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
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/23—Sulfur; Selenium; Tellurium; Compounds 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
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/24—Phosphorous; Compounds 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
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/25—Silicon; Compounds 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
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/26—Aluminium; Compounds 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
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/27—Zinc; Compounds thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B82—NANOTECHNOLOGY
  • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
  • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/81—Preparation or application process involves irradiation

Definitions

• the present invention relates to a new cosmetic composition, in particular for make-up, comprising as pigment fluorescent nanoparticles consisting of semiconductor, called “quantum dots” (“quantum dots” in English). It also relates to a process for manufacturing such a composition.
• make-up compositions such as in particular mascaras, blushes, eyeshadows, lipsticks, nail varnishes or lacquers consist of an appropriate cosmetic vehicle and of various coloring agents intended for impart a certain color to the compositions before and / or after their application to the skin, lips and / or integuments.
• coloring agents such as lacquers, mineral pigments or pearlescent pigments. Lacquers allow the production of bright colors. However, most of these lacquers are not very resistant to light, temperature and / or pH. Some also have the disadvantage of unsightly staining the skin after application, by disgorging the dye.
• the mineral pigments in particular the mineral oxides, are very stable, but give rather dull and pale colors. Pearlescent pigments make it possible to obtain varied, but never intense, colors with iridescent effects but most often quite weak, and above all the color effect is mainly visible at a single given angle corresponding to specular reflection.
• the method according to US 6,319,426, making it possible to obtain fluorescent nanoparticles having a narrow particle size distribution comprises covering the nanoparticle with a hydrophobic ligand.
• These fluorescent nanoparticles therefore have a low affinity for water and are therefore difficult to incorporate into hydrophilic media.
• An object of the present invention is therefore to provide a hydrophilic cosmetic composition which comprises, as pigment, fluorescent nanoparticles and which overcomes the aforementioned drawbacks.
• Another object of the invention is a process for manufacturing such cosmetic compositions.
• compositions according to the invention have a certain number of interesting characteristics.
• the wavelength of the light emitted by these particles being a function of the particle size, it can be varied easily over the entire spectrum. It is therefore possible to obtain different colors with particles of identical chemical nature. Thus, it overcomes the compatibility problems between the basic cosmetic composition and the different pigments.
• compositions comprising fluorescent nanoparticles of different sizes and / or having a wide particle size distribution to provide compositions of compound color.
• compositions comprising single size fluorescent nanoparticles having a narrow particle size distribution will be preferred, which will provide a sharper and more intense color.
• pigments is understood to mean particles insoluble in the medium that constitutes the cosmetic composition, that is to say dispersed or solid in one of the phases of said medium and serving for coloring (creation or modification of shades color) and / or the opacity of said composition.
• the fluorescent nanoparticles capable of being incorporated as a pigment in the cosmetic compositions comprise semiconductor compounds, preferably cosmetically acceptable.
• cosmetically acceptable therefore means compounds which are not toxic to humans when applied to the skin, the eyelashes, the nails or the hair.
• These semiconductors include the cosmetically acceptable compounds of group IV of the periodic system of elements, of group II-
• the semiconductor can also comprise mixtures of these semiconductors such as in particular CdSe / CdS,
• GaAs, GaN, GaP, GaSb, InGaAs, InP, InN, InSb, InAs, AlAs, AIP, AlSb and AIS are preferred.
• Ge, Pb and Si are particularly suitable.
• the nanoparticle comprises a semiconductor encapsulated in one or more other materials. It then has a structure called core / shell type (the shell can be multilayer).
• the shell also includes one or more semiconductors (as for example in the case of a CdSe core encapsulated in ZnSe then ZnS, see the article by P. Reiss (Reiss, P ., S. Carayon, et al. (2003).
• HgTe GaAs, GaN, GaP, GaSb, InGaAs, InP, InN, InSb, InAs, AlAs, AIP, AlSb, AIS, PbS, PbSe, Ge, Si, or a mixture thereof.
• the shell of the fluorescent nanoparticles also comprises a semiconductor. It can then be in particular ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgS, MgSe, GaAs, GaN, GaP, GaAs, GaSb, InAs, InN, InP, InSb, AlAs, AIN, AIP, AlSb, or one of their mixtures.
• the encapsulation can be carried out for example by epitaxial growth, as described for example in Peng et al., J.Am.Chem.Soc, (1997) 119: 7019-7029.
• the fluorescent nanoparticles have an average size of between 1.5 and 50 nm, preferably between 2 and 40 nm.
• the core preferably has an average size of between 1.5 and 10 nm and the encapsulation layer (shell) a thickness of 1 to 10 monolayers.
• the size of these fluorescent nanoparticles prevents any migration across the skin barrier.
