WO2020067358A1 - Procédé de réduction des rides de la peau - Google Patents

Procédé de réduction des rides de la peau Download PDF

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Publication number
WO2020067358A1
WO2020067358A1 PCT/JP2019/038001 JP2019038001W WO2020067358A1 WO 2020067358 A1 WO2020067358 A1 WO 2020067358A1 JP 2019038001 W JP2019038001 W JP 2019038001W WO 2020067358 A1 WO2020067358 A1 WO 2020067358A1
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polymer
solution
length
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PCT/JP2019/038001
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将行 飯田
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花王株式会社
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Priority to JP2020549395A priority Critical patent/JP7366044B2/ja
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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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

Definitions

  • the present invention relates to a method for improving skin wrinkles.
  • Aging increases wrinkles on human skin. This is part of the skin aging phenomenon and depends on several factors, including changes in skin tissue and the effects of exposure to ultraviolet light. Techniques for making skin wrinkles less prominent have been proposed, but the cosmetic surgery method required shape control by invading the skin. Skin care products that improve skin wrinkles non-invasively are also known, but the effect of improvement is extremely low, and women with wrinkle problems have not been satisfied. Therefore, a method that can control the shape of the skin non-invasively and effectively improve wrinkles is desired.
  • Patent Literature 1 relates to a cosmetic for makeup which is excellent in applicability and uniformity of a decorative film, in which a predetermined fructooligosaccharide fatty acid ester, a volatile hydrocarbon, and an oil-soluble film-forming resin are blended.
  • Patent Literature 2 relates to a cosmetic containing a film-forming polymer in which a predetermined functional group is introduced into a skeleton of a polycycloolefin polymer, and having a good makeup feel and feel.
  • the present invention relates to the following [1] to [3].
  • [1] A method for improving skin wrinkles by applying a composition containing a polymer having a silicone structure to the skin, wherein the polymer has a deformation ratio of 0.3 to 1 measured by the following method (1).
  • a method wherein the minimum diameter of a cylindrical mandrel in which cracks do not occur in the polymer film is 2 mm or more and 25 mm or less in a bending resistance test by a cylindrical mandrel method performed by the following method (2).
  • Method (1) A 10% by mass solution of the polymer in hexamethyldisiloxane is prepared.
  • a solution of 0.005 g of the solution was applied to one side of a polyethylene sheet having a width of 20 mm x a length of 100 mm x a thickness of 0.03 mm in a range of 20 mm in width x 50 mm in length from one end of the short side in the length direction. Dry for 10 minutes in a thermostat set at °C.
  • the length of the polyethylene sheet in the portion to which the solution was applied is L1
  • the length of the polyethylene sheet in the portion deformed by shrinkage after drying is L2
  • the value of L2 / L1 is the deformation ratio.
  • the solution is applied to a polyethylene terephthalate film having a width of 50 mm, a length of 100 mm and a thickness of 0.1 mm using a 200 ⁇ m applicator, and dried in a thermostat set at 40 ° C. for 120 minutes to prepare a test piece.
  • a bending resistance test was performed in accordance with the cylindrical mandrel method specified in JIS K5600-5-1: 1999, and the minimum diameter of the cylindrical mandrel where cracks did not occur in the polymer film on the test piece. Ask for.
  • a method for improving skin wrinkles comprising: a step of applying a composition containing a polymer having a silicone structure to the periphery of wrinkles on the skin; and a step of drying the composition to shrink the polymer.
  • the polymer has a deformation ratio of not less than 0.3 and not more than 1 measured by the above method (1), and has undergone a bending resistance test by a cylindrical mandrel method performed by the above method (2).
  • the method wherein the minimum diameter of the cylindrical mandrel that does not cause cracks in the film is 2 mm or more and 25 mm or less.
  • a method wherein the minimum diameter of a cylindrical mandrel in which cracks do not occur in the polymer film is 2 mm or more and 25 mm or less in a bending resistance test by a cylindrical mandrel method performed by the method (2).
  • the present invention relates to a method of applying a composition containing a polymer having a silicone structure to a wrinkle periphery of skin, wherein the polymer has a deformation ratio of 0.3 or more and 1 or less measured by the following method (1). And in a bending resistance test by a cylindrical mandrel method performed by the following method (2), wherein the minimum diameter of the cylindrical mandrel in which cracks do not occur in the polymer film is 2 mm or more and 25 mm or less.
  • the present invention also provides a method for improving skin wrinkles, comprising the steps of: applying a composition containing a polymer having a silicone structure to the periphery of wrinkles on the skin; and then drying the composition to shrink the polymer.
  • the polymer has a deformation ratio of 0.3 or more and 1 or less as measured by the following method (1), and is subjected to a bending resistance test by a cylindrical mandrel method performed by the following method (2).
  • the present invention relates to a method in which the minimum diameter of a cylindrical mandrel that does not cause cracks in a polymer film is 2 mm or more and 25 mm or less.
  • these methods are also appropriately referred to as “improvement methods of the present invention”.
  • Method (1) A 10% by mass solution of the polymer in hexamethyldisiloxane is prepared.
  • a solution of 0.005 g of the solution was applied to one side of a polyethylene sheet having a width of 20 mm x a length of 100 mm x a thickness of 0.03 mm in a range of 20 mm in width x 50 mm in length from one end of the short side in the length direction. Dry for 10 minutes in a thermostat set at °C.
  • the length of the polyethylene sheet in the portion to which the solution was applied is L1
  • the length of the polyethylene sheet in the portion deformed by shrinkage after drying is L2
  • the value of L2 / L1 is the deformation ratio.
  • the solution is applied to a polyethylene terephthalate film having a width of 50 mm, a length of 100 mm and a thickness of 0.1 mm using a 200 ⁇ m applicator, and dried in a thermostat set at 40 ° C. for 120 minutes to prepare a test piece.
  • a bending resistance test was performed in accordance with the cylindrical mandrel method specified in JIS K5600-5-1: 1999, and the minimum diameter of the cylindrical mandrel where cracks did not occur in the polymer film on the test piece. Ask for.
  • the present invention is a method for applying a composition containing a polymer having a silicone structure to a wrinkle peripheral portion of the skin, wherein the polymer has a deformation ratio of 0.3 or more as measured by the method (1).
