Composition

Abstract

Provided is a composition or the like in which the dispersibility of bakuchiol in a water-soluble solvent is improved.　A composition according to the present disclosure contains: bakuchiol; a dissolving agent; and a nonionic surfactant and / or an anionic surfactant.

Description

composition

[0001] The present disclosure relates to compositions.

[0002] Bakuchiol is a natural component found in Psoralea corylifolia, and has been reported to have retinol-like activity. For this reason, various studies have been conducted on the addition of bakuchiol to cosmetics and the like.

[0003] Therefore, a first object of the present disclosure is to provide, for example, a composition in which the dispersibility of bakuchiol in an aqueous solvent is improved.

[0004] A second object of the present disclosure is to provide a composition in which the thermal stability of carotenoids, particularly retinoids, is improved, for example.

[0005] A third object of the present disclosure is to provide, for example, a composition that improves the permeability of bakuchiol through the stratum corneum.

[0006] A fourth object of the present disclosure is to provide, for example, a composition containing bakuchiol that is easy to handle.

[0007] In order to achieve the first objective, the composition of the present disclosure (hereinafter also referred to as the "first composition") contains bakuchiol, a solvent, and a nonionic surfactant and / or anionic surfactant.

[0008] In order to achieve the second object, the composition of the present disclosure (hereinafter also referred to as the "second composition") contains bakuchiol and a carotenoid, and the mass ratio (B:C) of the bakuchiol (B) to the carotenoid (C) is 1:10 to 2:1.

[0009] To achieve the third object, the composition of the present disclosure (hereinafter also referred to as the "third composition") contains liposomes, and the liposomes contain bakuchiol, complex lipids, and sterols.

[0010] To achieve the fourth object, the composition of the present disclosure (hereinafter also referred to as the "fourth composition") contains bakuchiol and silica, and the bakuchiol is supported on the silica.

[0011] The first composition of the present disclosure can provide, for example, a composition in which the dispersibility of bakuchiol in an aqueous solvent is improved.

[0012] The second composition of the present disclosure can provide, for example, a composition in which the thermal stability of carotenoids, particularly retinoids, is improved.

[0013] The third composition of the present disclosure can provide, for example, a composition with improved permeability of bakuchiol through the stratum corneum.

[0014] According to the fourth composition of the present disclosure, for example, it is possible to provide a composition containing bakuchiol that is easy to handle.

[0015] Fig. 1 is a photograph showing the dispersibility in a solvent of the first composition of the present disclosure in Example 1. Fig. 2 is a graph showing the distribution of the average particle size of oil droplets contained in the first composition of the present disclosure in Example 1. Fig. 3 is a photograph showing the stratum corneum permeability of the third composition of the present disclosure in Example 3.

[0016] The present disclosure will be specifically described below using examples. Unless otherwise specified, each disclosure may incorporate the explanations of other disclosures.

[0017] <Definition> In this specification, "bakuchiol" refers to a compound represented by 4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol. It is known that the bakuchiol is extracted from the seeds of Psoralea corylifolia, an annual plant of the legume family. The bakuchiol can also be a compound represented by the following chemical formula (1). The bakuchiol may be, for example, a phenoxide ion. The bakuchiol may also be, for example, esterified.

[0018] As used herein, "surfactant" refers to a compound having a hydrophilic group and a hydrophobic group (lipophilic group). Examples of the surfactant include anionic surfactants, cationic surfactants, zwitterionic surfactants, and nonionic surfactants. The anionic surfactant refers to a surfactant that dissociates into anions in an aqueous solution. The cationic surfactant refers to a surfactant that dissociates into cations in an aqueous solution. The zwitterionic surfactant refers to a surfactant that dissociates into cations or anions in an aqueous solution depending on the pH of the aqueous solution. The nonionic surfactant refers to a surfactant that does not dissociate into ions in an aqueous solution.

[0019] As used herein, "carotenoid" refers to a naturally occurring pigment component and a compound that has antioxidant properties.

[0020] As used herein, "sterols" refers to compounds containing a cyclopentanophenanthrene carbon skeleton.

[0021] In this specification, "oil gel" refers to a gelled oil agent (oily component) thickened with a lipophilic gelling agent. The oil gel can be prepared, for example, by adding an oily gelling agent to an oil agent.

[0022] In this specification, "oil gel particle" means one or more particles composed of oil gel, in which a desired component is dissolved or dispersed in the oil agent of the oil gel.

[0023] As used herein, the term "liposome" refers to a vesicle having a lipid bilayer membrane dispersed in an aqueous solvent.

[0024] In one aspect, the present disclosure provides a composition (hereinafter also referred to as the "first composition") that improves the dispersibility of bakuchiol in an aqueous solvent. As described above, the first composition of the present disclosure is characterized by containing bakuchiol, a solvent, and a nonionic surfactant and / or anionic surfactant, and other components and conditions are not particularly limited.

[0025] It is known that bakuchiol is lipophilic (hydrophobic), and therefore difficult to disperse in aqueous solvent.The present inventors have conducted extensive research and found that bakuchiol can be dispersed in aqueous solvent by combining bakuchiol, a solvent, and a nonionic surfactant and / or anionic surfactant, and more specifically, bakuchiol can be dispersed by forming a complex such as micelles with a nonionic surfactant and / or anionic surfactant, and have established the present disclosure.Therefore, according to the present disclosure, a composition with improved dispersibility of bakuchiol in aqueous solvent can be provided.

[0026] The bakuchiol can be isolated or purified compound, or can be a composition containing bakuchiol.The composition containing bakuchiol can be, for example, the extract containing bakuchiol; the crude product of the extract, the dried product of the extract, the freeze-dried product of the extract, the processed product of the extract such as spray-dried product, etc.The bakuchiol can be prepared by self-preparation or can be commercially available.When using commercially available product, for example, the bakuchiol manufactured by BIB Corporation can be mentioned.

[0027] The extract containing bakuchiol can be produced, for example, by solvent extraction of a plant containing bakuchiol. Examples of plants containing bakuchiol include Psoralea corylifolia and Otholobium pubescens. One or more types of plants may be used. The plant material used for the extraction may be an entire plant or a part of a plant. Examples of plant parts include roots, rhizomes, leaves, stems, whole flowers, or a mixture thereof. The material may be the harvested plant itself, or a processed product obtained by drying and / or pulverizing.

[0028] Examples of the solvent used for extracting bakuchiol include aqueous solvents such as water and buffer solutions; lower alcohols or hydrous lower alcohols such as methanol, ethanol, propyl alcohol, isopropyl alcohol, butanol, and isobutanol; propylene glycol, butylene glycol (e.g., 1,3-butylene glycol, 1,2-butylene glycol, 1,4-butylene glycol, etc., hereinafter the same), 1,5-pentanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, and 1,3,5-pentanetriol. Examples of the solvent include polyhydric alcohols or hydrous polyhydric alcohols such as glycerin (e.g., concentrated glycerin) and polyethylene glycol (e.g., molecular weight of 100 to 100,000); organic solvents such as acetone, ethyl acetate, diethyl ether, dimethyl ether, ethyl methyl ether, dioxane, hexane, acetonitrile, xylene, benzene, chloroform, carbon tetrachloride, phenol, and toluene; and acids (hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, etc.) or alkalis (sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonia, etc.) whose normality has been adjusted appropriately. One of the solvents may be used alone, or two or more may be used in combination.

[0029] Examples of treatments for the treated product include decomposition by adding an acid (hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, organic acid, etc.) or an alkali (sodium hydroxide, calcium hydroxide, ammonia, etc.); fermentation or metabolic conversion by a microorganism; component adsorption using an ion exchange resin, activated carbon, diatomaceous earth, etc.; fractionation using chromatography with various separation modes (ion exchange, hydrophilic adsorption, hydrophobic adsorption, size exclusion, ligand exchange, affinity, etc.); filtration using filter paper, membrane filter, ultrafiltration membrane, etc.; pressurization or decompression; heating or cooling; drying or freeze-drying; pH adjustment; deodorization; decolorization; prolonged static storage; etc. One type of treatment may be performed alone, or multiple types may be performed.

[0030] The content of bakuchiol is, for example, preferably 0.001 to 5% by mass, more preferably 0.01 to 3% by mass, and even more preferably 0.1 to 2% by mass (e.g., 0.2% by mass, 1% by mass) based on the total mass of the first composition of the present disclosure.

[0031] Examples of the solvent (solubilizer) include liquid oils, polyhydric alcohols, etc. Examples of the oils include ester oils, hydrocarbon oils, ether oils, etc.

[0032] Examples of the ester oil include glycerin fatty acid esters. Examples of the glycerin fatty acid ester include triester oils such as triethylhexanoin, glyceryl tri-2-ethylhexanoate, caprylic / capric triglyceride, olive oil, jojoba oil, macadamia nut oil, medfoam oil, castor oil, safflower oil, sunflower oil, avocado oil, canola oil, apricot kernel oil, rice germ oil, and rice bran oil; and glycerin fatty acid triesters such as dipentaerythrityl tetraisostearate. The ester oil is preferably caprylic / capric triglyceride, for example, because of its high safety in human cosmetics and topical application, its excellent versatility in formulation design, and its extremely stable global distribution.

[0033] Examples of the polyhydric alcohol include monohydric alcohols such as ethyl alcohol (ethanol), normal propyl alcohol, and isopropyl alcohol; and dihydric alcohols such as butylene glycol (for example, 1,3-butylene glycol), dipropylene glycol, and propylene glycol. The polyhydric alcohol is preferably butylene glycol because it can improve the dispersibility of oil droplets, which will be described later.

[0034] The content of the solvent is, for example, greater than 0% to 90% by mass, based on the total mass of the first composition of the present disclosure. Since this improves the dispersibility of the bakuchiol, it is preferably greater than 0% to 5% by mass, 10 to 75% by mass, or 25 to 50% by mass. The solvent may be one or more types. In the latter case, the content of the solvent may be the content of one type of solvent or the total content of multiple types of solvents, but the total content of multiple types of solvents is preferred.

[0035] When there are multiple types of solvents, the combination of solvents is preferably, for example, a combination of ester oil and polyhydric alcohol, since this can improve the dispersibility of the bakuchiol, and more preferably a combination of tri(caprylic / capric)glyceryl and butylene glycol.

[0036] Examples of the nonionic surfactant include ethylene oxide condensation type nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene steryl ethers, polyoxyethylene polyoxypropylene alkyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene polyhydric alcohol fatty acid esters, polyoxyethylene hydrogenated castor oils, and polyoxyethylene sorbitan fatty acid esters; polyhydric alcohol ester type nonionic surfactants such as glycol fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, and polyglycerin fatty acid esters; and polyhydric alcohol condensation type nonionic surfactants such as fatty acid alkanolamides and alkyl glycosides. Ethylene oxide condensation type nonionic surfactants are preferred, and polyoxyethylene polyoxypropylene alkyl ethers are more preferred because of their excellent dispersibility. Examples of the polyoxyethylene polyoxypropylene alkyl ethers include polyoxyethylene polyoxypropylene decyltetradecyl ether (e.g., PPG-6 decyltetradeceth-20, PPG-6 decyltetradeceth-30), polyoxyethylene polyoxypropylene cetyl ether, polyoxyethylene polyoxypropylene monobutyl ether, polyoxyethylene polyoxypropylene, hydrogenated lanolin, and polyoxyethylene polyoxypropylene glycerin ether.

[0037] Examples of the anionic surfactant include carboxylic acid-based anionic surfactants such as carboxylates and alkyl ether carboxylates; higher alcohol-based anionic surfactants such as alkyl sulfates and alkyl ether sulfates; sulfonic acid-based anionic surfactants such as acyl isethionates and alkyl sulfonates; peptide-based anionic surfactants such as acyl peptide salts; olefin-based anionic surfactants such as α-olefin sulfonates; amino acid-based anionic surfactants such as acyl sarcosinates, acyl methyl alanine salts, acyl glutamates, acylaspartates, and acyl glycine salts; taurine-based anionic surfactants such as acyl methyl taurines; and lactic acid-based anionic surfactants such as acyl lactates.