• the size can be controlled during their manufacture, for example using the methods described in the following patents: US 5,751,018, US 5,505,928, US 5,262,357.
• the emission spectrum of fluorescent nanoparticles can be controlled by their particle size distribution, their average size and their composition, and - if necessary - using encapsulation layers. The adjustment of these parameters then makes it possible to obtain a spectrum corresponding to the coloring which it is desired to impart to the cosmetic composition.
• the fluorescent nanoparticles are encapsulated in a specific micelle in order to make them compatible with a hydrophilic medium.
• One or more fluorescent nanoparticles are then encapsulated in a micelle of a size between 5 and 45 nm, which comprises a hydrophilic envelope comprising several hydrophilic parts and a core hydrophobic comprising several hydrophobic parts, each of the hydrophobic parts comprising at least one chain of at least 8 carbon atoms, and each of the parts comprising at least 24 carbon atoms for all of the chains.
• a micelle of a size between 5 and 45 nm which comprises a hydrophilic envelope comprising several hydrophilic parts and a core hydrophobic comprising several hydrophobic parts, each of the hydrophobic parts comprising at least one chain of at least 8 carbon atoms, and each of the parts comprising at least 24 carbon atoms for all of the chains.
• one or more fluorescent nanoparticles previously coated with a hydrophobic ligand are then complexed into a micelle with a size of between 5 and 45 nm, the micelle being formed of a hydrophobic core and a hydrophilic
• the hydrophobic core containing a plurality of hydrophobic groups, the envelope containing a plurality of hydrophilic groups, each hydrophobic group containing at least one chain, each chain comprising at least 8 carbon atoms, the number of carbon atoms for the whole hydrophobic chains of a single hydrophobic group being greater than or equal to 24.
• the hydrophobic group is formed of two carbon chains.
• the hydrophilic group is preferably a polysaccharide such as agarose, dextran, starch, cellulose, amylose or amylopectin. However, it can also be synthetic polymers, such as for example polyethylene glycol and other hydrophilic monomers.
• the micelle is preferably formed from block copolymers and in particular the phospholipids-PEG such as those used in the article published by Dubertret, B., P. Skourides, et al. (2002). "In vivo imaging of quantum dots encapsulated in phospholipid micelles.” Science 298 (5599): 1759-1762.
• the hydrophobic groups Due to the hydrophobic coating of the fluorescent nanoparticles, the hydrophobic groups then orient towards the nanoparticle and the hydrophilic groups towards the outside, thus allowing their solubilization in an aqueous solution.
• These fluorescent micelle nanoparticles also exhibit high stability and they are biocompatible, that is to say non-toxic and having a low non-specific adsorption, in other words, they exhibit little or no aggregation with one another or with d 'other molecules.
• Some cosmetic vehicles are hydrophobic (varnish, lacquers, etc.) and do not require the solubilization of fluorescent nanoparticles in aqueous media.
• the fluorescent nanoparticles are covered hydrophobic ligand or hydrophobic polymers in order to avoid their aggregation and to protect them against any charges present in solution.
• compositions according to the invention comprise, in addition to the fluorescent semiconductor nanoparticles, a cosmetic vehicle.
• This cosmetic vehicle can be monophasic. It is however common in the cosmetic field that the vehicle has two or more phases. In any event, the cosmetic vehicle has a continuous hydrophilic or hydrophobic phase.
• the quantity of fluorescent nanoparticles introduced into the cosmetic vehicle which can be determined by a person skilled in the art, is in particular a function of the destination of the composition; it can range from 0.01% to 50% by weight, preferably from 0.5 to 25% by weight relative to the total weight of the composition.
• compositions according to the invention may be useful in cosmetic products, such as in particular make-up products, for application to the skin, face or body, or cosmetic treatments of the nails, eyelashes, eyebrows, hair, and lips.
• the cosmetic composition is a makeup composition.
• the makeup compositions generally comprise at least one hydrophobic phase. They may however also include a hydrophilic phase, continuous or dispersed. These phases can be in the liquid, gaseous and / or solid state.
• compositions include, for example, nail varnishes, lipsticks, mascara, foundations, blushes, eyeshadows, hairsprays, etc. These compositions then make it possible to obtain very specific visual effects while being capable of providing appropriate care and protection.
• the composition of the invention may be in the form of a product intended to be applied to the skin, both of the body and of the face, the hair, the eyelashes, the eyebrows and the nails.
• the composition according to the invention therefore contains a cosmetically acceptable medium, compatible with all the keratin materials with which it comes into contact.
• the composition may optionally also comprise a surfactant, preferably in an amount of 0 to 30% by weight, preferably of 0.01 to 30% by weight relative to the weight total of the composition.
