WO2012152567A2 - Procédé permettant d'éclaircir la peau - Google Patents

Procédé permettant d'éclaircir la peau Download PDF

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Publication number
WO2012152567A2
WO2012152567A2 PCT/EP2012/057352 EP2012057352W WO2012152567A2 WO 2012152567 A2 WO2012152567 A2 WO 2012152567A2 EP 2012057352 W EP2012057352 W EP 2012057352W WO 2012152567 A2 WO2012152567 A2 WO 2012152567A2
Authority
WO
WIPO (PCT)
Prior art keywords
extract
skin
acid
amine
plant material
Prior art date
Application number
PCT/EP2012/057352
Other languages
English (en)
Other versions
WO2012152567A3 (fr
Inventor
Punam Bandyopadhyay
Kishore BHONSLE
Sujeetkumar Jha
Anita DAMODARAN
Dharm PRAKASH
Nagalakshmi Surendra
Vinod Kumar
Original Assignee
Unilever N.V.
Unilever Plc
Hindustan Unilever Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever N.V., Unilever Plc, Hindustan Unilever Limited filed Critical Unilever N.V.
Priority to EA201301256A priority Critical patent/EA201301256A1/ru
Priority to BR112013027775A priority patent/BR112013027775A2/pt
Priority to EP12716012.5A priority patent/EP2706973A2/fr
Priority to CN201280022899.6A priority patent/CN103517701A/zh
Publication of WO2012152567A2 publication Critical patent/WO2012152567A2/fr
Publication of WO2012152567A3 publication Critical patent/WO2012152567A3/fr

Links

Classifications

    • 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
    • A61K8/18—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
    • A61K8/345—Alcohols 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • A61K8/673—Vitamin B group
    • A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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

