WO2007082908A2 - Utilisation de derives de biuret pour hydrater la peau - Google Patents

Utilisation de derives de biuret pour hydrater la peau Download PDF

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Publication number
WO2007082908A2
WO2007082908A2 PCT/EP2007/050487 EP2007050487W WO2007082908A2 WO 2007082908 A2 WO2007082908 A2 WO 2007082908A2 EP 2007050487 W EP2007050487 W EP 2007050487W WO 2007082908 A2 WO2007082908 A2 WO 2007082908A2
Authority
WO
WIPO (PCT)
Prior art keywords
skin
alkyl group
linear
biuret
cosmetic
Prior art date
Application number
PCT/EP2007/050487
Other languages
English (en)
Other versions
WO2007082908A3 (fr
Inventor
Xavier Marat
Original Assignee
L'oréal
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
Priority claimed from FR0650207A external-priority patent/FR2896408B1/fr
Application filed by L'oréal filed Critical L'oréal
Publication of WO2007082908A2 publication Critical patent/WO2007082908A2/fr
Publication of WO2007082908A3 publication Critical patent/WO2007082908A3/fr

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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61Q19/007—Preparations for dry skin

Definitions

  • the present invention relates to the use of biuret and derivatives thereof as skin moisturizer.
  • the stratum corneum which forms the interface with the dehydrating external environment, serves especially to retard the excessive water loss from the deeper layers of the epidermis.
  • the stratum corneum also protects against mechanical attack and the passage of chemical products and foreign microorganisms. It also constitutes the first line of defence against UV radiation.
  • the stratum corneum which is 10 ⁇ m thick, is composed of vertically stacked corneocytes surrounded by a matrix of lipid-rich membranes. Thus, it is a two- compartment system that may be compared to a brick wall, composed of nuclear cells (the "bricks") and of intercellular lamellar membranes (the “cement").
  • Urea is one of the ingredients widely used in moisturizing formulations. However, it can greatly modify the skin barrier by increasing the transepidermal water loss (TWL) , which significantly reduces the barrier function of the stratum corneum.
  • TWL transepidermal water loss
  • Glycerol another reference active agent in this field, has the drawback of making the formulations tacky when it is used at high concentration.
  • biuret derivatives of general formula (I) described below are good moisturizers and have a beneficial effect in terms of elasticity of the stratum corneum.
  • one subject of the present invention is the cosmetic (non-therapeutic) use of the compounds of general formula (I) :
  • R 1 , R 2 and R 3 represent, independently of each other, a hydrogen atom or a linear (Ci-Ci 0 ) alkyl group, preferably a linear (Ci-C 4 ) alkyl group, and preferentially a linear (Ci-C 2 ) alkyl group, or a branched (C 3 -Ci 0 ) alkyl group, or a C 6 -Ci 2 aryl group, optionally substituted with one or more (especially 1 to 5) groups chosen from -OR 4 , -NR 5 R 6 , -SiR 7 R 8 R 9 , -COOR 4 , -OCOR 4 and fluorine,
  • R 4 representing a hydrogen atom or a linear Ci-Ci 0 or branched C 3 -C 10 alkyl group
  • - R 5 , R 6 and R 7 representing, independently of each other, a hydrogen atom or a linear Ci-Ci 0 or branched C 3 -Ci 0 alkyl group, optionally substituted with a group -0R 4 -0 or di (Ci-Ci 0 ) alkylamino;
  • - R 7 , R 8 and R 9 represent, independently of each other, a linear Ci-Ci 0 or branched C 3 -Ci 0 alkyl or -OR 4 group,- and also the cosmetically acceptable salts thereof, solvates thereof such as hydrates, and isomers thereof, as skin moisturizers.
  • a subject of the present invention is also a cosmetic process for moisturizing dry skin, comprising the application to the dry skin of at least one cosmetic composition comprising a compound of formula (I) as defined above.
  • R 1 , R 2 and R 3 represent, independently of each other:
  • - a hydrogen atom - a linear (Ci-Ci 0 ) alkyl group, preferably a linear (Ci-C 4 ) alkyl group, and preferentially a linear (Ci-C 2 ) alkyl group, or a branched (C 3 -Ci 0 ) alkyl group, optionally substituted with one or more (especially 1 to 5) -OH groups.
  • alkyl means a hydrocarbon-based chain.
  • alkyl groups that are suitable for use in the invention, mention may be made especially of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, -CH 2 - t-butyl, pentyl, n-hexyl, heptyl, octyl, nonyl and decyl groups .
  • Patent application FR-A-2 452 925 describes a pharmaceutical composition containing substituted biuret derivatives with hypotensive, sedative or anti-convulsive action.
  • Patents US 3 149 338 and BE 592 793 describe hair compositions containing substituted biuret derivatives.
  • Patent application RU-A-2 041 203 describes the use of 1 , 5-bis (2-hydroxyethyl) biuret in polymer preparation. The article by Zmiteck. J. et al . "The synthesis and reactions of N-cyano-o-methylpseudoureas" , Organic Preparations and Procedures Int., 23(6), 721-728 (1191) describes monosubstituted biuret compounds.
  • the compounds of formula (I) may be prepared by performing the synthetic processes described in the abovementioned documents.
  • the salts that are acceptable for the use of the compounds described in the present invention comprise conventional non-toxic salts of the said compounds, such as those formed from organic or mineral acids .
  • examples that may be mentioned include the salts of mineral acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid or boric acid.
  • the neutralization of the acid group (s) may be performed with a mineral base, such as LiOH, NaOH, KOH,
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may be made especially of 2-amino-
  • solvates that are acceptable for the use of the compounds described in the present invention comprise conventional solvates such as those formed during the final step of preparation of the said compounds due to the presence of solvents.
