WO2009154269A1 - 毛髪化粧料 - Google Patents
毛髪化粧料 Download PDFInfo
- Publication number
- WO2009154269A1 WO2009154269A1 PCT/JP2009/061190 JP2009061190W WO2009154269A1 WO 2009154269 A1 WO2009154269 A1 WO 2009154269A1 JP 2009061190 W JP2009061190 W JP 2009061190W WO 2009154269 A1 WO2009154269 A1 WO 2009154269A1
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- WO
- WIPO (PCT)
- Prior art keywords
- hair
- residue
- hair cosmetic
- cosmetic composition
- triazine
- Prior art date
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
Definitions
- the present invention relates to a hair cosmetic, and more specifically, for use in hair washing and styling, which contains a UV-absorbing agent having a poorly soluble triazine group that has an excellent UV protection effect and has a good feeling in use.
- This invention relates to a hair cosmetic that can be used.
- blending an ultraviolet absorber in hair cosmetics is an effective means for preventing hair damage due to contact with ultraviolet rays due to exposure to sunlight or the like.
- the types of ultraviolet absorbers having a protective effect against UVA are limited, and many are hardly soluble. Therefore, to prevent hair damage by blending a poorly soluble ultraviolet absorber, it is necessary to increase the blending amount of a surfactant and the like, and as a result, the use feeling of the hair cosmetics is deteriorated. There were drawbacks.
- the problem to be solved by the present invention is to establish a means for stably blending a sparingly soluble UV absorber and apply it to the hair cosmetic, whereby the hair cosmetic has both an effect of preventing damage to hair by UV rays and an excellent feeling of use. Is to provide.
- the inventor of the present invention has a phytosterol skeleton or a phytostanol skeleton as a hydrophobic molecule with respect to an ultraviolet absorbent having a triazine group, which is a poorly soluble ultraviolet absorbent in which excellent UVA absorption is often observed.
- a surfactant having a polyoxyethylene chain (POE chain) or a block chain of a polyoxyethylene chain (POE chain) and a polyoxypropylene chain (POP chain) together with an ultraviolet absorber having a triazine group As a result, it was revealed that the hair was protected from oxidative damage due to ultraviolet rays and was excellent in usability.
- this invention is invention which provides the hair cosmetics (henceforth this invention hair cosmetics) containing the following component (1) and (2).
- a Polyoxy-lower alkylene addition compound represented by the following formula (I) hereinafter also referred to as compound (I)
- UV absorber having a triazine group (hereinafter also referred to as triazine ultraviolet absorber)
- hair cosmetics to which the present invention can be applied include shampoos, rinses, rinse-in shampoos, hair conditioners and other hair cleaning agents; hair foams, hair mousses (registered trademark), hair sprays, hair mists, hair gels, Hair treatment agents such as set lotions, curler lotions, hair liquids, hair waxes, hair treatments (hair creams, hair blows, etc.), hair nourishing agents, hair dyes, permanent wave agents, hair straighteners, etc. "" Means "hair treatment composition"), and the present invention can also be applied.
- the present invention provides a hair cosmetic that can effectively suppress damage to hair against ultraviolet rays and is excellent in usability.
- phytosterol which is a parent compound of a phytosterol residue that R can take
- phytosterol residues that R can take there are sitosterol residues, campesterol residues, stigmasterol residues, brassicasterol residues, avenasterol residues, ergosterol residues, and the like.
- the compound (I) to be blended in the water-containing composition of the present invention can be a mixture of two or more compounds having different phytosterol residues.
- phytostanol which is a parent compound of a phytostanol residue that R can take
- the compound (I) to be blended in the hair cosmetic composition of the present invention can be a mixture of two or more compounds having different phytostanol residues.
- the compound (I) is a mixture of a compound in which R has one or more phytosterol residues and a compound having one or more phytostanol residues in the hair cosmetic composition of the present invention. It is also possible to mix.
- Compound (I) is a polyoxy lower alkylene addition compound in which the polyoxy lower alkylene chain is a POE chain or a block chain of a POP chain and a POE chain.
- the compounding amount of the compound (I) in the hair cosmetic composition of the present invention is preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass with respect to the cosmetic. If the blending amount is less than 0.01% by mass, it is difficult to disperse or solubilize the triazine-based UV absorber to such an extent that a substantial UV shielding effect is observed. There is a tendency to cause stickiness of the preparation. Further, the compounding amount of the compound (I) largely depends on the relative relationship with the compounding amount of the triazine-based ultraviolet absorber.
- the upper limit of the abundance ratio of the compound (I) to the triazine-based ultraviolet absorber is preferably 1 or more in terms of mass ratio, with the upper limit value of the compounding amount of the compound (I) as a limit index, and 3 or more. It is particularly preferred.
- the suitable value of the minimum of the compounding quantity of compound (I) can also be prescribed
- composition of triazine UV absorber In the hair cosmetic composition of the present invention, it is necessary to blend one or more triazine ultraviolet absorbers, that is, ultraviolet absorbers having a triazine group.
- the triazine-based ultraviolet absorber is hardly soluble in water, but the solubility in a solvent other than water is not particularly limited.
- the blending of the triazine-based UV absorber does not interfere with the selective blending of other poorly water-soluble UV absorbers or water-soluble UV absorbers.
- triazine ultraviolet absorber examples include bisresorcinyl triazine, more specifically, bisethylhexyloxyphenol methoxyphenyltriazine (also known as: 2,4-bis ⁇ [4- (2-ethylhexyloxy) -2- Hydroxy] phenyl ⁇ -6- (4-methoxyphenyl) 1,3,5-triazine, commercially available products such as TINOSORB S, Ciba Specialty Chemicals), octyl triazone (also known as 2,4,6) Tris ⁇ 4- (2-ethylhexyloxycarbonyl) anilino ⁇ 1,3,5-triazine or 2,4,6-trianilino-p- (carbo-2′-ethylhexyl-1′-oxy) -1, 3,5-triazine, commercially available product ubinal T150 (UVINUL) T150), BASF), 2- [2-hydroxy 4- (2-ethylhexy
- the blending amount of the triazine-based ultraviolet absorber in the hair cosmetic composition of the present invention is preferably in accordance with the blending ratio with the compound (I) described above, but is generally preferably 0.001 to 3% by mass of the cosmetic composition. More preferably, the content is 0.001 to 1% by mass. If the blending amount is less than 0.001% by mass, it is difficult to suppress hair damage due to the substantial UV shielding action in the hair cosmetic composition of the present invention, and blending exceeding 3% by mass is a triazine UV absorber. Will exceed the practical limit of solubility.
