WO2019132070A1 - Produit cosmétique antivieillissement contenant un produit soluble nanoparticulaire obtenu par la solubilisation d'acide oléanolique faiblement soluble, et procédé de préparation de produits cosmétiques antivieillissement - Google Patents

Produit cosmétique antivieillissement contenant un produit soluble nanoparticulaire obtenu par la solubilisation d'acide oléanolique faiblement soluble, et procédé de préparation de produits cosmétiques antivieillissement Download PDF

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Publication number
WO2019132070A1
WO2019132070A1 PCT/KR2017/015677 KR2017015677W WO2019132070A1 WO 2019132070 A1 WO2019132070 A1 WO 2019132070A1 KR 2017015677 W KR2017015677 W KR 2017015677W WO 2019132070 A1 WO2019132070 A1 WO 2019132070A1
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Prior art keywords
oleanolic acid
mixture
acid
weight
parts
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PCT/KR2017/015677
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English (en)
Korean (ko)
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정한수
조선행
안주영
이용우
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정한수
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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
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • 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
    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof

Definitions

  • the present invention relates to a cosmetic for improving skin wrinkles. More specifically, the present invention relates to a cosmetic preparation for improving skin wrinkles, which comprises solubilizing and micellizing oleanolic acid as an insoluble polymer, This invention relates to an anti-aging cosmetic comprising nanoparticles useful for increasing solubility and improving skin permeability.
  • Skin aging occurs through two main processes.
  • the change that occurs with age without any special environmental factors is called intrinsic aging, and the change in appearance on the face, neck, and hands due to long exposure to environmental factors such as ultraviolet light It is called photo aging or extrinsic aging.
  • the main cause of the endogenous aging is the accumulation of damage to the constituents of the body due to reactive oxygen radicals produced in the metabolism of the body.
  • extrinsic aging is different in that harmful free radicals are produced by ultraviolet rays. Once active oxygen is produced, failure to effectively remove by various protective devices in the body results in a series of inflammatory reactions leading to skin damage, and typical damage to the skin is wrinkled skin.
  • retinol is widely known as a substance having a wrinkle-reducing effect in cosmetics, but it is vulnerable to heat or light, and it is photosensitive, so that a problem of making the skin more sensitive when exposed to sunlight is suggested.
  • oleanolic acid has been proposed as an alternative to retinol.
  • the oleanolic acid has poor solubility in a solvent such as water and solubilized in general cosmetics using water as a solvent There was a difficult problem,
  • Korean Patent Registration No. 10-1802963 relates to a cosmetic composition using a fermented extract, which comprises a fermented extract of a medicinal substance containing red ginseng and ginseng; Sustained fermentation extract; And a soybean fermentation extract.
  • a fermented extract which comprises a fermented extract of a medicinal substance containing red ginseng and ginseng; Sustained fermentation extract; And a soybean fermentation extract.
  • the cosmetic composition further comprises oleoanic acid as a skin pore filling agent.
  • the cosmetic composition according to the above-mentioned prior art can provide a skin-improving effect such as prevention of skin aging and alleviation of wrinkles by including a natural medicinal material, a fat and a fermented soybean extract as an active ingredient.
  • a natural medicinal material e.g., a hydroxybenzoic acid
  • a fat and a fermented soybean extract e.g., a hydroxybenzoic acid
  • the present invention relates to a cosmetic composition for improving the solubility of an insoluble oleanolic acid having the effect of improving skin wrinkles and containing nanoparticulate products containing micellized oleoanic acid Cosmetics, and the like.
  • the present invention has been made to solve the above-
  • the present invention relates to an anti-aging cosmetic composition
  • oleanolic acid and 1 to 30 parts by weight of a solubilizing agent are mixed with stirring to prepare a first mixture of oleanolic acid;
  • the cosmetic according to the present invention as described above can enhance the skin permeation effect of oleanolic acid having the effect of improving the wrinkles of the skin through the nanoparticulate product in which oleic acid is solubilized and micellized.
  • FIG. 1 shows the stability test results of nanoparticulate solubilizing insoluble oleoanic acid according to the first embodiment of the present invention.
  • FIG. 2 is an image showing a skin permeation test procedure of the nanoparticle useful solubilized with poorly soluble oleoanic acid according to the first embodiment of the present invention.
  • FIG. 3 is a graph showing the results of skin permeation test of nanoparticulate products solubilized with poorly soluble oleoanic acid according to the first embodiment of the present invention.
  • the nanoparticle-containing material has a particle size of 20 to 150 nm in order to improve permeability to the skin.
  • Oleanolic acid is known as a substance having an antioxidative effect.
  • it is a substance exhibiting an effect of improving skin wrinkles due to the constantly effective action.
  • Retinol which is known as a skin wrinkle-reducing substance, has a disadvantage in that it is unstable to heat or light and its effectiveness is reduced by half when it is contained as an effective substance in cosmetics.
  • oleanolic acid has been proposed as an alternative effective substance that can improve the disadvantages of retinol.