• a surfactant preferably in an amount of 0 to 30% by weight, preferably of 0.01 to 30% by weight relative to the weight total of the composition.
• the emulsion can be a single or multiple emulsion, in particular a W / O, O / W, W / O / W and O / W / O emulsion. It is understood that the fluorescent nanoparticles can be present in any one or more of these phases.
• the composition may also comprise, in addition, at least one film-forming polymer, in particular for mascaras, eyeliner or hair composition of lacquer type.
• the polymer can be dissolved or dispersed in a cosmetically acceptable medium and optionally combined with at least one coalescing agent and / or at least one plasticizer.
• the composition according to the invention can also comprise a fatty phase, which contains in particular at least one liquid fatty substance and / or at least one fatty substance solid at room temperature and at atmospheric pressure.
• Liquid fatty substances can constitute from 0 to 90%, preferably from 0.01 to 85% by weight relative to the total weight of the fatty phase.
• the solid or pasty fatty substances can be chosen in particular from waxes, gums and their mixtures.
• the composition may contain 0 to 50%, preferably from 0.01 to 40%, and in particular 0.1 to 30% by weight relative to the total weight of the composition of solid or pasty fatty substances.
• composition according to the invention may also comprise from 0 to 30%, preferably from 0.01 to 35% by weight relative to the total weight of the composition of other particles.
• These particles can in particular be a pigment other than fluorescent nanoparticles, nacre or filler. The presence of these other particles makes it possible in particular to cloud the composition.
• composition according to the invention can comprise the ingredients conventionally present in such compositions, such as preservatives, antioxidants, thickeners, perfumes, moisturizers, sun filters, essential oils, extracts vegetables and vitamins.
• the invention provides a process for the preparation of such a cosmetic composition, comprising the steps consisting of: i) supply of the fluorescent nanoparticles; ii) if necessary, prior compatibility treatment of the fluorescent nanoparticles; and iii) introduction of the fluorescent nanoparticles thus treated into a cosmetic vehicle.
• the fluorescent nanoparticles can be incorporated beforehand in one of the other constituents of the cosmetic composition or else in the finished cosmetic vehicle.
• core / shell fluorescent nanoparticles For the formation of core / shell fluorescent nanoparticles, 250 ⁇ l of the solution obtained above (core) was injected into 10 ml of TOPO. After heating to 140 ° C., a solution containing 5 ml of TOP, 100 ⁇ l of diethylzinc and 100 ⁇ l of hexamethyldisilthiane was injected drop by drop. After the injection, the flask was cooled to 90 ° C and kept at this temperature for one hour. The core / shell fluorescent nanoparticles were precipitated with methanol and suspended in a solution of 15mL of hexane. Fluorescent nanoparticles are obtained having an average diameter of approximately 2 nm and emitting around 520 nm.
• Example 2 100 ⁇ l of the solution of core / shell fluorescent nanoparticles obtained in Example 2 was mixed with 5 ⁇ l of TOP. This mixture is added to 1 mL of colorless nail hardener ("nail hardener" from C. Dior) or a pure varnish ("pure varnish long lasting formalin free, toluene free, rosin free "from PHAS hypoallergenic).
• nail hardener from C. Dior
• pure varnish pure varnish long lasting formalin free, toluene free, rosin free "from PHAS hypoallergenic
• varnishes were prepared comprising fluorescent nanoparticles of CdSe / ZnS whose size varies between 1, 5 and 6 nm in diameter to give fluorescent varnishes in blue (1, 5nm in diameter), green ( 3nm in diameter), orange (5nm in diameter) or red
• the drying, adhesion, gloss and resistance of the varnish are not affected by the presence of the fluorescent nanoparticles.
• Tolerian cream (La Roche-Posay) was mixed with 100 ⁇ l of solution of fluorescent nanoparticles prepared above encapsulated in phospholipid micelles obtained by following the protocol described in the article by Dubertret et al . (In vivo imaging of quantum dots encapsulated in phospholipid micelles Science 298, 1759-1762).

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• 2002
  • 2002-11-28 FR FR0214987A patent/FR2847812B1/fr not_active Expired - Fee Related
• 2003
  • 2003-11-28 US US10/536,736 patent/US20060165621A1/en not_active Abandoned
  • 2003-11-28 AU AU2003294105A patent/AU2003294105A1/en not_active Abandoned
  • 2003-11-28 JP JP2004556437A patent/JP2006514017A/ja active Pending
  • 2003-11-28 CN CNA2003801044793A patent/CN1717214A/zh active Pending
  • 2003-11-28 EP EP03789525A patent/EP1565147A1/fr not_active Withdrawn
  • 2003-11-28 WO PCT/FR2003/003525 patent/WO2004050046A1/fr active Application Filing
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