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WO2011089571A2 - Composition cosmétique comprenant au moins un composé fluorophore - Google Patents

Composition cosmétique comprenant au moins un composé fluorophore Download PDF

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Publication number
WO2011089571A2
WO2011089571A2 PCT/IB2011/050281 IB2011050281W WO2011089571A2 WO 2011089571 A2 WO2011089571 A2 WO 2011089571A2 IB 2011050281 W IB2011050281 W IB 2011050281W WO 2011089571 A2 WO2011089571 A2 WO 2011089571A2
Authority
WO
WIPO (PCT)
Prior art keywords
fluorophore
curve
compound
range
fluorophore compound
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.)
Ceased
Application number
PCT/IB2011/050281
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English (en)
Other versions
WO2011089571A3 (fr
Inventor
Laurent Vidal
Etienne Huguet
Philippe Barbarat
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
Application filed by LOreal SA filed Critical LOreal SA
Publication of WO2011089571A2 publication Critical patent/WO2011089571A2/fr
Publication of WO2011089571A3 publication Critical patent/WO2011089571A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • 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
    • 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
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • 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
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/621—Coated by inorganic compounds
    • 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
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/65—Characterized by the composition of the particulate/core
    • A61K2800/652—The particulate/core comprising organic material

Definitions

  • the present invention relates to cosmetic
  • compositions for application to the skin, the lips, hair, or nails and more particularly but not exclusively to cosmetic compositions for lightening the skin or for modifying its tone.
  • compositions containing bleaching agents such as hydroquinone and its
  • dyschromia of the skin occurring either with age or following exposure to UV radiation, during pregnancy, or as a result of skin disease.
  • Such bleaching agents act by modifying the
  • melanin biological activity of melanocytes and by limiting pigmentation due to the formation of melanin.
  • hydroquinone or its derivatives have proved to have a certain degree of cytotoxicity. Broadly, such bleaching agents induce phenomena of allergies or skin irritation that can be severe.
  • compositions that make the complexion uniform, giving it an immediate white appearance.
  • Such compositions contain diffusing white pigments that provide them with opacity and the coverage necessary to obtain the desired effect.
  • emissive compounds such as fluorescent organic, semi-organic, or inorganic molecules or materials in cosmetic compositions are limited by various effects rendering the lightening of the skin color barely perceptible.
  • Effects that may be mentioned are those due to intensities of emission under natural light excitation that are too weak because of their intrinsic molecular structures; effects due to photo-degradation of the fluorophores and to their chemical reactivity with the environment of the formulation, reducing the quantity of fluorescent substances in the compositions containing them; effects due to the phenomenon of absorption of wavelengths in the visible region dominating the
  • emissive materials that emit light in the visible region after excitation by natural light, in which the intensity of emission is sufficiently high to render the lightening of the skin color by the cosmetic compositions containing them perceptible, and that have sufficient stability under natural illumination and in conjunction with the ingredients of the cosmetic compositions in which they are contained.
  • Publication FR 2 778 561 proposes the use of optical brighteners, possibly in association with skin bleaching agents, UV screens, anti-wrinkle agents, and moisturizing agents.
  • optical brighteners possibly in association with skin bleaching agents, UV screens, anti-wrinkle agents, and moisturizing agents.
  • the chemical families of those optical brighteners possibly in association with skin bleaching agents, UV screens, anti-wrinkle agents, and moisturizing agents.
  • brighteners are more particularly those of stilbene, coumarin, oxazole, benzoxazole, and imidazole. More precisely, Tinopal SOP and Uvitex OB are proposed.
  • the skin lightening effect is not entirely satisfactory, and cannot be used to modulate the tone as much as would be liked as a function of various skin tones .
  • organic optical brighteners are unstable in light, which results in a reduction in the lightening efficiency of cosmetic compositions containing them. They also have a certain reactivity with the components of the cosmetic compositions, which denatures their molecular structure, thereby inducing a reduction in the fluorescence of the brightener and thus in the lightening effect.
  • the publication WO 01/43714 discloses polymeric particles, in particular based on starch or cellulose, doped with optical brighteners.
  • the quantity by weight of fluorescent agent in the matrix is limited by the solubility and matrix diffusion properties, and is around a value of 1.5%.
  • the intensity of the fluorescence is limited thereby, along with the consequent lightening effect.
  • the publication FR 2 810 881 proposes lightening the skin color by applying a composition containing optical brighteners included in inorganic particles such as titanium oxide aluminas.
  • a composition containing optical brighteners included in inorganic particles such as titanium oxide aluminas.
  • the publication FR 2 857 254 proposes cosmetic compositions containing mineral microparticles having a high degree of porosity where the organic optical brightener is immobilized and thus protected from
  • publication FR 2 885 520 proposes cosmetic compositions containing a mixture of at least two photoluminescent agents that may be coated with a transparent matrix with a mean dimension of less than 100 nm [nanometer] , such as the compounds Luminux Effect Blue A, Luminux Effect Red A, Luminux Effect Green A, sold by the supplier Honeywell.
  • those photoluminescent agents that may be coated with a transparent matrix with a mean dimension of less than 100 nm [nanometer] , such as the compounds Luminux Effect Blue A, Luminux Effect Red A, Luminux Effect Green A, sold by the supplier Honeywell.
  • photoluminescent agents have phosphorescence and weak fluorescence, which makes them luminescent in the dark and weakly so in daylight. The visibility of the skin color lightening effect is thus relatively small in daylight.
  • inorganic fluorophores with the exception of II/VI quantum dots (QD II/VI) such as those based on cadmium or tellurium, are known to be less fluorescent than organic fluorophores.
  • QD II/VI II/VI quantum dots
  • 2 873 021 employs cosmetic compositions containing fluorescent silicon nanoparticles, such as those sold by the supplier NanoSi Inc.
  • the photostability of those fluorescent agents is improved along with their chemical stability, but the quantum yields for fluorescence are relatively low, causing the intensity of the desired effect to be barely perceptible.
  • optical brighteners proposed cannot of themselves produce a skin lightening effect and they are used in this context to supply radiative energy to the associated fluorescent compound. They fluoresce in the wavelength range 550 nm to 700 nm, i.e. in the orange and red range. This results in a lightening effect that is clearly insufficient to which an
  • the publications FR 2 848 821 and PR 2 848 822 propose cosmetic compositions containing colorizing agents and reflective particles with a color from pinky beige to orangey beige, characterized by a hue h between 50° and 70° and a saturation C in the range 20 to 50. That solution is limited because of the use of colorizing agents that absorb light to provide the desired hue.
  • colorizing agents such as white opacifying mineral or organic fillers in order to attempt to lighten the skin color.
  • they also create a grayish color effect that is
  • the publication FR 2 872 032 proposes cosmetic compositions containing solid particles with a refractive index in the range 1.2 to 1.5 derived from cured
  • the colorizing agent that can provide the composition with a color such that the hue h is in the range 40° to 70° and the saturation C is in the range 20 to 50.
  • the skin color obtained after application of the compositions containing such ingredients is less dull than with those described in the publications FR 2 848 821 and FR 2 848 822, the lightening effect is still relatively- difficult to notice and is hard, to modulate.
  • the publication WO2009/003996 discloses the use of cosmetic compositions containing both particles of titanium oxide with a dimension in the range 300 nm to 1000 nm and also biological bleaching agents such as vitamin B3 or its niacinamide and nicotine derivatives. That association produces an immediate bleaching effect provided by the titanium oxide particles, as well as a long term effect due to the biological bleaching agents.
  • the skin color obtained owes more to an opacifying bleaching effect than to a luminous
  • novel cosmetic compositions that, depending on the desired result, may be used for making up human keratinous substrates, such as the skin, in particular of the body, hands, neck, face, and lips, and/or such as keratinous fibers, especially the eyelashes, eyebrows or hair of the head, for example, to provide immediate, long-lasting and modulatable lightening of the tone of those keratinous substrates while retaining a natural appearance and/or to camouflage skin dyschromias.
  • human keratinous substrates such as the skin, in particular of the body, hands, neck, face, and lips
  • keratinous fibers especially the eyelashes, eyebrows or hair of the head
  • a first fluorophore compound in particular having an absorption spectrum in the ultraviolet or visible region; and • a second fluorophore compound having an emission spectrum in the visible region overlapping the absorption spectrum of the first fluorophore compound, at least one of the two fluorophore compounds having luminescence enhanced by a proximity interaction effect with at least one metal, the metal and the fluorophore compound for which the fluorescence is enhanced being present in the same particle, i.e. one and the same particulate
  • the invention allows the composition to absorb in a first wavelength range, especially in the blue and/or UV, and to re-emit by luminescence in a second wavelength range relatively far away from the first, especially in the red, which is not possible with a single fluorophore compound selected from the compounds in conventional use.
  • the invention also means that the intensity of the luminescence in the red may be enhanced by exploiting the excitation energy of the incident light in the blue.
  • composition may comprise at least three
  • fluorophore compounds as detailed below, at least two of said compounds possibly having fluorescence absorption and excitation spectra located in the visible and also re-emitting in the visible.
  • the first fluorophore compound may have increased luminescence within a first particulate material, namely that one and the same particle comprises the metal and the fluorophore.
  • the second fluorophore compound may have an
  • the composition may comprise a third fluorophore compound.
  • the third fluorophore compound may have enhanced luminescence within a third particulate
  • material namely one and the same particle comprises the metal and the fluorophore.
