WO2005112871A1 - Poudre dispersible dans l'eau pour préparation cosmétique - Google Patents

Poudre dispersible dans l'eau pour préparation cosmétique Download PDF

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Publication number
WO2005112871A1
WO2005112871A1 PCT/JP2005/009079 JP2005009079W WO2005112871A1 WO 2005112871 A1 WO2005112871 A1 WO 2005112871A1 JP 2005009079 W JP2005009079 W JP 2005009079W WO 2005112871 A1 WO2005112871 A1 WO 2005112871A1
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Prior art keywords
powder
group
formula
cosmetic
phosphorylcholine
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PCT/JP2005/009079
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English (en)
Japanese (ja)
Inventor
Kenichi Sakuma
Kazuyuki Miyazawa
Original Assignee
Shiseido Company, Ltd.
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Publication date
Application filed by Shiseido Company, Ltd. filed Critical Shiseido Company, Ltd.
Publication of WO2005112871A1 publication Critical patent/WO2005112871A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • 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
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • 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
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • 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

Definitions

  • the present invention relates to a powder for cosmetics. More specifically, the present invention relates to a cosmetic powder excellent in dispersibility in water, in which a phosphorylcholine group is directly and covalently bonded to a powder surface, and a cosmetic containing the same.
  • a polymer having a phosphorylcholine group has been studied as a biocompatible polymer, and a biocompatible material in which the polymer is coated with various bases has been developed.
  • Patent Document 1 discloses that a powder coated with a homo- or copolymer of 2-metacloyloxetyl phosphorylcholine is used as a cosmetic powder to improve moisture retention and skin adhesion. Improved cosmetics are disclosed.
  • Patent Documents 2 and 3 disclose a medical material and a separating agent coated with a polymer having a phosphorylcholine group.
  • the above-mentioned materials are mainly obtained by reacting an acrylic monomer having a hydroxyl group with 2-chloro-1,3,2-dioxaphosphorane-1-oxide, and further forming a quaternary ammonium with trimethylamine.
  • Patent Document 4 discloses a copolymer of 2-methacryloxyshethyl phosphorylcholine and ester of methacrylic acid
  • Patent Document 5 discloses a single polymer of 2-methacryloxyshethyl phosphorylcholine. Coalescence is being manufactured.
  • Patent Document 6 a powder having good dispersibility in water to form granules, or treated with a surfactant to increase dispersibility in water.
  • titanium dioxide used as a cloudy bath agent is coated with a fatty acid amino acid surfactant or a dispersing nonionic surfactant such as polyethylene glycol and a fatty acid soap.
  • a fatty acid amino acid surfactant or a dispersing nonionic surfactant such as polyethylene glycol and a fatty acid soap.
  • Patent Document 1 JP-A-7-118123
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2000-279512
  • Patent Document 3 Japanese Patent Application Laid-Open No. 2002-98676
  • Patent Document 4 JP-A-9 3132
  • Patent Document 5 JP-A-10-298240
  • Patent Document 6 JP-A-7-196435
  • Patent Document 7 Japanese Patent Publication No. 7-17494
  • Patent Document 8 JP-A-3-294220
  • Patent Document 9 JP-A-11-148027
  • Patent Document 10 JP-A-2000-0444829
  • the above-mentioned method for improving the dispersibility of a powder is required only for a cosmetic powder that can only be applied in a limited variety of powders, and is stable over time in water. It was not a method to keep the dispersibility of the whole.
  • the present invention has been made in view of the above-mentioned problems, and has a phosphorylcholine group directly and covalently bonded to a powder surface to form a cosmetic powder excellent in dispersibility in water, and to blend the same.
  • the purpose of the present invention is to provide an improved cosmetic.
  • the present invention provides a water-dispersible cosmetic powder characterized in that a phosphorylcholine group represented by the following formula (1) is directly covalently bonded to the powder surface. is there.
  • the present invention also provides the above-mentioned cosmetic powder, wherein the powder is a powder having a hydroxyl group on the surface.
  • the present invention provides a method of introducing an amino group directly into the surface of a powder, and then reacting a compound containing an aldehyde compound obtained by oxidative cleavage of glycerol phosphorylcholine with the amino group.
  • the present invention also provides a method for producing the above cosmetic powder.
  • the present invention provides a method for introducing an amino group directly into the surface of a powder, and then adding a carboxyl-containing compound obtained by an oxidative cleavage reaction of phosphorylcholine of glycerol to the amino group. It is intended to provide a method for producing the above powder for cosmetics, characterized by reacting.
  • the present invention provides the above cosmetic powder, which is obtained by directly reacting a compound represented by the following formula (2) and Z or (3) on the powder surface. It provides a method for producing a body.
  • n is 1-4.
  • X, X and X each independently represent a methoxy group
