WO2009145300A1 - 皮膚外用剤 - Google Patents
皮膚外用剤 Download PDFInfo
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- WO2009145300A1 WO2009145300A1 PCT/JP2009/059870 JP2009059870W WO2009145300A1 WO 2009145300 A1 WO2009145300 A1 WO 2009145300A1 JP 2009059870 W JP2009059870 W JP 2009059870W WO 2009145300 A1 WO2009145300 A1 WO 2009145300A1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0212—Face masks
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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
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/12—Face or body powders for grooming, adorning or absorbing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Definitions
- the present invention relates to an external preparation for skin. More specifically, the present invention relates to a skin external preparation containing alkylresorcinols, which is excellent in temperature stability (particularly high temperature stability) and light stability.
- Alkylresorcinols are known to have a melanin production-inhibiting action and an antibacterial action, and are contained in cosmetics for the purpose of whitening and antibacterial purposes (see, for example, Patent Documents 1 and 2).
- L-ascorbic acid and L-ascorbic acid derivatives are also known as substances having a whitening effect.
- Alkylresorcinols and L-ascorbic acids both have a problem that they tend to cause discoloration due to temperature and light. However, until now, there are sufficient techniques for effectively suppressing discoloration of alkylresorcinols and L-ascorbic acids. There was no consideration.
- An object of the present invention is to provide a skin external preparation containing alkylresorcinols and L-ascorbic acids and having excellent temperature stability (particularly high temperature stability) and light stability.
- the present inventors have conducted extensive research. As a result, when only one of the alkylresorcinos and L-ascorbic acids is blended, the discoloration occurs due to temperature or light.
- the present invention comprises (a) 4-isobutylresorcinol or a salt thereof in an amount of 0.01 to 5% by mass, and (b) L-ascorbic acid or a salt thereof, 3-O-alkyl-L-ascorbic acid or a salt thereof.
- the present invention relates to a skin external preparation containing 0.01 to 5% by mass of one or more selected from among them.
- component (b) is 3-O-alkyl-L-ascorbic acid or a salt thereof is preferable.
- a skin external preparation containing an alkylresorcinol and an L-ascorbic acid derivative which is excellent in temperature stability (particularly high temperature stability) and light stability, is provided.
- POE represents polyoxyethylene
- POP represents polyoxypropylene
- the 4-isobutylresorcinol or a salt thereof as the component (a) used in the present invention is a compound represented by the following formula (I) or a salt thereof.
- the salt of 4-isobutylresorcinol represented by the above formula (I) is not particularly limited.
- alkali metal salts such as sodium salt, potassium salt and lithium salt, alkaline earth metals such as magnesium salt and calcium salt are used.
- metal salts ammonium salts, amino acid salts and the like can be mentioned. However, it is not limited to these examples.
- the blending amount of the component (a) is 0.01 to 5% by mass, preferably 0.1 to 3% by mass, more preferably 0.1 to 1% by mass in the external preparation for skin of the present invention. If the blending amount is less than 0.01% by mass, whitening effect, antibacterial effect and the like are poor, while blending exceeding 5% by mass is not preferable from the viewpoint of skin irritation.
- the component (b) used in the present invention is one or more selected from L-ascorbic acid or a salt thereof, 3-O-alkyl-L-ascorbic acid or a salt thereof.
- 3-O-alkyl-L-ascorbic acid or salts thereof include, for example, 3-O-methyl-L-ascorbic acid, 3-O-ethyl-L-ascorbic acid, 3-On-propyl-L- Ascorbic acid, 3-O-isopropyl-L-ascorbic acid, 3-On-butyl-L-ascorbic acid, 3-O-isobutyl-L-ascorbic acid, 3-O-tert-butyl-L-ascorbic acid 3-On-pentyl-L-ascorbic acid, 3-On-hexyl-L-ascorbic acid, 3-On-heptyl-L-ascorbic acid, 3-On-octyl-L- Examples thereof include 3-O-alkyl ethers
- the salt is not particularly limited, but examples include alkali metal salts such as sodium salt, potassium salt and lithium salt, alkaline earth metal salts such as magnesium salt and calcium salt, ammonium salt, amino acid salt and the like. It is done. However, it is not limited to these examples.
- 3-O-alkyl-L-ascorbic acid or a salt thereof particularly 3-O—C 1-6 alkyl-L-ascorbic acid or a salt thereof is most preferred.
