FR3097757A1 - : PROCESS FOR TREATMENT OF KERATINIC MATERIALS IMPLEMENTING AN ACRYLIC ANHYDRIDE POLYMER IN OILY DISPERSION, WITH A PLASTICIZER, AND AN AMINE COMPOUND - Google Patents

Abstract

Title: PROCESS FOR TREATMENT OF KERATINIC MATERIALS IMPLEMENTING AN ACRYLIC POLYMER OF ANHYDRIDE IN OILY DISPERSION, OF A PLASTICIZER, AND OF AN AMINE COMPOUND The present invention relates to a process for the treatment of keratin materials, preferably human skin, in particular the lips, or a process for treating keratin fibers, in particular human fibers such as the hair, in at least two steps, firstly implementing the application to said materials of an oily dispersion A) comprising i) particles copolymers of alkyl acrylates and acrylic anhydrides, ii) stabilizers, iii) one or more hydrocarbon oils; then in a second step the application to said materials of a composition (B) comprising iv) one or more amino compounds, it being understood that the method of the invention uses v) one or more plasticizer (s), and vi) one or more cosmetic active agent (s) chosen from a) dyes and / or pigments, b) active agents for caring for keratin materials, preferably the skin, and c) UV filters and d) their mixtures; ingredients v) and vi) possibly being found in composition (A), and / or in composition (B), and / or in another composition (C). The subject of the invention is also a kit with several compartments comprising the ingredients i) to vi). A subject of the invention is also an anhydrous oily dispersion (A) comprising v) one or more plasticizer (s). The process of the invention makes it possible to obtain a treatment of said keratin materials resistant in particular to sweat, shower gels, water and fatty substances, in particular vegetable or animal edible oils. The process for treating keratin materials of the present application is also suitable for making up the skin or the lips, such as foundations and lipsticks.

Description

: PROCESS FOR THE TREATMENT OF KERATIN MATERIALS USING AN ACRYLIC POLYMER OF ANHYDRIDE IN OILY DISPERSION, A PLASTICIZER, AND AN AMINE COMPOUND

The present invention relates to a method for treating keratin materials, preferably human skin, in particular the lips, or a method for treating keratin fibers, in particular human fibers such as the hair, in at least two steps implementing in a first step the application to said materials of an oily dispersion A) comprising i) particles of copolymers of alkyl acrylates and acrylic anhydrides, ii) stabilizing agents, iii) one or more hydrocarbon oils; then in a second step the application to said materials of a composition (B) comprising iv) one or more amine compounds, it being understood that the process of the invention uses v) one or more plasticizer(s), and vi) one or more cosmetic active ingredient(s) chosen from a) dyes and/or pigments, b) active ingredients for the care of keratin materials, preferably the skin and c) UV filters as well as d) their mixtures; the ingredients v) and vi) possibly being in composition (A), and/or in composition (B), and/or in another composition (C). The invention also relates to a multi-compartment kit comprising the ingredients i) to vi). A subject of the invention is also an anhydrous oily dispersion (A) comprising v) one or more plasticizer(s).

In the field of dyeing keratin fibers, it is already known to dye keratin fibers by various techniques using direct dyes for non-permanent dyes or dye precursors for permanent dyes.

Non-permanent coloring or direct coloring consists in dyeing the keratin fibers with dye compositions containing direct dyes. These dyes are colored and coloring molecules with an affinity for keratin fibres. They are applied to the keratin fibers for the time necessary to obtain the desired coloration, then rinsed off.

The conventional dyes which are used are in particular dyes of the nitrobenzene, anthraquinone, nitropyridine, azo, xanthene, acridine, azine, triarylmethane type or natural dyes.

Some of these dyes can be used under lightening conditions, which makes it possible to obtain visible colorations on dark hair.