  • Oleanolic Acid is hardly soluble in water, which is a main component of cosmetics, and has a problem that it is difficult to permeate the skin because of its large particle size.
  • the present invention provides a method of preparing a solution of an oleanolic acid by mixing a solution aid and an amphiphilic polymer in the oleanolic acid so as to be able to react favorably in a soluble micelle form, Anionic acid was dissolved in distilled water to make cosmetics.
  • solubilizer serves as an adjuvant for both hydrophilic polymers which are dissolvers to micellize the oleoanic acid.
  • the dissolution aid may be any one or more of ethylene glycol, propylene glycol monocaprylate, tetraethylene glycol, polyethylene glycol, polypropylene glycol and polybutylene glycol, preferably ethylene glycol or propylene glycol And cocaprylate may be used.
  • the dissolution aid may be used in an amount of 1 to 30 parts by weight, preferably 2 to 10 parts by weight, based on 0.05 to 1 part by weight of the oleanolic acid. If the solubilizing agent is contained in an amount of less than 1 part by weight based on 1 part by weight of the oleanolic acid, the dispersion of the oleanolic acid is incomplete and the release of the oleoanic acid becomes difficult at the time of use of the cosmetic, When the amount is more than 30 parts by weight based on 1 part by weight, there is a problem that the stability of the oleanolic acid is insufficient and the reagent is wasted.
  • solubility of the oleanolic acid by the solubilizing aid it is possible to further use glycofurol, polysorbate, crmolpore, Solutol HS 15 and the like.
  • amphiphilic polymer plays a role of micelle formation and preferably triblock copolymers in the form of ⁇ polyethylene oxide (PEO) -polypropylene oxide (PPO) -polyethylene oxide (PEO)> More preferably, at least one of Poloxamer 184, Poloxamer 185, Poloxamer 188, Poloxamer 124, Poloxamer 237, Poloxamer 338 or Poloxamer 407 can be used.
  • PEO polyethylene oxide
  • PPO polypropylene oxide
  • PEO polyethylene oxide
  • Poloxamer 184 Poloxamer 185
  • Poloxamer 188 Poloxamer 124
  • Poloxamer 237 Poloxamer 338
  • Poloxamer 407 can be used.
  • the triblock copolymer is preferably contained in an amount of 1 to 30 parts by weight, more preferably 5 to 20 parts by weight, based on 0.01 to 1 part by weight of oleic acid. If the triblock copolymer is contained in an amount of less than 1 part by weight based on 0.01 to 1 part by weight of oleanolic acid, there is a problem that precipitation of oleanolic acid occurs, and when the amount of the triblock copolymer is 30 parts by weight per 1 part by weight of oleanolic acid There is a problem that the particle size is increased and the stability is lowered.
  • both of the above-mentioned biocompatible polymers have a high mixing ratio within the above-mentioned mixing ratio, so that the nanoparticle useful product is made into a gel-like form, and as the mixing ratio is lowered, the prepared nanoparticle-containing mule can be made into a liquid form.
  • the distilled water serves as a solvent for dissolving the oleanolic acid, the dissolution aid, and the biodegradable polymer.
  • the distilled water is preferably contained in an amount of 39 to 97.99 parts by weight based on 0.01 to 1 part by weight of oleic acid.
  • the distilled water contains less than 39 parts by weight of oleanolic acid based on 0.01 to 1 part by weight of the oleanolic acid, there is a problem that the oleanolic acid is not fully micellized.
  • 0.01 to 1 part by weight of oleanolic acid is used, There is a problem that the concentration of the produced nanoparticle useful substance may be excessively lowered.
  • the oleanolic acid, the solubilizing aid, the amphiphilic polymer, and the distilled water may be mixed together to form the nanoparticle useful product, but preferably the oleanolic acid and the dissolution aid
  • the oleanolic acid first mixture is added to the oleanolic acid first mixture and then the two ampholytic polymers are added to the oleanolic acid first mixture, and then the mixture is stirred under heating to prepare a second oleanolic acid mixture,
  • the second mixture of ricinic acid may be mixed with the distilled water to make the nanoparticle useful product.
  • the first oleanolic acid mixture is composed of an oleanolic acid and a solubilizing agent mixed with stirring, and the solubilizing agent is preferentially dispersed and mixed in oleic acid.
  • the dissolution aid when the dissolution aid is first dispersed in the oleanolic acid, the dissolution aid is first dissolved in the mixture of the oleanolic acid particles before the bilayer fibrillating polymer which mainly forms the micelle reacts with the oleinic acid, It is possible to obtain an effect of improving the micelle formation of oleanolic acid.
  • the oleanolic acid second mixture may be prepared by mixing the first oleanolic acid mixture with a biocompatible polymer.
  • the oleanolic acid contained in the first mixture of oleanolic acid may be heated to improve the reaction activity And is a constitution for increasing the solubilization of oleanolic acid having poor solubility.
  • the heating temperature for making the oleanolic acid second mixture is maintained at 30 to 80 ⁇ .
  • the heating temperature is less than 30 ° C, the reaction activity of oleanolic acid is somewhat insufficient, and if it exceeds 80 ° C, the oleanolic acid may be deteriorated.
  • the present invention relates to a method for producing an oleanolic acid, comprising: a first step of mixing 0.01 to 1 part by weight of oleanolic acid and 1 to 30 parts by weight of a solubilizing agent with stirring to prepare a first mixture of oleanolic acid; A second step of adding 1 to 30 parts by weight of an amphiphilic polymer to the oleanolic acid first mixture, followed by stirring and mixing under heating to prepare a second oleanolic acid mixture; A third step of adding 39 to 97.99 parts by weight of distilled water to the oleanolic acid second mixture, followed by stirring and mixing to form a nanoparticle useful product; And a fourth step of preparing a cosmetic product by mixing the nanoparticulate useful product with a carrier component contained in a known cosmetic product.
