WO2014069403A1 - 油中水型乳化組成物 - Google Patents
油中水型乳化組成物 Download PDFInfo
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- WO2014069403A1 WO2014069403A1 PCT/JP2013/079138 JP2013079138W WO2014069403A1 WO 2014069403 A1 WO2014069403 A1 WO 2014069403A1 JP 2013079138 W JP2013079138 W JP 2013079138W WO 2014069403 A1 WO2014069403 A1 WO 2014069403A1
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- AZPFEYANVWPOHJ-CLFAGFIQSA-N [2-hydroxy-3-[2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropoxy]propyl] (Z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)COCC(O)COC(=O)CCCCCCC\C=C/CCCCCCCC AZPFEYANVWPOHJ-CLFAGFIQSA-N 0.000 description 1
- BKZCZANSHGDPSH-KTKRTIGZSA-N [3-(2,3-dihydroxypropoxy)-2-hydroxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)COCC(O)CO BKZCZANSHGDPSH-KTKRTIGZSA-N 0.000 description 1
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- NPTLAYTZMHJJDP-KTKRTIGZSA-N [3-[3-[3-[3-[3-[3-[3-[3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)CO NPTLAYTZMHJJDP-KTKRTIGZSA-N 0.000 description 1
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- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 description 1
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- GFAZGHREJPXDMH-UHFFFAOYSA-N glyceryl dipalmitate Natural products CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 description 1
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- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
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- YZUUTMGDONTGTN-UHFFFAOYSA-N nonaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCO YZUUTMGDONTGTN-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 229940032094 squalane Drugs 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LINXHFKHZLOLEI-UHFFFAOYSA-N trimethyl-[phenyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=CC=CC=C1 LINXHFKHZLOLEI-UHFFFAOYSA-N 0.000 description 1
- PVQUEUNCRLSHJP-UHFFFAOYSA-N trimethylsilyl undecanoate Chemical compound CCCCCCCCCCC(=O)O[Si](C)(C)C PVQUEUNCRLSHJP-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
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Images
Classifications
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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Definitions
- the present invention relates to a water-in-oil type emulsified composition, and particularly to improvement of the feeling of use.
- water-in-oil emulsion compositions that are widely used as a base for cosmetics and the like increase the amount of water, and the fresh feeling of use increases, and the internal water phase ratio increases. Viscosity increases and tends to stabilize as a composition.
- it is not easy to incorporate a large amount of water into the water-in-oil emulsion composition and it is also known that a formulation in order to do so is necessary.
- various oil agents such as ester oils, silicone oils, hydrocarbon oils and the like are used in the water-in-oil emulsion composition depending on the desired effect, but generally these oil agents have different properties.
- silicone oil not only brings gloss to the skin as an oil agent, but is not compatible with the oil agent, but rather is combined with an oil agent having a property of exerting its effect by being in close contact with the skin, so that it is applied to the surface of the coating film.
- an advantageous property in cosmetics and the like that exudes and forms a film and improves the durability of the film (for example, Patent Document 1)
- Patent Document 1 because of the combination of special oils, Providing these as a gel-like (cream-like) stable water-in-oil emulsion composition has not been realized.
- the present invention has been made in view of the prior art, and provides a water-in-oil emulsified composition that has high stability as a preparation, provides a fresh feel and a glossy finish, and is excellent in makeup. The purpose is to do.
- the present inventors have obtained an emulsion composition of water containing an oil component containing a specific oil agent and a silicone oil under the formulation of zinc decyltrisiloxanecarboxylate, and water. It has been found that it has a high stability as a preparation, gives a fresh feel to use and has a glossy finish, and also has a long-lasting makeup due to the exudation of silicone oil, thereby completing the present invention.
- the emulsion composition according to the present invention is (A) a polyhydric alcohol fatty acid ester and / or a hydrocarbon of 1 to 20% by mass; (B) 3-20% by weight of a transparent nonvolatile silicone oil that separates when mixed with the component (a) at 25 ° C .; (C) zinc decyltrisiloxanecarboxylate 0.1 to 5% by mass; (D) water, It is characterized by including.
- the component (a) includes polyglyceryl triisostearate having 1 to 4 isostearic acid residues and monoisostearin having 4 to 10 moles of glycerin added and 1 to 4 isostearic acid residues. It is preferred to be selected from glyceryl acid, pentaerythritol fatty acid ester, isostearyl glyceryl ether.
- the water-in-oil emulsion composition preferably further includes a silicone surfactant having an HLB value of 7 or less.
- the cosmetic according to the present invention is characterized by including the water-in-oil emulsion composition.
- the makeup method according to the present invention comprises: (I) applying a first agent containing a polyhydric alcohol fatty acid ester and / or hydrocarbon and water; (II) A second non-volatile silicone oil that separates when mixed with the component (a) at 25 ° C. after the step (I) and zinc decyltrisiloxanecarboxylate on the coated surface. Applying the agent; It is characterized by including.
- the emulsion composition according to the present invention comprises (a) a polyhydric alcohol fatty acid ester and / or hydrocarbon, (b) a transparent nonvolatile silicone oil that separates when mixed with the component (a) at 25 ° C., (C) zinc decyltrisiloxanecarboxylate and (d) water.
- Component (a) is a polyhydric alcohol fatty acid ester and / or hydrocarbon, and an oil component that separates without dissolving when mixed with component (b) at room temperature (25 ° C.). is there.
- the component (a) encloses a coloring material at the time of application to become a close-contact oil component, and quickly separates from the component (b) that is an exudation oil component. Therefore, it is preferable that the component (a) is more excellent in dispersibility of coloring materials and the like than the component (b), has high affinity with the skin, and easily adheres to the skin.
