WO2014083126A1 - Treatment of organic and inorganic pigments by means of a method using natural plant oils - Google Patents

Treatment of organic and inorganic pigments by means of a method using natural plant oils Download PDF

Info

Publication number
WO2014083126A1
WO2014083126A1 PCT/EP2013/075009 EP2013075009W WO2014083126A1 WO 2014083126 A1 WO2014083126 A1 WO 2014083126A1 EP 2013075009 W EP2013075009 W EP 2013075009W WO 2014083126 A1 WO2014083126 A1 WO 2014083126A1
Authority
WO
WIPO (PCT)
Prior art keywords
pigment
red
surface modification
vegetable oil
natural vegetable
Prior art date
Application number
PCT/EP2013/075009
Other languages
French (fr)
Inventor
Franck Martin
Guillaume GRACY
Aude MEZY
Adeline GARCIA
Original Assignee
Sikemia
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 Sikemia filed Critical Sikemia
Publication of WO2014083126A1 publication Critical patent/WO2014083126A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/36—Compounds of titanium
    • C09C1/3607—Titanium dioxide
    • C09C1/3669—Treatment with low-molecular organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0009—Coated particulate pigments or dyes with organic coatings containing organic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/04—Compounds of zinc
    • C09C1/043—Zinc oxide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/22—Compounds of iron
    • C09C1/24—Oxides of iron
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/22—Compounds of iron
    • C09C1/26—Iron blues
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/34—Compounds of chromium
    • C09C1/346—Chromium oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C09D7/62—Additives non-macromolecular inorganic modified by treatment with other 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
    • A61K2800/10—General cosmetic use
    • 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
    • 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
    • A61K2800/622—Coated by organic compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/62—L* (lightness axis)
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/63—Optical properties, e.g. expressed in CIELAB-values a* (red-green axis)
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/64—Optical properties, e.g. expressed in CIELAB-values b* (yellow-blue axis)
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/65—Chroma (C*)

Definitions

  • the subject of the invention is a process for modifying the surface of an organic or inorganic pigment using a natural vegetable oil as well as the pigment compositions obtained by such a process, especially in the form of a powder.
  • the invention also includes the use of these pigments or pigment compositions for cosmetics, dermatology, paints or inks.
  • Organic pigments as well as inorganic pigments can be used for their coloring power in cosmetics, but also in paints and inks. In general, presented in the form of a powder, these pigments are asked to be able to disperse homogeneously with the desired color rendition and while having a good stability when formulated for these different fields of use.
  • the processes proposed are for the most part applicable to inorganic pigments and / or use synthetic lipid derivatives of animal or mineral origin and / or comprise one or more heating stages at high temperature (greater than 100 ° C) poorly adapted to more unstable organic pigments.
  • such processes are difficult to apply when it is desired to use natural oils of plant origin comprising unsaturated fatty acids often unstable at these temperatures.
  • the object of the present invention is therefore to provide an organic or inorganic pigment whose surface has been modified, in a dry or dispersed form in a solvent, of high dispersancy and stability, and of good tactile quality, by a process simple and easy to implement and applicable to both organic and inorganic pigments, in the possible presence of excipients.
  • compositions according to the present invention are identical to the compositions according to the present invention.
  • the inventors have thus been able to demonstrate that the process according to the invention as described below and using a natural vegetable oil, in particular when the natural vegetable oil / solvent mixture is vaporized on the surface of the pigments to be treated to give them the desired characters, makes it possible to obtain these pigments with such properties as in particular better dispersion and storage stability in dry form or in formulation and removal of the aqueous phase bleeding phenomenon for organic pigments.
  • the invention relates to a method of modifying the surface of an inorganic or organic pigment, said method comprising the following steps:
  • step C) the drying is carried out at a temperature less than or equal to 100 ° C and greater than the solidification point of said natural vegetable oil.
  • the drying is carried out at a temperature of between 40 ° C. and 80 ° C., preferably greater than or equal to 12 hours at 80 ° C., greater than or equal to 18 hours at 60 ° C. or greater than or equal to 24 hours for 40 ° C.
  • the surface modification method of a pigment according to the present invention is characterized in that the pigment is organic, and said process comprises the following steps:
  • step C) the drying is carried out at a temperature less than or equal to 100 ° C and greater than the solidification point of said vegetable oil, preferably the drying is carried out at a temperature between 40 ° C and 80 ° C as indicated above.
  • the surface modification method according to the present invention is characterized in that prior to step A, said natural vegetable oil or said pigment is mixed with a solvent.
  • said solvent is characterized in that it is chosen from "green" (non-toxic) solvents or organic solvents.
  • said solvent is selected from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol. More preferably, this aqueous solvent may thus contain water, alcohols, a mixture of water and alcohol.
  • the alcohols may be chosen in particular from lower linear or branched monoalcohols having from 2 to 5 carbon atoms, such as ethanol, propanol, isopropanol or butanol, but also polyols such as glycerol, diglycerol or propylene glycol. sorbitol, penthenol, penthylene glycol, polyethylene glycols.
  • the process is devoid of additional surface modifying agent than natural vegetable oil and optionally solvent.
  • non-toxic solvents in particular, but not limited to, cosmetically acceptable solvents, preferably chosen from the group consisting of the following “green” (non-toxic) solvents: Ethanol, Water, Ethanol / Water mixture in proportions ranging from 100% / 0% to 0% / 100%.
  • the proportions of the relative mass mixture Ethanol / water may for example be between 1% / 99% and 99% / 1%, between 2% / 98% and 98% / 2%, between 3% / 97% and 97% / 3%, between 4% / 96% and 96% / 4%, between 5% / 95% and 95% / 5%, between 10% / 90% and 90% / 10%, between 20% / 80% and 80% / 20%, between 30% / 70% and 70% / 30%, between 40% / 60% and 60% / 40%, or be approximately equal to 50% / 50% (ie say more or less 5%).
  • the mass proportion of one or the other of these solvents may be predominant, that is to say greater at 50% / 50%, greater than or equal to 60% / 40%, 70% / 30%, 80% / 10%, 90% / 10%, 95% / 5%, 96% / 4%, 97% / 3%, 98% / 2%, or 99% / 1%.
  • the liquid-gas mixture can be made by generating a rotating device sprayer, electrostatic spraying, ultrasonic spraying, etc.
  • the techniques for implementing all these nozzles are well known to those skilled in the art.
  • the presence of gas is not mandatory in certain specific cases.
  • the invention is at atmospheric pressure or reduced pressure.
  • natural vegetable oils having high boiling points the vaporization will often consist of the suspension of very fine droplets of these oils, and / or their mixtures (optionally with one or more solvents) in a "carrier" carrier gas, according to the technique used.
  • carrier gas a carrier gas
  • the carrier gas may be of any chemical nature suitable for this implementation and will preferably be inert, such as argon, nitrogen, helium, etc.
  • spray spraying (very fine droplets) through one or more spray nozzles will be preferred.
  • other vaporization techniques exist and are applicable to the present invention such as chemical vapor deposition ("CVD” or “chemical vapor deposition” in English), physical vapor deposition (“PVD” or “physical vapor deposition”).
  • vapor deposition ") molecular beam epitaxy, plasma deposition, pulsed laser deposition, sol-gel deposition, electrochemical deposition, the use of an ultrasonic nebulizer or electrostatic deposition. All of these techniques and their implementation are well known in the art.
  • these pigments will be mixed, for example by means of an internal mixer equipped with a thermoregulator. During spraying, bringing the entire surface of the pigments into contact with the emulsion is thus more homogeneous.
  • the emulsion-pigment mixture is in the form of a powder.
  • the surface modification method according to the present invention is characterized in that said pigment in step A) is in powder form.
  • the surface modification method according to the present invention is characterized in that said natural vegetable oil is previously solubilized or emulsified in a solvent.
  • the natural vegetable oil is not subjected to treatment conditions which would modify structurally (ie the chemical structure of its constituents) the compounds it contains, such as a hydrogenation, or still a refining.
  • the surface modification method according to the present invention is characterized in that said natural vegetable oil is previously solubilized or emulsified in a solvent in a weight to mass ratio of between 1% and 100%, preferably between 20% and 80%, between 40% and 60%, the most preferred being close to 50% (plus or minus 5%).
  • the surface modification method according to the present invention is characterized in that the mass ratio between said natural vegetable oil and said pigment is less than 50%, preferably between 1% and 30%, between 1% and 10%, the most preferred being close to 3% (plus or minus 1%). ("Dry Way").
  • the surface modification method according to the present invention is characterized in that said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent selected from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol. More preferably, this aqueous solvent may thus contain water, alcohols, a mixture of water and alcohol.
  • the alcohols may be chosen in particular from lower linear or branched monoalcohols having from 2 to 5 carbon atoms, such as ethanol, propanol, isopropanol or butanol, but also polyols such as glycerol, diglycerol or propylene glycol. sorbitol, penthenol, penthylene glycol, polyethylene glycols.
  • the surface modification method according to the present invention is characterized in that said natural vegetable oil previously emulsified or solubilized in a solvent is, in step A), grafted onto the pigment whose surface is to be modified. .
  • the surface modification method according to the present invention is characterized in that the mass ratio between said pigment and said oil natural plant is less than 50%, preferably between 5% and 30%, between 5 and 10%, the most preferred being close to 5% (plus or minus 1%). ("Liquid Way").
  • said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent which may also be chosen from hydrocarbon-type solvents, preferably pentane, hexane, cyclohexane, heptane, when said pigment is of organic origin; and
  • said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent chosen from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol when said pigment is of inorganic origin.
  • a solvent chosen from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol when said pigment is of inorganic origin.
  • This aqueous solvent can thus contain water, alcohols, a mixture of water and alcohol.
  • the alcohols may be chosen in particular from lower linear or branched monoalcohols having from 2 to 5 carbon atoms, such as ethanol, propanol, isopropanol or butanol, but also polyols such as glycerol, diglycerol or propylene glycol.
  • the surface modification method according to the present invention is characterized in that prior to step C), the mixture obtained in step B) is filtered and then, if necessary, washed and / or rinsed off. in order to remove the compounds of the mixture unreacted with said pigment.
  • the surface modification method according to the present invention is characterized in that the steps of washing (and / or rinsing) and recovery of the pigment whose surface has been modified are carried out in the presence of solvent by mechanical separation. (decantation, centrifugation), filtration in depth or on a support, preferably by filtration on a membrane support, by vacuum extraction.
  • the surface modification method according to the present invention is characterized in that said natural vegetable oil contains saturated and / or unsaturated fatty acid triglyceride esters, preferably of length C12 to C24.
  • said surface modification method according to the present invention is characterized in that said natural vegetable oil is preferably chosen from the group of oils consisting preferably of macadamia oil, prickly pear, borage, perilla, olive, jojoba, sweet almond, avocado, buruti, pomegranate, evening primrose, sunflower, green tea and argan, etc.
  • the vegetable oil is selected from the group of oils consisting of macadamia oil, prickly pear, borage, perilla, jojoba, sweet almond, avocado, buruti, pomegranate , evening primrose, sunflower, green tea and argan. More preferably, the vegetable oil is selected from the oil group consisting of sweet almond oil, avocado, buruti, pomegranate, evening primrose, sunflower, green tea and argan. Also preferably, the vegetable oil may be selected from the group consisting of oil of macadamia oil, prickly pear, borage, perilla, jojoba. Jojoba, sweet almond, avocado, sunflower and olive oils are particularly attractive because of their low purchase costs related to their annual production quantities in the industry.
  • the surface modification method according to the present invention is characterized in that said pigment is an organic pigment or a composition comprising an organic pigment, preferably chosen from true pigments, inks or lacquers, preferably the lacquers.
  • said pigment is an organic pigment or a composition comprising an organic pigment, preferably chosen from true pigments, inks or lacquers, preferably the lacquers.
  • the surface modification method according to the present invention is characterized in that said pigment is an organic pigment, or a composition comprising an organic pigment, chosen from (see Example 1A according to Tables 1 to 4 for the structure and examples of composition of these organic pigments).
  • the surface modification method according to the present invention is characterized in that said pigment is an inorganic pigment, preferably consisting of the following different chemical elements: F, Na, Mg, Al, Si, P, S, K, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, or W.
  • said pigment is an inorganic pigment, preferably consisting of the following different chemical elements: F, Na, Mg, Al, Si, P, S, K, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, or W.
  • the surface modification method according to the present invention is characterized in that said pigment is a composite pigment formed of one or more inorganic pigments associated with one or more excipients in the presence or absence of a lacquer, preferably an inorganic pigment selected from the group consisting of the following pigments, Black Iran Oxide, Red Iran Oxide, Yellow Iran Oxide, Violet Manganese, Ultramarine Blue, Titanium Dioxide, Chromium Oxide Green, Zinc Oxide, Blue Iran, Chromium Oxide Hydrated.
  • said excipient is preferably chosen from excipients of natural or synthetic origin, more preferably chosen from the following group:
  • said pigment is a composite pigment formed of one or more inorganic pigments associated with one or more excipients in the presence or absence of a lacquer.
  • said pigment is a composite pigment comprising one or more inorganic pigments, an excipient and, if appropriate, a lacquer chosen from the group consisting of the following composite pigments:
  • mice 59 to 69%), TiO 2 (18 to 28%), Fe 3 O 4 (1 to 6%), FeO (OH) (1 to 2%) and Red7Calcium (8 to 12%);
  • Synthetic fluororphlogopite (23 to 33%), Ti0 2 (57 to 67%) and Red7Calcium (5 to 15%);
  • mice 46 to 56%), TiO 2 (34 to 44%) and Red7Calcium (8 to 12%);
  • mice 48 to 58%, TiO 2 (28 to 38%) and Yellow Aluminum (9 to 19%); Mica (48-58%), Ti0 2 (28 to 38%) and Red6Sodium (9-19%);
  • the present invention relates to a process for preparing a pigment powder or a composition comprising at least one pigment, preferably intended for use in cosmetics, in paint or in inks, preferably in cosmetics, characterized in that it comprises the following steps:
  • step C) a recovery step of said pigment or of said composition comprising at least one pigment whose surface has thus been modified obtained in step C) in the form of a powder.
  • the present invention provides a pigment, fatty acid coated, or pigment powder that can be directly obtained by a surface modification method according to the present invention.
  • the pigment according to the present invention is characterized in that it is coated with fatty acid whose concentration is between 1 and 25% by weight, more preferably between 1% and 10%, between 1% and 7%. , 5% or 1% and 5%.
  • the present invention provides a composition comprising a pigment or a pigment powder according to the present invention, in a mixture with a pharmaceutically or cosmetically acceptable ingredient.
  • the present invention relates to a composition comprising a pigment according to the present invention or powder obtained by the process according to the present invention, intended for use in cosmetics, inks or in paint, preferably in cosmetics.
  • the cosmetic composition according to the present invention is characterized in that it is contained in an eyeshadow, a cheek powder, a lipstick, a cream, a gel, a lipstick stick or a lacquer a lip gloss, a solid foundation, an eye contour, a mascara, an eyeliner, a compacted powder, a blush or a nail polish, a bar of soap or any form of cosmetic product.
  • These compositions may, in addition, contain other active compounds in cosmetics or dermo-cosmetics, in particular to provide a care or treatment aspect to the composition.
  • Another aspect of the invention relates to a composition according to the invention characterized in that the value of dE (colorimetry) remains less than or equal to 2 over a lapse of time of at least 36 months, preferably 24 months, more preferably 18 months, even more preferably 12 months or 6 months.
  • the reference colorimetric values making it possible to calculate the dE are those of the pigment treated at time t0, that is to say the pigment obtained just after the implementation of the process according to the invention.
  • the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C., 5 ° C. C or 0 ° C, preferably for a period of time of 36 months.
  • the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C.
  • the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C. 5 ° C or 0 ° C, preferably for a period of 18 months. Even more advantageously, the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C. 5 ° C or 0 ° C, preferably for a period of 12 months.
  • the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C. 5 ° C or 0 ° C, preferably for a period of time of 6 months.
  • the composition according to the invention having a value of dE remaining less than or equal to 2 over a determined period of time comprises at least one pigment consisting of one or more pigments according to the present invention.
  • one aspect of the invention relates to the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 36 months, preferably 24. month, more preferably 18 months, even more preferably 12 months or 6 months.
  • the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 36 months is at a storage temperature. of said composition to be stabilized less than or equal to 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
  • the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 24 months is at a temperature of storing said composition to be stabilized at or below 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
  • the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 18 months is at a temperature of storing said composition to be stabilized less than or equal to 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
  • the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 12 months is at a temperature of storing said composition to be stabilized less than or equal to 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
  • the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 6 months is at a temperature of storage of said composition to stabilize at or below 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
  • the organic pigments are mainly lacquers.
  • True pigments are organic molecules that precipitate by forming an insoluble organic structure.
  • Inks are obtained by precipitation of a water-soluble dye as a metal salt.
  • the lacquers are obtained by adsorption of a water-soluble dye on an insoluble inorganic substrate.
  • the inorganic pigments are predominantly metal oxides or metal complexes, including one or more of the following chemical elements (F, Na, Mg, Al, Si, P, S, K, Ca, Ti, V, Cr, Mn, Fe, Co , Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, W)) can be used in their composition.
  • the particle size varies between 10 nm and 10 ⁇ .
  • Black iron oxide Fe 3 0 4 or Fe 2 O 3 / FeO: Also called ferrosoferric oxide obtained by reduction of ferric oxide (red). It is stable to light, heat, solvents and acids.
  • Red iron oxide Fe 2 0 3 : Also called ferric oxide, it is a pigment that is stable to light, heat, solvents and acids.
  • Yellow iron oxide Fe 2 0 3 , H 2 0: Also called hydrated ferric oxide, it is a pigment that is stable to light, heat, solvents and acids.
  • Titanium dioxide Ti0 2 : Pigment with a great interest in cosmetics because it is used as a UV filter. It has good resistance to light, heat, solvents and acids.
  • Iron blue FeNH 4 Fe (CN) 6 : Prussian blue mineral pigment, remarkably stable in light, solvents and acids; however, it does not withstand temperatures above 200 ° C.
  • Ultramarine blue Na 6 Al 6 Si 6 0 24 S 4 : Artificial mineral pigment obtained by heating soda, clay and sulfur. It is nontoxic and is resistant to light, heat and solvents; however, it is not very resistant to acids.
  • Purple manganese oxide Mn (NH 4 ) P 2 O 7 : Mineral pigment of violet color with good stability to light, heat, solvents and acids.
  • Green Chromium Oxide Cr 2 0 3 : Olive green pigment remarkably stable to light, heat, chemicals and acids.
  • Green chromium oxide hydrate Cr 2 0 3 , (H 2 0) 2 : Turquoise green pigment having low temperature stability but with good stability to light, acids and solvents.
  • Zinc oxide Zinc oxide: ZnO
  • Composite pigments formed from one or more inorganic pigments, an excipient and optionally a lacquer see Tables 6 and 7)
  • Excipients they can be of natural or synthetic origin and fit particularly into the composition of composite pigments and lacquers.
  • the major fatty acids in the composition of the oils are:
  • Example 3 Dry method The principle of this process is grafting by bringing the coupling agent into contact with the pigments (substrates) .
  • the pigments thus treated can be organic or inorganic. This process also makes it possible to treat the excipients and effect pigments. The process takes place in three stages:
  • An emulsion is prepared by mixing one or more vegetable oils with a selected solvent. The preparation of this mixture can be made in temperature.
  • the emulsion is then completely vaporized on the pigments to be treated.
  • the mass percentage of the vegetable oil in solution varies according to the couple (vegetable oil / pigment to be treated). It is generally considered sufficient from 1%.
  • the choice of the solvent water (H 2 0), ethanol (EtOH) or mixture
  • H 2 0 / EtOH also varies according to the pair Natural vegetable oil / Pigment.
  • the entire surface of the pigments is brought into contact with the emulsion by means of an internal mixer equipped with a thermoregulator so that this bringing into contact is homogeneous.
  • the emulsion + pigment mixture is in the form of a powder.
  • the emulsion mixture (vegetable oil naurelle / solvent) + pigment is heated to a temperature between 40 and 100 ° C.
  • Example 4 Process called by liquid route
  • the natural vegetable oil is grafted onto the surface of the substrate (pigment) by immersing the substrate in a solution or emulsion containing the natural vegetable oil.
  • the functionalized substrate is then extracted from the grafting solution and then dried.
  • the grafting takes place in three stages:
  • the grafting step is carried out by chemical reaction between the natural vegetable oil at the desired concentration and the surface of a pigment to be modified, in the chosen solvent (EtOH, H 2 O or H 2 O / EtOH mixture) during a desired time.
  • EtOH EtOH, H 2 O or H 2 O / EtOH mixture
  • a solution / emulsion of natural vegetable oil is prepared by dissolving the natural vegetable oil in 10 ml of solvent.
  • the mass percentage of natural vegetable oil of the solution / emulsion varies between 1% and 50% (natural vegetable oil chosen / substrate to be treated).
  • the choice of the solvent also varies according to the natural vegetable oil / substrate pair. Conventional organic solvents can also be used, but current environmental considerations tend to diminish their use.
  • pigments is placed (substrate) in a pill box to which is added 10 ml of solution / emulsion of natural vegetable oil.
  • Static condition The chemical reaction occurs without magnetic stirring preferably at room temperature (10-35 ° C) for a time t.
  • the graft solution / emulsion not fixed on the pigments is removed by filtration and the material (modified substrate) is washed to ensure the complete elimination of all physisorbed elements.
  • the solution contained in the pill pillar is transferred to a centrifuge tube and then filled in with EtOH.
  • the centrifuge tube is refilled at 3 ⁇ 4 with EtOH and placed in an ultrasonic tank for 10 minutes.
  • the solution is then centrifuged under the same conditions.
  • the functionalized pigment powders (substrates) are transferred to a glass pill and dried for 12 hours.
  • the temperature of the oven varies between 20 and 100 ° C depending on the tolerance of the different substrates and coupling agents to the thermal conditions.
  • Finished Products Inorganic pigments and treated organic pigments having a hydrophobic character, tactile qualities as well as good dispersibility in the oily phase. Organic treated pigments having a very low or non-existent deposition in the aqueous or fatty phases.
  • the invention makes it possible to treat with the same coupling agent and by the same process a wide variety of inorganic pigment substrates (metals, metal oxides, etc.), organic pigments, excipients and composite pigments.
  • This process according to the present invention makes it possible to treat organic pigments, in particular at a low temperature compatible with these pigments, and the cosmetically and dermo-cosmetically acceptable natural vegetable oils that it is desired to use.
  • This process according to the present invention makes it possible to limit the quantities of reagents (coupling agents) and of solvent used.
  • This process according to the present invention makes it possible to use several processes ("dry” route, liquid route, ultrasound).
  • the "dry process” method according to the invention implementing the vaporization and mixing step is particularly preferred, this method also making it possible to graft onto the surface of the pigments the agents responsible, among other things, for the hydrophobicity property contained in natural vegetable oils.
  • the grafting processes are carried out under conditions that are easier than those of the prior art, for example under ambient, non-anhydrous conditions, which makes it possible to avoid the use of organic solvents.
  • This process according to the present invention uses so-called “safe” solvents and natural vegetable oils, which makes it possible to envisage an ecocert labeling for the treated pigments or the finished cosmetic products.
  • the prior art states that the hue of the pigments is impaired when the fatty acid derivatives, fatty acid ester or trigyceride coupling agents are used alone or in the presence of non-hydrogenated phospholipids. or metal salts, the method as established, using natural vegetable oils with a drying step C whose temperature is between 20 and 100 ° C limits the alterations in the hue of the pigments (see Table 22).
  • Example 5 Example of achievements:

Abstract

The invention relates to a method for modifying the surface of an organic or inorganic pigment, using a natural plant oil as well as the pigment compositions resulting from such a method, particularly in powder form. The invention also relates to the use of said pigments or pigment compositions for cosmetics, paint, or inks.

Description

TRAITEMENTS DES PIGMENTS ORGANIQUES ET INORGANIQUES PAR UN PROCEDE METTANT EN ŒUVRE DES HUILES VEGETALES NATURELLES  TREATMENTS OF ORGANIC AND INORGANIC PIGMENTS BY A PROCESS USING NATURAL VEGETABLE OILS
L'invention a pour objet un procédé de modification de surface d'un pigment organique ou inorganique mettant en œuvre une huile végétale naturelle ainsi que les compositions de pigments obtenus par un tel procédé, notamment sous forme de poudre. The subject of the invention is a process for modifying the surface of an organic or inorganic pigment using a natural vegetable oil as well as the pigment compositions obtained by such a process, especially in the form of a powder.
L'invention comprend également l'utilisation de ces pigments ou compositions de pigments pour la cosmétique, la dermatologie, la peinture ou encore les encres.  The invention also includes the use of these pigments or pigment compositions for cosmetics, dermatology, paints or inks.
Les pigments organiques au même titre que les pigments inorganiques peuvent être utilisés pour leur pouvoir colorant dans les produits cosmétiques, mais également dans les peintures et dans les encres. En général, présentés sous forme d'une poudre, il est demandé à ces pigments de pouvoir se disperser de manière homogène avec le rendu de couleur souhaité et tout en ayant une bonne stabilité lorsqu'ils sont formulés pour ces différents domaines d'utilisation. Organic pigments as well as inorganic pigments can be used for their coloring power in cosmetics, but also in paints and inks. In general, presented in the form of a powder, these pigments are asked to be able to disperse homogeneously with the desired color rendition and while having a good stability when formulated for these different fields of use.
Malheureusement, ces pigments tendent naturellement à s'agréger ou à floculer de part leur taille, leur forte densité et leur affinité naturelle. Cet inconvénient rend difficile leur stockage et leur conservation sous forme brute après leur production, en particulier lorsqu'ils sont conservés sous forme de poudre avant leur formulation et leur utilisation finale.  Unfortunately, these pigments naturally tend to aggregate or flocculate because of their size, high density and natural affinity. This disadvantage makes it difficult for them to be stored and preserved in their raw form after production, in particular when they are stored in powder form before being formulated and finally used.
De surcroît, les pigments organiques qui peuvent présenter l'avantage de conférer aux formulations des couleurs vives, présentent l'inconvénient de dégorger en phase aqueuse et par exemple dans le domaine cosmétique de tacher la peau ou les ongles de manière disgracieuse après application.  In addition, the organic pigments which may have the advantage of giving the formulations bright colors have the disadvantage of disgorging in aqueous phase and for example in the cosmetic field to stain the skin or nails unsightly after application.
Ainsi, il est souhaitable de pouvoir améliorer la dispersion et la stabilité de pigments organiques et inorganiques, que ce soit dans des solvants compatibles avec leur utilisation cosmétique, comme les solvants aqueux, ou dans d'autres solvants compatibles avec leur destination finale, mais également de pouvoir améliorer leur stabilité lorsqu'ils sont conservés sous forme sèche avec une bonne capacité de dispersion dans le solvant qui sera utilisé dans la formulation finale. Parmi les procédés permettant d'améliorer la dispersion et la stabilité de pigments inorganiques, on peut citer en particulier les procédés dans lesquels la surface de ces pigments est rendue particulièrement hydrophobe au moyen de réactifs de synthèse, tels que des réactifs bi-fonctionnels, des dérivés siliconés qui selon certaines conditions sont capables de se greffer à la surface ou de revêtir la surface de ces pigments, et de modifier ainsi les propriétés de surface et de comportement de ces pigments lorsqu'ils sont sous forme de poudre ou en suspension dans les solvants qui seront utilisés dans les formulations finales. On peut citer par exemple les réactifs de type N-acylamino- acide (voir le document brevet US ,606,914). Thus, it is desirable to be able to improve the dispersion and the stability of organic and inorganic pigments, whether in solvents compatible with their cosmetic use, such as aqueous solvents, or in other solvents compatible with their final destination, but also to be able to improve their stability when they are kept in dry form with a good dispersion capacity in the solvent which will be used in the final formulation. Among the processes making it possible to improve the dispersion and the stability of inorganic pigments, mention may be made in particular of processes in which the surface of these pigments is rendered particularly hydrophobic by means of synthetic reagents, such as bifunctional reagents, silicone derivatives which under certain conditions are capable of grafting onto the surface or coating the surface of these pigments, and thus modify the surface and behavior properties of these pigments when they are in powder form or suspended in the solvents that will be used in the final formulations. For example, N-acylamino acid reagents can be mentioned (see US patent 606,914).
On peut également citer les procédés mettant en œuvre des dérivés d'acides gras, d'ester d'acides gras ou de trigycérides seuls ou en présence de phospho lipides non- hydrogénés ou de sels métalliques (voir documents W095/11943, US 4,627,876 US 4,648,908, US 4,863,800 ou encore EP 0 477 622 Bl).  It is also possible to use processes using fatty acid, fatty acid ester or trigyceride derivatives alone or in the presence of non-hydrogenated phospho lipids or of metal salts (see documents WO95 / 11943, US 4,627,876 US 4,648,908, US 4,863,800 or EP 0 477 622 B1).
En général, les procédés proposés s'appliquent en grande majorité aux pigments inorganiques et/ou mettent en oeuvre des dérivés lipidiques de synthèse, d'origine animale ou minérale et/ou comportent une ou plusieurs étapes de chauffage à température élévée (supérieure à 100 °C) peu adaptée aux pigments organiques plus instables. De plus, de tels procédés sont difficilement applicables lorque l'on souhaite utiliser des huiles naturelles d'origine végétale comportant des acides gras insaturés souvent instables à ces températures.  In general, the processes proposed are for the most part applicable to inorganic pigments and / or use synthetic lipid derivatives of animal or mineral origin and / or comprise one or more heating stages at high temperature (greater than 100 ° C) poorly adapted to more unstable organic pigments. In addition, such processes are difficult to apply when it is desired to use natural oils of plant origin comprising unsaturated fatty acids often unstable at these temperatures.
Ainsi, il reste de pouvoir disposer d'un procédé unique permettant d'améliorer la dispersion (caractère hydrophobe lipophyle recherchés) et la stabilité de pigments organiques et inorganiques sous leur forme sèche ou dans leur formulation de destination finale et mettant en œuvre des huiles végétales naturelles aptes à être utilisées en cosmétique mais également dans d'autres domaines (peinture ou encre par exemple).  Thus, it remains to be able to have a unique process for improving the dispersion (desired lipophilic hydrophobicity) and the stability of organic and inorganic pigments in their dry form or in their final destination formulation and using vegetable oils. natural to be used in cosmetics but also in other areas (paint or ink for example).
Ceci est justement l'objet de la présente invention. La présente invention a donc pour objet de pouvoir fournir un pigment organique ou inorganique dont la surface a été modifiée, sous une forme sèche ou dispersée dans un solvant, de capacité dispersive et de stabilité élevées, et de bonne qualité tactile, ceci par un procédé simple et aisé à mettre en œuvre et applicable à la fois aux pigments organiques ou inorganiques, en présence éventuelle d'excipients. This is precisely the object of the present invention. The object of the present invention is therefore to provide an organic or inorganic pigment whose surface has been modified, in a dry or dispersed form in a solvent, of high dispersancy and stability, and of good tactile quality, by a process simple and easy to implement and applicable to both organic and inorganic pigments, in the possible presence of excipients.
En outre, il a été constaté que les compositions selon la présente invention In addition, it has been found that the compositions according to the present invention
(comprenant en particulier des pigments organiques) présentent des propriétés de stabilité/dégorgement avantageuses et surprenantes au vu de l'état de la technique. Ces propriétés sembleraient être en lien avec la présence d'impuretés naturelles dans les huiles naturelles, même si ces impuretés sont présentes à des taux extrêmement faibles. (In particular comprising organic pigments) have advantageous and surprising stability / disgorging properties in view of the state of the art. These properties seem to be related to the presence of natural impurities in natural oils, even if these impurities are present at extremely low levels.
Les inventeurs ont pu ainsi mettre en évidence que le procédé selon l'invention tel que décrit ci-après et mettant en œuvre une huile végétale naturelle, notamment lorsque le mélange huile végétale naturelle/solvant est vaporisé à la surface des pigments à traiter pour leur conférer les caractères souhaités, permet d'obtenir ces pigments avec de telles propriétés comme en particulier une meilleure dispersion et stabilité en stockage sous forme sèche ou en formulation et une élimination du phénomène de dégorgement en phase aqueuse pour les pigments organiques. The inventors have thus been able to demonstrate that the process according to the invention as described below and using a natural vegetable oil, in particular when the natural vegetable oil / solvent mixture is vaporized on the surface of the pigments to be treated to give them the desired characters, makes it possible to obtain these pigments with such properties as in particular better dispersion and storage stability in dry form or in formulation and removal of the aqueous phase bleeding phenomenon for organic pigments.
Ainsi, l'invention concerne un procédé de modification de surface d'un pigment inorganique ou organique, ledit procédé comprenant les étapes suivantes : Thus, the invention relates to a method of modifying the surface of an inorganic or organic pigment, said method comprising the following steps:
A) la mise en contact dudit pigment avec une huile végétale naturelle ;  A) contacting said pigment with a natural vegetable oil;
B) le cas échéant, le mélange dudit pigment avec ladite huile végétale naturelle ; et  B) where appropriate, mixing said pigment with said natural vegetable oil; and
C) le séchage du mélange obtenu à l'étape A) ou B),  C) drying the mixture obtained in step A) or B),
caractérisé en ce qu'à l'étape C), le séchage est réalisé à une température inférieure ou égale à 100 °C et supérieure au point de solidification de ladite huile végétale naturelle. characterized in that in step C), the drying is carried out at a temperature less than or equal to 100 ° C and greater than the solidification point of said natural vegetable oil.
De préférence, à l'étape C), le séchage est réalisé à une température comprise entre 40°C et 80°C, de préférence supérieure ou égale à 12 heures pour 80°C, supérieure ou égale à 18 heures pour 60°C ou supérieure ou égale à 24 heures pour 40°C. Selon un mode de réalisation préféré, le procédé de modification de surface d'un pigment selon la présente invention est caractérisé en ce que le pigment est organique, et ledit procédé comprend les étapes suivantes : Preferably, in step C), the drying is carried out at a temperature of between 40 ° C. and 80 ° C., preferably greater than or equal to 12 hours at 80 ° C., greater than or equal to 18 hours at 60 ° C. or greater than or equal to 24 hours for 40 ° C. According to a preferred embodiment, the surface modification method of a pigment according to the present invention is characterized in that the pigment is organic, and said process comprises the following steps:
A) la mise en contact dudit pigment avec une huile végétale naturelle ;  A) contacting said pigment with a natural vegetable oil;
B) le cas échéant, le mélange dudit pigment avec ladite huile végétale naturelle ; et  B) where appropriate, mixing said pigment with said natural vegetable oil; and
C) le séchage du mélange obtenu à l'étape A) ou B),  C) drying the mixture obtained in step A) or B),
caractérisé en ce qu'à l'étape C), le séchage est réalisé à une température inférieure ou égale à 100 °C et supérieure au point de solidification de ladite huile végétale, de préférence le séchage est réalisé à une température comprise entre 40 °C et 80 °C comme indiqué ci-dessus.  characterized in that in step C), the drying is carried out at a temperature less than or equal to 100 ° C and greater than the solidification point of said vegetable oil, preferably the drying is carried out at a temperature between 40 ° C and 80 ° C as indicated above.
Selon l'un quelconque des modes de réalisations préférés ou particulier de l'invention, le procédé de modification de surface selon la présente invention est caractérisé en ce que préalablement à l'étape A, ladite huile végétale naturelle ou ledit pigment est mélangé à un solvant.  According to any of the preferred or particular embodiments of the invention, the surface modification method according to the present invention is characterized in that prior to step A, said natural vegetable oil or said pigment is mixed with a solvent.
Dans les procédés de modification de surface selon l'invention, ledit solvant est caractérisé en ce qu'il est choisi parmi les solvants « verts » (non toxiques) ou les solvants organiques. De préférence, ledit solvant est choisi parmi l'eau, un alcool, de préférence l'éthanol, le propanol, l'isopropanol, le butanol ou un mélange d'eau/alcool. De préférence encore, ce solvant aqueux peut contenir ainsi de l'eau, des alcools, un mélange d'eau et d'alcool. Les alcools peuvent être notamment choisis parmi les monoalcools inférieurs linéaires ou ramifiés ayant de 2 à 5 atomes de carbone comme l'éthanol, le propanol, l'isopropanol ou le butanol, mais également des polyols comme la glycérine, la diglycérine, le propylène glycol, le sorbitol, le penthénol, le penthylène glycol, les polyéthylène glycols. In the surface modification methods according to the invention, said solvent is characterized in that it is chosen from "green" (non-toxic) solvents or organic solvents. Preferably, said solvent is selected from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol. More preferably, this aqueous solvent may thus contain water, alcohols, a mixture of water and alcohol. The alcohols may be chosen in particular from lower linear or branched monoalcohols having from 2 to 5 carbon atoms, such as ethanol, propanol, isopropanol or butanol, but also polyols such as glycerol, diglycerol or propylene glycol. sorbitol, penthenol, penthylene glycol, polyethylene glycols.
Selon un mode de réalisation particulier, le procédé est dépourvu d'agent de modification de surface supplémentaire que l'huile végétale naturelle et optionnellement du solvant.  According to a particular embodiment, the process is devoid of additional surface modifying agent than natural vegetable oil and optionally solvent.
Lorsque le procédé de l'invention est destiné à modifier la surface desdits pigments pour une utilisation cosmétique de ces pigments ainsi modifiés, on préfère utiliser des solvants « verts » (non toxiques). When the process of the invention is intended to modify the surface of said pigments for a cosmetic use of these pigments thus modified, it is preferred to use "green" (non-toxic) solvents.