[0038] The content of the nonionic surfactant and / or anionic surfactant is preferably, for example, 2 to 20 mass % based on the total mass of the first composition. The surfactant may be one type or multiple types. In the latter case, the content of the surfactant may be the content of one type of surfactant or the total content of multiple types of surfactants, but is preferably the total content of multiple types of surfactants.

[0039] The first composition of the present disclosure may further contain a block copolymer. By including the block copolymer, the first composition of the present disclosure can promote emulsification (emulsion formation) of bakuchiol, thereby improving the dispersibility of the first composition of the present disclosure. The block copolymer is preferably a self-assembling block copolymer (self-assembling block copolymer) because it can further promote the emulsification of bakuchiol. Examples of the block copolymer include polyamino acid-polyethylene glycol copolymers such as oligopeptide-56 amide PEG-75 methyl ether; polylactic acid-polyethylene glycol block copolymers; polylactic acid-polyglycolic acid block copolymers; polysarcosine-polyethylene glycol block copolymers; and polyoxazoline-polysiloxane block copolymers. The block copolymer is preferably a polyamino acid-polyethylene glycol copolymer, more preferably oligopeptide-56 amide PEG-75 methyl ether, because it can impart emulsion stability.

[0040] When the first composition of the present disclosure contains the block copolymer, the content of the block copolymer is, for example, 0.02 to 2% by mass, based on the total mass of the first composition. Because this improves the dispersibility of the bakuchiol, the content is preferably 0.05 to 1.5% by mass, or 0.1 to 1% by mass. The block copolymer may be one type or multiple types. In the latter case, the content of the block copolymer may be the content of one type of block copolymer or the total content of multiple types of block copolymers, but the total content of multiple types of block copolymers is preferred.

[0041] The first composition of the present disclosure may further contain a dispersion medium. For example, when the dispersoid is dissolved in the dispersion medium, the dispersion medium can also be referred to as a solvent (hereinafter the same). Examples of the dispersion medium include aqueous solvents. Examples of the aqueous solvent include purified water, distilled water, ion-exchanged water, pure water, and ultrapure water.

[0042] When the first composition of the present disclosure contains the dispersion medium, the blending amount of the dispersion medium is not particularly limited and can be the remainder of the other components of the first composition. The blending amount of the dispersion medium is, for example, preferably more than 0% by mass to 90% by mass, more preferably more than 0% by mass to 10% by mass, and even more preferably more than 0% by mass to 5% by mass, based on the total mass of the first composition of the present disclosure.

[0043] The first composition of the present disclosure is preferably an oil-in-water (o / w) emulsion. The oil-in-water emulsion is composed of an aqueous dispersible continuous phase and an oily dispersible discontinuous phase, and refers to a state in which oil droplets are dispersed in the aqueous phase. The oil-in-water emulsion contains an aqueous phase as an outer phase, and when applied to the skin, it provides a lighter feeling of compatibility with the skin compared to water-in-oil emulsions, making it suitable for use as a lotion or the like. The emulsion is preferably a nanoemulsion and / or microemulsion. This allows the first composition of the present disclosure to maintain a transparent or translucent appearance. In the present disclosure, the "nanoemulsion" refers, for example, to an emulsion characterized by a dispersion system of micro-sized micelles. In the present disclosure, the "microemulsion" refers, for example, to an emulsion having a fine particle diameter (e.g., several to 100 nm).

[0044] The oil droplets may contain bakuchiol, a solvent, a nonionic surfactant, and / or an anionic surfactant. The average particle size of the oil droplets is, for example, 100 nm or less, and is preferably 10 to 75 nm, and more preferably 20 to 60 nm, because this can improve dispersibility and stability over time. The average particle size of the oil droplets can be measured by dynamic light scattering. Specifically, the average particle size can be determined, for example, using a Malvern Panalytical Zetasizer Nano, by placing a 100-fold diluted target composition in a sample cell within the device and measuring the average particle size distribution of the oil droplets. Note that the measurement is calibrated using standard particles.

[0045] The transmittance (the ratio of the intensity of emitted light to the intensity of incident light) of the first composition of the present disclosure is not particularly limited, but is preferably 50% or more, more preferably 60% or more, and even more preferably 70% or more, because this improves stability over time and aesthetics. The transmittance is measured using a spectrophotometer (cell optical path length: 10 mm, light wavelength: 600 nm). The spectrophotometer may be, for example, a UV-Vis-Near-Infrared Spectrophotometer V-770 (JASCO Corporation).

[0046] The transparency of the first composition of the present disclosure can be evaluated, for example, by its transparency. The transparency can be measured, for example, using a turbidity meter. The lower limit of the turbidity is 0 NTU, more than 0 NTU, and preferably 10 NTU or more. The upper limit of the turbidity is, for example, less than 200 NTU, and preferably less than 150 NTU, since this improves stability over time and aesthetics.

[0047] The first-containing composition of the present disclosure may contain any other ingredient commonly used in cosmetics, such as a moisturizer, a sequestering agent, a neutralizing agent, a pH adjuster, an antioxidant, a preservative, etc.

[0048] The first composition of the present disclosure has improved dispersibility in the solvent. The dispersibility can be evaluated, for example, by evaluating the degree of precipitation (solubility) of the target composition. Specifically, when the degree of precipitation is used as an evaluation, the target composition can be stored for one month and then visually evaluated after storage. In the evaluation, if no precipitation is observed in the target composition, the target composition can be evaluated as having excellent dispersibility in the solvent, i.e., having improved dispersibility.

[0049] The method for producing the first composition of the present disclosure can be, for example, by mixing bakuchiol, the solvent, and the nonionic surfactant and / or the anionic surfactant.The mixing is preferably carried out in the presence of the aqueous solvent.When carried out in the presence of the aqueous solvent, the method for producing the first composition can be, for example, by adding the bakuchiol, the solvent, the nonionic surfactant and / or the anionic surfactant to the aqueous solvent, and then mixing them to the extent that the bakuchiol is dispersed in the resulting liquid.

[0050] The first composition may be prepared so that the bakuchiol forms micelles. In this case, the method for preparing the first composition may refer to, for example, the method described in Example 1. As an example, the method for preparing the first composition includes preparing an oil-in-water emulsion containing bakuchiol, a solvent, and the nonionic surfactant and / or the anionic surfactant in the presence of a dispersion medium such as the aqueous solvent.

[0051] The oil-in-water emulsion can be produced by a known method for dispersing oil in the aqueous solvent. The oil-in-water emulsion can be prepared, for example, by mixing bakuchiol, a solvent, and the nonionic surfactant and / or the anionic surfactant, and then homogenizing or dispersing the mixture in the dispersion medium. The mixing can be performed, for example, by manual shaking, stirring with a stirrer or impeller, or using an ultrasonic vibrator. The mixing temperature is not particularly limited, as long as the mixture can be dispersed. For example, 55 to 80°C is preferred, and 70 to 80°C is more preferred. The mixing time is not particularly limited, as long as the bakuchiol or other components can be dispersed. For example, 0.25 to 2 hours is preferred, and 0.5 to 1 hour is more preferred.

[0052] In the mixing, the optional other component may be added. When the optional other component is a preservative, examples of the preservative include phenoxyethanol.

[0053] The dispersion medium preferably contains, for example, a block copolymer. When the dispersion medium contains the block copolymer, the method for producing the first composition preferably includes mixing the dispersion medium and the block copolymer, and homogenizing or dispersing the block copolymer in the dispersion medium, for example, before, during, or after the formation of the oil-in-water emulsion. The mixing temperature is not particularly limited, as long as the block copolymer can be dispersed in the dispersion medium, and is preferably, for example, 60 to 85°C. The mixing time is not particularly limited, as long as the block copolymer can be dispersed in the dispersion medium, and is preferably, for example, 0.5 to 3 hours.

[0054] After forming the oil-in-water emulsion, the method for producing the first composition preferably includes, for example, a micronization treatment of the oil droplets in the oil-in-water emulsion. By including the micronization treatment in the method for producing the first composition, for example, the dispersibility and temporal stability of bakuchiol in the resulting composition can be further improved. The micronization treatment can be, for example, a nanoparticle treatment in which the oil droplets are reduced to nano-sized particles. The micronization treatment can be carried out using, for example, a known method. The micronization treatment can be carried out, for example, by ultrasonic emulsification using an ultrasonic treatment device, a high-pressure emulsifier, or the like. When the micronization treatment is carried out using a high-pressure emulsifier, the pressure of the micronization treatment is, for example, 20 to 200 MPa, preferably 50 MPa. The number of pressure passes in the nanoparticle treatment is, for example, 1 to 10 passes, preferably 1 to 3 passes. By increasing the pressure and number of passes in the micronization treatment, the average particle size of the oil droplets in the oil-in-water emulsion after the micronization treatment can be relatively reduced. This makes it possible for the method for producing the first composition to further improve, for example, dispersibility, stability over time, transparency (transmittance), and the like, and also to further suppress turbidity.

[0055] The average particle size of the oil droplets can be adjusted, for example, by adjusting the content of bakuchiol, solvent, nonionic surfactant and / or anionic surfactant, etc. relative to the total amount of the first composition of the present disclosure.

[0056] <Second Composition> In another aspect, the present disclosure provides a composition (hereinafter also referred to as the "second composition") in which the thermal stability of a carotenoid is improved. As described above, the second composition of the present disclosure comprises bakuchiol and a carotenoid, and the mass ratio (B:C) of the bakuchiol (B) to the carotenoid (C) is 1:10 to 2:1. The second composition of the present disclosure is characterized by comprising bakuchiol and a carotenoid, and the mass ratio (B:C) of the bakuchiol (B) to the carotenoid (C) is 1:10 to 2:1, with other configurations and conditions not being particularly limited. The second composition of the present disclosure can, for example, improve the thermal stability of a carotenoid. The description of the first composition of the present disclosure can be applied to the second composition of the present disclosure.

[0057] Retinol is known to be unstable and easily decomposed due to heat and other factors. As a result of extensive research, the present inventors have developed a composition combining bakuchiol and a carotenoid in a specific ratio, and have found that the carotenoid, particularly the retinoid, contained in the composition has higher thermal stability than the retinoid alone, leading to the establishment of the present disclosure. Therefore, the present disclosure provides a composition in which the thermal stability of the carotenoid, particularly the retinoid, is improved.

[0058] Examples of the carotenoid include carotenes such as β-carotene, α-carotene, and lycopene; xanthophylls such as lutein, canthaxanthin, β-cryptoxanthin, astaxanthin, zeaxanthin, fucoxanthin, violaxanthin, lycopene, crocin, and capsanthin; and apocarotenoids such as retinol, bixin, norbixin, and crocetin. The α-carotene, β-carotene, and β-cryptoxanthin are vitamin A precursor (provitamin A) carotenoids and can be converted to retinol (vitamin A) in the body. The vitamin A precursor carotenoid and retinol can also be referred to as retinoids. The carotenoids include carotenoid degradation products. Since the retinoids are produced by, for example, degradation of the carotenoids in the body, they can also be referred to as carotenoid degradation products.

[0059] Examples of the retinoid include retinol (vitamin A), retinal (vitamin A aldehyde), retinoic acid (vitamin A acid), retinol propionate, retinol acetate, retinol linoleate, and retinol palmitate.

[0060] The second composition of the present disclosure preferably contains the bakuchiol (B) and the carotenoid (C) in a mass ratio (B:C) of 1:10 to 2:1. The mass ratio (B:C) is more preferably 1:4 to 1:2, or 1:2 to 2:1, because this further improves thermal stability.

[0061] The content of bakuchiol is preferably 0.001 to 5% by mass, 0.01 to 2.5% by mass, or 0.1 to 1% by mass, based on the total mass of the second composition.

[0062] The content of the carotenoid is preferably, for example, 0.001 to 5 mass %, 0.01 to 2.5 mass %, or 0.1 to 1 mass %, based on the total mass of the second composition.

[0063] The second composition of the present disclosure may further contain an oil. Examples of the oil include liquid oils and fats, ester oils, silicone oils, hydrocarbon oils, higher alcohols, fatty acids, etc., used in external compositions such as cosmetics. The oil is preferably silicone oil, since it can impart a moist and smooth feeling to the skin as well as good compatibility with the skin when made into an oil gel composition described below. Furthermore, the oil is preferably hydrocarbon oil, since it can impart a moist feeling to the skin as well as good compatibility with the skin when made into an oil gel composition described below.