- the blending amount of the component (b) is 0.01 to 5% by mass, preferably 0.05 to 3% by mass, particularly 0.1 to 3% by mass in the external preparation for skin of the present invention. If the blending amount is less than 0.01% by mass, the contribution of temperature stability is poor, while blending exceeding 5% by mass is not preferable from the viewpoint of skin irritation.
- the skin external preparation of the present invention combines the above components (a) and (b) to effectively suppress discoloration of both the components (a) and (b) (temperature stability (high temperature stability)). ) And particularly excellent in the effect of suppressing discoloration due to sunlight or xenon.
- Examples of the compound having a sterol skeleton as component (c-1) include compounds obtained by addition polymerization of ethylene oxide (EO), propylene oxide (PO), etc. to phytosterols, phytostanols, cholestanols, cholesteryl ethers, etc. Is mentioned. These compounds can be represented by the following formula (IV).
- R 5 represents any one of a phytosterol residue, a phytostanol residue, a cholestanol residue, and a cholesteryl ether residue
- s represents a number from 0 to 100
- t represents a number from 5 to 100 Indicates.
- the compound having a cholesterol skeleton include, for example, polyoxyethylene glycol phytosterols such as POE (5) phytosterol, POE (10) phytosterol, POE (20) phytosterol, POE (25) phytosterol, POE (30) phytosterol and the like.
- polyoxyethylene glycol phytosterols such as POE (5) phytosterol, POE (10) phytosterol, POE (20) phytosterol, POE (25) phytosterol, POE (30) phytosterol and the like.
- Polyoxyethylene phytostanols such as POE (20) phytostanol, POE (25) phytostanol and POE (30) phytostanol; POE (20) cholestanol, POE (25) cholestanol, POE (30) Polyoxyethylene cholestanols such as stanol; POE (5) cholesteryl ether, POE (10) cholesteryl ether, POE (15) cholesteryl ether, POE (20) cholesteryl ether Ether, POE (24) cholesteryl ether, POE (30) such as polyoxyethylene cholesteryl ethers cholesteryl ether.
- POE (20) phytosterol, POE (30) phytosterol, POE (30) cholestanol and the like are preferable, and POE (30) phytosterol is particularly preferable.
- the vitamin E derivative as the component (c-2) is not particularly limited, but for example, a compound represented by the following formula (V) or (VI) is preferably used.
- each substituent has the following meaning.
- EO represents an ethylene oxide group
- PO represents a propylene oxide group
- BO represents a butylene oxide group.
- R 6 , R 7 and R 8 each independently represent a hydrogen atom or a methyl group.
- Starting vitamin E is ⁇ - tocopherol );
- R 6 represents a hydrogen atom,
- R 7 and R 8 represent a methyl group (7,8-dimethyl form, when the starting vitamin E is ⁇ -tocopherol), or R 6 and R 7 represent a hydrogen atom, and R 8 represents a methyl group
- R 9 is a hydrogen atom, an alkanoyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an SO 3 H group, a P (O) (OH) 2 group, a CH 2 COOH group or COCH 2 CH ( SO 3 H) COOH group.
- the alkanoyl group having 1 to 6 carbon atoms may be linear or branched, and specific examples include an acetyl group, a propanoyl group, a butyryl group, an isobutyryl group, a pivaloyl group, and the like.
- a propanoyl group, a pivaloyl group and the like are preferable, and an acetyl group is particularly preferable from the viewpoint of synthesis.
- the alkyl group having 1 to 6 carbon atoms may be linear or branched, and specifically includes, for example, methyl group, ethyl group, propyl group, butyl group, isobutyl group, t-butyl group, pentyl group And a hexyl group.
- a methyl group, an ethyl group, a propyl group, a butyl group and the like are preferable, and a methyl group and an ethyl group are particularly preferable from the viewpoint of synthesis.
- the SO 3 H group, P (O) (OH) 2 group, CH 2 COOH group or COCH 2 CH (SO 3 H) COOH group can be combined with a base to form a salt.
- the base is not particularly limited as long as it has low toxicity and does not affect the antioxidant activity and moisturizing property of the vitamin E derivative represented by the above formula (V) or (VI).