- the hair cosmetic composition of the present invention does not interfere with the blending of UV absorbers other than triazine-based UV absorbers.
- Anthranilic acid ultraviolet absorbers eg, homomenthyl-N-acetylanthranilate
- salicylic acid ultraviolet absorbers eg, amyl salicylate, menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate
- Cinnamate UV absorbers eg octylcinnamate, ethyl-4-isopropylcinnamate, ethyl-2,4-diisopropylcinnamate, methyl-2,4-diisopropyl
- Cinnamate propyl-p-methoxycinnamate, isopropyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl- ⁇ -cyano- ⁇ -phenylcinnamate, 2-ethylhexyl- ⁇ -cyano- ⁇
- UV absorbers can be blended regardless of water solubility or poor solubility, and the blending amount thereof can be freely selected as long as the effects of the present invention are not hindered.
- the hair cosmetic composition of the present invention can be made into a water-containing composition, that is, an aqueous hair cosmetic composition, by blending water.
- the water blended into the hair cosmetic composition of the present invention is usually ion-exchanged water, purified water, or tap water.
- the blending amount of water in the hair cosmetic composition of the present invention is the remaining amount of the total amount of compound (1) and triazine-based ultraviolet absorber in cosmetics, or compound (1), triazine-based ultraviolet absorber in cosmetics, and The remaining amount of general blending components can be contained.
- the hair cosmetic composition of the present invention containing water, a compound having a phytosterol skeleton or a phytostanol skeleton as a hydrophobic molecule and a surfactant having a POE chain or POE chain and POP chain as a hydrophilic molecule
- a compound having a phytosterol skeleton or a phytostanol skeleton as a hydrophobic molecule and a surfactant having a POE chain or POE chain and POP chain as a hydrophilic molecule
- the hair cosmetic composition of the present invention can be applied to anhydrous compositions such as hair sprays and hair oils, or water-containing compositions such as shampoos, conditioners, hair waxes, hair treatments and hair creams.
- anhydrous compositions such as hair sprays and hair oils
- water-containing compositions such as shampoos, conditioners, hair waxes, hair treatments and hair creams.
- each part can be mixed and manufactured.
- a water-containing composition although it varies depending on the form of the selected hair cosmetic, for example, an oil phase part in which at least a triazine-based ultraviolet absorber is dissolved or dispersed in Compound (I) is prepared, and this is added to water. Mixing in phase parts and solubilizing or dispersing is one of basic manufacturing methods.
- the hair cosmetic composition of the present invention is typically used as (1) a hair cleaning agent and (2) a hair treatment agent.
- the hair cosmetic composition of the present invention can be blended with these selectable forms and general components as required, for example, to produce a hair cosmetic composition in a desired form as described above.
- hair cosmetics of the present invention are roughly classified into hair cleaning agents and hair treatment agents.
- anionic surfactant examples include, for example, alkyl sulfates, alkyl ether sulfates, higher fatty acid salts, alkyl sulfonates, POE alkyl sulfates, alkyl benzene sulfonates, N-acyl sarcosine salts, Examples thereof include N-acyl isethionate, N-acyl glutamate, alpha olefin sulfonate, alkyl ether acetate, and POE alkyl ether acetate.
- cationic surfactant examples include, for example, alkyltrimethylammonium salt, dialkyldimethylammonium salt, alkyldimethylbenzylammonium salt, alkylisoquinolinium salt, dialkylmorpholinium salt, POE alkylamine; alkyl Examples include amine salts; polyamine fatty acid derivatives; amyl alcohol fatty acid derivatives; benzalkonium chloride; benzethonium chloride and the like.
- nonionic surfactant examples include, for example, alkanolamide, glycerin fatty acid ester, polyoxyalkylene alkyl ether, polyoxyalkylene glycol, polyoxyalkylene sorbitan fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbit fatty acid ester.
- Sorbitol fatty acid ester polyoxyalkylene glycerin fatty acid ester, polyoxyalkylene fatty acid ester, polyoxyalkylene alkyl phenyl ether, tetrapolyoxyalkylene ethylenediamine condensate, polyoxyalkylene ether, sucrose fatty acid ester, polyoxyalkylene fatty acid amide, Polyoxyalkylene glycol fatty acid ester, polyoxyalkylene castor oil derivative, polyoxy Alkylene hardened castor oil derivatives, alkyl polyglucoside, and the like.
- amphoteric surfactants include alkyl imidazolinium betaines, alkylamidopropyl betaines, alkylaminocarboxylic acids, alkylsulfobetaines, alkylamine oxides, alkylcarboxybetaines, and alkylbetaines.
- oil components include olive oil, jojoba oil, castor oil, lanolin, beeswax, carnauba wax, liquid paraffin, squalane, microcrystalline wax, stearic acid, isostearic acid, oleic acid, cetanol, stearyl alcohol, octanoic acid
- examples include cetyl, isopropyl myristate, dimethylpolysiloxane, methylphenylpolysiloxane, silicone resin, silicone rubber, amino-modified polysiloxane, and polyether-modified polysiloxane.
- humectant examples include, for example, polyethylene glycol, glycerin, 1,3-butanediol, 1,2-pentanediol, erythritol, sorbitol, xylitol, maltitol, propylene glycol, dipropylene glycol, diglycerin, Examples include sodium pyrrolidone carboxylate, lactic acid, and sodium lactate.
- polymer viscosity modifier examples include methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, and the like.