- polyhydric alcohol fatty acid esters examples include glyceryl monopalmitate, glyceryl monostearate, glyceryl monoisostearate, glyceryl monooleate, glyceryl monolinoleate, glyceryl monobehenate, glyceryl monolaurate, glyceryl dipalmitate
- Glyceryl fatty acid esters such as glyceryl distearate, glyceryl dioleate, glyceryl dilinoleate, glyceryl dibehenate, glyceryl tristearate, glyceryl trioleate; diglyceryl monostearate, diglyceryl monooleate, diglyceryl dioleate, mono Diglyceryl isostearate, polyglyceryl triisostearate, tetraglyceryl monostearate, tetraglyceryl monooleate , Tetraglyceryl tristearate, tetraglyce
- the number of moles of glycerin added as polyhydric alcohol is 4 to 10 and the number of isostearic acid residues as fatty acid is 1 to 4.
- the use of polyglyceryl isostearate, glyceryl monoisostearate, pentaerythritol fatty acid ester, isostearyl glyceryl ether is preferred.
- the polyglyceryl isostearate is obtained by adding isostearic acid to polyglycerin having an average addition mole number of 4 to 10 without specifying the location, and is preferably a polyglycerol having an average addition mole number of 5. Further, isostearic acid is preferably added with 2 to 4, particularly 3 with respect to one molecule. Therefore, in the present invention, it is particularly preferable to use polyglyceryl-5 triisostearate.
- Polyglyceryl isostearate can be provided by various known synthesis methods, but those having a narrow distribution of the number of moles of glycerin added and those having a small number of cyclic substances as impurities are preferable.
- Such polyglyceryl isostearate is disclosed in, for example, Japanese Patent No. 34877881 and Japanese Patent Application Laid-Open No. 2006-111539 (polyglycerin having a hydroxyl group of 1200 or less and a primary hydroxyl group of 50% or more of all hydroxyl groups and a fatty acid esterified. Manufactured polyglycerin fatty acid ester).
- pentaerythritol fatty acid ester tetra (behenic acid / benzoic acid / ethylhexanoic acid) pentaerythrityl and hexahydroxystearic acid dipentaerythrityl are particularly preferable.
- these commercially available products include “Saracos P-B822” (manufactured by Nisshin Oillio Group Co., Ltd.) and “Cosmol 168M” (manufactured by Nisshin Oillio Group Co., Ltd.), and these can be suitably used. it can.
- hydrocarbons examples include liquid paraffin, heavy liquid isoparaffin, liquid isoparaffin, polybutene, hydrogenated polybutene, hydrogenated polyisobutene, hydrogenated polydecene, tetradecene, isohexadecane, isododecane, squalane, squalene, pristane, ⁇ -olefin.
- examples thereof include semi-solid to liquid oils at room temperature (25 ° C.) such as oligomers and petrolatum, and liquid paraffin and hydrogenated polyisobutene are particularly preferred.
- the blending amount of the component (a) is 1 to 20% by mass, preferably 2 to 15% by mass with respect to the total amount of the emulsified composition.
- the blending amount of the component (a) is too large or too small, it may be inferior to a fresh feeling of use and a glossy finish, and when it is too large, stickiness tends to occur after application.
- Component (b) is a transparent, non-volatile silicone oil at 25 ° C. that separates without dissolving when mixed with component (a) at room temperature (25 ° C.). After the composition is applied to the skin and the like, it is separated from the component (a) to form a surface layer, and is a component that particularly improves makeup.
- the component (b) preferably exhibits a liquid state with a viscosity at 25 ° C. of 500 mPa ⁇ s or less as measured by a B-type viscometer.
- silicone oil of the component (b) examples include dimethylpolysiloxane; methylhydrogenpolysiloxane; methylphenylsilicone such as trimethylpentaphenyltrisiloxane, diphenyldimethicone, diphenylsiloxyphenyltrimethicone, phenyltrimethicone, phenyldimethicone; And perfluorooctylethyl / diphenyldimethicone.
- These silicone oils can be used singly or in combination of two or more depending on the form of use of the water-in-oil emulsion composition of the present invention.
- dimethylpolysiloxane when used for a foundation or the like, dimethylpolysiloxane When used for lipsticks, etc., it is preferable to use diphenyldimethicone or trimethylpentaphenyltrisiloxane.
- the amount of component (b) is 3 to 20% by mass, preferably 5 to 15% by mass, based on the emulsion composition.
- the blending amount of the component (b) is less than 3% by mass, the glossy finish is not achieved and the durability of the coating film is also reduced.
- the component (b) exceeds 20% by mass, the stability of the composition tends to decrease.
- the component is zinc decyltrisiloxane carboxylate which is a metal salt (metal soap) of carboxy-modified silicone.
- the acquisition method of the decyl trisiloxane carboxylate zinc used for this invention is not specifically limited, As the synthesis method, for example, (A) a composition containing a compound represented by the following general formula (I); (In the above formula, M is a hydrogen atom or a monovalent metal atom.) (B) an aqueous solution containing zinc ions (Zn 2+ ); (C) an aqueous solution containing hydroxide ions; May be mixed.
- M is a hydrogen atom or a monovalent metal atom.
- monovalent metal atoms include Li, Na, and K.
- the component (A) is prepared by combining a known synthesis method, for example, 1,1,1,3,5,5,5-heptamethyltrisiloxane and a trimethylsilyl derivative having a vinyl terminal with a platinum-based catalyst. It is obtained by a step of deprotecting by alcoholysis by adding an addition reaction below and heating at least 1 mol or more of a monohydric alcohol, water or a mixture thereof per 1 mol of a trimethylsilyl group as a protecting group, Moreover, you may use a commercial item.
- component (B) examples include aqueous solutions of zinc chloride, zinc sulfate, zinc nitrate, zinc phosphate, zinc hydroxide, etc.
- component (C) includes sodium hydroxide, potassium hydroxide, calcium hydroxide. , Magnesium hydroxide, barium hydroxide, zinc hydroxide, aluminum hydroxide, iron hydroxide, copper hydroxide and the like.
- the material, the Compound A-derived moieties - If abbreviated to as an average composition formula "R Si -C 10 H 20 -COO" R Si -C 10 H 20 -COO "- (Zn 2+) 5 / 8 (OH ⁇ ) 1/4 ”.