- salts include alkali metal salts such as sodium salt, potassium salt and lithium salt; alkaline earth metal salts such as calcium salt and magnesium salt, aluminum salt, iron salt, zinc salt, copper salt and nickel salt Metal salts such as cobalt salts; Inorganic salts such as ammonium salts; t-octylamine salts, dibenzylamine salts, morpholine salts, glucosamine salts, phenylglycine alkyl ester salts, ethylenediamine salts, N-methylglucamine salts, guanidine salts , Diethylamine salt, triethylamine salt, dicyclohexylamine salt, N, N′-dibenzylethylenediamine salt, chloroprocaine salt, procaine salt, diethanolamine salt, N-benzyl-phenethylamine salt, piperazine salt, tetramethylammonium salt, tris (hydroxymethyl) )amino
- alkali metal salts, alkaline earth metal salts, ammonium salts and the like are preferable, and sodium salts, potassium salts, 1/2 magnesium salts, 1/2 calcium salts, ammonium salts, and the like are more preferable.
- K and y each represent a number of 0 to 30, preferably 0 to 25, particularly preferably 0 to 20 (however, k and y are not 0 at the same time).
- x represents a number of 1 to 30, preferably 1 to 10, and particularly preferably 1 to 5.
- Particularly preferred combinations of k, x, and y include those in which k and y are each 0 to 20 (however, k and y are not 0 simultaneously) and x is 1 to 5.
- the component (c-3) is a compound represented by the following formula (II).
- R 2 represents a linear or branched alkyl group or alkenyl group having 12 to 22 carbon atoms.
- n a number of 0 or 1.
- q represents an integer of 1 to 3
- R 4 represents a hydrogen atom or an aliphatic acyl group having 12 to 22 carbon atoms, m and p each independently represents an integer of 0 to 40, and m + p ⁇ 5.
- Preferred examples of the compound represented by the above formula (II) include polyglycerin fatty acid ester, polyoxybutene polyglycerin alkyl ether, and sucrose fatty acid ester.
- Examples of the polyglycerin part of the polyglycerin fatty acid ester are preferably glycerin pentamers to 20-mers.
- Examples of the fatty acid part include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and behenic acid.
- the aliphatic acyl group having 12 to 22 carbon atoms of R 4 is preferably a liloyl group, myristoyl group, palmitoyl group, stearoyl group, oleoyl group, linoloyl group or the like.
- decaglycerin monolaurate, decaglycerin monooleate, decaglycerin monostearate and the like can be preferably exemplified as commercially available products.
- polyoxybutene polyglycerin alkyl ethers are commercially available and can be used. Particularly preferred commercially available products include polyoxybutene (13) polyglyceryl (14) stearyl ether (“High Glyol S-26”; manufactured by Nippon Surfactant Co., Ltd.).
- sucrose monofatty acid esters are more preferred, and examples of the fatty acid moiety include lauric acid, palmitic acid, stearic acid, and oleic acid. That is, in the formula (II), R 3 is sucrose as a sugar residue, and R 2 is preferably a lauryl group, a myristyl group, a palmityl group, a stearyl group, an oleyl group, or the like.
- Specifically preferred sucrose monofatty acid esters are sucrose monolaurate, sucrose monostearate and the like.
- Examples of the compound having a sorbitan skeleton as the component (c-4) include sorbitan fatty acid esters and polyoxyethylene sorbitan fatty acid esters.
- the fatty acids constituting such esters include myristic acid, palmitic acid, and isostearic acid. , Stearic acid, oleic acid and the like can be suitably exemplified, and stearic acid is particularly preferable from the viewpoint of improving stability.
- the added mole number of polyoxyethylene is preferably 5 to 40, more preferably 10 to 30.
- the blending amount is preferably 0.01 to 7% by mass, more preferably 0.05 to 5% by mass, particularly 0.1% in the external preparation for skin of the present invention. To 3% by mass.
- the blending amount is less than 0.01% by mass, it is difficult to prepare the skin external preparation of the present invention as a transparent lotion, and it becomes difficult to prepare a transparent system, while when it exceeds 7% by mass, the usability (increase in stickiness) It is not preferable in terms of irritation.
- the external preparation for skin of the present invention is prepared by a conventional method using the above components as a base.
- the external preparation for skin of the present invention is not limited to the effects of the present invention, and other components that are usually used for external preparations for skin, such as powder components, liquid fats, solid fats, waxes, Hydrocarbon oil, higher fatty acid, higher alcohol, synthetic ester oil, silicone oil, anionic surfactant, cationic surfactant, amphoteric surfactant, nonionic surfactant, humectant, water-soluble polymer, film agent, ultraviolet ray Absorbers, sequestering agents, lower alcohols, polyhydric alcohols, sugars, amino acids, organic amines, polymer emulsions, pH adjusters, skin nutrients, vitamins, antioxidants, antioxidant aids, fragrances, water, etc. Can be appropriately blended as necessary. Specific ingredients that can be blended are listed below, but are not limited to these examples.