  • fluorophore compounds In the presence of three fluorophore compounds, they may be selected so that they have respective emission spectra in the red, in the green, and in the blue, in order to generate by addition white light or
  • Fluorophore compounds that emit in the red may also emit in the green, if appropriate. Those emitting in the green may also absorb in the blue if appropriate.
  • the emission spectrum for the first fluorophore compound may cover the range from 580 nm to 700 nm, preferably with a mid-height width for the emission curve of the first fluorophore compound in the range 580 nm to 700 nm.
  • the emission spectrum for the second fluorophore compound may be in the range 480 nm to 620 nm, preferably with a mid-height width for the emission curve of the second fluorophore compound in the range 480 nm to
  • the first fluorophore compound may have a mid-height emission curve width in the range 580 nm to 700 nm and an absorption curve in the visible taken at mid-height in the range 480 nm to 620 nm, the second fluorophore compound having an emission curve taken at mid-height in the range 480 nm to 620 nm.
  • the coverage of the composition is preferably 70% or less, more preferably 65% or less, or 60%.
  • the composition has little or no opacifying power and the natural appearance of the skin is preserved.
  • the emission spectrum for the composition in the red may have an emission peak that substantially coincides with the maximum peak of sensitivity in the red for the human eye according to the CIE.
  • All of the fluorophore compounds of the composition may be free of rare earths.
  • composition as defined above is applied to the skin.
  • the invention also provides a method of modifying the tone of the skin and/or for lightening the skin, in which a composition as defined above is applied to the skin, the covering power of the composition being 70% or less, more preferably 65%, still more preferably 60%.
  • the invention provides a method of lightening the complexion or of modulating the tone of the skin, in which a cosmetic composition comprising at least one particulate material within which a fluorophore has enhanced fluorescence, in particular particles with a nanometric metallic core and a coating covering the core, said coating comprising at least one fluorescent molecule disposed at the surface of the coating or impregnating it and located at a distance from the metallic core that is sufficiently small to increase its fluorescence, is applied to the skin.
  • modulating the tone denotes a change in the color of the skin by means of a non opacifying composition or a composition that barely opacifies, in particular with a covering power of 70% or less,
  • the invention provides a method of enhancing the reflectance of skin in the wavelength region in the range 600 nm to 700 nm,
  • a cosmetic composition comprising at least two fluorophore compounds Fl and F2, characterized in that the
  • fluorophore compound Fl emits fluorescent light in the visible region such that the normalized emission curve for said fluorophore compound Fl and the relative
  • fluorophore Fl and the emission curve for the fluorophore F2 overlap each other when irradiated with natural light.
  • normalized curve means a curve reduced to a scale of 0 to 100%.
  • the invention provides a method of enhancing the reflectance of skin in the wavelength region in the range 500 nm to 600 nm, the method comprising the step consisting in applying to the skin a cosmetic composition comprising at least two fluorophore compounds F3 and F , and being characterized in that the fluorophore compound F4 emits fluorescent light in the visible region such that the normalized emission curve for the fluorophore compound F and the relative luminous efficiency curve defined by the CIE overlap each other in the wavelength region in the range 500 nm to 600 nm and in that the absorption curve for the fluorophore F4 and the emission curve for the fluorophore F3 overlap each other when irradiated with natural light.
  • the invention provides a method of enhancing the reflectance of skin in the wavelength region in the range 500 nm to 700 nm,
  • fluorophore compounds F5, F6, and F7 the method being characterized in that the fluorophore compound F5 emits fluorescent light in the visible region such that the normalized emission curve for the fluorophore compound F5 and the relative luminous efficiency curve defined by the CIE overlap each other in the wavelength region in the range 400 nm to 500 nm; in that the fluorophore compound F6 emits fluorescent light in the visible region such that the normalized emission curve for said fluorophore compound F6 and the relative luminous efficiency curve defined by the CIE overlap each, other in the wavelength region in the range 500 nm to 600 nm; in that the fluorophore compound F5 emits fluorescent light in the visible region such that the normalized emission curve for the fluorophore compound F5 and the relative luminous efficiency curve defined by the CIE overlap each, other in the wavelength region in the range 500 nm to 600 nm; in that the fluorophore compound F5 emits fluorescent light in the visible region such that the normalized emission curve for the fluor
  • fluorophore compound F7 emits fluorescent light in the visible region such that the normalized emission curve for said fluorophore compound P7 and the relative
  • the overlap between the curves is such that twice the common area of the two overlapping curves represents at least 20%, 30%, 40%, 50%, 60%, 70% or preferably 80% of the sum of the areas of each of said curves. This value is termed the degree of overlap.
  • the mid-height width of the common area is, for example, more than 5 nm wide, or even more than 10, 20 or 30 nm wide.
  • the invention also pertains to a cosmetic
  • composition per se to implement one of the methods defined above.
  • visible region is assumed to be the range from 400 nm to 700 nm.
  • the relative luminous efficiency curve corresponds to the photopic vision curve for day vision as defined by the CIE on the site, http: //www. led-fr.net/efficacite- lumineuse-relative.htm, given in Figure 6. However, that curve could more preferably be
  • a particulate material namely one and the same particle comprising the metal and the fluorophore.
  • a composition of the invention may act to lighten the skin, as shown in the implementational examples.
  • skin lightening means a modification of the reflectance of the made-up skin compared with bare skin, such that an observer would see it as being lighter without it in any way losing its natural appearance.
  • the lightening may be observed if the overall reflectance of the made-up skin is greater than the reflectance of the skin that has not been made up.
  • the reflectance of a material denotes the percentage of light reflected by that material compared with that observed with a perfectly white reference material at each
  • composition implies that the reflectance spectrum of the made-up skin has, at least over one spectral window, reflectance values that are higher than the values observed in the same spectral window for skin that has not been made up. That relative enhancement of the reflectance is at least 5%, preferably more than 10%.
  • composition of the invention is preferably, the composition of the invention
  • 600 nm-700 nm preferably by at least 0.05, preferably 0.1, on a scale from 0 to 1, for at least one wavelength, and preferably for at least a 20 nm wide interval, or even 50 nm wide, in this 600 nm-700 nm range.
  • Skin lightening protocol preferably by at least 0.05, preferably 0.1, on a scale from 0 to 1, for at least one wavelength, and preferably for at least a 20 nm wide interval, or even 50 nm wide, in this 600 nm-700 nm range.
  • the reflectances may be measured before and after making up using an acquisition device such as that described in Figure 1 of application US 2003/0067545, comprising a sphere inside which several independent and non-apparent sources of white light are disposed so that the light reaching its aperture is as uniform as
  • the face of the individual whose color is to be measured is placed in that aperture and images are acquired using color cameras or digital photographic apparatus, the reflectance spectra being acquired using a spectroradiometer .
  • the acquisition system is calibrated by placing colorimetric standard references in the field of the cameras, for example using the method described in US 6 362 849, the contents of which are herewith incorporated by reference.
  • the color measurements may, for example, be carried out in three regions of the face, for example a first region located on the forehead, a second region
  • the color is measured before making up the skin that has been cleansed and after making up, for example 15 minutes after finishing it.
  • compositions are applied directly onto the skin in the usual manner without previously depositing a base, in an amount of approximately 0.5 mg [milligram] to 1 mg per cm 2 [square centimeter], preferably in the range 0.7 mg/cm 2 to 0.8 mg/cm 2 .
  • the coverage of the composition is not too high, in order to retain a natural appearance for the makeup .
  • compositions that are liquid (at 25°C)
  • liquid composition means a composition of viscosity that can be measured.
  • a liquid composition is capable of flowing under the effect of its own weight.
  • the coverage of the liquid compositions is measured at a finished thickness of 50 ⁇ [micrometer] for liquid compositions for application to the lips, especially liquid lipsticks, liquid lip glosses, and liquid lip balms, for nail polishes, eye shadows, liquid
  • composition is smoothed onto matt black and matt white contrast cards, for example with trade mark LENETA Form WP1 for the matt black card and LENETA 1A for the matt white card.
  • Application may be carried out with an automatic smoother .
  • compositions that have been smoothed on Compositions that are solid (at 25°C)
  • Solid compositions are those of viscosity that cannot be measured.
  • compositions cast into sticks or powders in the form of loose or pressed powders.
  • compositions loose or pressed, the composition is applied using the same contrast cards as above, coated with a transparent, slightly rough adhesive strip, for example of trade mark BLENDERM ® from the supplier 3M with reference 15025, bonded to the contrast cards via the adhesive face.
  • a transparent, slightly rough adhesive strip for example of trade mark BLENDERM ® from the supplier 3M with reference 15025
  • composition is deposited onto the adhesive strip so as to obtain a uniform deposit of
  • a sponge loaded with the composition for deposition and mounted on a dispersing apparatus that makes pre-defined movements with the sponge.
  • the sponge is, for example, a single-use sponge of the "LANCOME - Photogenic" type used on the pink side.
  • Stick compositions are melted, for example at 90°C, then smoothed in the liquid state onto matt black and matt white contrast cards, for example with the same references as above, but not covered with BLENDERM ® .
  • the smoothing bar is kept at the same temperature as the composition in order to avoid thermal shock.
  • the reflectance spectra are acquired using a MINOLTA 3700-d spectrocolorimeter (diffuse measurement
  • the contrast ratio, or coverage is calculated by taking the arithmetic mean of Y on the black background divided by the mean value of Y on the white background multiplied by 100.
  • the coverage values are preferably less than 70%, more preferably less than 65%, ideally less than 60%.