Parmi les solvants « verts » (non toxiques), on préfère en particulier mais sans s'y limiter les solvants cosmétiquement acceptable, de préférence encore choisi dans le groupe constitué par les solvants « verts » (non toxiques) suivants : Ethanol, Eau, mélange Ethanol/Eau dans des proportions allant de 100%/0% à 0%/100%. Les proportions du mélange en masse relatives Ethanol/eau peuvent par exemple être comprise entre l%/99% et 99%/l%, entre 2%/98% et 98%/2%, entre 3%/97% et 97%/3%, entre 4%/96% et 96%/4%, entre 5%/95% et 95%/5%, entre 10%/90% et 90%/10%, entre 20%/80% et 80%/20%, entre 30%/70% et 70%/30%, entre 40%/60% et 60%/40%, ou encore être approxmativement égales à 50%/50% (c'est-à-dire plus ou moins 5%). Avantageusement, et selon les propriétés recherchées (hydratation, volatilité des solvants, solubilisation etc), la proportion en masse de l'un ou l'autre de ces solvants (eau et éthanol) peut être majoritaire, c'est-à-dire supérieure à 50%/50%, supérieure ou égale à 60%/40%, 70%/30%, 80%/10%, 90%/10%, 95%/5%, 96%/4%, 97%/3%, 98%/2%, ou encore 99%/l%.  Among the "green" (non-toxic) solvents, in particular, but not limited to, cosmetically acceptable solvents, preferably chosen from the group consisting of the following "green" (non-toxic) solvents: Ethanol, Water, Ethanol / Water mixture in proportions ranging from 100% / 0% to 0% / 100%. The proportions of the relative mass mixture Ethanol / water may for example be between 1% / 99% and 99% / 1%, between 2% / 98% and 98% / 2%, between 3% / 97% and 97% / 3%, between 4% / 96% and 96% / 4%, between 5% / 95% and 95% / 5%, between 10% / 90% and 90% / 10%, between 20% / 80% and 80% / 20%, between 30% / 70% and 70% / 30%, between 40% / 60% and 60% / 40%, or be approximately equal to 50% / 50% (ie say more or less 5%). Advantageously, and according to the desired properties (hydration, volatility of solvents, solubilization, etc.), the mass proportion of one or the other of these solvents (water and ethanol) may be predominant, that is to say greater at 50% / 50%, greater than or equal to 60% / 40%, 70% / 30%, 80% / 10%, 90% / 10%, 95% / 5%, 96% / 4%, 97% / 3%, 98% / 2%, or 99% / 1%.
Selon un mode de réalisation préféré, le procédé de modification de surface d'un pigment selon la présente invention est caractérisé en ce que l'étape A est une mise en contact par vaporisation. En effet, de manière surprenante, il a été constaté que la vaporisation permet un enrobage très efficace des pigments, alors que l'on aurait pu s'attendre que les pigments, en particulier sous forme de poudre, soient enrobés de cette façon de manière inhomogène. Les techniques de vaporisations sont celles typiquement connues, c'est-à-dire par l'incoporation d'un liquide dans un véhicule gazeux (si l'un, plusieurs ou l'intégralité des consitutants du liquide ont des faibles températures d'ébullition, le gaz véhicule peut alors être formé par l'un ou plusieurs de ses constituants sous forme vapeur). En outre, le mélange liquide-gaz peut se faire par génération d'un pulvérisateur par dispositif tournant, par pulvérisations électrostatiques, par pulvérisations ultrasoniques, etc. Les techniques de mises en œuvre de toutes ces buses sont bien connues de l'homme du métier. Par exemple, la présence de gaz n'est pas obligatoire dans certains cas spécifiques. Toutefois, de manière plus commune l'invention se fait à pression atmosphérique, voire pression réduite. Dans le contexte de la présente invention, les huiles végétales naturelles ayant des hauts points d'ébullition, la vaporisation consistera souvent en la suspension de très fines gouttellettes de ces huiles, et/ou de leurs mélanges (éventuellement avec un ou plusieurs solvants) dans un gaz véhicule « porteur », selon la technique utilisée. L'homme du métier comprendra donc que dans le contexte de la présente invention vaporisation et pulvérisation sont synonymes pour des huiles végétales ayant de hauts points d'ébullition. Le gaz porteur peut être de toute nature chimique convenable à cette mise en œuvre et sera préférentiellement inerte, tel que l'argon, l'azote, l'hélium, etc. Typiquement dans le contexte de la présente invention, la vaporisation par pulvérisation (très fines gouttelettes) par l'intermédiaire d'une ou de plusieurs buses de pulvérisation sera préférée. Néanmoins d'autres techniques de vaporisation existent et sont applicables à la présente invention tel que le dépôt chimique en phase vapeur (« CVD » ou « chemical vapour déposition » en anglais), le dépôt physique en phase vapeur (« PVD » ou « physical vapour déposition » en anglais), l'épitaxie par jet moléculaire, le dépôt plasma, le dépôt laser puisé, le dépôt par la méthode sol-gel, le dépôt électrochimique, l'utilisation d'un nébulisateur à ultrasons ou le dépôt électrostatique. Toutes ces techniques et leur mise en œuvre sont bien connues dans l'art. According to a preferred embodiment, the method for modifying the surface of a pigment according to the present invention is characterized in that step A is a contacting by vaporization. Indeed, surprisingly, it has been found that the vaporization allows a very effective coating of the pigments, whereas it would have been expected that the pigments, in particular in the form of powder, are coated in this way inhomogeneous. The spraying techniques are those typically known, that is to say by the incoporation of a liquid in a gaseous vehicle (if one, several or all of the constituents of the liquid have low boiling temperatures, the carrier gas can then be formed by one or more of its constituents in vapor form). In addition, the liquid-gas mixture can be made by generating a rotating device sprayer, electrostatic spraying, ultrasonic spraying, etc. The techniques for implementing all these nozzles are well known to those skilled in the art. For example, the presence of gas is not mandatory in certain specific cases. However, more commonly the invention is at atmospheric pressure or reduced pressure. In the context of the present invention, natural vegetable oils having high boiling points, the vaporization will often consist of the suspension of very fine droplets of these oils, and / or their mixtures (optionally with one or more solvents) in a "carrier" carrier gas, according to the technique used. Those skilled in the art will therefore understand that in the context of the present invention vaporization and spraying are synonymous for vegetable oils having high boiling points. The carrier gas may be of any chemical nature suitable for this implementation and will preferably be inert, such as argon, nitrogen, helium, etc. Typically in the context of the present invention, spray spraying (very fine droplets) through one or more spray nozzles will be preferred. Nevertheless other vaporization techniques exist and are applicable to the present invention such as chemical vapor deposition ("CVD" or "chemical vapor deposition" in English), physical vapor deposition ("PVD" or "physical vapor deposition"). vapor deposition "), molecular beam epitaxy, plasma deposition, pulsed laser deposition, sol-gel deposition, electrochemical deposition, the use of an ultrasonic nebulizer or electrostatic deposition. All of these techniques and their implementation are well known in the art.
Afin d'aider à un enrobage homogène des particules de pigment, ces pigments seront mélangés, par exemple à l'aide d'un mélangeur interne équipé de thermorégulateur. Lors de la pulvérisation, la mise en contact de l'ensemble de la surface des pigments avec l'émulsion se fait ainsi de manière plus homogène. Le mélange émulsion -pigment se présente sous forme d'une poudre.  In order to aid in a homogeneous coating of the pigment particles, these pigments will be mixed, for example by means of an internal mixer equipped with a thermoregulator. During spraying, bringing the entire surface of the pigments into contact with the emulsion is thus more homogeneous. The emulsion-pigment mixture is in the form of a powder.
Cette étape de vaporisation permet un gain de coût très important en comparaison avec les techniques usuelles de trempage et mélangeage sous forme de suspension solide-liquide, car il n'est pas nécessaire d'utiliser autant de mélange huileux d'enrobage. Ceci permet ainsi d'économiser de manière importante l'apport d'énergie pour l'étape de séchage C. Néanmoins, la simple diminution des quantités de mélange d'enrobage ne semble pas expliquer intégralement la facilité accrue du séchage. Un effet technique inattendu semble également participer à ce résultat Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ou ledit pigment à l'étape A) est sous forme de poudre. This vaporization step allows a very significant cost saving in comparison with the usual techniques of soaking and mixing in the form of solid-liquid suspension, because it is not necessary to use as much oily mixture of coating. This thus saves significantly energy input for the drying step C. Nevertheless, the simple decrease in the amounts of coating mixture does not seem to fully explain the increased ease of drying. An unexpected technical effect also seems to contribute to this result According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said pigment in step A) is in powder form.
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ladite huile végétale naturelle est préalablement solubilisée ou émulsionnée dans un solvant. En revanche, l'huile végétale naturelle n'est pas soumise à des conditions de traitement qui modifieraient structurellement (c'est-à- dire la structure chimique de ses constituants) les composés qu'elle contient, telle qu'une hydrogénation, ou encore un raffinage.  According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said natural vegetable oil is previously solubilized or emulsified in a solvent. On the other hand, the natural vegetable oil is not subjected to treatment conditions which would modify structurally (ie the chemical structure of its constituents) the compounds it contains, such as a hydrogenation, or still a refining.
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ladite huile végétale naturelle est préalablement solubilisée ou émulsionnée dans un solvant dans un rapport masse à masse compris entre 1 % à 100 %, de préférence compris entre 20 % et 80 %, entre 40 % et 60 %, le plus préféré étant voisin de 50 % (plus ou moins 5 %). According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said natural vegetable oil is previously solubilized or emulsified in a solvent in a weight to mass ratio of between 1% and 100%, preferably between 20% and 80%, between 40% and 60%, the most preferred being close to 50% (plus or minus 5%).
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que le rapport massique entre ladite huile végétale naturelle et ledit pigment est inférieur à 50 %, de préférence compris entre 1 % et 30 %, entre 1 % et 10 %, le plus préféré étant voisin de 3 % (plus ou moins 1 %). (« Voie Sèche »).  According to a preferred embodiment, the surface modification method according to the present invention is characterized in that the mass ratio between said natural vegetable oil and said pigment is less than 50%, preferably between 1% and 30%, between 1% and 10%, the most preferred being close to 3% (plus or minus 1%). ("Dry Way").
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ladite huile végétale naturelle est solubilisée ou émulsionnée préalablement à l'étape A) dans un solvant choisi parmi l'eau, un alcool, de préférence l'éthanol, le propanol, l'isopropanol, le butanol ou un mélange d'eau/alcool. De préférence encore, ce solvant aqueux peut contenir ainsi de l'eau, des alcools, un mélange d'eau et d'alcool. Les alcools peuvent être notamment choisis parmi les monoalcools inférieurs linéaires ou ramifiés ayant de 2 à 5 atomes de carbone comme l'éthanol, le propanol, l'isopropanol ou le butanol, mais également des polyols comme la glycérine, la diglycérine, le propylène glycol, le sorbitol, le penthénol, le penthylène glycol, les polyéthylène glycols.  According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent selected from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol. More preferably, this aqueous solvent may thus contain water, alcohols, a mixture of water and alcohol. The alcohols may be chosen in particular from lower linear or branched monoalcohols having from 2 to 5 carbon atoms, such as ethanol, propanol, isopropanol or butanol, but also polyols such as glycerol, diglycerol or propylene glycol. sorbitol, penthenol, penthylene glycol, polyethylene glycols.
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ladite huile végétale naturelle préalablement émulsionnée ou solubilisée dans un solvant est, à l'étape A), greffée sur le pigment dont on souhaite modifier la surface.  According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said natural vegetable oil previously emulsified or solubilized in a solvent is, in step A), grafted onto the pigment whose surface is to be modified. .
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que le rapport massique entre ledit pigment et ladite huile végétale naturelle est inférieur à 50 %, de préférence compris entre 5 % et 30 % , entre 5 et 10%, le plus préféré étant voisin de 5 % (plus ou moins 1 %). (« Voie liquide »). According to a preferred embodiment, the surface modification method according to the present invention is characterized in that the mass ratio between said pigment and said oil natural plant is less than 50%, preferably between 5% and 30%, between 5 and 10%, the most preferred being close to 5% (plus or minus 1%). ("Liquid Way").
Le procédé de modification de surface selon la présente invention est caractérisé en ce que : The surface modification method according to the present invention is characterized in that:
- ladite huile végétale naturelle est solubilisée ou émulsionnée préalablement à l'étape A) dans un solvant qui peut également être choisi parmi les solvants de type hydrocarbure, de préférence pentane, hexane, cyclohexane, heptane, lorsque ledit pigment est d'origine organique ; et  said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent which may also be chosen from hydrocarbon-type solvents, preferably pentane, hexane, cyclohexane, heptane, when said pigment is of organic origin; and
- ladite huile végétale naturelle est solubilisée ou émulsionnée préalablement à l'étape A) dans un solvant choisi parmi l'eau, un alcool, de préférence l'éthanol, le propanol, l'isopropanol, le butanol ou un mélange d'eau/alcool lorsque ledit pigment est d'origine inorganique. Ce solvant aqueux peut contenir ainsi de l'eau, des alcools, un mélange d'eau et d'alcool. Les alcools peuvent être notamment choisis parmi les monoalcools inférieurs linéaires ou ramifiés ayant de 2 à 5 atomes de carbone comme l'éthanol, le propanol, l'isopropanol ou le butanol, mais également des polyols comme la glycérine, la diglycérine, le propylène glycol, le sorbitol, le penthénol, le penthylène glycol, les polyéthylène glycols. Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que préalablement à l'étape C), le mélange obtenu à l'étape B) est filtré puis, le cas échéant, lavé et/ou rincé dans le but d'éliminer les composés du mélange n'ayant pas réagi avec ledit pigment. Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que les étapes de lavage (et/ou rinçage) et de récupération du pigment dont la surface a été modifiée sont effectuées en présence de solvant par séparation mécanique (décantation, centrifugation), filtration en profondeur ou sur support, de préférence par filtration sur support membranaire, par extraction sous vide.  said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent chosen from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol when said pigment is of inorganic origin. This aqueous solvent can thus contain water, alcohols, a mixture of water and alcohol. The alcohols may be chosen in particular from lower linear or branched monoalcohols having from 2 to 5 carbon atoms, such as ethanol, propanol, isopropanol or butanol, but also polyols such as glycerol, diglycerol or propylene glycol. sorbitol, penthenol, penthylene glycol, polyethylene glycols. According to a preferred embodiment, the surface modification method according to the present invention is characterized in that prior to step C), the mixture obtained in step B) is filtered and then, if necessary, washed and / or rinsed off. in order to remove the compounds of the mixture unreacted with said pigment. According to a preferred embodiment, the surface modification method according to the present invention is characterized in that the steps of washing (and / or rinsing) and recovery of the pigment whose surface has been modified are carried out in the presence of solvent by mechanical separation. (decantation, centrifugation), filtration in depth or on a support, preferably by filtration on a membrane support, by vacuum extraction.
