately 0.73 to 1 .93.
  • aluminium zirconium octachlorohydrex GLY aluminium zirconium pentachlorohydrex GLY, aluminium zirconium tetrachlorohydrate GLY and aluminium zirconium trichlorohydrate GLY.
  • aluminium salts that may be mentioned are aluminium chlorohydrate, aluminium chlorohydrex, aluminium chlorohydrex PEG, aluminium chlorohydrex PG, aluminium dichlorohydrate, aluminium dichlorohydrex PEG, aluminium dichlorohydrex PG, aluminium sesquichlorohydrate, aluminium sesquichlorohydrex PEG, aluminium sesquichlorohydrex PG, alum salts, aluminium sulfate, aluminium zirconium octachlorohydrate, aluminium zirconium pentachlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium trichlorohydrate and more particularly the aluminium hydroxychloride sold by the company Reheis under the name Reach 301 or by the company Guilini Chemie under the name Aloxicoll PF 40. Aluminium zirconium salts are, for example, the salt sold by the company Reheis under the name Reach AZP-908-SUF.
  • Use will more particularly be made of aluminium chlorohydrate in the activated or non-activated form.
  • the antiperspirant active agents can be present in the composition according to the invention in a proportion of from 0.001 % to 30% by weight and preferably in a proportion of from 0.5% to 25% by weight, relative to the total weight of the composition.
  • composition according to the invention may be in any galenical form conventionally used for topical application and especially in the form of aqueous gels, or aqueous or aqueous-alcoholic solutions.
  • a fatty or oily phase By adding a fatty or oily phase, it may also be in the form of dispersions of lotion type, emulsions of liquid or semi- liquid consistency of milk type, obtained by dispersing a fatty phase in an aqueous phase (O/W) or conversely (W/O), or suspensions or emulsions of soft, semi-solid or solid consistency of the cream or gel type, or alternatively multiple emulsions (W/O W or O/W/O), microemulsions, vesicular dispersions of ionic and/or nonionic type, or wax/aqueous phase dispersions.
  • These compositions are prepared according to the usual methods.
  • compositions may especially be packaged in pressurized form in an aerosol device or in a pump-action bottle; packaged in a device equipped with a perforated wall, in particular a grate; packaged in a device equipped with a ball applicator ("roll-on"); packaged in the form of wands (sticks) or in the form of loose or compacted powder.
  • roll-on a ball applicator
  • wands stickss
  • loose or compacted powder contain the ingredients generally used in products of this type, which are well known to those skilled in the art.
  • compositions according to the invention can be anhydrous.
  • anhydrous composition is intended to mean a composition containing less than 2% by weight of water, indeed less than 0.5% of water, and in particular devoid of water, the water not being added during the preparation of the composition but corresponding to the residual water contributed by the mixed ingredients.
  • compositions according to the invention may be solid, in particular in wand or stick form.
  • solid composition is intended to mean that the measurement of the maximum force measured by texturometry during the penetration of a probe into the sample of formula must be at least equal to 0.25 newtons, in particular at least equal to 0.30 newtons and in particular at least equal to 0.35 newtons, assessed under precise measurement conditions as follows.
  • the formulae are poured hot into jars with a diameter of 4 cm and a depth of 3 cm. Cooling is carried out at room temperature. The hardness of the formulae produced is measured after an interval of 24 hours.
  • the jars containing the samples are characterized in texturometry using a texture analyzer such as the machine sold by the company Rheo TA-XT2, according to the following protocol : a stainless-steel ball probe 5 mm in diameter is brought into contact with the sample at a speed of 1 mm/s.
  • the measurement system detects the interface with the sample, with a detection threshold equal to 0.005 newtons.
  • the probe penetrates 0.3 mm into the sample, at a speed of 0.1 mm/s.
  • the measuring machine records the change in force measured in compression over time, during the penetration phase.
  • the hardness of the sample corresponds to the average of the maximum force values detected during penetration, over at least three measurements.
  • compositions according to the invention intended for cosmetic use may comprise at least one aqueous phase. They are in particular formulated as aqueous lotions or as water-in-oil or oil-in-water emulsions or as multiple emulsions (oil-in-water-in-oil or water-in-oil-in-water triple emulsions (such emulsions are known and described, for example, by C. Fox in "Cosmetics and Toiletries” - November 1986 - Vol. 101 - pages 101 -1 12)).
