WO2022220027A1 - Procédé de production de composition solide, composition solide et produit cosmétique - Google Patents

Procédé de production de composition solide, composition solide et produit cosmétique Download PDF

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Publication number
WO2022220027A1
WO2022220027A1 PCT/JP2022/013266 JP2022013266W WO2022220027A1 WO 2022220027 A1 WO2022220027 A1 WO 2022220027A1 JP 2022013266 W JP2022013266 W JP 2022013266W WO 2022220027 A1 WO2022220027 A1 WO 2022220027A1
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Prior art keywords
solid composition
wax
slurry
producing
composition according
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PCT/JP2022/013266
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English (en)
Japanese (ja)
Inventor
健斗 鈴木
希佳 高橋
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株式会社資生堂
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Priority to JP2023514542A priority Critical patent/JPWO2022220027A1/ja
Publication of WO2022220027A1 publication Critical patent/WO2022220027A1/fr

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31Hydrocarbons
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/08Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/10Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/12Face or body powders for grooming, adorning or absorbing

Definitions

  • the present invention relates to a method for producing a solid composition, a solid composition, and a cosmetic.
  • Patent Document 1 a cosmetic base material containing an organic layered powder and an oil agent is mixed with a solvent such as silicone oil, the mixture is filled in a container, and the solvent is removed in a liquid state.
  • a solid powder cosmetic is disclosed.
  • Non-volatile solvents such as silicone oil are difficult to remove during the production of cosmetics, and may reduce the quality of the resulting cosmetics.
  • An object of the present invention is to provide a solid composition that facilitates removal of non-volatile solvents and suppresses quality deterioration of cosmetics.
  • a method for producing a solid composition comprises steps of preparing a mixture containing powdered wax and liquid non-volatile hydrocarbon oil, and adding a non-volatile solvent to the mixture to prepare a slurry. aspirating and filling the slurry into a container; and heating the slurry in the container to a temperature above the melting temperature of the wax.
  • FIG. 1 is a flow chart for implementing a method for producing a solid composition according to an embodiment.
  • FIG. 1 is a flow chart for implementing a method for producing a solid composition according to an embodiment.
  • the method for producing a solid composition according to this embodiment includes a step of preparing a mixture containing powdered wax and liquid non-volatile hydrocarbon oil ( FIG. 1 , step S1).
  • a solid composition refers to a solid obtained by molding a given composition.
  • the powdered wax may be powdered by pulverizing solid wax, or may be powdered wax from the beginning.
  • the average particle size of the powdered wax is arbitrary, but preferably 1 ⁇ m or more and 1000 ⁇ m or less, more preferably 10 ⁇ m or more and 600 ⁇ m or less.
  • the average particle size is the particle size at which the volume-based cumulative distribution measured by a laser diffraction/scattering method is 50%.
  • the average particle size of the wax means the average particle size before being filled with the slurry, which will be described later.
  • the melting point of the wax is not particularly limited, it is preferably 55°C or higher and 90°C or lower, more preferably 60°C or higher and 85°C or lower, and still more preferably 65°C or higher and 80°C or lower.
  • the components of the wax are not particularly limited. Isopropyl lanolin fatty acid, hexyl laurate, reduced lanolin, jojoba ester (hydrogenated jojoba oil), hard lanolin, shellac wax, beeswax, microcrystalline wax, paraffin wax, POE lanolin alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether, lanolin Fatty acid polyethylene glycol, fatty acid glyceride, hydrogenated castor oil, POE hydrogenated lanolin alcohol ether, sucrose fatty acid ester (sucrose triacetate tetrastearate) and the like. These components may be used singly or in combination of two or more.
  • the amount of the wax to be blended is arbitrary, but can be 0.5% by mass or more and 10% by mass or less, preferably 1% by mass or more and 9% by mass or less, with respect to the resulting solid composition. It is preferably 1.5% by mass or more and 8% by mass or less, more preferably 2% by mass or more and 7% by mass or less.
  • a liquid non-volatile hydrocarbon oil indicates a hydrocarbon oil with a kinematic viscosity of 5 cSt (centistokes) or more.
