WO2023145469A1 - 化粧料 - Google Patents

化粧料 Download PDF

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Publication number
WO2023145469A1
WO2023145469A1 PCT/JP2023/000635 JP2023000635W WO2023145469A1 WO 2023145469 A1 WO2023145469 A1 WO 2023145469A1 JP 2023000635 W JP2023000635 W JP 2023000635W WO 2023145469 A1 WO2023145469 A1 WO 2023145469A1
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Prior art keywords
imidazolidinone
group
surfactant
water
cosmetic
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PCT/JP2023/000635
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English (en)
French (fr)
Japanese (ja)
Inventor
美佳 吉村
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Shiseido Co Ltd
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Shiseido Co Ltd
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Priority to JP2023576768A priority Critical patent/JPWO2023145469A1/ja
Priority to CN202380015204.XA priority patent/CN118401229A/zh
Priority to US18/719,582 priority patent/US20250143993A1/en
Publication of WO2023145469A1 publication Critical patent/WO2023145469A1/ja
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles

Definitions

  • This disclosure relates to cosmetics.
  • imidazolidinone derivatives have been used in fields such as cosmetics.
  • Patent Document 1 describes skin creams and skin care milky lotions containing imidazolidinone derivatives.
  • the stratum corneum which is the outermost layer of the skin, is highly hydrophobic and has a barrier function that prevents foreign substances from entering from the outside, making it difficult for water-soluble active ingredients applied to the skin to penetrate into the skin. have. Therefore, when the drug is simply applied to the skin, the hydrophilic drug component tends to remain on the skin surface, and sufficient effects cannot be exhibited.
  • imidazolidinone derivatives and their salts have a log P o / w of about -1.5 and are highly hydrophilic, so they are ingredients that are difficult to penetrate the skin.
  • a technology that allows imidazolidinone derivatives and their salts to have a log P o / w of about -1.5 and are highly hydrophilic, so they are ingredients that are difficult to penetrate the skin.
  • the subject of the present disclosure is to provide a cosmetic capable of enhancing the skin permeability of imidazolidinone derivatives and salts thereof.
  • ⁇ Aspect 1> At least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the following formula 1 and salts thereof, and at least one selected from the group consisting of amino acid surfactants and taurine surfactants surfactant, Cosmetics, including: (In Formula 1, R 1 and R 2 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms having 0 to 3 hydroxyl groups, or 0 to 5 It is a cycloalkyl group having 3 to 7 carbon atoms and a hydroxy group.)
  • R 1 and R 2 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms having 0 to 3 hydroxyl groups, or 0 to 5 It is a cycloalkyl group having 3 to 7 carbon atoms and a hydroxy group.
  • the amino acid-type surfactant is an ⁇ -amino acid-type surfactant.
  • ⁇ Aspect 3> The cosmetic according to aspect 1, wherein the surfactant is at least one selected from the group consisting of lauryl betaine, coconut amidopropyl betaine, sodium cocoylglycinate, potassium cocoyl glutamate, and sodium methyltaurate coconut oil. .
  • the imidazolidinone derivative is 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone.
  • ⁇ Aspect 8> A group consisting of an amino acid-type surfactant and a taurine-type surfactant as a percutaneous penetration enhancer for at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the following formula 1 and salts thereof Using at least one surfactant selected from: (In Formula 1, R 1 and R 2 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms having 0 to 3 hydroxyl groups, or 0 to 5 It is a cycloalkyl group having 3 to 7 carbon atoms and a hydroxy group.)
  • said amino acid-type surfactant is an ⁇ -amino acid-type surfactant.
  • ⁇ Aspect 10> Use according to aspect 8, wherein the surfactant is at least one selected from the group consisting of lauryl betaine, coconut amidopropyl betaine, sodium cocoyl glycinate, potassium cocoyl glutamate, and sodium methyl coco taurate.
  • the imidazolidinone derivative is 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone.
  • FIG. 1 is a graph showing the ratio of the cumulative permeation amount of examples containing various transdermal penetration enhancing ingredients to the cumulative permeation amount of Comparative Example 1 or Reference Comparative Example 1 containing no transdermal penetration enhancing ingredient.
  • FIG. 2 is a graph showing the cumulative amount of permeation after 3 hours when using various amino acid-type surfactants and taurine-type surfactants.