  • Figure 1 illustrates the overlap between the absorption spectrum A 1 of a first fluorophore compound of an example of a composition of the invention and the emission spectrum E 2 of another fluorophore compound of the composition, these fluorophore compounds both belonging, for example, to respective particulate materials comprising a metal interacting with the
  • the overlap of spectra A 1 and E 2 may be such that twice the common area as represented by the gray common portion is at least 20% of the sum of the areas of spectra A 1 and E 2 , i.e. the degree of overlap is at least 20%, or more, e.g. at least 50%.
  • the mid-height of the emission spectrum E 1 of the first fluorophore compound is in the range 580 nm to 700 nm.
  • the absorption spectrum A 1 is, for example, in the range 480 nm to 600 nm and the emission spectrum for the second fluorophore compound E 2 is in the range 480 nm to 600 nm.
  • the emission spectrum E 3 thereof may overlap, for example with a degree of overlap of more than 0.2, 0.5 or more, with the absorption spectrum A x and the absorption spectrum A 3 of the third fluorophore compound may be offset from the spectrum A 2 , for example offset further towards shorter wavelengths, as
  • the emission spectrum E 3 may also overlap the absorption spectrum A 2 , for example with a degree of overlap of more than 0.2, 0.5 or more , as illustrated in Figure 3.
  • the cosmetic composition may comprise at least two fluorophore compounds Fl and F2 characterized in that the fluorophore compound Fl emits fluorescent light in the visible region such that the normalized emission curve for said fluorophore compound Fl and the relative luminous efficiency curve defined by the CIE overlap each other in the wavelength region in the range 600 nm to 700 nm, for example with a degree of overlap of more than 0.2, 0.5 or more; and in that the absorption curve for the fluorophore Fl and the emission curve for the fluorophore F2 overlap each other under natural light, for example with a degree of overlap of more than 0.2, or even 0.5 or more.
  • the term "natural light” means light with the characteristics of the D 65 illuminant .
  • the cosmetic composition may comprise at least two fluorophore compounds F3 and F4 characterized in that the fluorophore compound F4 emits fluorescent light in the visible region such that the normalized emission curve for the fluorophore compound F4 and the relative luminous efficiency curve defined by the CIE overlap each other in the wavelength region in the range 500 nm to 600 nm, for example with a degree of overlap of more than 0.2, 0.5 or more; and in that the absorption curve for the fluorophore F4 and the emission curve for the fluorophore F3 overlap each other under natural light, for example with a degree of overlap of more than 0.2, or even 0.5 or more .
  • the cosmetic composition may comprise at least three fluorophore compounds F5, F6, and F7 characterized in that the fluorophore compound F5 emits fluorescent light in the visible region such that the normalized emission curve for the fluorophore compound F5 and the relative luminous efficiency curve defined by the CIE overlap each other in the wavelength region in the range 400 nm to 500 nm, for example with a degree of overlap of more than 0.2, 0.5 or more; in that the fluorophore compound F6 emits fluorescent light in the visible region such that the normalized emission curve for said fluorophore compound F6 and the relative luminous efficiency curve defined by the CIE overlap each other in the wavelength region in the range 500 nm to 600 nm; and in that the fluorophore compound F7 emits fluorescent light in the visible region such that the normalized emission curve for the fluorophore compound F7 and the relative luminous efficiency curve defined by the CIE overlap each other in the wavelength region in the range 600 nm to 700 nm, for example with
  • fluorophore compound should be understood to mean a fluorescent compound.
  • the total weight content of fluorophore compounds in the composition of the invention may lie in the range 0.0001% to 90% by weight.
  • the particulate material may be in the form of particles that may have a spherical or flake shape.
  • the particulate material comprises at least one fluorophore and at least one metal, preferably a noble metal, and has a structure preferably corresponding to structures (I) and ⁇ II) described below.
  • the enhanced fluorescence refers to the work by R.R. Chance, J. Chem. Phys. 1974, 60, 2744 and K.H. Drexhage, J. Lumin 1970, 1, 693 and in accordance with the invention encompasses MEF ⁇ metal -enhanced fluorescence) fluorescence as described in the publication "Metal-Enhanced Fluorescence", Chris D. Geddes and Joseph R. Lakowicz, Journal of
  • MEF fluorescence is also occasionally termed SPCF ⁇ Surface plasmon coupled fluorescence) or RDE (Radiative decay engineering) .
  • the distance between the two is sufficiently small, for example less than 300 nm, preferably less than 200 nm, more preferably less than 100 nm, or even 50 nm to 40 nm, or more preferably in the range 2 nm to 30 nm.
  • the invention is not limited to the particulate material structures (I) and (II) illustrated below and encompasses variations of these structures as well as other structures capable of producing amplification linked, for example, to a plasmonic resonance effect.
  • the metal may be directly coated with a layer of a fluorophore compound.
  • the metal and the fluorophore may also both be contained in a matrix.
  • a particulate material of the present invention may also be constituted by an aggregate of at least two different materials, each possibly comprising a metal and a fluorophore interacting with the metal, for example.
  • luminescence of the fluorophore comprise, for example, one or more metals selected from the group constituted by the following metals: aluminum (Al) , palladium (Pd) , platinum (Pt) , silver (Ag) , copper (Cu) , gold (Au) , zinc (Zn) and alloys thereof.
  • the metal of the plasmonic particles is selected from the following metals: silver, aluminum, zinc, and gold and alloys thereof. Alloys of a plurality of metals may be
  • a plurality of metals may constitute a continuous metal phase such as an alloy, i.e. a continuous phase in which the metals are no longer dissociable, or a discontinuous phase of metals.
  • the metallic surface may have a variety of shapes such as spherical, cylindrical, cubic, conical, ovoid, polyhedral, with four to six faces, such as a perfect or truncated tetrahedron, a perfect or truncated cube, or a flake, especially an elliptical, triangular, pyramidal, or polyhedral flake. They may be smooth or rough.
  • composition of the invention is preferably, the composition of the invention
  • the composition of the invention may thus comprise particulate materials with structure (I) or (II) , in which the porosity of the outer shell is such that the pore size is in the range 1 nm to 50 nm, and the specific surface area is more than 500 m 2 /g [square meter/gram] .
  • the cosmetic composition may comprise at least three fluorophore and metal materials, preferably each with structure (I) or (II) , such that at least three
  • fluorescence emissions are produced in the blue, green, and red in order to obtain a white or near white color.
  • Fl, F2, F3, F4, F5, F6, and F7 described above may each be present in a structure of particulate materials (I) or (II) as defined below.
  • the particulate fluorophore In general, irrespective of the structure of the particulate material, the particulate fluorophore
  • compound or compounds may be selected from any one of the fluorescent compounds described below, and more
  • the fluorophore may be any fluorophore, for example selected from those listed for portion B and in Examples 1 to 14.
  • Structure (I), as illustrated in Figure 4, comprises or is constituted by three portions A, B and C, in a specific organization such that portion A is enveloped by portion C with a thickness of 1 nm to 100 nm and such that portion B is outside portion A and inside portion C, optionally being bonded by cov lent bonding to the chemical functions of portion C.
  • portion D comprises or is constituted by four portions D, E, C, and B having a specific organization such that portion D is enveloped by portion E with a thickness of 1 nm to
  • the ensemble obtained D+E itself being enveloped by portion C with a thickness of 1 nm to 100 nm and portion B being outside the ensemble D+E and inside portion C, possibly being bonded thereto by covalent bonding .
  • Portion A comprises or is even constituted by a metal particle, the metal being selected from group Gi below, with a dimension in the range 3 nm to 500 nm in any one of the three axes in space, of shape that may be spherical, cylindrical, ovoid, conical, polyhedral, with four to ten faces, such as a perfect or truncated tetrahedron, a perfect or truncated cube (as described by Y. Xia, Science, 2002, 298, 5601, 2176 - 2179), a rectangular parallelepiped, an octagonal cylinder (as described by Y. Xia, Angew. Chem. Int.
  • the group G x is, for example, constituted by silver, gold, platinum, copper, aluminum, palladium, zinc, nickel, or one of their alloys.
  • the constitutive particles of portion A are of portion A.
  • They are preferably spherical, cylindrical,
  • pyramidal, or ovoid in shape preferably spherical or ovoid; and more preferably spherical.
  • They are preferably in the range 3 nm to 300 nm in dimension; preferably in the range 3 nm to 160 nm; more preferably in the range 30 nm to 80 nm for gold, or in the range 30 nm to 200 nm for silver. More preferably in the range 30 nm to 120 nm for silver.