- the neutralization reaction formula is as follows. 8R Si —C 10 H 20 —COONa + 5ZnSO 4 + 2NaOH ⁇ 3Zn (O—C ( ⁇ O) —C 10 H 20 —R Si ) 2 +2 (R Si —C 10 H 20 — (C ⁇ O) —O—Zn —OH) + 5Na 2 SO 4
- the blending amount of the component (c) is 0.1 to 5% by mass, preferably 0.5 to 3% by mass with respect to the emulsion composition.
- the component (c) is less than 0.1% by mass, the stability of the composition is insufficient, and when it exceeds 5% by mass, the use feeling and finish effect of the composition may be lowered.
- the water which is a component (d) is a component which comprises the inner water phase of a water-in-oil composition, and can contain the aqueous component which can be mix
- the amount of water is not particularly limited as long as it does not impair the effects of the present invention, but when it is a gel-like (cream-like) composition excellent in freshness, the internal water phase ratio is 40% by mass with respect to the composition. % Or more, more preferably 40 to 90% by mass, particularly preferably 45 to 90% by mass.
- the blending amount corresponds to the blending amount of the entire inner aqueous phase composed of water and an arbitrary aqueous component.
- a silicone surfactant as an emulsifier, particularly dimethylpolysiloxane having a polyoxyalkylene group or a polyglycerin group introduced therein.
- the emulsifier has an HLB (Hydrophile-Lipophile Balance) value of 7 or less.
- silicone surfactants examples include PEG-3 dimethicone, PEG-9 methyl ether dimethicone, PEG-10 dimethicone, PEG-9 polydimethylsiloxyethyl dimethicone, lauryl PEG-9 polydimethylsiloxyethyl dimethicone, PEG / PPG-20 / 22 butyl ether dimethicone, polyglyceryl-3 disiloxane dimethicone, polyglyceryl-3 polydimethylsiloxyethyl dimethicone, lauryl polyglyceryl-3 polydimethylsiloxyethyl dimethicone and the like.
- PEG-10 dimethicone lauryl PEG-9 polydimethylsiloxyethyl dimethicone, more preferably PEG-10 dimethicone.
- the amount of the emulsifier is not particularly limited, but generally it is preferably about 0.05 to 1.0% by mass.
- the water-in-oil emulsion composition of the present invention When the water-in-oil emulsion composition of the present invention is applied to the skin or the like at room temperature (25 ° C.), the two incompatible oil components (a) and (b) are separated, By forming the surface layer (transparent phase) and the adhesive layer, the glossy finish as an oil agent is exhibited, and the durability of the coating film, that is, the makeup feeling is improved.
- each of the oil agents needs to be uniformly dispersed in the composition and maintained as a single unit until it is applied.
- the emulsion of the present invention can provide a fresh feeling in use upon application by blending water as the component (d) together with the effect of the oil, but the oils (a) and (b ) Component and (d) component are simply emulsified, the high fluidity of water hinders stable dispersion of the two oils and separates them in the composition. Therefore, the present inventors use decyltrisiloxane carboxanzinc, which is the component (c), in order to keep the above two kinds of oil and water stably and uniformly dispersed in the composition. It was decided.
- FIG. 1 is a schematic diagram showing the presence of components (a) to (d) in the emulsified composition of the present invention.
- the decyltrisiloxane carboxanzinc as component (c) was converted into water or component (a) (polyglyceryl triisostearate in FIG. ), And a system in which these are dispersed as emulsion particles in the continuous phase of component (b) is induced (FIG. 1 (A)).
- the emulsified particles (component (d) and the lamellae of component (d) and component (a)) incorporated in component (c) are densely packed in the continuous phase and are physically almost all. Because it does not move, separation and unity are unlikely to occur. Therefore, the emulsified composition of the present invention apparently exhibits a stable uniform monolayer appearance having a gel property that does not flow.
- FIG. 1B shows a state in which water as component (d) is volatilized from the structure of FIG.
- the emulsified particles containing the component (a) can move and fluidity occurs in the composition.
- the components (a) and (b) that are not originally compatible with each other start to be separated to form the above-mentioned adhesion layer and surface layer.
- (c) component which took in water moves to a surface layer with (b) component after volatilization of water.
- FIG. 2 shows the change of the composition after applying the emulsion composition of the present invention to the skin.
- FIG. 2 (A) shows a state when the emulsified composition of the present invention is placed on the skin 10 and shows the composition itself before application.
- the components (a) to (d) constitute the uniform layer 11 as shown in FIG. 1 (A).
- FIG. 2 (B) shows a state where the composition is being applied onto the skin. From the component (a) 12 that adheres to the skin, the composition disperses / disintegrates due to shear (shear) when applied to the skin (spreads), and the emulsion particles disperse / disintegrate. , (B) component and (c) component 13 are separated and ooze out to the surface.
- FIG. 2C shows a state after the composition is applied onto the skin, and the component (a), the component (b) and the component (c) are completely separated, and the adhesion layer 14 and A two-layer structure of the transparent layer 15 is formed.
- the transparent layer 15 mainly composed of the component (b) brings about a glossy finish as an oil agent, and contributes to improving the makeup as a surface film by being fixed to the component (c).
- the component (a) also exhibits an effect such as gloss as an oil agent.
- the color material is applied to the adhesion layer 14 covered with the transparent layer 15. It will stay. Therefore, when a coloring material is blended with the composition of the present invention, color transfer is unlikely to occur even when the coated surface is touched.
- the transparent layer 15 on the surface promotes the diffusion of light, it is possible to impart a transparent feeling like bare skin to the coated surface when used for a foundation or the like.
- the transparent layer 15 on the surface promotes the diffusion of light, it is possible to impart a transparent feeling like bare skin to the coated surface when used for a foundation or the like.
- the method for producing the emulsified composition of the present invention is not particularly limited, but from the viewpoint of making a preparation having stability, a uniform monolayer composition in which the components (a) and (b) are not separated in the composition. It is preferable to manufacture so that it becomes.
