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WO2020230691A1 - Composition contenant un céramide et de l'oléate d'isobutyle - Google Patents

Composition contenant un céramide et de l'oléate d'isobutyle Download PDF

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Publication number
WO2020230691A1
WO2020230691A1 PCT/JP2020/018536 JP2020018536W WO2020230691A1 WO 2020230691 A1 WO2020230691 A1 WO 2020230691A1 JP 2020018536 W JP2020018536 W JP 2020018536W WO 2020230691 A1 WO2020230691 A1 WO 2020230691A1
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WIPO (PCT)
Prior art keywords
ceramide
ceramides
oleate
mass
skin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/JP2020/018536
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English (en)
Japanese (ja)
Inventor
沙王里 乾
誠之 飯野
修 坂田
宏樹 大成
和裕 小田
湧太郎 清水
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kose Corp
NOF Corp
Albion Co Ltd
Original Assignee
Kose Corp
NOF Corp
Albion Co Ltd
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Priority to JP2021519393A priority Critical patent/JP7324278B2/ja
Publication of WO2020230691A1 publication Critical patent/WO2020230691A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/42—Amides
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a ceramide-containing composition containing isobutyl oleate, which can be used in cosmetics and external preparations for skin.
  • the present invention also relates to a method for increasing or promoting the penetration of ceramides into the skin using isobutyl oleate.
  • Ceramide is known as a major component of intercellular lipids in the stratum corneum of the skin. Ceramides are a general term for ceramides derived from the skin and substances containing pseudo substances or derivatives of ceramides. It is known that ceramides can play a role as a barrier function that does not evaporate water in the skin by binding to the cornified envelope, which is a protein lining the cell membrane. It is also known that ceramides also have a function of imparting elasticity and elasticity to hair. Deterioration of the barrier function of the skin causes various skin problems such as reducing the water content of the skin to cause fine wrinkles, which can be said to be the initial symptom of skin aging, and reducing the resistance to external factors such as allergens. cause. Therefore, focusing on the useful functions of ceramides, cosmetics and external preparations containing ceramides have been studied.
  • ceramides In order to fully exert the functions of ceramides, it is required to promptly infiltrate an effective amount of ceramides into the living body.
  • ceramides since ceramides have high crystallinity, it may be difficult to stably mix them in cosmetics and external preparations. In particular, it is not easy to stably blend ceramides in emulsified cosmetics. Therefore, so far, a technique has been developed in which ceramides are stably blended and the functionality of the ceramides is enhanced by combining them with various components or devising a manufacturing method.
  • Patent Document 1 discloses an oil-in-water emulsified composition in which ceramides, dextrin fatty acid esters, phospholipids, nonionic surfactants, and higher alcohols or esters are combined. This document discloses a technique for stably blending ceramides. However, it is desired to develop a technique for more effectively penetrating ceramides into the skin and hair.
  • An object of the present invention is to provide a ceramide-containing composition containing isobutyl oleate, which can allow ceramides to permeate into a living body such as skin and hair.
  • the present invention includes, but is not limited to, embodiments listed below.
  • [Item 1] A composition containing ceramides and isobutyl oleate (hereinafter referred to as "the present composition").
  • [Item 2] The composition according to Item 1, which is used for cosmetics.
  • [Item 3] The composition according to Item 2, which is a skin cosmetic or a hair cosmetic.
  • [Item 4] The composition according to any one of Items 1 to 3, wherein the ceramides are human ceramides.
  • [Item 4-1] The composition according to any one of Items 1 to 3, wherein the ceramides are human ceramides or natural ceramides.
  • Ceramides include ceramide NP, ceramide NG, ceramide NS, ceramide EOP, ceramide AS, ceramide AP, ceramide EOS, ceramide NDS, ceramide NH, ceramide ADS, ceramide AH, ceramide EOH, ceramide 2, and ceramide 3.
  • Item 2. The composition according to any one of Items 1 to 4, which is one or more selected from.
  • the content of ceramides is 0.0001 to 50% by mass and the content of isobutyl oleate is 0.001 to 90% by mass with respect to the total mass ratio of the composition.
  • ceramide-containing composition for example, a cosmetic composition
  • isobutyl oleate which can effectively permeate ceramides into a living body such as skin and hair.
  • 3F shows the results for triethylhexanoin. It is an image of fluorescence observation 3 hours after application.
  • 4A shows the results for isobutyl oleate
  • FIG. 4B shows the results for methyl oleate
  • FIG. 4C shows the results for ethyl oleate
  • FIG. 4D shows the results for propyl oleate
  • FIG. 4E shows the results for butyl oleate
  • FIG. 4F shows the results for triethylhexanoin.
  • composition according to the present invention contains ceramides and isobutyl oleate as essential components.
  • Ceramides are a type of sphingolipid and include a group of compounds in which sphingosine and fatty acids are amide-bonded.