  • Portion B comprises or is even constituted by at least one fluorophore independently selected from the list in the European Cosmetic Directive's FDA list:
  • group G 4 is constituted by compounds belonging to the following chemical families: xanthenes, benzo [a] xanthenes ,
  • phenothiazines benzo [b] thiazines , benzo [c] thiazines , naphthalimides , naphtholactams, lactamimides ,
  • quinacridones quinacridones , epindolines, thio-epindolines,
  • triazines 1, 3 , 5-triazin-2-yl derivatives, pyrazines, triazoles, methines, distyrylbenzenes, distyrylbiphenyls, divinylstilbenes, triazinylaminostilbenes, stilbenyl-2H- triazoles, benzoxazoles, benzofurans, benzimidazoles, 1, 3-diphenyl-2-pyrazolines, diketopyrrolopyrroles
  • Xi represents an oxygen atom
  • N-Z 1 ⁇ + ⁇ ⁇ ⁇ 2 radical
  • X 2 represents a hydroxy radical
  • Z 1 , Z 2 independently of each other, represent a radical selected from the group G 1 constituted by a hydrogen atom; a linear or branched C 1 -C 8 alkyl,
  • a 0R 8 radical optionally interrupted by one or more oxygen atoms, and optionally substituted with one or more radicals selected from the group constituted by a 0R 8 radical, a NR 9 R 10 radical, a carboxy radical, a COOM radical, a thiol radical, a cyano radical, a halogen, a sulfonic radical, a CONR 9 R 10 carboxamido radical, a SO 2 R 9 R 10 sulfonamido radical; an aryl radical optionally substituted with one or more radicals selected from the group Gp 4 ; a heteroaryl radical optionally substituted with one or more radicals selected from the group Gp 4 ;
  • the C 1 -C 8 alkyl chain as defined above may be interrupted by one or more oxygen atoms;
  • (C 1 -C 2 ) alkoxy radicals (C 1 -C 2 ) alkoxy radicals; C 1 -C 4 alkyl radicals optionally substituted with one or more hydroxy, amino, (di) - alkylamino, alkoxy, carboxy, or sulfonyl radicals; the cycle containing neither a peroxide bond nor diazo or nitroso radicals;
  • X 1 may optionally be connected to R 6 and/or to R 7 (respectively to R 1 or R 2 ) , to together form a saturated or unsaturated, possibly cationic carbocycle or a heterocyle containing 5 to 6 members such as, for example, a cyclohexyl, cyclohexenyl ,
  • dehydropiperidinyl or pyrrolidinyl cycle
  • the associated anion or mixture of anions is selected from the group constituted by a halide such as chloride, bromide, fluoride, or iodide, a hydroxide, a sulfate, a hydrogenosulfate, an alkylsulfate wherein the alkyl portion, linear or branched, is C 1 -C 6 , such as the
  • hydrogenocarbonates ; carboxylic acid salts such as the formate, acetate, citrate, tartrate or oxalate;
  • alkylsulfonates wherein the alkyl portion, linear or branched, is C 1 -C 6 , such as the methylsulfonate ion;
  • arylsulfonates wherein the aryl portion, preferably phenyl, is optionally substituted with one or more C 1 -C 4 alkyl radicals such as 4-toluylsulfonate, for example;
  • R 1 , R 2 , R 3 , R 5 , R 6 , R 7 which may be identical or different, represent a radical selected from the group Gp 3 constituted by a hydrogen atom; a halogen, a C 1 -C 4 alkyl optionally substituted with one or more radicals selected from the group constituted by a OR 8 radical, a SR 8
  • sulfonatnido radical a carboxy radical; a cyano radical, a carboxamido radical (RCONH-) ; a (C 1 -C 4 ) alkylsulfonyl (SO 2 R) radical; an alkylsulfonatnido ( (C 1 -C 4 ) alkyl SO 2 NH-) radical; a ⁇ -S0 3 H) sulfonic radical; a C 1 -C 4 thioether radical; a (C 1 -C 4 ) alkylsulfoxide (-SOR) radical; an aminosulfonyl (NH 2 -SO 2 -) radical; a hydroxy radical; a C 1 -C 4 alkoxy radical; a thioether radical; a C 2 -C 4
  • hydroxyalkoxy radical a NR 13 R 14 radical; an aryl radical optionally substituted with one or more radicals selected from the group Gp 4 ; a heteroaryl radical optionally substituted with one or more radicals selected from the group Gp 4 ,- or a cationic aza-heteroaryl radical optionally substituted with one or more radicals selected from the group Gp 4 ;
  • R 5 and R e may form a saturated or unsaturated carbocycle or a heterocycle containing 6 members
  • R 4 represents a hydrogen, halogen; cyano;
  • R 8 , R 9 and R 1 o which may be identical or different, represent a hydrogen atom; or a linear or branched C 1 -C 4 radical optionally substituted with one or more radicals selected from the group constituted by a hydroxy, a C 1 -C 2 alkoxy, a CONRnR 12 carboxamido, or a SO 2 R 11 sulfonyl radical;
  • R 11 and R 1 which may be identical or different, represent a hydrogen atom or a linear or branched C 1 -C 4 alkyl radical optionally substituted with one or more hydroxy, C 1 -C 2 alkoxy;
  • the group Gp 4 is constituted by a halogen; cyano; hydroxy; C 1 -C 4 alkoxy; carboxy; carboxamido;
  • R 13 and R 14 independently of each other represent a radical selected from the group Gpi. Together with the nitrogen atom carrying them, they may form a cycle containing 5 to 7 members;
  • R 1 s is defined by the same radicals as for R 1 ;
  • X' 2 represents a hydroxy radical; a C 1 -C 2 alkoxy radical; or a NZ 1 Z 2 radical provided that Z x and Z 2 do not together represent a hydrogen atom;
  • X' 2 and R 2 may together form a cycle containing 5 to 6 members, possibly unsaturated and optionally substituted with a radical from group Gp3.
  • phenothiazines, benzo [b] thiazines, benzo [c] thiazines family are respectively represented by the formulas (F-
  • R'7 represents a radical selected from the group
  • R' 3 and R' 5 represent radicals such as those defined for R 3 and R 5 , and may possibly form a lactam cycle wherein the nitrogen atom is optionally substituted with a Z 1 group? and
  • • r represents an integer in the range 0 to 5.
  • Preferred compounds with formula (F-X) are:
  • X 4 represents a radical such as that defined for X 1 ; a heterocyclic radical; a C 1 -C 4 alkyl radical optionally substituted with one or more radicals selected from hydroxy, C 1 -C 4 alkoxy, cyano; carboxy, carboxamido, (C 1 -C 4 ) alkylsulfonyl, sulfonic, alkylsulfoxide,
  • alkylsulfonamide aryl radicals optionally substituted with one or more radicals selected from group Gp 4 ; a heteroaryl radical optionally substituted with one or more radicals selected from group Gp 4 .
  • Preferred compounds with formula (F-XI) are:
  • R 9 and R 1 o independently of each other designate a hydrogen atom, a C 1 -C 8 alkyl radical or a C 1 -C 6 alkoxy radical .
  • R 16 and R 17 represent radicals such as those defined for radical R x ;
  • X 5 represents an oxygen atom, sulfur atom or a N-Z 1 group
  • R 18 , R 19 , R 20 , and R 21 represent radicals such as those defined for radical R 1 .
  • (F-XV) i- Fluorophores from the oxazolones family are preferably represented by the formula (F-XVI) :
  • R 2 2 and R 2 3 independently of each other represent a radical selected from the group Gp 4 ;
  • EP-2004053111 k- Fluorophores from the pyrimidines, triazine,
  • Fluorophores from the stilbenes family are represented by the formula (F-XVII) :
  • R 34 and A 2 represent an aryl radical optionally substituted with one or more radicals selected from the group Gp 5 ; an aromatic heterocyclic radical optionally substituted with one or more radicals selected from the group Gp 5 ; or a cationic aromatic heterocyclic radical optionally substituted with one or more radicals selected from the group Gp s ;
  • the group Gp 5 is constituted by a hydrogen atom; a linear or branched C 1 -C 4 alkyl radical optionally
  • indazole imidazole, pyrrole, indole, pyrrolidine, indoline, oxadiazole, said radical possibly being substituted with one or more radicals selected from the group Gp 4 ;
  • R 39 and R 40 independently of each other represent a radical selected from the group G 1 and in particular a triazinyl group optionally substituted with a radical selected from the group Gp 6 constituted by a C 1 -C 4 alkoxy radical; NR 41 R 2 ; C 1 -C 4 alkyl optionally substituted with one or more radicals selected from hydroxy, C 1 -C 4 alkoxy, carboxy, carboxamido, (C 1 -C 4 ) alkyl sulfonyl, sulfonic, alkylsulfoxide, alkylsulfonamido or 43 R 44 radicals;
  • R 39 and R 40 may together form a carbocycle or heterocycle containing 5 to 7 members with the nitrogen atom carrying them;
  • R 41 , R 12 , R 43 and R 44 independently of each other represent a radical selected from the group Gp 1 ;
  • R 41 and R 42 on the one hand, R 43 and R 44 on the other hand may together form a carbocycle or heterocycle containing 5 to 7 members with the nitrogen atom that carries them such as a pyrrolidine, morpholine, or thiomorpholine cycle, as non-limiting examples;