- the components (a) to (c) are mixed under heating at 90 ° C. or higher, and the component (d) heated to 90 ° C. or higher is added to the mixture with stirring to emulsify.
- the composition may be cooled as necessary to form a uniform emulsion composition.
- the present invention includes oils and waxes other than those described above, surfactants, coloring materials, powders, polymer compounds, moisturizers, fragrances, antioxidants, preservatives, cosmetic ingredients, etc. Ingredients usually used in cosmetics, skin external preparations and the like can be appropriately blended within a range not impairing the effects of the present invention.
- the water-in-oil emulsified composition according to the present invention can be used as a base in a wide range of applications such as cosmetics and external preparations for skin, but exhibits a feeling of use particularly suitable as a cosmetic.
- application to cosmetics applied to the outer skin is preferable, for example, whitening serum, milk, cream, pack, foundation, makeup base, lipstick, lip gloss, eye shadow, eyeliner, mascara, dyeing.
- Use as hair, hair treatment, hair foam, hair pack and the like can be mentioned, and use as a foundation is particularly preferable.
- the components (a) to (d) are used as one emulsified composition containing all of the components (a) to (d) as described above. You may prepare and use separately the component which comprises a transparent layer in the surface. In such use, the composition containing the components (a) and (d) constituting the surface layer is the first agent, and the composition containing the components (b) and (c) constituting the transparent layer is the second agent. After applying the first agent to the skin or the like, it is preferable to apply the second agent on the application surface. Even when the multi-agent is used, a coating film having a two-layer structure of an adhesion layer and a transparent layer shown in FIG. 2C can be obtained as in the case of using as one emulsified composition.
- Test Example 1-6 in which polyglyceryl-2 triisostearate, which is an oil component completely compatible with component (a), was blended as component (b), was uniform in composition and depended on the blending of water Although it was refreshing, the oil did not separate into two layers after application, and the surface layer of silicone oil was not formed.
- the composition was uniform as in Test Example 1-6, and freshness was also observed as a water-in-oil emulsion composition. Because there was no separated surface layer, the makeup was inferior.
- the (a) component is a polyhydric alcohol fatty acid ester and / or hydrocarbon
- the (b) component is a transparent non-volatile that separates when mixed with the (a) component at 25 ° C. It can be said that it is preferable to use silicone oil.
- the emulsified compositions of Test Examples 2-1 to 2-5 were prepared by changing the type of gelling agent used according to the formulation shown in Table 2 below, and the stability was evaluated from the appearance of each composition after storage. . Appearance photographs of the compositions of Test Examples 2-1 to 2-5 after 5 days storage at 50 ° C. are shown in FIGS. 3A to 3E, respectively.
- Components other than the components (b) and (d) were added to the component (a) and mixed under heating until uniform, and then mixed with the component (b) under heating. To the resulting mixture, the component (d) was gradually added under heating and stirring to obtain a water-in-oil emulsion composition (foundation).
- Example 2-1 Gelling agent not blended (ion exchange water)
- Test Example 2-2 (FIG. 3B): Dextrin palmitate Test
- Example 2-3 (FIG. 3C): (Behenic acid / eicosanedioic acid) Glyceryl Test
- Example 2-4 (FIG. 3D): Microcrystalline wax 7: Paraffin 93 or Microcrystalline wax (Permic 160, manufactured by Nikko Guatemala Corporation)
- Test Example 2-5 FIG. 3E: Zinc decyltrisiloxane carboxylate
- compositions of all the formulation examples maintained excellent stability (50 ° C., 1 W), showed a fresh feeling of use, a glossy finish, and excellent makeup.
- Emulsion pact (emulsification foundation)> (Production method) A mixture of (1) to (4) and (7) to (19) under heating was added to the mixture of (5) and (6) separately heated and mixed, and mixed under heating until uniform. Thereafter, the mixture (20) to (22) was gradually added to the mixture under heating and stirring to obtain an emulsion composition (emulsion foundation).
- Examples 13 to 16 Liquid Foundation> (Production method) A mixture of (1) to (4) and (7) to (18) under heating was added to the mixture of (5) and (6) separately heated and mixed, and mixed under heating until uniform. Thereafter, the liquid mixture of (19) to (24) was gradually added to the mixture under heating and stirring to obtain an emulsified composition (liquid foundation).
- Example 17 Liquid foundation> (Production method) A mixture of (1) and (4) to (9) under heating was added to the mixture of (2) and (3) separately heated and mixed, and mixed under heating until uniform. Thereafter, (10) was gradually added to the mixture under heating and stirring to obtain an emulsified composition (liquid foundation).
- Example 18 Eye shadow> (Production method) A mixture of (1) and (4) to (13) under heating was added to the mixture of (2) and (3) separately heated and mixed, and mixed under heating until uniform. Thereafter, (14) was gradually added to the mixture under heating and stirring to obtain an emulsified composition (eye shadow).
- Temporary hair dye> (Production method) A mixture of (1) and (4) to (8) under heating was added to the mixture of (2) and (3) separately heated and mixed, and mixed under heating until uniform. Thereafter, (9) was gradually added to the mixture under heating and stirring to obtain an emulsified composition (temporary hair dye).
- Example 20 mascara> (Production method) A mixture of (1) to (5) and (8) to (10) under heating was added to the mixture of (6) and (7) separately heated and mixed, and mixed under heating until uniform. Thereafter, the mixture of (11) to (15) was gradually added to the mixture under heating and stirring to obtain an emulsified composition (mascara).
- Example 21 Lipstick> (Production method) A mixture of (1) to (5), (8) to (10), (13) and (14) mixed under heating is added to the mixture of (6) and (7) separately heated and mixed, and heated. Until uniform. Thereafter, the mixture of (11) and (12) was gradually added to the mixture under heating and stirring to obtain an emulsified composition (lipstick).
