WO2010064878A2 - Composition cosmétique anti-rides pour la peau contenant de l'acide leontopodique et un principe actif - Google Patents

Composition cosmétique anti-rides pour la peau contenant de l'acide leontopodique et un principe actif Download PDF

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WO2010064878A2
WO2010064878A2 PCT/KR2009/007271 KR2009007271W WO2010064878A2 WO 2010064878 A2 WO2010064878 A2 WO 2010064878A2 KR 2009007271 W KR2009007271 W KR 2009007271W WO 2010064878 A2 WO2010064878 A2 WO 2010064878A2
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Prior art keywords
acid
leontopodic
leontopodic acid
skin
nanoliposomes
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PCT/KR2009/007271
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English (en)
Korean (ko)
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WO2010064878A3 (fr
Inventor
김한성
안순애
김덕희
김진웅
김한곤
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(주)아모레퍼시픽
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Priority to CN200980148755.3A priority Critical patent/CN102238935B/zh
Publication of WO2010064878A2 publication Critical patent/WO2010064878A2/fr
Publication of WO2010064878A3 publication Critical patent/WO2010064878A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/55—Phosphorus compounds
    • 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
    • A61K8/14—Liposomes; Vesicles
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66—Enzymes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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

Definitions

  • the present invention is Leontopodic acid represented by the formula (1); 2 - [(3 S) -3 -hydroxybutanate] -3,4,5-tris - [(2 E) -3- (3,4-dihydroxyphenyl) -2-propenoate] -D-glucaric acid ⁇ of the active ingredient It relates to a skin cosmetic composition for improving wrinkles.
  • Skin is the body's primary protective film, protecting organs in the body from changes in temperature and humidity, stimuli from the external environment such as ultraviolet rays and pollutants, and playing an important role in maintaining homeostasis such as body temperature control.
  • stimuli from the external environment such as ultraviolet rays and pollutants
  • body temperature control e.g., body temperature control
  • excessive physical and chemical stimuli, stress, and malnutrition from the outside will degrade the normal function of the skin and promote skin aging such as loss of elasticity, keratinization and wrinkle formation.
  • the conventional cosmetics used to maintain the skin has a variety of problems, such as ineffective or cause skin side effects.
  • the present invention is to solve the above problems of the prior art, an object of the present invention is to contain the collagenase expression inhibitory effect, collagen biosynthesis promoting effect and wrinkle improvement effect by containing as a active ingredient Leontopodic acid excellent in wrinkle improvement effect It is to provide an excellent skin cosmetic composition for wrinkle improvement.
  • the present invention provides a skin cosmetic composition for improving wrinkles, characterized in that it contains Leontopodic acid as an active ingredient.
  • the leontopodic acid is characterized in that it contains 0.0001% to 10% by weight based on the total weight of the total composition.
  • the Leontopodic acid collected in the nanoliposome is contained in 0.001 to 50% by weight relative to the total weight of the composition.
  • Wrinkle improvement skin cosmetic composition of the present invention is characterized by inhibiting the expression of collagenase, promoting collagen biosynthesis.
  • the anti-wrinkle skin cosmetic composition containing the Leontopodic acid of the present invention as an active ingredient is excellent in collagenase expression inhibitory effect, collagen biosynthesis promoting effect and wrinkle improvement effect.
  • the formulation stability and percutaneous absorption ability are more excellent when the stabilized leontopodic acid is contained in the nanoliposomes.
  • 1 is a photograph showing the in vivo wrinkle improvement effect of wrinkles derived from squalene monoperoxide.
  • Figure 2 is a photograph showing the effect of improving the wrinkles (in vivo) wrinkles derived from UV.