  • R 35 , R 36 , R 37 and R 38 independently of each other represent a hydrogen radical; C 1 -C 8 alkyl optionally substituted with one or more radicals selected from the group constituted by a ORs radical, a carboxy radical, a sulfonic radical wherein the carbonaceous chain may possibly be interrupted by one or more oxygen atoms;
  • R 34 and R 37 may be connected together to form a heterocycle selected from benzofuran, benzothiophene , indole, azaindole;
  • L represents a linear or branched C 2 -C 10 alkyl radical, the carbon chain of which may possibly be interrupted by at least one oxygen atom, optionally- substituted with a C 2 -C 8 alkoxy radical; or a (di) (C 2 -C 8 ) alkylamino radical;
  • R 34 and A 2 independently of each other, preferably represent a phenyl, naphthyl, pyridine, pyrimidine, imidazole, pyrazole, pyrrole, triazole, benzoxazole, benzimidazole, indole, azaindole, oxazolium, thiazolium, pyridinium, pyrimidinium, imidazolium, benzimidazolium, pyrazolium, pyrrolium, triazolium, oxazolium or
  • Preferred derivatives that may be mentioned are those of styrylstilbene, triazinostilbene,
  • Preferred compounds for B are:
  • DC Red n° 6 and DC Red 7 (Ca salt of DC Red 6) : Disodium 3-hydroxy-4- [ (4-methyl-2-sulfonatophenyl) azo] -2- naphthoate;
  • UVINUL D-50 Benzophenone-3
  • UVINUL M-40 Benzophenone-3
  • Benzophenone-4 UVINUL MS-40
  • Benzophenone-8 SPECTRA SORB UV-24
  • Methoxycinnamate BERNEL HYDRO
  • Ethyl dihydroxypropyl-PABA AMERSCREEN P
  • Glyceryl PABA NIPA GMPA
  • Homosalate KEMESTER HMS
  • Methyl Anthranilate SUVINUL N-539)
  • PABA dimethyl PABA
  • Triethanolamine salicylate (SUNAROME W) ; 3-(4- methylbenzylidene) -camphor (UNSOLEX 6300) ; Benzophenone-6 (UVINUL D-49) ; Benzophenone-12 (UVINUL 408) ; 4- isopropyldibenzoylmethane (EUSOLEX 8020) ; Butyl
  • PARSOL1789 methoxydibenzoylmethane
  • Etocrylene UVINUL N-35
  • TINOPAL OB (CIBA, 2 , 5-thiophenediylbis (5-ter- butyl- 1 , 3 -benzoxazole) ; • TINOPAL ABP-Z (CIBA) ; TINOPAL NFW;
  • TINOPAL MSP hexasodium 2,2'- [vinylenebis [ (3-sulfonato-4 , 1-phenylene) imino (6- morpholino-1, 3 , 5-triazine-4 , 2- diyl) imino] ] bis (benzene-1, 4 -disulfonate) ;
  • TINOPAL SFP hexasodium 2,2'- [vinylenebis [ (3-sulfonato-4 , 1-phenylene) imino (6- diethylamino) -1,3, 5-triazine-4 , 2- diyl) imino] ] bis (benzene-1, 4 -disulfonate) ;
  • UVITEX NFW (CIBA, disodium 4 , 4 'bis (2-sulfostyryl) - biphenyl) ;
  • UVITEX OB ⁇ CIBA, 2 , 5-thiophenediylbis (5-ter- butyl-1, 3-benzoxazole) ;
  • UVITEX OB (CIBA, 2 , 5-thiophenediylbis (5-ter- butyl-1, 3-benzoxazole) ;
  • DC Red n° 33 Disodium 5-amino-4-hydroxy-3- (phenylazo) naphthalene-2 , 7-disulfonate; • FDC Green n° 3: Dihydrogen (ethyl) [4- [4- [ethyl (3- sulfonatobenzyl) amino] (4-hydroxy-2- sulfonatobenzhydrylidene] cyclohexa-2, 5-dien-1-ylidene] (3- sulfonatobenzyl) ammonium, disodium salt;
  • FDC Yellow n° 6 Disodium 6-hydroxy-5- [ (3- sulfonatophenyl) azo] naphthalene-2 -sulfonate
  • FDC Yellow n° 5 Trisodium 5-hydroxy- 1- (4- sulfophenyl) -4- (4 -sulfophenylazo) pyrazole-3 -carboxylate;
  • DC Red n°28 sodium 3 , 4 , 5 , 6-tetrachloro-2- (1, 4, 5, 8- tetrabromo-6 -hydroxy-3 -oxoxanthen-9-yl) benzoate
  • DC Red n°27 3 , 4 , 5, 6-tetrachloro-2- (1, 4 , 5, 8- tetrabromo-6-hydroxy-3-oxoxanthen- 9-yl) benzoic acid;
  • FDC Blue no 1 Dihydrogen (ethyl) [4- [4- [ethyl (3- sulfonatobenzyl) ] amino] -2 ' - sulfonatobenzhydrylidene] cyclohexa-2, 5-dien-1-ylidene] (3- sulfonatobenzyl) ammonium, disodium salt;
  • FDC Yellow n° 6 Disodium 6-hydroxy-5- [ (3- sulfonatophenyl) azo] naphthalene-2-sulfonate
  • FDC Yellow n° 5 Trisodium 5-hydroxy-1- (4- sulfophenyl) -4- (4-sulfophenylazo)pyrazole-3-carboxylate; ⁇ TINOPAL CBS-X (CIBA, sodium 2,2'- ([1,1 ⁇ - biphenyl] -4,4' -diyldivinylene) bis (benzenesulfonate) ) ;
  • Portion C comprises, or even is constituted by, at least one organic or semi-organic macromolecular compound independently selected from the group G 2 or the group G 3 and with a molar mass in the range 5 x 10 2 g/mol to
  • Group G 2 is constituted by biocompatible compounds; biodegradable compounds; lipids; polysaccharides;
  • glycoproteins proteins; glycoproteins; glycolipids; neutral or charged lipids selected from group H 1 constituted by fatty
  • alcohols containing at least 10 carbon atoms in a linear or branched chain such as polyethyleneglycol (PEG) , fatty acids containing at least 10 carbon atoms in a linear or branched chain; lecithin; sphingolipids; fatty amines containing at least 10 carbon atoms in a linear or branched chain; polyesters; polyamides; polyethers such as polyoxyethylene-9-lauryl-1-ether; polythioethers;
  • polyureas polycarbonates; polycarbamides; polyaryls;
  • polysilicones selected from the group constituted by polydimethylsiloxanes (PDMS) , phenylated
  • polyorganosiloxanes such as phenyltrimethicones
  • diphenylmethyldimethyltrisiloxanes diphenyldimethicones , phenyldimethicones or polymethylphenylsiloxanes, which may be fluorinated; polysiloxanes modified with fatty acids, with fatty alcohols or with polyoxyalkylenes , fluorosilicones and pe fluorinated silicone oils, and mixtures thereof; volatile silicone oils such as cyclic or linear silicones, preferably with a viscosity at ambient temperature and at an atmospheric pressure of less than 8 mm 2 /s (8 cSt) , and in particular containing 2 to 7 silicon atoms, (preferably octamethylcyclotetra- siloxane, decamethylcyclopentasiloxane, hexadecamethyl- eyelohexasiloxane, heptamethylhexyltrisiloxane or
  • Group G 3 is constituted by metallic oxides with a valency in the range 1 to 6, the metallic portion being constituted by metallic elements selected from the group H 2 constituted by the metals titanium, iron, copper, zinc, zirconium, strontium, indium, silicon, tin, tellurium, niobium, bismuth, cerium, yttrium, or their alloys, such as TiO 2 , Fe 2 0 3 , CuO, ZnO, Y 2 0 3 , ZrO 2 , ln 2 0 3 , SiO 2 , SnO 2 ,
  • Ta 2 0 5 , Bi 2 0 3 , CeO 2 , SrO 2 , Si x O y x and y independently being in the range 0.1 to 2.
  • Portion C is preferably constituted by metallic oxide, non- limiting examples being Si x O y , x and y
  • C is constituted by PMMA, PVP, PS, of metallic oxide selected from Si x O y x and y independently being in the range 0.1 to 2, titanium oxides TiO 2 , silicas
  • C is constituted by metallic oxide selected from silicon oxides Si x O y , silicas SiO 2 , and preferably silicas SiO 2 .
  • (II) is preferably in the range 2 nm to 80 nm, preferably in the range 10 nm to 50 nm, preferably in the range 20 nm to 30 nm.
  • Portion D comprises, or even is constituted by, at least one organic or semi-organic polymeric compound independently selected from groups G 2 and G 3 ; they may be spherical in shape with a diameter in the range 20 nm to 250 nm, or cylindrical with the minor axis from 5 nm to 50 nm and the major axis from 20 nm to 250 nm (cf .
  • Portion D is preferably constituted by metallic oxide, non- limiting examples being silicon oxides, Si x O y , x and y independently being in the range 0.1 to 2 , silicas SiO 2 , iron oxides Fe 2 0 3 ; polyacrylates such as PMMA, for example; polystyrenes PS, or polyureas.
  • portion D is constituted by PMMA, PS, metallic oxides selected from Si x O y x and y independently being in the range 0.1 to 2, silicas SiO 2 .
  • portion D is constituted by metallic oxides selected from silicon oxides Si x O y , silicas SiO 2 ; and more preferably silicas Si0 2 .
  • portion D has a core diameter ranging from 150 to 250 nm.
  • Portion E comprises, or even is constituted by a metal selected from group Gi.
  • Portion E is more preferably selected from the group constituted by the metals silver, or gold; more
  • portion E has a thickness ranging from 5 to 30 nm.
  • One example of a method of producing a particulate material with structure (I) above may comprise steps consisting of initially mixing a precursor for portion C with a dispersion of portion A to obtain hybrid A+C particles, and secondly in dispersing said A+C particles in a solution or suspension containing at least one fluorophore compound for portion B, then in a third stage in possibly isolating the final material.
  • One example of a method of producing a particulate material with structure (II) above may comprise steps consisting of initially mixing a precursor for portion E with a dispersion of portion D to obtain hybrid D+E particles after isolation, and secondly in dispersing said D+E particles in a solution or suspension containing at least one precursor for portion C to obtain D+E+C particles after isolation, then in a third stage of dispersing said D+E+C particles in a solution or
  • the fluorophore compound or compounds of the invention may be selected from the above list a) to 1) , independently of whether structures (I) or ⁇ II) above are concerned.