  • the cosmetic of the present disclosure comprises at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by formula 1 above and salts thereof (hereinafter sometimes referred to as "specific water-soluble drug”). , and at least one surfactant selected from the group consisting of amino acid-type surfactants and taurine-type surfactants (hereinafter sometimes referred to as "specific surfactant").
  • the specific water-soluble drug of the present disclosure penetrates the pseudo-skin membrane to some extent, as shown in Comparative Example 1 in FIGS. 1 and 2, without the use of drugs known as skin penetration enhancers.
  • the pseudo-skin membrane used in the present disclosure has performance similar to the characteristics of the skin, it can be said that if a drug permeates the pseudo-skin membrane, the drug also permeates the skin.
  • lauryl betaine which is an amino acid-type surfactant
  • niacinamide nicotinamide
  • the permeability to the pseudo-skin membrane that is, the percutaneous permeability can be enhanced.
  • the present inventors found that when used in combination with a specific water-soluble drug, the permeability to the pseudo-skin membrane, that is, the transdermal permeability is improved more than twice as much as that of niacinamide. Found it.
  • any skin penetration enhancer when increasing the skin permeability of a specific water-soluble drug, any skin penetration enhancer is not effective, and among various agents, amino acid type surfactants or taurine type surfactants It is believed that some kind of interaction occurs only when the agents are used in combination, resulting in a specific increase in skin penetration.
  • the cosmetic of the present disclosure comprises at least one water-soluble drug (specific water-soluble drug) selected from the group consisting of imidazolidinone derivatives represented by the above formula 1 and salts thereof, an amino acid-type surfactant, and a taurine-type and at least one surfactant (specific surfactant) selected from the group consisting of surfactants.
  • water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by the above formula 1 and salts thereof, an amino acid-type surfactant, and a taurine-type
  • surfactant specific surfactant
  • the specific water-soluble drug is at least one water-soluble drug selected from the group consisting of imidazolidinone derivatives represented by Formula 1 below and salts thereof.
  • Such agents can exhibit, for example, anti-wrinkle effects, SCCA1 inhibitory effects, etc.:
  • R 1 and R 2 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms having 0 to 3 hydroxyl groups, or 0 to 5 hydroxy is a cycloalkyl group having 3 to 7 carbon atoms having a group.
  • imidazolidinone derivatives include 2-imidazolidinone, 1-methyl-2-imidazolidinone, 1,3 from the viewpoint of further improving skin penetration when used in combination with a specific surfactant.
  • -dimethyl-2-imidazolidinone, 1-(2-hydroxyethyl)-2-imidazolidinone, and 1,3-bis-(2-hydroxyethyl)-2-imidazolidinone At least one is preferred, and 1-(2-hydroxyethyl)-2-imidazolidinone (sometimes referred to as “hydroxyethylimidazolidinone”) is more preferred.
  • the imidazolidinone derivative can be made into an inorganic salt or an organic salt by a known method.
  • Inorganic salts can include, for example, hydrochloride, sulfate, phosphate, hydrobromide, sodium, potassium, magnesium, calcium, and ammonium salts.
  • Organic salts include, for example, acetates, lactates, maleates, fumarates, tartrates, citrates, methanesulfonates, p-toluenesulfonates, triethanolamine salts, diethanolamine salts, and amino acids. Mention may be made of salt.
  • the amount of the specific water-soluble agent is not particularly limited, but from the viewpoint of further improving the penetration into the skin when used in combination with the specific surfactant, it is 0.1% by mass or more with respect to the total amount of the cosmetic, It is preferably 0.3% by mass or more, 0.5% by mass or more, 0.7% by mass or more, 1.0% by mass or more, or 1.5% by mass or more.
  • the upper limit of the compounding amount is not particularly limited, and may be, for example, 10% by mass or less, 8.0% by mass or less, 5.0% by mass or less, or 3.0% by mass or less.
  • the specific surfactant is at least one surfactant selected from the group consisting of amino acid-type surfactants and taurine-type surfactants. Since the specific surfactant can enhance the penetration of the specific water-soluble drug into the skin, it can be used as a percutaneous penetration enhancer for the specific water-soluble drug.
  • amino acid-type surfactant means a surfactant having a structure derived from an amino acid.
  • amino acid is a general term for organic compounds having an amino group and a carboxy group.
  • the amino acid-type surfactant is preferably an ⁇ -amino acid-type surfactant from the viewpoint of further improving skin penetration when used in combination with a specific water-soluble drug.
