EP2091504A2 - Utilisation de particules hybrides colorées ou fluorescentes pour traiter des fibres de kératine - Google Patents

Utilisation de particules hybrides colorées ou fluorescentes pour traiter des fibres de kératine

Info

Publication number
EP2091504A2
EP2091504A2 EP07857548A EP07857548A EP2091504A2 EP 2091504 A2 EP2091504 A2 EP 2091504A2 EP 07857548 A EP07857548 A EP 07857548A EP 07857548 A EP07857548 A EP 07857548A EP 2091504 A2 EP2091504 A2 EP 2091504A2
Authority
EP
European Patent Office
Prior art keywords
use according
keratin fibres
coloured
composition
dyeing
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP07857548A
Other languages
German (de)
English (en)
Inventor
Frédéric Guerin
Murat Quadir
Luc Gourlaouen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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 FR0655468A external-priority patent/FR2909869B1/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP2091504A2 publication Critical patent/EP2091504A2/fr
Withdrawn legal-status Critical Current

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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon 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
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers

Definitions

  • the invention relates to the use of coloured or fluorescent organosilane particles in cosmetics, especially in the field of hair dyeing.
  • - direct dyeing or semi-permanent dyeing consists in providing colour via a coloured molecule that is adsorbed onto the surface of the keratin fibres and/or that penetrates by diffusion into the surface layers thereof.
  • the leave-on times are generally fairly short and the mild dyeing conditions preserve the integrity of the keratin fibres, but the colorations obtained via this mode of dyeing show poor wash-fastness and fade out after only four or five shampoo washes. Furthermore, the ranges of shades obtained are generally limited;
  • - oxidation dyeing or permanent dyeing uses the oxidative condensation of colourless or weakly coloured molecules, known as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols or heterocyclic compounds in the presence of an oxidizing agent.
  • oxidation bases such as ortho- or para-phenylenediamines, ortho- or para-aminophenols or heterocyclic compounds
  • This reaction leads to the formation of coloured polymer compounds in the keratin fibres.
  • the main advantage of oxidation dyeing lies in the longevity of the colorations obtained, in particular in the resistance to washing and to external agents such as light, bad weather, permanent waving, perspiration and rubbing, and also in the production of a wide range of shades.
  • the chemical dyeing conditions such as the pH and an oxidizing medium, result in degradation of the keratin fibres.
  • this mode of dyeing requires relatively long leave-on times.
  • sol-gel particles in which agents are encapsulated.
  • document WO 2004/081 222 describes sol-gel particles in which dyes or fluorescent dyes are encapsulated, these particles possibly being used in haircare products or medical products .
  • the problem lies in the fact that since the particles are porous, it is found that, when these particles are used in cosmetic compositions, migration of the dyes outside the particles is observed, which firstly limits the gains in stability, especially with respect to light, that might be obtained, and secondly reduces the harmlessness of the system.
  • Hybrid sol-gel nanoparticles constituted of a colloidal silica, in which this silica is covalently bonded to fluorescent dyes, are moreover known.
  • Such nanoparticles may also have a core/shell structure, the core being obtained from a standard alkoxysilane in sol-gel synthesis.
  • Such particles are described, for example, in “Multicolour FRET silica nanoparticles by single wavelength excitation”, Lin Wang and Weihong Tan, Nano Letters, 2006, vol. 6, No 1, 84-88; in “Bright and stable core-shell fluorescent silica nanoparticles", Nano Letters, 2005, vol. 5, No 1, 113- 117. These nanoparticles are recommended for use in biological probes by virtue of their very strong fluorescent power.
  • the aim of the present invention is to provide a novel system for dyeing keratin fibres that does not have the drawbacks of the existing systems.
  • the aim of the present invention is to provide a novel dye system that simultaneously has the advantages of harmlessness, stability and intensity of the colorations obtained, and gentleness on the keratin fibre, and which allows a wide range of shades to be obtained.
  • This aim is achieved with the present invention, one subject of which is the use for dyeing keratin fibres, especially the hair, of hybrid particles obtained from an organosilane compound bearing a coloured species.
  • a subject of the present invention is also a process for dyeing keratin fibres, especially the hair, which comprises the application to the fibres of a composition comprising, in a cosmetic medium, hybrid particles obtained from an organosilane compound bearing a coloured species.
  • the particles that are useful for the present invention make it possible to obtain, depending on the coloured species attached to the organosilane, fast dyeing or optical lightening of keratin fibres. Moreover, the present invention makes it possible to obtain fast dyeing or optical lightening without degradation of the keratin fibres.
  • optical lightening means a visual lightening effect on naturally or artificially coloured keratin fibres, without using compounds that destroy the natural or artificial coloured pigments present in the keratin fibres .
  • organosilane bearing a coloured species means that the coloured species is connected via a covalent bond to the silicon of the organosilane.
  • the coloured species may be any radical derived from direct dyes, pigments or fluorescent dyes that are standard in the field of dyeing. Examples that may be mentioned include pigments, direct dyes and fluorescent dyes conventionally used in hair dyeing. Mention may be made especially of dyes of the nitrobenzene, anthraquinone, nitropyridine, azo, cationic azo, xanthene, acridine, azine and nitrobenzene triarylmethane type, or natural dyes.