  • ceramides have one or more long-chain linear and / or branched alkyl or alkenyl groups in the molecule, and at least two or more hydroxyl groups and one or more amide groups (and / or amino groups). It may be a nonionic amphipathic substance having.
  • the ceramides may be a substance (a kind of so-called ceramide derivative) in which a phosphatidylcholine residue or a sugar residue is bound to the hydroxyl group of the nonionic amphipathic substance.
  • the ceramides used in the present composition may be commercially available, or may be produced by using a generally known synthetic method.
  • Ceramides include ceramides and their derivatives.
  • ceramides include ceramides derived from natural products (for example, ceramides derived from animals (human ceramides, natural ceramides derived from non-human animals (for example, horses)), and ceramides derived from plants), and synthetic methods. Ceramides produced (eg, synthetic ceramides, pseudoceramides (synthetic pseudoceramides), and derivatives thereof) and the like are included, but are not limited thereto.
  • ceramides include human ceramides and natural ceramides.
  • the ceramides may be natural extracts or synthetics.
  • ceramides can be appropriately used in the present composition as long as they are in the usual form of use in the cosmetic composition.
  • ceramides are not particularly limited as long as they are ceramides usually used for cosmetics or external preparations for skin, and examples thereof include sphingosine, phytosphingosine and their long chain fatty acid amides.
  • Specific examples of ceramides include ceramide 1, ceramide 2, ceramide 3, ceramide 3B, ceramide 4, ceramide 5, ceramide 6, ceramide 6I, and ceramide 6II. These are classified as natural ceramides.
  • the number after the ceramide represents the type of ceramide.
  • examples of ceramides include ceramide NP, ceramide NG, and ceramide NS.
  • the alphabetical notation after ceramide represents the combination of fatty acids and sphingoids.
  • ceramides include sphingosine and phospholipid derivatives of phytosphingosine, that is, sphingolipids.
  • sphingolipids include sphingomyelin and phytosphingomyelin.
  • ceramides include glucosylceramide and cerebroside, which are glycosides of the above-mentioned ceramides.
  • ceramides include glycosphingolipids such as gangliosides and glycosphingolipids.
  • the ceramides may be in the form of a mixture of arbitrary mixing ratios of isomers that each ceramide can take, or may be in the form of a specific isomer. These ceramides can be used as one of the above-mentioned specific examples or as a combination of two or more kinds of arbitrary mixing ratios.
  • human ceramides are preferable.
  • the ceramides are not limited to this, but when such ceramides are used, it becomes easy to obtain an increase in the effect inherent in the ceramide (for example, a moisturizing effect).
  • the human ceramide referred to here refers to a component constituting an intercellular lipid in the stratum corneum.
  • Human-type ceramides include, for example, ceramide NP, ceramide NG, ceramide NS, ceramide EOP, ceramide AS, ceramide AP, ceramide EOS, ceramide NDS, ceramide NH, ceramide ADS, ceramide AH, ceramide EOH, ceramide 2, and ceramide 3.
  • ceramides have a plurality of notation methods such as notation by classification by function and origin (for example, ceramide 2) and notation by classification by structure (for example, ceramide NS).
  • the ceramides used in the present composition are not limited by the notation, although there may be overlapping components by a plurality of notation methods for the part.
  • Ceramides can fulfill a barrier function that does not evaporate water from the skin and a function that gives hair firmness and elasticity. Therefore, ceramides can exert a moisturizing effect when used in preparations and applied to skin and hair. In addition, ceramides can exert an atopic improving effect (also referred to as an atopic dermatitis improving effect) in the present composition. In addition, when ceramides permeate into the living body from the outside, they may promote the synthesis of ceramide in the living body. Therefore, ceramides can exert a ceramide production promoting effect. As described above, the ceramides have various functions, but the functions of the ceramides in the present composition are not limited to one or more of the above-mentioned functions, and the functions other than these above-mentioned functions are not limited. May have.
  • Isobutyl oleate is a type of oil agent. Specifically, it is an ester-based oil agent. Isobutyl oleate is an ester of oleic acid and isobutyl alcohol.
  • the isobutyl oleate used in the present composition may be commercially available, or may be produced by a generally known synthetic method, for example, a dehydration reaction between oleic acid and isobutyl alcohol.
  • Isobutyl oleate is also referred to as isobutyl oleate, or 2-methylpropyl (Z) -9-octadecenate.
  • ceramides can easily penetrate into the living body such as skin and hair. That is, the presence of isobutyl oleate makes it easier for ceramide to penetrate the living body than in the absence of isobutyl oleate.
  • the composition may be a composition for increasing or promoting the penetration of ceramides into the skin. Therefore, a large amount of ceramides can penetrate into the living body. In addition, ceramides can rapidly penetrate into the living body.