  • the aqueous phase of said compositions contains water and generally other water-soluble or water-miscible solvents.
  • the water-soluble or water-miscible solvents comprise short-chain, for example C2-C 4 , monoalcohols, such as ethanol or isopropanol; diols or polyols, such as ethylene glycol, 1 ,2-propylene glycol, 1 ,3- butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2- ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol.
  • Use will more particularly be made of propylene glycol and glycerol, and propane-1 ,3-diol.
  • composition according to the invention preferably has a pH ranging from 3 to 9, according to the support chosen.
  • Oil-in-water emulsifiers As emulsifiers that may be used in the oil-in-water emulsions or oil-in-water-in-oil triple emulsions, examples that may be mentioned include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers; sugar esters such as sucrose stearate; and mixtures thereof, such as the mixture of glyceryl stearate and PEG-40 stearate.
  • nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated
  • fatty alcohol/alkylpolyglycoside emulsifying mixtures as described in patent applications WO 92/06778, WO 95/13863 and WO 98/47610, for instance the commercial products sold by the company SEPPIC under the name Montanov®.
  • emulsifiers that may be used in the water-in-oil emulsions or water-in- oil-in-water-in-oil triple emulsions
  • examples that may be mentioned include alkyl dimethicone copolyols, for instance Cetyl PEG/PPG-10/1 Dimethicone and more particularly the mixture Cetyl PEG/PPG-10/1 Dimethicone and Dimethicone (INCI name), for instance the product sold under the trade name Abil EM90 by the company Goldschmidt, or alternatively the mixture (Polyglyceryl-4 Stearate and Cetyl PEG/PPG-10 (and) Dimethicone (and) Hexyl Laurate), for instance the product sold under the trade name Abil WE09 by the same company.
  • alkyl dimethicone copolyols for instance Cetyl PEG/PPG-10/1 Dimethicone and more particularly the mixture Cetyl PEG/PPG-10/1 Dimethicone and
  • dimethicone copolyols for instance PEG-18/PPG-18 Dimethicone and more particularly the mixture Cyclopentasiloxane (and) PEG-18/PPG-18 Dimethicone (INCI name), such as the product sold by the company Dow Corning under the trade name Silicone DC5225 C or KF-6040 from the company Shin-Etsu.
  • water-in-oil emulsifiers mention may also be made of nonionic emulsifiers derived from fatty acids and polyol, alkylpolyglycosides (APG) and sugar esters, and mixtures thereof.
  • APG alkylpolyglycosides
  • sugar esters and mixtures thereof.
  • nonionic emulsifiers derived from fatty acids and polyols use may be made especially of fatty acid esters of polyols, the fatty acid especially containing a C 8 - C24 alkyl chain, and the polyols being, for example, glycerol and sorbitan.
  • fatty acid esters of polyols Mention may in particular be made, as fatty acid esters of polyols, of isostearic acid esters of polyols, stearic acid esters of polyols, and mixtures thereof, in particular isostearic acid esters of glycerol and/or sorbitan.
  • Stearic acid esters of polyols that may especially be mentioned include the polyethylene glycol esters, for instance PEG-30 Dipolyhydroxystearate, such as the product sold under the name Arlacel P135 by the company ICI.
  • Glycerol and/or sorbitan esters that may be mentioned, for example, include polyglyceryl isostearate, such as the product sold under the name Isolan G I 34 by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI; sorbitan glyceryl isostearate, such as the product sold under the name Arlacel 986 by the company ICI, the mixture of sorbitan isostearate and polyglyceryl isostearate (3 mol) sold under the name Arlacel 1690 by the company Uniqema, and mixtures thereof.
  • polyglyceryl isostearate such as the product sold under the name Isolan G I 34 by the company Goldschmidt
  • sorbitan isostearate such as the product sold under the name Arlacel 987 by the company ICI
  • sorbitan glyceryl isostearate such as the product sold under the name Arlacel 986 by the company
  • the emulsifier may also be chosen from alkylpolyglycosides with an HLB of less than 7, for example those represented by the general formula (1 ) below:
  • the unsaturated alkyl radical may comprise one or more ethylenic unsaturations, and in particular one or two ethylenic unsaturations.