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Abstract
Description
また、油中水型乳化組成物には、所望する効果に応じてエステル油、シリコーン油、炭化水素油等の様々な油剤が用いられるが、一般に、これらの油剤は各々性質が異なる。したがって、2種の異なる油剤を組み合わせて用い、それぞれの性質を併せもつ乳化組成物を得ようとしても、油剤同士の分離により組成物の安定性を維持させることは容易でなく、油中水型乳化組成物において併用可能な油剤の組み合わせは限られていた。
このような、水相、油相のそれぞれが関与する油中水型乳化組成物の安定性等における問題は、通常、相溶性の高い油剤同士を組み合わせるか、あるいは連続相である油相をゲル化し、組成物全体の流動性や分離を抑えること等によって解決されてきた。
本発明は、前記従来技術に鑑みなされたものであり、製剤として高い安定性を有し、みずみずしい感触、並びにツヤのある仕上がりをもたらし、且つ化粧もちに優れた油中水型乳化組成物を提供することを目的とする。
すなわち、本発明に係る乳化組成物は、
(a)多価アルコール脂肪酸エステル及び/又は炭化水素1~20質量%と、
(b)25℃で(a)成分と混合したときに分離する透明な不揮発性のシリコーン油3~20質量%と、
(c)デシルトリシロキサンカルボン酸亜鉛0.1~5質量%と、
(d)水と、
を含むことを特徴とする。
また、前記油中水型乳化組成物において、 (a)成分が、グリセリンの付加モル数が4~10であり、イソステアリン酸残基の数が1~4個であるトリイソステアリン酸ポリグリセリル、モノイソステアリン酸グリセリル、ペンタエリスリトール脂肪酸エステル、イソステアリルグリセリルエーテルから選択されることが好適である。
また、前記油中水型乳化組成物において、さらに、HLB値が7以下のシリコーン界面活性剤を含むことが好適である。
また、本発明に係る化粧方法は、
(I)多価アルコール脂肪酸エステル及び/又は炭化水素と、水とを含む第一剤を塗布する段階と、
(II)(I)段階後、その塗布面上に、25℃で(a)成分と混合したときに分離する透明な不揮発性のシリコーン油と、デシルトリシロキサンカルボン酸亜鉛と、を含む第二剤を塗布する段階と、
を含むことを特徴とする。
以下、各成分について詳細に説明する。
(a)成分は、多価アルコール脂肪酸エステル及び/又は炭化水素であって、且つ、常温(25℃)で(b)成分と混合したときに、溶解せずに分離する油分である。本発明において(a)成分は、塗布時に色材等を抱え込んで密着油分となり、染み出し油分である(b)成分と速やかに分離する。したがって、(a)成分は、(b)成分よりも色材等の分散性に優れ、皮膚との親和性が高く、皮膚に密着しやすいものが好ましい。
かかるイソステアリン酸ポリグリセリルは、例えば、特許第3487881号や特開2006-111539号公報(水酸基が1200以下であり、全ての水酸基のうち1級水酸基が50%以上であるポリグリセリンと脂肪酸とがエステル化されたポリグリセリン脂肪酸エステル)に記載の方法によって製造することができる。
これらの市販品としては、例えば、「サラコスP-B822」(日清オイリオグループ株式会社製)、「コスモール168M」(日清オイリオグループ株式会社製)が挙げられ、これらを好適に使用することができる。
(b)成分は、常温(25℃)で(a)成分と混合したときに、溶解せずに分離する透明な、25℃において不揮発性のシリコーン油であり、本発明の乳化組成物を皮膚等に塗布した後、(a)成分と分離して表層を形成し、特に化粧もちを向上させる成分である。本発明において、前記(b)成分は、B型粘度計による25℃における粘度が500mPa・s以下で液状を呈するものが好ましい。
(測定条件)
(a)と(b)を、(a):(b)=1:1(質量比)で用いて、90℃に加温し、撹拌混合し、次いで静置し、混合物が25℃になった場合に、境界が均一に2相に分離しているものを「分離する」とし、半透明な状態または、境界がなく透明な相溶した状態を「分離せず」とした。なお、(b)成分として二種以上のシリコーン油を用いる場合、分離の有無は、それらの配合割合により異なる。このため、分離の有無は、(b)成分の配合割合に応じて確認する必要がある。
これらのシリコーン油は、本発明の油中水型乳化組成物の使用形態に応じて1種又は2種以上を組み合わせて用いることができ、例えば、本発明をファンデーション等に用いる場合はジメチルポリシロキサン、口紅等に用いる場合はジフェニルジメチコンやトリメチルペンタフェニルトリシロキサンを用いることが好ましい。
(c)成分は、カルボキシ変性シリコーンの金属塩(金属石鹸)であるデシルトリシロキサンカルボン酸亜鉛である。
本発明に用いられるデシルトリシロキサンカルボン酸亜鉛の入手方法は特に限定されないが、その合成方法としては、例えば、
(A)下記一般式(I)で表わされる化合物を含む組成物と、
(B)亜鉛イオン(Zn2+)を含む水溶液と、
(C)水酸化物イオンを含む水溶液と、
を混合することが挙げられる。
上記(A)成分は、公知の合成方法、例えば、1,1,1,3,5,5,5-ヘプタメチルトリシロキサンと、ビニル末端を有するカルボン酸トリメチルシリル誘導体とを、白金系触媒の存在下に付加反応させ、保護基であるトリメチルシリル基1モルあたり、少なくとも1モル以上の一価アルコール、水又はこれらの混合物を加えて加熱することにより、加アルコール分解により脱保護させる工程により得られ、また、市販品を用いてもよい。
(B)成分としては、例えば、塩化亜鉛、硫酸亜鉛、硝酸亜鉛、リン酸亜鉛、水酸化亜鉛等の水溶液が挙げられ、(C)成分としては、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、水酸化マグネシウム、水酸化バリウム、水酸化亜鉛、水酸化アルミニウム、水酸化鉄、水酸化銅等の水溶液が挙げられる。
上記(A)成分を(B)成分(水溶液)に加えると、活性部である特定官能基部分が陰イオンの性質をもち、これが(B)成分より電離した多価金属陽イオンと反応して金属石鹸を形成する。この金属石鹸を(C)成分と中和させることにより、デシルトリシロキサンカルボン酸亜鉛が生成される。
<合成例1>