  • the present invention provides a skin cosmetic composition for anti-wrinkle, characterized in that it contains Leontopodic acid as an active ingredient.
  • the leontopodic acid is characterized in that it contains 0.0001% to 10% by weight based on the total weight of the total composition.
  • the Leontopodic acid collected in the nanoliposome is characterized in that it contains 0.001 to 50% by weight based on the total weight of the composition
  • Leontopodic acid is one of the main components contained in a large amount of edelweiss.
  • Edelweiss is a perennial plant of the dicotyledon plant Campanula Asteraceae, scientific name is Leontopodium alpinum. It is native to the European Alps and is an alpine plant. In Korea, similar foot, mountain, and Halla foot bridges grow in the high mountains.
  • Edelweiss has long been used to treat diseases such as abdominal pain, tonsillitis, bronchitis, cancer, dysentery, diarrhea and fever.
  • Edelweiss is exposed to extreme conditions such as strong UV in the Alps, excessive temperature and humidity changes, and strong winds.
  • Edelweiss contains a variety of ingredients, including phenolic acids, lignans, flavonoids, sesquiterpenes, benzofuran, pyran derivatives, polyacetylenes, coumarins, diterpene acids, and the like.
  • the Leontopodic acid is crushed edelweiss (a); (B) extracting the pulverized product of step (a) onto a paper selected from a solvent consisting of water, anhydrous or hydrous alcohol having 1 to 4 carbon atoms, and acetone; And re-extracting the extract of step (b) to at least one selected from a solvent consisting of ethyl acetate, diethyl ether, benzene, chloroform, and hexane.
  • the four anhydrous or hydrous alcohols may be methanol, ethanol, 1,3-butylene glycol, normal propanol, isopropanol or normal butanol and the extraction of steps (b) and (c) may be cold, percolation or It can be done by way of warming.
  • the nanoliposomes may have an average particle diameter of 10-500nm.
  • Wrinkle improvement skin cosmetic composition of the present invention is characterized by inhibiting the expression of collagenase, promoting collagen biosynthesis.
  • Leontopodic acid contained in the skin cosmetic composition according to an embodiment of the present invention is the first extraction of edelweiss from anhydrous or lower alcohol, water or acetone of anhydrous or low, such as ethyl acetate, diethyl ether, benzene, chloroform, hexane
  • anhydrous or low such as ethyl acetate, diethyl ether, benzene, chloroform, hexane
  • the Leontopodic acid production method will be described in more detail below. However, the preparation method of leontopodic acid is not limited below.
  • the edelweiss are finely pulverized, and as an extraction solvent, water which is a polar solvent, anhydrous or hydrous lower alcohol having 1 to 4 carbon atoms (methanol, ethanol, 1,3-butylene glycol, normal propanol, isopropanol or normal butanol, etc.), water And a mixture of the lower alcohol, acetone, or a mixture of the solvents are added at a weight ratio of 5 to 20 times the dry weight of the edelweiss pulverized product, followed by immersion extraction, filtration, and concentration under reduced pressure.
  • water which is a polar solvent, anhydrous or hydrous lower alcohol having 1 to 4 carbon atoms (methanol, ethanol, 1,3-butylene glycol, normal propanol, isopropanol or normal butanol, etc.)
  • water And a mixture of the lower alcohol, acetone, or a mixture of the solvents are added at a weight ratio of 5 to 20 times the dry weight of the edelweis
  • a low polar organic solvent such as ethyl acetate, chloroform and diethyl ether is added to the dispersion and shaken. After shaking, the organic layer is separated and concentrated under reduced pressure to obtain an edelweiss extract having excellent activity.
  • Leontopodic acid obtained by the above method has an anti-wrinkle effect and is manufactured with skin cosmetics such as an ointment or lotion for external skin and can be used as a safe and effective skin anti-wrinkle agent even when applied to human skin without side effects.
  • Leontopodic acid prepared as described above is suitably contained in 0.0001 to 10% by weight, preferably 0.0005 to 5.0% by weight based on the total weight of the total composition. This is because a distinct effect could not be expected at concentrations of 0.0001% by weight or less, and no increase in effect was observed with an increase in content at concentrations of 10.0% by weight or more.