  • the present invention relates to a method in which the minimum diameter of a cylindrical mandrel that does not cause cracks in the polymer film is 2 mm or more and 25 mm or less in a bending resistance test by a cylindrical mandrel method performed by the method (2).
  • the method is appropriately referred to as “application method of the present invention”.
  • skin wrinkles means irregularities and streaks appearing on the skin surface. Skin wrinkles tend to appear around the mouth, around the eyes, forehead, neck, etc. Small streaks are small wrinkles, large streaks are large wrinkles, and large wrinkles are caused by flow of pores on the law lines, cheeks and the like.
  • the improvement method of the present invention has an effect of making any wrinkles inconspicuous, and is particularly preferable in that even large wrinkles such as the legal lines can be improved non-invasively.
  • the present inventor has applied a composition containing a polymer having a silicone structure and having a predetermined deformation ratio and bending resistance (hereinafter, also simply referred to as a “polymer”) to the skin, whereby the skin is non-invasively applied. It has been found that the shape can be controlled and wrinkles on the skin can be made less noticeable.
  • the "method of improving skin wrinkles” refers to, as described later, pulling and stretching the skin around the wrinkles by the contraction action of the polymer contained in the composition, and controlling the shape of the skin in a non-invasive manner. Is the way.
  • the polymer having a silicone structure used in the present invention has a deformation ratio of 0.3 or more and 1 or less measured by the following method (1), and has a bending resistance by a cylindrical mandrel method performed by the following method (2). In the test, the minimum diameter of the cylindrical mandrel that does not crack in the polymer film is 2 mm or more and 25 mm or less.
  • Method (1) A 10% by mass solution of the polymer in hexamethyldisiloxane is prepared.
  • a solution of 0.005 g of the solution was applied to one side of a polyethylene sheet having a width of 20 mm x a length of 100 mm x a thickness of 0.03 mm in a range of 20 mm in width x 50 mm in length from one end of the short side in the length direction. Dry for 10 minutes in a thermostat set at °C.
  • the length of the polyethylene sheet in the portion to which the solution was applied is L1
  • the length of the polyethylene sheet in the portion deformed by shrinkage after drying is L2
  • the value of L2 / L1 is the deformation ratio.
  • the solution is applied to a polyethylene terephthalate film having a width of 50 mm, a length of 100 mm and a thickness of 0.1 mm using a 200 ⁇ m applicator, and dried in a thermostat set at 40 ° C. for 120 minutes to prepare a test piece.
  • a bending resistance test was performed in accordance with the cylindrical mandrel method specified in JIS K5600-5-1: 1999, and the minimum diameter of the cylindrical mandrel where cracks did not occur in the polymer film on the test piece. Ask for.
  • the improvement method of the present invention preferably includes a step of applying the composition to a wrinkle periphery of skin, and a step of drying the composition to shrink the polymer.
  • FIG. 1 (b) is a schematic view of a polyethylene sheet in which a part thereof is deformed (curled) by polymer shrinkage after drying the polyethylene sheet 1 coated with the solution.
  • the length of the polyethylene sheet in the portion where the solution was applied was L1 (50 mm)
  • the length of the polyethylene sheet in the portion deformed by shrinkage after drying was L2
  • L2 / L1 is calculated, and this value is used as the deformation ratio.
  • L2 is the average of the values measured on the two long sides of the polyethylene sheet 1. The larger the value of L2 / L1, the larger the amount of shrinkage of the polymer due to drying. The upper limit of L2 / L1 is 1.
  • the deformation ratio L2 / L1 evaluated by the method (1) is 0.3 or more, preferably 0.5 or more, more preferably 0.6 or more, It is still more preferably 0.7 or more, still more preferably 0.8 or more, still more preferably 0.85 or more, even more preferably 0.9 or more, and still more preferably 0.95 or more. is there.
  • the deformation ratio can be specifically evaluated by the method described in Examples.
  • the polymer used in the present invention is excellent in bending resistance.
  • the minimum diameter of the cylindrical mandrel that does not cause cracks in the polymer film is 2 mm or more. It is 25 mm or less. This makes it difficult for the film containing the polymer to crack, and for the film to contract easily while following the skin shape.
  • the smaller the minimum diameter of the cylindrical mandrel the better the bending resistance. From the viewpoint of obtaining sufficient adhesion between the film and the skin surface when the film containing the polymer shrinks, the minimum diameter is 25 mm or less, preferably 20 mm or less, more preferably 12 mm or less, and still more preferably 8 mm or less.
  • the minimum diameter of the cylindrical mandrel where cracks do not occur is preferably 2 mm or more, and more preferably 3 mm or more, from the viewpoint of imparting sufficient strength and shape control effect to extend the wrinkles of the skin and make it inconspicuous. is there.
  • the specific range of the minimum diameter of the cylindrical mandrel is preferably 2 to 25 mm, more preferably 2 to 20 mm, still more preferably 2 to 12 mm, still more preferably 2 to 8 mm, and still more preferably 3 to 6 mm. More preferably, it is 3 to 5 mm.
  • the bending resistance can be evaluated using a type 1 bending test apparatus defined in JIS K5600-5-1: 1999, specifically by the method described in Examples.
  • the ratio of the deformation ratio of the polymer having a silicone structure used in the present invention to the minimum diameter (mm) of the mandrel determined by the method (2) [(deformation ratio) / (mandrel ratio)] Minimum diameter)] is preferably 0.01 or more, more preferably 0.02 or more, further preferably 0.10 or more, and still more preferably 0.15 or more, from the viewpoint of the effect of improving skin wrinkles. It is preferably 0.5 or less, more preferably 0.4 or less, from the viewpoint of imparting sufficient strength and shape control effect to lengthen wrinkles and make them less noticeable.
  • the specific range of the ratio is preferably 0.01 to 0.5, more preferably 0.02 to 0.5, further preferably 0.10 to 0.5, and still more preferably 0.15 to 0.5. 5, more preferably 0.15 to 0.4.
  • the “silicone structure” refers to a structure represented by the following general formula (I).
  • R 1 is each independently a hydrocarbon group having 1 to 12 carbon atoms, and p is an integer of 1 or more.