- Hair cleansing agent For example, when a shampoo is selected as the hair cleansing agent, the above anionic surfactant can be used as the foaming agent. It is also possible to mix a nonionic surfactant. Furthermore, cationic polymers (conditioning agents) such as oil and cationized cellulose, the above-mentioned moisturizers, thickeners, the above-mentioned viscosity modifiers, pH adjusters, emulsions, pigments, sequestering agents, preservatives Etc. are mentioned as general ingredients of shampoos. Further, for the purpose of preventing dandruff and stagnation, trichlorocarbanilide, sulfur, salicylic acid, zinc pyrithione, isopropylmethylphenol and the like can be blended.
- conditioning agents such as oil and cationized cellulose, the above-mentioned moisturizers, thickeners, the above-mentioned viscosity modifiers, pH adjusters, emulsions, pigments, sequestering agents,
- a rinse or hair conditioner (hereinafter also referred to as rinse) is selected as a hair cleansing agent
- the above cationic surfactant can be blended, and other oils and moisturizers can be added. It is also possible to mix.
- the hair cosmetic composition of the present invention is a transparent rinse or the like in which an oil is dissolved in an aqueous solution of a cationic surfactant, it forms a layered structure gel formed by a cationic surfactant, a higher alcohol and water.
- the emulsification system rinse may be used.
- a rinse-in shampoo for example, the above-mentioned anionic surfactant is used as the main cleaning agent, and the above-mentioned cationic surfactant, silicone, and hydrocarbon are used as the conditioning agent.
- System oils and the like can be blended.
- nonionic polymers polyvinyl pyrrolidone, polyvinyl pyrrolidone / vinyl acetate copolymer, etc.
- anionic polymers acrylic ester / methacrylic ester copolymer, vinyl methyl ether / Butyl maleate copolymer, etc.
- cationic polymer vinyl pyrrolidone / dimethylaminoethyl methacrylate copolymer cationized product, etc.
- amphoteric polymer hydroxypropyl acrylate / butylaminoethyl methacrylate / octylamide acrylate copolymer
- the above oils, humectants, general emulsifying surfactants and the like can be blended.
- the present invention can be applied to the stock solution as in the case of the above-mentioned hair foam.
- main components of hair spray for example, polyvinylpyrrolidone or a vinyl acetate copolymer thereof, an acrylic resin alkanolamine liquid, a film forming agent such as vinyl methyl ether / butyl maleate copolymer, cetyl alcohol, stearyl alcohol, isostearyl Alcohols, higher alcohols such as cetanol, solid oils such as lanolin derivatives, silicone oils and the like can be blended.
- carboxyvinyl polymer When a hair gel is selected as the hair treatment agent, carboxyvinyl polymer, methylcellulose, carrageenan, and the like are blended as water-soluble polymers that form a thickening system.
- the above set agent and moisturizing agent, an alkali agent, a general emulsifying surfactant, a sequestering agent, and the like can be blended.
- a set lotion or curler lotion is selected as the hair treatment agent, for example, the above-mentioned set agent, moisturizing agent, plasticizer and the like can be blended.
- a hair liquid for example, polyalkylene glycol or the like can be blended as a hair styling agent.
- hair wax is selected as the hair treatment agent
- solid oil candelilla wax, carnauba wax, beeswax and other waxes, liquid paraffin, petrolatum, ceresin, microcrystalline wax and other hydrocarbon oils, lauric acid, myristic acid Higher fatty acids such as the above, higher alcohols described above, etc.
- fluid oils semi-solid oils, the above thickeners, the above moisturizers, general emulsifying surfactants, and the like.
- oils and fats such as olive oil, camellia oil, and synthetic triglycerides; the above hydrocarbon oils, the above waxes, the above higher fatty acids; and higher oils such as isopropyl myristate and butyl stearate Fatty acid esters; the above higher alcohols; the above thickeners; organic amines or inorganic alkalis, preservatives, sequestering agents, and the like.
- the above cationic surfactant ethanol, silicone derivative, the above moisturizer, the above oil, the protein hydrolyzate, the preservative, and the like can be blended.
- Example A when the hair cosmetic composition of the present invention is a hair cleanser and Example B which is also a hair treatment agent, and each of the hydrophilic molecules of Compound (I) is a POE chain. And a case where the block chain is a POE chain and a POP chain.
- a hair sample treatment solution is obtained by immersing 600 mg of hair of a 15-year-old woman in a mixed solution containing 30% by weight of urea, 20% by weight of thiourea, 5% by weight of dithiothreitol, and 8 ml of 25 mM Tris-HCl buffer (pH 8.5). This was held at 50 ° C. for 4 days to obtain a hair keratin protein solution. The powder-extracted hair was removed from the solution by filtration to obtain a hair keratin protein solution.
- the amount of increase in fluorescence luminance was measured according to the following experimental method.
- Example 1 Contact between keratin film and sample
- each sample (Example and Comparative Example) diluted 4 times with distilled water on a petri dish on which the keratin film was placed 3 g And shake for 3 minutes (whipped in a petri dish for shampoo). Thereafter, the sample is discarded, rinsed 7 times with 1.5 ml of distilled water and dried.
- Example (B) hair treatment agent
- a quartz glass plate (with no UV absorption and a thickness of 1 mm) having a size ( ⁇ 34 mm) suitable for a petri dish containing a keratin film was prepared, and each sample ( Examples and Comparative Examples 1 ml is applied and dried at 50 ° C. for 24 hours.
- An aluminum foil is placed on the surface half of the keratin film so as not to be exposed to light and shielded, and a quartz glass treated with the sample is placed thereon.
- Example (B) Irradiation with ultraviolet rays
- irradiation is performed for 10 minutes using an artificial sun (Solar simulator, 15 mW / cm 2 : 290 to 390 nm). When irradiating, it is shielded with aluminum foil so that light does not hit the surface half of the film. This sample processing to artificial sun irradiation is repeated seven times as a whole.
- Example (B) hair treatment agent
- irradiation is performed for 1 hour (54 J / cm 2 ) using an artificial sun (Solar simulator, 15 mW / cm 2 : 290 to 390 nm).