  • amino acid-type surfactants include lauryl betaine, coconut oil fatty acid amidopropyl betaine, cocoyl glycinate (eg sodium cocoyl glycinate), cocoyl glutamate (eg potassium cocoyl glutamate), 2-alkyl-N- Carboxymethyl-N-hydroxyethylimidazolinium betaine, cocamidopropyl betaine, lauramidopropyl betaine, cocobetaine, cocoamphoacetate (eg sodium cocoamphoacetate), lauroamphoacetate (eg sodium lauroamphoacetate), stearoyl glutamate, myristoyl Glutamate and lauryl glutamate are more preferred. These can be used alone or in combination of two or more.
  • a taurine-type surfactant intends a surfactant having a structure derived from taurine.
  • taurine-type surfactants include surfactants having a structure derived from acyl taurine or acylmethyl taurine (ie, N-acyl-N-methyl taurine).
  • coconut oil fatty acid methyltaurine and salts thereof are preferable from the viewpoint of further improving skin permeability when used in combination with a specific water-soluble drug.
  • salts include alkali metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as calcium salts and magnesium salts; zinc salts; iron salts; ammonium salts; Salts with amino acids; salts with amines such as monoethanolamine, diethanolamine and triethanolamine.
  • alkali metal salts are preferred, and sodium salts are more preferred.
  • the blending amount of the specific surfactant is, for example, 0.05% by mass or more, more than 0.05% by mass, 0.07% by mass or more, 0.1% by mass or more, or 0.05% by mass or more, relative to the total amount of the cosmetic. 8.0% by mass or less, 6.0% by mass or less, 5.0% by mass or less, 3.0% by mass or less, 1.0% by mass or less, 0.7% by mass % by mass or less, 0.5% by mass or less, or 0.3% by mass or less.
  • a specific surfactant can function as a percutaneous penetration enhancer for the above-mentioned specific water-soluble drug. Therefore, from the viewpoint of further improving the skin permeability when used in combination with the specific water-soluble drug, the mass ratio of the specific surfactant to the specific water-soluble drug should be more than 0.05, 0.07 or more, 0.07 or more. It is preferably 10 or more, or 0.15 or more, and 5.0 or less, 4.0 or less, 3.0 or less, 2.0 or less, 1.5 or less, 1.0 or less, 0.70 or less , 0.50 or less, or 0.40 or less.
  • Cosmetics of the present disclosure may contain water.
  • Water is not particularly limited as long as it can dissolve the specific water-soluble drug described above.
  • water used in cosmetics can be used. Examples of such water include ion-exchanged water, purified water, distilled water, ultrapure water, and tap water.
  • the amount of water to be blended there are no particular restrictions on the amount of water to be blended, and for example, it may be appropriately selected according to the formulation employed in the cosmetic (for example, the form of a single aqueous phase, or the form of an oil-in-water or water-in-oil emulsion). can be adjusted. Specifically, the content of water is, for example, 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 45% by mass or more, 50% by mass or more with respect to the total amount of the cosmetic.
  • ⁇ Optional component> The cosmetics of the present disclosure can be appropriately blended with various components as long as they do not adversely affect the effects of the present disclosure.
  • Various components include, for example, surfactants other than the specific surfactants described above (e.g., anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants), thickeners , moisturizing agents, dispersants, water-soluble polymers, film-forming agents, sequestering agents, lower alcohols (e.g., ethanol), polyhydric alcohols (e.g., glycerin), higher alcohols, various extracts, sugars, amino acids, organic amines, Polymer emulsions, chelating agents, UV absorbers, pH adjusters, skin nutrients, vitamins, water-soluble drugs other than the above-mentioned specific water-soluble drugs (e.g.
  • niacinamide buffers, preservatives, antioxidants, Stabilizers, propellants, fillers, cooling agents, pigments, dyes, pigments, perfumes, oils and the like can be mentioned.
  • An arbitrary component can be used individually or in combination of 2 or more types.
  • the cosmetic of the present disclosure can contain an alkylene oxide derivative represented by Formula 2 below. Combining such derivatives with specific surfactants can further improve the skin penetration of specific water-soluble drugs:
  • AO is an oxyalkylene group having 3 to 4 carbon atoms
  • EO is an oxyethylene group
  • m and n are the average number of added moles of an oxyalkylene group and an oxyethylene group, respectively, and 1 ⁇ m ⁇ 70, 1 ⁇ n ⁇ 70.