[0064] Examples of the liquid oils and fats include liquid oils and fats derived from animals and plants, such as linseed oil, camellia oil, macadamia nut oil, corn oil, olive oil, avocado oil, camellia oil, castor oil, safflower oil, apricot kernel oil, cinnamon oil, jojoba oil, grape oil, sunflower oil, almond oil, rapeseed oil, sesame oil, wheat germ oil, rice germ oil, rice bran oil, cottonseed oil, soybean oil, peanut oil, tea seed oil, evening primrose oil, egg yolk oil, and liver oil. The liquid oils and fats to be used may be synthetic products or commercially available products. When a commercially available product is used, examples thereof include DHA-55 (manufactured by Maruha Nichiro Co., Ltd.), safflower oil (manufactured by Nisshin Oillio Co., Ltd.), Oryza salad oil (manufactured by Oryza Oil & Fat Chemical Co., Ltd.), edible olive oil (manufactured by J-Oil Mills Co., Ltd.), linseed oil S (manufactured by Nippon Flour Mills Co., Ltd.), and Coconard ML (manufactured by Kao Corporation).

[0065] Examples of the ester oil include isononanoic acid esters such as isononyl isononanoate; octanoic acid esters such as cetyl octanoate; isooctanoic acid esters such as glycerin tri-2-ethylhexanoate and pentaerythritol tetra-2-ethylhexanoate; lauric acid esters such as hexyl laurate; myristates such as isopropyl myristate and octyldodecyl myristate; palmitic acid esters such as octyl palmitate; stearic acid esters such as isocetyl stearate; isostearic acid esters such as isopropyl isostearate; isopalmitic acid esters such as octyl isopalmitate; oleic acid esters such as isodecyl oleate; adipic acid diesters such as diisopropyl adipate; sebacate diesters such as diethyl sebacate; and diisostearyl malate. The ester oil is preferably isononyl isononanoate, for example, because when made into an oil gel composition described below, it has softness when crushed on the skin and can impart a transparent appearance and a moist feeling to the oil gel composition.

[0066] Examples of the silicone oil include chain silicones such as dimethylpolysiloxane, methylphenylpolysiloxane, and methylhydrogenpolysiloxane; cyclic silicones such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane; amino-modified silicone oil, polyether-modified silicone oil, carboxy-modified silicone oil, alkyl-modified silicone oil, ammonium salt-modified silicone oil, and fluorine-modified silicone oil.

[0067] Examples of the hydrocarbon oil include liquid paraffin, squalane, squalene, pristane, isoparaffin, α-olefin oligomer, and petrolatum.

[0068] Examples of the higher alcohol include behenyl alcohol, cetyl alcohol, stearyl alcohol, myristyl alcohol, cetostearyl alcohol, isostearyl alcohol, monostearyl glycerin ether (batyl alcohol), lauryl alcohol, hexadecyl alcohol, octyldodecanol, oleyl alcohol, 2-decyltetradecynol, lanolin alcohol, etc. Of the higher alcohols, octyldodecanol is preferred because, when made into an oil gel composition described below, it has softness when crushed on the skin and can impart a transparent appearance and a moist feeling to the oil gel composition.

[0069] Examples of the fatty acids include oleic acid, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, linoleic acid, arachidonic acid, lauric acid, myristic acid, palmitic acid, and stearic acid.

[0070] The oil may be, for example, a solid or liquid at room temperature. One type of oil may be used alone or in combination of two or more types.

[0071] When the second composition is an oil gel composition described below, the oil agent is preferably a composition having a high proportion of liquid oil agent, for example, from the viewpoint of imparting softness to the oil gel, transparency of the appearance, adjustment of the IOB value, etc., and one type or a combination of multiple types can be contained in the oil gel depending on the specific purpose.

[0072] When preparing the transparent oil gel composition, it is preferable to use an oil agent that has a refractive index close to that of water (1.333) and a predetermined balance of organic and inorganic properties. Among the physicochemical properties of the oil agent, properties primarily due to van der Waals forces are referred to as "organic." Properties primarily due to electrical affinity are referred to as "inorganic." Therefore, the properties of the oil agent can be evaluated by evaluating the compound based on the combination of "organic" and "inorganic." Specifically, with regard to the "organic" and "inorganic" properties of the oil agent, each compound in the oil agent is assigned a unique characteristic value, known as an organic value (OV) or an inorganic value (IV). By comparing and adjusting the organic and inorganic values ​​of each compound, an oil agent suitable for a transparent oil gel composition can be selected.

[0073] The upper limit of the IOB value of the oil agent is preferably 0.85 or less, more preferably 0.84 or less, and even more preferably 0.83. The IOB value represents the ratio of inorganic value to organic value (Inorganic Organic Balance) calculated based on the Organic Conceptual Diagram (Fujita, Atsushi, Prediction of Organic Compounds and Organic Conceptual Diagram, Chemistry Vol. 11, No. 10 (1957), pages 719-725), and is calculated by dividing the inorganic value by the organic value. When multiple oil agents are contained, the IOB value of the oil agent after mixing can be calculated as a weighted average of the IOB values ​​of each oil agent. When the IOB value of the oil agent after mixing is 0.85 or less, the second composition can achieve the moist feeling characteristic of an oil gel. The IOB value may be 0, as in the case of squalane, a hydrocarbon oil, but is preferably greater than 0, more preferably 0.01 or more, and even more preferably 0.015 or more.

[0074] The oil solution may further contain oil-soluble dyes (e.g., Red 225), organic pigments (e.g., Orange No. 204, Red No. 202), lakes of coloring matter (e.g., Orange No. 205, Yellow No. 4, Blue No. 1) (lakes with zirconium, barium, aluminum, etc.), natural coloring matter (e.g., chlorophyll, β-carotene), inorganic pigment powders such as yellow iron oxide, red iron oxide, black iron oxide, titanium oxide, and zinc oxide (hydrophobized products are preferred), pearl pigments such as titanium mica, glitter agents made of colored plate-like resins, and the like.

[0075] When the second composition of the present disclosure contains the oil, the content of the oil is, for example, 50% by mass or more, preferably 55% by mass or more, and more preferably 60% by mass or more, based on the total mass of the second composition. The content of the oil is, for example, 99% by mass or less, preferably 98.5% by mass or less, and more preferably 98.1% by mass or less, based on the total mass of the second composition. When the second composition is an oil gel composition described below, the content of the oil is based on the total mass of the oil gel composition.

[0076] The second composition of the present disclosure may further contain a gelling agent. The gelling agent is, for example, a component that gels an oily agent in a transparent to translucent state, has the effect of imparting viscosity over a wide range, and improves stability over time and the feel when applied to the skin. Examples of the gelling agent include dextrin fatty acid esters, inulin fatty acid esters, and amino acid-based oil gelling agents.

[0077] The dextrin fatty acid ester is, for example, an ester of dextrin with a fatty acid or a fatty acid derivative, preferably an ester of dextrin with a higher fatty acid having 8 to 22 carbon atoms. The average degree of glycopolymerization of the dextrin is preferably 3 to 150, and the degree of fatty acid substitution per glucose unit of the dextrin is preferably 1.5 to 1.7. Examples of the dextrin fatty acid ester include dextrin octanoate, dextrin laurate, dextrin palmitate, dextrin myristate, dextrin stearate, dextrin behenate, coconut oil fatty acid dextrin, and (palmitate / octanoate) dextrin. The dextrin fatty acid ester may be a synthetic product or a commercially available product. Commercially available products of the dextrin fatty acid ester include, for example, "Leopearl KL2," "Leopearl MKL2," "Leopearl TT2," and "Leopearl TL2" (manufactured by Chiba Flour Mills Co., Ltd.).

[0078] The inulin fatty acid ester is, for example, an ester of inulin and a fatty acid or a fatty acid derivative, preferably an ester of inulin and a linear or branched, saturated or unsaturated fatty acid having 8 to 32 carbon atoms, and the average molecular weight of the inulin is preferably 300 to 10,000. The inulin fatty acid ester may be a synthetic product or a commercially available product. Specific examples of the inulin fatty acid ester include those described in JP-A-3-197409 and JP-A-2002-193732, and commercially available products include "Leopearl ISK2" (manufactured by Chiba Flour Milling Co., Ltd.).

[0079] Examples of the amino acid oil gelling agent include dibutyl lauroyl glutamide and dibutyl ethylhexanoyl glutamide. The amino acid oil gelling agent may be a synthetic product or a commercially available product. Examples of commercially available amino acid oil gelling agents include "Amino Acid Oil Gelling Agent GP-1" and "Amino Acid Oil Gelling Agent EB-21" (manufactured by Ajinomoto Co., Inc.).

[0080] The gelling agent may be used, for example, alone or in combination of two or more kinds.

[0081] When the second composition of the present disclosure contains the gelling agent, the content of the gelling agent is, for example, 0.5% by mass or more, preferably 1% by mass or more, and more preferably 1.5% by mass or more, based on the total mass of the second composition. Furthermore, the content of the gelling agent is, for example, 50% by mass or less, preferably 45% by mass or less, and more preferably 40% by mass or less, in order to prevent the second composition from becoming too hard.

[0082] The second composition of the present disclosure may further contain a surfactant. The same description as for the first composition of the present disclosure can be applied to the surfactant. When the second composition is an oil gel composition as described below, the surfactant can improve the feel of the second composition when applied and the solubility of added ingredients, for example, when oil gel particles as described below are blended into aqueous cosmetics or the like.

[0083] When the second composition of the present disclosure contains the surfactant, the content of the surfactant is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, and more preferably 1% by mass or more, based on the total mass of the second composition of the present disclosure. Also, the content of the surfactant is 5% by mass or less, preferably 4% by mass or less, preferably 3% by mass or less, and more preferably 2% by mass or less.

[0084] When the second composition of the present disclosure contains the surfactant, the combined HLB value of the oil and the surfactant is preferably 8.5 or less. The HLB value represents the degree of hydrophilicity or lipophilicity (hydrophobicity) of a surfactant and refers to the HLB value at 25°C as defined by Griffin. The Griffin HLB value is defined in J. Soc. Cosm. Chem., 1954, 5:249-256. Furthermore, the concepts of organic and inorganic values ​​of oils in the organic conceptual diagram are highly correlated with the concepts of hydrophilicity and lipophilicity in the HLB method. When the value calculated from the ratio of the organic value to the inorganic value (IV / OV = IOB (Inorganic Organic Balance)) is compared with the HLB value, the approximate formula HLB value = IOB value × 10 holds.

[0085] In the present disclosure, the "blended HLB value" refers to the HLB value of a mixture of one or more types of oils and one or more types of surfactants when the oils and surfactants are used. The blended HLB value is a weighted average of the HLB values ​​of each oil and surfactant based on their mass ratio, and is calculated by the following formula (1): Blended HLB value = Σ (10 × IOBx × Wx) / Σ Wx (HLBy × Wy) / Σ Wy (1) IOBx: IOB value of oil X Wx: mass (g) of oil X HLBy: HLB value of surfactant Y Wy: mass (g) of surfactant Y

[0086] The mixed HLB value may be, for example, 0, but from the viewpoint of making the oil gel particles described below more compatible with water when used in an aqueous cosmetic formulation, the mixed HLB value is preferably greater than 0, more preferably 0.1 or more, and even more preferably 0.15 or more. Furthermore, since the second composition of the present disclosure can form particles without emulsifying, the mixed HLB value is preferably 8.5 or less, more preferably 8.4 or less, and even more preferably 8.3 or less.

[0087] The second composition of the present disclosure may further include a dispersion medium. Examples of the dispersion medium include an aqueous solvent. Examples of the aqueous solvent include purified water, distilled water, ion-exchanged water, pure water, and ultrapure water.

[0088] When the second composition of the present disclosure contains the dispersion medium, the amount of the dispersion medium is not particularly limited and can be the remainder of the other components of the second composition. The amount of the dispersion medium is, for example, preferably 50 to 80 mass % based on the total mass of the second composition of the present disclosure.