撹拌機、温度計、冷却管を備えたフラスコに、1%水酸化ナトリウム(NaOH)水溶液1400gを調製し、70℃に加温した。下記合成方法により得た化合物α145.5gを70℃で添加後、該温度を維持しながらさらに1時間撹拌した。その後、25%硫酸亜鉛七水和物(ZnSO4・7H2O)水溶液231.6gを70℃で添加し、さらに1時間撹拌して亜鉛石鹸を析出させた。そこへ5%水酸化ナトリウム水溶液を65.1g添加し、70℃で1時間撹拌して中性であること(中和反応が完了したこと)を確認した後、冷却して水を除去した。得られた生成物を過剰量のイオン交換水中に加熱溶解し、水を分離する操作を5回行い、水酸化亜鉛及び副生する塩(Na2SO4)を洗浄した。
その後、生成物を減圧下、105℃において乾燥し、透明から白色の固体状の物質を得た。分析の結果、前記物質は、化合物A由来部分を「RSi-C10H20-COO-」と略記した場合、平均組成式として「RSi-C10H20-COO-(Zn2+)5/8(OH-)1/4」と表わされる複合塩組成物を含有していた。
なお、中和反応式は次のとおり。
8RSi-C10H20-COONa+5ZnSO4+2NaOH→3Zn(O-C(=O)-C10H20-RSi)2+2(RSi-C10H20-(C=O)-O-Zn-OH)+5Na2SO4
撹拌機、還流冷却機、滴下ロート及び温度計を備えたフラスコに1,1,1,3,5,5,5-ヘプタメチルトリシロキサン100g、白金-1,3-ジビニル-1,1,3,3-テトラメチルジシロキサン錯体のトルエン溶液0.02gを加え、70~100℃の範囲を保つように、ウンデシレン酸トリメチルシリル105g滴下した。滴下終了後、2時間、100℃で熟成した後、ガスクロマトグラフィーを用いて反応の完了を確認した。低沸点分を減圧下、留去した。その後、メタノール、水を加え、還流下5時間熟成し、脱保護を行った。その後再び低沸点分を減圧下除去し、化合物αを得た。分析の結果、化合物αは、下記構造式で表わされるものであることが確認された。
(d)成分である水は、油中水型組成物の内水相を構成する成分であり、水相に配合可能な水性成分を含み得る。水の配合量は本発明の効果を損なわない範囲であれば特に制限されないが、みずみずしさにより優れたゲル状(クリーム状)の組成物とする場合、内水相比として組成物に対し40質量%以上とすることが好ましく、より好ましくは40~90質量%、特に好ましくは45~90質量%である。前記配合量は、水及び任意の水性成分からなる内水相全体の配合量に相当する。
このようなシリコーン界面活性剤としては、例えば、PEG-3ジメチコン、PEG-9メチルエーテルジメチコン、PEG-10ジメチコン、PEG-9ポリジメチルシロキシエチルジメチコン、ラウリルPEG-9ポリジメチルシロキシエチルジメチコン、PEG/PPG-20/22ブチルエーテルジメチコン、ポリグリセリル-3ジシロキサンジメチコン、ポリグリセリル-3ポリジメチルシロキシエチルジメチコン、ラウリルポリグリセリル-3ポリジメチルシロキシエチルジメチコン等が挙げられる。本発明において、好ましくはPEG-10ジメチコン、ラウリルPEG-9ポリジメチルシロキシエチルジメチコン、より好ましくはPEG-10ジメチコンである。
前記乳化剤の配合量は特に限定されないが、一般に、0.05~1.0質量%程度の使用が好ましい。
加えて、本発明の乳化物は、上記油分による効果とともに、(d)成分である水の配合により、塗布の際にみずみずしい使用感触が得られるものであるが、油分たる(a)及び(b)成分と、(d)成分とを単に乳化させただけでは、水の高い流動性が、二種の油分の安定分散を妨げ、組成物中でこれらを分離させてしまうことになる。
そこで、本発明者らは、上記二種の油分と、水とが、それぞれ組成物中に安定して均一分散された状態を保つため、(c)成分であるデシルトリシロキサンカルボンサン亜鉛を用いることとしたのである。
前記系において、(c)成分に取り込まれた乳化粒子((d)成分と、(d)成分及び(a)成分のラメラ)は、連続相中に密に充填されており、物理的にほとんど動くことがないため、分離や合一が生じ難い。したがって、本発明の乳化組成物は、見かけ上、流動しないゲルの性状をもった安定な均一一層系の様相を呈する。
図2(A)は、本発明の乳化組成物を皮膚10に載せたときの状態であり、塗布前の組成物そのものを示す。図1(A)の時点において、(a)~(d)成分は、図1(A)のような均一層11を構成している。
(b)成分を主とする透明層15は、油剤としてのツヤのある仕上がりをもたらすとともに、(c)成分に固定化されることにより表面皮膜として化粧もちの向上に寄与する。
(a)成分もまた、油剤としてツヤ等の効果を発揮するが、加えて、該成分は色材を抱え込む性質があるため、前記色材は、前記透明層15により覆われた密着層14に留まることとなる。したがって、本発明の組成物に色材を配合すると、塗布面に触れても色移りが生じ難いものとなる。
さらに、表面の透明層15が光の拡散を促進するため、ファンデーション等への使用においては、塗布面に素肌のような透明感を付与することもできる。
なお、(a)及び(b)成分の組み合わせによっては、皮膚への塗布後に図2(C)のように完全に二層に分離せず、図2(B)に示すように、(a)成分の皮膜上に(b)及び(c)成分の皮膜が部分的に形成されることがある。このような場合も、上記した二層構造による効果は十分に得られる。
なかでも、外皮に塗布して使用する化粧料への応用が好ましく、例えば、美白用美容液、乳液、クリーム、パック、ファンデーション、化粧下地、口紅、リップグロス、アイシャドウ、アイライナー、マスカラ、染毛料、ヘアトリートメント、ヘアフォーム、ヘアパック等としての使用が挙げられ、特にファンデーションとしての使用が好ましい。
実施例の説明に先立ち、各試験で用いた組成物の評価方法について説明する。
<組成物の安定性>
50℃に設定した恒温槽内に1週間静置保存した後の各組成物の状態を、下記評価基準により評価した。
(評価基準)
○:成分の分離は認められず、均一一層の状態が維持された。
○△:成分の分離はほとんど認められず、均一一層の状態がほぼ維持された。
△:若干の成分の分離が認められた。
×:著しい成分の分離が認められた。
10名の専門パネルによる実使用試験を行った。各組成物は、みずみずしい使用感触について下記スコアに基づき採点され、算出したスコア平均値を評価値として下記評価基準により評価した。
(スコア)
5点:非常に優れている
4点:優れている
3点:普通
2点:劣る
1点:非常に劣る
(評価基準)