  • a composition of the invention may be solid or fluid.
  • solid is used to mean a composition of high consistency, which retains its shape during storage.
  • compositions termed "fluid" it does not flow under its own weight.
  • a composition of the invention is in the solid form, and more particularly in the form of a pressed powder or a cast composition.
  • pressed powder means a mass of
  • composition of cohesion that is at least partially due to compacting during manufacture.
  • the term "cast composition" means a mass of
  • composition of cohesion that is due to solidification of at least one of its constituents during production.
  • the composition may be hot cast into a mold, and
  • a cast composition of the invention may be in the anhydrous form or in the form of a solid emulsion.
  • a solid emulsion does not flow under its own weight at ambient temperature, in contrast to a conventional emulsion, and is in particular characterized by the presence of wax(es) in the liquid fatty phase.
  • a composition of the invention may be in the fluid (liquid) form, with greater or lesser viscosity, with a creamy or pasty appearance, such as in the form of an oily or aqueous solution, containing an oily gel, or an oil-in-water , water- in-oil or multiple emulsion.
  • a composition of the invention must be cosmetically or dermatologically acceptable, namely contain a non- toxic medium that is capable of being applied to the keratinous materials of human beings, in particular to the skin.
  • cosmetically acceptable means a composition with an agreeable appearance, odor and feel.
  • the medium is generally adapted to how the
  • composition is to be packaged.
  • nature and the quantity of the various compounds are adapted, for example depending on whether the composition is formulated into the solid or fluid form.
  • composition of the invention may be in the form of a composition for makeup and/or care of keratinous materials, for example a blusher, an eye shadow, a face powder, a foundation, especially for application to the face or neck, a concealer, a complexion corrector, a tinted cream, a lipstick, a lip balm, or a colored skin care or makeup composition, in particular for the face or body.
  • keratinous materials for example a blusher, an eye shadow, a face powder, a foundation, especially for application to the face or neck, a concealer, a complexion corrector, a tinted cream, a lipstick, a lip balm, or a colored skin care or makeup composition, in particular for the face or body.
  • galenical dosage form that is suitable, in particular from fluid or solid forms that are suitable for topical application to keratinous materials, in particular the skin.
  • a composition of the invention may be in the form of a fluid, for example pasty or liquid, a gel, a cream, or in the form of a free or pressed powder, or a cast composition.
  • a fluid for example pasty or liquid, a gel, a cream, or in the form of a free or pressed powder, or a cast composition.
  • it may be an oil- in-water, water-in-oil or multiple emission, a solid emulsion in particular of the water-in-oil type, an aqueous or oily gel, a pressed or loose powder or a cast composition, especially in the anhydrous form or in the form of a solid emulsion.
  • the composition may be packaged into a packaging and application device comprising an applicator, the
  • application surface being defined, for example, by a brush, a sponge, a foam, a flocked membrane, a cloth or a nonwoven.
  • composition may be applied by spraying or transfer, if appropriate.
  • a composition of the invention may comprise an aqueous phase.
  • An aqueous phase comprises water.
  • Water suitable for use in the invention may be a floral water such as cornflower water and/or mineral water such as VITTEL water, LUCAS water or ROCHE POSAY water and/or a thermal water .
  • the aqueous phase may also comprise organic solvents that are miscible with water (at ambient temperature, 25°C) such as, for example, mono-alcohols containing 2 to 6 carbon atoms such as ethanol, isopropanol ; polyols in particular containing 2 to 20 carbon atoms, preferably containing 2 to 10 carbon atoms, and more preferably containing 2 to 6 carbon atoms, such as glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol; glycol ethers (in particular containing 3 to 16 carbon atoms) such as mono, di- or tripropylene
  • organic solvents that are miscible with water (at ambient temperature, 25°C) such as, for example, mono-alcohols containing 2 to 6 carbon atoms such as ethanol, isopropanol ; polyols in particular containing 2 to 20 carbon atoms, preferably
  • glycol (C 1 -C 4 ) alkylethers mono, di- or triethylene glycol (C 1 -C 4 ) alkyl ethers, and mixtures thereof.
  • the aqueous phase may further comprise stabilizing agents, for example sodium chloride, magnesium
  • the aqueous phase may also comprise any hydrosoluble or hydrodispersible compound that is compatible with an aqueous phase such as gelling agents, film-forming polymers, thickeners, surfactants, and mixtures thereof.
  • a composition of invention may comprise an aqueous phase in an amount in the range 1% to 80% by weight, in particular in the range 5% to 50%, and more particularly in the range 10% to 45% by weight relative to the total composition weight.
  • a composition of invention may be anhydrous.
  • An anhydrous composition may comprise less than 3% by weight of water, relative to the total composition weight, and in particular less than 2%, especially less than 1% by weight water relative to the total composition weight, water not being added during preparation of the composition but corresponding to the residual water supplied by the mixed ingredients.
  • an anhydrous composition may be completely free of water.
  • a cosmetic composition of the invention may comprise at least one liquid and/or solid fatty phase.
  • composition of the invention may comprise at least one liquid fatty phase, especially comprising at least one oil as mentioned below.
  • oil means any fat in the liquid form at ambient temperature (20°C to 25°C) and at atmospheric pressure .
  • a composition of the invention may comprise a liquid fatty phase in a quantity in the range 1% to 90% by weight, in particular in the range 5% to 80%, in
  • the oily phase suitable for the preparation of cosmetic compositions in accordance with the invention may comprise hydrocarbon oils, silicone oils fluorinated or otherwise, or mixtures thereof.
  • oils may be volatile or non-volatile. They may be of animal, vegetable, mineral or
  • volatile oil means an oil ⁇ or non-aqueous medium) susceptible of evaporating in contact with the skin in at least one hour, at ambient temperature and at atmospheric pressure.
  • the volatile oil is a cosmetic volatile oil that is liquid at ambient temperature, in particular having a non-zero vapor pressure at ambient temperature and at atmospheric pressure, in particular, having a vapor pressure in the range 0.13 Pa to 40000 Pa ⁇ 10 -3 mm to 300 mm Hg) , preferably in the range 1.3 Pa to 13000 Pa (0.01 mm to 100 mm Hg) , and more preferably in the range 1.3 Pa to 1300 Pa (0.01 mm to 10 mm Hg) .
  • non-volatile oil means an oil having a vapor pressure of less than 0.13 Pa.
  • silicon oil means an oil comprising at least one silicon atom, and in particular at least one Si-0 group.
  • fluorinated oil means an oil comprising at least one fluorine atom.
  • hydrocarbon oil means an oil principally containing hydrogen and carbon atoms.
  • the oils may optionally comprise atoms of oxygen, nitrogen, sulfur and/or phosphorus, for example in the form of hydroxyl or acid radicals.
  • the volatile oils may be selected from hydrocarbon oils containing 8 to 16 carbon atoms, and in particular C 8 -C 1 6 branched alkanes (also termed isoparaffins) , such as isododecane (also termed 2,2,4,4,6- pentamethylheptane) , isodecane, isohexadecane and, for example, oils sold under the commercial names ISOPARS ® or PERMETHYLS ® . It is also possible to use volatile silicones as the volatile oils such as, for example, linear or cyclic volatile silicone oils, in particular those with a viscosity ⁇ 8 centistokes (8 x 10 -6 m 2 /s) , and in
  • silicone oils that may be used in the invention that may be mentioned are dimethicones with a viscosity of 5 and 6 cSt, octamethyl
  • cyclotetrasiloxane decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl
  • fluorinated volatile solvents such as nonafluoromethoxybutane or
  • the composition of the invention may comprise 1% to 80% by weight, or even 5% to 70% by weight, or even 10% to 60% by weight and in particular 15% to 50% by weight of volatile oil relative to the total composition weight.
  • the non-volatile oils may, in particular, be
  • non-volatile hydrocarbon oils selected from non-volatile hydrocarbon oils, fluorinated oils and/or silicone oils.
  • Non-volatile hydrocarbon oils that may in particular be mentioned are:
  • hydrocarbon oils of animal origin such as
  • hydrocarbon oils of vegetable origin such as phytostearyl esters, for example phytostearyl oleate, phytostearyl isostearate and
  • lauroyl/octyldodecyl/phytostearyl glutamate (AJINOMOTO, ELDEW PS203) , triglycerides constituted by esters of fatty acids and glycerol, in particular in which the fatty acids may have chain lengths from C 4 to C 36 , in particular, C 18 to C 36 , said oils possibly being linear or branched, saturated or unsaturated; said oils may in particular be heptanoic or octanoic triglycerides, shea, luzerne, poppy, Hokkaido squash, millet, barley, quinoa, rye,nadooulier, or passiflora oil, shea butter, aloe oil, sweet almond oil, peach kernel oil, peanut oil, argan oil, avocado oil, baobab oil, borage oil, broccoli oil, calendula oil, cameline seed oil, canola oil, carrot oil, carthame oil, hemp oil, rapeseed oil,
  • ca rylic/capric acids such as those sold by the supplier STEARINERIES DUBOIS or those sold under the names MIGLYOL 810 ® , 812 ® and 818 ® by the supplier DYNAMIT NOBEL;
  • ⁇ linear or branched hydrocarbons of mineral or synthetic origin such as paraffin oils and derivatives thereof, Vaseline, polydecenes, polybutenes, or
  • R 1 COOR 2 in which R 1 represents a residue of a linear or branched fatty acid containing 1 to 40 carbon atoms, and R 2 represents a hydrocarbon chain, in particular branched containing 1 to 40 carbon atoms provided that R 1 + R 2 is ⁇ 10.