Definitions

  • the invention relates to a method of lightening skin.
  • the invention more particularly relates to a method which provides enhanced skin lightening from a natural extract.
  • JP 418 017 discloses a sebum secretion promoting agent which is made by selecting one or more compounds selected from citric acid, succinic acid, fumaric acid, malic acid or an ester thereof and an extracted solution of Salvia officinalis L. with ethanol.
  • JP 2001 163755 discloses a preparation for external use for skin for improved skin bleaching effect, excellent in stability and safety by including at least one plant extract selected from those derived from Morus alba, Scutellaria baicalensis, Rosamarinus officinalis, Matricaria chamomilla, Aloe ferox (or Aloeafricane, Aloe spicata, Aloe barbadensis or Aloe arborescens), Hamamelis virginiana, Aesculus hippocastanum, Rose multiflora or species closely related thereto (Rosaceae), Salvia officinalis, Lamium album, Isodon japonicus (or Isodon trichocarpus), Glycyrrhiza glabra (or Glycyrrhiza uralensis), Saxifraga stolonfera, Rosa centigolia, and/or Pyracantha fortuneana, and an acylated derivative of glycos
  • US 2001/029266 discloses a composition comprising at least 0. 02% of at least one pentacyclic triterpenic acid, preferably ursolic acid or oleanolic acid, and at least one emulsifier, wherein said emulsifier is an optionally oxyalkylenated fatty acid monoester which is liquid at 25°C. and has an HLB greater than or equal to 12.
  • the present invention provides for a method of lightening skin comprising the step of applying to the desired skin surface a skin lightening composition comprising, a) 0.01 to 5% by weight an extract of a plant material comprising 0.1 % to 100% ursolic acid;
  • an activity enhancer comprising a mixture of an organic amine, a polyhydric alcohol and a non-ionic surfactant
  • “Skin lightening composition” as used herein, is meant to include a composition for topical application to skin of mammals, especially humans. Such a composition may be generally classified as leave-on or rinse off preferably leave-on. It includes any product applied to a human body primarily for lightening the colour of the skin but may also provide improved appearance, cleansing, odor control, photoprotection or general aesthetics. They may also be incorporated in compositions which are primarily meant as antiperspirants, deodorants, depilatories, lipsticks, foundations, mascara, sunscreen lotions, shampoos, or conditioners but provide additional benefits of skin lightening.
  • “Skin” as used herein is meant to include skin on the face and body (e.g., neck, chest, back, arms, underarms, hands, legs, buttocks and scalp).
  • the present invention is primarily targeted to skin lightening applications.
  • the inventors have surprisingly found that in addition to providing the skin lightening benefit, advantages like anti-aging and relief from photo damage are also provided.
  • the skin lightening composition is preferably in the form of a cream, lotion, stick, roll-on, gel or in propellant containing aerosol form. They are preferably in the cream, lotion, gel or stick form, most preferably a cream form.
  • the skin lightening composition comprises a specific extract of a plant material, an activity enhancer which is a mixture of organic amine, polyhydric alcohol and non- ionic surfactant and a cosmetically acceptable vehicle.
  • the composition comprises 0.01 to 5%, preferably 0.1 to 5% by weight an extract of a plant material comprising 0.1 to 100% ursolic acid.
  • the extract of plant material preferably additionally comprises 0.1 to 50 % oleanolic.
  • Ursolic acid and oleanolic have the structures given below:
  • the plant material for providing the extract used in the invention is preferably Salvia officinalis.
  • Salvia officinalis is often referred to by the common name of Garden sage or Common sage. It is a small perennial evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers. It is a member of the family Lamiaceae and is native to the Mediterranean region. It is cultivated in many European countries and in North America. It has been used in medicinal preparations and in foods.
  • the leaves and soft stems of Salvia officinalis are used for extracting the desired actives, preferably the leaves.
  • Sage leaf contains the following chemical class of compounds: catechin-type tannins, phenolic acids, flavonoids, essential oil and triterpenoids which includes oleanolic and ursolic acids.
  • a preferred process of extracting the extract from the plant material comprising 0.1 to 100% ursolic acid for use in the composition of the invention is prepared using a process comprising the steps of (a) contacting the plant material Salvia officinalis with a non-polar solvent selected from hexane, ethyl acetate, toluene, chloroform, diethyl ether or methylene chloride or a mixture thereof to prepare a mixture; and (b) separating the solvent from the mixture to prepare the extract.
  • the separation of the solvent may be carried out by any known method.
  • a preferred method is evaporation of the solvent under vacuum, preferably followed by filtration, washing and drying to a powder.
  • the extract may be further purified by a step of washing the extract with a solvent which may be hexane, acetone or a mixture thereof. Further purification steps may involve dissolving the extract in a basic solution e.g. alkaline ammonia followed by filtering the solution free of insoluble material and neutralizing the solution with acid to a neutral pH to precipitate the desired extract which may be further washed with distilled water and dried to a powder which contains ursolic acid.
  • a basic solution e.g. alkaline ammonia