  • R 1 is preferably An alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms or a phenyl group, and still more preferably an alkyl group having 1 to 3 carbon atoms. And still more preferably a methyl group.
  • the polymer only needs to have a silicone structure, and may be a polymer having only a silicone structure. However, from the viewpoint of a polymer having the above-described predetermined characteristics, it is preferable that the polymer has a silicone structure in part.
  • the silicone structure may be present in any of the main chain and the side chain in the polymer, and is present in the side chain in view of the polymer having the predetermined characteristics. Is preferred.
  • the bonding form is not particularly limited.
  • the silicone structure may be present at the terminal of the polymer main chain, or the silicone structure may be present in the polymer main chain in a block form. Alternatively, it may be a random-bonded copolymer.
  • a polymer graft-modified with a compound having a silicone structure can also be used.
  • the polymer used in the present invention is preferably a silicone-modified polymer, and specific examples thereof include a silicone-modified polymer containing a norbornane structure such as a silicone-modified polynorbornene; a silicone-modified pullulan; a trialkylsiloxysilicic acid, a fluorine-modified alkylsiloxysilicic acid, Silicate compounds having a silicone structure such as phenyl-modified alkylsiloxysilicic acid; silicone dendrimers;
  • the norbornane structure means a structure represented by the following formula.
  • the norbornane structure-containing silicone-modified polymer may be any silicone-modified polymer having a structure represented by the formula at an arbitrary site in the polymer.
  • Examples of the silicone-modified polymer containing a norbornane structure include a polymer having a repeating unit represented by the following general formula (1) or (2).
  • R 2 is each independently an alkyl group having 1 to 12 carbon atoms
  • X is a group represented by the following formula (i).
  • a is an integer of 1 or more and 3 or less
  • b is an integer of 0 or more and 2 or less.
  • R 1 is the same as described above
  • c is an integer of 1 or more and 5 or less.
  • R 1 , R 2 and b are the same as described above, and d is an integer of 2 or more and 5 or less.
  • R 2 is independently an alkyl group having 1 to 12 carbon atoms, and from the viewpoint of skin wrinkle improvement effect and versatility, a methyl group, an ethyl group, an n-propyl group. , A butyl group or a pentyl group is preferred, and a methyl group is more preferred.
  • X is a group represented by the formula (i), and in the formula (i), R 1 is each independently a hydrocarbon group having 1 to 12 carbon atoms. From the viewpoint of skin wrinkle improvement effect and versatility, R 1 is preferably an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, and more preferably 1 to 12 carbon atoms.
  • b is an integer of 0 or more and 2 or less, preferably 0 or 1 or a combination thereof from the same viewpoint, and 0 is more preferable.
  • R 1 , R 2 and b are the same as described above.
  • R 1 and R 2 are methyl groups and d is 2 or 3, from the same viewpoint. That is, the cyclic silicone structure in the general formula (2) is preferably a structure represented by the following formula (4) or (5).
  • the proportion of the repeating unit represented by the general formula (1) or (2) in the silicone-modified polymer containing a norbornane structure is preferably a proportion of the total number of repeating units in the polymer. It is at least 10%, more preferably at least 30%, further preferably at least 50%.
  • the upper limit is 100%, preferably 95% or less, more preferably 90% or less, and further preferably 70% or less.
  • the specific range of the number of repeating units represented by the general formula (1) or (2) in the silicone-modified polymer having a norbornane structure is preferably 10 to 100% of the total number of repeating units in the polymer. It is preferably from 10 to 95%, more preferably from 30 to 90%, even more preferably from 50 to 70%.
  • the norbornane-structure-containing silicone-modified polymer may have a repeating unit represented by the following general formula (3) in addition to the repeating unit represented by the general formula (1) or (2).
  • R 3 to R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group and a halogenated carbon atom having 1 to 10 carbon atoms.
  • Two groups selected from R 3 to R 6 may combine with each other to form an alicyclic structure, an aromatic ring structure, a carbimide group or an acid anhydride group. b is the same as described above.
  • the proportion of the repeating unit represented by the general formula (3) in the norbornane structure-containing silicone-modified polymer is preferably 90% or less of the total number of repeating units in the polymer from the viewpoint of the effect of improving skin wrinkles. It is more preferably at most 70%, further preferably at most 50%.
  • the proportion thereof is preferably 5% or more, more preferably 10% or more, and still more preferably 30% of the total number of repeating units in the polymer. That is all.
  • the specific range of the number of repeating units represented by the general formula (3) in the silicone-modified polymer having a norbornane structure is preferably from 5 to 90%, more preferably from 10 to 90% of the total number of repeating units in the polymer. 70%, more preferably 30 to 50%.
  • the proportion of the repeating units represented by the above general formulas (1) to (3) in the silicone-modified polymer having a norbornane structure can be determined by 1 H-NMR measurement.
  • silicone-modified polymer containing a norbornane structure silicone-modified polynorbornene is preferable, and silicone-modified polynorbornene represented by the following formula (6) is more preferable.
  • e and f are the number of repeating units, each independently being an integer of 1 or more.
  • the number average molecular weight Mn of the norbornane structure-containing silicone-modified polymer is preferably 50,000 or more, more preferably 100,000 or more, and still more preferably, from the viewpoint of achieving both shrinkage and flex resistance and the effect of improving skin wrinkles. It is 200,000 or more, preferably 2,000,000 or less, more preferably 1.5 million or less, still more preferably 800,000 or less, and still more preferably 600,000 or less.
  • the specific range of the number-average molecular weight Mn of the silicone-modified polymer having a norbornane structure is preferably 50,000 to 2,000,000, more preferably 100,000 to 1,500,000, further preferably 200,000 to 800,000, and still more preferably 200,000 to 800,000. 600,000.
  • the number average molecular weight Mn of the polymer can be measured by gel filtration chromatography (GPC) using polystyrene as a standard substance, and specifically, can be measured by the method described in Examples.
  • the norbornane structure-containing silicone-modified polymer is obtained, for example, by addition-polymerizing a silicone-modified cyclic olefin monomer containing a norbornane structure or capable of forming a norbornane structure by a known method.
  • a cyclic olefin monomer represented by the following general formula (1a) or (2a) is subjected to addition polymerization.
  • a cyclic olefin monomer represented by the following general formula (3a) may be copolymerized.