[0089] The second composition of the present disclosure preferably contains, for example, particles, and the particles preferably contain the bakuchiol and the carotenoid. The shape of the particles is preferably, for example, spherical. Examples of the spherical shape include a perfect sphere and a sphere with an oval cross section, with perfect spheres being preferred. When the second composition of the present disclosure contains a gelling agent and forms particles, the particles can also be referred to as oil gel particles. By forming the second composition of the present disclosure as oil gel particles, the second composition can be applied efficiently as a skin agent to areas where skin problems such as rough skin, dullness, and blemishes are observed.

[0090] The lower limit of the average particle size of the particles is preferably 100 μm or more, more preferably 125 μm or more, even more preferably 150 μm or more, and even more preferably 175 μm or more. The upper limit of the average particle size of the particles is, for example, 2000 μm or less, preferably 1500 μm or less, and more preferably 1000 μm or less. The average particle size of the particles can be measured, for example, by a sieve method. For example, the sieve method can be performed by wet-classifying 100 g of the particles in water using sieves with various mesh sizes, removing excess water with filter paper, measuring the mass, and measuring the weight-average particle size as the average particle size.

[0091] From the viewpoint of improving the feel during use, the compressive breaking strength of the particles is preferably, for example, 50 kPa or less. The compressive breaking strength of the particles is preferably 0.15 kPa or more, more preferably 0.20 kPa or more, and even more preferably 0.25 kPa or more. From the viewpoint of good spreadability and compatibility on the skin when applied to the skin and enabling the particles to disintegrate smoothly, the compressive breaking strength of the particles is more preferably 40 kPa or less, and even more preferably 30 kPa or less. The compressive breaking strength means the maximum stress at which a gel sample breaks when a compressive load is applied to the gel sample. The compressive breaking strength is the value (kPa (N / m)) obtained by dividing the compressive force when a uniaxial load is applied to a spherical gel sample by the cross-sectional area perpendicular to the axis. ２)). The compressive breaking strength is also called compressive breaking stress, and can be measured by a known method using a known measuring device. An example of a compressive breaking strength measuring device is a compression tester (Rheo Meter: CR-3000EX) manufactured by Sun Scientific Corporation.

[0092] The thermal stability of the carotenoid can be evaluated, for example, by using the abundance (recovery) of the carotenoid in the target composition before and after heat treatment as an evaluation index. Specifically, the second composition of the present disclosure is heat-treated at 110°C for 30 minutes, and the carotenoid contained in the second composition of the present disclosure after the heat treatment is quantified. As a control, a composition prepared in the same manner as the second composition of the present disclosure except that bakuchiol is not added is heat-treated at 110°C for 30 minutes, and the control composition after the heat treatment is quantified. After the quantification, the carotenoid abundance (recovery) in the target composition can be evaluated by determining whether it has increased compared to the control group. In the evaluation, the thermal stability of the carotenoid in the target composition can be evaluated as improved if the carotenoid abundance (recovery rate) in the second composition of the present disclosure after the heat treatment is 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, 95% or more, or 99% or more, based on the abundance (recovery rate) in the second composition of the present disclosure when bakuchiol is not contained. The carotenoid can be quantified, for example, by absorbance measurement. The absorbance measurement can be performed, for example, by the method described in Japanese Patent Publication No. 6,575,987. The carotenoid may be quantified immediately after the heat treatment or 10 days after the heat treatment. When the carotenoid is a retinoid, the thermal stability of the retinoid can be evaluated by, for example, quantifying vitamin A, specifically, using Vitamin A Quantitation Method 1-1 or the like.

[0093] The second composition of the present disclosure can also be referred to as, for example, an oil gel composition or an oily solid composition.

[0094] The second composition of the present disclosure can be produced, for example, by mixing the bakuchiol and the carotenoid. The bakuchiol is typically liquid. Therefore, the second composition can be produced, for example, by adding the carotenoid to the bakuchiol and then mixing. The mixture can be prepared, for example, by mixing the bakuchiol and the carotenoid and homogenizing or dispersing them in the dispersion medium. The mixing can be performed, for example, by manual shaking, stirring with a stirrer or impeller, or using an ultrasonic vibrator. The mixing temperature is not particularly limited, as long as it is a temperature at which the mixture of bakuchiol and the carotenoid can be mixed, preferably uniformly mixed. For example, 20 to 30°C is preferred, and 23 to 25°C is more preferred. The mixing time is not particularly limited, as long as it is a time at which the mixture can be uniformly mixed. For example, 5 minutes to 1 hour is preferred.

[0095] When the second composition is an oil gel composition, the method described in Example 2 can be referred to for the method of producing the second composition. When the second composition is an oil gel composition, the mixture may contain, for example, an oil agent and / or a gelling agent. When the mixture contains the oil agent and / or gelling agent, the oil agent and / or gelling agent may be prepared by mixing an oil agent and a gelling agent, or the oil agent alone or the gelling agent alone may be added. Furthermore, when the mixture contains the oil agent and / or gelling agent, the oil agent and / or gelling agent may be added during the preparation of the mixture, or may be added before or after the preparation of the mixture.

[0096] When the second composition is an oil gel composition, the method for producing the second composition preferably includes, for example, subjecting the mixture to heat treatment (heat treatment) after mixing. This allows the bakuchiol and the carotenoid to be uniformly dispersed in the oil gel composition. The heating temperature is, for example, 80 to 130°C, preferably about 110°C. The heating time is, for example, 10 minutes to 2 hours, preferably about 30 minutes. The method for producing the second composition may include, for example, cooling the heat-treated mixture after the heat treatment. The cooling is, for example, preferably performed by cooling the mixture to a temperature of 20 to 30°C, more preferably to 23 to 25°C.

[0097] In the method for producing the second composition, for example, after the heat treatment, the heat-treated mixture may be added to a dispersion medium such as the water-soluble solvent as a dispersion liquid. This allows, for example, the oil gel composition to form particles, thereby producing the oil gel particles, in the method for producing the second composition. The addition is preferably carried out, for example, under stirring. The temperature during the stirring is not particularly limited, as long as the mixture can form particles in the dispersion medium, and is preferably 10 to 60°C, for example. The stirring time is not particularly limited, as long as the mixture can form particles in the dispersion medium, and is preferably 1 to 15 minutes, and more preferably 3 to 5 minutes, for example.

[0098] The dispersion medium may contain other components, such as a surfactant and a dispersant such as concentrated glycerin. When the dispersion medium contains such other components, the method for producing the second composition may involve, for example, mixing the dispersion medium with the surfactant and / or dispersant before, during, or after the addition of the mixture, and homogenizing or dispersing the mixture in the dispersion medium. The temperature during the mixing is not particularly limited as long as the surfactant and / or dispersant can be dispersed in the dispersion medium, and a preferred temperature is, for example, 20 to 30°C. The time during the mixing is not particularly limited as long as the surfactant and / or dispersant can be dispersed in the dispersion medium, and a preferred temperature is, for example, 10 minutes to 2 hours.

[0099] After forming particles from the mixture, the method for producing the second composition may, for example, include sieving. This allows the method for producing the second composition to adjust the particle size of the oil gel particles and improve the feel upon use. The sieving can be performed, for example, using a sieve.

[0100] After the sieving, the method for producing the second composition may, for example, wash the oil gel particles. The washing can be performed by, for example, a known method, specifically, washing with an aqueous solvent. Examples of the aqueous solvent include purified water, distilled water, ion-exchanged water, pure water, and ultrapure water.

[0101] After the washing, the method for producing the second composition may involve, for example, drying the oil gel particles. The drying can be performed by a known method, for example, such as drying by leaving the particles to stand at room temperature, freeze drying, or spray drying.

[0102] <Third Composition> In another aspect, the present disclosure provides a composition (hereinafter also referred to as the "third composition") with improved permeability of bakuchiol through the stratum corneum. As described above, the third composition of the present disclosure comprises liposomes, which contain bakuchiol, complex lipids, and sterols. The third composition of the present disclosure is characterized by comprising liposomes, which contain bakuchiol, complex lipids, and sterols, with other configurations and conditions not being particularly limited. The third composition of the present disclosure can provide, for example, a composition with improved permeability of bakuchiol through the stratum corneum. The same explanations as for the first composition of the present disclosure and the second composition of the present disclosure can be applied to the third composition of the present disclosure.

[0103] As a result of intensive research, the present inventors have found that by forming liposomes with bakuchiol and complex lipids and sterols, the permeability through the stratum corneum is higher than that of bakuchiol alone, and have established the present disclosure.It is presumed that the improvement in permeability through the stratum corneum is due to the improved dispersibility of bakuchiol in the stratum corneum caused by the liposome formation.However, this presumption does not limit the present disclosure.Therefore, according to the present disclosure, a composition with improved permeability through the stratum corneum for bakuchiol can be provided.

[0104] The content of bakuchiol is preferably, for example, greater than 0% by mass to 40% by mass, 2 to 40% by mass, 4 to 40% by mass, 4 to 25% by mass, 5 to 40% by mass, 5 to 25% by mass, or 5 to 10% by mass, based on the total mass of the liposome.

[0105] The complex lipid is a lipid containing phosphate, sugar, sulfur, or a nitrogen-containing base in the molecule. The complex lipid is not particularly limited, and examples thereof include phospholipids, glycolipids, lipoproteins, sulfolipids, etc., with phospholipids being preferred. The phospholipid is not particularly limited as long as it has a phosphate ester moiety in its molecular structure and is capable of forming a bilayer membrane. Examples of the phospholipid include phosphatidylcholine, phosphatidylethanolamine, sphingomyelin, phosphatidylserine, phosphatidylinositol, phosphatidylglycerol, and phosphatidic acid, with phosphatidylcholine being preferred.

[0106] The content of the complex lipid is preferably, for example, 25 to 75% by mass, 30 to 60% by mass, or 40 to 45% by mass based on the total mass of the liposome.

[0107] Examples of the sterols include plant sterols (phytosterols), animal sterols (zoosterols), etc. Examples of the animal sterols include cholesterol and cholesterol derivatives such as dihydrocholesterol, dehydrocholesterol, cholesteryl oleate, cholesteryl isostearate, cholesteryl hydroxystearate, and polyoxyethylene cholesteryl ether, and cholesterol is preferred.

[0108] The content of the sterols is preferably, for example, 2 to 20% by mass, 5 to 15% by mass, or 8 to 10% by mass based on the total mass of the liposome.

[0109] The liposome may further contain, for example, an anionic substance. The anionic substance refers to a substance that becomes negatively charged when dissolved in water. Examples of the anionic substance include diacylglycerol hemisuccinate, diacylglycerol hemimalonate, diacylglycerol hemiglutarate, diacylglycerol hemiadipate, diacylglycerol hemicyclohexane-1,4-dicarboxylic acid, and fatty acids. Examples of the fatty acids include oleic acid, myristic acid, palmitic acid, stearic acid, nervonic acid, and behenic acid. The anionic substance is preferably, for example, a saturated fatty acid that is solid at room temperature (10°C to 30°C), and preferably palmitic acid, stearic acid, or the like.

[0110] When the third composition of the present disclosure contains the anionic substance, the content of the anionic substance is, for example, preferably from more than 0% to 20% by mass, from 1 to 18% by mass, or from 2 to 16% by mass, and more preferably from 2.5 to 15% by mass, based on the total mass of the liposomes. By setting the content of the anionic substance in the third composition of the present disclosure to 20% by mass or less, for example, the emulsified state of the liposomes in the aqueous solvent can be suitably maintained, and the occurrence of turbidity, aggregation, or precipitation can be suppressed.

[0111] The liposome may further contain, for example, a zwitterionic surfactant. Examples of the zwitterionic surfactant include N-alkyl-N,N-dimethylamino acid betaines including lauryldimethylaminoacetic acid betaine (lauryl betaine), fatty acid amidoalkyl-N,N-dimethylamino acid betaines including cocamidopropyl betaine and lauramidopropyl betaine, imidazoline-type betaines including sodium cocoamphoacetate and sodium lauroamphoacetate, alkyl sulfobetaines including alkyldimethyltaurines, sulfate-type betaines including alkyldimethylaminoethanol sulfate esters, and phosphate-type betaines including alkyldimethylaminoethanol phosphate esters.