  • the esters may in particular be selected from esters of an alcohol and a fatty acid, such as, for example: cetostearyl octanoate, esters of isopropyl alcohol such as isopropyl myristate, isopropyl palmitate, ethyl palmitate, 2-ethyl-hexyl palmitate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, diisopropyl adipate, heptanoates, in particular isostearyl heptanoate, octanoates,
  • decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, ethyl 2-hexyl 4-diheptanoate and palmitate, alkyl benzoate, polyethylene glycol
  • diheptanoate propylene glycol 2 -diethyl hexanoate, and mixtures thereof, C 12 -C 15 alcohol benzoates, hexyl laurate, esters of neopentanoic acid, such as isodecyl
  • neopentanoate isotridecyl neopentanoate, isostearyl neopentanoate , octyldodecyl neopentanoate, esters of isononanoic acid such as isononyl isononanoate,
  • hydroxyl esters such as isostearyl lactate or di- isostearyl malate
  • esters of polyols and esters of pentaerythritol such as dipentaerythritol
  • esters of dimeric diols and dimeric diacids such as Lusplan DD-DA5 ® and Lusplan DD-DA7 ® , sold by the supplier nippon fine chemical and described in
  • copolymers of dimeric diols and dimeric diacids and esters thereof such as copolymers of dilinoleyl diol dimers / dilinoleic dimers and esters thereof, such as, for example Plandool-G;
  • copolymers of polyols and dimeric diacids and esters thereof such as Hailuscent ISDA, or dilinoleic acid/butanediol copolymer;
  • a branched and/or unsaturated chain containing 12 to 26 carbon atoms such as 2- octyldodecanol , isostearyl alcohol, oleic alcohol, 2- hexyldecanol , 2-butyloctanol or 2-undecylpentadecanol;
  • oils with a high molar mass in particular a molar mass from approximately 400 to approximately 10000 g/mol, in particular from approximately 650 to approximately 10000 g/mol, in particular from approximately 750 to approximately 7500 g/mol, and more particularly from approximately 1000 to approximately 5000 g/mol.
  • High molar mass oils that may be used in the present invention that may in particular be mentioned are oils selected from:
  • esters of branched C 2 -C 28 fatty acids or fatty alcohols • esters of branched C 2 -C 28 fatty acids or fatty alcohols ;
  • hydrocarbonaceous and/or siliconaceous such as
  • fluorosilicone oils fluorinated polyethers or
  • fluorinated silicones such as those described in the document EP-A-0 847 752;
  • silicone oils such as non-volatile, linear or cyclic polydimethylsiloxanes (PDMS) ,
  • polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups that may be pendent or at the end of the silicon chain, groups containing 2 to 24 carbon atoms; phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl
  • composition in accordance with the invention may further comprise at least one pasty compound.
  • Said compound may advantageously be selected from lanolin and derivatives thereof; polymeric or non- polymeric silicone compounds; polymeric or non-polymeric fluorinated compounds; vinyl polymers, in particular olefin homopolymers ; olefin copolymers; homopolymers and copolymers of hydrogenated dienes; linear or branched oligomers, homo or copolymers of alkyl (meth) acrylates preferably containing a C 8 -C 30 alkyl group; homo- and copolymeric oligomers of vinyl esters containing C 8 -C 30 alkyl groups; homo- and copolymeric oligomers of vinyl ethers containing C 8 -C 30 alkyl groups; liposoluble
  • esters of a glycerol oligomer in particular diglycerol esters, such as polyglyceryl-2 triisostearate,
  • condensates of adipic acid and glycerol wherein a portion of the hydroxyl groups of the glycerols has been reacted with a mixture of fatty acids such as stearic acid, capric acid, stearic and isostearic acid and 12- hydroxystearic acid, especially similar to those sold with reference Softisan 649 by the supplier Sasol or such as bis-diglyceryl polyacyladipate-2 ; arachidyl propionate sold in particular with reference Waxenol 801 by the supplier Alzo; phytosterol esters; triglycerides of fatty acids and derivatives thereof, such as hydrogenated coco- glycerides; uncured polyesters resulting from
  • polycarboxylic acid of an aliphatic hydroxycarboxylic acid ester, said ester comprising at least two hydroxyl groups, such as the products isocast DA-H ® , and Risocast DA-L ® ; and mixtures thereof.
  • the pasty compound or compounds may be present in the composition of the invention in a quantity in the range 0.1% to 30% by weight, preferably in the range 0.5% to 20% by weight, relative to the total composition weight .
  • a composition of the invention may comprise at least one powdered phase, said powdered phase in particular comprising at least one filler, and advantageously also at least one emissive material as defined above and/or at least one pigment.
  • compositions in the form of powders in particular pressed powders.
  • fillers means particles of any shape, colorless or white, mineral or synthesized, insoluble in the medium for the composition irrespective of the temperature at which the composition is manufactured.
  • the fillers may be mineral or organic, of any shape, be they flake, spherical or oblong, irrespective of its crystallographic form (for example flake, cubic,
  • microspheres such as those formed from polyvinylidene chloride /acrylonitrile, such as Expancel ® (Nobel
  • acrylic acid copolymers acrylic acid copolymers, silicone resin microbeads (Tospearls ® from the supplier Toshiba, for example), particles of polyorganosiloxane elastomers, precipitated calcium carbonate, magnesium carbonate and bicarbonate, hydroxyapatite , barium sulfate, aluminum oxides, polyurethane powders, composite fillers, hollow silica microspheres, glass or ceramic microcapsules, metallic salts derived from organic carboxylic acids containing 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate, or magnesium myristate.
  • At least one filler is used selected from kaolin, polyamide powders (Nylon) , copolymers of acrylic acid, and mixtures
  • the filler or fillers may be present in a
  • composition according to the invention in a total quantity of fillers in the range 0.1% to 96% by weight relative to the total weight of the composition,
  • the filler or fillers may generally be present in a quantity in the range 0.1% to 20% by weight, preferably in the range 0.5% to 15% by weight relative to the total composition weight, in particular 1% to 7% by weight relative to the total composition weight.
  • the filler or fillers may generally be present in a quantity in the range 50% to 96% by weight, in particular in the range 70% to 85% by weight, preferably in the range 75% to 80% by weight relative to the total
  • composition of the invention may comprise one or more pigments or colorizing agents.
  • pigments should be understood to mean particles in any form, white or colored, mineral or organic, insoluble in the physiological medium, intended to color the composition.
  • the pigments may be white or colored, mineral and/or organic.
  • Mineral pigments that may be mentioned include titanium dioxide, optionally surface treated, oxides of zirconium or cerium, as well as oxides of zinc, iron (black, yellow or red) or of chromium, manganese violet, ultramarine blue, chromium hydrate and ferric blue, powdered metals such as aluminum powder, and copper powder .
  • Organic pigments that may be used that may be mentioned are carbon black, D & C type pigments and lakes, especially lakes based on carmine and cochineal, barium, strontium, calcium and aluminum.
  • Opaque pigments such as iron oxides, for example, may be present in the composition of the invention in a quantity in the range 0.1% to 15% by weight relative to the total composition weight, preferably in the range 0.5% to 10% by weight, and preferably in the range 1% to 10% by weight.
  • composition of the invention may comprise an additional powdered colorizing material that is different from the pigments described above, and may in particular be selected from nacres and other interference pigments, flakes and mixtures thereof.
  • the nacres may be selected from white nacres such as mica coated with titanium or bismuth oxychloride, colored nacres such as mica titanium coated with oxides of iron, in particular mica titanium coated with ferric blue or chromium oxide, mica titanium coated with an organic pigment of the above-mentioned type and nacres based on bismuth oxychloride.
  • the nacres may be present in a composition in accordance with the invention in a quantity in the range 0.1% to 50% by weight relative to the total composition weight, preferably in the range 0.1% to 40% by weight, and more preferably in the range 0.1% to 30% by weight.
  • the colorizing agents may be selected from those listed in Annex 4 of the European Cosmetics Directive and those listed by the FDA as authorized for cosmetics.
  • composition according to the invention may be any composition according to the invention.
  • the liquid fatty phase selected from a wax, a silicone resin and mixtures thereof.
  • wax as used in the context of the present invention means a lipophilic fatty compound that is solid at ambient temperature (25°C) and atmospheric pressure (760 mm Hg, i.e. 10 5 Pa), with a reversible solid/liquid change of state, in particular having a melting
  • the waxes may be present in the composition in accordance with the invention in a quantity in the range 0.1% to 15% by weight relative to the pulverulent phase, preferably in the range 1% to 8%.
  • the values for the melting point in accordance with the invention correspond to the melting peak measured using a differential scanning calorimeter (DSC) , for example the calorimeter sold under the name DSC 30 by the supplier METLER, with a temperature rise rate of 5°C or 10°C per minute.
  • DSC differential scanning calorimeter
  • the waxes may be those generally used in the cosmetic or dermatological fields.
  • they may be hydrocarbons,
  • silicone and/or fluorinated optionally comprising ester or hydroxyl functions. They may also be of natural or synthetic origin.