  • the viscosity of the non-volatile hydrocarbon oil is not particularly limited, it is preferably 10 mPa s or more and 50 mPa s or less, more preferably 15 mPa s or more and 45 mPa s or less, and still more preferably 20 mPa s at 20°C. 40 mPa ⁇ s or less.
  • Components of the liquid non-volatile hydrocarbon oil are not particularly limited, but for example, paraffin oil, mineral oil, saturated or unsaturated dodecane, saturated or unsaturated tridecane, saturated or unsaturated tetradecane, saturated or unsaturated pentadecane, saturated or unsaturated At least one non-volatile hydrocarbon oil selected from unsaturated hexadecane, or mixtures thereof.
  • nonvolatile hydrocarbon oils paraffin oil and mineral oil are preferred.
  • paraffin oil examples include liquid paraffin.
  • mineral oils examples include hydrogenated polydecene and hydrogenated polyisobutene. Among these, hydrogenated polydecene is more preferable.
  • hydrogenated polydecene refers to hydrogenated products of ⁇ -olefin oligomers.
  • the amount of the non-volatile hydrocarbon oil to be blended is arbitrary, but can be 0.5% by mass or more and 20% by mass or less, preferably 1% by mass or more and 15% by mass or less, relative to the resulting solid composition. , more preferably 2% by mass or more and 10% by mass or less, and still more preferably 3% by mass or more and 8% by mass or less.
  • the mass ratio of the nonvolatile hydrocarbon oil to the wax is not particularly limited, but is preferably 1 or more and 6 or less, more preferably 1.3 or more and 5 or less, and still more preferably 1.5 or more and 4 or less. is.
  • a mixture containing powdery wax and liquid non-volatile hydrocarbon oil may contain spherical powder.
  • spherical powder refers to powder that is approximately spherical in shape and has an aspect ratio (ratio of major axis to minor axis) of 1.2 or less.
  • the amount of the spherical powder to be blended is arbitrary, but is preferably 0.1% by mass or more and 15% by mass or less, more preferably 1% by mass or more and 10% by mass or less, and even more preferably, based on the resulting solid composition. is 3% by mass or more and 8% by mass or less.
  • the average particle size of the spherical powder is arbitrary, but is preferably 1 ⁇ m or more and 10 ⁇ m or less, more preferably 2 ⁇ m or more and 9 ⁇ m or less, and still more preferably 3 ⁇ m or more and 8 ⁇ m or less.
  • the average particle size is the particle size at which the volume-based cumulative distribution measured by a laser diffraction/scattering method is 50%.
  • the mixture may contain components other than the above components within a range that does not impair the effects of the present invention.
  • components other than the above components include powders other than the above spherical powders, coloring materials, activators, antioxidants, moisturizing agents, and the like.
  • Components of powders other than the above-mentioned spherical powders are optional, and examples include talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, leprotite, biotite, permiculite, Magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), calcium phosphate, Fluoroapatite, hydroxyapatite, ceramic powder, silicone powder, magnesium myristate (magnesium myristate), zinc myristate, calcium palmitate, aluminum stearate, chlorphenesin, boron nitride and the like. These powders may be used singly or in combination of two or more. In addition, the amount of powder to be blended is
  • the components of the coloring material are optional, and examples include red iron oxide, yellow iron oxide, black iron oxide, inorganic white pigments (e.g., zinc oxide, etc.); inorganic red pigments (e.g., iron titanate, etc.); inorganic purple system pigments (e.g., mango violet, cobalt violet, etc.); inorganic green pigments (e.g., chromium oxide, chromium hydroxide, cobalt titanate, etc.); inorganic blue pigments (e.g., ultramarine, navy blue, etc.); metal powder pigments ( For example, aluminum powder, copper powder, etc.); organic pigments such as zirconium, barium or aluminum lakes (for example, Red No. 201, Red No.
  • Red No. 204 Red No. 205, Red No. 220, Red No. 226, Red No. 228) , Red No. 405, Orange No. 203, Orange No. 204, Yellow No. 205, Yellow No. 401, Organic pigments such as Blue No. 404, Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red No. 230, Red 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Green No. 3, Blue No. 1, etc.); natural pigments (e.g., chlorophyll, ⁇ -carotene, etc.), etc. is mentioned. These coloring materials may be used singly or in combination of two or more. Note that the amount of the coloring material to be mixed is arbitrary.
  • the active agent component is optional, for example, hydrogenated lecithin, sorbitan laurate, sorbitan palmitate, sorbitan oleate, sorbitan stearate, sorbitan isostearate, sorbitan sesquioleate, sorbitan trioleate, sorbitan tristearate. , sorbitan sesquiisostearate, and the like.
  • active agents may be used singly or in combination of two or more.
