WO2017221940A1 - 化粧料用粉体の処理剤、化粧料用粉体、およびこれを配合した化粧料 - Google Patents
化粧料用粉体の処理剤、化粧料用粉体、およびこれを配合した化粧料 Download PDFInfo
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- WO2017221940A1 WO2017221940A1 PCT/JP2017/022734 JP2017022734W WO2017221940A1 WO 2017221940 A1 WO2017221940 A1 WO 2017221940A1 JP 2017022734 W JP2017022734 W JP 2017022734W WO 2017221940 A1 WO2017221940 A1 WO 2017221940A1
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- powder
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- acid
- oil
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- 0 C*(C)N(*)C(*)(*)OC Chemical compound C*(C)N(*)C(*)(*)OC 0.000 description 1
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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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
-
- 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
- A61K8/022—Powders; Compacted Powders
-
- 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
- A61K8/29—Titanium; Compounds thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- A61K2800/614—By macromolecular 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
- A61K2800/40—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
- A61K2800/62—Coated
- A61K2800/623—Coating mediated by organosilicone compounds
-
- 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
- A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
Definitions
- the present invention relates to a novel cosmetic powder treatment agent, a cosmetic powder surface-treated with the treatment agent, and a cosmetic containing the same.
- a cosmetic powder treating agent capable of imparting excellent lipophilicity.
- a cosmetic powder, a cosmetic raw material, or a cosmetic using the same which has a cosmetic effect and has an excellent feeling of use by including the treatment agent or being treated thereby. To do.
- One cosmetic powder treating agent of the present invention is characterized by containing a reactive organosiloxane represented by the following general formula (1) as a main agent.
- each R 1 is independently an alkyl group having 1 to 30 carbon atoms.
- Each R 2 is independently an alkyl group having 1 to 20 carbon atoms.
- R 3 is a divalent alkylene group.
- N is an integer from 1 to 200, and p is an integer from 1 to 3.
- One cosmetic powder according to the present invention is characterized by comprising a cosmetic powder surface-treated with the above-mentioned treatment agent.
- One cosmetic raw material of the present invention is characterized by comprising a cosmetic powder.
- one cosmetic of the present invention is characterized by including the cosmetic powder.
- the cosmetic powder treating agent of the present invention can impart lipophilicity, compatibility and dispersibility to the powder relatively easily without leaving SiH bonds in the powder. For this reason, the powder for cosmetics of this invention not only has high lipophilicity, compatibility, and dispersibility, but also has high storage stability and ease of handling. Moreover, the powder for cosmetics of this invention has the favorable dispersibility in cosmetics, is excellent in temporal stability, and can give a smooth feeling of use to skin.
- the cosmetic of the present invention has the above effects.
- One of the present invention is a treatment agent for a cosmetic powder containing a reactive organosiloxane represented by the following general formula (1) as a main ingredient.
- each R 1 is independently an alkyl group having 1 to 30 carbon atoms.
- Each R 2 is independently an alkyl group having 1 to 20 carbon atoms.
- R 3 is a divalent alkylene group.
- N is an integer from 1 to 200, and p is an integer from 1 to 3.
- R 1 in formula (1) examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, lauryl group, cetyl group, stearyl group. And alkyl groups such as a behenyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group.
- R 1 is a methyl group or an octyl group, or the terminal R 1 is a methyl group or an octyl group, and R 1 other than the terminal is a methyl group.
- R 2 in the formula (1) is an alkyl group having 1 to 20 carbon atoms.
- An alkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a methyl group, or an ethyl group is preferable.
- R 3 in the formula (1) is a divalent alkylene group.
- R 3 is preferably an alkylene group having 3 to 18 carbon atoms, an alkylene group having 4 to 15 carbon atoms, or an alkylene group having 6 to 13 carbon atoms because of compatibility of the cosmetic powder with an oil used in cosmetics. It is a group.
- R 3 may be linear or partially branched or cyclic.
- N in the formula (1) is an integer of 1 to 200.
- n is 5 or more, 10 or more, and n is 160 or less, 120 or less, 100 or less, or 80 or less from the compatibility of the cosmetic powder with the silicone oil used in cosmetics.
- the number average molecular weight of the reactive organosiloxane represented by the formula (1) is preferably 300 to 100,000, or 1,000 to 10,000, although it varies depending on the powder to be treated. Are appropriately selected.
- the treatment agent for cosmetic powder according to the present invention contains the reactive organosiloxane represented by the general formula (1) as a main agent, and the content ratio may be an amount capable of producing the effect as a treatment agent. .
- the content of the organosiloxane in the treatment agent is 1% by mass or more, 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass or more, or 25% by mass or more.
- the treating agent may be used when the reactive organosiloxane represented by the general formula (1) is used alone or in combination with one or more other components.
- the powder treatment using the treatment agent for the powder for cosmetics of the present invention can be performed by a known method such as a wet method or a dry method.
- a known method such as a wet method or a dry method.
- the following method is mentioned. 1.
- a method of surface treatment using a pulverizer such as a ball mill or jet mill after mixing the powder and the treatment agent.
- a treating agent is mixed with a solvent, powder is dispersed in the mixture, and then the solvent is dried to perform surface treatment.