- the amount of increase in fluorescence brightness was less than 50% as compared with the amount of increase in fluorescence brightness of the (A) and (B) component-free sample.
- B The amount of increase in fluorescence brightness was 50% or more and less than 80%, compared to the amount of increase in fluorescence brightness of the sample containing no component (A) or (B).
- ⁇ The amount of increase in fluorescence brightness was 80% or more and less than 100% as compared to the amount of increase in fluorescence brightness of the target samples without component (A) and (B).
- X The amount of increase in fluorescence brightness was 100% or more compared to the amount of increase in fluorescence brightness of the sample containing no component (A) or (B).
- Example A-1 hair wash A hair shampoo was prepared according to the formulation shown in Table 1 below.
- citric acid, L-glutamic acid, sodium chloride, sodium benzoate, disodium edetate and sodium hydroxide were added to purified water and dissolved at 70 ° C., and this was dissolved in sodium cocoylmethyl taurate, N-lauroyl-N ′.
- -Carboxymethyl-N '-(2-hydroxyethyl) ethylenediamine sodium and dodecane-1,2-diol sodium acetate ether were added and stirred.
- POE phytosterol or POE hydrogenated castor oil and 2,4,6-tris [4- (2-ethylhexyloxycarbonyl) anilino] 1,3,5-triazine or 4-tert-butyl-4'-methoxybenzoyl
- a solution prepared by melting methane or 2-ethylhexyl paramethoxycinnamate at 80 ° C. was prepared and added to the above solution. Finally, a fragrance was further added and cooled to room temperature to obtain a hair shampoo.
- the hair cosmetics of the present invention have an excellent UV protection effect in any hair washing cosmetic preparation, and further, the feel of hair (passy) It was also excellent.
- an example using a type other than the triazine type UV absorber as the UV absorber to be blended (Comparative Examples A1 to A3) and a type having no phytosteryl skeleton as the surfactant (Comparison) Example A4) was examined, but none of the comparative examples showed a sufficient UV protection effect and a feeling of use (no sagging).
- Example B-1 Hair treatment agent Hair water was prepared according to the formulation shown in Table 2 and Table 3 below.
- Example B1 in which a surfactant having a phytosteryl skeleton and an ultraviolet absorber having ultraviolet absorption in the UVA to UVB region were used, both the ultraviolet protection effect and the touch feeling were excellent.
- Examples B2 to B4 a surfactant having a phytosteryl skeleton and an ultraviolet absorber having ultraviolet absorption in the UVA to UVB region are used.
- an activator having a phytosteryl skeleton By adding an activator having a phytosteryl skeleton to the ultraviolet absorber, It was found that the hair damage protection effect and feel were excellent.
- B2 and B3 in which the mass ratio of the activator having a phytosteryl skeleton to the ultraviolet absorber is 1 or more, has a very good touch feeling and also has a very poor solubility in an ultraviolet absorber that is hardly soluble in water. It was.
- ⁇ Manufacturing method> (8) to (10) were mixed to make uniform, (1), (2), (7) and (20) were mixed, and an (emulsified part) was prepared using a homomixer. (3), (6), (12) to (19) are dissolved, neutralized with (11) and then mixed with (emulsified parts), then dissolved at 80 ° C (4) and (5) are mixed. The desired hair cream was obtained.
- ⁇ Manufacturing method> Dissolve a part of (16) in (5) and (11), and emulsify (1), (2), (9), (15), and (17) with a homomixer to create (emulsified part) To do. (10), (12), (13) and (16) are stirred and dissolved at 90 ° C and rapidly cooled to create a transparent wax fine dispersion. (Emulsified part) is stirred and mixed and heated to 70 ° C. Warmed (3), (4), (6) and (14) are mixed, and (7) and (8) heated to 80 ° C. are mixed to obtain a stock solution. The stock solution was filled into a can using liquefied natural gas as a propellant to obtain a foam hair wax.
- Example A-2 hair wash
- a hair conditioner was prepared according to the formulation shown in Table 4 below.
- POE (30) POP (10) phytosterol or POE hydrogenated castor oil and 2,4,6-tris [4- (2-ethylhexyloxycarbonyl) anilino] 1,3,5-triazine or 4-tert-butyl-
- a solution prepared by melting 4′-methoxybenzoylmethane or 2-ethylhexyl paramethoxycinnamate at 80 ° C. was prepared and added to the above solution. Finally, a fragrance was further added and cooled to room temperature to obtain a hair conditioner.
- the hair cosmetics of the present invention have an excellent UV protection effect in any hair washing cosmetic preparation, and further, the feel of hair (passy) It was also excellent.
- an example using a type other than the triazine type UV absorber as the UV absorber to be blended (Comparative Examples A5 to A7) and a type having no phytosteryl skeleton as the surfactant (Comparison) Example A8) was examined, but none of the comparative examples showed a sufficient UV protection effect and a feeling of use (no sagging).
- Example B Hair treatment agent Hair water was prepared according to the formulation shown in Table 5 and Table 6 below.
- Example B5 in which a surfactant having a phytosteryl skeleton and an ultraviolet absorber having ultraviolet absorption in the UVA to UVB region were used, both the ultraviolet protection effect and the touch feeling were excellent.
- Comparative Example B4 has a problem in the ultraviolet protection effect because an ultraviolet absorber having ultraviolet absorption in the UVA to UVB region is not used.
- Examples B6 and B7 a surfactant having a phytosteryl skeleton and an ultraviolet absorber having ultraviolet absorption in the UVA to UVB region are used, and the ultraviolet absorber corresponds to a triazine derivative, The touch was very good.
- a solution obtained by dissolving (3) and (14) to (16) in (17) is referred to as (aqueous phase).
- a solution obtained by dissolving (1), (2), (6) to (11) at 90 ° C. is referred to as (oil phase).
- (12) is stirred into the aqueous phase and heated to 80 ° C. (Oil phase) is added to this while stirring, emulsified using a homomixer, and neutralized in (13). Thereafter, (4) and (5) dissolved at 80 ° C. were stirred and mixed, degassed and cooled to obtain the desired hair wax.