  • This alkylpolyglucoside may be used as a mixture with a coemulsifier, more especially with a fatty alcohol and especially a fatty alcohol containing the same fatty chain as that of the alkylpolyglucoside, i.e.
  • succinic-terminated polyolefins for instance esterified succinic-terminated polyisobutylenes and salts thereof, especially the diethanolamine salts, such as the products sold under the names Lubrizol 2724, Lubrizol 2722 and Lubrizol 5603 by the company Lubrizol or the commercial product Chemcinnate 2000.
  • the total amount of emulsifiers in the composition will preferably be, in the composition according to the invention, at active material contents ranging from 1 % to 8% by weight and more particularly from 2% to 6% by weight, relative to the total weight of the composition.
  • compositions according to the invention may contain at least one water- immiscible organic liquid phase, known as a fatty phase.
  • This phase generally comprises one or more hydrophobic compounds which render said phase water- immiscible.
  • the said phase is liquid (in the absence of structuring agent) at room temperature (20-25°C).
  • the water-immiscible organic liquid phase in accordance with the invention generally comprises at least one volatile oil and/or one non-volatile oil and optionally at least one structuring agent.
  • oil means a fatty substance that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg, i.e. 10 5 Pa).
  • the oil may be volatile or nonvolatile.
  • volatile oil means an oil that is capable of evaporating on contact with the skin or the keratin fibre in less than one hour, at room temperature and atmospheric pressure.
  • volatile oils of the invention are volatile cosmetic oils which are liquid at room temperature and which have a non-zero vapour pressure, at room temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10 "3 to 300 mmHg), in particular ranging from 1 .3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1 .3 Pa to 1300 Pa (0.01 to 10 mmHg).
  • non-volatile oil means an oil that remains on the skin or the keratin fibre at room temperature and atmospheric pressure for at least several hours, and that especially has a vapour pressure of less than 10 "3 mmHg (0.13 Pa).
  • the oil can be chosen from any physiologically acceptable oils and in particular cosmetically acceptable oils, in particular mineral, animal, vegetable or synthetic oils; in particular volatile or non-volatile hydrocarbon-based oils and/or silicone oils and/or fluoro oils, and mixtures thereof.
  • hydrocarbon-based oil is intended to mean an oil mainly comprising carbon and hydrogen atoms and optionally one or more functions chosen from hydroxyl, ester, ether and carboxylic functions.
  • the oil has a viscosity of from 0.5 to 100 000 mPa.s, preferably from 50 to 50 000 mPa.s and more preferably from 100 to 300 000 mPa.s.
  • volatile oils that may be used in the invention, mention may be made of:
  • volatile hydrocarbon-based oils chosen from hydrocarbon-based oils containing from 8 to 16 carbon atoms, and in particular Cs-Ci6 isoalkanes of petroleum origin (also known as isoparaffins), for instance isododecane (also known as 2,2,4,4,6- pentamethylheptane), isodecane and isohexadecane, and for example the oils sold under the trade names Isopar or Permethyl, branched Cs-Ci6 esters and isohexyl neopentanoate, and mixtures thereof.
  • Use may also be made of other volatile hydrocarbon-based oils, such as petroleum distillates, in particular those sold under the name Shell Solt by the company Shell; and volatile linear alkanes, such as those described in Patent Application DE10 2008 012 457
  • volatile silicones for instance linear or cyclic volatile silicone oils, in particular those with a viscosity of ⁇ 8 centistokes (8 * 10 "6 m 2 /s) and especially containing from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms.
  • volatile silicone oils that may be used in the invention, mention may be made especially of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane;
  • R represents an alkyl group comprising from 2 to 4 carbon atoms, one or more hydrogen atoms of which can be replaced by a fluorine or chlorine atom.