  • the present invention provides a cosmetic comprising the above-mentioned water-dispersible cosmetic powder.
  • the cosmetic powder of the present invention is a powder having an excellent effect of dispersibility in water, and is a powder used exclusively as a compounding material for cosmetics. In particular, it is extremely useful as a highly dispersible powder and as a raw material for cosmetics containing various powders.
  • the cosmetic powder of the present invention does not lose the phosphorylcholine group due to peeling of the polymer as compared with a powder having a phosphorylcholine group introduced by being coated with a polymer having a phosphorylcholine group.
  • since it is not coated with a polymer it has the advantage that it does not kill any surface characteristics of the powder itself. For example, it is possible to coat the surface with a phosphorylcholine group without filling the three-dimensional microstructure (micropores, etc.) of the powder surface of several nm.
  • the cosmetic powder of the present invention has an effect of preventing adsorption and denaturation by preventing adsorption to powder when there is a compounding material such as protein or lipid to be dispersed in the cosmetic. Also have. According to the production method of the present invention, it is possible to impart a desired arbitrary amount of a phosphorylcholine group to the surface of various cosmetic powders to be blended with the cosmetic by a simple reaction. is there. As a result, a cosmetic modified powder having a desired function by the phosphorylcholine group can be easily provided.
  • FIG. 1 shows the structural formula and NMR ⁇ vector of Synthesis Example 1.
  • FIG. 2 shows the structural formula and NMR ⁇ vector of Synthesis Example 3.
  • the phosphorylcholine group of the formula (1) is directly and covalently bonded to the cosmetic powder surface.
  • an arbitrary spacer may be inserted between the functional group and the phosphorylcholine group.
  • the powder is not limited as long as it is used for cosmetics!
  • the powder used is not particularly limited.
  • the powder generally means any object having an average particle diameter of 0.01 to about LOO m.
  • Specific powders include, for example, inorganic powders (e.g., talc, kaolin, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, rhombic mica, biotite, permikilite, magnesium carbonate) , Calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (calcium sulfate), calcium phosphate
  • Organic powder for example, polyamide resin powder (eg, polyamide resin powder), fluorine apatite, hydroxyapatite, ceramic powder, metal stone (eg, zinc myristate, calcium palmitate, aluminum stearate), boron nitride, cerium oxide, etc.); Nylon powder
  • a powder having a hydroxyl group on the surface is preferable.
  • the powders preferably used are silica, talc, carion, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, mica, biotite, lithia mica, permikulite, magnesium carbonate, carbonate Calcium, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, zeolite, barium sulfate, calcium sulfate (calcium sulfate), calcium phosphate, fluoroapatite, hydroxy Apatite, ceramic powder, pigment powder for cosmetics such as boron nitride, white pigment for cosmetics such as titanium dioxide and zinc oxide, iron oxide (bengara), iron titanate, y iron monoxide, yellow iron oxide, Loess, black iron oxide, carbon black, lower titanium oxide, mango violet, cobalt bar Colored pigments
  • step 1 is omitted.
  • Step 1 An amino group is introduced into any cosmetic powder by a known method or a method to be developed in the future. Amino groups are introduced directly on the powder surface. Direct means that the method of coating with a polymer having an amino group is not included.
  • the amino group is a primary amine or a secondary amine.
  • Step 2 An aldehyde compound, a hydrate compound, or a carboxy compound obtained by an oxidative cleavage reaction of glycerol phosphorylcholine with a powder having an amino group is converted to a carboxy compound by a reduction amination reaction or an amide compound.
  • phosphorylcholine groups are directly added to the cosmetic powder surface.
  • the phosphorylcholine group can be directly added to the powder surface of the cosmetic cosmetic powder by hydroxyl group and esterification of the surface. It is.
  • Step 1 Known methods (Step 1) for introducing an amino group or a hydroxyl group into these powders include the following.
  • Amino groups are introduced into the powder surface by low-temperature plasma in a nitrogen gas atmosphere.
  • the powder is stored in a plasma reactor, the inside of the reactor is evacuated by a vacuum pump, and nitrogen gas is introduced.
  • amino groups can be introduced into the powder surface by glow discharge.
  • the powder is subjected to a plasma reaction. After the reaction vessel is housed in a vessel and the inside of the reaction vessel is evacuated with a vacuum pump, oxygen gas or oxygen gas or hydrogen gas is introduced. Subsequently, by a glow discharge, it is also possible to mechanically powder the plasma-treated powder capable of introducing hydroxyl groups to the powder surface.
  • the literature on plasma processing is shown below.
  • Plasma aminofunctionalisation of PVDr microfiltration membranes comparison of the in plasma modifications with a grafting method using ESCA and an
  • the surface of a hydroxyl group-containing cosmetic powder is treated with a surface modifier such as alkoxysilane, chlorosilane, and silazane having an amino group.