  • filtering the solution free of insoluble material and neutralizing the solution with acid to a neutral pH to precipitate the desired extract which may be further washed with distilled water and dried to a powder which contains ursolic acid.
  • the plant extract preferably comprises 0.1 to 100 % ursolic acid. In a highly preferred aspect both ursolic acid and oleanolic are present. A further more highly preferred aspect provides for ursolic acid to be present in 60 to 85 % and oleanolic to be present in 15 to 40 % by weight of the plant extract.
  • extract is meant a product in dry form which could be in powder, granule or in the form of lumps. The percentage of fatty acid in the extract of plant material throughout this specification, unless mentioned otherwise, is on dry weight basis.
  • the composition comprises an activity enhancer selected from an organic base.
  • organic base is meant a compound which contains the functional groups -NH2, -NHR or -NR2 , (where R may be alkyl or aryl) and gives a pH of about 10 to 12 in water at 1 % concentration.
  • a preferred organic base is an amine compound.
  • Preferred amine compounds include alkanol amines like monoethanol amine, diethanolamines, triethanol amine and alkyl amines like methylamine, ethylamine, dimethyl amine, diethyl amine, dimethylethyl amine and triethyl amine.
  • Amines are preferably present in 0.05 to 5 %, more preferably 0.1 to 2.5 % by weight of the composition.
  • the composition comprises an additional activity enhancer selected from polyhydric alcohols.
  • Polyhydric alcohols useful for inclusion in the composition of the invention may be selected from alkylene glycols or polyalkylene glycols. Examples of polyhydric alcohols useful in the composition of the invention are ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycols, propylene glycol, butanediol, pentanediol, hexanediol, glycerol or phytantriol When included polyhydric alcohols are present in 0.01 to 10 %, preferably 0.1 to 5 % by weight of the composition.
  • Suitable ratio of amine and polyhydric alcohol is in the range of 1 :1 to 1 :5.
  • Total amount of activity enhancer is preferably in the range of 1 to 10 % by weight of the composition.
  • Most preferred organic amine is triethanol amine.
  • Most preferred polyhydric alcohol is propylene glycol.
  • the composition of the invention that provides the skin lightening comprises a cosmetically acceptable vehicle.
  • the cosmetically acceptable vehicle preferably comprises 1 to 25 % fatty acid.
  • the cosmetically acceptable vehicles are preferably in a cream, lotion, gel or emulsion format.
  • a more preferred format is a cream, further more preferably a vanishing cream.
  • Vanishing cream base is one which comprises 1 to 25 %, more preferably 5 to 20 % fatty acid.
  • the base preferably comprises 0.1 to 10 %, more preferably 0.1 to 3 % soap.
  • C12 to C20 fatty acids are especially preferred in vanishing cream bases, further more preferred being CM to C18 fatty acids.
  • the fatty acid is preferably substantially a mixture of stearic acid and palmitic acid.
  • Soaps in the vanishing cream base include alkali metal salt of fatty acids, like sodium or potassium salts
  • the soap is preferably the potassium salt of the fatty acid mixture.
  • the fatty acid in vanishing cream base is often prepared using hystric acid which is substantially (generally about 90 to 95 %) a mixture of stearic acid and palmitic acid. Thus inclusion of hystric acid and its soap to prepare the vanishing cream base is within the scope of the present invention. It is particularly preferred that the composition comprises at least 6 %, preferably at least 10 %, more preferably at least 12 % fatty acid.
  • the cosmetically acceptable vehicle is usually from 10 to 99.9 %, preferably from 50 to 99 % by weight of the composition.
  • the cosmetically acceptable vehicle preferably includes water. Water is preferably included in 35 to 90 %, more preferably 50 to 85 %, further more preferably 50 to 80 % by weight of the composition.
  • the composition comprises a non-ionic surfactant.
  • Non-ionic surfactant has also been seen to be a skin lightening activity enhancer in certain cases, in addition to its known properties. In addition to the mechanism of action of the other activity enhancer hereinabove described, non-ionic surfactants enable enhancement of skin lightening activity, in the present invention, by way of improving spreading of the formulation on the skin where it is applied.
  • the non-ionic surfactant may be present in 0.01 to 10 %, preferably 0.1 to 5 %, more preferably 0.1 to 3 % by weight of the composition.
  • Preferred non-ionic surfactants are those that have an HLB value of at least 9.0.
  • non-ionic surfactants suitable for inclusion in the composition of the invention are:
  • the classes (i) and (ii) are generally known as the Brij surfactants, the class (iii) is generally known as the Triton class and the classes (iv) and (v) are called the Tween class.
  • Suitable examples of (a) fatty alcohol ethoxylates with saturated carbon chain and having HLB higher than 15.5 or from (b) the class of fatty alcohol ethoxylates with unsaturated carbon chain with HLB higher than 12 are Brij 35 (a C12EO23 compound), Brij 97 (unsaturated C18EO12), Brij 700 (C18EO100) or Brij 99 (unsaturated C18EO20).
  • Suitable examples of (c) alkyl phenol ethoxylates with HLB higher than 15 for use in the composition of the invention are Triton X 165, Triton X 305, Triton 405, or Triton X 705.
  • Suitable examples of (d) polyoxyethylene sorbitan alkyl esters with saturated C12 to C16 carbon chain and having HLB higher than 12 and (e) polyoxyethylene sorbitan alkyl esters with unsaturated C18 carbon chain and having HLB higher than 9 are Tween 20, Tween 21 , Tween 40, Tween 80, Tween 81 or Tween 85 trioleate.
  • composition of the invention has a pH in the range of 6 to 8.