  • nonvolatile oils that may be used in the invention, mention may be made of:
  • - vegetable hydrocarbon-based oils such as liquid triglycerides of fatty acids containing 4 to 24 carbon atoms, such as heptanoic or octanoic acid triglycerides, or else wheat germ oil, olive oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy seed oil, pumpkin seed oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, sunflower oil, maize oil, soybean oil, marrow oil, grape seed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, castor oil, avocado oil, caprylic/capric acid triglycerides, such as those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel,
  • hydrocarbons of mineral or synthetic origin such as liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, polybutenes, hydrogenated polyisobutene, such as Parleam, or squalane;
  • - synthetic esters especially of fatty acids, for instance the oils of formula R1COOR2 in which Ri represents a linear or branched higher fatty acid residue containing from 1 to 40 carbon atoms and R2 represents a hydrocarbon-based chain, which is especially branched, containing from 1 to 40 carbon atoms, with Ri + R2 > 10, for instance purcellin oil (cetostearyl octanoate), isononyl isononanoate, isopropyl myristate, isopropyl palmitate, C12-C15 alkyl benzoates, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate or tridecyl trimellitate; alcohol or polyalcohol oct
  • - fatty alcohols that are liquid at room temperature, containing a branched and/or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance octyldodecanol, isostearyl alcohol, 2-butyloctanol, 2-hexyldecanol, 2- undecylpentadecanol or oleyl alcohol;
  • fluoro oils that are optionally partially hydrocarbon-based and/or silicone-based, for instance fluorosilicone oils, fluoro polyethers and fluorosilicones as described in document EP-A-847 752;
  • silicone oils for instance linear or cyclic non-volatile polydimethylsiloxanes (PDMS); polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendant or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenyl silicones, for instance phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes and 2-phenylethyl trimethylsiloxy silicates, and
  • the cosmetic compositions according to the invention may also comprise cosmetic adjuvants chosen from softeners, antioxidants, opacifiers, stabilizers, moisturizers, vitamins, bactericides, preserving agents, polymers, fragrances, a structuring agent for a fatty phase, in particular chosen from waxes, pasty compounds, and mineral or organic lipophilic gelling agents; organic or mineral fillers; thickeners or suspending agents, propellants or any other ingredient usually used in cosmetics for this type of application.
  • cosmetic adjuvants chosen from softeners, antioxidants, opacifiers, stabilizers, moisturizers, vitamins, bactericides, preserving agents, polymers, fragrances, a structuring agent for a fatty phase, in particular chosen from waxes, pasty compounds, and mineral or organic lipophilic gelling agents; organic or mineral fillers; thickeners or suspending agents, propellants or any other ingredient usually used in cosmetics for this type of application.
  • the wax is in general a lipophilic compound that is solid at room temperature (25°C), with a reversible solid/liquid change in state, having a melting point of greater than or equal to 30°C, which may be up to 200°C and in particular up to 120°C.
  • the waxes that are suitable for use in the invention may have a melting point of greater than or equal to 45°C and in particular of greater than or equal to 55°C.
  • the melting point corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in the standard ISO 1 1357-3; 1999.
  • the melting point of the wax may be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name MDSC 2920 by the company TA Instruments.
  • the measuring protocol is as follows:
  • a sample of 5 mg of wax placed in a crucible is subjected to a first temperature rise ranging from -20°C to 100°C, at a heating rate of 10°C/minute, it is then cooled from 100°C to -20°C at a cooling rate of 10°C/minute and it is finally subjected to a second temperature rise ranging from -20°C to 100°C at a heating rate of 5°C/minute.
  • the variation in the difference in power absorbed by the empty crucible and by the crucible containing the sample of wax is measured as a function of the temperature.
  • the melting point of the compound is the temperature value corresponding to the top of the peak of the curve representing the variation in the difference in power absorbed as a function of the temperature.
  • the waxes that may be used in the compositions according to the invention are chosen from waxes that are solid at room temperature of animal, vegetable, mineral or synthetic origin, and mixtures thereof.
  • waxes that are suitable for the invention, mention may be made especially of hydrocarbon-based waxes, for instance beeswax, lanolin wax, Chinese insect waxes, rice bran wax, carnauba wax, candelilla wax, ouricury wax, esparto grass wax, berry wax, shellac wax, Japan wax and sumach wax; montan wax, orange wax and lemon wax, refined sunflower wax sold under the name Sunflower Wax by Koster Keunen, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, the waxes obtained by Fischer-Tropsch synthesis and waxy copolymers, and also esters thereof.