- the powder is surface-treated, it is a method of passing through a jet mill.
- Examples of the method of passing the powder after surface treatment and passing it through a jet mill include the following two methods. (1) A method of mixing and dispersing a surface treatment agent and powder by a dry method or a wet method, and then drying by heating through a jet mill. (2) A method of mixing and dispersing a surface treatment agent and a powder by a dry method or a wet method. This is a method of passing through a jet mill after heating and drying.
- a pulverizer such as a pin mill or a hammer mill can be used instead of a jet mill.
- the mixing and dispersing machine used for mixing and contacting the above powders is Hensyl mixer, ribbon blender, Q mill, kneader, planetary mixer, pony mixer, Banbury mixer, ball mill, dry sand mill, wet sand mill, attritor, disperser.
- a mixer, a homomixer, an extruder, etc. are mentioned.
- the surface treatment may be performed while applying energy such as mechanochemical mechanical force, ultrasonic wave, plasma, flame, ultraviolet ray, electron beam, superheated steam or the like.
- the amount of the treatment agent used relative to the untreated cosmetic powder is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the untreated cosmetic powder.
- the amount ratio is preferably 1 to 20 parts by mass of the treatment agent with respect to 100 parts by mass of the cosmetic powder.
- the powder surface-treated with the mixing and dispersing machine is dried at a temperature of 100 ° C. to 170 ° C. for 3 hours to 20 hours, for example, in order to complete the reaction between the treatment agent and the powder particle surface.
- easy dispersion is further improved when the powder is mixed and contacted and then the surface-treated powder is pulverized using a jet mill pulverizer.
- the jet mill is roughly classified into a fluidized bed type, a spiral type, a jet ohmizer type and the like, and any type can be used, but a fluidized bed type capable of uniformly and efficiently treating is most preferable.
- the particle diameter of the cosmetic powder of the present invention is expressed in median diameter, and the value is preferably 0.50 ⁇ m or less, preferably 0.40 ⁇ m or less, or 0.30 ⁇ m or less. Further, the particle diameter corresponding to 50% of the cumulative distribution is represented by D50, D84 represents the particle diameter at the point where the cumulative curve becomes 84%, and D16 represents the particle diameter at the point where the cumulative curve becomes 16%.
- cosmetic powders that can be surface-treated with the treatment agent of the present invention
- the shape can be used for ordinary cosmetics.
- particle structures can be used.
- cosmetic powders include inorganic powders, organic powders, surfactant metal salt powders, colored pigments, pearl pigments, metal powder pigments, extender pigments, natural pigments, and the like.
- Inorganic powders include titanium oxide, zirconium oxide, zinc oxide, cerium oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite, synthetic mica Phlogopite, red mica, biotite, lithia mica, silicic acid, anhydrous silicic acid, aluminum silicate, magnesium silicate, magnesium magnesium silicate, calcium silicate, barium silicate, strontium silicate, metal tungstate, Hydroxyapatite, vermiculite, hydrite, bentonite, montmorillonite, hectorite, zeolite, ceramic powder, dicalcium phosphate, alumina, aluminum hydroxide, boron nitride, boron nitride, silica, etc.
- Organic powders include polyamide powder, polyester powder, polyethylene powder, polypropylene powder, polystyrene powder, polyurethane, benzoguanamine powder, polymethylbenzoguanamine powder, tetrafluoroethylene powder, polymethylmethacrylate powder, cellulose, silk powder, nylon powder, 12 Nylon, 6 nylon, crosslinked silicone fine powder obtained by crosslinking dimethyl silicone, polymethylsilsesquioxane fine powder, styrene / acrylic acid copolymer, divinylbenzene / styrene copolymer, vinyl resin, urea resin, Phenol resin, fluorine resin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, microcrystalline fiber powder, starch powder, Lauro Rurijin, and the like.
- surfactant metal salt powder examples include zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, zinc cetyl phosphate, calcium cetyl phosphate, and sodium zinc cetyl phosphate.
- colored pigments include inorganic red pigments such as iron oxide, iron hydroxide and iron titanate, inorganic brown pigments such as ⁇ -iron oxide, inorganic yellow pigments such as yellow iron oxide and loess, black oxidation Inorganic black pigments such as iron and carbon black, inorganic purple pigments such as manganese violet and cobalt violet, inorganic green pigments such as chromium hydroxide, chromium oxide, cobalt oxide and cobalt titanate, inorganic blue pigments such as bitumen and ultramarine Tar dyes raked, natural dyes raked, and These powders complexed synthetic resin powder and the like.
- inorganic red pigments such as iron oxide, iron hydroxide and iron titanate
- inorganic brown pigments such as ⁇ -iron oxide
- inorganic yellow pigments such as yellow iron oxide and loess
- black oxidation Inorganic black pigments such as iron and carbon black
- inorganic purple pigments such as manganese violet and co
- pearl pigments examples include titanium oxide-coated mica, titanium oxide-coated mica, bismuth oxychloride, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, fish scale foil, titanium oxide-coated colored mica, and the like. Copper powder, stainless steel powder, etc .; As tar pigments, Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, Red No. 226, Red No. 227 No., Red No. 228, Red No. 230, Red No. 401, Red No. 505, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Yellow No.