It is also known to dye keratin fibers permanently by oxidation dyeing. This coloring technique consists in applying to the keratin fibers a composition containing dye precursors such as oxidation bases and couplers. These precursors under the action of an oxidizing agent will form one or more colored species in the hair.

The variety of molecules involved in oxidation bases and couplers makes it possible to obtain a rich palette of colors and the resulting colorations are generally permanent, powerful, and resistant to external agents, in particular to light, bad weather, washing, perspiration and rubbing.

To be visible on dark hair, these two coloring techniques require prior or simultaneous bleaching of the keratin fibres. This bleaching step implemented with an oxidizing agent such as hydrogen peroxide or persalts leads to a significant degradation of the keratin fibres, which alters their cosmetic properties. The hair then tends to become rough, more difficult to disentangle and more fragile.

Another coloring method is to use pigments. Indeed, the use of pigment on the surface of keratin fibers generally makes it possible to obtain visible colorings on dark hair since the pigment on the surface masks the natural color of the fiber. The use of pigment for coloring keratin fibers is for example described in patent application FR 2 741 530, which recommends the use for the temporary coloring of keratin fibers of a composition comprising at least one dispersion of film-forming polymer particles. comprising at least one acid function and at least one pigment dispersed in the continuous phase of said dispersion.

The colors obtained by this method of coloring have the disadvantage of being eliminated from the first shampoo.

It is also known from patent application FR 2 907 678 to produce colored coatings for the hair from a composition comprising a polysiloxane/polyurea block copolymer and a pigment. However, with such a composition, the coatings obtained are not always very homogeneous and the individualization of the hair is not always very good.

It is also known from patent EP 1 392 222 to use a cosmetic composition for the care and/or treatment of keratin materials comprising a supramolecular polymer comprising a polymer backbone and at least two groups capable of forming at least three hydrogen bonds, and of patent EP 1 435 900 to use a hair composition comprising a supramolecular polymer comprising a polymeric backbone and at least two groups capable of forming at least three hydrogen bonds and a surfactant or a hair conditioning agent.

During the aging process, different signs appear on the skin, very characteristic of this aging, resulting in particular in a modification of the structure and functions of the skin. The main clinical signs of skin aging are in particular the appearance of fine lines and deep wrinkles, which increase with age.

It is known to treat these signs of aging by using cosmetic or dermatological compositions containing active agents capable of combating aging, such as α-hydroxy acids, β-hydroxy acids and retinoids. These active ingredients act on wrinkles by eliminating dead skin cells and accelerating the cell renewal process. However, these active agents have the drawback of only being effective for the treatment of wrinkles after a certain application time. However, it is increasingly sought to obtain an immediate effect from the active agents used, leading rapidly to a smoothing of wrinkles and fine lines and to the disappearance of signs of fatigue.

Cosmetic products often require the use of a film-forming polymer to obtain a deposit of the product on keratin materials with good cosmetic properties. In particular, it is necessary for the film-forming deposit to have good hold, in particular for the deposit not to transfer on contact with fingers, clothing, as well as good hold in contact with water, in particular rain. or when showering or even from perspiration as well as food fats, in particular edible oils.

It is known to use dispersions of polymer particles of nanometric size, in organic media such as hydrocarbon oils. The polymers are used in particular as a film-forming agent in make-up products such as mascaras, eyeliners, eye shadows or lipsticks. Document EP 0 749 747 describes in the examples dispersions in hydrocarbon oils (paraffin oil, isododecane) of acrylic polymers stabilized with polystyrene/copoly(ethylene-propylene) diblock copolymers. The film obtained after application of the dispersion to the skin is not very shiny. Document FR 1 362 795 also describes the use of dispersions of surface-stabilized polymer particles containing hydrocarbon oils for making up the lips and eyelashes. Document WO 2010/046229 describes dispersions in isododecane of stabilized acrylic polymers by stabilizing polymers. In prepared by radical polymerization controlled by reversible chain transfer. Document FR 1 362 795 describes the use of a dispersion of surface-stabilized polymer particles containing hydrocarbon oils for making up the lips and eyelashes.