- the powder component examples include inorganic powders (for example, talc, kaolin, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, saucite, biotite, permiculite, magnesium carbonate, calcium carbonate, silicic acid.
- inorganic powders for example, talc, kaolin, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, saucite, biotite, permiculite, magnesium carbonate, calcium carbonate, silicic acid.
- Red No. 104 Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Green No. 3 and Blue No. 1
- natural pigments for example, chlorophyll, ⁇ -carotene, etc.
- liquid oils examples include avocado oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, southern castor oil, castor oil, linseed oil , Safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, cinnagiri oil, Japanese kiri oil, jojoba oil, germ oil, triglycerin and the like.
- solid fat examples include cacao butter, palm oil, horse fat, hydrogenated palm oil, palm oil, beef tallow, sheep fat, hydrogenated beef tallow, palm kernel oil, pork fat, beef bone fat, owl kernel oil, hydrogenated oil, cattle Leg fats, moles, hydrogenated castor oil and the like.
- waxes examples include beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, ibota wax, whale wax, montan wax, nuka wax, lanolin, kapok wax, lanolin acetate, liquid lanolin, sugar cane wax, lanolin fatty acid isopropyl, hexyl laurate, and reduced lanolin.
- hydrocarbon oil examples include liquid paraffin, ozokerite, squalane, pristane, paraffin, ceresin, squalene, petrolatum, and microcrystalline wax.
- higher fatty acid examples include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, toluic acid, isostearic acid, linoleic acid, linolenic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid ( DHA) and the like.
- higher alcohols examples include linear alcohols (eg, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol); branched chain alcohols (eg, monostearyl glycerin ether (batyl alcohol) ), 2-decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyl decanol, isostearyl alcohol, octyldodecanol, etc.).
- linear alcohols eg, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol
- branched chain alcohols eg, monostearyl glycerin ether (batyl alcohol)
- 2-decyltetradecinol lanolin alcohol
- cholesterol phytosterol
- hexyl decanol isosteary
- Synthetic ester oils include isopropyl myristate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyl decyl dimethyloctanoate, cetyl lactate, myristyl lactate Lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, ethylene glycol di-2-ethylhexanoate, dipentaerythritol fatty acid ester, N-alkyl glycol monoisostearate, neopentyl glycol dicaprate, apple Acid diisostearyl, di-2-heptylundecanoic acid glycerin, tri-2-ethylhexanoic acid
- silicone oil examples include linear polysiloxanes (for example, dimethylpolysiloxane, methylphenylpolysiloxane, diphenylpolysiloxane, etc.); cyclic polysiloxanes (for example, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexyl).
- silicone resins that form a three-dimensional network structure various modified polysiloxanes (amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane, fluorine-modified polysiloxane, etc.) It is done.
- Anionic surfactants include, for example, fatty acid soaps (eg, sodium laurate, sodium palmitate, etc.); higher alkyl sulfates (eg, sodium lauryl sulfate, potassium lauryl sulfate, etc.); alkyl ether sulfates (eg, POE-lauryl sulfate triethanolamine, POE-sodium lauryl sulfate, etc.); N-acyl sarcosine acid (eg, sodium lauroyl sarcosine, etc.); higher fatty acid amide sulfonate (eg, sodium N-myristoyl-N-methyl taurate, palm Oil fatty acid methyl tauride sodium, lauryl methyl tauride sodium, etc.); phosphate ester salts (POE-oleyl ether sodium phosphate, POE-stearyl ether phosphate, etc.); sulfosuccinate ( For example, sodium di-2-eth
- Examples of the cationic surfactant include alkyltrimethylammonium salts (eg, stearyltrimethylammonium chloride, lauryltrimethylammonium chloride, etc.); alkylpyridinium salts (eg, cetylpyridinium chloride, etc.); distearyldimethylammonium dialkyldimethylammonium chloride; Poly (N, N′-dimethyl-3,5-methylenepiperidinium chloride); alkyl quaternary ammonium salt; alkyldimethylbenzylammonium salt; alkylisoquinolinium salt; dialkyl morpholinium salt; POE-alkylamine; Examples include alkylamine salts; polyamine fatty acid derivatives; amyl alcohol fatty acid derivatives; benzalkonium chloride; benzethonium chloride and the like.