  • R 1 is each independently an alkyl group having 1 to 12 carbon atoms
  • X is a group represented by the following formula (i).
  • a is an integer of 1 or more and 3 or less
  • b is an integer of 0 or more and 2 or less.
  • R 2 is independently a hydrocarbon group having 1 to 12 carbon atoms
  • c is an integer of 1 to 5 inclusive.
  • R 1 , R 2 and b are the same as described above, and d is an integer of 2 or more and 5 or less.
  • R 3 to R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group and a halogenated carbon atom having 1 to 10 carbon atoms.
  • Two groups selected from R 3 to R 6 may combine with each other to form an alicyclic structure, an aromatic ring structure, a carbimide group or an acid anhydride group. b is the same as described above.
  • the amount thereof is preferably 90 mol%, based on 100 mol% of all the monomers used for the polymerization, from the viewpoint of the effect of improving skin wrinkles.
  • more preferably 70 mol% or less further preferably 50 mol% or less, preferably 5 mol% or more, more preferably 10 mol% or more, and still more preferably 30 mol% or more.
  • the silicone-modified polynorbornene represented by the formula (6) can be obtained by addition-polymerizing tris (trimethylsiloxy) silylnorbornene represented by the following formula (6a) and norbornene.
  • the copolymerization ratio of tris (trimethylsiloxy) silylnorbornene and norbornene is preferably from 20/80 to 90/10 (mol / mol), and more preferably from 30/70 to 80 /. 20 (mol / mol), and more preferably 50/50 to 70/30 (mol / mol).
  • Each of the repeating units represented by the general formulas (1) to (3) and the formula (6) represents a 2,3-addition structural unit of a cyclic olefin monomer as a raw material monomer. Those having 2,7-addition structural units by addition polymerization of the cyclic olefin monomer may be included.
  • a norbornane structure-containing silicone-modified polymer a norbornene / tris (trimethylsiloxy) silylnorbornene) copolymer is preferable, and the INCI name (International Cosmetic Ingredient Dictionary and Handbook, 16th edition, Vol. 2, 2016, p.2274): NORB / TRIS (TRIMETHYLSILOXY) SILYL NORBORNENE COPOLYMER.
  • Examples of commercially available silicone-modified polymers having a norbornane structure include "NBN-30-ID" (a solution of norbornene / tris (trimethylsiloxy) silyl norbornene) copolymer in isododecane manufactured by Shin-Etsu Chemical Co., Ltd.
  • silicone-modified pullulan examples include pullulan having a silicone structure in a side chain. Specifically, from the viewpoint of skin wrinkle improvement effect and versatility, at least a part of hydrogen atoms of OH group in pullulan is used. Silicone-modified pullulan substituted with a group represented by the following general formula (7) is preferred.
  • Z 1 is a single bond or a divalent organic group.
  • R 2 , X and a are the same as described above, and from the same viewpoint, X is preferably a trimethylsiloxy group, and a is preferably 3.
  • Z 1 is preferably a divalent organic group, more preferably a divalent group represented by the following general formula (8) or (9), and A divalent group represented by the formula (9) is more preferable.
  • R 11 is an alkylene group having 1 to 10 carbon atoms, and examples thereof include a methylene group, an ethylene group, a trimethylene group, a propylene group, and a butylene group. From the same viewpoint, among these, an ethylene group, a trimethylene group, and a propylene group are preferable, and a trimethylene group or a propylene group is more preferable.
  • silicone-modified pullulans include “TSPL-30-ID” (a solution of tri (trimethylsiloxy) silylpropylcarbamate pullulan in isododecane) and “TSPL-30-D5” (tri (trimethylsiloxy) manufactured by Shin-Etsu Chemical Co., Ltd. ) A solution of pullulan silylpropylcarbamate in cyclopentasiloxane).
  • silicone structure-containing silicate compound examples include silicate compounds having a silicone structure at a terminal, such as trialkylsiloxysilicic acid, fluorine-modified alkylsiloxysilicic acid, and phenyl-modified alkylsiloxysilicic acid.
  • the alkyl group in the trialkylsiloxysilicic acid preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms, and still more preferably a methyl group, from the viewpoint of skin wrinkle improvement effect and versatility. It is.
  • Specific examples of the trialkylsiloxysilicic acid include trimethylsiloxysilicic acid.
  • Examples of the fluorine-modified alkylsiloxysilicic acid include compounds in which at least a part of the hydrogen atoms of the alkyl group in the trialkylsiloxysilicic acid has been substituted with fluorine atoms. Specific examples thereof include trifluoropropyldimethylsiloxysilicic acid and trifluoropropyldimethyl / trimethylsiloxysilicic acid.
  • Examples of the phenyl-modified alkylsiloxysilicic acid include phenylpropyldimethylsiloxysilicic acid and phenylpropyldimethyl / trimethylsiloxysilicic acid.
  • silicone structure-containing silicate compounds at least one selected from the group consisting of trialkylsiloxysilicic acid and fluorine-modified alkylsiloxysilicic acid is preferred from the viewpoint of skin wrinkle improving effect.
  • Examples of commercially available silicate compounds having a silicone structure include “KF-7312J”, “KF-7312K”, “KF-7312T”, “KF-7312L”, “X-21-5249” manufactured by Shin-Etsu Chemical Co., Ltd.
  • silicone dendrimer examples include a vinyl polymer having a siloxane dendrimer structure in a side chain.
  • the siloxane dendrimer structure is preferably a group represented by the following general formula (10) from the viewpoint of skin wrinkle improvement effect and versatility.
  • R 1 is the same as described above.
  • Z 2 is a single bond or a divalent organic group.
  • R 1 is the same as described above, and R 12 is an alkyl group having 1 to 10 carbon atoms.
  • Z 3 is an alkylene group having 2 to 10 carbon atoms.
  • X i + 1 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group or a group represented by the general formula (11), and a i is an integer of 0 to 3 inclusive.
  • Z 2 is a single bond or a divalent organic group, and is preferably a divalent organic group from the viewpoint of versatility, and is represented by the following general formulas (12), (13), or ( The divalent group represented by 14) is more preferable.