  • hydrocarbon-based waxes for instance beeswax, lanolin wax, Chinese insect waxes, rice bran wax, carnauba wax, candelilla wax, ouricury wax, esparto grass wax, berry wax, shellac wax, Japan wax and sumach wax
  • montan wax, orange wax and lemon wax refined
  • Mention may also be made of waxes obtained by catalytic hydrogenation of animal or plant oils containing linear or branched C8-C32 fatty chains. Mention may especially be made, among these waxes, of isomerized jojoba oil such as the trans-isomerized partially hydrogenated jojoba oil manufactured or sold by the company Desert Whale under the commercial reference lso-Jojoba-50®, hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil and bis(1 ,1 ,1 -trimethylolpropane) tetrastearate sold under the name Hest 2T-4S® by the company Heterene. Mention may also be made of silicone waxes (C 30 - 4 5 alkyl dimethicone) and fluoro waxes.
  • silicone waxes C 30 - 4 5 alkyl dimethicone
  • waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol sold under the names Phytowax ricin 16L64® and 22L73® by the company Sophim, may also be used. Such waxes are described in patent application FR-A- 2 792 190.
  • wax use may be made of a C2o-C 40 alkyl (hydroxystearyloxy)stearate
  • Such a wax is especially sold under the names Kester Wax K 82 P®, Hydroxypolyester K 82 P® and Kester Wax K 80 P® by the company Koster Keunen.
  • microwaxes that may be used in the compositions according to the invention, mention may be made especially of carnauba microwaxes, such as the product sold under the name MicroCare 350® by the company Micro Powders, synthetic microwaxes, such as the product sold under the name MicroEase 1 14S® by the company Micro Powders, microwaxes consisting of a mixture of carnauba wax and polyethylene wax, such as the products sold under the names Micro Care 300® and 310® by the company Micro Powders, microwaxes consisting of a mixture of carnauba wax and of synthetic wax, such as the product sold under the name Micro Care 325® by the company Micro Powders, polyethylene microwaxes, such as the products sold under the names Micropoly 200®, 220®, 220L® and 250S® by the company Micro Powders, the commercial products Performalene 400 Polyethylene and Performalene 500-L Polyethylene from New Phase Technologies, Performalene 655, Polyethylene® or paraffin waxes, for instance the wax having the INCI
  • the term "pasty compound” means a lipophilic fatty compound that undergoes a reversible solid/liquid change of state, having in the solid state an anisotropic crystal organization, and comprising, at a temperature of 23°C, a liquid fraction and a solid fraction.
  • the pasty compound is preferably chosen from synthetic compounds and compounds of plant origin.
  • a pasty compound may be obtained by synthesis from starting materials of plant origin.
  • the pasty compound may be advantageously chosen from:
  • Lipophilic gelling agents that may be mentioned include optionally modified clays, for instance hectorites modified with a C10 to C22 ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride, for instance the product sold under the name Bentone 38V® by the company Elementis.
  • the thickeners may be chosen from carboxyvinyl polymers, such as Carbopols (Carbomers) and the Pemulens (acrylate/C10-C30 alkyl acrylate copolymer); polyacrylamides, for instance the crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide/C13-14 isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyltaurate copolymer/isohexadecane/polysorbate 80) by the company SEPPIC; 2- acrylamido-2-methylpropanesulfonic acid polymers and copolymers, optionally crosslinked and/or neutralized, for instance poly(2-acrylamido-2- methylpropanesulfonic acid) sold by the company Hoechst under the trade name Hostacerin AMPS (CTFA name: ammonium polyacryloyldimethyltaurate or Simulgel 800 sold by
  • Suspending agents In order to improve the homogeneity of the product, use may additionally be made of one or more suspending agents which are preferably chosen from hydrophobic modified montmorillonite clays, such as hydrophobic modified bentonites or hectorites.
  • hydrophobic modified montmorillonite clays such as hydrophobic modified bentonites or hectorites.