  • the compounding quantity of an active agent is arbitrary.
  • antioxidants are optional, and examples include ascorbic acid, ⁇ -tocopherol, dibutylhydroxytoluene, butylhydroxyanisole, and the like. These antioxidants may be used singly or in combination of two or more. In addition, the compounding quantity of antioxidant is arbitrary.
  • ingredients of the moisturizing agent are optional, and examples include polyhydric alcohol (1,3-butylene glycol, etc.), paraoxybenzoic acid ester, phenoxyethanol, octoxyglycerin, benzoic acid, salicylic acid, phenolic acid, sorbic acid, and parachlormetacresol. , hexachlorophene, benzalkonium chloride, chlorhexidine chloride, trichlorocarbanilide and the like.
  • a method for producing a solid composition according to the present embodiment includes a step of adding a non-volatile solvent to a mixture to prepare a slurry (Fig. 1, step S2).
  • slurry refers to a suspension in which a mixture containing powdered wax and liquid non-volatile hydrocarbon oil is dispersed in a non-volatile solvent.
  • a non-volatile solvent indicates a solvent having a kinematic viscosity of 5 cSt (centistokes) or more.
  • the component of the non-volatile solvent is not particularly limited, but is preferably silicone oil.
  • the silicone oil is an oily silicone having a relatively low degree of polymerization.
  • the silicone oil is not particularly limited, and examples thereof include dimethylpolysiloxane (dimethicone), methylphenylpolysiloxane, and methylhydrogenpolysiloxane. These components may be used singly or in combination of two or more. Among these silicone oils, dimethylpolysiloxane 6CS (INCI name) is preferred.
  • the non-volatile solvent may be added at any ratio to the mixture.
  • the method for producing a solid composition according to this embodiment includes a step of sucking the slurry and filling it into a container (Fig. 1, step S3).
  • aspiration of the slurry indicates removal of the non-volatile solvent in the slurry by aspiration.
  • the mode of sucking the slurry and filling it into the container is not particularly limited, and the container may be filled after sucking the slurry solvent, or the container may be filled while sucking the slurry solvent. The solvent of the slurry may be sucked after filling the container.
  • a method can be used in which the slurry is poured into an intermediate plate, compression-molded using a molding head, and simultaneously sucked from the back surface of the molding head.
  • a method can be used in which the slurry is poured into an intermediate plate and the slurry is degassed in a reduced pressure environment using a vacuum pump or the like.
  • a wet method commonly used can be applied.
  • the method for producing a solid composition includes a step of heating the slurry in the container to a temperature equal to or higher than the melting temperature of wax (Fig. 1, step S4).
  • the melting temperature of wax indicates the melting point of wax (the temperature at which wax melts). Heating to a temperature equal to or higher than the melting temperature means heating until the wax in the slurry is completely melted.
  • a slurry is prepared by adding a non-volatile solvent to a mixture containing powdered wax and liquid non-volatile hydrocarbon oil, and the non-volatile hydrocarbon oil in the slurry is and the compatibility with the non-volatile solvent can be reduced. This facilitates removal of the non-volatile solvent during molding of the solid composition. Therefore, it becomes difficult for the non-volatile solvent to remain in the obtained solid composition.
  • a slurry is formed in which powdery wax mixed with liquid nonvolatile hydrocarbon oil is dispersed in a nonvolatile solvent.
  • the nonvolatile solvent can be easily removed, and the solid composition obtained It is possible to suppress the deterioration of the quality of things.
  • the powdery wax and the non-volatile hydrocarbon oil are more easily mixed, thereby further facilitating the removal of the non-volatile solvent. It is possible to further suppress deterioration in the quality of the obtained solid composition.
  • the non-volatile hydrocarbon oil having a viscosity of 10 mPa s or more and 50 mPa s or less at 20 ° C., the non-volatile solvent can be removed more easily. and the quality deterioration of the obtained solid composition can be further suppressed.
  • the powdery wax and the non-volatile hydrocarbon oil are more easily mixed, so that the non-volatile hydrocarbon oil and the non-volatile solvent in the slurry compatibility with can be further reduced. This makes it easier to remove the non-volatile solvent during molding of the solid composition, and makes it less likely that the non-volatile solvent will remain in the obtained solid composition.
  • the use of hydrogenated polydecene as the non-volatile hydrocarbon oil makes it easier to remove the non-volatile solvent, and the quality of the resulting solid composition can be further suppressed.