- Yellow No. 401 Yellow No. 1, Blue No. 2, Blue 201, Blue 404, Green 3, Green 201, Green 204, Green 205, Orange 201, Orange 2 No. 3, No. 204 orange 206 Orange No. 207 Orange No. and the like; examples of the natural pigment, carminic acid, laccaic acid, carthamin, brazilin, powders and the like selected and crocin.
- the cosmetic powder surface-treated with the treatment agent of the present invention is suitable as a cosmetic raw material.
- the blending amount is preferably adjusted according to the type and dosage form of the cosmetic and the properties of the powder. Usually, it is blended in an amount of 0.1 to 70% by weight, typically 1 to 50% by weight, more typically 1 to 40% by weight based on the total weight of the cosmetic.
- the treatment amount of the untreated cosmetic powder and the treatment agent is preferably 0.1 to 30 parts by mass of the treatment agent with respect to 100 parts by mass of the cosmetic powder.
- the blending ratio is preferably 1 to 20 parts by mass of the treatment agent with respect to 100 parts by mass of the cosmetic powder.
- the cosmetic raw material referred to in the present invention may be in the form of a liquid dispersion (slurry).
- the cosmetic powder after the treatment with the cosmetic powder treatment agent is dispersed in the oil, or the organosiloxane is dissolved or dispersed in the oil, and the powder is added thereto.
- the content of the cosmetic powder and oil in the cosmetic raw material is preferably 10 to 5,000 parts by mass with respect to 100 parts by mass of the cosmetic powder after treatment.
- the content of the oil agent is preferably 30 parts by mass or more, 50 parts by mass or more, 100 parts by mass or more, 200 parts by mass or more, 5,000 parts by mass or less, 3,000 with respect to 100 parts by mass of the cosmetic powder. It is not more than part by mass, not more than 2,000 parts by mass, or not more than 1,000 parts by mass.
- the oil agent is not particularly limited as long as a liquid dispersion can be prepared, and is generally used as a component of cosmetics. Usually, it is a liquid at room temperature, but is a solid such as wax. It may be a high-viscosity and viscous gum or paste that will be described later.
- the oil agent is preferably one or more oil agents selected from silicone oil, non-polar organic compound or low-polar organic compound that is liquid at 5 to 100 ° C.
- one or more kinds of “(B) oil” can be blended depending on the purpose. As long as it is used for normal cosmetics, any oil agent of solid, semi-solid and liquid can be used.
- natural animal and vegetable oils and semi-synthetic oils and fats include avocado oil, linseed oil, almond oil, ibotarou, eno oil, olive oil, cacao oil, kapok wax, kayak oil, carnauba wax, liver oil, candelilla wax, beef fat, cow leg fat, Beef bone fat, hydrogenated beef tallow, Kyonin oil, whale wax, hydrogenated oil, wheat germ oil, sesame oil, rice germ oil, rice bran oil, sugarcane wax, sasanqua oil, safflower oil, shea butter, cinnamon oil, cinnamon oil, jojoballow , Shellac oil, turtle oil, soybean oil, tea seed oil, camellia oil, evening primrose oil, corn oil, lard, rapeseed oil, Japanese kiri oil, nukarou, germ oil, horse fat, persic oil, palm oil, palm kernel oil, Castor oil, hydrogenated castor oil, castor oil fatty acid methyl ester, sunflower oil, grape oil, bayberry wax
- higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behen Examples thereof include acid, undecylenic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid
- Higher alcohols include lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, behenyl alcohol, hexadecyl alcohol, oleyl alcohol, isostearyl alcohol, hexyl decanol, octyldodecanol, cetostearyl alcohol, 2-decyltetradecinol, cholesterol , Phytosterol, POE cholesterol ether, monostearyl glycerin ether (batyl alcohol), monooleyl glyceryl ether (ceracyl alcohol) and the like.
- Ester oils include diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, N-alkyl glycol monoisostearate, isocetyl isostearate, trimethylolpropane triisostearate, di-2-ethylhexane Ethylene glycol, cetyl 2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl octoate, octyldodecyl gum ester, oleyl oleate, octyldodecyl oleate, Decyl oleate, neopentyl glycol dicaprate, triethyl citrate, 2-ethylhexyl succinate, amyl
- Silicone oils include low to high viscosity organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, dimethylsiloxane / methylphenylsiloxane copolymer, octamethylcyclotetrasiloxane, decamethylcyclopenta Cyclic siloxanes such as siloxane, dodecamethylcyclohexasiloxane, tetramethyltetrahydrogencyclotetrasiloxane, tetramethyltetraphenylcyclotetrasiloxane, etc., highly polymerized gum-like dimethylpolysiloxane, gum-like dimethylsiloxane / methylphenylsiloxane copolymer Silicone rubber such as coalescence, and cyclic siloxane solution of silicone rubber, trimethylsiloxysilicic acid, cyclic si
- the blending amount of these (B) oil agents varies depending on the agent system, but is 1 to 98% by mass, preferably 2 to 50%, based on the total cosmetic.
- the cosmetic of the present invention can be mixed with “(C) water” according to the purpose.