○:評価値(平均値)4.0点以上5.0点以下
△:評価値(平均値)2.5点以上4.0点未満
×:評価値(平均値)1.0点以上2.5点未満
10名の専門パネルによる実使用試験を行った。各組成物は、ツヤのある仕上がりについて下記スコアに基づき採点され、算出したスコア平均値を評価値として下記評価基準により評価した。
(スコア)
5点:非常に優れている
4点:優れている
3点:普通
2点:劣る
1点:非常に劣る
(評価基準)
○:評価値(平均値)4.0点以上5.0点以下
△:評価値(平均値)2.5点以上4.0点未満
×:評価値(平均値)1.0点以上2.5点未満
10名の専門パネルによる実使用試験を行った。各組成物は、化粧もちのよさについて下記スコアに基づき採点され、算出したスコア平均値を評価値として下記評価基準により評価した。
(スコア)
5点:非常に優れている
4点:優れている
3点:普通
2点:劣る
1点:非常に劣る
(評価基準)
○:評価値(平均値)4.0点以上5.0点以下
△:評価値(平均値)2.5点以上4.0点未満
×:評価値(平均値)1.0点以上2.5点未満
*2:コスモール168M(日清オイリオグループ株式会社製)
*3:KF-96A-6cs(信越化学工業株式会社製)
*4:コスモール43V(日清オイリオグループ株式会社製)
*5:KF-6038(信越化学工業社製)
(製造方法)
(b)及び(d)成分以外を(a)成分に加え、加熱下で均一になるまで混合したものを、加熱下で(b)成分と混合した。得られた混合物に、加熱撹拌下で徐々に(d)成分を加え、油中水型乳化組成物(ファンデーション)を得た。
一方、(b)成分として、(a)成分と完全に相溶する油分であるトリイソステアリン酸ポリグリセリル-2を配合した試験例1-6は、組成物としては均一なものとなり、水の配合によるみずみずしさも備えていたが、塗布後に油分が二層分離せず、シリコーン油による表層が形成されないため、化粧もちに劣っていた。
また、(b)成分を配合しなかった試験例1-7においても、試験例1-6と同様、組成物としては均一であり、油中水型乳化組成物としてのみずみずしさも認められたものの、分離した表層が存在しないため、化粧もちに劣っていた。
以上のことから、本発明においては、(a)成分として多価アルコール脂肪酸エステル及び/又は炭化水素、(b)成分として25℃で(a)成分と混合したときに分離する透明な不揮発性のシリコーン油を用いることが好適であるといえる。
(b)及び(d)成分以外を(a)成分に加え、加熱下で均一になるまで混合したものを、加熱下で(b)成分と混合した。得られた混合物に、加熱撹拌下で徐々に(d)成分を加え、油中水型乳化組成物(ファンデーション)を得た。
試験例2-1(図3A):ゲル化剤未配合(イオン交換水)
試験例2-2(図3B):パルミチン酸デキストリン
試験例2-3(図3C):(ベヘン酸/エイコサン二酸)グリセリル
試験例2-4(図3D):マイクロクリスタリンワックス7:パラフィン93またはマイクロクリスタリンワックス(パーミック160、日興リカ株式会社製)
試験例2-5(図3E):デシルトリシロキサンカルボン酸亜鉛
したがって、本発明に係る油中水型乳化組成物においては、互いに分離する油分が均一に分散された安定な状態を維持するため、デシルトリシロキサンカルボン酸亜鉛を配合することが好ましい。
*6:KF-6017(信越化学工業社製)
(製造方法)
(3)及び(5)以外を(1)及び(2)に加え、加熱下で均一になるまで混合したものを、加熱下で(3)と混合した。得られた混合物に、加熱撹拌下で徐々に(5)を加え、油中水型乳化組成物(ファンデーション)を得た。
(製造方法)
(1)~(4)、(7)~(19)を加熱下で混合したものを、別途加熱混合した(5)及び(6)の混合物に加え、加熱下で均一になるまで混合した。その後、前記混合物へ(20)~(22)の混合液を加熱撹拌下にて徐添し、乳化組成物(乳化ファンデーション)を得た。
(製造方法)
(1)~(4)、(7)~(18)を加熱下で混合したものを、別途加熱混合した(5)及び(6)の混合物に加え、加熱下で均一になるまで混合した。その後、前記混合物へ(19)~(24)の混合液を加熱撹拌下にて徐添し、乳化組成物(リキッドファンデーション)を得た。
(製造方法)
(1)、(4)~(9)を加熱下で混合したものを、別途加熱混合した(2)及び(3)の混合物に加え、加熱下で均一になるまで混合した。その後、前記混合物へ(10)を加熱撹拌下にて徐添し、乳化組成物(リキッドファンデーション)を得た。
(製造方法)
(1)、(4)~(13)を加熱下で混合したものを、別途加熱混合した(2)及び(3)の混合物に加え、加熱下で均一になるまで混合した。その後、前記混合物へ(14)を加熱撹拌下にて徐添し、乳化組成物(アイシャドウ)を得た。
(製造方法)
(1)、(4)~(8)を加熱下で混合したものを、別途加熱混合した(2)及び(3)の混合物に加え、加熱下で均一になるまで混合した。その後、前記混合物へ(9)を加熱撹拌下にて徐添し、乳化組成物(一時染毛料)を得た。
(製造方法)
(1)~(5)、(8)~(10)を加熱下で混合したものを、別途加熱混合した(6)及び(7)の混合物に加え、加熱下で均一になるまで混合した。その後、前記混合物へ(11)~(15)の混合液を加熱撹拌下にて徐添し、乳化組成物(マスカラ)を得た。
2 (d)成分
3 (b)成分
4 (a)成分及び(d)成分のラメラ
10 皮膚
11 均一層
12 (a)成分
13 (b)成分
14 密着層
15 透明層
Claims (5)
- (a)多価アルコール脂肪酸エステル及び/又は炭化水素1~20質量%と、
(b)25℃で(a)成分と混合したときに分離する透明な不揮発性のシリコーン油3~20質量%と、
(c)デシルトリシロキサンカルボン酸亜鉛0.1~5質量%と、
(d)水と、
を含むことを特徴とする油中水型乳化組成物。 - (a)成分が、グリセリンの付加モル数が4~10であり、イソステアリン酸残基の数が1~4個であるトリイソステアリン酸ポリグリセリル、モノイソステアリン酸グリセリル、ペンタエリスリトール脂肪酸エステル、イソステアリルグリセリルエーテルから選択されることを特徴とする請求項1に記載の油中水型乳化組成物。
- さらに、HLB値が7以下のシリコーン界面活性剤を含むことを特徴とする請求項1に記載の油中水型乳化組成物。
- 請求項1~3のいずれかに記載の油中水型乳化組成物を含むことを特徴とする化粧料。