  • silicon dioxide is treated with 3-aminopropyltrimethoxysilane having a primary amino group to introduce an amino group.
  • the silica is immersed in a mixed solution of water and 2-propanol, and after adding 3-aminopropyltrimethoxysilane, the mixture is heated to 100 ° C. and reacted for 6 hours. After cooling to room temperature, the silica is washed with methanol and dried to obtain a silica powder having amino groups introduced directly to the silica surface.
  • Powders preferably used in the present method include silica, talc, carion, mica, sericite, sericite, phlogopite, synthetic mica, rhodolite, biotite, lithia mica, permichulite, and magnesium carbonate.
  • For cosmetics such as shim, magnesium silicate, strontium silicate, metal tungstate, magnesium, zeolite, barium sulfate, calcined calcium sulfate (baked gypsum), calcium phosphate, fluoroapatite, hydroxyapatite, ceramic powder, boron nitride, etc.
  • Pigment powders white pigments for cosmetics such as titanium dioxide and zinc oxide, iron oxide (iron oxide), iron titanate, iron monoxide, yellow iron oxide, loess, black iron oxide, carbon black, low-order titanium oxide Tan, Mango Violet, Cobalt Violet, Chromium Oxide, Chromium Hydroxide, Cobalt Titanate, Ultramarine Blue, Navy Blue, etc., Color Pigments, Titanium Oxide Titanium Coated My Strength, Titanium Oxide Coats , Colored oxidized titanium coated my power, bismuth oxychloride Metal pigments such as pearl pigments such as aluminum powder and kappa powder.
  • Step 2 a method of introducing a phosphorylcholine group to the surface of the aminated powder will be described below.
  • the cosmetic powder obtained in step 1 is immersed in methanol, and phosphatidylglyceraldehyde is added, and left at room temperature for 6 hours. Then, sodium cyanoboronate is added at 0 ° C., and the mixture is heated and stirred overnight to add a phosphorylcholine group to the amino group. The cosmetic powder is washed with methanol and then dried to obtain a cosmetic powder having phosphorylcholine groups directly on the surface.
  • a reaction solvent other than methanol, a protic solvent such as water, ethanol, or 2-propanol can be used, but the introduction ratio when methanol is used tends to be high.
  • the cosmetic powder obtained in step 1 may be added to a carboxylic acid salt produced by reacting a carboxyl compound having a phosphorylcholine group with salt salt in acetonitrile for a certain period of time. The mixture is stirred at room temperature for 6 hours to add a phosphorylcholine group to the amino group.
  • a scheme of a method of introducing a phosphorylcholine group using 3-aminopropyltrimethoxysilane as a surface modifier is shown below using silica as an example.
  • a cosmetic powder having an amino group is prepared, and the phosphorylcholine is subjected to a reductive amination reaction with an aldehyde compound or a hydrate compound obtained by an oxidative cleavage reaction of glycerol phosphorylcholine.
  • the powder for cosmetics of the present invention can be easily obtained and the surface of various powders for cosmetics can be obtained. There is a great advantage that can be modified.
  • a cosmetic powder having an amino group is prepared, and the phosphorylcholine group is similarly converted into a cosmetic powder by an amidation reaction with a carboxyl compound obtained by an oxidative cleavage reaction of glycerol phosphorylcholine. It is also possible to produce a cosmetic powder directly applied to the surface.
  • the glycerol is obtained by an oxidative cleavage reaction of phosphorylcholine.
  • the compound containing an aldehyde compound is a compound that causes a known glycerol phosphorylcholine group to undergo an oxidative cleavage by a known method, and is an extremely simple step.
  • the bond is cleaved by acidifying 1,2-diol with periodate or periodate to obtain an aldehyde compound.
  • the reaction is usually performed in water or an organic solvent containing water.
  • the reaction temperature is 0 ° C and room temperature.
  • Aldehydes may form hydrates through equilibrium reactions in water, but do not affect subsequent reactions with amines.
  • An example of a scheme for preparing a monofunctional aldehyde having a phosphorylcholine group is shown below.
  • a phosphorylcholine derivative represented by the following formula (4) is dissolved in distilled water.
  • the phosphorylcholine derivative of the following formula (4) is a known compound and can be obtained as a commercial product.
  • a phosphorylcholine derivative represented by the following formula (4) is dissolved in distilled water.
  • the phosphorylcholine derivative of the following formula (4) is a known compound and can be obtained as a commercial product.
  • the water-dispersible cosmetic powder of the present invention is blended with any cosmetic.
  • Cosmetic is not limited, but it can be blended especially with ozw emulsified cosmetics, lotions, and other products that have a process of highly dispersing powder in water or products that have a process of highly dispersing powder in the manufacturing process. Like That's right.
  • the compounding amount is appropriately determined depending on the kind and purpose of the cosmetic, and is not particularly limited, but is usually in the range of about 0.1 to 95% by mass based on the total amount of the cosmetic.
  • 0.1 for powder two-layer lotion 1% for L0 mass%, O / W emulsified foundation, powder-containing cream, and O / W emulsified sunscreen 50 mass 0/0, powdery foundation, the amount of 10 to 95 weight 0/0 for a stick foundation sometimes good preferable.