- the blending amount varies depending on the agent system, but is 1 to 95% by weight, preferably 5 to 80%, based on the total cosmetic.
- one or more “(D) surfactants” may be used depending on the purpose.
- Such surfactants include anionic, cationic, nonionic and amphoteric active agents.
- anionic surfactants include fatty acid soaps such as sodium stearate and triethanolamine palmitate, alkyl ether carboxylic acids and salts thereof, condensates of amino acids and fatty acids, alkane sulfonates, and alkene sulfonic acids.
- Salts sulfonates of fatty acid esters, sulfonates of fatty acid amides, formalin condensation sulfonates, alkyl sulfates, secondary higher alcohol sulfates, alkyl and allyl ether sulfates, sulfates of fatty acid esters Salts, sulfate esters of fatty acid alkylolamide, sulfate esters such as funnel oil, alkyl phosphates, ether phosphates, alkyl allyl ether phosphates, amide phosphates, N-acyl amino acid based activators, etc .; cations Active surfactant
- the alkylamine salts, polyamines and amine salts such as an amino alcohol fatty acid derivatives, alkyl quaternary ammonium salts, aromatic quaternary ammonium salts, pyridinium salts and imidazolium salts.
- Nonionic surfactants include sorbitan fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyethylene glycol fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkyl ether, polyoxypropylene alkyl ether, polyoxy Ethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene propylene glycol fatty acid ester, polyoxyethylene castor oil, polyoxyethylene cured Castor oil, polyoxyethylene phytostanol ether, polyoxyethylene N-phytosterol ether, polyoxyethylene cholestanol ether, polyoxyethylene cholesteryl ether, linear or branched polyoxyalkylene-modified organopolysiloxane, linear or
- amphoteric surfactants examples include betaines, aminocarboxylates, imidazoline derivatives, and amidoamine types.
- fatty acid soaps such as sodium stearate and triethanolamine palmitate, alkyl sulfates, alkyl phosphates, and alkyl quaternaries are generally easy to give stable O / W emulsions.
- Anionic surfactant such as ammonium salt; and sorbitan fatty acid ester, glycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene hydrogenated castor oil, linear or branched polyoxyalkylene modified organopolysiloxane, linear or branched Nonionic surfactants such as polyoxyalkylene-alkyl co-modified organopolysiloxanes, particularly nonionic surfactants having an HLB of 2 to 8 are preferred. Further, linear or branched silicones having a polyoxyalkylene chain and a polyglycerin chain are generally preferred for W / O type cosmetics.
- the compounding amount of the surfactant is in the range of 0.1 to 20% by mass, particularly preferably 0.2 to 10% by mass, based on the total cosmetic.
- (E) a compound having an alcoholic hydroxyl group may be used alone or in combination of two or more depending on the purpose.
- Examples of compounds having an alcoholic hydroxyl group that can be added in the present invention include lower alcohols such as ethanol and isopropanol, sugar alcohols such as sorbitol and maltose, sterols such as cholesterol, sitosterol, phytosterol, and lanosterol, butylene glycol, There are polyhydric alcohols such as propylene glycol and dibutylene glycol.
- the blending amount is preferably in the range of 0.1 to 98% by mass of the entire cosmetic.
- (F) water-soluble or water-swellable polymer can be used alone or in combination of two or more depending on the purpose.
- plant systems such as gum arabic, tragacanth, galactan, carob gum, guar gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), starch (rice, corn, potato, wheat), alge colloid, tant gum, locust bean gum Macromolecules such as polymers, xanthan gum, dextran, succinoglucan, pullulan, animal polymers such as collagen, casein, albumin, gelatin, starch polymers such as carboxymethyl starch and methylhydroxypropyl starch, methylcellulose, Ethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, nitrocellulose, cellulose Sodium sulfate, sodium carboxymethyl cellulose, crystalline cellulose, cellulose polymer such as cellulose powder, alginic acid polymers such as sodium alginate and propylene glycol alginate, vinyl polymers such as polyvinyl
- the cosmetic of the present invention at least one silicone resin selected from acrylic silicone resin and reticulated silicone resin can be used according to the purpose.
- the acrylic silicone resin may be either an acrylic / silicone graft polymer or a block copolymer. However, these reticulated silicone resins do not have SiH bonds.
- the acrylic silicone resin and the reticulated silicone resin have at least one selected from a pyrrolidone moiety, a long-chain alkyl moiety, a polyoxyalkylene moiety and a fluoroalkyl moiety, a carboxylic acid, and an amino group.
- the acrylic silicone resin or the reticulated silicone resin is preferably 0.1 to 20% by mass, more preferably 1 to 10% by mass, based on the total amount of the cosmetic.
- the cosmetics of the present invention include components used in ordinary cosmetics, oil-soluble gelling agents, organically modified clay minerals, resins, antiperspirants, ultraviolet absorbers, ultraviolet rays, as long as the effects of the present invention are not hindered.