  • benzene direct dyes that may be mentioned, in a non-limiting manner, are the following compounds: 1, 4-diamino-2-nitrobenzene, l-amino-2-nitro-4- ⁇ - hydroxyethylaminobenzene, l-amino-2-nitro-4-bis ( ⁇ - hydroxyethyl) -aminobenzene, 1, 4-bis ( ⁇ -hydroxyethyl- amino) -2-nitrobenzene, l- ⁇ -hydroxyethylamino-2-nitro-4- bis ( ⁇ -hydroxyethylamino) benzene, 1- ⁇ -hydroxyethylamino- 2-nitro-4-aminobenzene, l- ⁇ -hydroxyethylamino-2-nitro- 4- (ethyl) ( ⁇ -hydroxyethyl) aminobenzene, l-amino-3- methyl-4- ⁇ -hydroxyethylamino-6-nitrobenzene, l-amino-2- nitro-4- ⁇ - ⁇ -
  • ⁇ -dihydroxypropylamino-4-trifluoromethyl- 2-nitrobenzene 1- ⁇ -hydroxyethylamino-4-trifluoro- methy1-2-nitrobenzene, l- ⁇ -hydroxyethylamino-3-methyl- 2-nitrobenzene, l- ⁇ -aminoethylamino-5-methoxy-2-nitro- benzene, 1-hydroxy-2-chloro-6-ethylamino-4-nitro ⁇ benzene, l-hydroxy-2-chloro-6-amino-4-nitrobenzene, 1- hydroxy-6-bis ( ⁇ -hydroxyethyl) amino-3-nitrobenzene, 1- ⁇ - hydroxyethylamino-2-nitrobenzene, 1-hydroxy-4- ⁇ - hydroxyethylamino-3-nitrobenzene .
  • azo direct dyes that may be mentioned are the cationic azo dyes described in patent applications WO 95/15144, WO 95/01772 and EP-714 954, the content of which forms an integral part of the invention.
  • dyes 1, 3-dimethyl-2- [ [4- (dimethylamino) phenyl ] azo] -lH-imidazolium chloride, 1, 3-dimethyl-2- [ (4-aminophenyl) azo] -lH-imidazolium chloride, l-methyl-4- [ (methylphenylhydrazono) methyl] - pyridinium methyl sulfate.
  • Disperse Red 15 Solvent Violet 13
  • Acid Violet 43 Disperse Violet 1
  • Disperse Violet 4 Disperse Blue 1
  • Disperse Violet 8 Disperse Blue 3
  • Disperse Red 11 Acid Blue 62, Disperse Blue 7, Basic Blue 22, Disperse Violet 15, Basic Blue 99
  • fluorescent dyes that may be mentioned include the fluorescent dyes mentioned in the "Molecular Probes Handbook of Fluorescent Probes and Research Chemical", 6th edition, R. P. Haugland, ed. (1996) or in Ullmann' s Encyclopaedia of Industrial Chemistry, 2004 release, 7th edition, in the chapter "Fluorescent Dyes”.
  • fluorescent dyes are aromatic or heteroaromatic compounds such as pyrenes, anthracenes, naphthalenes, acridines, indoles, benzindoles, ketopyrroles, oxazoles, benzoxazoles, diazoles, methines, carbocyanins, carbostyryls, porphyrins, salicylates, anthranilates, azulenes, perylenes, pyrazines, pyridines, quinolines, coumarins and xanthenes .
  • aromatic or heteroaromatic compounds such as pyrenes, anthracenes, naphthalenes, acridines, indoles, benzindoles, ketopyrroles, oxazoles, benzoxazoles, diazoles, methines, carbocyanins, carbostyryls, porphyrins, salicylates, anthranilates, azulenes, pery
  • the organosilanes may be represented by the general formula R( 4 - n) SiX n in which X represents a hydrolysable group such as methoxy, ethoxy or 2-methoxyethoxy; R is a monovalent organic radical containing from 1 to 12 carbon atoms possibly containing functional organic groups capable of reacting with the coloured species, such as mercapto, epoxy, acrylyl, methacrylyl or amino; and n is an integer ranging from 0 to 4, and preferably n is equal to 3, with the condition that at least one organosilane used to form the particles comprises a group R containing a functional organic group capable of reacting with the coloured species.
  • silanes capable of reacting to obtain a silane bearing a coloured species mention may be made of 3-amino- propyltriethoxysilane and 3-mercaptopropyltriethoxy- silane .
  • the hybrid particles are hybrid particles whose coloured species is fluorescent.
  • the hybrid particles are covered with a silica sol-gel shell obtained from alkoxysilane, preferably trialkoxysilanes or tetraalkoxysilanes .
  • the particles may be constituted, for example, of a homogeneous core and of one or more layers covering this core and forming the shell, these layers possibly being of different nature.
  • the hybrid particles are fluorescent particles comprising a core constituted of organosilane (s) bearing fluorescent compound (s) and a silica shell.
  • the core of the particles may then be obtained by reacting one or more fluorescent dyes with a reactive organosilane capable of reacting with this or these fluorescent dye(s) .
  • the core is then obtained via a condensation reaction of one or more (organo) alkoxy- silanes.
  • These (organo) alkoxysilanes may make it possible to obtain one or more layers constituting the shell, these layers possibly having particular different properties as a function of the
  • (organo) alkoxysilane used the thickness of the shell, the continuity of the shell on the core, and the ratio of the thickness of the shell to the core.
  • the size of the particles that are useful in the present invention may vary widely. However, these particles are generally nanoparticles, especially nanoparticles with a number-average diameter ranging from 1 to 100 nm and preferably between 1 and 50 nm. In a particularly preferred manner, these particles are nanoparticles with a diameter of between 1 and 20 nm.
  • these particles are monodisperse .
  • the size and the size distribution are determined by electron microscopy (SEM) .
  • the hybrid particles that are useful in the present invention are known particles of the art obtained via a sol/gel route. For example, these particles are described in the Nano Letters articles mentioned previously and also in patent application US 2004/0 101 822. For further details regarding the nature of the precursors and the reaction mechanisms in sol-gel processes, reference may be made to the book "Sol Gel Science” published by CJ. Brinker and G. W. Scherer, Academic Press publications (ISBN 0-12-134970- The hybrid particles are generally obtained via a sol- gel process that is performed using (organo) silanes . These organosilanes may be represented by the general formula R( 4 - n) SiX n as defined above.