- alkyltrimethylammonium salts eg, stearyltrimethylammonium chloride, lauryltrimethyl
- amphoteric surfactants examples include imidazoline-based amphoteric surfactants (eg, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide). Side-1-carboxyethyloxy disodium salt, etc.); betaine surfactants (for example, 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, alkylbetaine, amide betaine) , Sulfobetaine, etc.).
- imidazoline-based amphoteric surfactants eg, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide).
- lipophilic nonionic surfactant examples include propylene glycol fatty acid esters (for example, propylene glycol monostearate); hardened castor oil derivatives, and the like.
- hydrophilic nonionic surfactant examples include POE sorbite fatty acid esters (for example, POE-sorbite monolaurate, POE-sorbite monooleate, POE-sorbite pentaoleate, POE-sorbite monostearate, etc.); POE-glycerin fatty acid esters (for example, POE-glycerin monostearate, POE-glycerin monoisostearate, POE-monooleate such as POE-glycerin triisostearate, etc.); POE-fatty acid esters (for example, POE-distearate) , POE-monodiolate, ethylene glycol distearate, etc.); POE-alkyl ethers (for example, POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE- Henyl ether, POE-2-octyldodecyl ether,
- humectant examples include polyethylene glycol, propylene glycol, glycerin, 1,3-butylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate Sodium lactate, bile salt, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin (EO) PO adduct, Izayoi rose extract, yarrow extract, merirot extract and the like.
- EO diglycerin
- natural water-soluble polymers include plant-based polymers (for example, gum arabic, gum tragacanth, galactan, guar gum, carob gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), alge colloid (guckweed extract), starch (Rice, corn, potato, wheat), glycyrrhizic acid); microbial polymers (eg, xanthan gum, dextran, succinoglucan, bullulan, etc.); animal polymers (eg, collagen, casein, albumin, gelatin, etc.), etc. Is mentioned.
- plant-based polymers for example, gum arabic, gum tragacanth, galactan, guar gum, carob gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), alge colloid (guckweed extract), starch (Rice, corn, potato, wheat), glycyrrhizic acid);
- Semi-synthetic water-soluble polymers include, for example, starch polymers (eg, carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose polymers (methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate) Hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder and the like); alginic acid polymers (for example, sodium alginate, propylene glycol alginate, etc.) and the like.
- starch polymers eg, carboxymethyl starch, methylhydroxypropyl starch, etc.
- cellulose polymers methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate Hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder and the like
- alginic acid polymers for example, sodium
- Synthetic water-soluble polymers include, for example, vinyl polymers (eg, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer); polyoxyethylene polymers (eg, polyethylene glycol 20,000, 40). , 000, 60,000 polyoxyethylene polyoxypropylene copolymer, etc.); acrylic polymers (for example, sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers, and the like.
- vinyl polymers eg, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer
- polyoxyethylene polymers eg, polyethylene glycol 20,000, 40. , 000, 60,000 polyoxyethylene polyoxypropylene copolymer, etc.
- acrylic polymers for example, sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.
- polyethyleneimine
- inorganic water-soluble polymers examples include bentonite, AlMg silicate (beegum), laponite, hectorite, and silicic anhydride.
- ultraviolet absorber examples include benzoic acid-based ultraviolet absorbers (for example, paraaminobenzoic acid (hereinafter abbreviated as PABA), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester, N, N-diethoxy PABA ethyl ester.
- PABA paraaminobenzoic acid
- PABA monoglycerin ester N, N-dipropoxy PABA ethyl ester
- N, N-diethoxy PABA ethyl ester examples include benzoic acid-based ultraviolet absorbers (for example, paraaminobenzoic acid (hereinafter abbreviated as PABA), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester, N, N-diethoxy PABA ethyl ester.
- PABA paraaminobenzoic acid
- Benzophenone ultraviolet absorbers for example, 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2 ', 4,4 '-Tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2 -Ethylhexyl-4'-phenyl-benzophenone-2-carboxylate, 2-hydroxy-4-n-octoxybenzophenone, 4-hydroxy-3-carboxybenzophenone, etc.); 3- (4'-methylbenzylidene) -d, l-camphor, 3-ben Redene-d, l-camphor; 2-phenyl-5-methylbenzoxazole; 2,2'-hydroxy-5-methylphenyl
- sequestering agent examples include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, and tetrasodium edetate.
- lower alcohols examples include ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol and the like.