  • R 13 is an alkylene group having 1 to 10 carbon atoms, and examples thereof include a methylene group, an ethylene group, a trimethylene group, a propylene group, and a butylene group. From the viewpoint of versatility, an ethylene group, a trimethylene group, or Propylene groups are preferred.
  • R 14 is an alkyl group having 1 to 10 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and a butyl group. From the same viewpoint, a methyl group is preferable.
  • R 15 is an alkylene group having 1 to 10 carbon atoms, and examples thereof include a methylene group, an ethylene group, a trimethylene group, a propylene group, and a butylene group. From the same viewpoint, an ethylene group is preferable.
  • q is an integer of 0 to 4, and r is 0 or 1.
  • vinyl-based polymer having a siloxane dendrimer structure in a side chain examples include a polymer having a repeating unit derived from a monomer represented by the following general formula (15). Can be In the formula, R 1 and X 1 are the same as described above.
  • Y is a group containing a vinyl bond, for example, a vinyl group, a 2-acryloyloxyethyl group, a 3-acryloyloxypropyl group, a 2-methacryloyloxyethyl group, a 3-methacryloyloxypropyl group, a 4-vinylphenyl group, -Vinylphenyl group, 4- (2-propenyl) phenyl group, 3- (2-propenyl) phenyl group, 2- (4-vinylphenyl) ethyl group, 2- (3-vinylphenyl) ethyl group, allyl group, 5-hexenyl group.
  • a (meth) acryloyl group or a vinyl group is preferable, and a (meth) acryloyl group is more preferable.
  • the vinyl polymer may further include a repeating unit derived from a vinyl monomer other than the monomer represented by the general formula (15).
  • the vinyl-based monomer is a monomer having a group containing a vinyl bond and other than the monomer represented by the general formula (15), and includes, for example, (meth) acrylic acid, alkyl (meth) ) Acrylates, hydroxyalkyl (meth) acrylates, aromatic ring-containing (meth) acrylates, fatty acid vinyl esters, (meth) acrylamide, styrene or derivatives thereof, and the like, and one or more of these can be used.
  • (meth) acrylic monomers such as (meth) acrylic acid, alkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, and aromatic ring-containing (meth) acrylate are preferable.
  • the content of the repeating unit derived from the monomer represented by the general formula (15) in the vinyl-based polymer is preferably based on all repeating units in the vinyl-based polymer from the viewpoint of skin wrinkle improvement effect. Is 0.1% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more. The upper limit is 100% by mass.
  • the vinyl polymer is more preferably an acrylic polymer.
  • a preferred silicone dendrimer is an acrylic polymer having a siloxane dendrimer structure in a side chain (hereinafter, also referred to as “acryl silicone dendrimer”).
  • the acrylic silicone dendrimer is a polymer having a repeating unit derived from a monomer in which Y is a (meth) acryloyl group in the general formula (15), and is a polymer other than the monomer represented by the general formula (15). It may further include a repeating unit derived from a (meth) acrylic monomer.
  • silicone dendrimers examples include "FA 4001 CM CM Silicone Acrylate” (cyclopentasiloxane solution of acrylate-polytrimethylsiloxy methacrylate copolymer) and “FA 4002 ID ID Silicone Acrylate” (acrylate-poly) manufactured by Dow Corning Toray Co., Ltd. Acrylic silicone dendrimer such as trimethylsiloxy methacrylate copolymer in isododecane solution).
  • silicone-modified polynorbornene selected from the group consisting of silicone-modified polynorbornene, silicone-modified pullulan, trimethylsiloxysilicic acid, trifluoropropyldimethyl / trimethylsiloxysilicic acid, and acrylic silicone dendrimer 1
  • silicone-modified polynorbornene selected from the group consisting of silicone-modified polynorbornene, silicone-modified pullulan, trimethylsiloxysilicic acid, and trifluoropropyldimethyl / trimethylsiloxysilicic acid.
  • silicone-modified polynorbornene and silicone-modified pullulan is more preferred, and silicone-modified polynorbornene is even more preferred.
  • the content of the polymer in the composition used in the present invention is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and still more preferably 1% by mass or more from the viewpoint of the effect of improving skin wrinkles. And still more preferably 5% by mass or more.
  • the content of the polymer in the composition is preferably 30% by mass or less, more preferably 25% by mass. The content is more preferably 20% by mass or less, and even more preferably 15% by mass or less.
  • the specific range of the content of the polymer in the composition is preferably 0.1 to 30% by mass, more preferably 0.5 to 25% by mass, still more preferably 1 to 20% by mass, and still more preferably 1 to 20% by mass. To 15% by mass, more preferably 5 to 15% by mass.
  • the composition used in the present invention is further added at 1 atm, 40 ° C., 60% R.S. H. And a volatile oil having a volatility of 14% or more after drying for 30 minutes.
  • the volatile oil is contained, the shrinkage of the polymer during the drying process is accelerated by increasing the drying rate of the composition containing the polymer, and the effect of extending the skin wrinkles and making it inconspicuous by the above-described mechanism is obtained. Is more improved. From the viewpoint of obtaining the above effects, the volatile oil is obtained at 40 ° C. and 60% R.V. H.
  • the upper limit is 100%.
  • the volatility of the volatile oil was determined by placing 0.5 g of a sample in a glass petri dish having a diameter of 40 mm, and applying a pressure of 60% R.V. H. In the environment described above, the sample was allowed to stand at 40 ° C. for 30 minutes and dried. The mass of the sample before drying was W 0 (g), the mass of the sample after drying was W 1 (g), and ⁇ (W 0 ⁇ W 1 ) / W 0 ⁇ ⁇ 100. Note that two or more volatile oils can be used.
  • volatile oil examples include oil agents having at least one selected from the group consisting of hydrocarbon oils and silicone oils and having a volatility in the above range.
  • volatile oils they are selected from the group consisting of isododecane (volatility 33%), hexamethyldisiloxane (volatility 100%), methyltrimethicone, and dimethylpolysiloxane having a kinematic viscosity at 25 ° C of 2 cSt or less.
  • the kinematic viscosity can be measured using, for example, an Ubbelohde viscometer.
  • the volatile oil is more preferably one or more selected from the group consisting of isododecane and hexamethyldisiloxane, and still more preferably hexamethyldisiloxane.