  • TRITC reactive fluorescent dye tetramethylrhodamine isothiocyanate
  • One or two steps may be performed depending on whether or not the organosilane bearing a coloured species is isolated.
  • this first particle that will become the core is reacted with an alkoxysilane, preferably a tetraalkoxysilane such as tetraethyl orthosilicate, which, via a condensation reaction, will form a dense silica shell around the fluorescent core.
  • an alkoxysilane preferably a tetraalkoxysilane such as tetraethyl orthosilicate, which, via a condensation reaction, will form a dense silica shell around the fluorescent core.
  • TRITC and 3-aminopropyltriethoxysilane are reacted via an addition reaction in a mole ratio of 1:50 in a moisture-free medium.
  • the product of this reaction is then placed in a reactor in the presence of aqueous ammonia, water and solvent. The reaction is left to proceed overnight. After this reaction, tetraethyl orthosilicate is introduced into the reaction medium in order to form the silica shell.
  • homogeneous particles may be obtained by simultaneously reacting via co-condensation all the reagents described above.
  • the particles may also be covered with one or more additional organic and/or mineral layers, preferably having affinity for the hair.
  • organic layers that may be mentioned include the layers obtained with polyethylene glycol, polyurethane, dextrin, polyacrylic, polyvinylpyrrolidone, polyvinyl- caprolactone or a mixture of these materials.
  • mineral layers examples include the layers obtained with alumina, silica or clay, or a mixture of these materials. These layers may be obtained via the sol-gel process using organosilane .
  • the composition contains a cosmetic medium that is suitable for dyeing, also known as a dye support, and generally consisting of water or of a mixture of water and of at least one organic solvent.
  • organic solvents include Ci-C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers, for instance 2- butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof .
  • the concentration of hybrid particles in the compositions used according to the invention preferably ranges from 0.001% to 99%, even more preferentially from 0.005% to 50% and ideally from 0.01% to 20%.
  • the solvents are preferably present in proportions preferably of between 1% and 40% by weight approximately, and even more preferentially between 5% and 30% by weight approximately, relative to the total weight of the dye composition.
  • the dye composition in accordance with the invention may also contain various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance volatile or non-volatile, modified or unmodified silicones, film-forming agents, ceramides, preserving agents and opacifiers .
  • the above adjuvants are generally present in an amount for each of them of between 0.01% and 20% by weight relative to the weight of the composition.
  • composition according to the present invention preferably comprises, in addition to the nanoparticles, a surfactant or a thickening polymer.
  • surfactants and polymers may be of nonionic, anionic, cationic or amphoteric nature.
  • the amounts of surfactants and/or of thickening polymer present in the composition according to the invention may range from 0.01% to 40% and preferably from 0.5% to 30% of the total weight of the composition.
  • the pH of the dye composition in accordance with the invention is generally between 3 and 12 approximately and preferably between 5 and 11 approximately. It may be adjusted to the desired value by means of acidifying or basifying agents usually used in the dyeing of keratin fibres, or alternatively using standard buffer systems .
  • acidifying agents examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • mineral or organic acids for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • basifying agents examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines such as monoethanolamine, diethanolamine, triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (II) below:
  • R a , R b , R c and R d which may be identical or different, represent a hydrogen atom or a Ci-C 4 alkyl or Ci-C 4 hydroxyalkyl radical.
  • the dye composition according to the invention may be in various forms, such as in the form of liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibres, and especially human hair.
  • Another subject of the invention is a process for treating keratin fibres, and in particular human keratin fibres such as the hair, which comprises the application to the fibres of a composition according to the present invention.
  • the process of the invention is a process for dyeing keratin fibres.
  • the composition of the invention may be applied to wet or dry fibres.
  • the application may be followed by a step of washing and/or rinsing the keratin fibres.
  • the process of the invention when it is applied to naturally or artificially coloured dark hair, for example hair with a tone depth of greater than or equal to 4 and preferably greater than or equal to 6, makes it possible to obtain optical lightening of the hair.
  • tone is based on the classification of natural shades, one tone separating each shade from the one immediately following or preceding it. This definition and the classification of natural shades are well known to hairstyling professionals and are published in the book “Sciences des.s capillaires [Hair treatment sciences]" by Charles Zviak, 1988, published by Masson, pp. 215 and 278.
  • an aqueous composition containing 5% of alkylpolyglucoside and 0.5% of fluorescent red core/shell nanoparticles (TRITC) prepared according to the procedure described in Examples 1 and 3 (pp. 12-13) of patent US 2004/101 822, may be applied at room temperature to a lock of natural grey hair containing 90% white hairs. After the lock of hair treated in this way has been drained and dried, a red coloration of the lock of hair can be seen.
  • TRITC fluorescent red core/shell nanoparticles