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ladite huile végétale naturelle contient des esters de triglycéride d'acide gras saturés et/ou insaturés, de préférence de longueur C12 à C24. Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ladite huile végétale naturelle est choisie de préférence parmi le groupe d'huiles constitué de préférence par l'huile de macadamia, de figue de barbarie, de bourrache, de périlla, d'olive, de jojoba, d'amande douce, d'avocat, de buruti, de grenade, d'onagre, de tournesol, de thé vert et d'argan, etc. According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said natural vegetable oil contains saturated and / or unsaturated fatty acid triglyceride esters, preferably of length C12 to C24. According to one preferred embodiment, the surface modification method according to the present invention is characterized in that said natural vegetable oil is preferably chosen from the group of oils consisting preferably of macadamia oil, prickly pear, borage, perilla, olive, jojoba, sweet almond, avocado, buruti, pomegranate, evening primrose, sunflower, green tea and argan, etc.
Préférentiellement, l'huile végétale est choisi dans le groupe d'huile constitué par l'huile de macadamia, de figue de barbarie, de bourrache, de périlla, de jojoba, d'amande douce, d'avocat, de buruti, de grenade, d'onagre, de tournesol, de thé vert et d'argan. Plus préférentiellement, l'huile végétale est choisi dans le groupe d'huile constitué par l'huile d'amande douce, d'avocat, de buruti, de grenade, d'onagre, de tournesol, de thé vert et d'argan. De manière également préférée, l'huile végétale peut être choisie dans le groupe d'huile constitué par l'huile de macadamia, de figue de barbarie, de bourrache, de périlla, de jojoba. Les huiles de jojoba, d'amande douce, d'avocat, de tournesol, et d'olive sont particulièrement intéressantes de part leur coûts faibles d'achat lié à leurs quantités de productions annuelle dans l'industrie.  Preferably, the vegetable oil is selected from the group of oils consisting of macadamia oil, prickly pear, borage, perilla, jojoba, sweet almond, avocado, buruti, pomegranate , evening primrose, sunflower, green tea and argan. More preferably, the vegetable oil is selected from the oil group consisting of sweet almond oil, avocado, buruti, pomegranate, evening primrose, sunflower, green tea and argan. Also preferably, the vegetable oil may be selected from the group consisting of oil of macadamia oil, prickly pear, borage, perilla, jojoba. Jojoba, sweet almond, avocado, sunflower and olive oils are particularly attractive because of their low purchase costs related to their annual production quantities in the industry.
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ledit pigment est un pigment organique ou une composition comprenant un pigment organique, de préférence choisi parmi les pigments vrais, les encres ou les laques, de préférence les laques. FD&C Yellow 5; FD&C Yellow 6; D&C Yellow 10, FD&C Red 4; FD&C Green 3; D&C Red 7; D&C Red 6; D&C Red 30, D&C Red 33, D&C Red 34; D&C Red 36; D&C Red 27; D&C Red 28; D&C Red 22; D&C Red 21; FD&C Red 40 et FD&C Blue 1. According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said pigment is an organic pigment or a composition comprising an organic pigment, preferably chosen from true pigments, inks or lacquers, preferably the lacquers. FD & C Yellow 5; FD & C Yellow 6; D & C Yellow 10, FD & C Red 4; FD & C Green 3; D & C Red 7; D & C Red 6; D & C Red 30, D & C Red 33, D & C Red 34; D & C Red 36; D & C Red 27; D & C Red 28; D & C Red 22; D & C Red 21 ; FD & C Red 40 and FD & C Blue 1.
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ledit pigment est un pigment organique, ou une composition comprenant un pigment organique, choisi parmi (voir à l'Exemple 1A suivant les Tableaux 1 à 4 pour la structure et des exemples de composition de ces pigments organiques). According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said pigment is an organic pigment, or a composition comprising an organic pigment, chosen from (see Example 1A according to Tables 1 to 4 for the structure and examples of composition of these organic pigments).
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ledit pigment est un pigment inorganique, de préférence pouvant être composé des différents éléments chimiques suivants : F, Na, Mg, Al, Si, P, S, K, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, ou W.  According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said pigment is an inorganic pigment, preferably consisting of the following different chemical elements: F, Na, Mg, Al, Si, P, S, K, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, or W.
Selon un mode préféré, le procédé de modification de surface selon la présente invention est caractérisé en ce que ledit pigment est un pigment composite formé d'un ou plusieurs pigments inorganiques associés à un ou plusieurs excipients en présence ou non d'une laque, de préférence un pigment inorganique choisi dans le groupe constitué des pigments suivants, le Black Iran Oxide, Red Iran Oxide, Yellow Iran Oxide, Manganèse Violet, Ultramarine Blue, Titanium Dioxide, Chromium Oxide Green, Zinc Oxide, Iran Blue, Chromium Oxide Hydrated. According to a preferred embodiment, the surface modification method according to the present invention is characterized in that said pigment is a composite pigment formed of one or more inorganic pigments associated with one or more excipients in the presence or absence of a lacquer, preferably an inorganic pigment selected from the group consisting of the following pigments, Black Iran Oxide, Red Iran Oxide, Yellow Iran Oxide, Violet Manganese, Ultramarine Blue, Titanium Dioxide, Chromium Oxide Green, Zinc Oxide, Blue Iran, Chromium Oxide Hydrated.
Dans le procédé de modification de surface selon la présente invention, ledit excipient est choisi de préférence parmi les excipients d'origine naturelle ou synthétique, de préférence encore choisi dans le groupe suivant : In the surface modification method according to the present invention, said excipient is preferably chosen from excipients of natural or synthetic origin, more preferably chosen from the following group:
- Mica de formule X2Y4-6Z802(OH,F)4 avec X =K, Na, Ca, Ba, Rb, Cs ; Y=A1, Mg, Mn, Cr, Ti, Li etc. et Z = Si, Al, Fe3+, Ti ; Mica of formula X 2 Y 4 -6 Z 8 O 2 (OH, F) 4 with X = K, Na, Ca, Ba, Rb, Cs; Y = A1, Mg, Mn, Cr, Ti, Li etc. and Z = Si, Al, Fe 3+ , Ti;
- Fluorphlogopite synthétique de formule KMg3(AlSl30io)F2 ;  Synthetic fluororphlogopite of formula KMg3 (AlS130IO) F2;
- Talc de formule Mg3Si4Oio(OH)2 ; Talc of formula Mg 3 Si 4 O 10 (OH) 2 ;
- Séricite de formule KA12 [(OH,F)2|AlSi3Oi0]/ KA12 [(OH,F)2|AlSi3Oi0] ; - Sericite of formula KA1 2 [(OH, F) 2 | AlSi 3 O 1 O ] / KA 1 2 [(OH, F) 2 | AlSi 3 O 0 ];
- Silice de formule Si02 ; - Silica of formula Si0 2 ;
- Alumine de formule A1203 et Alumina of formula A1 2 0 3 and
- Sulfate de Barium de formule BaS04. - Barium sulphate of formula BaS0 4 .
Sous un autre aspect, ledit pigment est un pigment composite formé d'un ou plusieurs pigments inorganiques associés à un ou plusieurs excipients en présence ou non d'une laque. De préférence ledit pigment est un pigment composite comprenant un ou plusieurs pigments inorganiques, un excipient et le cas échéant une laque choisi dans le groupe constitué des pigments composites suivants : In another aspect, said pigment is a composite pigment formed of one or more inorganic pigments associated with one or more excipients in the presence or absence of a lacquer. Preferably, said pigment is a composite pigment comprising one or more inorganic pigments, an excipient and, if appropriate, a lacquer chosen from the group consisting of the following composite pigments:
- Mica (59 à 69%), Ti02 (18 à 28%), Fe304 (1 à 6%), FeO(OH) (1 à 2%) et Red7Calcium (8 à 12%) ; Mica (59 to 69%), TiO 2 (18 to 28%), Fe 3 O 4 (1 to 6%), FeO (OH) (1 to 2%) and Red7Calcium (8 to 12%);
- Mica (56 à 66%), Ti02 (10 à 20%), Fe304 (2 à 12%), FeO(OH) (1 à 1 1%) etMica (56 to 66%), TiO 2 (10 to 20%), Fe 3 O 4 (2 to 12%), FeO (OH) (1 to 1%) and
Red7Calcium (8 à 12%) ; Red7Calcium (8 to 12%);
- Fluorphlogopite synthétique (18 à 28%), Ti02 (54 à 64%) et Red40Aluminium (13 à 23%) ; - Synthetic fluororphlogopite (18 to 28%), Ti0 2 (54 to 64%) and Red40Aluminium (13 to 23%);
- Fluorphlogopite synthétique (23 à 33%>), Ti02 (57 à 67%>) et Red7Calcium (5 à 15%) ; Synthetic fluororphlogopite (23 to 33%), Ti0 2 (57 to 67%) and Red7Calcium (5 to 15%);
- Mica (48 à 58%), Ti02 (32 à 42%) et Red7Calcium (8 à 12%) ; Mica (48 to 58%), TiO 2 (32 to 42%) and Red7Calcium (8 to 12%);
- Mica (46 à 56%), Ti02 (34 à 44%) et Red7Calcium (8 à 12%) ; Mica (46 to 56%), TiO 2 (34 to 44%) and Red7Calcium (8 to 12%);
- Mica (50 à 60%), Ti02 (29 à 39%) et Red7Calcium (10 à 14%) ; Mica (50 to 60%), TiO 2 (29 to 39%) and Red7Calcium (10 to 14%);
- Mica (49 à 59%), Ti02 (36 à 46%) et Red7Calcium (3 à 7%) ; Mica (49-59%), TiO 2 (36-46%) and Red7Calcium (3-7%);
- Mica (46 à 56%), Ti02 (34 à 44%) et Red28 Aluminium (5 à 15%) ; Mica (46 to 56%), TiO 2 (34 to 44%) and Red28 Aluminum (5 to 15%);
- Mica (44 à 54%), Ti02 (32 à 42%) et Blue 1 Aluminium (9 à 19%) ; Mica (44 to 54%), TiO 2 (32 to 42%) and Blue Aluminum (9 to 19%);
- Mica (48 à 58%), Ti02 (28 à 38%) et Yellow5 Aluminium (9 à 19%) ; Mica (48 à 58%), Ti02 (28 à 38%) et Red6Sodium (9 à 19%) ; Mica (48 to 58%), TiO 2 (28 to 38%) and Yellow Aluminum (9 to 19%); Mica (48-58%), Ti0 2 (28 to 38%) and Red6Sodium (9-19%);
Mica (47 à 57%), Ti02 (31 à 41%) et Red30 Aluminium (7 à 17%). Mica (47 to 57%), Ti0 2 (31 to 41%) and Red30 Aluminum (7 to 17%).
Mica (43 à 54 %) et Ti02 (46 à 57 %) Mica (43 to 54%) and Ti0 2 (46 to 57%)
Mica (55 à 65 %) et Ti02 (45 à 55 %) Mica (55 to 65%) and Ti0 2 (45 to 55%)
Mica (62 à 73 %) et Ti02 (27 à 38 %) Mica (62 to 73%) and Ti0 2 (27 to 38%)
Mica (77 à 87 %) et Ti02 (13 à 23 %) Mica (77 to 87%) and Ti0 2 (13 to 23%)
Mica (64 à 74 %) et Ti02 (26 à 36 %) Mica (64 to 74%) and Ti0 2 (26 to 36%)
Mica (52 à 63 %) et Ti02 (37 à 48 %) Mica (52 to 63%) and Ti0 2 (37 to 48%)
Mica (47 à 58 %) et Ti02 (42 à 53 %) Mica (47 to 58%) and Ti0 2 (42 to 53%)
Mica (45 à 56 %) et Ti02 (44 à 55 %) Mica (45 to 56%) and Ti0 2 (44 to 55%)
Mica (43 à 54 %) et Ti02 (46 à 57 %) Mica (43 to 54%) and Ti0 2 (46 to 57%)
Mica (37 à 48 %) et Ti02 (52 à 63 %) ; Mica (37 to 48%) and Ti0 2 (52 to 63%);
Mica (54 à 64 %) et Fe203 (36 à 46 %) ; Mica (54 to 64%) and Fe 2 O 3 (36 to 46%);
Mica (52 à 62 % et Fe203 (38 à 48 %) ; Mica (52 to 62% and Fe 2 O 3 (38 to 48%);
Mica (62 à 72 %) et Fe203 (28 à 38 %) ; et Mica (62 to 72%) and Fe 2 O 3 (28 to 38%); and
Mica (55 à 70 %), Ti02 (28 à 38 %) et Fe203 (2 à 7 %). Mica (55 to 70%), TiO 2 (28 to 38%) and Fe 2 O 3 (2 to 7%).
Sous un autre aspect, la présente invention a pour objet un procédé de préparation d'une poudre de pigments ou d'une composition comprenant au moins un pigment, de préférence destinée à être utilisée en cosmétique, en peinture ou dans les encres, de préférence en cosmétique, caractérisé en ce qu'il comprend les étapes suivantes : In another aspect, the present invention relates to a process for preparing a pigment powder or a composition comprising at least one pigment, preferably intended for use in cosmetics, in paint or in inks, preferably in cosmetics, characterized in that it comprises the following steps:
1) la modification de la surface du pigment par un procédé de modification de surface selon la présente invention; et  1) modifying the surface of the pigment by a surface modification method according to the present invention; and
2) une étape récupération dudit pigment ou de ladite composition comprenant au moins un pigment dont la surface a ainsi été modifiée obtenue à l'étape C) sous forme d'une poudre.  2) a recovery step of said pigment or of said composition comprising at least one pigment whose surface has thus been modified obtained in step C) in the form of a powder.
Sous un autre aspect, la présente invention a pour objet un pigment, revêtu d'acide gras, ou poudre de pigment susceptible d'être directement obtenu par un procédé de modification de surface selon la présente invention. In another aspect, the present invention provides a pigment, fatty acid coated, or pigment powder that can be directly obtained by a surface modification method according to the present invention.
De préférence, le pigment selon la présente invention est caractérisé en ce qu'il est revêtu d'acide gras dont la concentration est comprise entre 1 et 25 % en poids, de préférence encore entre 1 % et 10 %, entre 1 % et 7,5 % ou 1 % et 5 %. Sous un autre aspect, la présente invention a pour objet une composition comprenant un pigment ou une poudre de pigment selon la présente invention, dans un mélange avec un ingrédient pharmaceutiquement ou cosmétiquement acceptable. Sous un autre aspect, la présente invention a pour objet une composition comprenant un pigment selon la présente invention ou poudre obtenue par le procédé selon la présente invention, destinée à être utilisée en cosmétique, dans les encres ou en peinture, de préférence en cosmétique. De préférence, la composition cosmétique selon la présente invention est caractérisée en ce qu'elle est contenue dans un far à paupières, un far à joues, un rouge à lèvres, une crème, un gel, un bâton de rouge à lèvres ou une laque à lèvres, un brillant à lèvres, un fond de teint solide, un contours des yeux, un mascara, un eye liner, une poudre compactée, un blush ou encore un vernis à ongle, un pain de savon ou toute forme de produit cosmétique. Ces compositions peuvent, en outre, contenir d'autres composés actifs en cosmétique ou en dermo-cosmétique, notamment pour y apporter un aspect soin ou traitant à la composition. Preferably, the pigment according to the present invention is characterized in that it is coated with fatty acid whose concentration is between 1 and 25% by weight, more preferably between 1% and 10%, between 1% and 7%. , 5% or 1% and 5%. In another aspect, the present invention provides a composition comprising a pigment or a pigment powder according to the present invention, in a mixture with a pharmaceutically or cosmetically acceptable ingredient. In another aspect, the present invention relates to a composition comprising a pigment according to the present invention or powder obtained by the process according to the present invention, intended for use in cosmetics, inks or in paint, preferably in cosmetics. Preferably, the cosmetic composition according to the present invention is characterized in that it is contained in an eyeshadow, a cheek powder, a lipstick, a cream, a gel, a lipstick stick or a lacquer a lip gloss, a solid foundation, an eye contour, a mascara, an eyeliner, a compacted powder, a blush or a nail polish, a bar of soap or any form of cosmetic product. These compositions may, in addition, contain other active compounds in cosmetics or dermo-cosmetics, in particular to provide a care or treatment aspect to the composition.
Un autre aspect de l'invention concerne une composition selon l'invention caractérisée en ce que la valeur de dE (colorimétrie) reste inférieure ou égale à 2 sur un laps de temps d'au moins 36 mois, préférentiellement 24 mois, plus préférentiellement 18 mois, encore plus préférentiellement 12 mois ou 6 mois. Another aspect of the invention relates to a composition according to the invention characterized in that the value of dE (colorimetry) remains less than or equal to 2 over a lapse of time of at least 36 months, preferably 24 months, more preferably 18 months, even more preferably 12 months or 6 months.
Les valeurs colorimétriques de référence permettant de calculer le dE sont celles du pigment traité au temps tO, c'est-à-dire le pigment obtenu juste après la mise en œuvre du procédé selon l'invention.  The reference colorimetric values making it possible to calculate the dE are those of the pigment treated at time t0, that is to say the pigment obtained just after the implementation of the process according to the invention.
De manière avantageuse, la température de stockage de la composition selon l'invention est inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C, préférentiellement pendant un laps de temps de 36 mois.  Advantageously, the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C., 5 ° C. C or 0 ° C, preferably for a period of time of 36 months.
De manière plus avantageuse, la température de stockage de la composition selon l'invention est inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, More advantageously, the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C.
5°C ou 0°C, préférentiellement pendant un laps de temps de 24 mois. 5 ° C or 0 ° C, preferably for a period of time of 24 months.