  • suspending agents include the product Stearalkonium Bentonite (CTFA name) (product of reaction of bentonite and the quaternary ammonium stearalkonium chloride) such as the commercial product sold under the name Tixogel MP 250 by the company Sud Chemie Rheologicals, United Catalysts Inc. or the product Disteardimonium Hectorite (CTFA name) (product of reaction of hectorite and distearyldimonium chloride) sold under the name Bentone 38 or Bentone Gel by the company Elementis Specialities.
  • CTFA name product of reaction of bentonite and the quaternary ammoni
  • suspension agents may be used, in the present case in hydrophilic media (aqueous and/or ethanolic). They can be derivatives of cellulose, xanthan, guar, starch, locust bean or agar agar.
  • the suspending agents are preferably present in amounts ranging from 0.1 % to 5% by weight and more preferentially from 0.2% to 2% by weight relative to the total weight of the composition.
  • compositions for treating perspiration are those conventionally used in compositions for treating perspiration. Aerosols
  • compositions according to the invention may also be pressurized and may be packaged in an aerosol device formed by:
  • A a container comprising an antiperspirant composition as defined previously, (B) at least one propellant and a means for dispensing said aerosol composition.
  • the propellants generally used in products of this type and that are well known to those skilled in the art are, for instance, dimethyl ether (DME); volatile hydrocarbons such as n-butane, propane, isobutane and mixtures thereof, optionally with at least one chlorohydrocarbon and/or fluorohydrocarbon; among these derivatives, mention may be made of the compounds sold by the company DuPont de Nemours under the names Freon® and Dymel®, and in particular monofluorotrichloromethane, difluorodichloromethane, tetrafluorodichloroethane and 1 ,1 -difluoroethane sold especially under the trade name Dymel 152 A by the company DuPont. Carbon dioxide, nitrous oxide, nitrogen or compressed air may also be used as propellant.
  • DME dimethyl ether
  • volatile hydrocarbons such as n-butane, propane, isobutane and mixtures thereof, optionally with at least one chlorohydrocarbon and/or
  • compositions comprising perlite particles as defined above and the propellant(s) can be in the same compartment or in different compartments in the aerosol container.
  • concentration of propellant generally varies from 5% to 95% by weight pressurized and more preferentially from 50% to 85% by weight, relative to the total weight of the pressurized composition.
  • the dispensing means which forms a part of the aerosol device, is generally formed by a dispensing valve controlled by a dispensing head, which itself comprises a nozzle via which the aerosol composition is vaporized.
  • the container containing the pressurized composition may be opaque or transparent. It can be made of glass, of polymer or of metal, optionally covered with a protective lacquer layer.
  • a mixture of 8 g of amorphous silica microspheres (particle size: 5 microns; Sunsphere H 51 from AGC Si-Tech) and 8 g of n-dodecyltriethoxysilane in 300 ml of toluene was refluxed for 8 hours in a three-necked flask equipped with a condenser, and was then allowed to cool for two nights.
  • the lower phase of the resulting two-phase solution was recovered and then centrifuged at 4000 rpm for 4 minutes.
  • the precipitate obtained was triturated in 200 ml of ethanol and then centrifuged. This cycle of washing and centrifugation was repeated with ethanol and then twice with distilled water (200 ml).
  • the precipitate was dried under vacuum at 80°C for 8 hours. 7.5 g of a white powder were obtained.
  • Example 3 The powder was prepared according to the procedure of Example 1 , using 10 g of amorphous silica microspheres (particle size: 5 microns; Sunsphere H 51 from AGC Si-Tech) and 10 g of n-octyltriethoxysilane in 300 ml of toluene. 9.2 g of a white powder were obtained.
  • Example 3
  • the powder was prepared according to the procedure of Example 1 , using 8 g of amorphous silica microspheres (particle size: 5 microns; Sunsphere H 51 from AGC Si-Tech) and 0.8 g of n-octadecyltriethoxysilane in 300 ml of toluene. 6.6 g of a white powder were obtained.
  • Example 5 The powder was prepared according to the procedure of Example 1 , using 3.20 g of amorphous silica microspheres (particle size: 5 microns; Sunsphere H 51 from AGC Si-Tech), 0.16 g of n-octyltriethoxysilane and 0.16 g of 3- aminopropyltriethoxysilane in 100 ml of toluene. 2.8 g of a white powder were obtained.