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Abstract
Description
(1)下記式(I)にて表されるポリオキシ低級アルキレン付加化合物(以下、化合物(I)ともいう)
(2)トリアジン基を有する紫外線吸収剤(以下、トリアジン系紫外線吸収剤ともいう)
本発明毛髪化粧料においては、上述のように、水と難溶性のトリアジン系紫外線吸収剤と共に、化合物(I)が配合される。化合物(I)は、後述するように、上記式(I)の範囲内の1種のみの化合物として本発明毛髪化粧料に配合することも可能であり、異なる2種以上の化合物の混合物であってもよい。
本発明毛髪化粧料においては、トリアジン系紫外線吸収剤、すなわちトリアジン基を有する紫外線吸収剤、を1種又は2種以上配合することが必要である。トリアジン系紫外線吸収剤は水難溶性であるが、水以外の溶媒に対する溶解性については特に限定されるものではない。なお、このトリアジン系紫外線吸収剤の配合は、他の水難溶性の紫外線吸収剤や水溶性の紫外線吸収剤の選択的な配合を妨げない。
本発明毛髪化粧料は、水を配合して、含水組成物、すなわち、水性の毛髪化粧料とすることができる。この場合、本発明毛髪化粧料に配合する水は、通常は、イオン交換水、精製水、又は、水道水である。本発明毛髪化粧料における水の配合量は、化粧料における、化合物(1)及びトリアジン系紫外線吸収剤の総量の残量、あるいは、化粧料における、化合物(1)、トリアジン系紫外線吸収剤、及び、一般的な配合成分の残量を含有させることができる。
本発明毛髪化粧料においては、ヘアスプレーやヘアオイル等の無水の組成物、あるいはシャンプー、コンディショナー、ヘアワックス、ヘアトリートメント、ヘアクリーム等の含水組成物に適用可能である。
例えば、頭髪洗浄料としてシャンプーを選択する場合には、起泡剤として、上記の陰イオン性界面活性剤を用いることが可能であり、さらに、上記の両性界面活性剤や非イオン型界面活性剤を配合することも可能である。さらに、油分、カチオン化セルロース等のカチオン性高分子(コンディショニング剤)、上記の保湿剤、増粘剤、上記の粘度調整剤、pH調整剤、乳濁剤、色素、金属イオン封鎖剤、防腐剤等がシャンプーの一般的配合成分として挙げられる。また、ふけや痒みの防止を目的として、トリクロロカルバニリド、イオウ、サリチル酸、ジンクピリチオン、イソプロピルメチルフェノール等を配合することも可能である。
仕上げ用毛髪化粧料として、ヘアフォームやヘアムース(登録商標)を用いる場合には、本発明は原液において適用される。当該原液には、一般的な成分として、非イオン性ポリマー(ポリビニルピロリドン、ポリビニルピロリドン/酢酸ビニル共重合体等)、陰イオン性ポリマー(アクリル酸エステル/メタクリル酸エステル共重合体、ビニルメチルエーテル/マレイン酸ブチル共重合体等)、陽イオン性ポリマー(ビニルピロリドン/ジメチルアミノエチルメタクリレート共重合体カチオン化物等)、両性ポリマー(アクリル酸ヒドロキシプロピル/メタクリル酸ブチルアミノエチル/アクリル酸オクチルアミド共重合体等)に代表されるセット剤;上記の油分、保湿剤、一般的な乳化用の界面活性剤等を配合することが可能である。
(1)紫外線防御効果の検討
毛髪から抽出したタンパク質で調製されたケラチンフィルムを用いて、各試料を塗布した時の紫外線防御効果を測定する。
15才女性の毛髪600mgを、尿素30質量%、チオ尿素20質量%、ジチオスレイトール5質量%、25mMトリス-塩酸緩衝液(pH8.5)8mlを含む混合液に浸漬して毛髪サンプル処理液とし、これを50℃にて4日間保持して、毛髪ケラチン蛋白質溶解液を得た。この溶解液からろ過により末抽出毛髪を取り除き、毛髪ケラチン蛋白質溶液とした。この蛋白質溶液3.5mgへ、100mM酢酸水溶液6mlを添加、混合し、この混合溶液を、水を満たしたシャーレ(直径35mm)へ静かにキャストした。固体化した後、蒸留水を含む展開用溶液を数回交換して、ゲル中の溶液を蒸留水に置換した。最後に蒸留水を除き、シリカゲルを含む箱内で十分に乾燥し、目的のケラチンフィルムを得た。
(a)ケラチンフィルムと試料の接触
下記実施例(A)(頭髪洗浄料)においては、ケラチンフィルムを載置したシャーレ上に蒸留水で4倍に薄めた各試料(実施例及び比較例)3gを注ぎ、(シャンプーの場合はシャーレ内で泡立てて)3分間振とうさせる。その後、試料を廃棄し、蒸留水1.5mlで7回洗い流し、乾燥させる。
下記実施例(A)(頭髪洗浄料)においては、人工太陽(Solar simulator,15mW/cm2:290~390nm)を用いて、10分間照射する。照射の際にはフィルムの表面半分に光が当たらないようにアルミホイルで遮蔽する。この試料処理~人工太陽照射を全体として7回繰り返す。
5-FTSCをジメチルスルホキシド溶液に溶解させ、5mMの5-FTSC溶液を調製する。次に水酸化ナトリウムを用いて、pH5.5に調整した0.1MのMES(2-Morpholino ethanesulfonic acid,monohydrate)に、先に調製した5mMの5-FTSC溶液を溶解させ、20μMの5-FTSC/0.1M MES-NA(pH5.5)染色液を調製する。染色方法は、20μMの5-FTSC/0.1M MES-NA(pH5.5)染色液を、ケラチンフィルムを含むシャーレ上に注ぎ、室温で15分間振とうするというものである。染色が十分になされた後、染色液の除去のために、洗浄操作を行う。シャーレから振とう液を廃棄した後、初めに2×SSC-0.1%SDS溶液を注ぎ、室温で5分間振とうする。洗浄液を換えて再度繰り返す。次に0.2×SSC-0.1%SDS溶液を注ぎ50℃で20分間静置する。洗浄液を換えて再度繰り返す。その後蒸留水を注ぎ室温で2分間振とうする。蒸留水を変えて全部で6回繰り返す。上記染色液の調製、染色、洗浄の工程はすべて遮光下において行う。
◎・・・(A)、(B)成分無配合対象試料の蛍光輝度増加量に比べて、蛍光輝度増加量が50%未満であった。
○・・・(A)、(B)成分無配合対象試料の蛍光輝度増加量に比べて、蛍光輝度増加量が50%以上80%未満であった。
△・・・(A)、(B)成分無配合対象試料の蛍光輝度増加量に比べて、蛍光輝度増加量が80%以上100%未満であった。
×・・・(A)、(B)成分無配合対象試料の蛍光輝度増加量に比べて、蛍光輝度増加量が100%以上であった。
健常毛2gの毛束に各試料(実施例及び比較例)0.5gを塗布(シャンプーの場合は泡立てる)した後、流水で試料を洗い流し、乾燥させる。処理後、人工太陽(Solar simulator,15mW/cm2:290~390nm)を10分間照射(9J/cm2)する。さらに試料で処理後照射することを全部で7回繰り返した後、専門パネル10名が未処理の毛束と比べて、手触り感(ぱさつきのなさ)を、以下の基準により評価した。