De manière encore plus avantageuse, la température de stockage de la composition selon l'invention est inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C, préférentiellement pendant un laps de temps de 18 mois. De manière encore plus avantageuse, la température de stockage de la composition selon l'invention est inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C, préférentiellement pendant un laps de temps de 12 mois. Even more advantageously, the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C. 5 ° C or 0 ° C, preferably for a period of 18 months. Even more advantageously, the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C. 5 ° C or 0 ° C, preferably for a period of 12 months.
De manière encore plus avantageuse, la température de stockage de la composition selon l'invention est inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C, préférentiellement pendant un laps de temps de 6 mois.  Even more advantageously, the storage temperature of the composition according to the invention is less than or equal to 60 ° C., 50 ° C., 40 ° C., 30 ° C., 25 ° C., 20 ° C., 10 ° C. 5 ° C or 0 ° C, preferably for a period of time of 6 months.
De manière préférée, la composition selon l'invention ayant une valeur de dE restant inférieure ou égale à 2 sur un laps de temps déterminé, comme expliqué ci- dessus, comprends au moins un pigment consistant en un ou plusieurs pigments selon la présente invention.  Preferably, the composition according to the invention having a value of dE remaining less than or equal to 2 over a determined period of time, as explained above, comprises at least one pigment consisting of one or more pigments according to the present invention.
Ainsi, un aspect de l'invention concerne l'utilisation d'un pigment selon l'invention afin de stabiliser le dE d'une composition à une valeur inférieure ou égale à 2 sur un laps de temps d'au moins 36 mois préférentiellement 24 mois, plus préférentiellement 18 mois, encore plus préférentiellement 12 mois ou 6 mois. Thus, one aspect of the invention relates to the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 36 months, preferably 24. month, more preferably 18 months, even more preferably 12 months or 6 months.
De manière avantageuse, l'utilisation d'un pigment selon l'invention afin de stabiliser le dE d'une composition à une valeur inférieure ou égale à 2 sur un laps de temps d'au moins 36 mois se fait à une température de stockage de ladite composition à stabiliser inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C.  Advantageously, the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 36 months is at a storage temperature. of said composition to be stabilized less than or equal to 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
De manière plus avantageuse, l'utilisation d'un pigment selon l'invention afin de stabiliser le dE d'une composition à une valeur inférieure ou égale à 2 sur un laps de temps d'au moins 24 mois se fait à une température de stockage de ladite composition à stabiliser inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C.  More advantageously, the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 24 months is at a temperature of storing said composition to be stabilized at or below 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
De manière encore plus avantageuse, l'utilisation d'un pigment selon l'invention afin de stabiliser le dE d'une composition à une valeur inférieure ou égale à 2 sur un laps de temps d'au moins 18 mois se fait à une température de stockage de ladite composition à stabiliser inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C.  Even more advantageously, the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 18 months is at a temperature of storing said composition to be stabilized less than or equal to 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
De manière encore plus avantageuse, l'utilisation d'un pigment selon l'invention afin de stabiliser le dE d'une composition à une valeur inférieure ou égale à 2 sur un laps de temps d'au moins 12 mois se fait à une température de stockage de ladite composition à stabiliser inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C.  Even more advantageously, the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 12 months is at a temperature of storing said composition to be stabilized less than or equal to 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
De manière encore plus avantageuse, l'utilisation d'un pigment selon l'invention afin de stabiliser le dE d'une composition à une valeur inférieure ou égale à 2 sur un laps de temps d'au moins 6 mois se fait à une température de stockage de ladite composition à stabiliser inférieure ou égale à 60°C, 50°C, 40°C, 30°C, 25°C, 20°C, 10°C, 5°C ou 0°C. Even more advantageously, the use of a pigment according to the invention in order to stabilize the dE of a composition at a value of less than or equal to 2 over a period of time of at least 6 months is at a temperature of storage of said composition to stabilize at or below 60 ° C, 50 ° C, 40 ° C, 30 ° C, 25 ° C, 20 ° C, 10 ° C, 5 ° C or 0 ° C.
D'autres caractéristiques, aspects et avantages de la présente invention apparaîtront à la lecture de la description détaillée qui va suivre ainsi que des figures. Other features, aspects and advantages of the present invention will become apparent on reading the detailed description which will follow as well as the figures.
Légende des Figures Legend of Figures
Figure 1 : Exemple de triglycéride (représentation de la structure)  Figure 1: Example of triglyceride (representation of the structure)
Figure 2 : Structure de l'acide stéarique Figure 2: Structure of stearic acid
Figure 3 : Structure de l'acide palmitoléique Figure 3: Structure of palmitoleic acid
Figure 4 : Structure de l'acide linoléique Figure 4: Structure of linoleic acid
Exemple 1 : Définitions et Exemples de pigments utilisés Example 1: Definitions and Examples of Pigments Used
Pigments Organiques, Pigments Inorganiques et Excipients. Organic Pigments, Inorganic Pigments and Excipients.
Les pigments organiques sont majoritairement des laques.  The organic pigments are mainly lacquers.
- Les pigments vrais sont des molécules organiques qui précipitent en formant une structure organique insoluble.  True pigments are organic molecules that precipitate by forming an insoluble organic structure.
- Les encres sont obtenues par précipitation d'un colorant soluble dans l'eau en tant que sel de métal.  Inks are obtained by precipitation of a water-soluble dye as a metal salt.
- Les laques sont obtenues par adsorption d'un colorant soluble dans l'eau sur un substrat inorganique insoluble.  The lacquers are obtained by adsorption of a water-soluble dye on an insoluble inorganic substrate.
A) Exemples de Pigments organiques Voir Tableaux 1 à 4 A) Examples of Organic Pigments See Tables 1 to 4
TABLEAU 1 TABLE 1
Molécule /o Substrat % Substrat Molecule / o Substrate% Substrate
Référence Nom Reference Name
organique Pigment inorganique Inorganique Organic Inorganic Inorganic Pigment
C69-002 15 AI(OH)3 82,5 C69-002 15 AI (OH) 3 82.5
FD&C Yellow (1— '  FD & C Yellow (1- '
C69-4424 24 AI(OH)3 73,5 C69-4424 24 AI (OH) 3 73.5
5 Al. Lk  5 Al. Lk
C69-4537 nw, 38 AI(OH)3 59,5 C69-4537 nw, 38 Al (OH) 3 59.5
FD&C Yellow FD & C Yellow
C70-5270 40 AI(OH)3 57,5 C70-5270 40 AI (OH) 3 57.5
6 Al. Lk  6 Al Lk
TABLEAU 2 TABLE 2
Figure imgf000015_0001
Figure imgf000015_0001
coocw,  coocw,
TABLEAU 3  TABLE 3
Figure imgf000015_0002
Figure imgf000015_0002
*NC : Non communiqué TABLEAU 4 * NC: Not communicated TABLE 4
Molécule Substrat % Substrat Molecule Substrate% Substrate
Référence Nom % Pigment Reference Name% Pigment
organique inorganique Inorganique Inorganic inorganic organic
FD&C Blue 1 FD & C Blue 1
C39-4434 12 Al(OH)3 85 ,5 C39-443412Al (OH) 3 85.5
Al. Lk  Al. Lk
Exemples de Pigments inorganiques Examples of inorganic pigments
Les pigments inorganiques sont majoritairement des oxydes métalliques ou des complexes métalliques, dont un ou plusieurs éléments chimiques suivants (F, Na, Mg, Al, Si, P, S, K, Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, W)) peuvent entrer dans leur composition. La taille des particules varie entre 10 nm et 10 μιη. The inorganic pigments are predominantly metal oxides or metal complexes, including one or more of the following chemical elements (F, Na, Mg, Al, Si, P, S, K, Ca, Ti, V, Cr, Mn, Fe, Co , Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, W)) can be used in their composition. The particle size varies between 10 nm and 10 μιη.
Voir Tableau 5 See Table 5
TABLEAU 5 TABLE 5
L'oxyde de fer noir : Fe304 ou Fe203/FeO : Aussi appelé oxyde ferrosoferrique obtenu par réduction de l'oxyde ferrique (rouge). Il est stable à la lumière, à la chaleur, aux solvants et aux acides. Black iron oxide: Fe 3 0 4 or Fe 2 O 3 / FeO: Also called ferrosoferric oxide obtained by reduction of ferric oxide (red). It is stable to light, heat, solvents and acids.
L'oxyde de fer rouge : Fe203 : Aussi appelé oxyde ferrique, c'est un pigment stable à la lumière, à la chaleur, aux solvants et aux acides. Red iron oxide: Fe 2 0 3 : Also called ferric oxide, it is a pigment that is stable to light, heat, solvents and acids.
L'oxyde de fer jaune : Fe203, H20 : Aussi appelé oxyde ferrique hydraté, c'est un pigment stable à la lumière, à la chaleur, aux solvants et aux acides. Yellow iron oxide: Fe 2 0 3 , H 2 0: Also called hydrated ferric oxide, it is a pigment that is stable to light, heat, solvents and acids.
Le dioxyde de titane : Ti02 : Pigment présentant un grand intérêt en cosmétique car il est utilisé en tant que filtre UV. Il présente une bonne résistance à la lumière, à la chaleur, aux solvants et aux acides. Titanium dioxide: Ti0 2 : Pigment with a great interest in cosmetics because it is used as a UV filter. It has good resistance to light, heat, solvents and acids.
L'« iron blue » : FeNH4Fe(CN)6 : Pigment minéral de couleur bleu prusse, remarquablement stable à la lumière, aux solvant et aux acides ; cependant, il ne résiste pas à une température supérieure à 200°C. Iron blue: FeNH 4 Fe (CN) 6 : Prussian blue mineral pigment, remarkably stable in light, solvents and acids; however, it does not withstand temperatures above 200 ° C.
Le bleu ultramarine : Na6AI6Si6024S4 : Pigment minéral artificiel obtenu par chauffage de soude, argile et souffre. Il est non toxique et est résistant à la lumière, à la chaleur et aux solvants ; cependant, il est peu résistant aux acides. Ultramarine blue: Na 6 Al 6 Si 6 0 24 S 4 : Artificial mineral pigment obtained by heating soda, clay and sulfur. It is nontoxic and is resistant to light, heat and solvents; however, it is not very resistant to acids.
L'oxyde de manganèse violet : Mn(NH4)P207 : Pigment minéral de couleur violette présentant une bonne stabilité à la lumière, à la chaleur, aux solvants et aux acides. Purple manganese oxide: Mn (NH 4 ) P 2 O 7 : Mineral pigment of violet color with good stability to light, heat, solvents and acids.
L'oxyde de chrome vert : Cr203 : Pigment vert olive remarquablement stable à la lumière, à la chaleur, aux agents chimiques et aux acides. Green Chromium Oxide: Cr 2 0 3 : Olive green pigment remarkably stable to light, heat, chemicals and acids.
L'oxyde de chrome vert hydraté : Cr203, (H20)2 : Pigment vert turquoise ayant une faible stabilité à la température mais avec une bonne stabilité à la lumière, aux acides et aux solvants. Green chromium oxide hydrate: Cr 2 0 3 , (H 2 0) 2 : Turquoise green pigment having low temperature stability but with good stability to light, acids and solvents.
L'oxyde de zinc : ZnOZinc oxide: ZnO
Figure imgf000017_0001
C) Exemples de Pigments composites
Figure imgf000017_0001
C) Examples of composite pigments
Les pigments composites formés d'un ou plusieurs pigments inorganiques, un 5 excipient et le cas échéant une laque (voir Tableaux 6 et 7) Composite pigments formed from one or more inorganic pigments, an excipient and optionally a lacquer (see Tables 6 and 7)
TABLEAU 6  TABLE 6
Pigments inorganiques- Laque Excipient  Inorganic Pigments - Excipient Lacquer
Ti02(18à28%) Ti0 2 (18-28%)
Fe3°4(l à 6%) Red7Calcium (8 à 12%) Mica (59 à 69%) FeO(OH) (1 à 2%) Fe 3 ° 4 (1 to 6%) Red7Calcium (8 to 12%) Mica (59 to 69%) FeO (OH) (1 to 2%)
TiO2(10à20%)TiO 2 (10 to 20%)
6 à 66%) 6 to 66%)
Fe3°4 (2 à 12%) Red7Calcium (8 à 12%) Mica (5 Fe 3 ° 4 (2 to 12%) Red7Calcium (8 to 12%) Mica (5
FeO(OH)(l à 11%)  FeO (OH) (1 to 11%)
Synthetic FluorophlogopiteSynthetic Fluorophlogopite
Ti02 (54 à 64%) Red40 Aluminium (13 à 23%) Ti0 2 (54 to 64%) Red40 Aluminum (13 to 23%)
(18 à 28%)  (18 to 28%)
Synthetic FluorophlogopiteSynthetic Fluorophlogopite
Ti02 (57 à 67%) Red7Calcium (5 à 15%) Ti0 2 (57 to 67%) Red7Calcium (5 to 15%)
(23 à 33%)  (23 to 33%)
Ti02(32 à 42%) Red7Calcium (8 à 12%) Mica (48 à 58%) Ti0 2 (32 to 42%) Red7Calcium (8 to 12%) Mica (48 to 58%)
Ti02(34à44%) Red7Calcium (8 à 12%) Mica (46 à 56%) Ti0 2 (34 to 44%) Red7Calcium (8 to 12%) Mica (46 to 56%)
Ti02(29à39%) Red7Calcium(10àl4%) Mica (50 à 60%) Ti0 2 (29 to 39%) Red7Calcium (10 to 14%) Mica (50 to 60%)
Ti02(36à46%) Red7Calcium (3 à 7%) Mica (49 à 59%) Ti0 2 (36 to 46%) Red7Calcium (3 to 7%) Mica (49 to 59%)
Ti02(34à44%) Red28Aluminium (5 à 15%) Mica (46 à 56%) Ti0 2 (34 to 44%) Red28Aluminium (5 to 15%) Mica (46 to 56%)
Ti02 (32 à 42%) BluelAluminium (9 à 19%) Mica (44 à 54%) Ti0 2 (32 to 42%) BluelAluminium (9 to 19%) Mica (44 to 54%)
Ti02(28 à 38%) Yellow5 Aluminium (9 à 19%>) Mica (48 à 58%) Ti0 2 (28 to 38%) Yellow5 Aluminum (9 to 19%>) Mica (48 to 58%)
Ti02(28 à 38%) Red6Sodium (9 à 19%) Mica (48 à 58%) Ti0 2 (28 to 38%) Red6Sodium (9 to 19%) Mica (48 to 58%)
Ti02(31 à 41%) Red30Aluminium (7 à 17%) Mica (47 à 57%) TABLEAU 7 Ti0 2 (31 to 41%) Red30Aluminium (7 to 17%) Mica (47 to 57%) TABLE 7
Figure imgf000019_0001
Figure imgf000019_0001
Les excipients, ils peuvent être d'origine naturelle ou synthétique et rentrent particulièrement dans la composition des pigments composites et des laques. Excipients, they can be of natural or synthetic origin and fit particularly into the composition of composite pigments and lacquers.
- Mica de formule X2Y4-6Z802.(OH,F)4 avec X =K, Na, Ca, Ba, Rb, Cs ; Y=A1, Mg, Mn, Cr, Ti, Li etc. et Z = Si, Al, Fe3+, Ti ; Mica of formula X 2 Y 4 -6 Z 8 O 2 (OH, F) 4 with X = K, Na, Ca, Ba, Rb, Cs; Y = A1, Mg, Mn, Cr, Ti, Li etc. and Z = Si, Al, Fe 3+ , Ti;
- Fluorphlogopite synthétique de formule KMg3(AlSl30io)F2 ; Synthetic fluororphlogopite of formula KMg 3 (AlSi 30 °) F2;
- Talc de formule Mg3Si4Oio(OH)2 ; Talc of formula Mg 3 Si 4 O 10 (OH) 2 ;
- Séricite de formule KA12 [(OH,F)2|AlSi3Oio]/ KA12 [(OH,F)2|AlSi3Oi0] ; - Sericite of formula KA1 2 [(OH, F) 2 | AlSi 3 O 10 ] / KA 1 2 [(OH, F) 2 | AlSi 3 O 0 ];
- Silice de formule Si02 ; - Silica of formula Si0 2 ;
- Alumine de formule A1203 et Alumina of formula A1 2 0 3 and
- Sulfate de Barium de formule BaS04. - Barium sulphate of formula BaS0 4 .
Exemple 2 : Huiles végétales naturelles testées Example 2 Natural Vegetable Oils Tested
Les huiles végétales naturelles se comportent comme des réactifs de couplage de part la présence de leurs acides gras issus de l'hydrolyse des ces huiles. L'agent de couplage dans ce procédé mettant en œuvre une huile végétale naturelle est un acide gras qui présente une fonction acide carboxylique à une de ses extrémités. Il est formé d'une chaîne qui peut comporter entre 6 et 50 carbones. Natural vegetable oils behave as coupling reagents because of the presence of their fatty acids resulting from the hydrolysis of these oils. The coupling agent in this process using a natural vegetable oil is an acid which has a carboxylic acid function at one of its ends. It consists of a chain that can have between 6 and 50 carbons.
Exemple d'huiles végétales naturelles testées avec les différents pigments ou compositions de pigments décrits dans l'Exemple 1 :  Example of natural vegetable oils tested with the various pigments or pigment compositions described in Example 1:
Huile de Macadamia, Huile de Figue de Barbarie, Huile de Bourrache, Huile de Macadamia oil, Prickly pear oil, Borage oil, Oils oil
Perilla, Huile d'Olive, Huile de Jojoba, Huile d'Argan, Huile d'Abricot, Huile d'Avocat Désodorisé, Huile de Rose Musquée. Perilla, Olive Oil, Jojoba Oil, Argan Oil, Apricot Oil, Deodorized Avocado Oil, Rosehip Oil.
Majoritairement, ces huiles végétales naturelles sont composées à 99% de matières grasses que sont les triglycérides. a) Exemple : triglycéride (Voir figure 1)  Mostly, these natural vegetable oils are composed of 99% fat, which is triglycerides. a) Example: Triglyceride (See Figure 1)
L'hydrolyse de ces triglycérides libère des acides gras et du glycérol. Les acides gras majoritaires dans la composition des huiles sont : Hydrolysis of these triglycerides releases fatty acids and glycerol. The major fatty acids in the composition of the oils are:
- Les acides gras saturés de formule chimique générale CH3-(CH2)n-COOH b) Exemple : Acide stéarique (Voir Figure 2) Saturated fatty acids of general chemical formula CH 3 - (CH 2 ) n -COOH b) Example: Stearic acid (See Figure 2)