  • the nanoliposomes are liposomes having the form of liposomes, and mean liposomes having an average particle diameter of 10-500 nm.
  • the average particle diameter of the nanoliposomes is 50-300 nm.
  • the average particle diameter of the nanoliposomes exceeds 300 nm, the improvement of skin penetration and the improvement of formulation stability are very weak among the technical effects to be achieved in the present invention.
  • Nanoliposomes used to stabilize the Leontopodic acid extract according to one embodiment of the present invention are prepared by a mixture comprising polyols, oily ingredients, surfactants, phospholipids, fatty acids and water.
  • the polyol used in the nanoliposome of one embodiment of the present invention is not particularly limited, preferably propylene glycol, dipropylene glycol, 1,3-butylene glycol, glycerin, methylpropanediol, isopropylene glycol Lycol, pentylene glycol, erythritol, xylitol, sorbitol and mixtures thereof.
  • the amount used is 10-80% by weight, preferably 30-70% by weight based on the total weight of the nanoliposomes.
  • Oil component used in the preparation of nanoliposomes of one embodiment of the present invention may be used a variety of oils known in the art, preferably hydrocarbon-based oils, such as hexadecane and paraffin oil, ester-based Silicone oils such as synthetic oils, dimethicone and cyclomethicone series, animal and vegetable oils such as sunflower oil, corn oil, soybean oil, avocado oil, sesame oil and fish oil, ethoxylated alkyl ether oil, propoxylated alkyl Ether-based oils, sphingoidoid lipids such as phytosphingosine, sphingosine and sphinginine, cerebroside cholesterol, cytosterol cholesteryl sulfate, cytosteryl sulfate, C 10-40 fatty alcohols and mixtures thereof.
  • the amount used is 1.0-30.0% by weight, preferably 3.0-20.0% by weight based on the total weight of nanoliposomes.
  • Surfactants used in the preparation of the nanoliposomes of one embodiment of the present invention can be used in any known in the art.
  • anionic surfactants cationic surfactants, amphoteric surfactants and nonionic surfactants can be used.
  • Specific examples of anionic surfactants include alkylacylglutamate, alkylphosphates, alkyllactylates, dialkylphosphates and trialkylphosphates.
  • Specific examples of nonionic surfactants include alkoxylated alkylethers, alkoxylated alkylesters, alkylpolyglycosides, polyglyceryl esters and sugar esters.
  • Particularly preferred surfactants are polysorbates belonging to nonionic surfactants.
  • the amount used is 0.1-10% by weight, preferably 0.5-5.0% by weight relative to the total weight of nanoliposomes.
  • Phospholipids another component used in the preparation of nanoliposomes of one embodiment of the present invention, are used with amphoteric lipids, including natural phospholipids (eg, egg yolk lecithin or soy lecithin, sphingomyelin) and synthetic phospholipids (eg For example, dipalmitoylphosphatidylcholine or hydrogenated lecithin, preferably lecithin. In particular, naturally occurring unsaturated lecithin or saturated lecithin extracted from soybean or egg yolk are preferred. Typically, lecithin derived from nature has 23-95% phosphatidylcholine and 20% or less phosphadidylethanolamine. In the preparation of the nanoliposomes of the present invention, the amount of lecithin used is 0.5-20.0% by weight, and preferably 2.0-8.0% by weight, based on the total weight of nanoliposomes.
  • natural phospholipids eg, egg yolk lecithin or soy lecithin,
  • Fatty acids used in the preparation of nanoliposomes of one embodiment of the present invention are higher fatty acids, preferably saturated or unsaturated fatty acids of a C 12-22 alkyl chain, for example, lauric acid, myristic acid, palmitic acid, stearic acid, Oleic acid and linoleic acid.
  • the amount used is 0.05-3.0 wt% with respect to the total weight of nanoliposomes, preferably 0.1-1.0 wt%.
  • Water used in the preparation of the nanoliposomes of one embodiment of the present invention is generally deionized distilled water, the amount of which is 5.0-40% by weight based on the total weight of the nanoliposomes.