  • the ceramides can be easily stabilized. That is, since ceramides have high crystallinity, when they are used in preparations such as cosmetics, they tend to precipitate as solids due to crystallization or the like at a normal temperature, that is, at room temperature or at a temperature at which the preparation is stored. Isobutyl suppresses solidification and precipitation. It is presumed that these effects are due to the high miscibility of isobutyl oleate with ceramide.
  • This composition containing ceramides was developed as a result of finding that isobutyl oleate has a better penetration effect of ceramides into the living body than other esters. More specifically, although ethyl oleate and methyl oleate exist as raw materials for cosmetics and the like, the difference in function due to the difference in the structure of their oleic acid derivatives has not been clarified. In the present application, focusing on this point, an undeveloped oleic acid derivative was prepared and its function was evaluated, and the best activity was found in isobutyl oleate, which was developed. As described below, isobutyl oleate increases the affinity of ceramides with intercellular lipids, making them easier to penetrate the skin or hair and stay on the skin surface and in the skin, or in the hair surface and hair. It is considered to be.
  • the above-mentioned ceramide-containing composition preferably has a ceramide content of 0.001 to 20 parts by mass when the content of isobutyl oleate is 1 part by mass.
  • the ceramides and isobutyl oleate have this content ratio, the ceramides are stably blended, and the permeability of the ceramides into the living body is further enhanced.
  • the content of ceramides when the content of isobutyl oleate is 1 part by mass is more preferably 0.005 to 10 parts by mass, 0.01. It is more preferably to 5 parts by mass.
  • the content of ceramides when the content of isobutyl oleate is 1 part by mass may be 0.05 parts by mass or more, or 0.1 parts by mass or more. Further, the content of ceramides when the content of isobutyl oleate is 1 part by mass may be 4 parts by mass or less, 3 parts by mass or less, or 2 parts by mass or less. There may be.
  • the above composition containing ceramides may further contain water as appropriate.
  • water as appropriate.
  • the inclusion of water makes the composition more accessible as a formulation.
  • various compounding components required for the present composition can be easily blended.
  • the content of water can improve the usability of the composition.
  • the ceramides are stabilized and the permeability of the ceramides into the living body is enhanced.
  • the present composition may be a non-aqueous preparation.
  • purified water, distilled water, tap water, groundwater, hot spring water, deep ocean water and the like can be used, but the water is not particularly limited.
  • composition containing ceramides may further contain a surfactant as appropriate.
  • a surfactant makes the composition easier to use as a formulation.
  • various compounding components required for the present composition can be easily compounded.
  • an oil agent or an oil-soluble material can be easily blended.
  • the presence of the surfactant stabilizes the formulation.
  • Specific examples of the surfactant are not particularly limited, and ordinary surfactants used for cosmetics or external preparations for skin can be used. Specific examples of the surfactant will be described later.
  • the present composition containing the above ceramides is preferably in the form of an emulsion.
  • the present composition in the form of an emulsion, it becomes easier to use as a preparation.
  • the ceramides are stabilized and the permeability of the ceramides into the living body is enhanced.
  • the composition may be a non-emulsifying form of the preparation.
  • the emulsification system may be in various emulsification forms such as O / W type (oil-in-water type), W / O type (water-in-oil type), and W / O / W type.
  • an O / W type emulsified form is preferable.
  • this composition containing the above ceramides is a form as a material for blending in a final product.
  • This material can be used as a raw material, semi-finished product or in-process product.
  • This material may consist only of ceramides and isobutyl oleate, or may contain other components.
  • a material containing ceramides and isobutyl oleate can be obtained by mixing ceramides, isobutyl oleate, and if necessary, other components, heating and dissolving the mixture, and then cooling the mixture. .. Heating can be performed within a temperature range in which ceramides and other components are stable. If it can be melted without heating, it may not be heated.
  • This material may be solid or liquid. In the absence of other ingredients, this material can usually be solid. The solid material is crystalline, but strictly speaking it does not have to be crystalline.
  • composition containing ceramides is a material to be blended in a final product
  • water and a surfactant are exemplified as other components, but other components may be described later.
  • This material may be in the form of an emulsion.
  • the ceramide-containing present composition preferably has a ceramide content of 0.0001 to 50% by mass with respect to the total mass ratio of the composition.
  • the content of the ceramides is within this range, the ceramides are easily stabilized in the preparation, and the above-mentioned effects (for example, moisturizing effect) of the ceramides are easily obtained.
  • the composition can be easily used in final products such as cosmetics and external preparations for skin. That is, the content of ceramides in the present composition is preferably 0.0005 to 50% by mass when the total mass of the composition is 100% by mass.
  • the content of ceramides is more preferably 0.0007 to 20% by mass, and even more preferably 0.001 to 10% by mass.
  • the content of ceramides may be 0.01% by mass or more, 0.05% by mass or more, or 0.1% by mass or more. Further, the content of ceramides may be 5% by mass or less, 2% by mass or less, or 1% by mass or less.