  • the method for manufacturing an anti-aging cosmetic product comprising the nanoparticulate product obtained by solubilizing the poorly soluble oleoanic acid .
  • the method of manufacturing a cosmetic product according to the present invention can produce a cosmetic product containing a nanoparticle useful product having a particle size of 20 to 150 nm in which the whitening improving active substance is encapsulated.
  • oleanolic acid and 1 to 30 parts by weight of a solubilizing agent are mixed with stirring to prepare a first mixture of oleanolic acid, and dissolution of poorly soluble oleoanic acid
  • auxiliary solubilizing agent is preferentially dispersed and mixed in the oleoanilic acid.
  • the first step is to weigh the oleanolic acid and the dissolution aid at the mixing ratio, and then mix with stirring using an agitator, and the stirring temperature can be treated at room temperature (15 to 25 ° C).
  • the second step 1 to 30 parts by weight of an amphiphilic polymer is added to the oleanolic acid first mixture, followed by stirring and mixing under heating to prepare a second oleanolic acid mixture, And solubilizing the oleanolic acid into the bi-hydrophilic polymer.
  • the stirring mixture of the first oleanolic acid mixture and the biodegradable polymer is preferably carried out in a warmed state for the purpose of solubilizing the oleanolic acid, and the heating temperature is preferably maintained at 30 to 80 ° C.
  • the third step 39 to 97.99 parts by weight of distilled water is added to the oleanolic acid mixture (2) and stirred to prepare a nanoparticle useful product.
  • the oleanolic acid solubilized in the second step is dissolved in a micelle- It is the process of making things.
  • the distilled water serves as a solvent for dissolving the oleanolic acid, the dissolution aid, and the biodegradable polymer.
  • the nanoparticle useful product is mixed with a carrier component contained in a known cosmetic product to produce a cosmetic product.
  • the nanoparticulate product prepared according to the present invention may be mixed with a known Mixing the carrier component and the titration at a mixing ratio to prepare a cosmetic product having various formulations.
  • the cosmetic according to the present invention can be used as an active ingredient of cosmetics which can be classified into kinds such as skin, toner, essence, emulsion, lotion, cream, face mist, cleansing or face pack emulsion and the like. That is, the cosmetics of the above kind may be classified according to the formulations, and may further comprise various kinds of carrier components for forming the respective formulations, using the cosmetic composition according to the present invention as an active ingredient.
  • the carrier component may be animal fiber, plant fiber, wax, paraffin, starch , Talc, a cellulose derivative, polyethylene glycol, silicon, bentonite, silica, talc or zinc oxide may be used.
  • the carrier component may be lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder May be used, and in addition, if the formulation is a spray, it may further comprise at least one propellant selected from the group consisting of chlorofluorohydrocarbons, propane / butane, and dimethyl ether.
  • the carrier component may be a solvent, a solubilizing agent or an emulsifying agent. More specifically, the carrier component is selected from the group consisting of water, ethanol, isopropanol, ethylcarbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan fatty acid esters It can be more than one.
  • the carrier component may be a liquid diluent such as water, ethanol or propylene glycol, an ethoxylated isostearyl alcohol, A suspending agent such as polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar or tracant may be used.
  • the carrier component is selected from aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, A fatty acid amide ether sulfate, an alkylamidobetaine, an aliphatic alcohol, a fatty acid glyceride, a fatty acid diethanolamide, a vegetable oil, a linolen derivative, or an ethoxylated glycerol fatty acid Esters may be used.
  • the carrier component of this kind can be mixed with cosmetics according to the invention (serving as an active ingredient of the cosmetics to be produced) in various mixing ratios, depending on the use of the cosmetics to be produced, Known techniques can be appropriately applied.
  • oleanolic acid 50 mg, oleanolic acid, and 2000 mg of polyethylene glycol (PEG400) are mixed with stirring to prepare a first mixture of oleanolic acid.
  • PEG400 polyethylene glycol
  • Poloxamer 407 F127 was added to the first oleanolic acid mixture prepared in the first step, and the mixture was heated and stirred at 60 ° C to prepare a second oleanolic acid mixture.
  • Nanoparticulate preparations prepared according to Example 1 are each administered to the skin surface.
  • test solutions according to Example 1 were sampled at 1, 2, 4, 6, 8, 10, 20, and 24 hours using 1 ml of receptor phase using a syringe. Respectively.
  • the permeation amount of the nanoparticle-containing particles containing oleic acid per hour was measured by HPLC and the peak area was determined. After calculating the concentration of each of the test solutions according to Example 1, the permeation amount of the skin was calculated.
  • the transdermal permeability increased with time, and it was confirmed that about 15% of the nanoparticle-containing particles containing oleoanic acid were permeated for 24 hours, and less than about 10% of the accumulated amount was accumulated in the skin.
  • the cosmetic product according to the present invention as described above can improve the skin permeation effect of oleanolic acid having the effect of improving the wrinkles of skin through the use of the nanoparticles of oleic acid in the solubilized and micellized state, There is a high possibility.