○・・・専門パネル6名以上8名未満が未処理の毛束と比べて、ぱさつきを認めなかった。
△・・・専門パネル3名以上6名未満が未処理の毛束と比べて、ぱさつきを認めなかった。
×・・・専門パネル3名未満が未処理の毛束と比べて、ぱさつきを認めなかった。
<化合物(I)の親水分子がPOE鎖(m=0)である場合>
(1)実施例A-1(頭髪洗浄料)
下記表1に示す配合処方によってヘアシャンプーを調製した。
下記表2及び表3に示す配合処方によってヘアウォーターを調製した。
配合成分 配合量(質量%)
(1)ココイルメチルタウリンナトリウム 20.0
(2)N-ラウロイル-N´-カルボキシメチル-N´-(2-
ヒドロキシエチル)エチレンジアミンナトリウム 8.0
(3)ドデカン-1,2-ジオール酢酸エーテルナトリウム 3.0
(4)POE(30)フィトステロール 2.0
(5)2,4,6-トリス[4-(2-エチルヘキシルオキシカルボニル)
アニリノ]-1,3,5-トリアジン 0.2
(6)クエン酸 0.01
(7)L-グルタミン酸 0.2
(8)塩化ナトリウム 1.0
(9)安息香酸ナトリウム 0.5
(10)エデト酸2ナトリウム 適量
(11)水酸化ナトリウム 0.01
(12)精製水 残余
(13)香料 適量
表1のヘアシャンプーと同じ。
配合成分 配合量(質量%)
(1)揮発性イソパラフィン 5.0
(2)ジメチルポリシロキサン 2.0
(3)エタノール 5.0
(4)POE(25)フィトステリル 0.6
(5)2,4-ビス-[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}-
フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン 0.1
(6)グリセリン 5.0
(7)ポリオキシプロピレンデカグリセリルエーテル 5.0
(8)イソステアリン酸 1.0
(9)POE硬化ヒマシ油 0.5
(10)2-アルキル-N-カルボキシメチル-N-
ヒドロキシエチルイミダゾリニウムベタイン 4.0
(11)水酸化ナトリウム 0.15
(12)パラオキシ安息香酸エステル 適量
(13)フェノキシエタノール 適量
(14)エデト酸3ナトリウム 適量
(15)キサンタンガム 0.5
(16)カラギーナン 0.3
(17)酢酸ビニル.ビニルピロリドン共重合体 2.0
(18)カルボキシビニルポリマー 0.5
(19)精製水 残余
(20)高重合メチルポリシロキサン 2.0
(8)~(10)を混合して均一にし、(1)、(2)、(7)、(20)を混合し、ホモミキサーを用いて(乳化パーツ)を作成した。(3)、(6)、(12)~(19)を溶解し、(11)で中和した後に(乳化パーツ)を混合し、80℃で溶解した(4)、(5)を混合し、目的とするヘアクリームを得た。
配合成分 配合量(質量%)
(1)流動パラフィン 5.0
(2)ジメチルポリシロキサン 5.0
(3)グリセリン 5.0
(4)プロピレングリコール 5.0
(5)1,3-ブチレングリコール 5.0
(6)ブチルエチルプロパンジオール 0.5
(7)POE(30)フィトステリル 0.8
(8)2,4,6-トリス[4-(2-エチルヘキシルオキシカルボニル)
アニリノ]-1,3,5-トリアジン 0.05
(9)ホホバ油 1.0
(10)カルナウバロウ 5.0
(11)POE硬化ヒマシ油 2.0
(12)POEベヘニルエーテル 5.0
(13)2-アルキル-N-カルボキシメチル-N-
ヒドロキシエチルイミダゾリニウムベタイン 7.0
(14)フェノキシエタノール 0.5
(15)高重合ジメチルポリシロキサン 0.5
(16)精製水 残余
(17)香料 適量
原液/噴射剤=90/10(L.P.G. 0.43MPa)
(5)と(11)に一部の(16)を溶解し、(1)、(2)、(9)、(15)、(17)をホモミキサーで乳化し、(乳化パーツ)を作成する。(10)、(12)、(13)、(16)を90℃で攪拌溶解し、急冷することで透明なワックス微細分散物を作成し、(乳化パーツ)を攪拌混合し、70℃に加温した(3)、(4)、(6)、(14)を混合し、80℃に加温した(7)と(8)を混合し、原液を得る。液化天然ガスを噴射剤としてこの原液を缶に充填して泡状ヘアワックスを得た。
配合成分 配合量(質量%)
(1)エタノール 残余
(2)POE(25)フィトステリル 1.0
(3)2,4-ビス-[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}-
フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン 0.5
(4)N-メタクロイルオキシエチルN-ジメチルアンモニウム
α-N-メチルカルボシキベタイン・メタクリル酸アルキル
エステル共重合体 5.0
(5)酢酸ビニル.ビニルピロリドン共重合体(P.V.P./VA-S630)5.0
(1)~(5)を混合し、液化天然ガスを噴射剤としてスプレー缶に充填してヘアスプレーを得た。
(1)実施例A-2(頭髪洗浄料)
下記表4に示す配合処方によってヘアコンディショナーを調製した。
下記表5および表6に示す配合処方によってヘアウォーターを調製した。
配合成分 配合量(質量%)
(1)塩化ベヘニルトリメチルアンモニウム 2.0
(2)セトステアリルアルコール(C16/C18=7:3) 3.0
(3)水添ナタネ油アルコール 3.0
(4)イソプレングリコール 3.0
(5)POE(30)POP(10)フィトステロール 0.5
(6)2,4,6-トリス[4-(2-エチルヘキシルオキシカルボニル)
アニリノ]-1,3,5-トリアジン 0.05
(7)クエン酸 0.3
(8)クエン酸ナトリウム 0.08
(9)フェノキシエタノール 0.3
(10)高重合メチルポリシロキサン 1.5
(11)イソステアリン酸 0.3
(12)精製水 残余
(13)香料 適量
表4のヘアシャンプーと同じ。
配合成分 配合量(質量%)
(1)ジメチルポリシロキサン 15.0
(2)ポリ(オキシエチレン・オキシプロピレン)メチル
ポリシロキサン共重合体 0.1
(3)POEメチルポリシロキサン共重合体 0.2
(4)高重合ジメチルシロキサン・メチル(アミノプロピル)
シロキサン共重合体 0.5
(5)高重合ジメチルポリシロキサン 1.0
(6)香料 適量
(7)エタノール 10.0
(8)プロピレングリコール 5.0
(9)エデト酸3ナトリウム 適量
(10)キサンタンガム 0.1
(11)酢酸ビニル・ビニルピロリドン共重合体 0.5
(12)アクリル酸・メタクリル酸アルキル共重合体 0.2
(13)カルボキシビニルポリマー 0.4
(14)精製水 残余
(15)POE(25)POP(5)フィトステリル 0.5