- polyhydric alcohol examples include divalent alcohols (for example, ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, Pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, octylene glycol, etc.); trivalent alcohol (eg, glycerin, trimethylolpropane, etc.); tetravalent alcohol (eg, 1, 2, 6) Pentaerythritol, such as hexanetriol, etc .; pentavalent alcohol (eg, xylitol, etc.); hexavalent alcohol (eg, sorbitol, mannitol, etc.); polyhydric alcohol polymer (eg, diethylene glycol, dipropylene glycol, Ethylene glycol, polypropylene glycol, tetraethylene glycol,
- Monosaccharides include, for example, tricarbon sugars (eg, D-glyceryl aldehyde, dihydroxyacetone, etc.); tetracarbon sugars (eg, D-erythrose, D-erythrulose, D-treose, erythritol, etc.); pentose sugars (eg, L-arabinose, D-xylose, L-lyxose, D-arabinose, D-ribose, D-ribulose, D-xylulose, L-xylulose, etc .; hexose (eg, D-glucose, D-talose, D) -Bucicose, D-galactose, D-fructose, L-galactose, L-mannose, D-tagatose, etc.); pentose sugar (eg, aldheptose, heproose, etc.); octo
- Oligosaccharides include, for example, sucrose, guntianose, umbelliferose, lactose, planteose, isoliquinoses, ⁇ , ⁇ -trehalose, raffinose, lycnose, umbilicin, stachyose verbus courses, and the like.
- polysaccharide examples include cellulose, quince seed, chondroitin sulfate, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, tragacanth gum, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfate, guar gum, dextran, kerato sulfate. , Locust bingham, succinoglucan, caronic acid and the like.
- amino acids examples include neutral amino acids (eg, threonine, cysteine, etc.); basic amino acids (eg, hydroxylysine, etc.), and the like.
- amino acid derivatives include acyl sarcosine sodium (lauroyl sarcosine sodium), acyl glutamate, acyl ⁇ -alanine sodium, glutathione, pyrrolidone carboxylic acid and the like.
- organic amines examples include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1-propanol. Is mentioned.
- polymer emulsion examples include acrylic resin emulsion, polyethyl acrylate emulsion, acrylic resin liquid, polyacryl alkyl ester emulsion, polyvinyl acetate resin emulsion, natural rubber latex, and the like.
- vitamins examples include vitamins A, B1, B2, B6, C, E and derivatives thereof, pantothenic acid and derivatives thereof, biotin and the like.
- antioxidants examples include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters and the like.
- antioxidant assistant examples include phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, kephalin, hexametaphosphate, phytic acid, ethylenediaminetetraacetic acid and the like.
- ingredients that can be blended include, for example, preservatives (ethyl paraben, butyl paraben, etc.); anti-inflammatory agents (eg, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); whitening agents (for example, Extract, placenta extract, saxifrage extract, arbutin, etc.); various extracts (eg, buckwheat, auren, shikon, peonies, assembly, birch, sage, loquat, carrot, aloe, mallow), iris, grape, yokuinin, loofah, lily , Saffron, nematode, ginger, hypericum, onionis, garlic, red pepper, chimney, red snapper, seaweed, etc.), activator (for example, royal jelly, photosensitizer, cholesterol derivative, etc.); blood circulation promoter (
- the dosage form of the skin cosmetic of the present invention is arbitrary, and examples include a solubilization system, an emulsification system, a powder dispersion system, an oil-water two-layer system, and an oil-water-powder three-layer system. It is not limited to.
- the product form of the skin cosmetic of the present invention is also arbitrary, and can be used for facial skin cosmetics such as lotion, milky lotion, cream and pack, body skin cosmetics and aromatic skin cosmetics.
- the blending amount is expressed in mass% with respect to the system in which the component is blended.
- Example 1 Effect of 4-isobutylresorcinol to prevent discoloration and deodorization of ascorbic acid or its derivatives under sunlight irradiation (50 ° C.)
- 4-isobutylresorcinol prevents discoloration of ascorbic acids.
- samples 3 and 5 using 3-O-ethyl-L-ascorbic acid and L-ascorbic acid as L-ascorbic acids reduce color difference.
- Sample 3 using 3-O-ethyl-L-ascorbic acid has a color difference reduction rate of about 97% and a color difference of 0.091, which is almost completely 3-O-ethyl by 4-isobutylresorcinol. The discoloration of -L-ascorbic acid could be suppressed.