[0112] When the third composition of the present disclosure contains the zwitterionic surfactant, the content of the zwitterionic surfactant is, for example, preferably 0 to 20% by mass, more preferably 5 to 20% by mass, or more preferably 7 to 15% by mass, based on the total mass of the liposomes. By setting the content of the zwitterionic surfactant to 20% by mass or less, the third composition of the present disclosure can preferably maintain the emulsified state of the liposomes in the aqueous solvent and suppress the occurrence of cloudiness, aggregation, or precipitation.

[0113] The liposomes are preferably pH-responsive liposomes. In the present disclosure, "pH-responsive" refers to, for example, the transition of the zeta potential of the liposomes from positive to negative under any pH condition within a predetermined range. Specifically, when dispersed in an aqueous medium at pH 5 or below, the zeta potential of the liposomes is positive; when dispersed in an aqueous medium at pH 8 or above, the zeta potential of the liposomes is negative; and when dispersed in an aqueous medium between pH 5 and 8, the zeta potential of the liposomes transitions from positive to negative as the pH increases. Therefore, it is believed that the liposomes contained in the third composition of the present disclosure retain bakuchiol and remain stable in an aqueous medium at pH 5 or below, but become unstable in an aqueous medium at pH 5 to 8 under pH conditions where the zeta potential is zero, undergoing membrane fusion and releasing bakuchiol. Known methods can be used to measure the zeta potential. Specific examples of methods for measuring the zeta potential include electrophoretic light scattering (laser Doppler) and the like.

[0114] The shape of the liposome is not particularly limited, and may be a multilayer liposome or a unilamellar liposome.

[0115] The average particle size of the liposomes is preferably 50 to 1100 nm, 50 to 200 nm, or 50 to 100 nm. The average particle size of the liposomes can be measured by, for example, a known method, specifically, dynamic light scattering. The average particle size of the liposomes can be adjusted appropriately depending on the intended use. For example, when the liposomes are intended for administration to the body, the particle size of the liposomes is preferably adjusted to an average particle size of 200 nm or less. The average particle size of the liposomes can be adjusted, for example, by passing the liposomes through a filter with a small pore size using an extruder or the like. When the liposomes have an average particle size of about 100 nm or less and are unilamellar liposomes, the liposomes are, for example, uniform in size and thermodynamically stable, and exhibit good skin permeability when used as cosmetics.

[0116] The permeability of the third composition of the present disclosure through the stratum corneum can be evaluated by, for example, measuring the permeability of the third composition of the present disclosure through an artificial synthetic membrane such as a membrane for skin permeability testing. Specifically, see Example 3 below. When an absorption test is carried out using a Franz cell and a Strat-M (trademark) membrane, if the increase in the amount of bakuchiol absorbed is 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more, 95% or more, or 99% or more compared to the case of bakuchiol-containing water and / or the case of only the film-forming component, it can be determined that the third composition of the present disclosure has improved permeability through the stratum corneum.

[0117] The third composition of the present disclosure can be produced, for example, in accordance with a method for producing liposomes, and reference can be made to the method for producing liposomes in International Publication No. 2019 / 045097. The method for producing the third composition may refer to the method described in Example 3 below. As an example, the third composition can be produced by mixing a dispersion medium (first preparation solution) such as an aqueous solvent containing bakuchiol with a dispersion medium (second preparation solution) containing components constituting the lipid membrane of the liposome.

[0118] The first preparation liquid can be prepared, for example, by dispersing the bakuchiol in a dispersion medium such as the aqueous solvent. The dispersion can be carried out by mixing the bakuchiol with the dispersion medium. The first preparation liquid may further contain, for example, a preservative, a solubilizer, or the like. Examples of preservatives include phenoxyethanol. Examples of solubilizers include nonionic surfactants such as polysorbate 60. The temperature during the dispersion is not particularly limited as long as the bakuchiol can be dispersed in the dispersion medium, and is preferably, for example, 70 to 90°C, and more preferably 75 to 85°C. The time during the dispersion is not particularly limited as long as the bakuchiol can be dispersed in the dispersion medium, and is preferably 3 minutes to 1 hour, more preferably 5 to 30 minutes, and even more preferably 10 minutes.

[0119] Next, the second preparation solution is preferably prepared by mixing components constituting the lipid membrane of the liposome, such as the complex lipids and the sterols, with a dispersion medium such as an organic solvent and homogenizing or dispersing the components in the dispersion medium. Examples of the organic solvent include polyhydric alcohols such as butylene glycol, glycerin, and concentrated glycerin. The mixing is preferably performed by stirring without foaming. The mixing temperature is not particularly limited, as long as the components constituting the lipid membrane are dispersible in the dispersion medium. For example, 70 to 90°C is preferred, and 75 to 85°C is more preferred. The mixing time is not particularly limited, as long as the components constituting the lipid membrane are dispersible in the dispersion medium. For example, 15 minutes to 1 hour, with 30 minutes being preferred.

[0120] The second preparation liquid may further contain, for example, the anionic substance, the zwitterionic surfactant, or the like.

[0121] After mixing the complex lipids and the sterols, the second preparation may be prepared by adding the mixture of the complex lipids and the sterols to a dispersant (dispersion medium) such as concentrated glycerin, and then mixing and homogenizing the mixture. The third composition production method involves dispersing the complex lipids and the sterols in the dispersion medium multiple times, thereby efficiently forming the liposomes when mixed with the first preparation. The dispersant is preferably used at 80 to 85°C.

[0122] The method for producing the third composition includes, for example, mixing the first preparation liquid and the second preparation liquid. The mixing temperature is not particularly limited as long as the first preparation liquid and the second preparation liquid can be mixed, and is, for example, preferably 75 to 90° C. The mixing time is not particularly limited as long as the first preparation liquid and the second preparation liquid can be mixed, and is, for example, 15 minutes to 1 hour, and preferably 30 minutes.

[0123] <Fourth Composition> In another aspect, the present disclosure provides a powder composition containing bakuchiol (hereinafter also referred to as the "fourth composition"). As described above, the fourth composition of the present disclosure contains bakuchiol and silica, and the bakuchiol is supported on the silica. The fourth composition of the present disclosure is characterized by containing bakuchiol and silica, and the bakuchiol is supported on the silica, and other configurations and conditions are not particularly limited. According to the fourth composition of the present disclosure, for example, bakuchiol can be provided in powder form. The descriptions of the first, second, and third compositions of the present disclosure can be used for the fourth composition of the present disclosure.

[0124] As a result of intensive research, the present inventors have found that silica can support bakuchiol, thereby enabling liquid bakuchiol to be powdered, and have established the present disclosure. Therefore, according to the present disclosure, a composition containing bakuchiol that is easy to handle can be provided.

[0125] The content of bakuchiol is preferably, for example, 0.01 to 30% by mass, 0.1 to 20% by mass, or 1 to 10% by mass, based on the total mass of the fourth composition of the present disclosure.

[0126] The silica is not particularly limited, and can be, for example, one used in ordinary skin external preparations, cosmetics, etc., specific examples include silicic anhydride, silicon dioxide, etc. The particle shape of the silica is not particularly limited, and can be any shape, but spherical is preferred because it is suitable for use in cosmetics. The silica can be, for example, porous silica, hollow silica, non-porous silica, etc., and porous silica is preferred because it has an excellent bactiol loading capacity. The silica can be used alone or in combination of multiple types. The silica can be a synthetic product or a commercially available product. The silica can be used without surface treatment, or can be used after various treatments.

[0127] The content of the silica is preferably 60 to 95 mass%, 70 to 90 mass%, or 75 to 85 mass%, based on the total mass of the fourth composition of the present disclosure, for example, because such a content provides excellent handleability.

[0128] The average particle size of the fourth composition of the present disclosure is preferably 0.01 to 500 μm, 0.1 to 100 μm, 1 to 10 μm, or 4 to 6 μm, since the composition is suitable for use in cosmetics. The average particle size can be measured by observing the bakuchiol-loaded silica using a transmission electron microscope (TEM). The average particle size can also be referred to as the average particle size of the bakuchiol-loaded silica.

[0129] Examples of the higher alcohol include behenyl alcohol, cetyl alcohol, stearyl alcohol, myristyl alcohol, cetostearyl alcohol, isostearyl alcohol, monostearyl glycerin ether (batyl alcohol), lauryl alcohol, hexadecyl alcohol, octyldodecanol, oleyl alcohol, 2-decyltetradecynol, lanolin alcohol, etc. The higher alcohol is preferably behenyl alcohol because it can impart a feel upon use such as a smooth feel.

[0130] When the fourth composition of the present disclosure contains the higher alcohol, the content of the higher alcohol is preferably, for example, more than 0 mass % to 30 mass % based on the total mass of the fourth composition of the present disclosure.

[0131] For example, the bakuchiol is supported on at least one of the surface and the interior of the silica, and preferably at least on the interior of the porous silica.

[0132] The fourth composition of the present disclosure can be produced, for example, by contacting the bakuchiol with the silica, specifically by mixing the bakuchiol with the silica. For example, the method described in Example 4 can be used for producing the fourth composition.

[0133] The mixing can be performed, for example, by manual shaking, stirring with a stirring bar or stirring blade, or using an ultrasonic vibrator. The mixing temperature is preferably, for example, 40 to 70° C. The mixing time is preferably 0.5 to 1.5 hours.

[0134] Prior to the mixing, the bakuchiol is preferably dispersed in a solvent such as ethanol, which allows the bakuchiol to be uniformly impregnated into the silica during the mixing process, thereby increasing the amount of bakuchiol supported on the silica.

[0135] After the mixing, the method for producing the fourth composition preferably includes, for example, mixing the resulting mixture with a higher alcohol. By mixing the higher alcohol, the method for producing the fourth composition can impart a texture such as a smooth feel to the resulting fourth composition. After mixing with the higher alcohol, the method for producing the fourth composition may include, for example, heating and stirring. The temperature during the heating and stirring is preferably, for example, 100 to 110°C, and more preferably 105°C. The time during the heating and stirring is preferably, for example, 0.5 to 1.5 hours, and more preferably 1 hour.

[0136] After the heating and stirring, the fourth method for producing a composition preferably includes cooling the mixture after the heating and stirring, for example, to 40 to 60°C.

[0137] After the cooling, the fourth method for producing a composition may include sieving, for example, to remove foreign matter or adjust the particle size of the bakuchiol-loaded silica. The sieving can be performed using, for example, a sieve.

[0138] <Use> The conditions for use (administration conditions) of the first to fourth compositions of the present disclosure are not particularly limited, and the administration form, administration time, dosage, etc. can be appropriately set depending on, for example, the type of subject to be administered.

[0139] The administration form of the first to fourth compositions of the present disclosure is preferably parenteral administration. Examples of parenteral administration include transdermal administration and application (contact) to the skin. Application to the skin may include application to the oral mucosa, i.e., application to or contact with epithelial cells in the oral cavity. Furthermore, application to the skin may also include administration or injection into the skin or subcutaneously via the skin surface, in addition to or instead of application to the skin surface. Administration or injection into the skin via the skin surface can be performed, for example, using a microneedle.

[0140] When the first to fourth compositions of the present disclosure are used for transdermal administration or application to the skin (hereinafter also referred to as "external skin preparations"), the form of the external skin preparation may be, depending on the form of use, an ampoule, capsule, powder, granules, liquid, gel, foam, emulsion, sheet, mist, spray, etc. Examples of the form of use include pharmaceutical(s), quasi-drug(s), topical or systemic external skin preparations, medicinal and / or cosmetic preparations to be applied to the scalp and hair, bath additives to be added to bathwater, other preparations, etc. Examples of the topical or systemic skin preparations include basic cosmetics such as lotions, milky lotions, creams, ointments, lotions, oils, and packs; face washes or skin cleansers such as solid soaps, liquid soaps, and hand washes; massage agents, cleansing agents, hair removers, depilatories, shaving treatments, aftershave lotions, pre-shave lotions, shaving creams; makeup cosmetics such as foundations, lipsticks, blushers, eye shadows, eyeliners, and mascaras; perfumes; nail polish, nail enamel, nail enamel removers; poultices, plasters, tapes, sheets, patches, aerosols, toothpaste, and mouthwashes. Examples of the medicinal and / or cosmetic preparations to be applied to the scalp and hair include shampoos, rinses, hair treatments, pre-hair treatments, permanent solutions, hair dyes, hair styling products, hair tonics, hair growth and care products, poultices, plasters, tapes, sheets, aerosols, etc. Examples of the other preparations include underarm odor inhibitors or deodorants, antiperspirants, sanitary products, sanitary cotton products, wet tissues, etc.