  • the ceramide-containing present composition preferably has an isobutyl oleate content of 0.001 to 90% by mass.
  • the content of isobutyl oleate is more preferably 0.002 to 50% by mass, and even more preferably 0.003 to 30% by mass.
  • the content of isobutyl oleate may be 0.01% by mass or more, 0.1% by mass or more, 0.5% by mass or more, or 1 It may be mass% or more.
  • the content of isobutyl oleate may be 20% by mass or less, 10% by mass or less, or 5% by mass or less.
  • the above-mentioned ceramide-containing composition is preferably a cosmetic.
  • a cosmetic that is formulationally stable and has high moisturizing properties can be obtained.
  • This composition containing the above ceramides is particularly preferably a skin cosmetic or a hair cosmetic as a cosmetic.
  • skin cosmetics the permeability of ceramides to the skin can be increased, and a cosmetic having a high moisturizing effect can be obtained.
  • hair cosmetics the permeability of ceramides to the hair can be increased, and a cosmetic that imparts firmness and elasticity to the hair can be obtained.
  • the skin cosmetics are not particularly limited, and can be used as cosmetics for various purposes.
  • lotions, milky lotions, creams, beauty liquids, lotions, gel creams, massage cosmetics, pack cosmetics, hand creams, eye creams, body lotions, body creams, makeup cosmetics, makeup base cosmetics, etc. Is illustrated.
  • the method of using the skin cosmetic include a method of using it with hands, fingers and cotton, a method of impregnating it with a non-woven fabric, and a method of spraying it with a spray or mist.
  • the cosmetic for hair is not particularly limited, and can be used as a cosmetic for various purposes.
  • cosmetics such as hair creams, hair lotions, hair waxes, hair sprays, hair rinses, hair masks, and hair treatments are exemplified.
  • the method of using the hair cosmetic include a method of using it with hands and fingers, and a method of spraying it with a spray or mist.
  • the above composition containing ceramides is an external preparation for skin.
  • the external preparation for skin is not particularly limited, and can be used as an external preparation for skin for various purposes.
  • an external liquid agent, an external gel agent, a cream agent, an ointment agent, a liniment agent, a lotion agent, a hap agent, a plaster agent, a spray agent, an aerosol agent and the like can be mentioned.
  • the external preparation for skin may be a pharmaceutical product or a quasi-drug. Examples of the method of using the external preparation for skin include a method of using it with hands, fingers and cotton, a method of impregnating it with a non-woven fabric, and a method of spraying it with a spray or mist.
  • any surfactant generally used in cosmetics or external preparations for skin can be used.
  • nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants can be mentioned. These surfactants make the formulation more stable and make it easier for the ceramides to exert their functions.
  • the content of the surfactant is preferably 0.001 to 60% by mass when the total mass of the composition is 100% by mass.
  • the content of the surfactant is more preferably 0.01 to 50% by mass, and the content of the surfactant is further preferably 0.1 to 40% by mass.
  • the surfactant is composed of fatty acids such as stearic acid, lauric acid, myristic acid, bechenic acid, isostearic acid and oleic acid and alkaline substances such as sodium, potassium and triethanolamine as anionic surfactants.
  • fatty acids such as stearic acid, lauric acid, myristic acid, bechenic acid, isostearic acid and oleic acid and alkaline substances such as sodium, potassium and triethanolamine as anionic surfactants.
  • examples thereof include fatty acid soaps formed, acylglutamates, alkyl phosphates, polyoxyalkylene-added alkyl phosphates and the like.
  • examples of the cationic surfactant include alkylamine salts, polyamine and alkanolamine fatty acid derivatives, and alkyl quaternary ammonium salts.
  • amphoteric surfactant examples include N-alkylN, N-dimethylaminoacetic acid, lecithin, and phospholipids.
  • nonionic surfactants polyoxyalkylene-modified organopolysiloxane, polyoxyalkyl and alkyl co-modified organopolysiloxane, glycerin-modified organopolysiloxane, polyglycerin-modified organopolysiloxane, glycerin fatty acid ester and its alkylene glycol addition , Polyglycerin fatty acid ester and its alkylene glycol adduct, propylene glycol fatty acid ester and its alkylene glycol adduct, sorbitan fatty acid ester and its alkylene glycol adduct, sorbitol fatty acid ester and its alkylene glycol adduct, polyalkylene glycol fatty acid ester , Citrus fatty acid este
  • the above-mentioned ceramide-containing composition may contain various components that can be blended as cosmetics or external preparations for skin.
  • Such components include, for example, water-soluble components, oil-soluble components, oils, water-soluble polymers, moisturizers, thickeners, powders, pigments, UV absorbers, film-forming agents, pH adjusters, and anti-fading agents.
  • examples include agents, antioxidants, defoamers, beauty ingredients, preservatives, fragrances and the like.