- Oil-soluble gelling agents include metal soaps such as aluminum stearate, magnesium stearate, zinc myristate, amino acid derivatives such as N-lauroyl-L-glutamic acid, ⁇ , ⁇ -di-n-butylamine, and dextrin palmitate
- Dextrin stearates dextrin fatty acid esters such as dextrin 2-ethylhexanoic acid palmitate
- sucrose fatty acid esters such as sucrose palmitate, sucrose stearate, monobenzylidene sorbitol, sorbitol such as dibenzylidene sorbitol
- a gel selected from organically modified clay minerals such as benzylidene derivatives, dimethylbenzyl dodecyl ammonium montmorillonite clay, and dimethyl dioctadecyl ammonium montmorillonite clay.
- Enumerators include metal soaps such as aluminum stearate, magnesium stearate, zinc
- Antiperspirants include antiperspirants selected from aluminum chlorohydrate, aluminum chloride, aluminum sesquichlorohydrate, zirconyl hydroxychloride, aluminum zirconium hydroxychloride, aluminum zirconium glycine complex, and the like.
- UV absorbers include benzoic acid-based UV absorbers such as paraaminobenzoic acid, anthranilic acid-based UV absorbers such as methyl anthranilate, salicylic acid-based UV absorbers such as methyl salicylate, and cinnamon such as octyl paramethoxycinnamate.
- Acid UV absorbers, benzophenone UV absorbers such as 2,4-dihydroxybenzophenone, urocanic acid UV absorbers such as ethyl urocanate, dibenzoyl such as 4-t-butyl-4'-methoxy-dibenzoylmethane Methane-based ultraviolet absorbers and the like are exemplified.
- Ultraviolet absorbing and scattering agents include powders that absorb and scatter ultraviolet rays, such as fine particle titanium oxide, fine particle iron-containing titanium oxide, fine particle zinc oxide, fine particle cerium oxide, and their composites. .
- Moisturizers include glycerin, sorbitol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, glucose, xylitol, maltitol, polyethylene glycol, hyaluronic acid, chondroitin sulfate, pyrrolidone carboxylate, polyoxyethylene methyl glucoside, Examples include polyoxypropylene methyl glucoside.
- Antibacterial and antiseptic agents include paraoxybenzoic acid alkyl esters, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, etc.
- Antibacterial agents include benzoic acid, salicylic acid, carboxylic acid, sorbic acid, paraoxybenzoic acid alkyl ester , Parachlorometacresol, hexachlorophene, benzalkonium chloride, chlorhexidine chloride, trichlorocarbanilide, photosensitizer, phenoxyethanol and the like.
- Antioxidants include tocopherol, butylhydroxyanisole, dibutylhydroxytoluene, phytic acid, etc.
- pH adjusters include lactic acid, citric acid, glycolic acid, succinic acid, tartaric acid, dl-malic acid, potassium carbonate, sodium bicarbonate , Ammonium bicarbonate, etc., as a chelating agent, alanine, sodium edetate, sodium polyphosphate, sodium metaphosphate, phosphoric acid, etc., as a refreshing agent, L-menthol, camphor, etc., as an anti-inflammatory agent, allantoin, Examples include glycyrrhizic acid and salts thereof, glycyrrhetinic acid and stearyl glycyrrhetinate, tranexamic acid, and azulene.
- Skin beautifying ingredients include placenta extract, whitening agent such as arbutin, glutathione, and yukinoshita extract, royal jelly, photosensitizer, cholesterol derivative, cell activator such as calf blood extract, rough skin improver, nonyl acid wallenylamide, Nicotinic acid benzyl ester, nicotinic acid ⁇ -butoxyethyl ester, capsaicin, zingerone, cantalis tincture, ictamol, caffeine, tannic acid, ⁇ -borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandrate, cinnarizine, trazoline, Examples thereof include blood circulation promoters such as acetylcholine, verapamil, cephalanthin and ⁇ -oryzanol, skin astringents such as zinc oxide and tannic acid, and antiseborrheic agents such as sulfur and thiant
- Vitamins include vitamin A oil, retinol, retinol acetate, retinol palmitate, etc., vitamin B2 such as riboflavin, riboflavin butyrate, flavin adenine nucleotide, pyridoxine hydrochloride, pyridoxine dioctanoate, pyridoxine tripalmi Vitamin B6 such as tate, vitamin B12 and derivatives thereof, vitamin B such as vitamin B15 and derivatives thereof, L-ascorbic acid, L-ascorbic acid dipalmitate, L-ascorbic acid-2-sodium sulfate, L- Vitamin C such as ascorbic acid phosphate diester dipotassium, vitamin D such as ergocalciferol and cholecalciferol, ⁇ -tocopherol, ⁇ -tocopherol, dl- ⁇ -tocopherol acetate Vitamin E such as dl- ⁇ -tocopherol acetate Vitamin E such as
- amino acids As amino acids, glycine, valine, leucine, isoleucine, serine, threonine, phenylalanine, arginine, lysine, aspartic acid, glutamic acid, cystine, cysteine, methionine, tryptophan, etc., nucleic acid, deoxyribonucleic acid, etc., hormone, estradiol , Etenyl estradiol and the like.
- hair fixative polymer compound examples include amphoteric, anionic, cationic, and nonionic polymer compounds, such as polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers.