  • the composition may additionally comprise another skin lightening agent.
  • the skin lightening agent is preferably chosen from a vitamin B3 compound or its derivative e.g. niacin, nicotinic acid, niacinamide.
  • Other well known skin lightening agents which may be included are aloe extract, ammonium lactate, azelaic acid, kojic acid, butyl hydroxy anisole, butyl hydroxy toluene, citrate esters, 2, 5- dihydroxybenzoic acid and its derivatives, ellagic acid, gluconic acid, glycolic acid, green tea extract, hydroquinone, 4-hydroxy benzoic acid derivatives, hydroxycaprylic acid, lemon extract, linoleic acid, magnesium ascorbyl phosphate, salicylic acid, or vitamins like vitamin B6, vitamin B12, vitamin C, vitamin A, hydroxycarboxylic acid like lactic acid and their salts e.g.
  • Vitamin B3 compound or its derivative e.g. niacin, nicotinic acid, niacinamide are the more preferred additional skin lightening agent as per the invention, most preferred being niacinamide.
  • additional skin lightening agent when included, is preferably present in an amount in the range of 0.1 to 10 %, more preferably 0.2 to 5 % by weight of the composition.
  • the personal care composition may preferably additionally comprise one or more UV sunscreens.
  • the UV sunscreens may be inorganic or organic.
  • UV-A / UV-B sunscreen agents include, 2-hydroxy-4-methoxybenzophenone, octyldimethyl-p- aminobenzoic acid, digalloyltrioleate, 2,2-dihydroxy-4-methoxybenzophenone, ethyl-4-(bis(hydroxypropyl)) aminobenzoate, 2-ethylhexyl-2-cyano-3,3- diphenylacrylate, 2-ethylhexylsalicylate, glyceryl-p-aminobenzoate, 3,3,5- trimethylcyclohexylsalicylate, methylanthranilate, p-dimethyl-aminobenzoic acid or aminobenzoate, 2-ethylhexyl-p-dimethyl-amino-benzoate, 2-phenylbenzimidazole- 5-sulfonic acid, 2-(p-d
  • the composition comprises both 2-ethylhexyl-p-methoxycinnamate and butylmethoxydibenzoylmethane. It has been observed that 2-ethylhexyl-p- methoxycinnamate is especially useful for inclusion in the composition as there is enhanced skin lightening which is over and above that afforded by the sunscreening property of the cinnamate.
  • oil soluble sunscreens like 2-ethylhexyl-p-methoxycinnamate afford enhanced solubilisation of the actives like ursolic acid and oleanolic acid thereby enhancing skin lightening efficacy.
  • a safe and effective amount of sunscreen may be used in the compositions of the present invention.
  • the composition preferably comprises from about 0.1 % to about 10 %, more preferably from about 0.1 to about 5 %, of a sunscreen agent.
  • Useful inorganic sun-blocks are also preferably used in the present invention. These include, for example, zinc oxide iron oxide, silica, such as fumed silica, and titanium dioxide.
  • the composition may additionally comprise deodourant actives for preparation of a deodourant composition which by way of the invention provides fast kinetics of skin lightening.
  • Deodourant compositions are applied on many areas of the human body but are especially popular for use in the axilla or the underarm area.
  • Deodourant compositions can generally be in the form of firm solids, soft solids, gels, creams, liquids, or sprays and are dispensed using applicators appropriate to the physical characteristics of the composition.
  • the composition is preferably in the cream format.
  • Deodourant compositions may or may not additionally comprise anti-perspirant actives.
  • the composition may also comprise other diluents.
  • the diluents act as a dispersant or carrier for other materials present in the composition, so as to facilitate their distribution when the composition is applied to the skin.
  • Diluents other than water can include liquid or solid emollients, solvents, humectants, thickeners and powders.
  • the cosmetically acceptable vehicle is usually from 10 to 99.9 %, preferably from 50 to 99 % by weight of the composition, and can, in the absence of other cosmetic adjuncts, form the balance of the composition.
  • the compositions can comprise a wide range of other optional components.
  • antioxidants examples include: antioxidants, binders, biological additives, buffering agents, colorants, thickeners, polymers, astringents, fragrance, humectants, opacifying agents, conditioners, exfoliating agents, pH adjusters, preservatives, natural extracts, essential oils, skin sensates, skin soothing agents, and skin healing agents.
  • compositions as shown in table 1 were prepared and the skin lightening efficacy was tested using the (MRIV) protocol as described below.
  • Protocol A trial was carried out for 10 days with 15 volunteers. The trial consisted of the procedure as described below:
  • a specific portion of the volunteer's forearm was marked out and formulations were applied (3 mg/cm 2 ) five times daily in about equal intervals of time.
  • the skin lightening score was measured by expert assessors using a colour ruler on a scale of 1 to 10.
  • the average skin lightening score is the change in skin colour with respect to the initial skin colour. A more negative score indicates a higher degree of skin lightening. A more positive score indicates skin darkening.
  • the extract of Salvia officinalis had 64 % ursolic acid and 21 % oleanolic acid.
  • the data in table 1 indicates that the composition as per the invention (example 3) which has the activity enhancer in addition to the extract of natural source high in ursolic acid provides for vastly improved skin lightening efficacy as compared to composition outside the invention (examples 2) and a conventional cosmetically acceptable base without any skin lightening active (example 1 ). Further, inclusion of a vitamin B3 compound, i.e. niacinamide in the composition of the invention enhances the skin lightening activity further (example 4).
  • a vitamin B3 compound i.e. niacinamide