  • the ratio of oxyethylene groups to the total of oxyalkylene groups having 3 to 4 carbon atoms and oxyethylene groups is 20 to 80% by mass.
  • the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group may be added blockwise or randomly.
  • R a and R b may be the same or different, and each is a hydrocarbon group having 1 to 4 carbon atoms or a hydrogen atom, and the ratio of the number of hydrogen atoms to the number of hydrocarbon groups in R a and R b is 0.15 It is below.
  • AO include an oxypropylene group, an oxybutylene group, an oxyisobutylene group, an oxytrimethylene group, and an oxytetramethylene group. Among them, an oxypropylene group and an oxybutylene group are preferable.
  • the range of m which is the average number of added moles of oxyalkylene groups having 3 to 4 carbon atoms, is preferably 2 ⁇ m ⁇ 20.
  • the range of n which is the average number of added moles of oxyethylene groups, is preferably 2 ⁇ n ⁇ 20.
  • the range of (m+n) is preferably 8 to 100 from the viewpoint of stickiness and the like.
  • EO and AO are added in Formula 2, and they may be added in a block or random manner. When added in blocks, EO and AO may be added in two-stage blocks, or may be added in three-stage or more blocks. EO and AO are preferably added randomly.
  • R a and R b are hydrocarbon groups having 1 to 4 carbon atoms or hydrogen atoms, and may be the same or different.
  • examples of hydrocarbon groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group. Among them, a methyl group and an ethyl group are preferred.
  • Each of R a and R b may be the same hydrocarbon group or a hydrogen atom, a mixture of a hydrocarbon group and a hydrogen atom, or a mixture of different hydrocarbon groups.
  • the ratio Y/X of the number (Y) of hydrogen atoms to the number (X) of hydrocarbon groups in R a and R b is 0.15 or less, preferably 0.06 or less.
  • the alkylene oxide derivative of formula 2 above can be produced by a known method. For example, it can be obtained by subjecting a compound having a hydroxyl group to addition polymerization of ethylene oxide and an alkylene oxide having 3 to 4 carbon atoms, followed by an ether reaction with an alkyl halide in the presence of an alkali catalyst.
  • the amount of the alkylene oxide derivative of formula 2 is not particularly limited. , Also, 20% by mass or less, 17% by mass or less, 15% by mass or less, 13% by mass or less, 10% by mass or less, 8.0% by mass or less, 6.0% by mass or less, 5.0% by mass or less, or It can be 3.0% by mass or less.
  • the mass ratio of the alkylene oxide derivative of formula 2 to the specific water-soluble drug is 0.5 or more, 0.7 or more, 1 .0 or more, 1.5 or more, or 2.0 or more, and preferably 20 or less, 15 or less, 12 or less, 10 or less, or 8.0 or less.
  • the skin permeability of the specific water-soluble drug in the cosmetic of the present disclosure can be evaluated, for example, from the results of the cumulative permeation test described below using a simulated skin membrane.
  • the simulated skin membrane has properties similar to those of skin. Therefore, such cumulative permeation studies can simulate the ability of a drug to permeate the skin.
  • the cosmetic of the present disclosure has a cumulative permeation amount of 5.0 ⁇ g/cm 2 or more, 7.0 ⁇ g/cm 2 or more, or 10.0 ⁇ g/cm 2 after 3 hours in the cumulative permeation test. Above, 13.0 ⁇ g/cm 2 or more, or 15.0 ⁇ g/cm 2 or more can be achieved.
  • the upper limit of the cumulative permeation amount is not particularly limited . can.
  • the cosmetic of the present disclosure is a cosmetic containing a specific surfactant with respect to the cumulative amount of permeation after 3 hours in the cumulative permeation test, relative to the cumulative amount of permeation of a cosmetic that does not contain a specific surfactant.
  • the upper limit of the ratio is not particularly limited, and can be, for example, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9.0 or less, or 8.0 or less.
  • a cosmetic containing no specific surfactant is a cosmetic having substantially the same composition as a cosmetic containing a specific surfactant, except that it does not contain a specific surfactant.
  • substantially means a surfactant that does not act as a skin penetration enhancer (for example, the nonionic surfactant "PPG-13 decyltetradeceth -24”) in a predetermined amount (for example, 0.2% by mass). If the cosmetic does not contain a surfactant, the specific water-soluble drug will be repelled by the simulated skin film and the surface of the skin, and there is a risk that a good comparative experiment cannot be performed. Therefore, it is permissible to add a predetermined amount of a surfactant that does not act as a skin permeation enhancer to cosmetics that do not contain a specific surfactant.