  • the content of the volatile oil in the composition used in the present invention is preferably 1% by mass or more, more preferably 5% by mass or more, further more preferably 10% by mass or more, from the viewpoint of further improving the effect of improving skin wrinkles. More preferably, it is 20% by mass or more, even more preferably 25% by mass or more, even more preferably 35% by mass or more, even more preferably 45% by mass or more, still more preferably 50% by mass or more, and still more preferably 60% by mass or more. % By mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and preferably 99.9% by mass or less from the viewpoint of enhancing the effect of improving skin wrinkles and the degree of freedom of formulation.
  • the specific range of the content of the volatile oil in the composition is preferably 1 to 99.9% by mass, more preferably 5 to 99.5% by mass, still more preferably 10 to 99.5% by mass, and further more. It is preferably 20 to 99.5% by mass, more preferably 25 to 99.5% by mass, still more preferably 35 to 99.5% by mass, still more preferably 35 to 99% by mass, and still more preferably 45 to 99% by mass.
  • composition used in the present invention may appropriately contain, in addition to the above-mentioned components, other components usually blended in cosmetics and the like as long as the object of the present invention is not impaired.
  • components for example, surfactants, water-soluble polymers, antioxidants, ultraviolet absorbers, vitamins, preservatives, pH adjusters, fragrances, plant extracts, humectants, coloring agents, cooling agents, Examples include antiperspirants, bactericides, skin activators and the like.
  • the form of the composition used in the present invention may be any form that can be applied to the skin by application or the like, and examples include a solution, an emulsion, a cream, a lotion, a gel, a pack, a sheet, and a foam.
  • the composition used in the present invention is applied when applied to the skin, from the viewpoint of applying the composition by applying it to the skin and then shrinking the polymer by drying the composition to exhibit the effect of improving skin wrinkles. It is more preferable that it is liquid at 25 ° C.
  • the composition used in the present invention is applied to the skin by application or the like, and then accelerates the shrinkage of the polymer in the step of drying the composition, and from the viewpoint of enhancing the effect of improving skin wrinkles, the water content is reduced.
  • it is small.
  • the content of water in the composition is preferably 15% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less, still more preferably 2% by mass or less, and still more preferably 1% by mass or less.
  • the content is more preferably 0.5% by mass or less, even more preferably 0.1% by mass or less.
  • the composition is applied, for example, by applying the composition to a peripheral portion of a wrinkle.
  • the shape of the skin can be controlled non-invasively by the above-described action mechanism, and wrinkles of the skin can be made inconspicuous.
  • the“ peripheral portion of the skin wrinkle ” is distinguished from the inside of the wrinkle, that is, the concave portion on the skin surface or the concave portion of the streak.
  • the composition containing the polymer by applying the composition containing the polymer to the skin around the wrinkle, when the composition is dried, the skin surface around the wrinkle shrinks together with the shrinkage of the film containing the polymer, and the wrinkles are reduced. Wrinkles are less noticeable because the skin in the affected area is pulled.
  • the application of the composition is not limited to only the wrinkle peripheral portion of the skin and does not prevent application to the inside of the wrinkle.
  • the region to which the composition is applied includes at least a part of a region intersecting with the direction of the wrinkle in the wrinkle peripheral portion.
  • the direction of wrinkles refers to the direction in which the lines run. This is because, by applying the composition to a region that intersects with the direction of the wrinkle, the wrinkled portion of the skin is stretched to make the wrinkle less noticeable.
  • the region intersecting the direction of the wrinkle is preferably a region along the direction of the wrinkle, and the region may be on only one side of the wrinkle or on both sides. In particular, it is more preferable to apply the composition to both sides of the wrinkle. This is because the wrinkles can be made less noticeable by pulling the wrinkled skin from both sides of the wrinkles.
  • Examples of a form in which the composition is applied to a region along the direction of a wrinkle include a form in which the composition is applied to the region in a planar, band, linear, or dot shape, and specifically, 2 to 4 can be exemplified.
  • the area to which the composition is applied preferably includes the area above the wrinkle.
  • the “gravity direction” means a direction in which gravity acts when a person stands upright
  • “upper” means a direction opposite to the gravity direction.
  • FIG. 2 shows a form in which the composition is applied in the form of a sheet or a band to the skin around the wrinkle (legal line).
  • FIG. 2 (a) shows the area above the wrinkle
  • FIGS. 2 (b) and (c) show the wrinkle.
  • the composition was applied to the upper and lower regions sandwiching. From the viewpoint of making the wrinkles less noticeable, as shown in FIG. 2 (c), the areas where the composition is applied are the upper and lower areas sandwiching the wrinkles, and the areas above the wrinkles are more wrinkles. It is more preferable that the area is wider than the lower area.
  • FIGS. 3 (a), 3 (b) and 3 (c) show forms in which the composition is applied linearly to the skin around the wrinkles (law lines), and FIGS. 4 (a) and 4 (b) show the forms of wrinkles (law lines).
  • This is a form in which the composition is applied in the form of dots to the peripheral skin.
  • the composition is applied to the upper and lower regions sandwiching the wrinkle. It is preferable to apply.
  • the amount of the composition used is not particularly limited as long as the effect of making the wrinkles less noticeable is present, but is, for example, 0.01 g or more and 10 g or less.
  • the application method of the present invention preferably includes a step of applying the composition to the periphery of wrinkles on the skin, for example, and a step of drying the composition to shrink the polymer. Due to the drying, the polymer in the composition applied to the skin shrinks, and the shrinking action pulls and stretches the skin around the wrinkles, thereby flattening the uneven shape of the skin surface, and thus making the wrinkles inconspicuous. It works. After drying, the composition may be removed as needed. Alternatively, after applying the composition to the skin and then drying, the composition may be applied over it without removing the composition.
  • a method for improving skin wrinkles which comprises applying a composition containing a polymer having a silicone structure to the skin,
  • the polymer has a deformation ratio of 0.3 or more and 1 or less as measured by the following method (1), and a film of the polymer in a bending resistance test by a cylindrical mandrel method performed by the following method (2).
  • the method according to claim 1, wherein the minimum diameter of the cylindrical mandrel that does not cause cracks is 2 mm or more and 25 mm or less.
  • Method (1) A 10% by mass solution of the polymer in hexamethyldisiloxane is prepared.