- Example 2 Significant discoloration prevention effect of 4-isobutylresorcinol in alkylresorcinols
- ⁇ E Color difference
- Samples 7 to 20 shown in Table 2 below were allowed to stand in a thermostat at 50 ° C. (light-shielding) for 2 weeks, and each sample returned to room temperature was measured for color difference ( ⁇ E) with a color difference meter (GretagMacbeth Color-Eye 7000A). A smaller color difference ( ⁇ E) indicates less discoloration.
- the transparency of each sample was measured using an integrating sphere spectrophotometer (“Color-Eye7000A”, manufactured by GretagMacbeth) to measure the L value (transparency as the L value approaches 100). The results are shown in Table 2.
- the external preparation for skin of the present invention contains alkylresorcinols and L-ascorbic acids, which have been conventionally considered to easily cause discoloration due to temperature and light, it has temperature stability (particularly high temperature stability), light Excellent stability.
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Abstract
Description
下記表1に示す試料1~6に対し日光(50MJ、50℃)を照射した。照射終了後、室温に戻した各試料を色差計(GretagMacbeth Color-Eye 7000A)で色差(ΔE)を測定した。色差(ΔE)が小さいほど変色が少ないことを示す。併せて、各試料の透明度を積分球分光光度計(「Color-Eye7000A」、GretagMacbeth社製)を用いて、L値(L値が100に近いほど透明)を測定した。結果を表1に示す。
下記表1に示す試料1~6に対し日光(50MJ、50℃)を照射した。照射終了後、室温に戻した各試料について専門パネラー(5名)がこれら試料の臭いの官能評価を行い、非常によい(5点)、よい(4点)、普通(3点)、悪い(2点)、非常に悪い(1点)、の5段階で評価した。評価結果は、5名の評価の平均値を求めて、以下の基準に従って表した。
(評価)
◎:5名の評価の平均値が4.0~5.0である
○:5名の評価の平均値が3.0~3.9である
△:5名の評価の平均値が2.0~2.9である
×:5名の評価の平均値が1.0~1.9である
試料1~2、試料3~4、試料5~6において、[{(4-イソブチルレゾルシノールを配合しない試料の色差(ΔE))-(4-イソブチルレゾルシノールを配合した試料の色差(ΔE))}/(4-イソブチルレゾルシノールを配合しない試料の色差(ΔE))]×100(%)として計算した。これにより、L-アスコルビン酸またはその誘導体に対する4-イソブチルレゾルシノールの変色防止効果がわかる。色差減少率(%)が100(%)に近いほど変色防止効果に優れる。結果を表1に示す。
[色差(ΔE)、L値]
下記表2に示す試料7~20を、50℃(遮光)の恒温槽に2週間放置後、室温に戻した各試料を色差計(GretagMacbeth Color-Eye 7000A)で色差(ΔE)を測定した。色差(ΔE)が小さいほど変色が少ないことを示す。併せて、各試料の透明度を積分球分光光度計(「Color-Eye7000A」、GretagMacbeth社製)を用いて、L値(L値が100に近いほど透明)を測定した。結果を表2に示す。
Claims (2)
- (a)4-イソブチルレゾルシノールまたはその塩を0.01~5質量%と、(b)L-アスコルビン酸またはその塩、3-O-アルキル-L-アスコルビン酸またはその塩の中から選ばれる1種または2種以上を0.01~5質量%含有する皮膚外用剤。
- (b)成分が3-O-アルキル-L-アスコルビン酸またはその塩である、請求項1記載の皮膚外用剤。
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/994,883 US8486997B2 (en) | 2008-05-29 | 2009-05-29 | External preparation for skin |
JP2010514552A JP5553411B2 (ja) | 2008-05-29 | 2009-05-29 | 皮膚外用剤 |
CN2009801197118A CN102046141B (zh) | 2008-05-29 | 2009-05-29 | 皮肤外用剂 |
RU2010154144/15A RU2529818C2 (ru) | 2008-05-29 | 2009-05-29 | Наружное средство для кожи |
ES09754808.5T ES2643830T3 (es) | 2008-05-29 | 2009-05-29 | Preparación externa para la piel |
EP09754808.5A EP2292208B1 (en) | 2008-05-29 | 2009-05-29 | External preparation for skin |
KR1020107028852A KR101455969B1 (ko) | 2008-05-29 | 2009-05-29 | 피부 외용제 |
AU2009252231A AU2009252231A1 (en) | 2008-05-29 | 2009-05-29 | External preparation for skin |
BRPI0912134A BRPI0912134B1 (pt) | 2008-05-29 | 2009-05-29 | preparação externa para pele |
HK11111270.5A HK1156867A1 (en) | 2008-05-29 | 2011-10-20 | External preparation for skin |
AU2016204668A AU2016204668B2 (en) | 2008-05-29 | 2016-07-06 | External preparation for skin |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008141738 | 2008-05-29 | ||