  • the dosage form of the cosmetic of the present disclosure is not particularly limited, but from the viewpoint of skin permeability of a specific water-soluble drug, a single aqueous phase form, or an oil-in-water or water-in-oil emulsion Forms are preferred, and single aqueous phase forms are more preferred.
  • Each of these dosage forms can be appropriately prepared by a conventional method using known materials such as oil, emulsifier and water as necessary.
  • "single aqueous phase” intends a single phase substantially composed of an aqueous phase.
  • oil e.g., oil-soluble ultraviolet absorber
  • oil-soluble ultraviolet absorber is solvated or solubilized by alcohol or the like and is allowed to be slightly incorporated into the aqueous phase, but for example, It is intended not to include oil droplets (emulsified particles) emulsified with a surfactant or the like, such as those included in oil-type emulsion compositions.
  • the form of the cosmetic of the present disclosure is not particularly limited, and for example, forms such as milky lotion, cream, and liquid can be adopted.
  • the product form of the cosmetic of the present disclosure is not particularly limited, and examples include skin care cosmetics such as serums, lotions, moisturizing gels, massage gels, milky lotions, and creams; facial cosmetics such as packs; foundations and eyeshadows.
  • skin care cosmetics such as serums, lotions, moisturizing gels, massage gels, milky lotions, and creams
  • facial cosmetics such as packs; foundations and eyeshadows.
  • Sunscreen cosmetics unsunscreen agents
  • body cosmetics skin cleansers such as makeup removers and body shampoos
  • hair cosmetics such as hair liquids, hair tonics, hair conditioners, shampoos, rinses, and hair restorers shaving cosmetics such as shaving cream, pre-shaving lotion and after-shaving lotion
  • ointments such as shaving cream, pre-shaving lotion and after-shaving lotion.
  • the cosmetic of the present disclosure can be applied to any part of the body, for example, it can be applied to any part on the surface of the skin (body surface).
  • the skin of the face lips, eyes, eyelids, cheeks, forehead, eyebrows, nose, etc.
  • head head
  • ears ears, hands, arms, neck, legs, feet, chest, abdomen, back, etc.
  • the skin also includes nails and the like that have hardened due to changes in the keratin of the epidermis of the skin.
  • a cosmetic method using the cosmetic of the present disclosure includes applying the above-described cosmetic to the skin.
  • the “cosmetic method” means a method of beautifying the skin by applying the cosmetic of the present disclosure to the skin, and a method of surgery, treatment, or diagnosis of a human being. differ.
  • the cosmetics for the beauty method of the present disclosure are not particularly limited, and examples include skin care cosmetics such as serums, lotions, moisturizing gels, massage gels, milky lotions, and creams.
  • Cosmetics can be used individually or in combination of 2 or more types. Moreover, you may use, for example, impregnating a face mask etc. with cosmetics.
  • ⁇ Evaluation of cosmetics> (Cumulative permeation test) Regarding drug permeability, a diffusion cell array system suitable for screening (manufactured by Ikeda Rika Co., Ltd., hereinafter referred to as "diffusion cell") was used to evaluate pseudo-skin membrane permeability of specific water-soluble drugs.
  • a diffusion cell array system with an effective transmission area of 0.785 cm2 was used.
  • a Strat-M (trademark) membrane manufactured by Merck Millipore
  • PBS physiological phosphate buffered saline
  • the receiver cell of the diffusion cell was filled with PBS, and the simulated skin membrane was firmly fixed between the receiver cell and the donor cell using cell clamps so that no air could enter.
  • a diffusion cell was set on a hot plate, the surface temperature of the pseudo-skin film was maintained at about 32°C, which corresponds to the surface temperature of the skin, and the PBS in the receiver cell was stirred with a stirrer bar and conditioned for about 1 hour. rice field.
  • the application of the sample to the simulated skin film was performed with a finite open application assuming actual use.
  • the sample was evenly applied to the simulated skin membrane so that the applied amount was 10 ⁇ g/cm 2 .
  • the PBS was collected from the receiver cell.
  • the amount of specific water-soluble drug in the sampled PBS was quantified to calculate the cumulative permeation amount.