  • composition containing ceramides may or may not contain an oil agent other than isobutyl oleate. It is a preferred embodiment to contain an oil agent other than isobutyl oleate. By containing the oil agent, the usability of the preparation is likely to be improved as compared with the case where isobutyl oleate alone is used as the oil agent.
  • the oil agent does not matter the origin of animal oil, vegetable oil, synthetic oil, etc., or the properties of solid oil, semi-solid oil, liquid oil, volatile oil, etc.
  • the oil agent include hydrocarbons, oils and fats, waxes, hydrogenated oils, ester oils, fatty acids, higher alcohols, silicone oils, fluorooils, lanolin derivatives, oily gelling agents and the like. Be done.
  • Specific examples of the hydrocarbons include liquid paraffin, squalane, petrolatum, polyisobutylene, and polybutene.
  • natural fats and oils include wax, olive oil, castor oil, mink oil, macadamia nut oil and the like.
  • waxes include beeswax and gay wax.
  • ester oils include loginate pentaerythrite ester, cholesterol fatty acid ester, phytosterol fatty acid ester, and dipentaerythrit fatty acid ester.
  • fatty acids include stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, and oleic acid.
  • Higher alcohols include stearyl alcohol, isostearyl alcohol, 2-octyldodecanol, 2-decyltetradecanol, cetyl alcohol, lauryl alcohol, oleyl alcohol, behenyl alcohol, cetearyl alcohol, setostearyl alcohol, cetanol, octyldodecanol, etc.
  • silicone oils dimethylpolysiloxane, methylphenylpolysiloxane, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, trimethylsiloxysilicate, highly polymerizable methylphenylpolysiloxane, methacryl-modified organopolysiloxane, stearyl-modified organopolysiloxane , Oleyl-modified organopolysiloxane, behenyl-modified organopolysiloxane, high-polymerization degree dimethylpolysiloxane, alkoxy-modified organopolysiloxane, fluorine-modified organopolysiloxane, and the like.
  • triethylhexanoin may be used as an oil agent.
  • the oil agent can be used alone or in combination of two or more.
  • ester oils include fatty acid esters.
  • Specific examples of the fatty acid ester include those described above, isopropyl myristate, isononyl isononanoate, cetyl ethylhexanoate, neopentylene glycol di2-ethylhexanoate, and the like.
  • an oleic acid ester other than isobutyl oleate may be used.
  • methyl oleate, ethyl oleate, propyl oleate, isopropyl oleate, butyl oleate can be mentioned.
  • isobutyl oleate is superior in stabilizing ceramides and has higher permeability of ceramides to living organisms than these oleic acid esters. Therefore, oleic acid esters can be used as a supplement.
  • isobutyl oleate may be blended in a larger mass than the total mass of the other oleate esters.
  • the total mass of the oily component that is, the oil agent and the component soluble in the oil agent is preferably 1 to 80% by mass when the total mass in the ceramide-containing composition is 100% by mass. This is one aspect.
  • the content of the oily component is in this range, the preparation can be stabilized and a favorable feeling of use can be obtained.
  • the content of the oily component may be in the range of 2 to 60% by mass or 5 to 50%.
  • the above-mentioned ceramide-containing composition may also contain lower alcohols.
  • examples of such alcohols include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, butyl alcohol and isobutyl alcohol.
  • the use of alcohol makes the formulation easier to use. For example, the solubility of the various components is increased.
  • the above composition containing ceramides can also contain a polyhydric alcohol.
  • the polyhydric alcohol include butylene glycol, propylene glycol, dipropylene glycol, glycerin, and polyethylene glycol.
  • the use of polyhydric alcohols makes the formulation easier to use. For example, the stability of the formulation is increased.
  • the composition can also contain esters of these polyhydric alcohols and fatty acids.
  • the above-mentioned ceramide-containing composition can be produced by mixing the above-mentioned components.
  • ceramides and isobutyl oleate may be mixed in advance to prepare a material containing them, and this material and other components may be mixed to produce the present composition.
  • the ceramides and isobutyl oleate may not be mixed in advance.
  • the material can be appropriately mixed under heating conditions and then cooled to obtain an emulsified composition.
  • a method of mixing a preheated and mixed aqueous component and a preheated and mixed oily component can be used.
  • the method for producing the present composition is not limited to this.
  • the present specification also discloses a method for increasing or promoting the penetration of ceramides into the skin using isobutyl oleate.
  • isobutyl oleate facilitates the penetration of ceramides into the skin.
  • the application method and application means are not particularly limited, but are preferably as described above.
  • composition according to the present invention will be described with reference to Examples, but the present invention is not limited to the Examples.
  • Test Example 1 DSC measurement of ceramide mixture By measuring DSC (Differential Scanning Calorimetry), the affinity (may be said to be compatible or miscible) of the composition containing ceramides and isobutyl oleate was examined. ..