[0141] Next, examples of the present invention will be described. However, the present invention is not limited to the following examples. Commercially available reagents were used according to their protocols unless otherwise specified.

[0142] Example 1 A first composition of the present disclosure was prepared, and its dispersibility in a solvent was confirmed.

[0143] Example 1A: The first composition was prepared by combining the various components listed in Table 1 below. 0.02 parts (parts by mass, hereinafter the same) of bakuchiol (manufactured by Ichimaru Pharcos Co., Ltd.) and 0.98 parts of caprylic / capric triglyceride (solvent, manufactured by Kokyu Alcohol Kogyo Co., Ltd. or Nisshin Oillio Group Co., Ltd.) were mixed together. After mixing, 0.4 parts of phenoxyethanol (preservative, manufactured by Yokkaichi Synthetic Co., Ltd. or Toho Chemical Industry Co., Ltd.) and 2.0 parts of PPG-6 decyltetradeceth-30 (nonionic surfactant, manufactured by Nippon Chemicals Sales Co., Ltd.) were added to the resulting mixture, which was then homogenized at 60-70°C to obtain Mixture I. Next, 0.1 parts of oligopeptide-56 amide PEG-75 methyl ether (block copolymer, manufactured by Ichimaru Pharcos Co., Ltd.) and 48.25 parts of purified water were mixed together. After the mixing, nanoparticle treatment (50 MPa, 1 pass) was performed to obtain mixture II. Then, mixture II heated to 60-70°C was added to 48.25 parts of purified water heated to 60-70°C, and homogenization was performed to obtain mixture III. Mixture I was added to mixture III, and stirring was performed. After stirring, the mixture was cooled. After cooling, purified water was added so that the total amount became 100 parts, and homogenization was performed to obtain the composition of Example 1A.

[0144]

[0145] Example 1B The composition of Example 1B was obtained in the same manner as in Example 1A, except that 0.08 parts of bakuchiol and 0.92 parts of caprylic / capric triglyceride were used.

[0146] Example 1C The composition of Example 1C was obtained in the same manner as in Example 1A, except that 0.16 parts of bakuchiol and 0.84 parts of caprylic / capric triglyceride were used.

[0147] Example 1D The composition of Example 1D was obtained in the same manner as in Example 1A, except that 0.2 parts of bakuchiol and 0.8 parts of caprylic / capric triglyceride were used.

[0148] Example 1E: The various components listed in Table 2 below were combined to prepare a first composition of the present disclosure by the following method. 0.3 parts bakuchiol (manufactured by Ichimaru Pharcos Co., Ltd.) and 1.0 parts caprylic / capric triglyceride (solvent, manufactured by Kokyu Alcohol Kogyo Co., Ltd. or Nisshin Oillio Group, Ltd.) were mixed. After mixing, 0.4 parts phenoxyethanol (preservative, manufactured by Yokkaichi Synthetic Co., Ltd. or Toho Chemical Industry Co., Ltd.), 2.0 parts PPG-6 decyltetradeceth-30 (nonionic surfactant, manufactured by Nippon Chemicals Co., Ltd.), 2.0 parts BG (solvent, butylene glycol, manufactured by Daicel Corporation, Nippon Refine Co., Ltd., or Kokyu Alcohol Kogyo Co., Ltd.), and 0.1 parts oligopeptide-56 amide PEG-75 methyl ether (block copolymer, manufactured by Ichimaru Pharcos Co., Ltd.) were added, and the mixture was homogenized at 60 to 70°C to obtain Mixture I. Thereafter, Mixture I heated to 60 to 70°C was added to 94.2 parts of purified water heated to 60 to 70°C, and homogenization was performed to obtain Mixture II. Mixture II was subjected to nanoparticle formation treatment (50 MPa, 1 pass), and purified water was added to make the total volume 100 parts, followed by homogenization to obtain the composition of Example 1E.

[0149]

[0150] Example 1F The composition of Example 1F was obtained in the same manner as in Example 1E, except that 0.5 parts of bakuchiol and 94.0 parts of purified water were used.

[0151] Example 1G The composition of Example 1G was obtained in the same manner as in Example 1E, except that 0.5 parts of bakuchiol, 3 parts of BG, and 93.0 parts of purified water were used.

[0152] [Example 1H] The composition of Example 1H was obtained in the same manner as in Example 1E, except that 0.5 parts of bakuchiol, 3 parts of BG, and 2.5 parts of PPG-6 decyltetradeceth-30 were used, and the nanoparticle formation process was performed in 3 passes.

[0153] The compositions of Examples 1A to 1H are shown in Table 3 below.

[0154]

[0155] Test Example 1: Dispersibility The dispersibility of each of the compositions of Examples 1A to 1H in a solvent was examined. Specifically, the compositions of Examples 1A to 1H were left to stand in the dark for one month at 25°C. The results are shown in Figure 1.

[0156] Figure 1 is a photograph showing the dispersibility of each of the first compositions of the present disclosure in a solvent. As shown in Figure 1, no precipitation was observed in the compositions of Examples 1A to 1H. These results demonstrate that the particles of the first composition of the present disclosure are uniformly distributed in the solvent without agglomeration, i.e., the composition has dispersibility in the solvent.

[0157] [Test Example 2] Average Particle Size Next, the average particle size of oil droplets formed in the first composition of the present disclosure was measured for the first composition of the present disclosure. Specifically, the composition of Example 1B, 1E, or 1H was allowed to stand for one month at 25°C under light-shielded conditions. After standing, the composition was diluted 100 times with ultrapure water. After dilution, the average particle size distribution was measured using a Zetasizer Nano (manufactured by Malvern Panalytical). Note that calibration using standard particles was performed in the measurement. The measurement was performed using dynamic light scattering as the measurement principle. These results are shown in Figure 2.

[0158] Figure 2 is a graph showing the distribution of the average particle size of oil droplets contained in each first composition of the present disclosure. In Figure 2, the vertical axis represents scattering intensity (%), and the horizontal axis represents average particle size (nm). As shown in Figure 2, at a bakuchiol concentration of 0.08% (composition of Example 1B), the average particle size was 26.8 nm. At a bakuchiol concentration of 0.3% (composition of Example 1E), the average particle size was 25.9 nm. At a bakuchiol concentration of 0.5% (composition of Example 1H), the average particle size was 49.5 nm.

[0159] [Example 2]

[0160] The thermal stability of the carotenoid in the second composition of the present disclosure was confirmed.

[0161] (1) Preparation of Second Composition The second composition of the present disclosure was prepared by combining the various components listed in Table 4 below using the following method. 49.32 g of NIKKOL sugar squalane (oil agent, manufactured by Nikko Chemicals Co., Ltd.), 21.6 g of palmitic acid dextrin (gelling agent, Leopearl KL2, manufactured by Chiba Flour Milling Co., Ltd.), 0.72 g of vitamin A palmitate (carotenoid derivative, unstable, manufactured by BASF Japan Ltd.), and 0.36 g of bakuchiol (manufactured by Ichimaru Pharcos Co., Ltd.) were stirred at room temperature (approximately 24°C; the same applies below). After stirring, it was confirmed that each component was uniformly dispersed in the oil agent. After confirmation, the mixture was heated to 110°C and maintained for 30 minutes for heat treatment to obtain Mixture I. Next, 200 g of concentrated cosmetic glycerin (dispersant, manufactured by Iwaki Co., Ltd.), 120 g of purified water (dispersion medium), and 10.24 g of EMALEX ET-8020 (surfactant, manufactured by Nippon Emulsion Co., Ltd.) were stirred to obtain Mixture II. Then, while stirring Mixture II, Mixture I was added and stirred for 4 minutes. After stirring, particle formation was confirmed. After confirmation, the particles were sieved using a sieve with 1.5 mm openings. After sieving, the sieved particles were washed with water and dried for 2 days. After drying, the composition of Example 2 was obtained. A portion of the composition of Example 2 was further stored at 25°C under light-shielded conditions for approximately 10 days.

[0162]

[0163] The component contents and composition of the composition of Example 2 are shown in Table 5 below.

[0164]

[0165] (2) Evaluation of Thermal Stability of Retinol Palmitate Next, the thermal stability of vitamin A palmitate contained in the composition of Example 2 was examined. Specifically, the thermal stability was evaluated based on Vitamin A Quantitation Method 1-1 described in Quasi-drug Ingredients Standard 2021 (Pharmaceutical Evaluation and Licensing Division, Pharmaceutical and Food Safety Bureau, Ministry of Health, Labour and Welfare). First, 2-propanol was added to the second composition of the present disclosure and stirred. After stirring, the mixture was subjected to ultrasonic disruption and centrifugation. After centrifugation, the supernatant was separated. After separation, 2-propanol was added to the obtained supernatant, and the above procedure was repeated twice. After separating the final supernatant, 2-propanol was added to the obtained supernatant to adjust the appropriate concentration, and the supernatant was subjected to Vitamin A Quantitation Method 1-1. The appropriate concentration was adjusted so that the absorbance at the measurement wavelength was between 0.1 and 1. The absorption spectrum of the sample after concentration adjustment was measured in the wavelength range of 220 to 400 nm, and the wavelength of the absorption maximum was determined. Next, the absorbance of the sample was measured at wavelengths of 300 nm, 310 nm, 320 nm, 330 nm, 340 nm, and 350 nm. ３２６ ) versus absorbance at each wavelength (Aλ ｉ ) ratio (Aλ ｉ / A ３２６ ) were within ±0.030 of the values ​​shown in Table 6 below, the vitamin A concentration in the sample was calculated using the following formula (2). Note that if the absorption maximum wavelength was outside the range of 325 to 328 nm, or if the absorbance ratio (Aλ ｉ / A ３２６ If the absorbance ratio (Aλ) of the second composition of the present disclosure is outside the range of ±0.030 of the value shown in Table 6 below, Vitamin A Determination Method 1-1 described in the Quasi-drug Raw Materials Standards is not suitable. ｉ / A ３２６) was outside the range of ±0.030 of the value shown in Table 6 below. However, since the bakuchiol contained in the second composition of the present disclosure has almost zero absorbance at a wavelength of 326 nm, it was determined that it would not affect the calculated value of formula (2) below, and the second composition of the present disclosure was analyzed using Vitamin A Quantitation Method 1-1 described in the Quasi-Drug Raw Materials Standards. A blank composition prepared in the same manner as in Example 2(1) above, except that it did not contain vitamin A palmitate (retinol palmitate), was used. Because the blank composition had absorbance at a wavelength of 326 nm, it was used as a blank at a wavelength of 326 nm. A comparative example was prepared in the same manner as the composition of Example 2 above, except that bakuchiol was not added. The content of vitamin A obtained relative to the amount of vitamin A used during production was calculated as the recovery rate. The recovery rate was calculated based on the concentration actually measured immediately after dissolving vitamin A palmitate in 2-propanol. These results are shown in Table 7 below. Number of vitamin A units in 1g = A ３２６ ×V×1900 / (W×100)...(2) A ３２６ : absorbance at a wavelength of 326 nm V: volume (ml) of the prepared sample solution W: amount of sample (g) in V ml of sample solution 1900: conversion factor of the specific absorbance of esterified retinol to international units (units / g)

[0166]

[0167]

[0168] Table 7 shows the recovery rate of vitamin A based on the vitamin A concentration calculated using Vitamin A Quantitation Method 1-1 described in the Quasi-Drug Raw Materials Standards. As shown in Table 7, the recovery rate of retinol palmitate in the comparative example (-bakuchiol) was 2.8% immediately after production and 3.4% approximately 10 days after production. On the other hand, the recovery rate of retinol palmitate in the composition of Example 2 (+bakuchiol) was 57.6% immediately after production and 52.4% approximately 10 days after production. These results demonstrate that the retinol palmitate in the second composition of the present disclosure has improved thermal stability.