  • the formulae are as follows (contents expressed as weight percentages):
  • compositions C and D according to the invention make it possible to reduce efficiently the intensity of the odour.
  • the cyclopentasiloxane was heated to 65°C.
  • the other ingredients were added (one by one), while keeping the temperature at 65-70°C.
  • the whole was homogenized (transparent solution) for 15 minutes.
  • the particles of hydrophobic silica were added.
  • the product was cooled to about 55°C (a few degrees above the thickening point of the mixture) and poured into sticks. The sticks were placed at 4°C for 30 minutes.
  • composition applied to the armpits reduces the odour caused by perspiration.
  • Example 7 Deodorant emulsion (roll-on)
  • Phases (B) and (C) were separately heated to 70°C. Phases (B) and (C) were mixed together with a Turrax blender for 5 minutes, and the mixture was then cooled to 55°C with paddle stirring. Phase A was then added slowly with stirring. The mixture was homogenized for 1 to 3 minutes. The mixture was cooled to 35°C with stirring.
  • composition applied to the armpits reduces the odour caused by perspiration.
  • Example 8 Deodorant and antiperspirant emulsion (roll-on)
  • Phases (B) and (C) were separately heated to 70°C. Phases (B) and (C) were mixed together with a Turrax blender for 5 minutes, and the mixture was then cooled to 55°C with paddle stirring. Phase A was then added slowly with stirring. The mixture was homogenized for 1 to 3 minutes. The mixture was cooled to 35°C with stirring. The composition applied to the armpits reduces the odour caused by perspiration.
  • composition applied to the armpits reduces the odour caused by perspiration.
  • the particles of hydrophobic modified silica were dispersed in the mixture of the other starting materials constituting phase A, using a paddle.
  • the mixture was pressurized with isobutane in an aerosol can.
  • composition applied to the armpits reduces the odour caused by perspiration.

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Abstract

La présente invention concerne l'utilisation cosmétique, en tant que principe actif déodorant, de particules de silice hydrophobe qui peuvent être obtenues par la réaction : i) d'au moins une silice amorphe poreuse précipitée portant des groupes hydroxyles en surface avec un alkyltrialcoxysilane représenté par la formule (I) ci-dessous : R1Si(OR2)3 (l) dans laquelle R1 représente un groupe alkyle en C8 à C20, facultativement interrompu dans sa chaîne par un atome O ou S ou par un groupe NH ou un groupe carbonyle (CO), R2 représente un groupe alkyle en C1 à C4 et ii) facultativement au moins un aminoalkyltrialcoxysilane représenté par la formule (II) ci-dessous : R4Si(OR3)3 (II) dans laquelle R3 représente un groupe alkyle en C1 à C4, R4 représente une groupe hydrocarboné linéaire ou ramifié, saturé ou insaturé en C1 à C6, ou cyclique en C3 à C5, ou représente un groupe aryle en C6 à C9 ou un groupe aryloxy en C6 à C9 substitué par un groupe amino NH2 ou NHR, R représentant un radical alkyle en C1 à C4, dans un solvant inerte, à une température se situant dans la plage de 30 °C à 200 °C. L'invention concerne également un procédé cosmétique destiné à traiter une odeur corporelle humaine, en particulier une odeur axillaire et facultativement la transpiration humaine, ledit procédé consistant à appliquer à des matières kératiniques humaines lesdites particules de silice hydrophobe ou une composition les contenant dans un milieu acceptable d'un point de vue cosmétique.
PCT/EP2014/060060 2013-05-23 2014-05-16 Utilisation cosmétique de particules de silice hydrophobe en tant que principe actif déodorant WO2014187739A1 (fr)

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CN108272648A (zh) * 2018-03-26 2018-07-13 上海蔻沣生物科技有限公司 化妆品粉体、油性色浆及其制备方法
WO2020218102A1 (fr) * 2019-04-26 2020-10-29 小林製薬株式会社 Composition déodorante en poudre

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108272648A (zh) * 2018-03-26 2018-07-13 上海蔻沣生物科技有限公司 化妆品粉体、油性色浆及其制备方法
WO2020218102A1 (fr) * 2019-04-26 2020-10-29 小林製薬株式会社 Composition déodorante en poudre

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