  • the cosmetic of the present invention is produced by blending, in addition to the water-in-highly dispersible cosmetic powder, other components usually used in cosmetics.
  • ordinary powder components liquid fats and oils, solid fats and oils, waxes, hydrocarbon oils, higher fatty acids, higher alcohols, ester oils, silicone oils, anionic surfactants, cationic surfactants, amphoteric surfactants, non- Ionic surfactants, humectants, water-soluble polymers, thickeners, filming agents, UV absorbers, sequestering agents, lower alcohols, polyhydric alcohols, sugars, amino acids, organic amines, polymer emulsions, pH A regulator, a skin nutritional agent, a vitamin, an antioxidant, an antioxidant aid, a fragrance, water and the like can be appropriately blended as required, and can be produced by a conventional method according to a desired dosage form.
  • the present invention will be described in more detail based on examples. Note that the present invention is not limited to these examples. Unless otherwise specified, the compounding amount is mass% based on the total amount.
  • FIG. 1 shows the 1H NMR spectrum of the compound of the formula (5).
  • a methanol solution containing 7.5 g of the compound of Synthesis Example 1 is dissolved in 30 mL of dehydrated methanol, and the atmosphere in the vessel is replaced with dry nitrogen.
  • 5.4 g of 3-aminopropyltrimethoxysilane was added to a methanol solution of the compound 1.
  • 2.5 g of sodium cyanohydroborohydride was added, and the mixture was returned to room temperature and stirred for 16 hours.
  • dry nitrogen was kept flowing through the reaction vessel.
  • FIG. 2 shows the 1H-NMR of the compound of the formula (8).
  • Example 1 Introducing an amino group directly into the powder surface, and then reacting a compound containing an aldehyde compound obtained by an oxidative cleavage reaction of glycerol phosphorylcholine with the amino group Production Method for Underwater Highly Dispersible Cosmetic Powder: Two-Step Production Method "
  • A) a powder for cosmetics of the present invention comprising a fine particle zinc oxide powder having phosphorylcholine groups directly on the surface thereof.
  • Example 2 Method for producing water-dispersible cosmetic powder by reacting compound represented by formula (2) directly on powder surface: one-step production method
  • the powder for cosmetics of the present invention was significantly modified by being directly modified with the phosphorylcholine group of the formula (1), whereby the dispersion stability in water was greatly improved.
  • Example 3 Introducing an amino group directly to the powder surface, and then reacting a compound containing a carboxyl compound obtained by an oxidative cleavage reaction of glycerol phosphorylcholine with the amino group.
  • Production method of water-based highly dispersible cosmetic powder two-stage production method ''
  • fine particle titanium dioxide particle size: 0.02 to 0.05 m
  • the mixture was heated to 80 ° C and boiled under reflux for 5 hours.
  • the fine titanium dioxide powder was filtered three times with 100 mL of methanol, washed, and dried under reduced pressure to obtain fine titanium dioxide powder into which an aminopropyl group was introduced.
  • Example 4 Production method of water-dispersible cosmetic powder by reacting compound represented by formula (7) directly on powder surface: one-step production method
  • the cosmetic powder of the present invention was significantly modified in water by greatly improving the dispersion stability in water by directly modifying the powder with the phosphorylcholine group of the formula (1).
  • Example 5 the powder into which the phosphorylcholine group of the formula (1) was introduced was changed to silica (Example 5), sericite (Example 6), myriki (Example 7), and talc (Example Example 8), changed to kaolin (Example 9), red iron oxide (Example 10), yellow iron oxide (Example 11), black iron oxide (Example 12)
  • silica Example 5
  • sericite Example 6
  • myriki Example 7
  • talc Example 8
  • kaolin Example 9
  • red iron oxide Example 10
  • yellow iron oxide Example 11
  • black iron oxide Example 12
  • Example 15 the powder into which the phosphorylcholine group of the formula (1) was introduced was changed to silica (Example 13), sericite (Example 14), myriki (Example 15), and talc (Example 15).
  • a phosphorylcholine group modification reaction was carried out by changing to Example 16), kaolin (Example 17), red iron oxide (Example 18), yellow iron oxide (Example 19), and black iron oxide (Example 20). It has been found that the phosphorylcholine group of the formula (1) can be directly covalently introduced into the powder surface by any of the methods of the present invention.
  • the shampoo containing the powder modified with the phosphorylcholine group had excellent stability in powder dispersibility with time and excellent usability.
  • the shampoo containing the powder modified with the phosphorylcholine group had excellent stability in powder dispersibility with time and excellent usability.
  • the iDani cosmetic product containing the phosphorylcholine group-modified powder had good re-dispersibility of the powder layer and excellent usability.
  • the cosmetic powder of the present invention is excellent in water dispersibility, and is therefore preferably used for powder-containing cosmetics having excellent powder dispersion stability.