Thus, the object of the present invention is to provide a method for treating keratin fibers with good resistance to attacks such as brushing, non-bleeding, resistant to sweat, light and bad weather, resistant to shampoos and to the various aggressions that said fibers may undergo without degradation of said fibers and while retaining perfectly individualized keratin fibers.

Another object of the present invention is to provide a method for treating keratinous materials, in particular the skin, preferably human, and more preferably the face, which has good resistance to external aggressions, and in the time, of the action of the cosmetic active agent(s) such as the tensor effect, of care, of protection against Ultraviolet (UV) radiation, but also good persistence of make-up such as lip make-up.

The technical problem has been solved by the method of the invention which is a method for treating keratin materials, preferably human, in particular the skin, and more preferably the face such as the lips, or keratin fibers, in particular human , such as hair, comprising:
1) the application to said materials of an oily dispersion (A), preferably anhydrous, comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s):
a) (C ₁ -C ₄ )(alkyl)acrylate (C ₁ -C ₄ )alkyl, preferably (meth)acrylate (C ₁ -C ₄ )alkyl and
b) an ethylenically unsaturated anhydride compound, preferably maleic anhydride; and
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from:
c) polymers of (C ₁ -C ₆ )(alkyl)acrylate (C ₃ -C ₁₂ )cycloalkyl monomers; and
d) copolymers of (C ₁ -C ₆ )(alkyl)acrylate, (C ₃ -C ₁₂ )cycloalkyl and (C ₁ -C ₄ )(alkyl)acrylate (C ₁ -C ₄ )alkyl; and
iii) one or more hydrocarbon oil(s); followed by
2) the application to said materials of a composition (B), preferably anhydrous, comprising:
iv) one or more amino compound(s) chosen from:
e) polyamino compounds having several primary amine and/or secondary amine groups, and
f) amino alkoxysilanes,
it being understood that the process of the invention uses v) one or more plasticizer(s), and vi) one or more cosmetic active ingredient(s) chosen from a) dyes and/or pigments, b) active ingredients for the care of keratin materials, in particular the skin, and c) UV filters as well as d) mixtures thereof, the ingredients v) and vi) possibly being found in composition (A), and/or in composition ( B), and/or in another composition (C).

This process for treating keratin materials in at least two successive steps using, in a first step, the oily dispersion (A) as defined above and then, in a following step, a composition (B) comprising one or more amino compounds as defined above and optionally a composition (C), makes it possible to obtain a treatment of said keratinous materials resistant in particular to sweat, shower gels, water and fatty substances, in particular vegetable edible oils or animal, and more particularly vegetable, such as olive oil, sunflower, walnut, hazelnut, etc.

The process for treating keratin materials of the present application is also suitable for making up the skin or the lips, such as foundations and lipsticks.

The present patent application also relates to a process, in particular cosmetic, for caring for or making up the skin or the lips, more particularly the skin of the face, in particular the wrinkled skin, comprising the topical application to the skin or of the lips, in particular cosmetic compositions, (A) and (B) and optionally (C), as described above.

The invention also relates to a process, in particular cosmetic, for caring for the skin, more particularly the skin of the face, in particular the wrinkled skin, comprising the topical application to the skin of the compositions, in particular cosmetics, (A) , and (B) and optionally (C), as previously described.

The method of the present patent application is in particular intended to smooth the human skin of the face and/or the body and/or to reduce or erase the signs of skin aging, in particular to reduce or erase wrinkles and/or fine lines. skin.

A subject of the invention is also the cosmetic use as a tightening agent for the skin, in particular for wrinkled skin, of compositions, in particular cosmetics, (A), and (B) and optionally (C), such as previously described.

The term “ tensioning agent ” is understood to mean compounds capable of having an apparent tensioning effect, that is to say of smoothing the skin and reducing, or even eliminating, wrinkles and fine lines immediately.