[0169] Example 3 A third composition of the present disclosure was prepared, and its permeability into the stratum corneum was confirmed.

[0170] (1) Preparation of Third Composition The third composition of the present disclosure was prepared by the following method, combining the various components and compositions listed in Table 8 below. 96.8 g of purified water (dispersion medium), 2 g of phenoxyethanol (preservative, HYSOLV EPH, manufactured by Toho Chemical Industry Co., Ltd.), 1 g of polysorbate 60 (solubilizer, EMALEX TS-10V, manufactured by Nippon Emulsion Co., Ltd.), and 0.19 g of bakuchiol (manufactured by Ichimaru Pharcos Co., Ltd.) were mixed and heated to 75-85°C to obtain Solution I. Next, 2.05 g of hydrogenated phosphatidylcholine (complex lipid, Phospholipon 90H, H-Holstein Co., Ltd.), 0.45 g of cholesterol (sterol, Kairei Marine Cholesterol, Nippon Suisan Co., Ltd.), 0.25 g of palmitic acid (anionic substance, NAA-160, NOF Corporation), and 0.5 g of lauryl betaine (zwitterionic surfactant, NIKKOL AM-301, Nikko Chemicals Co., Ltd.) were added in this order to 48.375 g of 1,3-butylene glycol (solvent, butylene glycol, manufactured by Daicel Corporation, Nippon Refine Co., Ltd., or Kokyu Alcohol Kogyo Co., Ltd.) heated to 75 to 85°C, and the mixture was stirred and dissolved without foaming to obtain Solution II. Thereafter, the solution II was added to 48.375 g of concentrated glycerin (dispersant, concentrated glycerin for cosmetics, manufactured by Iwaki Co., Ltd.) that had been heated to 80 to 85°C and stirred, and the mixture was homogenized to obtain solution III. After the homogenization, solution I and solution III were mixed under heating and allowed to cool, thereby obtaining the composition of Example 3.

[0171]

[0172] (2) Stratum Corneum Permeability Evaluation Next, the stratum corneum permeability of the composition of Example 3 was examined. Specifically, a Strat-M™ membrane was attached to a static diffusion cell (Franz cell). The Strat-M™ has a structure similar to that of human skin and is therefore commonly used to evaluate stratum corneum permeability. Physiological saline (0.9% sodium chloride solution) was used as the receptor liquid on the reservoir side. Furthermore, 1.0 ml of the third composition of the present disclosure was used on the donor side. The entire Franz cell was maintained at 32°C, and the membranes were recovered after 3 or 24 hours. After recovery, the membranes were washed with purified water and dried. After drying, the membranes were subjected to fluorescence observation under UV 254 nm light. After drying, 20 ml of ethanol was added to each membrane. After the addition, the ethanol was recovered, and the components were extracted from the filter again with 20 ml of ethanol, and the ethanol was recovered. Then, ethanol was distilled off from the total 40 ml of ethanol collected, and bakuchiol was quantified. The quantification was performed by HPLC analysis under the following measurement conditions. From the obtained quantitative value, the recovery rate of bakuchiol was calculated based on the bakuchiol introduced into the static diffusion cell. Control 1 was performed in the same manner, except that water containing 0.1% bakuchiol was used instead of the third composition of the present disclosure. Control 2 (film-forming component only) was performed in the same manner, except that a bakuchiol-free composition prepared by the method of Example 3 (1) using water instead of bakuchiol was used instead of the third composition of the present disclosure. These results are shown in Figure 3.

[0173] (HPLC measurement conditions) HPLC system: SHIMADZU LC-20ADxr (Shimadzu Corporation) Column: Mightysil RP-18GP 250 x 4.6 mm (particle diameter 5 μm) (Kanto Chemical Co., Ltd.) Flow rate: 1.0 mL / min Detector wavelength: 260 nm Gradient program: CH ３ CN: 0.1% H ３ P.O. ４ =80:20

[0174] Figure 3 is a photograph showing the stratum corneum permeability of the third composition of the present disclosure. Figure 3(A) shows the results after 3 hours, and Figure 3(B) shows the results after 24 hours. In Figure 3, the upper row is a photograph of the front side of the Franz cell, and the lower row is a photograph of the back side of the Franz cell. In Figure 3, from the left, the results are shown for the third composition of the present disclosure, Control 1, and Control 2 (film-forming component only). As shown in Figure 3, it was found that the third composition of the present disclosure penetrated to the back side of Strat-M™ after 24 hours, compared to Control 1 and Control 2.

[0175] Furthermore, the recovery rate of bakuchiol after 3 hours was 2.3% for the third composition of the present disclosure, 0.5% for Control 1, and 0% for Control 2. The recovery rate of bakuchiol after 24 hours was 8.9% for the third composition of the present disclosure, 2.4% for Control 1, and 0% for Control 2. These results demonstrate that the third composition of the present disclosure has high stratum corneum permeability.

[0176] Example 4 A fourth composition of the present disclosure was prepared and confirmed to have excellent handling properties.

[0177] The various components and compositions listed in Table 9 below were combined by the following method to prepare a fourth composition of the present disclosure. Specifically, 2.0 g of bakuchiol (manufactured by Ichimaru Pharcos Co., Ltd.) and 18 g of ethanol (solvent) were mixed. After the mixing, 16.0 g of silica (carrier, Sunsphere H-53, manufactured by AGC Si-Tech Co., Ltd.) was added and stirred and mixed. After the mixing, 2.0 g of behenyl alcohol (higher alcohol, Kalcol 220-80, manufactured by Kao Corporation) was added and mixed. After the mixing, the mixture was heated and stirred at 105°C for 1 hour. The mixture was then cooled to 40-60°C. After the cooling, foreign matter was removed using a 100-mesh sieve to obtain the composition of Example 4. The resulting composition of Example 4 was a porous, smooth powder.

[0178]

[0179] Although the present disclosure has been described above with reference to embodiments and examples, the present disclosure is not limited to the above embodiments and examples. Various modifications that can be understood by a person skilled in the art can be made to the configuration and details of the present disclosure within the scope of the present disclosure.

[0180] This application claims priority based on Japanese Patent Application No. 2023-138085, filed on August 28, 2023, the disclosure of which is incorporated herein in its entirety by reference.

[0181] <Appendix> Some or all of the above embodiments and examples can be described as, but are not limited to, the following appendices. <Water-Soluble Bakuchiol> (Appendix 1) A composition comprising bakuchiol, a solvent, and a nonionic surfactant and / or anionic surfactant. (Appendix 2) The composition according to Appendix 1, wherein the solvent is an ester oil, a hydrocarbon oil, and / or an ether oil. (Appendix 3) The composition according to Appendix 1 or 2, wherein the solvent is an ester oil. (Appendix 4) The composition according to any one of Appendixes 1 to 3, wherein the solvent is caprylic / capric triglyceride. (Appendix 5) The composition according to any one of Appendixes 1 to 4, wherein the nonionic surfactant is an ethylene oxide condensation type, a polyhydric alcohol ester type, and / or a polyhydric alcohol condensation type. (Appendix 6) The composition according to any one of Appendixes 1 to 5, wherein the nonionic surfactant is an ethylene oxide condensation type. (Appendix 7) The composition according to any one of Appendices 1 to 6, wherein the nonionic surfactant is a polyoxyethylene polyoxypropylene alkyl ether. (Appendix 8) The composition according to Appendices 7, wherein the polyoxyethylene polyoxypropylene alkyl ether is polyoxyethylene polyoxypropylene decyltetradecyl ether, polyoxyethylene polyoxypropylene cetyl ether, polyoxyethylene polyoxypropylene monobutyl ether, polyoxyethylene polyoxypropylene, hydrogenated lanolin, and / or polyoxyethylene polyoxypropylene glycerin ether. (Appendix 9) The composition according to any one of Appendices 1 to 8, wherein the anionic surfactant is a carboxylic acid-based surfactant, a higher alcohol-based surfactant, a sulfonic acid-based surfactant, a peptide-based surfactant, an olefin-based surfactant, an amino acid-based surfactant, a taurine-based surfactant, and / or a lactic acid-based surfactant. (Appendix 10) The composition according to any one of Appendices 1 to 9, wherein the content of bakuchiol is 0.001 to 5% by mass, based on the total mass of the composition. (Appendix 11) The composition according to any one of Appendices 1 to 10, wherein the content of the solvent is greater than 0% by mass and 5% by mass, based on the total mass of the composition.(Appendix 12) The composition according to any one of Appendices 1 to 11, wherein the content of the anionic surfactant and / or nonionic surfactant is 2 to 20% by mass, based on the total mass of the composition. (Appendix 13) The composition according to any one of Appendices 1 to 12, further comprising a block copolymer. (Appendix 14) The composition according to any one of Appendices 1 to 13, wherein the block copolymer is a polyamino acid-polyethylene glycol block copolymer, a polylactic acid-polyethylene glycol block copolymer, a polylactic acid-polyglycolic acid block copolymer, a polysarcosine-polyethylene glycol block copolymer, and / or a polyoxazoline-polysiloxane block copolymer. (Appendix 15) The composition according to any one of Appendices 1 to 14, wherein the block copolymer is oligopeptide-56 amide PEG-75 methyl ether. (Appendix 16) The composition according to any one of Appendices 13 to 15, wherein the content of the block copolymer is 0.02 to 2% by mass, based on the total mass of the composition. (Appendix 17) The composition according to any one of Appendices 1 to 16, further comprising a dispersion medium. (Appendix 18) The composition according to Appendices 17, wherein the content of the dispersion medium is from more than 0% to 5% by mass, based on the total mass of the composition. (Appendix 19) The composition according to any one of Appendices 1 to 18, wherein the transmittance at 600 nm is 50% or more. (Appendix 20) The composition according to any one of Appendices 1 to 19, wherein the composition is an oil-in-water emulsion composition. (Appendix 21) The composition according to Appendices 20, wherein the emulsion is a nanoemulsion and / or microemulsion. (Appendix 22) The composition according to Appendices 20 or 21, wherein the oil droplets in the composition have an average particle size of 100 nm or less. (Appendix 23) A composition for application to skin, comprising the composition according to any one of Appendices 1 to 22. <Stable Bakuchiol> (Appendix 24) A composition comprising bakuchiol and a carotenoid, wherein the mass ratio (B:C) of the bakuchiol (B) to the carotenoid (C) is 1:10 to 2:1. (Appendix 25) The composition according to Appendix 24, wherein the carotenoid is a retinoid. (Appendix 26) The composition according to Appendix 25, wherein the retinoid is retinol palmitate.(Appendix 27) The composition according to any one of Appendices 24 to 26, comprising particles, wherein the particles comprise the bakuchiol and the carotenoid. (Appendix 28) The composition according to any one of Appendices 24 to 27, further comprising an oil. (Appendix 29) The composition according to Appendices 28, wherein the oil is a liquid oil, ester oil, silicone oil, hydrocarbon oil, higher alcohol, and / or fatty acid. (Appendix 30) The composition according to Appendices 29, wherein the oil is squalane. (Appendix 31) The composition according to Appendices 30, wherein the content of the oil is 55 to 99% by mass, based on the total mass of the composition. (Appendix 32) The composition according to any one of Appendices 24 to 31, further comprising a gelling agent. (Appendix 33) The composition according to Appendices 32, wherein the content of the gelling agent is 0.5 to 50% by mass, based on the total mass of the composition. (Appendix 34) The composition according to any one of Appendices 24 to 34, which is an oil gel composition. (Appendix 35) A composition for application to skin, comprising the composition according to any one of Appendices 24 to 34. <Penetrating Bakuchiol> (Appendix 36) A composition comprising liposomes, wherein the liposomes comprise bakuchiol, a complex lipid, and sterols. (Appendix 37) The composition according to Appendices 36, wherein the complex lipid is a phospholipid, glycolipid, lipoprotein, and / or sulfolipid. (Appendix 38) The composition according to Appendices 36 or 37, wherein the complex lipid is a phospholipid. (Appendix 39) The composition according to any one of Appendices 36 to 38, wherein the complex lipid is phosphatidylcholine. (Appendix 40) The composition according to any one of Appendices 36 to 39, wherein the sterol is cholesterol. (Appendix 41) The composition according to any one of Appendices 36 to 40, wherein the content of the bakuchiol is greater than 0% by mass and up to 40% by mass, based on the total mass of the liposome. (Appendix 42) The composition according to any one of Appendices 36 to 41, wherein the content of the complex lipid is 25 to 75% by mass, based on the total mass of the liposome. (Appendix 43) The composition according to any one of Appendices 36 to 42, wherein the content of the sterols is 2 to 20% by mass, based on the total mass of the liposome.(Appendix 44) The composition according to any one of Appendices 36 to 43, wherein the liposomes are pH-responsive liposomes. (Appendix 45) The composition according to any one of Appendices 36 to 44, wherein the liposomes have an average particle size of 50 to 1100 nm. (Appendix 46) The composition according to any one of Appendices 36 to 45, wherein the liposomes further comprise an anionic substance. (Appendix 47) The composition according to Appendices 46, wherein the anionic substance is a fatty acid. (Appendix 48) The composition according to Appendices 46 or 47, wherein the anionic substance is palmitic acid and / or stearic acid. (Appendix 49) The composition according to any one of Appendices 46 to 48, wherein the content of the anionic substance is 2.5 to 15% by mass, based on the total mass of the liposomes. (Appendix 50) The composition according to any one of Appendices 36 to 49, wherein the liposomes further comprise a zwitterionic surfactant. (Appendix 51) The composition according to Appendix 50, wherein the zwitterionic surfactant is at least one selected from the group consisting of N-alkyl-N,N-dimethylamino acid betaines including lauryldimethylaminoacetic acid betaine (lauryl betaine); fatty acid amidoalkyl-N,N-dimethylamino acid betaines including cocamidopropyl betaine and lauramidopropyl betaine; imidazoline-type betaines including sodium cocoamphoacetate and sodium lauroamphoacetate; alkyl sulfobetaines including alkyldimethyltaurines; sulfate-type betaines including alkyldimethylaminoethanol sulfate esters; and phosphate-type betaines including alkyldimethylaminoethanol phosphate esters. (Appendix 52) The composition according to Appendix 50 or 51, wherein the content of the zwitterionic surfactant is 5 to 20% by mass based on the total mass of the liposomes. (Appendix 53) A composition for application to skin, comprising the composition according to any one of Appendices 36 to 52. <μ-Capsule-Type Bakuchiol> (Appendix 54) A composition comprising bakuchiol and silica, wherein the bakuchiol is supported on the silica. (Appendix 55) The composition according to Appendix 54, wherein the content of the bakuchiol is 0.01 to 30% by mass, based on the total mass of the composition.(Appendix 56) The composition according to Appendices 54 or 55, wherein the content of the silica is 60 to 95% by mass, based on the total mass of the composition. (Appendix 57) The composition according to any one of Appendices 54 to 56, wherein the silica comprises porous silica. (Appendix 58) The composition according to any one of Appendices 54 to 57, wherein the bakuchiol is supported at least inside the porous silica. (Appendix 59) The composition according to any one of Appendices 54 to 58, wherein the bakuchiol has an average particle size of 0.01 to 500 μm. (Appendix 60) The composition according to any one of Appendices 54 to 59, further comprising a higher alcohol. (Appendix 61) The composition according to Appendice 60, wherein the higher alcohol is behenyl alcohol. (Appendix 62) The composition according to Appendices 60 or 61, wherein the content of the higher alcohol is greater than 0% by mass and up to 30% by mass, based on the total mass of the composition. (Appendix 63) A composition for application to skin, comprising the composition according to any one of Appendices 54 to 62.