  • a solution of 0.005 g of the solution was applied to one side of a polyethylene sheet having a width of 20 mm x a length of 100 mm x a thickness of 0.03 mm in a range of 20 mm in width x 50 mm in length from one end of the short side in the length direction. Dry for 10 minutes in a thermostat set at °C.
  • the length of the polyethylene sheet in the portion to which the solution was applied is L1
  • the length of the polyethylene sheet in the portion deformed by shrinkage after drying is L2
  • the value of L2 / L1 is the deformation ratio.
  • the solution is applied to a polyethylene terephthalate film having a width of 50 mm, a length of 100 mm and a thickness of 0.1 mm using a 200 ⁇ m applicator, and dried in a thermostat set at 40 ° C. for 120 minutes to prepare a test piece.
  • a bending resistance test was performed in accordance with the cylindrical mandrel method specified in JIS K5600-5-1: 1999, and the minimum diameter of the cylindrical mandrel where cracks did not occur in the polymer film on the test piece. Ask for.
  • a method for improving skin wrinkles comprising: applying a composition containing a polymer having a silicone structure to a wrinkle periphery of skin, and then drying the composition to shrink the polymer.
  • the polymer has a deformation ratio of 0.3 or more and 1 or less measured by the method (1), and a film of the polymer in a bending resistance test by a cylindrical mandrel method performed by the method (2).
  • the method according to claim 1, wherein the minimum diameter of the cylindrical mandrel that does not cause cracks is 2 mm or more and 25 mm or less.
  • the polymer is at least one member selected from the group consisting of a norbornane structure-containing silicone-modified polymer, a silicone-modified pullulan, a silicone structure-containing silicate compound, and a silicone dendrimer, and the content of the polymer in the composition is 0.1%.
  • the method according to ⁇ 1> or ⁇ 2>, which is not less than 30% by mass and not more than 30% by mass, and a deformation ratio measured by the method (1) is 0.5 or more and 1 or less.
  • ⁇ 4> The ratio of the deformation ratio [(deformation ratio) / (minimum diameter of the mandrel)] obtained by the method (1) to the minimum diameter (mm) of the mandrel obtained by the method (2) is 0.01 or more and 0.5 or more.
  • ⁇ 5> The method according to any one of ⁇ 1> to ⁇ 4>, wherein the content of the polymer in the composition is 1% by mass or more and 20% by mass or less.
  • ⁇ 6> The method according to any one of ⁇ 1> to ⁇ 5>, wherein the polymer is at least one selected from the group consisting of a silicone-modified polymer having a norbornane structure and a silicone-modified pullulan.
  • the minimum diameter of the cylindrical mandrel in which cracks do not occur in the polymer film is 2 mm or more and 12 mm or less.
  • a deformation ratio measured by the method (1) is 0.85 or more and 1 or less.
  • the ratio of the deformation ratio [(deformation ratio) / (minimum diameter of the mandrel)] determined by the method (1) to the minimum diameter (mm) of the mandrel determined by the method (2) is 0.10 to 0.5.
  • ⁇ 10> The method according to any one of ⁇ 1> to ⁇ 9>, wherein the polymer is a silicone-modified polymer having a norbornane structure.
  • ⁇ 11> ⁇ 10> The method according to ⁇ 10>, wherein the norbornane structure-containing silicone-modified polymer is a silicone-modified polynorbornene represented by the following formula (6).
  • the minimum diameter of the cylindrical mandrel that does not cause cracks in the polymer film is 3 mm or more and 5 mm or less.
  • ⁇ 15> The ratio of the deformation ratio [(deformation ratio) / (minimum diameter of the mandrel)] determined by the method (1) to the minimum diameter (mm) of the mandrel determined by the method (2) is 0.15 or more and 0.4.
  • the polymer is at least one member selected from the group consisting of a silicone-modified polymer containing a norbornane structure and a silicone-modified pullulan, and the content of the polymer in the composition is 1% by mass or more and 20% by mass or less;
  • the deformation rate measured by 1) is 0.85 or more and 1 or less, and in the bending resistance test by the cylindrical mandrel method performed by the method (2), the cylindrical mandrel in which cracks do not occur in the polymer film is obtained.
  • the polymer is at least one member selected from the group consisting of a silicone-modified polymer containing a norbornane structure and a silicone-modified pullulan, and the content of the polymer in the composition is 1% by mass or more and 20% by mass or less;
  • the deformation rate measured by 1) is 0.85 or more and 1 or less, and in the bending resistance test by the cylindrical mandrel method performed by the method (2), the cylindrical mandrel in which cracks do not occur in the polymer film is obtained.
  • the minimum diameter is 2 mm or more and 12 mm or less, and the ratio of the deformation ratio determined by the method (1) to the minimum diameter (mm) of the mandrel determined by the method (2) [(deformation ratio) / (minimum diameter of the mandrel) )] Is 0.10 or more and 0.5 or less, the method according to any one of ⁇ 1> to ⁇ 3>.
  • the polymer is a norbornane structure-containing silicone-modified polymer, the content of the polymer in the composition is 1% by mass or more and 20% by mass or less, and the deformation ratio measured by the method (1) is 0.95 or more.
  • the minimum diameter of the cylindrical mandrel that does not cause cracks in the polymer film is 3 mm or more and 5 mm or less.
  • the polymer is a norbornane structure-containing silicone-modified polymer, the content of the polymer in the composition is 1% by mass or more and 20% by mass or less, and the deformation ratio measured by the method (1) is 0.95 or more.
  • the minimum diameter of the cylindrical mandrel that does not cause cracks in the polymer film is 3 mm or more and 5 mm or less;
  • the ratio of the deformation ratio [(deformation ratio) / (minimum diameter of the mandrel)] obtained by the method (1) to the minimum diameter (mm) of the mandrel obtained in 2) is 0.15 or more and 0.4 or less.
  • ⁇ 20> The polymer is a silicone-modified polynorbornene represented by the following formula (6), and the content of the polymer in the composition is 1% by mass or more and 20% by mass or less, and is measured by the method (1).
  • the deformation ratio is 0.95 or more and 1 or less, and in the bending resistance test by the cylindrical mandrel method performed by the method (2), the minimum diameter of the cylindrical mandrel in which cracks do not occur in the polymer film is 3 mm or more and 5 mm or less.