- Les acides gras mono-insaturés de formule chimique générale CH3-(CH2)X- CH=CH-(CH2)y-COOH c) Exemple : Acide Palmitoléique (voir Figure 3) Monounsaturated fatty acids of general chemical formula CH 3 - (CH 2 ) X --CH = CH- (CH 2 ) y -COOH c) Example: Palmitoleic acid (see FIG. 3)
- Les acides gras poly-insaturés d) Exemple : Acide linoléique (voir Figure 4) Exemple 3 : Procédé dit par voie sèche Le principe de ce procédé est le greffage par mise en contact de l'agent de couplage et des pigments (substrats). Les pigments ainsi traités peuvent être organiques ou inorganiques. Ce procédé permet également de traiter les excipients et pigments à effets. Le procédé se déroule en trois étapes : Polyunsaturated fatty acids d) Example: Linoleic acid (see FIG. 4) Example 3: Dry method The principle of this process is grafting by bringing the coupling agent into contact with the pigments (substrates) . The pigments thus treated can be organic or inorganic. This process also makes it possible to treat the excipients and effect pigments. The process takes place in three stages:
Vaporisation du mélange contenant l'huile végétale et le solvant adéquat sur la surface du pigment (substrat) à traiter (ou de la composition comprenant le pigment à traiter).  Spraying the mixture containing the vegetable oil and the appropriate solvent on the surface of the pigment (substrate) to be treated (or the composition comprising the pigment to be treated).
- Mise en contact homogène du mélange Solvant/Huile végétale et du pigment à traiter (substrat),  - Homogeneous contact of the solvent / vegetable oil mixture and the pigment to be treated (substrate),
Séchage (Solvant/Huile Végétale + pigment).  Drying (solvent / vegetable oil + pigment).
• Etape 1 • Step 1
Une émulsion est préparée en mélangeant une ou plusieurs huiles végétales avec un solvant choisi. La préparation de ce mélange peut être faite en température. An emulsion is prepared by mixing one or more vegetable oils with a selected solvent. The preparation of this mixture can be made in temperature.
L' émulsion est ensuite entièrement vaporisée sur les pigments à traiter. The emulsion is then completely vaporized on the pigments to be treated.
Le pourcentage massique de l'huile végétale en solution varie en fonction du couple (Huile végétale/Pigment à traiter). Il est généralement considéré comme suffisant à partir de 1 %. Le choix du solvant (eau (H20), éthanol (EtOH) ou mélangeThe mass percentage of the vegetable oil in solution varies according to the couple (vegetable oil / pigment to be treated). It is generally considered sufficient from 1%. The choice of the solvent (water (H 2 0), ethanol (EtOH) or mixture
H20/EtOH) varie également en fonction du couple Huile végétale naturelle/Pigment.H 2 0 / EtOH) also varies according to the pair Natural vegetable oil / Pigment.
Les solvants organiques classiques peuvent également être employés mais les considérations environnementales actuelles et la volonté d'avoir un produit fini labellisable tendent à voir diminuer leurs usages. Conventional organic solvents can also be used, but current environmental considerations and the desire to have a labelable end product tend to diminish their use.
• Etape 2 : • 2nd step :
La mise en contact de l'ensemble de la surface des pigments avec l'émulsion se fait à l'aide d'un mélangeur interne équipé de thermorégulateur afin que cette mise en contact soit homogène. Le mélange émulsion + pigment se présente sous forme d'une poudre.  The entire surface of the pigments is brought into contact with the emulsion by means of an internal mixer equipped with a thermoregulator so that this bringing into contact is homogeneous. The emulsion + pigment mixture is in the form of a powder.
• Etape 3 : • Step 3:
Le mélange émulsion (Huile végétale naurelle/solvant) + pigment est chauffé à une température comprise entre 40 et 100°C.  The emulsion mixture (vegetable oil naurelle / solvent) + pigment is heated to a temperature between 40 and 100 ° C.
Exemple : Example:
- Les pigments organiques ou inorganiques (substrats) traités sont transvasés dans un pilulier en verre et séchés de préférence entre 1 et 24 heures. Exemple 4 : Procédé dit par voie liquide The organic or inorganic pigments (substrates) treated are transferred into a glass pill and preferably dried between 1 and 24 hours. Example 4: Process called by liquid route
L'huile végétale naturelle est greffée sur la surface du substrat (pigment) par immersion du substrat dans une solution ou émulsion contenant l'huile végétale naturelle. The natural vegetable oil is grafted onto the surface of the substrate (pigment) by immersing the substrate in a solution or emulsion containing the natural vegetable oil.
Le substrat fonctionnalisé est ensuite extrait de la solution de greffage puis sécher.  The functionalized substrate is then extracted from the grafting solution and then dried.
Les greffages se déroulent en trois étapes :  The grafting takes place in three stages:
1) Réaction de greffage par voie chimique entre l'huile végétale naturelle solubilisé ou émulsionnée dans un solvant adéquat et la surface du pigment à modifier, 1) chemical grafting reaction between the natural vegetable oil solubilized or emulsified in a suitable solvent and the surface of the pigment to be modified,
2) Elimination de la solution de greffage et lavage du pigment modifié, 3 Séchage du pigment fonctionnalisé. 2) Removal of the grafting solution and washing of the modified pigment, 3 Drying of the functionalized pigment.
• Etape 1 : • Step 1 :
L'étape de greffage s'effectue par réaction chimique entre l'huile végétale naturelle à concentration souhaitée et la surface d'un pigment à modifier, dans le solvant choisi (EtOH, H20 ou mélange H20/EtOH) pendant un temps désiré. The grafting step is carried out by chemical reaction between the natural vegetable oil at the desired concentration and the surface of a pigment to be modified, in the chosen solvent (EtOH, H 2 O or H 2 O / EtOH mixture) during a desired time.
Exemple de procédé mis en œuvre pour l'étape 1 : Example of a method implemented for step 1:
- Une solution/émulsion d'huile végétale naturelle est préparée par dissolution de l'huile végétale naturelle dans 10 ml de solvant.  - A solution / emulsion of natural vegetable oil is prepared by dissolving the natural vegetable oil in 10 ml of solvent.
Le pourcentage massique en huile végétale naturelle de la solution/émulsion varie entre 1% et 50% (huile végétale naturelle choisie/Substrat à traiter). Le choix du solvant (H20, EtOH ou mélange H20/EtOH) varie également en fonction du couple huile végétale naturelle /Substrat. Les solvants organiques classiques peuvent également être employés mais les considérations environnementales actuelles tendent à voir diminuer leurs usages. The mass percentage of natural vegetable oil of the solution / emulsion varies between 1% and 50% (natural vegetable oil chosen / substrate to be treated). The choice of the solvent (H 2 O, EtOH or H 2 O / EtOH mixture) also varies according to the natural vegetable oil / substrate pair. Conventional organic solvents can also be used, but current environmental considerations tend to diminish their use.
- 0,5 g de pigments est placé (substrat) dans un pilulier auquel est ajouté 10 ml de solution/émulsion d'huile végétale naturelle.  - 0.5 g of pigments is placed (substrate) in a pill box to which is added 10 ml of solution / emulsion of natural vegetable oil.
Condition Dynamique : La solution obtenue est placée sous agitation magnétique pendant un temps t de préférence à température ambiante (10-35 °C).  Dynamic condition: The resulting solution is placed under magnetic stirring for a time t preferably at room temperature (10-35 ° C).
Condition Statique : La réaction chimique se produit sans agitation magnétique de préférence à température ambiante (10-35 °C), pendant un temps t.  Static condition: The chemical reaction occurs without magnetic stirring preferably at room temperature (10-35 ° C) for a time t.
Le temps t varie entre 5 minutes et 72 h en fonction du couple huile végétale naturelle /Substrat. • Etape 2 : The time t varies between 5 minutes and 72 hours depending on the natural vegetable oil / substrate pair. • 2nd step :
La solution/émulsion de greffage non fixée sur les pigments est éliminée par fïltration puis le matériau (substrat modifié) est lavé afin de s'assurer de l'élimination complète de tous les éléments physisorbés.  The graft solution / emulsion not fixed on the pigments is removed by filtration and the material (modified substrate) is washed to ensure the complete elimination of all physisorbed elements.
Exemple de procédé mis en œuvre pour l'étape 2  Example of a process implemented for step 2
La solution contenue dans le pilulier est transvasée dans un tube pour centrifugeuse puis complété au ¾ par de l'EtOH.  The solution contained in the pill pillar is transferred to a centrifuge tube and then filled in with EtOH.
Après une centrifugation de 10 minutes à une vitesse de 20 000 trs.min" le filtrat est éliminé du tube pour centrifugeuse. After centrifugation for 10 minutes at a speed of 20 000 trs.min "the filtrate is removed from the centrifuge tube.
- Le tube pour centrifugeuse est complété à nouveau au ¾ par de l'EtOH et est placé dans un bac à Ultra-Sons pendant 10 minutes.  - The centrifuge tube is refilled at ¾ with EtOH and placed in an ultrasonic tank for 10 minutes.
La solution est ensuite centrifugée selon les mêmes conditions.  The solution is then centrifuged under the same conditions.
• Etape 3 : • Step 3:
Plusieurs étapes de séchage du matériau modifié sont ensuite effectuées.  Several drying steps of the modified material are then carried out.
Exemple de procédé mis en œuvre pour l'étape 3  Example of a process implemented for step 3
Après élimination du filtrat, le solvant résiduel est évaporé sous vide (5.10 1 mbar) durant 15 minutes. After removal of the filtrate, the residual solvent is evaporated under vacuum (5.10 1 mbar) for 15 minutes.
Les poudres de pigments (substrats) fonctionnalisés sont transvasées dans un pilulier en verre et séchés pendant 12 heures.  The functionalized pigment powders (substrates) are transferred to a glass pill and dried for 12 hours.
La température de l'étuve varie entre 20 et 100°C en fonction de la tolérance des différents substrats et agents de couplage aux conditions thermiques.  The temperature of the oven varies between 20 and 100 ° C depending on the tolerance of the different substrates and coupling agents to the thermal conditions.
Produits Finis : Pigments Inorganiques et Pigments Organiques traités présentant un caractère hydrophobe, des qualités tactiles ainsi qu'une bonne dispersibilité en phase huileuse. Pigments organiques traités présentant un dégordement très faible ou inexistant dans les phases aqueuse ou grasse. Finished Products: Inorganic pigments and treated organic pigments having a hydrophobic character, tactile qualities as well as good dispersibility in the oily phase. Organic treated pigments having a very low or non-existent deposition in the aqueous or fatty phases.
Avantages : Advantages :
Nouvelles propriétés (hydrophobie, meilleure dispersion, adhérence sur la peau, pouvoir couvrant).  New properties (hydrophobicity, better dispersion, adhesion to the skin, hiding power).
- Cette invention permet de lever des verrous technologiques rencontrés par les industriels de la Cosmétique en apportant un caractère hydrophobe aux pigments traités et une meilleur dispersibilité en formulation ainsi qu'un meilleur pouvoir couvrant dû à une meilleure adhérence sur la peau. - Les greffages mettent en jeu des énergies de liaison importantes et ce via une réaction irréversible. La formation de liaisons covalentes et iono-covalentes assure une grande stabilité dans le temps au greffage. This invention makes it possible to remove the technological locks encountered by the cosmetics industry by providing a hydrophobic character to the treated pigments and a better dispersibility in formulation as well as a better covering power due to better adhesion to the skin. - Grafting involve significant binding energies via an irreversible reaction. The formation of covalent and iono-covalent bonds ensures a high stability in time at grafting.
- L'invention permet de traiter par le même agent de couplage et par le même procédé une grande variété de substrats pigments inorganiques (métaux, oxydes métallique, etc.), pigments organiques, excipients et pigments composites.  The invention makes it possible to treat with the same coupling agent and by the same process a wide variety of inorganic pigment substrates (metals, metal oxides, etc.), organic pigments, excipients and composite pigments.
- Ce procédé selon la présente invention permet de traiter des pigments organiques, notamment à température peu élévée compatible avec ces pigments et les huiles végétales naturelles cosmétiquement et dermo-cosmétiquement acceptable que l'on souhaite mettre en œuvre.  This process according to the present invention makes it possible to treat organic pigments, in particular at a low temperature compatible with these pigments, and the cosmetically and dermo-cosmetically acceptable natural vegetable oils that it is desired to use.
- Ce procédé selon la présente invention permet de limiter les quantités de réactifs (agents de couplage) et de solvant utilisés.  This process according to the present invention makes it possible to limit the quantities of reagents (coupling agents) and of solvent used.
- Ce procédé selon la présente invention permet d'utiliser plusieurs procédés (voie « sèche », voie liquide, ultrasons).  This process according to the present invention makes it possible to use several processes ("dry" route, liquid route, ultrasound).
- Le procédé « voie sèche » selon l'invention mettant en œuvre l'étape de vaporisation et de mélange est particulièrement préféré, ce procédé permettant également de greffer à la surface des pigments les agents responsables entre autre de la propriété d'hydrophobie contenus dans les huiles végétales naturelles.  The "dry process" method according to the invention implementing the vaporization and mixing step is particularly preferred, this method also making it possible to graft onto the surface of the pigments the agents responsible, among other things, for the hydrophobicity property contained in natural vegetable oils.
- Les procédés selon la présente invention s'avèrent être, une fois mis au point, simples d'exécution et peu onéreux.  The processes according to the present invention prove to be, once developed, simple and inexpensive.
- Les procédés de greffage sont mis en oeuvre dans des conditions plus aisées que celle de l'art antérieur par exemple sous conditions ambiantes, non anhydres, ce qui permet d'éviter l'usage de solvants organiques.  The grafting processes are carried out under conditions that are easier than those of the prior art, for example under ambient, non-anhydrous conditions, which makes it possible to avoid the use of organic solvents.
- Ce procédé selon la présente invention utilise des solvants dits « safe » et des huiles végétales naturelles, ce qui permet d'envisager une labellisation ecocert pour les pigments traités ou encore les produits cosmétiques finis.  This process according to the present invention uses so-called "safe" solvents and natural vegetable oils, which makes it possible to envisage an ecocert labeling for the treated pigments or the finished cosmetic products.
- L'art antérieur fait état d'altération de la teinte des pigments lors de l'utilisation comme agent de couplage des dérivés d'acides gras, d'ester d'acides gras ou de trigycérides seuls ou en présence de phospholipides non-hydrogénés ou de sels métalliques, le procédé tel qu'établi, utilisant des huiles végétales naturelles avec une étape de séchage C dont la température est comprise entre 20 et 100°C limite les altérations de la teinte des pigments (voir tableau 22).  The prior art states that the hue of the pigments is impaired when the fatty acid derivatives, fatty acid ester or trigyceride coupling agents are used alone or in the presence of non-hydrogenated phospholipids. or metal salts, the method as established, using natural vegetable oils with a drying step C whose temperature is between 20 and 100 ° C limits the alterations in the hue of the pigments (see Table 22).
Exemple 5 : Exemple de réalisations : Example 5: Example of achievements:
- Pigments organiques (voir Tableaux 8 à 15): TABLEAU 8 - Organic pigments (see Tables 8 to 15): TABLE 8
Huile de Macadamia Macadamia oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
C69 002 10 95/5 12H 80°C C69 002 10 95/5 12H 80 ° C