  • Ceramides and isobutyl oleate were mixed at a mass ratio of 1: 3, heated and dissolved, and then cooled to obtain a solid ceramide mixture.
  • ceramide 2 manufactured by Takasago International Corporation
  • the obtained solid was used as a measurement sample, and DSC measurement was performed.
  • the ceramide mixture can be used as a ceramide-containing composition (material).
  • the DSC was measured by using a DSC7000 (manufactured by Hitachi High-Tech Science Corporation) equipped with an electric cooling unit as a measuring device and performing a heating scan at a speed of 5 ° C./min. For the measurement, about 4 mg of the measurement sample was placed on an aluminum pan and sealed. The reference was air. By DSC measurement, the melting point was detected as an endothermic peak.
  • FIG. 1 is a graph showing the results of DSC measurement. From this graph, it can be seen that the endothermic peak of the ceramide mixture is lower than that of the ceramide alone. Specifically, the peak top of the ceramide mixture is about 92 ° C., and the peak top of the ceramide alone is about 107 ° C. That is, it can be said that the ceramide mixture has a lower melting point than the ceramide alone. The decrease in melting point indicates that isobutyl oleate is miscible with ceramide. Therefore, it is suggested that isobutyl oleate makes it difficult for ceramide to crystallize and stabilizes the preparation.
  • Test Example 2 Affinity of ceramide mixture with intercellular lipid
  • IL intercellular lipid
  • S. Yoshida, et al, Chem. Pharm. Bull. , Vol. 65 pseudo-intercellular lipids were prepared based on the description in the literature of pages 134-142 (2017).
  • This pseudo-intercellular lipid was prepared from ceramide 5 (manufactured by Takasago International Corporation), cholesterol (manufactured by Sigma-Aldrich Inc.), and palmitic acid.
  • Pseudo-intercellular lipids are similar to the intercellular lipid components of the stratum corneum of the skin, and by using the pseudo-intercellular lipids, the behavior of the original intercellular lipids can be understood.
  • each sample of ceramide 5, cholesterol, and palmitic acid was weighed in 1 mmol and mixed, and the mixture was completely dissolved in a solvent of chloroform / methanol (volume ratio 2: 1).
  • the solution of the mixture was placed in a flask, the solvent was removed using a rotary evaporator, and then an acetate buffer (pH 5.0, concentration 0.1 M) was added so that the sample concentration became 10 mmol / L. ..
  • This sample solution was incubated in a water bath at 65 ° C. and sonicated with an ultrasonic processor (manufactured by MICROTEC) for 5 minutes. As a result, a pseudo-intercellular lipid-containing solution was obtained.
  • the simulated intercellular lipid-containing solution was stored at room temperature.
  • the simulated intercellular lipid-containing solution was filtered before the test, and the water content of the filtered product was evaporated by natural drying to obtain a simulated intercellular lipid for the test.
  • the ceramide mixture was a mixture obtained by mixing ceramide 2 and each oleic acid ester in the same manner as in Test Example 1.
  • oleic acid ester isobutyl oleate, methyl oleate, ethyl oleate, propyl oleate, butyl oleate, or isopropyl oleate was used.
  • the measurement sample thus obtained was subjected to DSC measurement under the same conditions as in Test Example 1 (however, the sample amount was 8 mg).
  • FIG. 2 is a graph showing the results of DSC measurement
  • Table 1 is a table showing the peak temperature based on the results of DSC measurement. From the graph, it was confirmed that the endothermic peak was between 75 and 90 ° C. for the mixture of the ceramide mixture containing each oleic acid ester and the intercellular lipid. In addition, from the graph, it was confirmed that there is an endothermic peak between 40 and 65 ° C. for the intercellular lipid alone and the mixture of the ceramide mixture and the intercellular lipid. Table 1 shows the specific temperature of the peak top for the two endothermic peaks.
  • the peak at 75 to 90 ° C. is a peak derived from ceramide in the ceramide mixture, and the peak of ceramide is caused by each oleic acid ester as in the result of the ceramide alone and the ceramide mixture in Test Example 1. Since the temperature is shifted to a lower temperature and the peak shift width is larger than that in Test Example 1, it can be seen that each oleic acid ester has an action of mixing ceramide with the intercellular lipid. In particular, the ceramide mixture containing isobutyl oleate has a greater degree of melting point drop than the ceramide mixture of other oleate esters. Therefore, it was confirmed that isobutyl oleate is excellent in a high mixing action of inducing ceramide in the ceramide mixture into the intercellular lipid.
  • the peak at 40 to 65 ° C. is a peak derived from intercellular lipids
  • a ceramide mixture containing an oleic acid ester when used, the peak derived from intercellular lipids is intercellular. It can be seen that the temperature shifts to a lower temperature than when the lipid alone is used.