The tightening effect can be characterized by an in vitro shrinkage test.

Within the meaning of the present invention, and unless a different indication is given:
- an " alkyl radical " is a saturated C ₁ -C ₈ hydrocarbon group, linear or branched, in particular C ₁ -C _6, preferably C ₁ -C ₄ such as methyl, ethyl, isopropyl, and t- butyl;
- an “ alkylene radical ” is a divalent C ₁ -C ₈ saturated hydrocarbon group, linear or branched, in particular C ₁ -C _6, preferably C ₁ -C ₄ such as methylene, ethylene or propylene;
- a “ cycloalkyl ” radical is a saturated cyclic hydrocarbon group comprising from 1 to 3 rings, preferably 2 rings, and comprising from 3 to 13 carbon atoms, preferably between 5 and 10 carbon atoms, such as cyclopentyl, cyclohexyl, cycloheptyl, norbornyl or isobornyl, the cycloalkyl radical possibly being substituted by one or more (C ₁ -C ₄ )alkyl groups such as methyl, preferably the cycloalkyl radical is an isobornyl group.
- a “ cyclic ” radical is a cyclic hydrocarbon group, saturated or unsaturated, aromatic or non-aromatic, comprising from 1 to 3 rings, preferably 1 ring, and comprising from 3 to 10 carbon atoms such as cyclohexyl or phenyl;
- an " aryl " radical is a hydrocarbon cyclic radical, aromatic unsaturated, comprising from 6 to 12 carbon atoms, mono or bicyclic, fused or not, preferably the aryl group comprises 1 ring and 6 carbon atoms such as phenyl;
- an " aryloxy " radical is an aryl-oxy radical, ie aryl-O- with aryl as defined above, preferably phenoxy;
- an " aryl(C ₁ -C ₄ )alkoxy " radical is an aryl-(C ₁ -C ₄ )alkyl-O- radical, preferably benzoxy;
- a " polysaccharide " is a polysaccharide sugar which is a polymer made up of several oses linked together by O-saccharide bonds, said polymers being made up of monosaccharide units as defined above, said monosaccharide units comprising at least 5 carbon atoms , preferably 6, particularly the monosaccharide units are linked together at 1,4 or 1,6 in an α (alpha) or β (beta) anomer, each sugar unit possibly having the L or D configuration, as well as its salts and its solvates such as the hydrates of said monosaccharides; they are more particularly polymers formed from a certain number of monosaccharides (or monosaccharides) having the general formula: -[C _x (H ₂ O) _y )] _n - with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is comprised inclusively between 5 and 7, preferably x = 6, and y is an integer which represents x - 1, and n is an integer greater than or equal to 2, particularly comprised inclusively between 3 and 3000, more particularly between 5 and 2500, preferentially between 10 and 2300;
- by “ with amine group(s) ” is meant that the polysaccharide(s) are substituted by one or more amino group(s) NR ₁ R ₂ ie at least one of the hydroxy groups of at least one osidic unit is replaced by an NR ₁ R ₂ group, with R ₁ and R ₂ , identical or different, representing i) a hydrogen atom, ii) a (C ₁ -C ₆ )alkyl group, ii) –C( Y)-(Y') _p -R' ₁ with Y and Y', identical or different, representing an oxygen, sulfur or N(R' ₂ ) atom, preferably oxygen, p = 0 or 1, of preference 0; and R' ₁ and R' ₂ representing i) or ii) of R ₁ and R ₂ defined above, and in particular R' ₁ denoting a (C ₁ -C ₆ )alkyl group such as methyl. Preferably R ₁ and R ₂ represent a hydrogen atom.

The oily dispersion (A)

The process of the invention uses at least one oily dispersion (A) of i) particles of at least one surface-stabilized polymer with ii) at least one stabilizing agent in a preferably anhydrous medium, additionally containing iii) at least one hydrocarbon oil.