  • silicone oil has poor compatibility with nonvolatile hydrocarbon oils.
  • the solvent becomes easier to remove. Therefore, it is possible to further suppress deterioration in the quality of products using the obtained solid composition.
  • the removal of the non-volatile solvent becomes easier, and the quality of the obtained solid composition does not deteriorate. can be suppressed further.
  • the solid composition according to the present embodiment is produced by the method for producing a solid composition described above. That is, a step of preparing a mixture containing a powdered wax and a liquid non-volatile hydrocarbon oil, a step of adding a non-volatile solvent to the mixture to prepare a slurry, and a step of sucking the slurry and filling it into a container. , and a step of heating the slurry in the container to a temperature equal to or higher than the melting temperature of the wax, the solid composition according to the present embodiment can be obtained.
  • the melted wax is dispersed in the solid composition as described above. Therefore, by using such a solid composition in a product such as cosmetics, it is possible to suppress deterioration in the quality of the product.
  • the solid composition according to the present embodiment is produced by heating a slurry prepared by adding a non-volatile solvent to a mixture containing powdered wax and liquid non-volatile hydrocarbon oil to a temperature equal to or higher than the melting temperature of the wax.
  • a slurry prepared by adding a non-volatile solvent to a mixture containing powdered wax and liquid non-volatile hydrocarbon oil to a temperature equal to or higher than the melting temperature of the wax.
  • the solid composition according to the present embodiment requires promptness due to the nature of the patent application. Carrying out the task of identifying the structure or properties of the structure would be significantly more expensive and time consuming. That is, it is impossible or impractical to specify the structure or characteristics of the solid composition according to the present embodiment.
  • the cosmetic according to this embodiment contains the solid composition described above. Since the above-mentioned solid composition has the effect of suppressing the deterioration of the quality of cosmetics, such an effect can be used to apply foundation, eye shadow, cheek color, body powder, perfume powder, baby powder, pressed powder, etc. It is suitably used for solid powder cosmetics such as powders, deodorant powders and face powders.
  • ⁇ Test body> After mixing the powder with a Henschel mixer, dimethylpolysiloxane 6CS as a solvent was added to the resulting mixture to prepare a slurry. The resulting slurry is poured into a mold (middle plate) while being sucked. The slurry filled in the mold is heated in a constant temperature bath at 70° C. for 1 hour. After that, the mold is taken out from the constant temperature bath and left in a room for 1 hour, and the obtained molded article (solid matter) is used as a test piece.
  • ⁇ Surface condition> The surface condition of the obtained molded article (solid matter) was visually observed. Evaluation criteria for the surface state are shown below. In the cases of A and B, the surface condition was evaluated as good, and in the case of evaluation C, the surface condition was evaluated as poor.
  • a test piece was dropped from a height of 30 cm onto a metal plate, and the number of times it dropped until it could no longer maintain a state such as falling out of the middle plate was examined.
  • the number of tests (N) is three. Evaluation criteria for impact resistance are shown below. In the cases of A and B, the impact resistance was evaluated as good, and in the case of the evaluation of C, the impact resistance was evaluated as poor.
  • C Less than 5 times
  • Table 1 below shows the composition of ingredients and the evaluation results for Examples and Comparative Examples.
  • the specifications of the blended non-volatile hydrocarbon oil are as follows.
  • Hydrogenated polydecene Olefin Oligomer 30 (manufactured by Nikko Chemicals Co., Ltd.) (viscosity at 20 ° C.: 25 to 37 mPa s)
  • Mineral oil liquid paraffin (viscosity 21 to 26 mPa s at 20°C)
  • Vaseline semi-solid
  • Triethylhexanoin RA-G-308 (manufactured by Nippon Fine Chemical Co., Ltd.) (viscosity at 20 ° C. 20 to 35 mPa s)
  • the particle size of the component means the average particle size of the wax before the slurry is filled into the mold.
  • Examples 1 to 9 showed good solvent removal. Of these, Examples 3 to 9 had even better surface conditions, and Examples 3, 4 and 7 among them had even better impact resistance.
  • Comparative Examples 1 to 3 solvent removal was poor, and of these, Comparative Example 3 was further poor in both surface condition and impact resistance.