JP2008-141738 | 2008-05-29 |
Publications (1)
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WO2009145300A1 true WO2009145300A1 (ja) | 2009-12-03 |
Family
ID=41377169
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2009/059870 WO2009145300A1 (ja) | 2008-05-29 | 2009-05-29 | 皮膚外用剤 |
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Country | Link |
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US (1) | US8486997B2 (ja) |
EP (1) | EP2292208B1 (ja) |
JP (1) | JP5553411B2 (ja) |
KR (1) | KR101455969B1 (ja) |
CN (1) | CN102046141B (ja) |
AU (2) | AU2009252231A1 (ja) |
BR (1) | BRPI0912134B1 (ja) |
ES (1) | ES2643830T3 (ja) |
HK (1) | HK1156867A1 (ja) |
RU (1) | RU2529818C2 (ja) |
TW (1) | TWI414317B (ja) |
WO (1) | WO2009145300A1 (ja) |
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US8906432B2 (en) | 2009-10-02 | 2014-12-09 | Johnson & Johnson Consumer Companies, Inc. | Compositions comprising an NFκB-inhibitor and a non-retinoid collagen promoter |
WO2015190505A1 (ja) * | 2014-06-10 | 2015-12-17 | 味の素株式会社 | 3-o-アルキル-l-アスコルビン酸又はその塩を含有する化粧料組成物 |
US9370474B2 (en) | 2009-10-02 | 2016-06-21 | Johnson & Johnson Consumer Inc. | High-clarity aqueous concentrates of 4-hexylresorcinol |
US9375395B2 (en) | 2009-10-02 | 2016-06-28 | Johnson & Johnson Consumer Inc. | Compositions comprising an NFκB-inhibitor and a tropoelastin promoter |
JP2018140960A (ja) * | 2017-02-28 | 2018-09-13 | ロレアル | レゾルシノール又はその誘導体を含む組成物 |
US10307352B2 (en) | 2012-09-24 | 2019-06-04 | Johnson & Johnson Consumer Inc. | Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester |
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US20160136078A1 (en) * | 2012-11-30 | 2016-05-19 | Corum Inc. | Method for Stabilizing Ascorbic Acid Derivatives and the Application Thereof |
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US8906432B2 (en) | 2009-10-02 | 2014-12-09 | Johnson & Johnson Consumer Companies, Inc. | Compositions comprising an NFκB-inhibitor and a non-retinoid collagen promoter |
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US9370474B2 (en) | 2009-10-02 | 2016-06-21 | Johnson & Johnson Consumer Inc. | High-clarity aqueous concentrates of 4-hexylresorcinol |
US9375395B2 (en) | 2009-10-02 | 2016-06-28 | Johnson & Johnson Consumer Inc. | Compositions comprising an NFκB-inhibitor and a tropoelastin promoter |
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EP2292208A1 (en) | 2011-03-09 |
CN102046141A (zh) | 2011-05-04 |
AU2016204668B2 (en) | 2018-03-08 |
EP2292208B1 (en) | 2017-07-19 |
RU2529818C2 (ru) | 2014-09-27 |
KR101455969B1 (ko) | 2014-10-31 |
BRPI0912134B1 (pt) | 2017-01-17 |
JP5553411B2 (ja) | 2014-07-16 |
AU2009252231A1 (en) | 2009-12-03 |
RU2010154144A (ru) | 2012-07-10 |
TWI414317B (zh) | 2013-11-11 |
AU2016204668A1 (en) | 2016-08-04 |
JPWO2009145300A1 (ja) | 2011-10-13 |
BRPI0912134A2 (pt) | 2015-11-03 |
CN102046141B (zh) | 2013-02-13 |
KR20110013502A (ko) | 2011-02-09 |
ES2643830T3 (es) | 2017-11-24 |
EP2292208A4 (en) | 2015-04-08 |
HK1156867A1 (en) | 2012-06-22 |
TW201008591A (en) | 2010-03-01 |
US8486997B2 (en) | 2013-07-16 |
US20110213030A1 (en) | 2011-09-01 |
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