In addition, the dispersions according to the invention consist of particles, generally spherical, of at least one surface-stabilized polymer, in a non-aqueous medium.

Polymer particles i)

The particle(s) of the dispersion of the process of the invention consists of one or more ethylenic copolymer(s) of a) (C ₁ -C ₄ )(alkyl)acrylate of (C ₁ - C ₄ ) alkyl and b) an ethylenically unsaturated anhydride compound.

By “ ethylenic copolymer ” is meant a polymer resulting from the polymerization of two monomers: monomer a) (C ₁ -C ₄ )(alkyl)acrylate of (C ₁ -C ₄ )alkyl and monomer b) of anhydride compound with ethylenic unsaturation.

By “ ethylenically unsaturated anhydride compound ” is meant a carboxylic acid anhydride compound comprising at least one ethylenic unsaturation –(R _a )C=C(R _b )–, –C(R _a )=C(R _b )– R _c or >C=C(R _a )–R _b , with R _a , R _b , and R _c , identical or different, representing a hydrogen atom or a (C ₁ -C ₄ )alkyl group such as methyl , preferably hydrogen. In particular, the ethylenically unsaturated anhydride compound is a cyclic compound, preferably having 5 or 6 members, and comprising ethylenic unsaturation.

According to a preferred embodiment of the invention, the polymer constituting the particles i) is an acrylate copolymer:
a) of formula H ₂ C=C(R)-C(O)-O-R' with R representing a hydrogen atom or a (C ₁ -C ₄ )alkyl group such as methyl, and R' representing a (C ₁ -C ₄ )alkyl such as methyl or ethyl, preferably C ₁ -C ₄ alkyl (meth)acrylate; and
b) an ethylenically unsaturated anhydride monomer

In particular, the polymer of the particles is a polymer of C ₁ -C ₄ alkyl (meth)acrylate and of ethylenically unsaturated anhydride monomer.

The monomers a) are preferably chosen from methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, (meth)acrylate n-butyl, tert-butyl (meth)acrylate.

Advantageously, a C ₁ -C ₄ alkyl acrylate monomer is used. Preferably a) is chosen from methyl acrylate and ethyl acrylate.

The polymer of the particles also comprises an ethylenically unsaturated anhydride monomer b).

Preferably, the ethylenically unsaturated anhydride compound(s) b) of the invention are chosen from derivatives of maleic anhydride (Ib) and itaconic anhydride (IIb):

Formulas (Ib) and (IIb) in which R _a , R _b and R _c , identical or different, representing a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably R _a , R _b , and R _c represent a hydrogen atom.

More preferably, the ethylenically unsaturated anhydride monomer of the invention is of formula (Ib) and even more preferably is maleic anhydride.

According to a preferred embodiment of the invention, the polymer(s) of the particles comprise, or consist essentially of, from 80 to 99.99% by weight of monomer a) and from 0.01 to 20% by weight of monomer b), relative to the total weight of the polymer.

The polymer of the particles can be chosen from:
- methyl acrylate/maleic anhydride copolymers;
- ethyl acrylate/maleic anhydride copolymers; and
- methyl acrylate/ethyl acrylate/maleic anhydride copolymers.

Advantageously, the polymer of the particles is a non-crosslinked polymer.

The polymer of the particles of the dispersion preferably has a number average molecular weight ranging from 2,000 to 10,000,000.

The polymer of the particles may be present in the dispersion in a content ranging from 20 to 60% by weight, relative to the total weight of the dispersion (A), in particular between 21% to 58.5% by weight, relative to the total weight of the dispersion (A), preferably ranging from 30 to 50% by weight, relative to the total weight of the dispersion (A), more preferably ranging from 36% to 42% by weight relative to the total weight of the scatter (A).

The stabilizing agent(s) ii)

The dispersion (A) according to the invention also comprises one or more stabilizing agents ii). Preferably only one type of stabilizer ii) is used in the invention.