- Acid vinyl ether polymer such as methyl vinyl ether / maleic anhydride alkyl half ester copolymer, acid polyvinyl acetate polymer such as vinyl acetate / crotonic acid copolymer, (meth) acrylic acid / alkyl (meth) acrylate Copolymers, acidic acrylic polymer compounds such as (meth) acrylic acid / alkyl (meth) acrylate / alkylacrylamide copolymers, N-methacryloylethyl-N, N-dimethylammonium / ⁇ -N-methylcarboxybetaine / Alkyl (meth) acrylate copolymer, hydride Kishipuropiru (meth) acrylate / butylamino
- cosmetics refer to skin lotions, emulsions, creams, cleansings, packs, oil liquids, massage agents, cleaning agents, deodorants, hand creams, lip balms, and other skin care cosmetics, makeup bases, white powders, liquid foundations. , Oily foundation, blusher, eyeshadow, mascara, eyeliner, eyebrow, lipstick, and other makeup cosmetics, shampoos, rinses, hair treatments such as treatments, set agents, antiperspirants, sunscreen emulsions and sunscreen creams UV protection cosmetics such as are exemplified.
- These cosmetics can be in various forms such as liquid, emulsion, cream, solid, paste, gel, powder, press, mousse, spray, stick, pencil, etc. It may be.
- reaction solution 0.5 g was sampled, and the reaction was completed by the alkali decomposition gas generation method (the remaining Si—H group was decomposed with an ethanol / water solution of KOH, and the reaction rate was calculated from the volume of the generated hydrogen gas). I confirmed that.
- the reaction solution is heated to 150 to 160 ° C. under reduced pressure to remove low-boiling components such as isopropyl alcohol, and then the following formula (3): 192 g of a cosmetic powder treating agent containing 80% or more of the reactive organosiloxane represented by the formula (1) was obtained.
- the above formula was confirmed by 1 H-NMR and 29 Si-NMR.
- the viscosity was measured according to JIS-Z-8803 using an Ubbelohde viscosity tube, and it was 31 mm 2 / s.
- the above formula was confirmed by 1 H-NMR and 29 Si-NMR.
- the viscosity of the obtained reactive organosiloxane was measured according to JIS-Z-8803 using an Ubbelohde type viscosity tube, and found to be 51 mm 2 / s.
- Examples 1 and 2 and Comparative Example 1 A solution in which 50 g of n-hexane was added to 50 g of untreated fine particle titanium oxide (STR-100N manufactured by Sakai Chemical Industry Co., Ltd.) and mixed with 2.5 g of the treatment agent produced in Synthesis Example 1 and 5 g of hexane while stirring with a disper. After the dropwise addition, the mixture was further stirred with a disper for 10 minutes. Next, after 10 minutes in an ultrasonic cleaner, n-hexane was removed under normal pressure while stirring at 100 ° C., followed by baking at 150 ° C. for 3 hours while stirring under reduced pressure to obtain a cosmetic powder. It was.
- Example 1 a slurry-like cosmetic containing titanium oxide treated with 5 parts of the treating agent of Synthesis Example 1 with respect to 100 parts of untreated titanium oxide.
- the raw material was obtained.
- Example 2 a slurry-like cosmetic raw material containing titanium oxide similarly treated using the treating agent of Synthesis Example 2 was obtained.
- Comparative Example 1 a slurry-like cosmetic material containing titanium oxide having the same composition was prepared using a powder obtained by similarly treating 100 parts of untreated titanium oxide with 5 parts of methylhydrogenpolysiloxane. .
- the particle size ( ⁇ m) is represented, and D16 represents the particle size ( ⁇ m) at which the cumulative curve becomes 16%.
- Examples 3 to 4 and Comparative Example 2 A solution prepared by adding 50 g of n-hexane to 50 g of untreated fine particle titanium oxide (STR-100N manufactured by Sakai Chemical Industry Co., Ltd.) and mixing 5 g of the powder treating agent produced in Synthesis Example 1 and 5 g of hexane while stirring with a disper. After the dropwise addition, the mixture was further stirred with a disper for 10 minutes. Next, after 10 minutes in an ultrasonic cleaner, n-hexane was removed under normal pressure while stirring at 100 ° C., followed by baking at 150 ° C. for 3 hours while stirring under reduced pressure to obtain a cosmetic powder. It was.
- Example 4 a slurry-like cosmetic raw material containing titanium oxide treated in the same manner using the treating agent of Synthesis Example 2 was obtained. Further, as Comparative Example 2, a slurry-like cosmetic material containing titanium oxide having the same composition was prepared using fine-particle titanium oxide (MTY-02 manufactured by Teika Co., Ltd.) treated with methyl hydrogen polysiloxane.
- MTY-02 fine-particle titanium oxide
- SPF value measuring instrument UV-1000S manufactured by Labsphere Conditions: Prepare three samples of transpore surge curl tape (Sumitomo 3M) with sample 2.00mg / cm2 applied, measure 10 points per sample, and delete the maximum and minimum values. An average value was calculated from eight measured values. The average value of these three samples was taken as the SPF value. The PA value was also measured under the same conditions using the same measuring device.