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Abstract

La présente invention concerne un produit cosmétique pour réduire les rides de la peau et, plus spécifiquement, un produit cosmétique antivieillissement contenant un produit soluble nanoparticulaire obtenu par la solubilisation et la micellisation, avec un polymère amphiphile, d'acide oléanolique, lequel est efficace pour réduire les rides de la peau mais est peu soluble, ce qui accroît sa solubilité dans l'eau ; et constitue un solvant contenu dans le produit cosmétique, et améliore la pénétration dans la peau.
PCT/KR2017/015677 2017-12-27 2017-12-28 Produit cosmétique antivieillissement contenant un produit soluble nanoparticulaire obtenu par la solubilisation d'acide oléanolique faiblement soluble, et procédé de préparation de produits cosmétiques antivieillissement WO2019132070A1 (fr)

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KR10-2017-0181368 2017-12-27
KR1020170181368A KR20190079276A (ko) 2017-12-27 2017-12-27 난용성 올레아노릭산을 가용화한 나노입자 유용물을 포함하는 항노화 화장품 및 항노화 화장품 제조방법

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KR102396548B1 (ko) * 2020-05-28 2022-05-10 한국화학연구원 항산화 및 주름개선 유효성분이 봉입된 나노입자, 이의 제조방법 및 이를 유효성분으로 함유하는 항산화 주름개선용 액상 소재 조성물
KR102591099B1 (ko) * 2021-03-31 2023-10-18 한스텍주식회사 천연 성분을 이용한 보습과 항산화 기능을 갖는 화장품 제조방법
KR102604090B1 (ko) * 2022-11-15 2023-11-21 한국콜마주식회사 난용성 성분을 안정화한 자외선 차단용 화장료 조성물

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