Abstract

L'invention concerne un procédé permettant d'éclaircir la peau, plus particulièrement, un procédé permettant d'obtenir un meilleur éclaircissement de la peau à partir d'un extrait naturel. On sait que l'extrait de sauge officinale (Salvia officinalis) a été utilisé en application sur la peau afin d'obtenir de nombreux bénéfices. Les inventeurs ont démontré qu'ils obtenaient une efficacité supérieure dans l'éclaircissement de la peau à partir de cette matière naturelle grâce à l'utilisation d'une classe sélectionnée de renforçateurs d'activité.
PCT/EP2012/057352 2011-05-12 2012-04-23 Procédé permettant d'éclaircir la peau WO2012152567A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EA201301256A EA201301256A1 (ru) 2011-05-12 2012-04-23 Способ осветления кожи
BR112013027775A BR112013027775A2 (pt) 2011-05-12 2012-04-23 método de clareamento de pele
EP12716012.5A EP2706973A2 (fr) 2011-05-12 2012-04-23 Procédé permettant d'éclaircir la peau
CN201280022899.6A CN103517701A (zh) 2011-05-12 2012-04-23 亮肤的方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1455/MUM/2011 2011-05-12
IN1455MU2011 2011-05-12
EP11177301 2011-08-11
EP11177301.6 2011-08-11

Publications (2)

Publication Number Publication Date
WO2012152567A2 true WO2012152567A2 (fr) 2012-11-15
WO2012152567A3 WO2012152567A3 (fr) 2013-09-26

Family

ID=45998370

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/057352 WO2012152567A2 (fr) 2011-05-12 2012-04-23 Procédé permettant d'éclaircir la peau

Country Status (5)

Country Link
EP (1) EP2706973A2 (fr)
CN (1) CN103517701A (fr)
BR (1) BR112013027775A2 (fr)
EA (1) EA201301256A1 (fr)
WO (1) WO2012152567A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019174867A1 (fr) * 2018-03-13 2019-09-19 Unilever N.V. Composition de désinfectant
US10869862B2 (en) 2016-05-26 2020-12-22 Conopco, Inc. Antimicrobial compositions for topical use
WO2022133715A1 (fr) * 2020-12-22 2022-06-30 L'oreal Composition pour éclaircir et/ou blanchir des matières kératiniques
EP4186488A1 (fr) * 2021-11-26 2023-05-31 Unilever IP Holdings B.V. Composition topique

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Publication number Priority date Publication date Assignee Title
JPH0418017A (ja) 1990-05-09 1992-01-22 Noevir Co Ltd 皮脂分泌促進剤
JP2001163755A (ja) 1999-12-07 2001-06-19 Shiseido Co Ltd 皮膚外用剤
US20010029266A1 (en) 1999-12-10 2001-10-11 L'oreal Composition containing a pentacyclic triterpenic acid, method

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MY124001A (en) * 1999-04-23 2006-06-30 E Excel Int Dietary supplements containing dehydrated cactus fruit juice and ginseng berry juice
JP2002241299A (ja) * 2001-02-13 2002-08-28 Ichimaru Pharcos Co Ltd メイラード反応修復剤
KR20050092313A (ko) * 2004-03-15 2005-09-21 주식회사 엘지생활건강 멜라닌 생성 억제 활성을 갖는 식물 추출물을 함유하는피부미백용 화장료
JP4528745B2 (ja) * 2006-06-14 2010-08-18 日光ケミカルズ株式会社 チロシナーゼ産生抑制剤
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Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
JPH0418017A (ja) 1990-05-09 1992-01-22 Noevir Co Ltd 皮脂分泌促進剤
JP2001163755A (ja) 1999-12-07 2001-06-19 Shiseido Co Ltd 皮膚外用剤
US20010029266A1 (en) 1999-12-10 2001-10-11 L'oreal Composition containing a pentacyclic triterpenic acid, method

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10869862B2 (en) 2016-05-26 2020-12-22 Conopco, Inc. Antimicrobial compositions for topical use
WO2019174867A1 (fr) * 2018-03-13 2019-09-19 Unilever N.V. Composition de désinfectant
CN111787903A (zh) * 2018-03-13 2020-10-16 荷兰联合利华有限公司 消毒剂组合物
CN111787903B (zh) * 2018-03-13 2023-08-15 联合利华知识产权控股有限公司 消毒剂组合物
WO2022133715A1 (fr) * 2020-12-22 2022-06-30 L'oreal Composition pour éclaircir et/ou blanchir des matières kératiniques
CN116669686A (zh) * 2020-12-22 2023-08-29 莱雅公司 用于增亮和/或增白角蛋白材料的组合物
EP4186488A1 (fr) * 2021-11-26 2023-05-31 Unilever IP Holdings B.V. Composition topique
WO2023094517A1 (fr) 2021-11-26 2023-06-01 Unilever Ip Holdings B.V. Composition topique

Also Published As

Publication number Publication date
EP2706973A2 (fr) 2014-03-19
EA201301256A1 (ru) 2014-03-31
BR112013027775A2 (pt) 2016-08-23
WO2012152567A3 (fr) 2013-09-26
CN103517701A (zh) 2014-01-15

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