- Phase A Lauryl PEG-10 Tris (trimethylsiloxy) silylethyl dimethicone (Note 1) 2 parts 2) (Diphenylmethylsiloxyphenyl methicone / phenylsilsesquioxane) crosspolymer (Note 2) 1 part 3) Caprylyl methicone (Note) 3) 6 parts 4) Ethylhexyl methoxycinnamate (Note 4) 7.5 parts 5) Hexyl diethylaminohydroxybenzoyl benzoate (Note 5) 2 parts 6) Phenyl trimethicone (Note 6) 3 parts 7) Isododecane, (Dimethicone / Bisisobutyl PPG-20) Crosspolymer (Note 7) 3 parts 8) Silylated silica (Note 8) 0.3 part 9) Titanium oxide slurry prepared in Example 3, Example 4 or Comparative Example 2 15 copies Phase B 10) Butylene glyco
- the lipophilicity of the cosmetic powder can be effectively increased.
- the cosmetic powder treated with this treating agent is characterized by high lipophilicity.
- a cosmetic having the cosmetic powder has a feature of having a good tactile sensation.
- the treatment agent thus obtained can be used not only in cosmetics but also as a treatment agent widely used in various fields such as plastic additives, inks, paints, toners (magnetic powders), chemical fibers, packaging materials and the like. Is available.
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Abstract
Description
本発明化粧料用粉体の処理剤を用いた粉体処理は、湿式或いは乾式等公知の方法で行うことができる。例えば、以下の方法が挙げられる。
1.粉体と処理剤を混合したのち、ボールミル、ジェットミルなどの粉砕器を用いて、表面処理する方法。
2.処理剤を溶剤と混合し、該混合物中に粉体を分散させた後、溶剤を乾燥し、表面処理する方法。
3.目的の粉体の水系スラリー中に粉体処理剤を直接或いはエマルションの形態で添加し、表面に吸着させた後、乾燥し表面処理する方法。
反応器に下記式(2):
合成例1において式(2)のオルガノハイドロジェンシロキサンの代わりに下記式(4):
未処理の微粒子酸化チタン(堺化学工業社製STR-100N)50gにn-ヘキサン50gを加え、ディスパーで攪拌しながら、合成例1で製造した処理剤2.5gとヘキサン5gを混合した溶液を滴下した後、さらにディスパーで10分攪拌した。次に超音波洗浄機に10分かけた後、100℃で攪拌しながらn-ヘキサンを常圧除去し、さらに減圧攪拌しながら150℃で3時間焼付け処理を行ない、化粧料用粉体を得た。
実施例1~2および比較例1の酸化チタンスラリーについて、粘度をE型粘度計(トキメック社製VISCONIC EMD)で、酸化チタンスラリー粒子のメジアン径(累積分布の50%に相当する粒径、D50、μm)および、標準偏差SD(測定した粒子径分布の分布幅の目安となる値(μm)で、SD=(D84-D16)/2であり、D84は累積カーブが84%となる点の粒径(μm)を表し、D16は累積カーブが16%となる点の粒径(μm)を表す。)を動的光散乱法の粒度分析計(日機装社製MICROTRAC UPA モデル9340-UPA)で測定した。
未処理の微粒子酸化チタン(堺化学工業社製STR-100N)50gにn-ヘキサン50gを加え、ディスパーで攪拌しながら、合成例1で製造した粉体処理剤5gとヘキサン5gを混合した溶液を滴下した後、さらにディスパーで10分攪拌した。次に超音波洗浄機に10分かけた後、100℃で攪拌しながらn-ヘキサンを常圧除去し、さらに減圧攪拌しながら150℃で3時間焼付け処理を行ない、化粧料用粉体を得た。
実施例3~4及び比較例2の酸化チタンスラリーを用いて、下記処方により、サンスクリーン(W/O)クリームを作製し、SPF値(紫外線防御指数)およびPA値(UV-A防御指数)を測定した。
条件:トランスポア サージカールテープ (住友3M社製)にサンプル2.00mg/cm2を塗布したサンプルを3つ用意し、サンプル1つにつき、10箇所を測定し、最高値と最低値を削除して8つの測定値で平均値を算出した。このサンプル3つの平均値をSPF値とした。
PA値についても同じ測定機器を用いて、同条件で測定した。
相A
1)ラウリルPEG-10トリス(トリメチルシロキシ)シリルエチルジメチコン(注1) 2部
2)(ジフェニルメチルシロキシフェニルメチコン/フェニルシルセスキオキサン)クロスポリマー(注2) 1部
3)カプリリルメチコン(注3) 6部
4)メトキシケイヒ酸エチルヘキシル(注4) 7.5部
5)ジエチルアミノヒドロキシベンゾイル安息香酸ヘキシル(注5) 2部
6)フェニルトリメチコン(注6) 3部
7)イソドデカン、(ジメチコン/ビスイソブチルPPG-20)クロスポリマー(注7) 3部
8)シリル化シリカ(注8) 0.3部
9)実施例3、または、実施例4、または、比較例2で作成した酸化チタンスラリー 15部
相B
10)ブチレングリコール 7部
11)クエン酸ナトリウム 0.2部
12)塩化ナトリウム 0.5部
13)精製水 52.5部
注1:東レ・ダウコーニング社製ES-5300 Formulation Aidを使用した。
注2:東レ・ダウコーニング社製PH-1560 Glossy Fluidを使用した。
注3:東レ・ダウコーニング社製FZ-3196を使用した。
注4:BASFジャパン社製ユビナールMC80を使用した。
注5:BASFジャパン社製ユビナールA Plusを使用した。
注6:東レ・ダウコーニング社製SH556 Fluidを使用した。