(16)2,4-ビス-[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}-
フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン 0.1
(17)2-アミノ-2-メチル-1-プロパノール 適量
(7)~(14)を混合して均一としたものに、(15)、(16)を80℃で溶融混合したものを調製して添加する。その後、(1)~(6)を混合した油相を添加して乳化し、(17)を加え中和し、ヘアトリートメントを調製した。
配合成分 配合量(質量%)
(1)流動パラフィン 10.0
(2)マイクロクリスタリンワックス 5.0
(3)プロピレングリコール 10.0
(4)POE(30)POP(7)フィトステリル 0.8
(5)2,4-ビス-[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}-
フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン 0.1
(6)カルナウバロウ 5.0
(7)イソステアリン酸 1.0
(8)ステアリン酸 2.0
(9)テトラ2-エチルヘキサン酸ペンタエリスリット 3.0
(10)イソステアリン酸POEグリセリル 2.0
(11)自己乳化型モノステアリン酸グリセリン 2.0
(12)無水ケイ酸 1.0
(13)トリエタノールアミン 0.3
(14)カルボキシビニルポリマー 0.2
(15)パラオキシ安息香酸エステル 適量
(16)エデト酸3ナトリウム 適量
(17)精製水 残余
(17)に(3)、(14)~(16)を溶解させたものを(水相)とする。(1)、(2)、(6)~(11)を90℃で溶解させたものを(油相)とする。水相に(12)を攪拌して投入し、80℃に加温する。これに(油相)を攪拌しながら投入し、ホモミキサーを用いて乳化し、(13)で中和をする。その後、80℃で溶解した(4)、(5)を攪拌混合し、脱気、冷却をして目的とするヘアワックスを得た。
配合成分 配合量(質量%)
(1)揮発性イソパラフィン 0.5
(2)エタノール 10.0
(3)POE(25)POP(5)フィトステリル 0.5
(4)2,4,6-トリス[4-(2-エチルヘキシルオキシカルボニル)
アニリノ]-1,3,5-トリアジン 0.2
(5)POE硬化ヒマシ油 0.5
(6)POE・POPデシルエーテル 0.5
(7)ビワ葉エキス 0.1
(8)N-メタクロイルオキシエチルN-ジメチルアンモニウム
α-N-メチルカルボシキベタイン・メタクリル酸ブチル
エステル共重合体 5.0
(9)精製水 残余
原液/噴射剤=90/10
(1)~(9)を混合し、液化天然ガスを噴射剤として缶に充填して泡状整髪料を得た。
配合成分 配合量(質量%)
(1)ポリオキシエチレン・メチルポリシロキサン共重合体 0.5
(2)エタノール 20.0
(3)グリセリン 10.0
(4)ジプロピレングリコール 1.0
(5)ヒドロキシプロピルメチルセルロース 0.1
(6)カラギーナン 0.1
(7)カルボキシビニルポリマー 0.6
(8)酢酸ビニル・ビニルピロリドン共重合体 5.0
(9)(メタクリロイルオキシエチルカルボキシベタイン/
メタクリル酸アルキル)コポリマー 2.0
(10)POE(25)POP(5)フィトステリル 0.5
(11)2,4-ビス-[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}-
フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン 0.1
(12)精製水 残余
(13)水酸化ナトリウム 適量
(9)と(10)を80℃で溶解し、(12)に投入し、(1)~(7)を溶解し、(13)で中和し、(8)と(9)を混合させることで、目的となるヘアスタイリングジェルを得た。
配合成分 配合量(質量%)
(1)ジメチルポリシロキサン 1.0
(2)エタノール 5.0
(3)ステアリルアルコール 0.1
(4)ベヘニルアルコール 0.2
(5)グリセリン 2.0
(6)ジプロピレングリコール 1.0
(7)1,3-ブチレングリコール 1.0
(8)塩化アルキルトリメチルアンモニウム(77%) 0.5
(9)ビニルピロリドン・N N-ジメチルアミノエチル
メタクリル酸共重合体 2.5
(10)パラオキシ安息香酸エステル 適量
(11)精製水 残余
(12)香料 適量
(13)POE(25)POP(5)フィトステリル 0.5
(14)2,4-ビス-[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}-
フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン 0.1
(1)、(3)、(4)、(6)、(7)、(8)、(12)及び(11)の一部を80℃で加温溶解し、高圧乳化機で乳化した後、(2)、(5)、(9)、(10)、及び、残りの(11)を溶解し、80℃に加温した(13)と(14)を混合し、霧状のディスペンサー容器に充填し、目的とする霧状スプレーを得た。
Claims (6)
- トリアジン基を有する紫外線吸収剤に対するポリオキシ低級アルキレン付加化合物(I)の配合比が、質量比で1以上である、請求項1に記載の毛髪化粧料。
- ポリオキシ低級アルキレン付加化合物(I)におけるフィトステロール残基又はフィトスタノール残基Rが、シトステロール残基、カンペステロール残基、スチグマステロール残基、ブラッシカステロール(brassicasterol)残基、アベナステロール(avenasterol)残基
、エルゴステロール残基、シトスタノール残基、カンペスタノール残基、スチグマスタノール残基、ブラッシカスタノール(brassicastanol)残基、アベナスタノール(avenastanol)残基、及び、エルゴスタノール残基、からなる群から選ばれる1種又は2種以上である、請求項1又は2に記載の毛髪化粧料。 - 毛髪化粧料が含水組成物である、請求項1~3のいずれかに記載の毛髪化粧料。
- 毛髪化粧料が頭髪洗浄料である、請求項1~4のいずれかに記載の毛髪化粧料。
- 毛髪化粧料が毛髪処理剤である、請求項1~4のいずれかに記載の毛髪化粧料。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09766717A EP2305207B1 (en) | 2008-06-20 | 2009-06-19 | Hair cosmetic |
US12/999,767 US8580235B2 (en) | 2008-06-20 | 2009-06-19 | Hair cosmetic |