  • solvates due to the presence of water or of linear or branched alcohols, for instance ethanol or isopropanol collates the compounds that may preferably be used in the context of the present invention.
  • compositions in which the compounds (I) may be used are useful for non-therapeutic skincare and/or for skin makeup. They are in particular useful for moisturizing the skin, especially the skin of the face, the neck or the body (in particular the legs, arms, feet, trunk and chest) .
  • these signs of disorder of skin moisturization are preferably independent of irritation caused by the skin coming into contact with a bleaching agent, especially a chlorinated bleaching agent, for example a hypochlorite-based agent.
  • compositions for the use according to the invention are preferably formulated under non-alkaline conditions, and even more preferably at a pH close to that of the skin, for example at a pH of between 5 and 6.
  • the compounds of formula (I) may be present in the cosmetic compositions in contents ranging from 0.01% to 20%, preferably from 0.01% to 15% and even more preferably from 0.1% to 10% by weight relative to the total weight of the cosmetic composition.
  • compositions for the use according to the invention contain a physiologically acceptable medium, i.e. a medium that is compatible with the skin.
  • This physiologically acceptable medium may consist more particularly of water and optionally of a physiologically acceptable organic solvent chosen, for example, from lower alcohols containing from 1 to 8 carbon atoms and in particular from 1 to 6 carbon atoms, for instance ethanol, isopropanol, propanol or butanol; polyethylene glycols containing from 6 to 80 ethylene oxide units and polyols, for instance propylene glycol, isoprene glycol, butylene glycol, glycerol and sorbitol.
  • a physiologically acceptable medium may consist more particularly of water and optionally of a physiologically acceptable organic solvent chosen, for example, from lower alcohols containing from 1 to 8 carbon atoms and in particular from 1 to 6 carbon atoms, for instance ethanol, isopropanol, propanol or butanol; polyethylene glycols containing from 6 to 80
  • compositions for the use according to the invention may be in any galenical form conventionally used for topical application and especially in the form of aqueous or aqueous-alcoholic solutions, oil-in-water
  • compositions (0/W) emulsions, water-in-oil (W/O) emulsions or multiple emulsions (triple: W/O/W or 0/W/O) , aqueous gels, or dispersions of a fatty phase in an aqueous phase with the aid of spherules, these spherules possibly being polymer nanoparticles such as nanospheres and nanocapsules or lipid vesicles of ionic and/or nonionic type (liposomes, niosomes or oleosomes) .
  • These compositions are prepared according to the usual methods .
  • compositions for the use according to the invention may be more or less fluid and may have the appearance of a white or coloured cream, an ointment, a milk, a lotion, a serum, a paste or a mousse. They may optionally be applied to the skin in aerosol form. They may also be in solid form, for example in stick form.
  • composition used according to the invention comprises an oily phase
  • it preferably contains at least one oil. It may also contain other fatty substances .
  • oils that may be used in the composition of the invention examples include: - hydrocarbon-based oils of animal origin, such as perhydrosqualene; hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil; synthetic esters and ethers, especially of fatty acids, for instance the oils of formulae R1COOR2 and R1OR
  • the other fatty substances that may be present in the oily phase are, for example, fatty acids containing from 8 to 30 carbon atoms, for instance stearic acid, lauric acid, palmitic acid and oleic acid; waxes, for instance lanolin wax, beeswax, carnauba wax or candelilla wax, paraffin wax, lignite wax or microcrystalline waxes, ceresin or ozokerite, and synthetic waxes, for instance polyethylene waxes and Fischer-Tropsch waxes; silicone resins such as trifluoromethyl-Cl-4-alkyl dimethicone and trifluoropropyl dimethicone; and silicone elastomers, for instance the products sold under the name KSG by the company Shin-Etsu, under the name Trefil, BY29 or EPSX by the company Dow Corning, or under the name Gransil by the company Grant Industries.
  • fatty acids containing from 8 to 30 carbon atoms for instance stearic acid
  • fatty substances may be chosen in a varied manner by a person skilled in the art so as to prepare a composition having the desired properties, for example in terms of consistency or texture.
  • the composition for the use according to the invention is a water-in-oil (W/0) or oil-in-water (O/W) emulsion.
  • W/0 water-in-oil
  • O/W oil-in-water
  • the proportion of the oily phase of the emulsion may range from 5% to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.
  • the emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic and nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier .
  • the emulsifiers are chosen in an appropriate manner according to the emulsion to be obtained (W/0 or 0/W) emulsion.
  • the emulsifier and the co-emulsifier are generally present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight relative to the total weight of the composition.
  • emulsifiers examples include dimethicone copolyols such as the mixture of cyclomethicone and of dimethicone copolyol sold under the name DC 5225 C by the company Dow Corning, and alkyl dimethicone copolyols such as the laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning and the cetyl dimethicone copolyol sold under the name Abil EM 90R by the company Goldschmidt .