  • the preparation of nanoliposomes can be accomplished through various methods known in the art, but most preferably, a mixture comprising the above components is applied to a high pressure homogenizer.
  • the preparation of nanoliposomes by the high pressure homogenizer can be carried out under various conditions (eg, pressure, frequency, etc.) according to the desired particle size, preferably 1-5 times of high pressure homogenase under a pressure of 600-1200 bar.
  • Nanoliposomes are prepared by passing through the Azure.
  • Leontopodic acid stabilized by nanoliposomes according to an embodiment of the present invention has the effect of increasing the stability and solubility and transdermal absorption in the formulation.
  • composition according to the invention contains cosmetically and dermatologically acceptable media and / or bases.
  • cosmetically and dermatologically acceptable media and / or bases are all formulations suitable for topical application, for example emulsions, suspensions, microemulsions, microcapsules, microgranules or ionic (liposomes) obtained by dispersing an oil phase in a solution, gel, solid or pasty anhydrous product, aqueous phase, and / or It may be provided in the form of a nonionic vesicle dispersant or in the form of a cream, skin, lotion, powder, ointment, spray or cone stick.
  • These compositions can be prepared according to conventional methods in the art.
  • the composition according to the invention can also be used in the form of a foam or in the form of an aerosol composition further containing a compressed propellant.
  • Compositions of the present invention include fatty substances, organic solvents, solubilizers, thickening and gelling agents, emollients, antioxidants, suspending agents, stabilizers, blowing agents, fragrances, surfactants, water, ionic or nonionic emulsifiers, fillers, metals
  • ion blockers and chelating agents preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic actives, lipid vesicles or any other ingredients commonly used in cosmetics It may contain a commonly used adjuvant. These adjuvants are introduced in amounts commonly used in the cosmetic or dermatological field.
  • the subfraction containing fractions obtained above was eluted with methanol in a glass column ( ⁇ 1.0 x 50 cm) filled with Sephadex (Sephadex LH-20, Pharmacia Biotech) to obtain Leontopodic acid (70 mg). .
  • Glycerin 580g, Caprylic capric triglyceride 200g, Phospholipid 50g, Cholesterol 20g are mixed and stabilized by stirring with a stirrer in order to stabilize the leontopodiic acid with nanoliposomes, and then mixed and dissolved by heating to 75 ° C, obtained in Example 1 50 g of leontopodic acid solid was added and completely dissolved. 100 g of purified water was slowly added thereto, mixed, and then passed through a high pressure emulsifier (Microfluidizer M210EH, Microfluidics, USA) three times under conditions of a pressure of 1000 bar at 50 ° C. to prepare nanoliposomes of leontopodic acid. The particle size of this liposome was approximately 70 nm.
  • Example 1 The collagen biosynthesis promoting effect of Example 1 was measured in comparison with tocopherol and EGCG which are known to promote collagen biosynthesis.
  • fibroblasts (PromoCell, Germany) were seeded (10 5 per hole) in 24 wells (seeding) and cultured until 90% growth. This was incubated in serum-free DMEM medium for 24 hours, and then Example 1, tocopherol and EGCG dissolved in serum-free medium were treated with 10 -4 molar concentration, respectively, and incubated in a CO 2 incubator for 24 hours. These supernatants were removed and procollagen increased or decreased using procollagen type I ELISA kit (procollagen type (I)). The results are shown in Table 1 below, where the synthetic ability is compared to the non-treated group as 100.
  • the collagenase expression inhibitory effect (production inhibition capacity) of Leontopodic acid obtained in Example 1 was measured as follows by using retinoic acid known to inhibit collagenase expression as a positive control group.
  • human fibroblasts were placed in a 96-well microtiter plate containing Dulbecco's Modified Eagle's Media (DMEM) medium containing 2.5% fetal bovine serum to 5,000 cells / well. Incubated until 90% growth. After culturing in serum-free DMEM medium for 24 hours, and then treated with Example 1, retinoic acid dissolved in serum-free DMEM medium for 10 hours at 10 -4 molarity, the cell culture was collected.