  • the degree of melting point drop is larger than that of other ceramide mixtures of oleate esters. Therefore, it was confirmed that isobutyl oleate was highly miscible with the intercellular lipid component. It can be said that isobutyl oleate is particularly highly miscible with a component having a peak at 40 to 65 ° C. among the intercellular lipid components, and this component can be a ceramide in the intercellular lipid.
  • isobutyl oleate is highly miscible with ceramide in the ceramide mixture and is highly miscible with the intercellular lipid component, stabilizes the preparation containing ceramide, and easily penetrates the ceramide into the living body. It is suggested to do.
  • Test Example 3 Skin Permeability Test A skin permeability test using fluorescent ceramide was carried out, and the effect of isobutyl oleate on improving the permeability of ceramide to the skin was confirmed.
  • the excised skin extracted from humans was used as a skin sample.
  • This skin sample was cut into a size of 15 mm in length ⁇ 15 mm in width with a surgical knife to prepare a skin piece, and a circle with a diameter of 11 mm was drawn on the skin piece, and this circle was used as the application area of the sample sample.
  • Sample The sample was prepared according to the following composition (the total amount of the composition is 100% by mass).
  • oleic acid ester isobutyl oleate, methyl oleate, ethyl oleate, propyl oleate, or butyl oleate was used.
  • Methyl oleate is an oleate ester having the smallest molecular weight
  • propyl oleate has the same main chain length as an isobutyl group of a propyl group as a substituent
  • butyl oleate has a butyl group as a substituent. It has the same molecular weight as the isobutyl group.
  • Triethylhexanoin is a component widely used as an oil agent.
  • Sample The sample can be used as a ceramide-containing composition.
  • Sample Sample composition (ingredients) (% by mass) Ceramide 2 0.2 Oleic acid ester 15 Surfactant 1 Ethanol 2 1,3-butylene glycol 20 Remaining amount of purified water
  • Fluorescent ceramide is a product in which a fluorescent substituent is introduced into ceramide 2, and is called C6-NBD-ceramide. Fluorescent ceramide produces green fluorescence.
  • PEG-40 stearate was used as the surfactant.
  • the components were first mixed and heated to dissolve. The mixture was then stirred by sonication with a sonicator (manufactured by MICROTEC). An emulsion was obtained by cooling the mixture. This emulsion is a sample sample. When the particle size of the micellar particles of the emulsion was measured with an LS13320 laser Coulter counter manufactured by BECKMAN COOLTER, the particle size was about 700 nm in each case. Thus, a stable emulsion was obtained.
  • FIG. 3 shows the results 1.5 hours after application
  • FIG. 3A is isobutyl oleate
  • FIG. 3B is methyl oleate
  • FIG. 3C is ethyl oleate
  • FIG. 3D is propyl oleate
  • FIG. 3E is butyl oleate
  • 3F is the result for triethylhexanoin.
  • 4A shows the results 3 hours after application, FIG. 4A shows isobutyl oleate, FIG. 4B shows methyl oleate,
  • FIG. 4C shows ethyl oleate
  • FIG. 4D shows propyl oleate
  • FIG. 4E shows butyl oleate, and
  • FIG. 4F shows. Results for triethylhexanoin.
  • Table 2 shows the numerical data of the results of the fluorescence observation image.
  • Table 2 shows the percentage (%) of the area showing fluorescence with respect to the total area in the image. From Table 2, it can be understood that the degree of permeability of isobutyl oleate is large.
  • formulation example The following formulations that can be used as cosmetics were manufactured.
  • the "remaining amount" in the compounding amount (mass%) means that the total amount of the formulations is 100% by mass.
  • the eye cream of Formulation Example 2 had a stable formulation, high moisturizing property, and a good usability.
  • Hydrogenated castor oil 0.2 17. Hydrogenated polyisobutene 0.5 18. Cetyl ethylcaproate 1.5 19. Triethylhexanoin 2.0 20. Isobutyl oleate 0.3 21. Olive fatty acid ethyl 0.2 22. Dimethicone (10 mPa ⁇ s at 25 ° C) 3.5 23. Dimethicone (1 million mPa ⁇ s at 25 ° C) 0.5 24. Dimethiconol (1 million mPa ⁇ s at 25 ° C) 0.5 25. Amodimethicone 0.8 26. Glycerin 1.5 27.
  • Propylene glycol 3.5 28.1,3-butylene glycol 0.5 29.1,3-Propanediol 1.0 30. Tripropylene glycol 0.5 31. Citric acid 0.01 32. Na citrate 0.01 33. Glycine 0.1 34. Lysine dilauroyl glutamate Na 0.1 35. Phosphoryl choline glycol polyacrylate 0.1 36. Fragrance 0.3 37. Remaining amount of purified water
  • LIPIDURE-PMB (manufactured by NOF CORPORATION)
  • LIPIDURE-NR (manufactured by NOF CORPORATION)
  • LIPIDURE-A (manufactured by NOF CORPORATION)
  • LIPIDURE-C (manufactured by NOF CORPORATION)
  • the hair mask of Formulation Example 5 had a stable formulation, high moisturizing property, and a good usability.