  • surfactants for W/0 emulsions that may also be used include a crosslinked elastomeric solid organopolysiloxane comprising at least one oxyalkylene group, such as those obtained according to the procedure of
  • emulsifiers examples include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan,- oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters,- oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alkyl ethers; sugar esters, for instance sucrose stearate; and mixtures thereof such as the mixture of glyceryl stearate and of PEG-40 stearate.
  • nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan,- oxyalkylenated (oxyethyl
  • the cosmetic or dermatological composition for the use according to the invention may also contain adjuvants that are common in cosmetics or dermatology, such as gelling agents, film-forming polymers, preserving agents, solvents, fragrances, fillers, UV-screening agents, bactericides, odour absorbers, dyestuffs, plant extracts and salts.
  • adjuvants that are common in cosmetics or dermatology, such as gelling agents, film-forming polymers, preserving agents, solvents, fragrances, fillers, UV-screening agents, bactericides, odour absorbers, dyestuffs, plant extracts and salts.
  • the amounts of these various adjuvants are those conventionally used in the field under consideration, for example from 0.01% to 20% of the total weight of the composition. Depending on their nature, these adjuvants may be introduced into the fatty phase and/or into the aqueous phase .
  • the compounds of formula (I) may be combined with each other or with other skin moisturizers not in accordance with formula (I) and/or with at least one other cosmetic active agent.
  • Additional cosmetic active agents include active agents that act on the barrier function of the skin, active agents that promote skin moisturization and desquamating agents.
  • the term "desquamating agent” means any compound capable of acting: - either directly on desquamation by promoting exfoliation, such as ⁇ -hydroxy acids, in particular salicylic acid and derivatives thereof (including 5-n-octanoylsalicylic acid); ⁇ -hydroxy acids, such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; urea,- gentisic acid; oligofucoses; cinnamic acid; extract of Saphora japonica; resveratrol; or on the enzymes involved in desquamation or corneodesmosome degradation, such as glycosidases, stratum corneum chymotryptic enzyme (SCCE) or other proteases (trypsin, chymotrypsin-like) .
  • SCCE stratum corneum chymotryptic enzyme
  • mineral salt chelating agents EDTA; N-acyl- N, N' ,N' -ethylenediaminetriacetic acid; aminosulfonic compounds and in particular N- (2-hydroxyethyl )- piperazine-N' -2-ethanesulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives; derivatives of oc-amino acids of glycine type (as described in EP-O 852 949, and also sodium methyl glycine diacetate sold by BASF under the trade name "TRILON M"); honey,- sugar derivatives such as O-octanoyl-6-D-maltose and N-acetylglucosamine .
  • the active agents acting on the barrier function of the skin, or promoting skin moisturization mention may be made of : either compounds that act on the barrier function, in order to maintain the moisturization of the stratum corneum, or occlusive compounds, in particular ceramides, sphingoid-based compounds, lecithins, glycosphingolipids, phospholipids, cholesterol and derivatives thereof, phytosterols (stigmasterol , ⁇ -sitosterol or campesterol) , essential fatty acids, 1, 2-diacylglycerol, 4-chromanone, pentacyclic triterpenes such as ursolic acid, petroleum jelly and lanolin,- or compounds that directly increase the water content of the stratum corneum, such as threalose and derivatives thereof, hyaluronic acid and derivatives thereof, glycerol, pentanediol, sodium pidolate, serine, xylitol, sodium lactate, polyglyceryl
  • composition may be in the form of a non-therapeutic care and/or makeup product, and also in the form of a lip balm.
  • a subject of the invention is a cosmetic treatment process for moisturizing dry skin, characterized in that it comprises the application to the dry skin of at least one cosmetic composition comprising at least one compound of formula (I) as defined above or a mixture thereof in all proportions .
  • the invention relates to the use of a compound of formula (I) as defined above or of a mixture thereof for the preparation of a dermatological composition for moisturizing the skin and more particularly for treating dryness of the skin or for treating dry skin.
  • Biuret has significant plasticizing moisturizing activity, but which is lower than that of urea and glycerol.
  • a skincare cream having the composition below is prepared:
  • Phase B is heated to about 75 0 C and the ammonium polyacryldimethyltauramide is incorporated therein; the mixture is stirred until a homogeneous gel is obtained.
  • Phase A is heated to about 75 0 C.
  • the emulsion is prepared by incorporating phase A into phase B. - Phase C is incorporated, at 40-45 0 C, and stirring is continued until cooling is complete.
  • a skincare cream having the following composition is prepared:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne l'utilisation cosmétique d'un composé répondant à la formule (I) dans lequel R1, R2 et R3 représentent un atome d’hydrogène ou un groupe alkyle en C1 à C10 ou un groupe aryle en C6 à C12, qui est éventuellement substitué, et également leurs sels acceptables sur le plan cosmétique, leurs solvates et leurs isomères, en tant qu’hydratants cutanés.
PCT/EP2007/050487 2006-01-20 2007-01-18 Utilisation de derives de biuret pour hydrater la peau WO2007082908A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0650207 2006-01-20
FR0650207A FR2896408B1 (fr) 2006-01-20 2006-01-20 Utilisation de derives du biuret pour hydrater la peau
US76138706P 2006-01-24 2006-01-24
US60/761,387 2006-01-24