- (I)多価アルコール脂肪酸エステル及び/又は炭化水素と、水とを含む第一剤を塗布する段階と、
(II)(I)段階後、その塗布面上に、25℃で(a)成分と混合したときに分離する透明な不揮発性のシリコーン油と、デシルトリシロキサンカルボン酸亜鉛と、を含む第二剤を塗布する段階と、
を含むことを特徴とする化粧方法。
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WO2018003440A1 (ja) * | 2016-06-29 | 2018-01-04 | 株式会社 資生堂 | 水中油型乳化唇用化粧料 |
JP2019131541A (ja) * | 2018-01-31 | 2019-08-08 | 株式会社コーセー | 油中水型乳化組成物 |
JP2020186217A (ja) * | 2019-05-17 | 2020-11-19 | 花王株式会社 | 油中水型乳化化粧料 |
JP2021098028A (ja) * | 2016-03-31 | 2021-07-01 | ロレアル | 皮膜形成剤および不揮発性油を含むエマルジョンを包装および塗布するための器具ならびに組成物 |
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WO2022135682A1 (en) * | 2020-12-21 | 2022-06-30 | Lvmh Recherche | Water-in-oil cosmetic composition |
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- 2013-10-28 ES ES13850887.4T patent/ES2616041T3/es active Active
- 2013-10-28 CN CN201380056913.9A patent/CN104853732B/zh active Active
- 2013-10-28 BR BR112015008777A patent/BR112015008777A2/pt not_active Application Discontinuation
- 2013-10-28 EP EP13850887.4A patent/EP2915523B1/en active Active
- 2013-10-28 WO PCT/JP2013/079138 patent/WO2014069403A1/ja active Application Filing
- 2013-10-28 KR KR1020157007006A patent/KR102110629B1/ko active IP Right Grant
- 2013-10-28 RU RU2015111143A patent/RU2649120C2/ru not_active IP Right Cessation
- 2013-10-30 TW TW102139272A patent/TWI646976B/zh not_active IP Right Cessation
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JP2021098028A (ja) * | 2016-03-31 | 2021-07-01 | ロレアル | 皮膜形成剤および不揮発性油を含むエマルジョンを包装および塗布するための器具ならびに組成物 |
WO2018003440A1 (ja) * | 2016-06-29 | 2018-01-04 | 株式会社 資生堂 | 水中油型乳化唇用化粧料 |
US10624823B2 (en) | 2016-06-29 | 2020-04-21 | Shiseido Company, Ltd. | Oil-in-water type emulsion cosmetic for lips |
JP2019131541A (ja) * | 2018-01-31 | 2019-08-08 | 株式会社コーセー | 油中水型乳化組成物 |
JP7309373B2 (ja) | 2018-01-31 | 2023-07-18 | 株式会社コーセー | 油中水型乳化組成物 |
JP2020186217A (ja) * | 2019-05-17 | 2020-11-19 | 花王株式会社 | 油中水型乳化化粧料 |
JP7373916B2 (ja) | 2019-05-17 | 2023-11-06 | 花王株式会社 | 油中水型乳化化粧料 |
Also Published As
Publication number | Publication date |
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IN2015DN03828A (ja) | 2015-10-02 |
US20150290114A1 (en) | 2015-10-15 |
TW201427701A (zh) | 2014-07-16 |
BR112015008777A2 (pt) | 2017-07-04 |
JP5852262B2 (ja) | 2016-02-03 |
CN104853732B (zh) | 2017-09-22 |
RU2015111143A (ru) | 2016-12-20 |
KR102110629B1 (ko) | 2020-05-13 |
ES2616041T3 (es) | 2017-06-09 |
EP2915523A1 (en) | 2015-09-09 |
TWI646976B (zh) | 2019-01-11 |
CN104853732A (zh) | 2015-08-19 |
JPWO2014069403A1 (ja) | 2016-09-08 |
EP2915523A4 (en) | 2016-04-27 |
RU2649120C2 (ru) | 2018-03-29 |
US9572763B2 (en) | 2017-02-21 |
HK1209354A1 (en) | 2016-04-01 |
EP2915523B1 (en) | 2017-01-11 |
KR20150076149A (ko) | 2015-07-06 |
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