  • DMEM Dulbecco's Modified Eagle's Media
  • the degree of collagenase production was measured using the collagenase measuring instrument (Amersham Pharma Co., Ltd.) from the collected cell culture solution.
  • the cell culture medium collected in a 96-well plate uniformly coated with collagenase primary antibody was put in an antigen-antibody reaction for 3 hours. After 3 hours, the chromophore-bound secondary collagen antibody was placed in a 96-well plate and reacted for another 15 minutes. After 15 minutes, the coloring stimulant was added, causing color development at room temperature for 15 minutes, and 1M sulfuric acid was added again to stop the reaction (color development). The color of the reaction solution was yellow and the degree of yellow color was different according to the progress of the reaction.
  • the absorbance of the yellow 96-well plate was measured at 405 nm using an absorbance meter.
  • the expression level of collagenase was calculated by Equation 1 below, and the results are shown in Table 2 below. This is in contrast to the level of collagenase expression of the untreated group to 100. At this time, the cell culture liquid collected from the group not treated with the test substance was used as a control.
  • SqOOH + PEG400 is a test group treated with squalene monoperoxide and PEG400 as a solvent
  • SqOOH + PEG400 + leontopodic acid is treated with squalene monoperoxide and leontopodiic acid solution
  • SqOOH + PEG400 + retinoic acid is a test group treated with squalene monoperoxide and retinoic acid solution.
  • UV treatment group UV-leontopodic acid treatment group
  • UV-retinoic acid treatment group UV-retinoic acid treatment group
  • Topodic acid and retinoic acid were applied to the back of 100 ⁇ l each day for 8 weeks, and UVB was applied 3 MED (minimum erythema dose 3 times a week for 8 weeks).
  • UVB was applied 3 MED (minimum erythema dose 3 times a week for 8 weeks).
  • UVB was applied 3 MED (minimum erythema dose 3 times a week for 8 weeks).
  • UV irradiation was performed three times a week, and the sample solution was applied daily.
  • a replica of the dorsal area was removed using silicone and the depth of the wrinkles was evaluated using an image analyzer (SVI600, Courage + Khazaka electronic GmbH, Germany).
  • Skin absorption was measured by using Franz permeation cells on guinea pig skin. Immediately before the test, abdominal skin of the guinea pig was taken and cut into square 1 cm 2 areas, which were placed in a transmission cell having a diameter of 0.9 cm and fixed with a clamp. One side of the skin (donor container) was applied with a sample of Example 1 dissolved in a solvent (alcohol: butylene glycol 7: 3) and 0.2 g of Leontopodic acid stabilized with the nanoliposomes of Example 2, and on the opposite side. Cotton (receptor container) was in contact with the solvent mixed with purified water and ethanol in a weight ratio of 4: 1, the temperature was maintained at 32 °C the actual skin temperature during the test.
  • a solvent alcohol: butylene glycol 7: 3
  • the formulation of the composition containing leontopodic acid of the present invention can be arbitrarily selected, and can be prepared in various forms such as nourishing cream, nutrient lotion, massage cream, nutrient essence, softening lotion and skin cosmetics which are conventional cosmetic formulations. have.
  • Softening water containing leontopodic acid in the composition described below was prepared according to a conventional method.
  • a nutritive cream containing leontopodic acid in the composition described below was prepared according to a conventional method.
  • Leontopodic acid 1.0 Polyvinyl alcohol 13.0 Sodium Carboxymethyl Cellulose 0.2 glycerin 5.0 Allantoin 0.1 ethanol 6.0 PEG 12 nonylphenyl ether 0.3 Polysorbate 60 0.3 Preservatives, Colors and Flavors Quantity Purified water Remaining amount
  • Gels containing leontopodic acid stabilized with nanoliposomes with the compositions described below were prepared according to conventional methods.
  • the cosmetic composition according to the present invention can be variously used in the field of skin beauty and cosmetics.