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Abstract

Il est divulgué une poudre hydrodispersable pour des préparations cosmétiques qui est caractérisée en ce qu'un groupe de phosphorylcholine représenté par la formule (1) ci-aprés est directement liée par covalence à une surface de poudre. Il est également divulgué une préparation cosmétique dans laquelle est mélangée une telle poudre hydrodispersable. Par conséquent, il peut être obtenu une préparation cosmétique dans laquelle une poudre pour préparations cosmétiques ayant une hydrodispersibilité excellente est mélangée de maniére stable.
PCT/JP2005/009079 2004-05-24 2005-05-18 Poudre dispersible dans l'eau pour préparation cosmétique WO2005112871A1 (fr)

Applications Claiming Priority (4)

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JP2004-152676 2004-05-24
JP2004152676 2004-05-24
JP2005-136838 2005-05-10
JP2005136838A JP3852942B2 (ja) 2004-05-24 2005-05-10 水中分散性化粧料用粉体

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1690867A4 (fr) * 2003-12-02 2009-08-12 Shiseido Co Ltd Compose contenant un groupe phosphorylcholine et agent de modification de surface constitue dudit compose
CN112386504A (zh) * 2019-08-16 2021-02-23 信越化学工业株式会社 分散性粉体及化妆品

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CN101977968B (zh) * 2008-03-31 2013-03-13 株式会社资生堂 聚硅氧烷、丙烯酸系化合物及乙烯系化合物
JP5448529B2 (ja) * 2008-03-31 2014-03-19 株式会社 資生堂 ポリシロキサン及びその製造方法
JP5089521B2 (ja) * 2008-07-31 2012-12-05 学校法人 中村産業学園 粉体のプラズマ処理方法
CN103282368B (zh) 2010-12-24 2015-04-08 日油株式会社 含有氨基的磷酰胆碱化合物及其制备方法
KR101915973B1 (ko) * 2011-10-31 2018-11-07 (주)아모레퍼시픽 자외선 차단용 유무기 복합분체 및 이를 함유하는 화장료 조성물
JPWO2023026999A1 (fr) * 2021-08-25 2023-03-02

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JPS61500918A (ja) * 1984-01-20 1986-05-08 バイオコンパテイブルズ・リミテツド 生物適合性表面に関する改良
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JPH11222421A (ja) * 1998-01-31 1999-08-17 Naris Cosmetics Co Ltd 紫外線防御剤及び紫外線防御剤の製造方法並びに化粧料
JP2003040942A (ja) * 2001-05-22 2003-02-13 Shiseido Co Ltd ホスホリルコリン基含有重合体及びその製造方法
WO2004048492A1 (fr) * 2002-11-25 2004-06-10 Shiseido Company, Ltd. Procede de modification d'une surface d'un materiau
JP2005187456A (ja) * 2003-12-02 2005-07-14 Shiseido Co Ltd ホスホリルコリン基含有化合物及び該化合物からなる表面改質剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1690867A4 (fr) * 2003-12-02 2009-08-12 Shiseido Co Ltd Compose contenant un groupe phosphorylcholine et agent de modification de surface constitue dudit compose
US7906670B2 (en) 2003-12-02 2011-03-15 Shiseido Co., Ltd. Phosphorylcholine group containing compound and surface modifying agent composed of such compound
CN112386504A (zh) * 2019-08-16 2021-02-23 信越化学工业株式会社 分散性粉体及化妆品

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