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention porte sur l'utilisation, pour colorer des fibres de kératine, notamment les cheveux, de particules hybrides obtenues à partir d'un composé organosilane portant une espèce colorée. La présente invention porte également sur un procédé de coloration de fibres de kératine, notamment les cheveux, qui comprend l'application sur les fibres d'une composition comprenant, dans un milieu cosmétique, des particules hybrides obtenues à partir d'un composé organosilane portant une espèce colorée. Les particules qui sont utiles pour la présente invention permettent d'obtenir, en fonction de l'espèce colorée liée à l'organosilane, une teinture rapide ou un éclaircissement optique des fibres de kératine.
EP07857548A 2006-12-13 2007-12-13 Utilisation de particules hybrides colorées ou fluorescentes pour traiter des fibres de kératine Withdrawn EP2091504A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0655468A FR2909869B1 (fr) 2006-12-13 2006-12-13 Utilisation de particules hybrides colorees ou fluorescentes pour le traitement des fibres keratiniques
US87841807P 2007-01-04 2007-01-04
PCT/EP2007/063901 WO2008071772A2 (fr) 2006-12-13 2007-12-13 Utilisation de particules hybrides colorées ou fluorescentes pour traiter des fibres de kératine

Publications (1)

Publication Number Publication Date
EP2091504A2 true EP2091504A2 (fr) 2009-08-26

Family

ID=39512133

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07857548A Withdrawn EP2091504A2 (fr) 2006-12-13 2007-12-13 Utilisation de particules hybrides colorées ou fluorescentes pour traiter des fibres de kératine

Country Status (3)

Country Link
EP (1) EP2091504A2 (fr)
JP (1) JP2010513247A (fr)
WO (1) WO2008071772A2 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040101822A1 (en) * 2002-11-26 2004-05-27 Ulrich Wiesner Fluorescent silica-based nanoparticles
WO2004081222A2 (fr) * 2003-03-14 2004-09-23 Sol-Gel Technologies Ltd. Microparticules et nanoparticules d'encapsulation d'agents, procedes de preparation de celles-ci, et produits contenant celles-ci
FR2853229B1 (fr) * 2003-04-01 2009-06-12 Oreal Procede de coloration pour matieres keratiniques humaines avec effet eclaircissant, compose fluorescent particulier et composition le comprenant
FR2877217B1 (fr) * 2004-11-03 2007-01-26 Oreal Utilisation de composes de type organosilane en teinture des fibres keratiniques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008071772A3 *

Also Published As

Publication number Publication date
WO2008071772A3 (fr) 2008-10-02
JP2010513247A (ja) 2010-04-30
WO2008071772A2 (fr) 2008-06-19

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