CN2009801165329A CN102014860B (zh) | 2008-06-20 | 2009-06-19 | 毛发化妆料 |
JP2009527642A JP4468484B2 (ja) | 2008-06-20 | 2009-06-19 | 毛髪化粧料 |
KR1020107026508A KR101052439B1 (ko) | 2008-06-20 | 2009-06-19 | 모발 화장료 |
HK11106308.1A HK1152233A1 (en) | 2008-06-20 | 2011-06-21 | Hair cosmetic |
Applications Claiming Priority (4)
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JP2008-162424 | 2008-06-20 | ||
JP2008162424 | 2008-06-20 | ||
JP2008182088 | 2008-07-11 | ||
JP2008-182088 | 2008-07-11 |
Publications (1)
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WO2009154269A1 true WO2009154269A1 (ja) | 2009-12-23 |
Family
ID=41434181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2009/061190 WO2009154269A1 (ja) | 2008-06-20 | 2009-06-19 | 毛髪化粧料 |
Country Status (8)
Country | Link |
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US (1) | US8580235B2 (ja) |
EP (1) | EP2305207B1 (ja) |
JP (1) | JP4468484B2 (ja) |
KR (1) | KR101052439B1 (ja) |
CN (1) | CN102014860B (ja) |
HK (1) | HK1152233A1 (ja) |
TW (1) | TWI398267B (ja) |
WO (1) | WO2009154269A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017072397A (ja) * | 2015-10-05 | 2017-04-13 | 株式会社 資生堂 | 毛髪ケラチンフィルムを用いた化粧料の機能性評価方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101868223B (zh) * | 2007-12-27 | 2016-02-17 | 株式会社资生堂 | 可用作外用组合物的含水组合物 |
CN102014860B (zh) | 2008-06-20 | 2013-07-10 | 株式会社资生堂 | 毛发化妆料 |
EP2308512A4 (en) * | 2008-07-02 | 2012-08-29 | Shiseido Co Ltd | WATER-CONTAINING COMPOSITION |
WO2011125713A1 (ja) * | 2010-04-06 | 2011-10-13 | ライオン株式会社 | 毛髪化粧料 |
KR102033023B1 (ko) * | 2016-03-25 | 2019-10-16 | 가부시키가이샤 만다무 | 정발제 조성물 |
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CN102014860B (zh) | 2008-06-20 | 2013-07-10 | 株式会社资生堂 | 毛发化妆料 |
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2009
- 2009-06-19 CN CN2009801165329A patent/CN102014860B/zh active Active
- 2009-06-19 JP JP2009527642A patent/JP4468484B2/ja active Active
- 2009-06-19 TW TW098120700A patent/TWI398267B/zh active
- 2009-06-19 KR KR1020107026508A patent/KR101052439B1/ko active IP Right Grant
- 2009-06-19 US US12/999,767 patent/US8580235B2/en active Active
- 2009-06-19 WO PCT/JP2009/061190 patent/WO2009154269A1/ja active Application Filing
- 2009-06-19 EP EP09766717A patent/EP2305207B1/en not_active Not-in-force
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2011
- 2011-06-21 HK HK11106308.1A patent/HK1152233A1/xx not_active IP Right Cessation
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JPWO2009154269A1 (ja) | 2011-12-01 |
EP2305207A1 (en) | 2011-04-06 |
KR101052439B1 (ko) | 2011-07-29 |
CN102014860B (zh) | 2013-07-10 |
US8580235B2 (en) | 2013-11-12 |
TW201002356A (en) | 2010-01-16 |
KR20100133021A (ko) | 2010-12-20 |
HK1152233A1 (en) | 2012-02-24 |
EP2305207A4 (en) | 2011-08-03 |
TWI398267B (zh) | 2013-06-11 |
JP4468484B2 (ja) | 2010-05-26 |
CN102014860A (zh) | 2011-04-13 |
US20110110877A1 (en) | 2011-05-12 |
EP2305207B1 (en) | 2012-08-29 |
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