C69 002 10 H20 12H 80°CC69 002 10H 2 O 12H 80 ° C
C69 4424 10 95/5 12H 80°CC69 4424 10 95/5 12H 80 ° C
C69 4424 10 H20 12H 80°CC69 4424 10H 2 O 12H 80 ° C
C69 4537 10 95/5 12H 80°CC69 4537 10 95/5 12H 80 ° C
C69 4537 10 H20 12H 80°CC 69 4537 10H 2 O 12H 80 ° C
C70 5270 10 95/5 12H 80°CC70 5270 10 95/5 12H 80 ° C
C70 5270 10 H20 12H 80°CC70 5270 10H 2 O 12H 80 ° C
C19 003 10 95/5 12H 80°CC19 003 10 95/5 12H 80 ° C
C19 003 10 H20 12H 80°CC19 003 10H 2 O 12H 80 ° C
C19 011 10 95/5 12H 80°CC19 011 10 95/5 12H 80 ° C
C19 011 10 H20 12H 80°CC19 011 10H 2 O 12H 80 ° C
C19 025 10 95/5 12H 80°CC19 025 10 95/5 12H 80 ° C
C19 025 10 H20 12H 80°CC19 025 10H 2 O 12H 80 ° C
C24 012 10 95/5 12H 80°CC24 012 10 95/5 12H 80 ° C
C24 012 10 H20 12H 80°CC24 012 10H 2 O 12H 80 ° C
C14 023 10 95/5 12H 80°CC 14 023 10 95/5 12H 80 ° C
C14 023 10 H20 12H 80°CC 14 023 10H 2 O 12H 80 ° C
C14 6602 10 95/5 12H 80°CC 14 6602 10 95/5 12H 80 ° C
C14 6602 10 H20 12H 80°CC 14 6602 10H 2 O 12H 80 ° C
C14 6623 10 95/5 12H 80°CC14 6623 10 95/5 12H 80 ° C
C14 6623 10 H20 12H 80°CC 14 6623 10H 2 O 12H 80 ° C
C14 6634 10 95/5 12H 80°CC14 6634 10 95/5 12H 80 ° C
C14 6634 10 H20 12H 80°CC 14 6634 10H 2 O 12H 80 ° C
C14 032 (pigment vrai) 10 95/5 12H 80°CC14 032 (true pigment) 10 95/5 12H 80 ° C
C14 032 (pigment vrai) 10 H20 12H 80°CC14 032 (true pigment) 10H 2 O 12H 80 ° C
C39 4433 10 95/5 12H 80°CC39 4433 10 95/5 12H 80 ° C
C39 4433 10 H20 12H 80°C FD&C Yellow 5 Al Lk. 10 95/5 12H 80°CC 39 4433 10H 2 O 12H 80 ° C FD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C
TABLEAU 9 TABLE 9
Huile de Jojoba Jojoba oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
C69 002 10 95/5 12H 80°C C69 002 10 95/5 12H 80 ° C
C69 002 10 H20 12H 80°CC69 002 10H 2 O 12H 80 ° C
C69 4424 10 95/5 12H 80°CC69 4424 10 95/5 12H 80 ° C
C69 4424 10 H20 12H 80°CC69 4424 10H 2 O 12H 80 ° C
C69 4537 10 95/5 12H 80°CC69 4537 10 95/5 12H 80 ° C
C69 4537 10 H20 12H 80°CC 69 4537 10H 2 O 12H 80 ° C
C70 5270 10 95/5 12H 80°CC70 5270 10 95/5 12H 80 ° C
C70 5270 10 H20 12H 80°CC70 5270 10H 2 O 12H 80 ° C
C19 003 10 95/5 12H 80°CC19 003 10 95/5 12H 80 ° C
C19 003 10 H20 12H 80°CC19 003 10H 2 O 12H 80 ° C
C19 011 10 95/5 12H 80°CC19 011 10 95/5 12H 80 ° C
C19 011 10 H20 12H 80°CC19 011 10H 2 O 12H 80 ° C
C19 025 10 95/5 12H 80°CC19 025 10 95/5 12H 80 ° C
C19 025 10 H20 12H 80°CC19 025 10H 2 O 12H 80 ° C
C24 012 10 95/5 12H 80°CC24 012 10 95/5 12H 80 ° C
C24 012 10 H20 12H 80°CC24 012 10H 2 O 12H 80 ° C
C14 023 10 95/5 12H 80°CC 14 023 10 95/5 12H 80 ° C
C14 023 10 H20 12H 80°CC 14 023 10H 2 O 12H 80 ° C
C14 6602 10 95/5 12H 80°CC 14 6602 10 95/5 12H 80 ° C
C14 6602 10 H20 12H 80°CC 14 6602 10H 2 O 12H 80 ° C
C14 6623 10 95/5 12H 80°CC14 6623 10 95/5 12H 80 ° C
C14 6623 10 H20 12H 80°CC 14 6623 10H 2 O 12H 80 ° C
C14 6634 10 95/5 12H 80°CC14 6634 10 95/5 12H 80 ° C
C14 6634 10 H20 12H 80°CC 14 6634 10H 2 O 12H 80 ° C
C14 032 (pigment vrai) 10 95/5 12H 80°CC14 032 (true pigment) 10 95/5 12H 80 ° C
C14 032 (pigment vrai) 10 H20 12H 80°CC14 032 (true pigment) 10H 2 O 12H 80 ° C
C39 4433 10 95/5 12H 80°C C39 4433 10 H20 12H 80°CC39 4433 10 95/5 12H 80 ° C C 39 4433 10H 2 O 12H 80 ° C
FD&C Yellow 5 Al Lk. 10 95/5 12H 80°CFD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 H20 12H 80°CD & C Red 7 Ca Lk. 10H 2 O 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C
TABLEAU 10 TABLE 10
Huile de Rose Musquée Rosehip oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
C69 002 10 95/5 12H 80°C C69 002 10 95/5 12H 80 ° C
C69 002 10 H20 12H 80°CC69 002 10H 2 O 12H 80 ° C
C69 4424 10 95/5 12H 80°CC69 4424 10 95/5 12H 80 ° C
C69 4424 10 H20 12H 80°CC69 4424 10H 2 O 12H 80 ° C
C69 4537 10 95/5 12H 80°CC69 4537 10 95/5 12H 80 ° C
C69 4537 10 H20 12H 80°CC 69 4537 10H 2 O 12H 80 ° C
C70 5270 10 95/5 12H 80°CC70 5270 10 95/5 12H 80 ° C
C70 5270 10 H20 12H 80°CC70 5270 10H 2 O 12H 80 ° C
C19 003 10 95/5 12H 80°CC19 003 10 95/5 12H 80 ° C
C19 003 10 H20 12H 80°CC19 003 10H 2 O 12H 80 ° C
C19 011 10 95/5 12H 80°CC19 011 10 95/5 12H 80 ° C
C19 011 10 H20 12H 80°CC19 011 10H 2 O 12H 80 ° C
C19 025 10 95/5 12H 80°CC19 025 10 95/5 12H 80 ° C
C19 025 10 H20 12H 80°CC19 025 10H 2 O 12H 80 ° C
C24 012 10 95/5 12H 80°CC24 012 10 95/5 12H 80 ° C
C24 012 10 H20 12H 80°CC24 012 10H 2 O 12H 80 ° C
C14 023 10 95/5 12H 80°CC 14 023 10 95/5 12H 80 ° C
C14 023 10 H20 12H 80°CC 14 023 10H 2 O 12H 80 ° C
C14 6602 10 95/5 12H 80°CC 14 6602 10 95/5 12H 80 ° C
C14 6602 10 H20 12H 80°CC 14 6602 10H 2 O 12H 80 ° C
C14 6623 10 95/5 12H 80°CC14 6623 10 95/5 12H 80 ° C
C14 6623 10 H20 12H 80°CC 14 6623 10H 2 O 12H 80 ° C
C14 6634 10 95/5 12H 80°CC14 6634 10 95/5 12H 80 ° C
C14 6634 10 H20 12H 80°CC 14 6634 10H 2 O 12H 80 ° C
C14 032 (pigment vrai) 10 95/5 12H 80°CC14 032 (true pigment) 10 95/5 12H 80 ° C
C14 032 (pigment vrai) 10 H20 12H 80°CC14 032 (true pigment) 10H 2 O 12H 80 ° C
C39 4433 10 95/5 12H 80°C C39 4433 10 H20 12H 80°CC39 4433 10 95/5 12H 80 ° C C 39 4433 10H 2 O 12H 80 ° C
FD&C Yellow 5 Al Lk. 10 95/5 12H 80°CFD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 H20 12H 80°CD & C Red 7 Ca Lk. 10H 2 O 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C
TABLEAU 11 TABLE 11
Huile de Jojoba Jojoba oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
FD&C Yellow 5 Al Lk. 10 95/5 12H 80°C FD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 H20 12H 80°CD & C Red 7 Ca Lk. 10H 2 O 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C TABLEAU 12 D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C TABLE 12
Huile de Rose Musquée Rosehip oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
FD&C Yellow 5 Al Lk. 10 95/5 12H 80°C FD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 H20 12H 80°CD & C Red 7 Ca Lk. 10H 2 O 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C TABLEAU 13 D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C TABLE 13
Huile de Figue de Barbarie Prickly pear oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
FD&C Yellow 5 Al Lk. 10 95/5 12H 80°C FD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 H20 12H 80°CD & C Red 7 Ca Lk. 10H 2 O 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C TABLEAU 14 D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C TABLE 14
Huile d'Argan Argan Oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
FD&C Yellow 5 Al Lk. 10 95/5 12H 80°C FD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 H20 12H 80°CD & C Red 7 Ca Lk. 10H 2 O 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C TABLEAU 15 D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C TABLE 15
Huile de Perilla Perilla oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
FD&C Yellow 5 Al Lk. 10 95/5 12H 80°C FD & C Yellow 5 Al Lk. 10 95/5 12H 80 ° C
FD&C Yellow 5 Al Lk 10 H20 12H 80°CFD & C Yellow 5 Al Lk 10H 2 O 12H 80 ° C
FD&C Yellow 6 Al Lk 10 95/5 12H 80°CFD & C Yellow 6 Al Lk 10 95/5 12H 80 ° C
FD&C Yellow 6 Al Lk 10 H20 12H 80°CFD & C Yellow 6 Al Lk 10H 2 O 12H 80 ° C
D&C Red 7 Ca Lk. 10 95/5 12H 80°CD & C Red 7 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 7 Ca Lk. 10 H20 12H 80°CD & C Red 7 Ca Lk. 10H 2 O 12H 80 ° C
D&C Red 6 Ba Lk 10 95/5 12H 80°CD & C Red 6 Ba Lk 10 95/5 12H 80 ° C
D&C Red 6 Ba Lk 10 H20 12H 80°CD & C Red 6 Ba Lk 10 H 2 0 12H 80 ° C
D&C Red 34 Ca Lk. 10 95/5 12H 80°CD & C Red 34 Ca Lk. 10 95/5 12H 80 ° C
D&C Red 34 Ca Lk 10 H20 12H 80°CD & C Red 34 Ca Lk 10 H 2 0 12H 80 ° C
D&C Red 27A1 Lk 10 95/5 12H 80°CD & C Red 27A1 Lk 10 95/5 12H 80 ° C
D&C Red 27A1 Lk 10 H20 12H 80°CD & C Red 27A1 Lk 10H 2 O 12H 80 ° C
D&C Red 28A1 Lk 10 95/5 12H 80°CD & C Red 28A1 Lk 10 95/5 12H 80 ° C
D&C Red 28A1 Lk 10 H20 12H 80°CD & C Red 28A1 Lk 10H 2 O 12H 80 ° C
D&C Red 22 Al Lk 10 95/5 12H 80°CD & C Red 22 Al Lk 10 95/5 12H 80 ° C
D&C Red 22 Al Lk 10 H20 12H 80°CD & C Red 22 Al Lk 10 H 2 0 12H 80 ° C
D&C Red 21 10 95/5 12H 80°CD & C Red 21 10 95/5 12H 80 ° C
D&C Red 21 10 H20 12H 80°CD & C Red 21 10H 2 O 12H 80 ° C
D&C Red 21 Al Lk 10 95/5 12H 80°CD & C Red 21 Al Lk 10 95/5 12h 80 ° C
D&C Red 21 Al Lk 10 H20 12H 80°C Pigments inorganiques (Voir Tableaux 16 à 21) TABLEAU 16 D & C Red 21 Al Lk 10 H 2 0 12H 80 ° C Inorganic pigments (See Tables 16 to 21) TABLE 16
Huile de Jojoba Jojoba oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
Noir (Fe304) 3 95/5 12H 80°CBlack (Fe 3 O 4 ) 3 95/5 12H 80 ° C
Noir (Fe304) 5 95/5 12H 80°CBlack (Fe 3 O 4 ) 5 95/5 12H 80 ° C
Rouge (Fe203) 3 95/5 12H 80°CRed (Fe 2 O 3 ) 3 95/5 12H 80 ° C
Rouge (Fe203) 5 95/5 12H 80°CRed (Fe 2 O 3 ) 5 95/5 12H 80 ° C
Jaune (Fe203, H20) 3 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 3 95/5 12H 80 ° C
Jaune (Fe203, H20) 5 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5 95/5 12H 80 ° C
Ti02 3 95/5 12H 80°CTiO 2 95/5 12H 80 ° C
Ti02 5 95/5 12H 80°CTi0 2 95/5 12H 80 ° C
Noir (Fe304) 3 H20 12H 80°CBlack (Fe 3 O 4 ) 3H 2 O 12H 80 ° C
Noir (Fe304) 5 H20 12H 80°CBlack (Fe 3 O 4 ) 5H 2 O 12H 80 ° C
Rouge (Fe203) 3 H20 12H 80°CRed (Fe 2 O 3 ) 3H 2 O 12H 80 ° C
Rouge (Fe203) 5 H20 12H 80°CRed (Fe 2 O 3 ) 5H 2 O 12H 80 ° C
Jaune (Fe203, H20) 3 H20 12H 80°CYellow (Fe 2 O 3 , H 2 O) 3 H 2 O 12H 80 ° C
Jaune (Fe203, H20) 5 H20 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5H 2 O 12H 80 ° C
Ti02 3 H20 12H 80°CTi0 2 3H 2 O 12H 80 ° C
Ti02 5 H20 12H 80°C TABLEAU 17 Ti0 2 5 H 2 0 12H 80 ° C TABLE 17
Huile de Macadamia Macadamia oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
Noir (Fe304) 3 95/5 12H 80°CBlack (Fe 3 O 4 ) 3 95/5 12H 80 ° C
Noir (Fe304) 5 95/5 12H 80°CBlack (Fe 3 O 4 ) 5 95/5 12H 80 ° C
Rouge (Fe203) 3 95/5 12H 80°CRed (Fe 2 O 3 ) 3 95/5 12H 80 ° C
Rouge (Fe203) 5 95/5 12H 80°CRed (Fe 2 O 3 ) 5 95/5 12H 80 ° C
Jaune (Fe203, H20) 3 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 3 95/5 12H 80 ° C
Jaune (Fe203, H20) 5 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5 95/5 12H 80 ° C
Ti02 3 95/5 12H 80°CTiO 2 95/5 12H 80 ° C
Ti02 5 95/5 12H 80°CTi0 2 95/5 12H 80 ° C
Noir (Fe304) 3 H20 12H 80°CBlack (Fe 3 O 4 ) 3H 2 O 12H 80 ° C
Noir (Fe304) 5 H20 12H 80°CBlack (Fe 3 O 4 ) 5H 2 O 12H 80 ° C
Rouge (Fe203) 3 H20 12H 80°CRed (Fe 2 O 3 ) 3H 2 O 12H 80 ° C
Rouge (Fe203) 5 H20 12H 80°CRed (Fe 2 O 3 ) 5H 2 O 12H 80 ° C
Jaune (Fe203, H20) 5 H20 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5H 2 O 12H 80 ° C
Ti02 3 H20 12H 80°CTi0 2 3H 2 O 12H 80 ° C
Ti02 5 H20 12H 80°C Ti0 2 5 H 2 0 12H 80 ° C
TABLEAU 18 TABLE 18
Huile Figue de Barbarie Barbary fig oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
Noir (Fe304) 3 95/5 12H 80°CBlack (Fe 3 O 4 ) 3 95/5 12H 80 ° C
Noir (Fe304) 5 95/5 12H 80°CBlack (Fe 3 O 4 ) 5 95/5 12H 80 ° C
Rouge (Fe203) 3 95/5 12H 80°CRed (Fe 2 O 3 ) 3 95/5 12H 80 ° C
Rouge (Fe203) 5 95/5 12H 80°CRed (Fe 2 O 3 ) 5 95/5 12H 80 ° C
Jaune (Fe203, H20) 3 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 3 95/5 12H 80 ° C
Jaune (Fe203, H20) 5 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5 95/5 12H 80 ° C
Ti02 3 95/5 12H 80°CTiO 2 95/5 12H 80 ° C
Ti02 5 95/5 12H 80°CTi0 2 95/5 12H 80 ° C
Noir (Fe304) 3 H20 12H 80°CBlack (Fe 3 O 4 ) 3H 2 O 12H 80 ° C
Noir (Fe304) 5 H20 12H 80°CBlack (Fe 3 O 4 ) 5H 2 O 12H 80 ° C
Rouge (Fe203) 3 H20 12H 80°CRed (Fe 2 O 3 ) 3H 2 O 12H 80 ° C
Rouge (Fe203) 5 H20 12H 80°CRed (Fe 2 O 3 ) 5H 2 O 12H 80 ° C
Jaune (Fe203, H20) 3 H20 12H 80°CYellow (Fe 2 O 3 , H 2 O) 3 H 2 O 12H 80 ° C
Jaune (Fe203, H20) 5 H20 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5H 2 O 12H 80 ° C
Ti02 3 H20 12H 80°CTi0 2 3H 2 O 12H 80 ° C
Ti02 5 H20 12H 80°C Ti0 2 5 H 2 0 12H 80 ° C
TABLEAU 19 TABLE 19
Huile d'Argan Argan Oil
% massique % mass
Pigment solvant (%EtOH/H20) séchage huile Solvent Pigment (% EtOH / H 2 O) drying oil
Noir (Fe304) 3 95/5 12H 80°CBlack (Fe 3 O 4 ) 3 95/5 12H 80 ° C
Noir (Fe304) 5 95/5 12H 80°CBlack (Fe 3 O 4 ) 5 95/5 12H 80 ° C
Rouge (Fe203) 3 95/5 12H 80°CRed (Fe 2 O 3 ) 3 95/5 12H 80 ° C
Rouge (Fe203) 5 95/5 12H 80°CRed (Fe 2 O 3 ) 5 95/5 12H 80 ° C
Jaune (Fe203, H20) 3 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 3 95/5 12H 80 ° C
Jaune (Fe203, H20) 5 95/5 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5 95/5 12H 80 ° C
Ti02 3 95/5 12H 80°CTiO 2 95/5 12H 80 ° C
Ti02 5 95/5 12H 80°CTi0 2 95/5 12H 80 ° C
Oxyde de chrome Cr203 3 95/5 12H 80°CChromium oxide Cr 2 0 3 3 95/5 12H 80 ° C
ZnO 3 95/5 12H 80°CZnO 3 95/5 12H 80 ° C
ZnO nano 3 95/5 12H 80°C iron blue FeNH4Fe(CN)6 5 95/5 12H 80°CZnO nano 3 95/5 12H 80 ° C iron blue FeNH 4 Fe (CN) 6 5 95/5 12H 80 ° C
Noir (Fe304) 3 H20 12H 80°CBlack (Fe 3 O 4 ) 3H 2 O 12H 80 ° C
Noir (Fe304) 5 H20 12H 80°CBlack (Fe 3 O 4 ) 5H 2 O 12H 80 ° C
Rouge (Fe203) 3 H20 12H 80°CRed (Fe 2 O 3 ) 3H 2 O 12H 80 ° C
Rouge (Fe203) 5 H20 12H 80°CRed (Fe 2 O 3 ) 5H 2 O 12H 80 ° C
Jaune (Fe203, H20) 3 H20 12H 80°CYellow (Fe 2 O 3 , H 2 O) 3 H 2 O 12H 80 ° C
Jaune (Fe203, H20) 5 H20 12H 80°CYellow (Fe 2 O 3 , H 2 O) 5H 2 O 12H 80 ° C
Ti02 3 H20 12H 80°CTi0 2 3H 2 O 12H 80 ° C
Ti02 5 H20 12H 80°CTi0 2 5 H 2 0 12H 80 ° C
Oxyde de chrome Cr203 3 H20 12H 80°CChromium oxide Cr 2 0 3 3 H 2 0 12H 80 ° C
Oxyde de chrome Cr203 5 H20 12H 80°CChromium oxide Cr 2 0 3 5 H 2 0 12H 80 ° C
ZnO 3 H20 12H 80°CZnO 3 H 2 O 12H 80 ° C
ZnO 5 H20 12H 80°C iron blue ZnO 5 H 2 0 12H 80 ° C iron blue
5 H20 12H 80°C FeN¾Fe(CN)6 TABLEAU 20 5H 2 0 12H 80 ° C FeN¾Fe (CN) 6 TABLE 20
Figure imgf000040_0001
TABLEAU 21
Figure imgf000040_0001
TABLE 21
Figure imgf000041_0001
Exemple 6: Tests de colorimétrie
Figure imgf000041_0001
Example 6: Colorimetric Tests
Dans le tableau 22 ci-dessous, des tests de colorimétrie ont montrés que les pigments traités selon l'invention, 18 mois auparavant, ne varient quasiment pas dans le temps en termes de colorimétrie. Pour comparaison, les valeurs colorimétriques de pigments sans traitement selon l'invention sont données dans le tableau 22 ci-dessous. En particulier, sur un laps de temps de 18 mois à température ambiante, la valeur dE reste inférieure à la valeur seuil de 2 (donc indétectable à l'œil nu) sur la base du pigment non traité. Ainsi les résultats selon le tableau 22 d'une part confirment que les pigments obtenus selon l'invention présentent une teinte identique à l'œil nu aux pigments non traités (comme cela avait été d'ailleurs constaté juste après l'obtention de ces pigments par l'application du procédé selon l'invention), et d'autre part de manière totalement surprenante que la couleur de ces nouveaux pigments ne varie pas de manière visible dans le temps. Cet aspect est surprenant car on aurait pu penser que les huiles végétales enrobant les pigments auraient pu se dégrader (par exemple par oxydation) en produisant une teinte néfaste. Or, il n'en est rien. Cette valeur dE semble donc assez facilement extrapolable au moins à 36 mois en prenant comme élément de comparaison le pigment traité selon le procédé de l'invention au temps tO. Cette stabilité de teinte des pigments selon l'invention est surprenante et permet d'envisager leur utilisation pour la production et la commercialisation ultérieure de produits finis (compositions) particuliers dont les caractéristiques colorimétriques doivent rester stables (par exemple déterminées par des normes) tout en présentant les caractéristiques physico-chimiques avantageuses telles que décrites ci-dessus. In Table 22 below, colorimetric tests have shown that the pigments treated according to the invention, 18 months ago, do not vary almost in time in terms of colorimetry. For comparison, the colorimetric values of pigments without treatment according to the invention are given in Table 22 below. In particular, over a period of 18 months at room temperature, the dE value remains below the threshold value of 2 (thus undetectable to the naked eye) on the basis of the untreated pigment. Thus the results according to Table 22 confirm that the pigments obtained according to the invention have a hue identical to the naked eye to the untreated pigments (as had been found just after obtaining these pigments by the application of the method according to the invention), and secondly in a completely surprising way that the color of these new pigments does not vary visibly over time. This aspect is surprising because one would have thought that the vegetable oils coating the pigments could have degraded (for example by oxidation) producing a harmful hue. However, it is not. This dE value therefore seems quite easily extrapolable at least 36 months by taking as a comparative element the pigment treated according to the process of the invention at time t0. This coloration stability of the pigments according to the invention is surprising and makes it possible to envisage their use for the production and subsequent marketing of particular finished products (compositions) whose colorimetric characteristics must remain stable (for example determined by standards) while having the advantageous physicochemical characteristics as described above.
TABLEAU 22 TABLE 22
Figure imgf000043_0001
Figure imgf000043_0001