  • Test Example 1 Influence of percutaneous permeability by various components used together with specific water-soluble drug>
  • Test Example 1 the influence of various components used together with a specific water-soluble drug on percutaneous permeability was examined. The results are summarized in Table 1 and FIG. The numerical value of the cumulative permeation amount is the average value of the values obtained by measuring each sample three times.
  • Reference Comparative Example 1 and Reference Example 1 are examples for evaluating the influence of the specific surfactant on other water-soluble drugs that are different from the specific water-soluble drug.
  • Example 1 As is clear from the results in Table 1 and FIG. 1, the composition of Example 1 containing a specific water-soluble drug and a specific surfactant was prepared using a surfactant that does not act as a skin penetration enhancer. As compared with the composition of Example 1, it was confirmed that the penetration of the specific water-soluble drug into the pseudo-skin membrane, that is, the transdermal penetration could be improved by more than two times.
  • the specific surfactant of the present disclosure was added to the other water-soluble drug (niacinamide) not included in the specific water-soluble drug of the present disclosure.
  • the penetration of water-soluble drugs into the simulated skin membrane was only improved by a factor of 1.5. From this result, it can be said that the combination of a specific water-soluble drug and a specific surfactant specifically improves the permeability to the pseudo-skin membrane, that is, the transdermal permeability.
  • Test Example 2 Influence of percutaneous permeability due to difference in blending ratio of specific surfactant>
  • Test Example 2 the influence of percutaneous permeability due to differences in the blending ratio of the specific surfactant was examined.
  • the results are summarized in Table 2.
  • the numerical value of the cumulative permeation amount is the average value of the values obtained by measuring twice for each sample.
  • Table 2 also shows the results of Example 1 and Comparative Example 1 for reference.
  • Examples 2-4 Single aqueous phase compositions of Examples 2 to 4 were prepared in the same manner as in Example 1, except that the amounts shown in Table 2 were changed.
  • Test Example 3 Influence of percutaneous permeability due to difference in mixing ratio of specific water-soluble drug>
  • Test Example 3 the influence of percutaneous permeability due to differences in the mixing ratio of the specific water-soluble drug was examined.
  • the results are summarized in Table 3.
  • the numerical value of the cumulative permeation amount is the average value of the values obtained by measuring twice for each sample.
  • Table 3 also shows the results of Example 1 and Comparative Example 1 for reference.
  • Examples 5-6 and Comparative Examples 7-8 Single aqueous phase compositions of Examples 5-6 and Comparative Examples 7-8 were prepared in the same manner as in Example 1 or Comparative Example 1, except that the blending amounts were changed to those shown in Table 3.
  • Test Example 4 Effect of percutaneous permeability due to differences in the type of specific surfactant>
  • Test Example 4 the effect of different types of specific surfactants on percutaneous permeability was examined. The results are summarized in Table 4 and FIG.
  • the numerical value of the cumulative permeation amount is the average value of the values obtained by measuring each sample three times.
  • Example 7-10 Single aqueous phase compositions of Examples 7 to 10 were prepared in the same manner as in Example 1, except that the components and amounts were changed as shown in Table 4.

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PCT/JP2023/000635 2022-01-26 2023-01-12 化粧料 Ceased WO2023145469A1 (ja)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025115616A1 (ja) * 2023-11-27 2025-06-05 株式会社 資生堂 化粧料

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0953092A (ja) * 1995-08-15 1997-02-25 Kao Corp 液体洗浄剤組成物
JP2014131988A (ja) * 2012-12-03 2014-07-17 Kao Corp 皮膚又は毛髪用洗浄剤組成物
JP2019014690A (ja) * 2017-07-10 2019-01-31 クラシエホームプロダクツ株式会社 洗浄剤組成物
JP2019014709A (ja) * 2017-07-07 2019-01-31 ポーラ化成工業株式会社 皮膚外用組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0953092A (ja) * 1995-08-15 1997-02-25 Kao Corp 液体洗浄剤組成物
JP2014131988A (ja) * 2012-12-03 2014-07-17 Kao Corp 皮膚又は毛髪用洗浄剤組成物
JP2019014709A (ja) * 2017-07-07 2019-01-31 ポーラ化成工業株式会社 皮膚外用組成物
JP2019014690A (ja) * 2017-07-10 2019-01-31 クラシエホームプロダクツ株式会社 洗浄剤組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025115616A1 (ja) * 2023-11-27 2025-06-05 株式会社 資生堂 化粧料

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