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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)
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  • Epidemiology (AREA)
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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)

Abstract

Procédé de production d'une composition solide, qui comprend : une étape au cours de laquelle un mélange, qui comprend une cire en poudre et une huile hydrocarbonée non volatile liquide, est préparé ; une étape au cours de laquelle un solvant non volatil est ajouté au mélange et une suspension est préparée ; une étape au cours de laquelle la suspension est aspirée et un récipient est rempli ; et une étape au cours de laquelle la suspension se trouvant à l'intérieur du récipient est chauffée jusqu'à une température qui correspond au moins à la température de fusion de la cire.
PCT/JP2022/013266 2021-04-16 2022-03-22 Procédé de production de composition solide, composition solide et produit cosmétique WO2022220027A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10338618A (ja) * 1997-06-04 1998-12-22 Kose Corp 油性固型化粧料
JP2007291074A (ja) * 2006-03-31 2007-11-08 Kose Corp 固形粉末化粧料及び固形粉末化粧料の製造方法
JP2011105605A (ja) * 2009-11-12 2011-06-02 Key Tranding Co Ltd 固形粉末化粧料の製造方法
JP2020183352A (ja) * 2019-05-07 2020-11-12 花王株式会社 固形粉末化粧料
JP2021020867A (ja) * 2019-07-26 2021-02-18 日本メナード化粧品株式会社 固形粉末化粧料

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10338618A (ja) * 1997-06-04 1998-12-22 Kose Corp 油性固型化粧料
JP2007291074A (ja) * 2006-03-31 2007-11-08 Kose Corp 固形粉末化粧料及び固形粉末化粧料の製造方法
JP2011105605A (ja) * 2009-11-12 2011-06-02 Key Tranding Co Ltd 固形粉末化粧料の製造方法
JP2020183352A (ja) * 2019-05-07 2020-11-12 花王株式会社 固形粉末化粧料
JP2021020867A (ja) * 2019-07-26 2021-02-18 日本メナード化粧品株式会社 固形粉末化粧料

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