  • e and f are the number of repeating units, each independently being an integer of 1 or more.
  • the polymer is a silicone-modified polynorbornene represented by the following formula (6), and the content of the polymer in the composition is 1% by mass or more and 20% by mass or less, and is measured by the method (1).
  • the deformation ratio is 0.95 or more and 1 or less, and in the bending resistance test by the cylindrical mandrel method performed by the method (2), the minimum diameter of the cylindrical mandrel in which cracks do not occur in the polymer film is 3 mm or more and 5 mm or less.
  • the ratio of the deformation ratio [(deformation ratio) / (minimum diameter of the mandrel)] determined by the method (1) to the minimum diameter (mm) of the mandrel determined by the method (2) is 0.15.
  • ⁇ 25> The method according to ⁇ 24>, wherein the content of the volatile oil in the composition is from 45% by mass to 99% by mass.
  • ⁇ 26> The method according to any one of ⁇ 1> to ⁇ 25>, wherein the composition is liquid at 25 ° C.
  • ⁇ 27> The method according to any one of ⁇ 1> to ⁇ 26>, wherein the content of water in the composition is 5% by mass or less.
  • ⁇ 29> The method according to ⁇ 28>, wherein the region is a region along a wrinkle direction.
  • ⁇ 30> The method according to ⁇ 28> or ⁇ 29>, wherein the region is on both sides of a wrinkle.
  • ⁇ 31> The method according to any one of ⁇ 27> to ⁇ 30>, wherein the composition is applied to the region in a planar, band, linear, or dot shape.
  • ⁇ 32> The method according to any one of ⁇ 1> to ⁇ 31>, wherein the wrinkle improving method is a method of controlling the shape of the skin in a non-invasive manner by pulling and stretching the skin around the wrinkle by the shrinkage action of the polymer. .
  • the length of the polyethylene sheet in the portion where the solution was applied was L1 (50 mm), and the length of the polyethylene sheet in the portion deformed (curled) by shrinkage after drying was L2.
  • L2 / L1 was calculated, and this value was used as the deformation ratio of the polymer.
  • L2 was the average of the values measured on the two long sides of the polyethylene sheet 1.
  • the diameter of the test piece was 32 mm, 25 mm, 20 mm, 16 mm, 12 mm, 10 mm, Using 8 mm, 6 mm, 4 mm, 3 mm, and 2 mm cylindrical mandrels, the bending resistance test was performed sequentially from a cylindrical mandrel having a large diameter. The test was terminated when cracks occurred in the polymer film, and the minimum diameter (mm) of the cylindrical mandrel where cracks did not occur was defined as the bending resistance value. The smaller this value is, the more excellent the bending resistance is.
  • FIGS. 5 (a) and 6 (a) are photographs of the vicinity of the law line before the composition is applied
  • FIGS. 5 (b) and 6 (b) are the vicinity of the law line after the composition is applied. It is a photograph of a part.
  • FIG. 5 according to the method of Example 1, wrinkles on the statutory line and its peripheral portion became less noticeable, whereas no improvement effect was observed in Comparative Example 1 shown in FIG.
  • the shape of the skin can be controlled non-invasively and wrinkles on the skin can be made less noticeable.

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Abstract

Ce procédé de réduction des rides de la peau consiste à appliquer sur la peau une composition qui contient un polymère ayant une structure de silicone. Ledit polymère a un rapport de déformation de 0,3-1, évalué avec un procédé prescrit (1), et, dans un test de courbure de mandrin cylindrique réalisé avec un procédé prescrit (2), le diamètre minimal du mandrin cylindrique au niveau duquel des fissures ne se produisent pas dans un film dudit polymère est de 2 à 25 mm.
PCT/JP2019/038001 2018-09-28 2019-09-26 Procédé de réduction des rides de la peau WO2020067358A1 (fr)

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JP2013103885A (ja) * 2011-11-10 2013-05-30 Kose Corp 凹凸補正化粧料
US20150016862A1 (en) * 2013-07-15 2015-01-15 The Procter & Gamble Company Applicator for applying compositions that smooth wrinkles and skin texture imperfections
JP2015086150A (ja) * 2013-10-29 2015-05-07 信越化学工業株式会社 シリコーンゴム粒子の水分散液、シリコーンゴム粒子、及び化粧料
JP2017190300A (ja) * 2016-04-13 2017-10-19 株式会社シャネル化粧品技術開発研究所 （ｆ＋ｗ）／ｏ型エマルション及びそれを含む化粧料組成物
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05933A (ja) * 1990-03-19 1993-01-08 Ken Prod Kk しわ伸ばし化粧用液状組成物
JP2005200320A (ja) * 2004-01-14 2005-07-28 Shiseido Co Ltd しわ改善用皮膚外用剤
JP2006169145A (ja) * 2004-12-14 2006-06-29 Kao Corp しわ延ばし剤
JP2009522268A (ja) * 2005-12-30 2009-06-11 エイボン プロダクツ インコーポレーテッド まつげをカールする方法
JP2010229094A (ja) * 2009-03-27 2010-10-14 Shiseido Co Ltd 凹凸補正用皮膚外用剤
JP2011016734A (ja) * 2009-07-07 2011-01-27 Kao Corp 化粧料
JP2011126807A (ja) * 2009-12-16 2011-06-30 Kao Corp 化粧料
US20120087888A1 (en) * 2010-04-12 2012-04-12 Pernodet Nadine A Bio-Mechanical Stimulation Of Collagen Synthesis In Skin Cells And Reduction Of Appearance Of Fine Lines And Wrinkles On The Skin
JP2013103885A (ja) * 2011-11-10 2013-05-30 Kose Corp 凹凸補正化粧料
US20150016862A1 (en) * 2013-07-15 2015-01-15 The Procter & Gamble Company Applicator for applying compositions that smooth wrinkles and skin texture imperfections
JP2015086150A (ja) * 2013-10-29 2015-05-07 信越化学工業株式会社 シリコーンゴム粒子の水分散液、シリコーンゴム粒子、及び化粧料
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JP2018123071A (ja) * 2017-01-30 2018-08-09 信越化学工業株式会社 油中水型化粧料

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