[0182] As described above, the present disclosure provides compositions with improved dispersibility of bakuchiol in aqueous solvents, compositions with improved thermal stability of carotenoids, compositions with improved permeability of bakuchiol through the stratum corneum, and / or powders containing bakuchiol. Therefore, the present invention is extremely useful in the fields of cosmetics, topical skin preparations, etc.

Claims

1. A composition comprising bactiol, a solvent, and a nonionic surfactant and / or anionic surfactant.

2. The composition of claim 1, wherein the solvent is an ester oil, a hydrocarbon oil, and / or an ether oil.

3. The composition according to claim 1 or 2, wherein the solvent is an ester oil.

4. A composition according to any one of claims 1 to 3, wherein the solvent is caprylic / capric triglyceride.

5. A composition according to any one of claims 1 to 4, wherein the nonionic surfactant is an ethylene oxide condensation type, a polyhydric alcohol ester type, and / or a polyhydric alcohol condensation type.

6. A composition according to any one of claims 1 to 5, wherein the nonionic surfactant is of the ethylene oxide condensation type.

7. A composition according to any one of claims 1 to 6, wherein the nonionic surfactant is a polyoxyethylene polyoxypropylene alkyl ether.

8. The composition of claim 7, wherein the polyoxyethylene polyoxypropylene alkyl ethers are polyoxyethylene polyoxypropylene decyl tetradecyl ether, polyoxyethylene polyoxypropylene cetyl ether, polyoxyethylene polyoxypropylene monobutyl ether, polyoxyethylene polyoxypropylene, hydrogenated lanolin, and / or polyoxyethylene polyoxypropylene glycerin ether.

9. The composition according to any one of claims 1 to 8, wherein the anionic surfactant is a carboxylic acid type, a higher alcohol type, a sulfonic acid type, a peptide type, an olefin type, an amino acid type, a taurine type, and / or a lactic acid type.

10. The composition according to any one of claims 1 to 9, wherein the content of the bactiol is 0.001 to 5% by mass, based on the total mass of the composition.

11. The composition according to any one of claims 1 to 10, wherein the content of the solvent is from more than 0% by mass to 5% by mass, based on the total mass of the composition.

12. The composition according to any one of claims 1 to 11, wherein the content of the anionic surfactant and / or the nonionic surfactant is 2 to 20 mass % based on the total mass of the composition.

13. The composition of any one of claims 1 to 12, further comprising a block copolymer.

14. The composition of any one of claims 1 to 13, wherein the block copolymer is a polyamino acid-polyethylene glycol block copolymer, a polylactic acid-polyethylene glycol block copolymer, a polylactic acid-polyglycolic acid block copolymer, a polysarcosine-polyethylene glycol block copolymer and / or a polyoxazoline-polysiloxane block copolymer.

15. The composition of any one of claims 1 to 14, wherein the block copolymer is oligopeptide-56 amide PEG-75 methyl ether.

16. The composition according to any one of claims 13 to 15, wherein the content of the block copolymer is 0.02 to 2 mass % based on the total mass of the composition.

17. The composition of any one of claims 1 to 16, further comprising a dispersion medium.

18. The composition according to claim 17, wherein the content of the dispersion medium is from more than 0% by mass to 5% by mass, based on the total mass of the composition.

19. The composition according to any one of claims 1 to 18, having a transmittance at 600 nm of 50% or more.

20. The composition of any one of claims 1 to 19, which is an oil-in-water emulsion composition.

21. The composition according to claim 20, wherein the emulsion is a nanoemulsion and / or a microemulsion.

22. The composition according to claim 20 or 21, wherein the oil droplets in the composition have an average particle size of 100 nm or less.

23. A composition for application to the skin comprising a composition according to any one of claims 1 to 22.

24. A composition comprising bactiol and a carotenoid, wherein the mass ratio (B:C) of the bactiol (B) to the carotenoid (C) is 1:10 to 2:

1.

25. The composition of claim 24, wherein the carotenoid is a retinoid.

26. The composition of claim 25, wherein the retinoid is retinol palmitate.

27. A composition according to any one of claims 24 to 26, comprising particles, said particles comprising said bactiol and said carotenoid.

28. The composition of any one of claims 24 to 27, further comprising an oil.

29. The composition according to claim 28, wherein the oil is a liquid oil, an ester oil, a silicone oil, a hydrocarbon oil, a higher alcohol, and / or a fatty acid.

30. The composition of claim 29, wherein the oil is squalane.

31. The composition according to claim 30, wherein the content of the oil is 55 to 99 mass % based on the total mass of the composition.

32. The composition of any one of claims 24 to 31, further comprising a gelling agent.

33. The composition according to claim 32, wherein the content of the gelling agent is 0.5 to 50% by mass, based on the total mass of the composition.

34. The composition of any one of claims 24 to 34, which is an oil-gel composition.

35. A composition for application to the skin comprising a composition according to any one of claims 24 to 34.

36. A composition comprising a liposome, the liposome comprising bactiol, a complex lipid, and a sterol.

37. The composition of claim 36, wherein the complex lipid is a phospholipid, glycolipid, lipoprotein, and / or sulfolipid.

38. The composition of claim 36 or 37, wherein the complex lipid is a phospholipid.

39. A composition according to any one of claims 36 to 38, wherein the complex lipid is a phosphatidylcholine.

40. The composition of any one of claims 36 to 39, wherein the sterol is cholesterol.

41. The composition of any one of claims 36 to 40, wherein the bactiol content is greater than 0% by weight to 40% by weight, based on the total weight of the liposome.

42. The composition according to any one of claims 36 to 41, wherein the content of the complex lipid is 25 to 75 mass% based on the total mass of the liposome.

43. The composition according to any one of claims 36 to 42, wherein the content of the sterols is 2 to 20% by mass, based on the total mass of the liposome.

44. The composition of any one of claims 36 to 43, wherein the liposome is a pH-responsive liposome.

45. The composition of any one of claims 36 to 44, wherein the liposomes have an average particle size of 50 to 1100 nm.

46. ​​The composition of any one of claims 36 to 45, wherein the liposome further comprises an anionic substance.

47. The composition of claim 46, wherein the anionic material is a fatty acid.

48. The composition of claim 46 or 47, wherein the anionic material is palmitic acid and / or stearic acid.

49. The composition according to any one of claims 46 to 48, wherein the content of the anionic substance is 2.5 to 15% by mass, based on the total mass of the liposome.

50. The composition of any one of claims 36 to 49, wherein the liposome further comprises a zwitterionic surfactant.

51. The composition of claim 50, wherein the zwitterionic surfactant is at least one selected from the group consisting of N-alkyl-N,N-dimethylamino acid betaines including lauryl dimethylaminoacetic acid betaine (lauryl betaine); fatty acid amidoalkyl-N,N-dimethylamino acid betaines including cocamidopropyl betaine and lauramidopropyl betaine; imidazoline-type betaines including sodium cocoamphoacetate and sodium lauroamphoacetate; alkyl sulfobetaines including alkyldimethyltaurine; sulfate-type betaines including alkyldimethylaminoethanol sulfate; and phosphate-type betaines including alkyldimethylaminoethanol phosphate.

52. The composition according to claim 50 or 51, wherein the content of the zwitterionic surfactant is 5 to 20% by mass, based on the total mass of the liposome.

53. A composition for application to the skin comprising a composition according to any one of claims 36 to 52.

54. A composition comprising bactiol and silica, wherein said bactiol is supported on said silica.

55. The composition of claim 54, wherein the content of bactiol is 0.01 to 30% by weight, based on the total weight of the composition.

56. The composition according to claim 54 or 55, wherein the content of the silica is 60 to 95 mass % based on the total mass of the composition.

57. The composition of any one of claims 54 to 56, wherein the silica comprises porous silica.

58. A composition according to any one of claims 54 to 57, wherein the bactiol is supported at least within the interior of the porous silica.

59. The composition of any one of claims 54 to 58, having an average particle size of 0.01 to 500 µm.

60. The composition of any one of claims 54 to 59, further comprising a higher alcohol.

61. The composition of claim 60, wherein the higher alcohol is behenyl alcohol.

62. The composition described in claim 60 or 61, wherein the content of the higher alcohol is from more than 0% by mass to 30% by mass, based on the total mass of the composition.

63. A composition for application to the skin comprising a composition according to any one of claims 54 to 62.

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