Publications (2)

Publication Number Publication Date
WO2007082908A2 true WO2007082908A2 (fr) 2007-07-26
WO2007082908A3 WO2007082908A3 (fr) 2007-11-01

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB907188A (en) * 1959-07-07 1962-10-03 Colgate Palmolive Co Hair preparations
US3925957A (en) * 1972-11-24 1975-12-16 Lever Brothers Ltd Toothpastes
FR2452925A1 (fr) * 1979-03-31 1980-10-31 Taiho Pharmaceutical Co Ltd Composition pharmaceutique contenant un compose 1,3-5 substitue du biuret
WO2002083136A1 (fr) * 2001-04-17 2002-10-24 Process & Industrial Design Consultants Ltd Compositions therapeutiques contenant des acides amino sulfoniques et leurs utilisations

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB907188A (en) * 1959-07-07 1962-10-03 Colgate Palmolive Co Hair preparations
US3925957A (en) * 1972-11-24 1975-12-16 Lever Brothers Ltd Toothpastes
FR2452925A1 (fr) * 1979-03-31 1980-10-31 Taiho Pharmaceutical Co Ltd Composition pharmaceutique contenant un compose 1,3-5 substitue du biuret
WO2002083136A1 (fr) * 2001-04-17 2002-10-24 Process & Industrial Design Consultants Ltd Compositions therapeutiques contenant des acides amino sulfoniques et leurs utilisations

Also Published As

Publication number Publication date
WO2007082908A3 (fr) 2007-11-01

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