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Abstract

La présente invention concerne une composition cosmétique anti-rides pour la peau contenant de l'acide leontopodique et un principe actif, laquelle composition présente des effets inhibiteurs de l'expression de la collagénase améliorés, des effets simulateurs de la biosynthèse du collagène améliorés et des effets anti-rides améliorés. En outre, la présente invention concerne une composition cosmétique anti-rides pour la peau contenant de l'acide leontopodique stabilisé avec un nanoliposome et qui présente une excellente stabilité de formulation et une excellente administration transdermique.
PCT/KR2009/007271 2008-12-05 2009-12-07 Composition cosmétique anti-rides pour la peau contenant de l'acide leontopodique et un principe actif WO2010064878A2 (fr)

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CN200980148755.3A CN102238935B (zh) 2008-12-05 2009-12-07 将火绒草酸作为有效成分含有的改善皱纹用皮肤化妆料组合物

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KR1020080122893A KR20100064451A (ko) 2008-12-05 2008-12-05 레온토포딕산을 유효성분으로 함유하는 주름개선용 피부 화장료 조성물
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US9849077B2 (en) 2014-03-10 2017-12-26 Mary Kay Inc. Skin lightening compositions
US10682381B2 (en) 2009-04-27 2020-06-16 Mary Kay Inc. Botanical formulations
US10780041B2 (en) 2011-12-19 2020-09-22 Mary Kay Inc. Combination of plant extracts to improve skin tone

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EP2623094A1 (fr) * 2012-02-02 2013-08-07 DSM IP Assets B.V. Utilisation d'extrait d'edelweiss
RU2599492C1 (ru) * 2015-05-19 2016-10-10 Общество с ограниченной ответственностью Научно-технический центр "Химинвест" (ООО НТЦ "Химинвест") Хвойно-угольный скраб для очищения кожи
CN110354028A (zh) * 2018-04-10 2019-10-22 伽蓝（集团）股份有限公司 一种高山火绒草提取物的应用
KR102105166B1 (ko) * 2018-06-20 2020-04-28 두리화장품 주식회사 솜다리의 기내배양을 이용한 대량 생산방법 및 솜다리 추출물을 유효성분으로 포함하는 항산화, 항염증 및 항주름용 조성물
CN116672276B (zh) * 2023-05-04 2024-06-14 安赛搏(重庆)生物技术有限公司 一种火绒草酸组合物及紧致抗皱的产品中的应用

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US10682381B2 (en) 2009-04-27 2020-06-16 Mary Kay Inc. Botanical formulations
US10953058B2 (en) 2009-04-27 2021-03-23 Mary Kay Inc. Botanical formulations
US11638735B2 (en) 2009-04-27 2023-05-02 Mary Kay Inc. Botanical formulations
US10780041B2 (en) 2011-12-19 2020-09-22 Mary Kay Inc. Combination of plant extracts to improve skin tone
US11865202B2 (en) 2011-12-19 2024-01-09 Mary Kay Inc. Combination of plant extracts to improve skin tone
US9849077B2 (en) 2014-03-10 2017-12-26 Mary Kay Inc. Skin lightening compositions
US10500152B2 (en) 2014-03-10 2019-12-10 Mary Kay Inc. Skin lightening compositions

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WO2010064878A3 (fr) 2010-07-22
CN102238935A (zh) 2011-11-09
CN102238935B (zh) 2014-07-30
KR20100064451A (ko) 2010-06-15

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