注7:東レ・ダウコーニング社製EL-8050 ID Silicone Organic Elastomer Blendを使用した。
注8:東レ・ダウコーニング社製VM-2270 Aerogel Fine Particleを使用した。
1.成分1~9をディスパーで攪拌し反応物を得る。
2.成分10~13を混合し混合物を得る。
3.工程1でえられた反応物に工程2でえられた混合物を加え、乳化する。
また、下記の方法で使用感の評価も行った。専門評価パネル10名により、肌に塗布する時の伸びの良さ、乾燥後のなめらかさについて下記基準にて5段階評価し、さらにその平均点から判定した。
[評価]
5点:非常に良い
4点:良い
3点:普通
2点:あまり良くない
1点:良くない
◎:平均点4.5点以上
○:平均点3.5点以上4.5点未満
△:平均点2.5点以上3.5点未満
×:平均点2.5点未満
評価結果を表2に示した。
Claims (7)
- R3が炭素数3~18の2価のアルキレン基である請求項1に記載の処理剤。
- 請求項1又は2に記載の処理剤により表面処理されてなる化粧料用粉体。
- 粒子径が0.50μm以下であることを特徴とする、請求項3に記載の化粧料用粉体。
- 粒子径の標準偏差が0.25μm以下であることを特徴とする、請求項3又は4に記載の化粧料用粉体。
- 請求項3乃至5のいずれか1項に記載の化粧料用粉体と油剤を該化粧料用粉体100質量部に対し10~10,000質量部からなる化粧料原料。
- 請求項3乃至5のいずれか1項に記載の化粧料用粉体を配合した化粧料。
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US16/311,425 US11058610B2 (en) | 2016-06-24 | 2017-06-20 | Agent for treating powder for cosmetic, powder for cosmetic, and cosmetic formulated using said powder |
JP2018524115A JPWO2017221940A1 (ja) | 2016-06-24 | 2017-06-20 | 化粧料用粉体の処理剤、化粧料用粉体、およびこれを配合した化粧料 |
EP17815408.4A EP3476382B1 (en) | 2016-06-24 | 2017-06-20 | Agent for treating powder for cosmetic, powder for cosmetic, and cosmetic formulated using said powder |
CN201780045888.2A CN109475475A (zh) | 2016-06-24 | 2017-06-20 | 用于处理化妆品用粉末的试剂、化妆品用粉末、以及使用该粉末配制的化妆品 |
KR1020197001887A KR20190020776A (ko) | 2016-06-24 | 2017-06-20 | 화장료용 분체의 처리제, 화장료용 분체 및 이를 배합한 화장료 |
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JP2020050561A (ja) * | 2018-09-28 | 2020-04-02 | 住友大阪セメント株式会社 | 表面処理金属酸化物粒子、分散液、化粧料および表面処理金属酸化物粒子の製造方法 |
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KR102289867B1 (ko) | 2019-10-18 | 2021-08-17 | 이스트힐(주) | 화장품용 실리콘 프리 코팅 분체 및 이를 포함하는 화장품 |
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US11512237B2 (en) | 2015-11-20 | 2022-11-29 | Dow Silicones Corporation | Room temperature curable compositions |
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US11359167B2 (en) | 2017-12-21 | 2022-06-14 | Dow Silicones Corporation | Fabric-care composition comprising silicone materials |
US11986547B2 (en) | 2017-12-21 | 2024-05-21 | Dow Silicones Corporation | Cosmetic composition comprising silicone materials |
WO2020067406A1 (ja) * | 2018-09-28 | 2020-04-02 | 住友大阪セメント株式会社 | 表面処理金属酸化物粒子、分散液、組成物、化粧料および表面処理金属酸化物粒子の製造方法 |
WO2020067417A1 (ja) * | 2018-09-28 | 2020-04-02 | 住友大阪セメント株式会社 | 表面処理金属酸化物粒子、分散液、化粧料および表面処理金属酸化物粒子の製造方法 |
JP2020050561A (ja) * | 2018-09-28 | 2020-04-02 | 住友大阪セメント株式会社 | 表面処理金属酸化物粒子、分散液、化粧料および表面処理金属酸化物粒子の製造方法 |
JP7095534B2 (ja) | 2018-09-28 | 2022-07-05 | 住友大阪セメント株式会社 | 表面処理金属酸化物粒子、分散液、化粧料および表面処理金属酸化物粒子の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
JPWO2017221940A1 (ja) | 2019-04-11 |
KR20190020776A (ko) | 2019-03-04 |
EP3476382A1 (en) | 2019-05-01 |
EP3476382A4 (en) | 2020-01-01 |
EP3476382B1 (en) | 2021-01-06 |
US11058610B2 (en) | 2021-07-13 |
US20190192387A1 (en) | 2019-06-27 |
CN109475475A (zh) | 2019-03-15 |
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