  • Dimer dilinoleate di isostearyl / Phytosteryl 0.2 13. Ceramide NS 0.1 14. Pentaerythrityl tetraisosterate 1.0 15. Pentaerythrityl tetraethylcaproate 0.2 16. Hexa (hydroxystearic acid / stearic acid / Rosinic acid) Dipentaerythrityl 0.2 17. Cyclohexane-1,4-dicarboxylic acid bisethoxydiglycol 0.2 18. (Icosanedioic acid / tetradecanedioic acid) Polyglyceryl-10 0.3 19. Isononyl isononanoate 0.5 20.
  • the lotion of Formulation Example 7 had a stable formulation, high moisturizing property, and a good usability.
  • Formulation Example 8 Gel cream (ingredient) (mass%) 1. 1. (Acrylate / alkyl acrylate (C10-30)) Cross polymer 0.05 2. Carbomer 0.3 3. 3. Remaining amount of purified water 4. AMP 0.1 5. BG 0.5 6. Ethanol 50.0 7. Ceramide NP 0.05 8. Isostearic acid 0.5 9. Fragrance 0.05 10. Isobutyl oleate 0.5 11. PEG-50 hydrogenated castor oil isostearate 0.05
  • the gel cream of Formulation Example 8 had a stable formulation, high moisturizing property, and a good usability.

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Abstract

La présente invention concerne une composition contenant un céramide, de l'oléate d'isobutyle étant ajouté dans la composition, et la composition étant apte à entraîner l'infiltration du céramide dans le corps vivant. Selon la présente invention, la composition contient un céramide et de l'oléate d'isobutyle. Il est préférable que la teneur en céramide soit de 0,001 à 20 parties en masse si la teneur en oléate d'isobutyle est d'une partie en masse. Il est préférable que la présente invention soit sous la forme d'une émulsion. La présente invention est de préférence utilisée en tant que préparation cosmétique et, de préférence encore, est utilisée en tant que préparation cosmétique pour la peau ou préparation cosmétique pour les cheveux.
PCT/JP2020/018536 2019-05-10 2020-05-07 Composition contenant un céramide et de l'oléate d'isobutyle Ceased WO2020230691A1 (fr)

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JP2022091391A (ja) * 2020-12-09 2022-06-21 日本メナード化粧品株式会社 ヘアコンディショニング組成物
WO2022158525A1 (fr) * 2021-01-20 2022-07-28 味の素株式会社 Composition cosmétique
JP2022111410A (ja) * 2021-01-20 2022-08-01 味の素株式会社 化粧料組成物
JP2023085101A (ja) * 2021-12-08 2023-06-20 タカラベルモント株式会社 毛髪化粧料
EP4401718A4 (fr) * 2021-09-15 2025-07-30 Ocusoft Inc Onguents de traitement de la peau sèche

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JP2016044167A (ja) * 2014-08-26 2016-04-04 小林製薬株式会社 外用組成物
JP2016166187A (ja) * 2015-03-03 2016-09-15 株式会社コーセー 水中油型乳化化粧料
JP2017178860A (ja) * 2016-03-30 2017-10-05 小林製薬株式会社 Ｏ／ｗ型乳化組成物

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JP2015027977A (ja) * 2012-09-20 2015-02-12 花王株式会社 皮膚又は毛髪用洗浄剤組成物
JP2016044167A (ja) * 2014-08-26 2016-04-04 小林製薬株式会社 外用組成物
JP2016166187A (ja) * 2015-03-03 2016-09-15 株式会社コーセー 水中油型乳化化粧料
JP2017178860A (ja) * 2016-03-30 2017-10-05 小林製薬株式会社 Ｏ／ｗ型乳化組成物

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* Cited by examiner, † Cited by third party
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JP2022091391A (ja) * 2020-12-09 2022-06-21 日本メナード化粧品株式会社 ヘアコンディショニング組成物
JP7597359B2 (ja) 2020-12-09 2024-12-10 日本メナード化粧品株式会社 ヘアコンディショニング組成物
WO2022158525A1 (fr) * 2021-01-20 2022-07-28 味の素株式会社 Composition cosmétique
JP2022111410A (ja) * 2021-01-20 2022-08-01 味の素株式会社 化粧料組成物
JP7721900B2 (ja) 2021-01-20 2025-08-13 味の素株式会社 化粧料組成物
EP4401718A4 (fr) * 2021-09-15 2025-07-30 Ocusoft Inc Onguents de traitement de la peau sèche
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JP2023085101A (ja) * 2021-12-08 2023-06-20 タカラベルモント株式会社 毛髪化粧料

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