  • waxes of animal origin such as beeswax, vegetable waxes such as carnauba, candellila, ouricury, Japan wax;
  • mineral waxes for example paraffin wax, or microcrystalline waxes or ozokerites
  • silicone waxes in particular substituted linear polysiloxanes ; mention may be made, for example, of silicone polyether waxes, alkyl or alkoxy-dimethicones containing 16 to 45 carbon atoms, and alkyl methicones such as C 30 -C 45 alkyl methicone sold under the trade name
  • hydrogenated oils that are solid at 25°C such as hydrogenated castor oil, hydrogenated jojoba oil,
  • the wax present in the composition of the invention may be completely or partially in the powder form, in particular micronized, to facilitate its use in the preparation of the cosmetic composition, especially when it is in the form of a powder.
  • waxes that may be used in the powder form that may be mentioned are carnauba wax microbeads sold under the name Microcare 350 ® by the supplier Micro Powders and paraffin wax microbeads sold under the name Microease 1143 ® by the supplier Micro Powders. Such additional micronized waxes may in particular improve the properties during application of the composition to the skin.
  • the pulverulent phase of a composition of the invention may further comprise at least one silicone resin.
  • Silicone resins are the products of hydrolysis and polycondensation of mixtures of siloxanes with formulas (R) 3 SiOCH 3 and Si(OCH 3 ) 4 , R representing an alkyl group containing 1 to 6 carbon atoms .
  • silicone resins are known or can be prepared using known methods. Examples of commercially available silicone resins that may be mentioned are those sold under the names KSP 100 (SHIN ETSU) .
  • the silicone resin may be present in a quantity in the range 0.1% to 35% by weight relative to the total weight of the pulverulent phase .
  • composition in accordance with the invention may comprise any other ingredients (adjuvant) that is in routine use in cosmetics such as thickening or gelling agents, film-forming polymers, vitamins, oligo-elements, softeners, sequestrating agents, fragrances, alkalinizing or acidifying agents, preservatives, sunscreens,
  • ingredients such as thickening or gelling agents, film-forming polymers, vitamins, oligo-elements, softeners, sequestrating agents, fragrances, alkalinizing or acidifying agents, preservatives, sunscreens,
  • the nanospheres were synthesized using the protocols described by G. Chumanov, Chem. Phys. Chem. , 2005, 6, 1221 - 1231; J. Phys . Chem. B, 2004, 108, 1522 - 1524; Nano Lett. 2001, 1, 647 - 649; J. Am. Chem. Soc . 1999, 121, 10642 - 10643; H.C. Gerritssen, Adv. Matter., 2006, 18, 91 - 95; A. van Blaaderen, Langmuir, 2003, 19, 6693 - 6700; Langmuir, 2003, 19, 1384 - 1389.
  • the gold, spherically shaped nanospheres with a diameter of 5 nm, 50 nm, 80nm, 100 nm, 200 nm were supplied by the supplier Ted Pella Inc.
  • the silver, spherically shaped nanospheres with a diameter of 20 nm, 40 nm, 60 nm, 80 nm, lOOnm, llOnm were supplied by the supplier Ted Pella Inc.
  • Protocol 1 Synthesis of Ag@SiO 2 and Au@SiO 2 nanospheres
  • aqueous solution of poly (vinylpyrrolidone) PVP with a molar mass of 360 kg/mol and an aqueous suspension of spherical noble metal (gold or silver) colloids with a diameter d (rim) were mixed at ambient temperature for 24h under vigorous agitation.
  • the quantity of PVP was calculated such that the number of PVP molecules was approximately 60 per nm 2 .
  • the liquid supernatant was withdrawn.
  • the colloids were then dispersed in an ethanolic solution of ammonia (4.2%v/v) and an ethanolic solution of tetraethoxysilane (TEOS) , 10%v/v, was introduced at ambient temperature with vigorous agitation.
  • TEOS hydrolysis reaction was of a duration of 12 h at ambient temperature then the dispersed colloids obtained were centrifuged and washed with water three times then re-dispersed in 20 mL of water.
  • the relative concentration of TEOS allowed the thickness of the silica shell to be controlled.
  • TEOS tetraethoxysilane
  • Protocol 3 Synthesis of Ag@PMMA and Au@PMMA nanospheres
  • Protocol 4 Synthesis of Ag@PVP and Au@PVP nanospheres
  • (3-aminopropyl) triethoxysilane APTES was added under vigorous agitation to a suspension of Ag@SiO 2 or Au@SiO 2 nanosp eres, in deionized water at ambient temperature. After 30 min of reaction, the suspension of thus
  • a phenyltriethoxysilane (PTES) /tetraethoxysilane (TEOS) mixture was added under vigorous agitation to a suspension of Ag@SiO 2 or Au@SiO 2 nanospheres in deionized water at ambient temperature. After 30 minutes of reaction, the suspension of colloids was centrifuged and washed three times with deionized water, then taken up into suspension in deionized water. 5 equivalents of fluorophore dissolved in ethanol was then added dropwise to this aqueous suspension and at ambient temperature and agitated for 30 minutes. After leaving to stand for 24 h and at a temperature of 4°C, the suspension was
  • Examples 11 and 12 particulate materials with structure (ID : 1 st step; Preparation of C-D-E of Figure 5, namely a silica core coated with metal and a silica shell.
  • a triplet of values for example 250, 270, 290, denotes a structure where r 1 , r 2 and r 3 are respectively 250 ran, 270 nm, and 290 nm.
  • the silica nanospheres with a diameter in the range 50 nm to 300 nm were produced using the protocol described by W. Stober, J. Colloid Interface Science, 26, 62 - 69, 1968 by hydrolyzing
  • TEOS tetraethoxysilane
  • a saturated basic ammonium hydroxide solution in a lower alcohol such as ethanol or a 3 : 1 mixture of propanol : methanol at ambient
  • reaction medium was then allowed to return to ambient temperature and the ethanol and ammonia were evaporated off under reduced pressure. After repeated washing with ethanol, 1 g of powder corresponding to silica
  • nanospheres 250 ⁇ 10 nm in diameter were isolated.
  • SiO 2 @Au silica nanospheres enveloped with a continuous shell of gold with a thickness of 40 + 5 nm were obtained and were redispersed in 10 mL of water.
  • the SiO 2 @Au nanospheres in aqueous dispersion were introduced into pure ethanol at ambient temperature and with vigorous agitation.
  • a 30% solution of ammonium hydroxide along with a tetraethylsiloxane (TEOS) solution were simultaneously added to this dispersion, with vigorous agitation for 1 h.
  • the quantity of TEOS added was adjusted so as to control the thickness of the silica shell obtained around the SiO 2 @Au nanospheres.
  • SiO 2 @Au@SiO 2 nanospheres were centrifuged and washed several times with water then redispersed in 20 mL of water.
  • Protocol 9 Production of [SiO 2 @Ag@SiO 2 ] 250,280,300 and [SiO 2 @Ag@SiO 2 ] 25o,290,310 nanospheres :
  • silica nanospheres with a diameter of 50 nm to 300 nm were produced using the protocol described by W. Stober, J. Colloid Interface Science, 26, 62 - 69, 1968 and Y. Zhang, Chinese Chem. Lett., 15, 8, 1005 - 1008, 2004 by introducing an ethanolic solution of tetraethoxysilane (TEOS) into a basic solution of 25% w/w ammonium hydroxide in a lower alcohol such as ethanol or a 3:1 mixture of propanol : methanol at ambient temperature and with mechanical agitation. The mixture was agitated for 1 h at ambient temperature and the silica colloids obtained were left to stand for 24 h. After evaporating off the ethanol and ammonia under reduced pressure, then washing with ethanol three times, SiO 2 nanospheres with a diameter of 250 ⁇ 10 nm were obtained.
  • TEOS tetraethoxysilane
  • the silica nanospheres obtained were mixed with a 1:9 water : ethanol solution containing silver nitrate AgN0 3 in a concentration of 0.1% under vigorous agitation.
  • a 1:9 water : ethanol solution containing silver nitrate AgN0 3 in a concentration of 0.1% under vigorous agitation.
  • an excess of an ethanolic solution of ammonium citrate was slowly introduced.
  • the dispersion was left to stand for 24 h then centrifuged and washed with water three times to eliminate the residual reagents and to produce SiO 2 @Ag nanospheres redispersed in 10 mL of water.
  • TEOS tetraethoxysilane
  • (3-aminopropyl) triethoxysilane APTES was added to a suspension of SiO 2 @Au@SiO 2 or SiO 2 @Ag@SiO 2 nanospheres in deionized water, with vigorous agitation, at ambient temperature. After reacting for 30 minutes, the
  • TEOS TEOS
  • SiO 2 @Au@SiO 2 or SiO 2 ®Ag@SiO 2 nanospheres were added to a suspension of SiO 2 @Au@SiO 2 or SiO 2 ®Ag@SiO 2 nanospheres in deionized water, with vigorous agitation at ambient temperature.
  • compositions were prepared using conventional methods known to the skilled person with the particulate materials as described above.

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Abstract

La présente invention a pour objet une composition cosmétique comprenant : - un premier composé fluorophore ayant un spectre d'absorption ; et - un second composé fluorophore ayant un spectre d'émission chevauchant le spectre d'absorption du premier composé fluorophore, au moins l'un des deux composés fluorophores ayant une luminescence accrue par un effet d'interaction de proximité avec au moins un métal, le métal et le composé fluorophore faisant partie d'une seule et même particule.
PCT/IB2011/050281 2010-01-21 2011-01-21 Composition cosmétique comprenant au moins un composé fluorophore Ceased WO2011089571A2 (fr)

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