Claims

REVENDICATIONS
1. Procédé de modification de surface d'un pigment inorganique ou organique, ledit procédé comprenant les étapes suivantes : A method of surface modification of an inorganic or organic pigment, said method comprising the steps of:
A) la mise en contact dudit pigment avec une huile végétale naturelle préférentiellement par vaporisation ;  A) contacting said pigment with a natural vegetable oil preferably by vaporization;
B) le cas échéant, le mélange dudit pigment avec ladite huile végétale naturelle ; et  B) where appropriate, mixing said pigment with said natural vegetable oil; and
C) le séchage du mélange obtenu à l'étape A) ou B),  C) drying the mixture obtained in step A) or B),
caractérisé en ce que l'étape C), le séchage est réalisé à une température inférieure ou égale à 100 °C et supérieure au point de solidification de ladite huile végétale naturelle, de préférence le séchage est réalisé à une température comprise entre 40 °C et 80 °C.  characterized in that step C), the drying is carried out at a temperature less than or equal to 100 ° C and greater than the solidification point of said natural vegetable oil, preferably drying is carried out at a temperature between 40 ° C and 80 ° C.
2. Procédé de modification de surface selon la revendication 1, caractérisé en ce que préalablement à l'étape A, ladite huile végétale naturelle ou ledit pigment est mélangé à un solvant. 2. Surface modification method according to claim 1, characterized in that prior to step A, said natural vegetable oil or said pigment is mixed with a solvent.
3. Procédé de modification de surface selon la revendication 1 ou 2, caractérisé en ce que ou ledit pigment à l'étape A) est sous forme de poudre. 3. Surface modification method according to claim 1 or 2, characterized in that said pigment in step A) is in powder form.
4. Procédé de modification de surface selon l'une des revendications 1 à 3, caractérisé en ce que ladite huile végétale naturelle est préalablement solubilisée ou émulsionnée dans un solvant. 4. Surface modification method according to one of claims 1 to 3, characterized in that said natural vegetable oil is previously solubilized or emulsified in a solvent.
5. Procédé de modification de surface selon la revendication 4, caractérisé en ce que ladite huile végétale naturelle est préalablement solubilisée ou émulsionnée dans un solvant dans un rapport volume à volume compris entre 1 % à 100 %, de préférence compris entre 20 % et 80 % , entre 40 % et 60 %, le plus préféré étant voisin de 50 % (plus ou moins 5 %). 5. Surface modification method according to claim 4, characterized in that said natural vegetable oil is previously solubilized or emulsified in a solvent in a volume to volume ratio of between 1% and 100%, preferably between 20% and 80%. %, between 40% and 60%, the most preferred being close to 50% (plus or minus 5%).
6. Procédé de modification de surface selon l'une des revendication 1 à 5, caractérisé en ce que le rapport massique entre ladite huile végétale naturelle et ledit pigment est inférieur à 50 %, de préférence compris entre 1 % et 30 %, entre 1 % et 10 %, le plus préféré étant voisin de 3 % (plus ou moins 1 %). (« Voie Sèche »). 6. A method of surface modification according to one of claims 1 to 5, characterized in that the mass ratio between said natural vegetable oil and said pigment is less than 50%, preferably between 1% and 30%, between 1 % and 10%, the most preferred being close to 3% (plus or minus 1%). ("Dry Way").
7. Procédé de modification de surface selon la revendication 6, caractérisé en ce que ladite huile végétale naturelle est solubilisée ou émulsionnée préalablement à l'étape A) dans un solvant choisi parmi l'eau, un alcool, de préférence l'éthanol, le propanol, Pisopropanol, le butanol ou un mélange d'eau/alcool. Surface modification method according to claim 6, characterized in that said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent chosen from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol.
8. Procédé de modification de surface selon l'une des revendications 6 et 7, caractérisé en ce que ladite huile végétale naturelle préalablement émulsionnée ou solubilisée dans un solvant est, à l'étape A), est mise en contact avec le pigment dont on souhaite modifier la surface. 8. Surface modification method according to one of claims 6 and 7, characterized in that said natural vegetable oil previously emulsified or solubilized in a solvent is, in step A), is brought into contact with the pigment of which one wants to change the surface.
9. Procédé de modification de surface selon l'une des revendication 1 à 5, caractérisé en ce que le rapport massique entre ledit pigment et ladite huile végétale naturelle est inférieur à 50 %, de préférence compris entre 5 % et 30 %, entre 5 et 10 %, le plus préféré étant voisin de 5 % (plus ou moins 1 %). 9. Surface modification method according to one of claims 1 to 5, characterized in that the mass ratio between said pigment and said natural vegetable oil is less than 50%, preferably between 5% and 30%, between 5% and 30%. and 10%, the most preferred being close to 5% (plus or minus 1%).
10. Procédé de modification de surface selon la revendication 9, caractérisé en ce que : Surface modification method according to claim 9, characterized in that:
- ladite huile végétale naturelle est solubilisée ou émulsionnée préalablement à l'étape A), de préférence dans un solvant choisi parmi l'eau, un alcool, de préférence l'éthanol, le propanol, l'isopropanol, le butanol ou un mélange d'eau/alcool lorsque ledit pigment est d'origine inorganique ; et  said natural vegetable oil is solubilized or emulsified prior to step A), preferably in a solvent chosen from water, an alcohol, preferably ethanol, propanol, isopropanol, butanol or a mixture of water / alcohol when said pigment is of inorganic origin; and
- ladite huile végétale naturelle est solubilisée ou émulsionnée préalablement à l'étape A) dans un solvant choisi parmi les solvants de type hydrocarbure, de préférence pentane, hexane, cyclohexane, heptane, lorsque ledit pigment est d'origine organique.  said natural vegetable oil is solubilized or emulsified prior to step A) in a solvent chosen from hydrocarbon-type solvents, preferably pentane, hexane, cyclohexane, heptane, when said pigment is of organic origin.
11. Procédé de modification de surface selon l'une des revendications 9 et 10, caractérisé en ce que préalablement à l'étape C), le mélange obtenu à l'étape B) est filtré puis, le cas échéant, lavé et/ou rincé dans le but d'éliminer les composés du mélange n'ayant pas réagi avec ledit pigment. 11. Surface modification method according to one of claims 9 and 10, characterized in that prior to step C), the mixture obtained in step B) is filtered and, if necessary, washed and / or rinsed in order to remove the compounds of the unreacted mixture with said pigment.
12. Procédé de modification de surface selon la revendication 1 1 , caractérisé en ce que les étapes de lavage (et/ou rinçage) et de récupération du pigment dont la surface a été modifiée sont effectuées en présence de solvant par séparation mécanique (décantation, centrifugation), fïltration en profondeur ou sur support, de préférence par fïltration sur support membranaire, par extraction sous vide. Surface modification method according to claim 11, characterized in that the steps of washing (and / or rinsing) and recovering the pigment whose surface has been modified are carried out in the presence of solvent by mechanical separation (decantation, centrifugation), filtration in depth or on a support, preferably by filtration on a membrane support, by vacuum extraction.
13. Procédé de modification de surface selon l'une des revendications 1 à 12, caractérisé en ce que ladite huile végétale naturelle contient des esters de triglycéride d'acide gras saturés et/ou insaturés, de préférence de longueur C12 à C24. 13. Surface modification method according to one of claims 1 to 12, characterized in that said natural vegetable oil contains saturated and / or unsaturated fatty acid triglyceride esters, preferably of length C12 to C24.
14. Procédé de modification de surface selon la revendication 13, caractérisé en ce que ladite huile végétale naturelle est choisi parmi le groupe d'huiles constitué de préférence par l'huile d'olive, de jojoba, de macadamia, de figue de barbarie, de bourrache, de périlla, d'amande douce, d'avocat, de bourrache, de buruti, de grenade, d'onagre, de tournesol, de thé vert et d'argan. 14. Surface modification method according to claim 13, characterized in that said natural vegetable oil is chosen from the group of oils consisting preferably of olive oil, jojoba, macadamia, prickly pear, borage, perilla, sweet almond, avocado, borage, buruti, pomegranate, evening primrose, sunflower, green tea and argan.
15. Procédé de modification de surface selon l'une des revendications 1 à 14, caractérisé en ce que ledit pigment est un pigment organique ou une composition comprenant un pigment organique, de préfrence choisi parmi les les pigments vrais, les encres ou les laques, de préférence les laques. 15. Surface modification method according to one of claims 1 to 14, characterized in that said pigment is an organic pigment or a composition comprising an organic pigment, preferably selected from true pigments, inks or lacquers, preferably lacquers.
16. Procédé de modification de surface selon la revendication 15, caractérisé en ce que ledit pigment est un pigment organique, ou une composition comprenant un pigment organique, choisi parmi : FD&C Yellow 5; FD&C Yellow 6; D&C Yellow 10, FD&C Red 4; FD&C Green 3; D&C Red 7; D&C Red 6; D&C Red 30, D&C Red 33, D&C Red 34; D&C Red 36; D&C Red 27; D&C Red 28; D&C Red 22; D&C Red 21; FD&C Red 40 et FD&C Blue 1. 16. Surface modification method according to claim 15, characterized in that said pigment is an organic pigment, or a composition comprising an organic pigment, chosen from: FD & C Yellow 5; FD & C Yellow 6; D & C Yellow 10, FD & C Red 4; FD & C Green 3; D & C Red 7; D & C Red 6; D & C Red 30, D & C Red 33, D & C Red 34; D & C Red 36; D & C Red 27; D & C Red 28; D & C Red 22; D & C Red 21 ; FD & C Red 40 and FD & C Blue 1.
17. Procédé de modification de surface selon l'une des revendications 1 à 14, caractérisé en ce que ledit pigment est un pigment inorganique, de préférence pouvant être composé des différents éléments chimiques suivants : F, Na, Mg, Al, Si, P, S, K,17. Surface modification method according to one of claims 1 to 14, characterized in that said pigment is an inorganic pigment, preferably can be composed of the following different chemical elements: F, Na, Mg, Al, Si, P , S, K,
Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, ou W. Ca, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Se, Zr, Mo, Ru, Cd, Sn, Sb, or W.
18. Procédé de modification de surface selon la revendication 17, caractérisé en ce que ledit pigment est un pigment composite formé d'un ou plusieurs pigments inorganiques associés à un ou plusieurs excipients en présence ou non d'une laque, de préférence un pigment inorganique choisi dans le groupe constitué des pigments suivants, le Black Iran Oxide, Red Iran Oxide, Yellow Iran Oxide, Manganèse Violet, Ultramarine Blue, Titanium Dioxide, Chromium Oxide Green, Zinc Oxide, Iran Blue, Chromium Oxide Hydrated, Mica, Synthetic Fluorphlogopythe. 18. Surface modification method according to claim 17, characterized in that said pigment is a composite pigment formed of one or more inorganic pigments associated with one or more excipients in the presence or absence of a lacquer, preferably an inorganic pigment. selected from the group consisting of the following pigments: Black Iran Oxide, Red Iran Oxide, Yellow Iran Oxide, Manganese Violet, Ultramarine Blue, Titanium Dioxide, Chromium Oxide Green, Zinc Oxide, Blue Iran, Chromium Oxide Hydrated, Mica, Synthetic Fluorphlogopythe.
19. Procédé de préparation d'une poudre de pigments ou d'une composition comprenant au moins un pigment, de préférence destinée à être utilisée en cosmétique, en peinture ou dans les encres, de préférence en cosmétique, caractérisé en ce qu'il comprend les étapes suivantes : 19. A process for preparing a pigment powder or a composition comprising at least one pigment, preferably intended for use in cosmetics, in paint or in inks, preferably in cosmetics, characterized in that it comprises the following steps:
1) la modification de la surface du pigment par une méthode selon l'une des revendications 1 à 18 ; et  1) the modification of the surface of the pigment by a method according to one of claims 1 to 18; and
2) une étape récupération dudit pigment ou de ladite composition comprenant au moins un pigment dont la surface a ainsi été modifiée obtenue à l'étape C) sous forme d'une poudre.  2) a recovery step of said pigment or of said composition comprising at least one pigment whose surface has thus been modified obtained in step C) in the form of a powder.
20. Pigment, revêtu d'acide gras, ou poudre de pigment susceptible d'être directement obtenu par le procédé selon l'une des revendications 1 à 19. 20. Pigment, coated with fatty acid, or pigment powder that can be obtained directly by the process according to one of claims 1 to 19.
21. Pigment revêtu d'acide gras selon la revendication 20, dans lequel la concentration d'acide gras est comprise entre 1 et 25 % en poids. The fatty acid coated pigment of claim 20, wherein the concentration of fatty acid is from 1 to 25% by weight.
22. Composition comprenant un pigment selon la revendication 20 ou 21, dans un mélange avec un ingrédient pharmaceutiquement ou cosmétiquement acceptable. 22. A composition comprising a pigment according to claim 20 or 21, in a mixture with a pharmaceutically or cosmetically acceptable ingredient.
23. Composition comprenant un pigment selon la revendication 20 ou 21 ou poudre obtenue par le procédé selon selon la revendication 19, destinée à être utilisée en cosmétique, dans les encres ou en peinture, de préférence en cosmétique. 23. A composition comprising a pigment according to claim 20 or 21 or powder obtained by the process according to claim 19, for use in cosmetics, inks or in paint, preferably in cosmetics.
24. Composition cosmétique selon la revendication 23, caractérisé en ce qu'elle est contenue dans un far à paupières, un far à joues, un rouge à lèvres, une crème, un gel, un pain de savon ou toute forme de produit cosmétique.  24. Cosmetic composition according to claim 23, characterized in that it is contained in an eyeshadow, a cheek powder, a lipstick, a cream, a gel, a bar of soap or any form of cosmetic product.
25. Composition selon l'une quelconque des revendications 22 à 24 caractérisé en ce que la valeur de dE reste inférieure ou égale à 2 sur un laps de temps d'au moins 36 mois. 25. Composition according to any one of claims 22 to 24 characterized in that the value of dE remains less than or equal to 2 over a period of time of at least 36 months.
26. Utilisation d'un pigment selon l'une quelconque des revendications 20 ou 21 afin de stabiliser le dE d'une composition à une valeur inférieure ou égale à 2 sur un laps de temps d'au moins 36 mois. 26. Use of a pigment according to any one of claims 20 or 21 to stabilize the dE of a composition to less than or equal to 2 over a period of time of at least 36 months.
PCT/EP2013/075009 2012-11-28 2013-11-28 Treatment of organic and inorganic pigments by means of a method using natural plant oils WO2014083126A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1261352 2012-11-28
FR1261352A FR2998575B1 (en) 2012-11-28 2012-11-28 TREATMENTS OF ORGANIC AND INORGANIC PIGMENTS BY A PROCESS USING NATURAL VEGETABLE OILS

Publications (1)

Publication Number Publication Date
WO2014083126A1 true WO2014083126A1 (en) 2014-06-05

Family

ID=47754701

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/075009 WO2014083126A1 (en) 2012-11-28 2013-11-28 Treatment of organic and inorganic pigments by means of a method using natural plant oils

Country Status (2)

Country Link
FR (1) FR2998575B1 (en)
WO (1) WO2014083126A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3063902B1 (en) * 2017-03-15 2020-11-27 Adeline Constance METHOD OF MANUFACTURING POWDERS INTENDED FOR MAKE-UP OR COSMETIC SKIN CARE AND COSMETIC COMPOSITION CONTAINING THEM.

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US606914A (en) 1898-07-05 John w
US4627876A (en) 1982-11-25 1986-12-09 Basf Farben & Fasern Ag Printing ink
US4648908A (en) 1984-02-28 1987-03-10 Pola Chemical Industries Inc. Coated pigment and cosmetic materials comprising the same
US4863800A (en) 1987-03-06 1989-09-05 Miyoshi Kasei Co., Ltd. Surface-treated pigment material
EP0477622B1 (en) 1990-09-17 1994-12-28 MERCK PATENT GmbH Deposition of cosmetically functional material onto pigments and fillers
WO1995011943A1 (en) 1993-10-28 1995-05-04 Western Mining Corporation Limited Pigment extenders

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US606914A (en) 1898-07-05 John w
US4627876A (en) 1982-11-25 1986-12-09 Basf Farben & Fasern Ag Printing ink
US4648908A (en) 1984-02-28 1987-03-10 Pola Chemical Industries Inc. Coated pigment and cosmetic materials comprising the same
US4863800A (en) 1987-03-06 1989-09-05 Miyoshi Kasei Co., Ltd. Surface-treated pigment material
EP0477622B1 (en) 1990-09-17 1994-12-28 MERCK PATENT GmbH Deposition of cosmetically functional material onto pigments and fillers
WO1995011943A1 (en) 1993-10-28 1995-05-04 Western Mining Corporation Limited Pigment extenders
US5486233A (en) * 1993-10-28 1996-01-23 Western Mining Corporation Limited Pigment extenders

Also Published As

Publication number Publication date
FR2998575A1 (en) 2014-05-30
FR2998575B1 (en) 2015-03-13

Similar Documents

Publication Publication Date Title
EP0880564B1 (en) Titanium dioxide particles
EP0471054B1 (en) Water resistant composition for coating eyelashes, and preparation method therefor
CA2259281C (en) Titanium dioxide particles, method for their preparation and their use in cosmetics, varnish and surface coating
FR2747669A1 (en) PROCESS FOR THE PREPARATION OF HOLLOW SILICA PARTICLES
FR2964663A1 (en) COSMETIC COMPOSITION COMPRISING COLORING MATTER, COLORING MATERIAL, AND COSMETIC TREATMENT PROCESS
WO2012120098A2 (en) Hydrophilic treated pigments dispersible in a cosmetic composition
FR2729132A1 (en) Composite particles for use in cosmetics e.g. in anti-UV compsns.
FR2833163A1 (en) Solid mascara composition comprises a non-ionic surfactant, a film forming polymer and a wax in an aqueous mixture
FR3029786A1 (en) DISPERSION OF POLYMER PARTICLES IN A NONAQUEOUS MEDIUM AND USE IN COSMETICS
EP1157072B1 (en) Organic sol and solid compound based on titanium oxide and an amphiphilic compound and preparation methods
WO2013050560A1 (en) Method of surface treatment of micro/nanoparticles by chemical means and its application to obtaining a pigment composition intended for the field of cosmetics, paint or inks
FR2841256A1 (en) DISPERSIONS OF PIGMENTS, AND COSMETIC PRODUCTS CONTAINING SAME
US20050257718A1 (en) Natural Pearl in Butylene Glycol
EP4045566B1 (en) Biosourced gelling polyamides
WO2014083126A1 (en) Treatment of organic and inorganic pigments by means of a method using natural plant oils
FR2981846A1 (en) Aqueous pigment dispersion, useful as cosmetic composition including make-up foundation, mascara or eyeliner, comprises pigment comprising metallic oxide, suspending agent, dispersing agent e.g. citric acid, and water and glycerin
FR3030260A1 (en) COMPOSITION COMPRISING STABILIZED POLYMER PARTICLES AND NON-IONIC SURFACTANT
WO2019197646A1 (en) Pigment composition comprising a pigment treated with phytic acid
EP1828318A1 (en) Metal pigment composition
FR3054436A1 (en) PROCESS FOR THE MANUFACTURE OF A COMPACT POWDER COSMETIC MATERIAL AND SUCH A MATERIAL
KR102266248B1 (en) Particulate composition, liquid composition, method for producing particulate composition, surface modifier, method for improving water dispersibility
WO2004082656A1 (en) Monoi butter, novel cosmetic and/or dermatological compositions comprising monoi butter and uses thereof
FR3058891A1 (en) FAT COSMETICS
WO2023166204A1 (en) Cosmetic composition applicable to the skin and based on a volatile mixture of alkanes
WO1998026754A1 (en) Cosmetic composition in the form of an organic solution or dispersion containing at least a polymeric colouring agent

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13796093

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: CONSTATATION DE LA PERTE D UN DROIT CONFORMEMENT A LA REGLE 112(1) CBE (OEB FORM 1205A EN DATE DU 02/09/2015)

122 Ep: pct application non-entry in european phase

Ref document number: 13796093

Country of ref document: EP

Kind code of ref document: A1