The stabilizing agent(s) of the invention is (are) constituted by ethylenic polymers chosen from c) polymers of (C ₁ -C ₆ )(alkyl)acrylate (C ₃ -C ₁₂ )cycloalkyl monomers; and d) copolymers of (C ₁ -C ₆ )(alkyl)acrylate, (C ₃ -C ₁₂ )cycloalkyl and (C ₁ -C ₄ )(alkyl)acrylate (C ₁ -C ₄ )alkyl.

According to a preferred embodiment of the invention, the stabilizing agent ii) consists of ethylenic polymers chosen from: c) polymers of monomers of formula H₂C=C(R)-C(O)-O-R’’ with R representing a hydrogen atom or group (C₁-VS₄)alkyl such as methyl, and R’’ representing a group (C₅-VS₁₀)cycloalkyl such as norbornyl, or isobornyl preferably isobornyl ; and
d) copolymers of H₂C=C(R)-C(O)-O-R’ and of H₂C=C(R)-C(O)-O-R'' with R, R' and R'' as previously defined.

In particular, the stabilizing agent ii) is an isobornyl (meth)acrylate polymer selected from isobornyl (meth)acrylate homopolymer and random copolymers of isobornyl (meth)acrylate and isobornyl (meth)acrylate. C ₁ -C ₄ alkyl preferably present in a weight ratio of isobornyl (meth)acrylate/C ₁ -C ₄ alkyl (meth)acrylate greater than 4;Advantageously, said weight ratio ranges from 4.5 at 19.

For these random copolymers, the defined weight ratio makes it possible to obtain a stable polymer dispersion, in particular after storage for 7 days at room temperature.

Advantageously, the stabilizing agent is chosen from:
- isobornyl acrylate homopolymers,
- isobornyl acrylate/methyl acrylate random copolymers,
- random copolymers of isobornyl acrylate/ethyl acrylate, and
- random copolymers of isobornyl acrylate/methyl acrylate/ethyl acrylate according to the weight ratio described above.

Advantageously, the set ii) stabilizing agent(s)+i) particle(s) of polymer(s) present in the dispersion (A) comprises from 10 to 50% by weight of copolymers d) and from 50 to 90% by weight of polymers c), relative to the total weight of the whole ii) stabilizing agent(s)+i) particle(s) of polymer(s).

Preferably, the set ii) stabilizing agent(s)+ii) particle(s) of polymer(s) present in the dispersion comprises from 15 to 30% by weight of copolymers d) and from 70 to 85% by weight of polymers c), relative to the total weight of the whole ii) stabilizing agent(s)+i) particle(s) of polymer(s).

The hydrocarbon oil(s) iii)

Dispersion (A) according to the invention comprises one or more identical or different hydrocarbon-based oils, preferably identical.

By “ oil ” is meant a fatty substance that is liquid at ambient temperature at ambient temperature (25° C.) and atmospheric pressure.

The term " hydrocarbon oil " means an oil formed essentially, or even consisting, of carbon and hydrogen atoms, and optionally of oxygen and nitrogen atoms, and not containing any silicon or fluorine. It may contain hydroxy, ester, ether, carboxylic acid, amine and/or amide groups.

Hydrocarbon oil can be volatile or non-volatile

According to a preferred embodiment of the invention, the hydrocarbon oil(s) are volatile or are a mixture of different volatile oils more preferably chosen from isododecane and octyldodecanol.

According to another particular embodiment, the hydrocarbon oil or oils are a mixture of a volatile oil and a non-volatile oil.

By “ volatile oil ”, is meant an oil (or non-aqueous medium) capable of evaporating on contact with the skin in less than one hour, at room temperature and at atmospheric pressure. The volatile oil is a volatile cosmetic oil, liquid at ambient temperature, having in particular a non-zero vapor pressure, at ambient temperature and at atmospheric pressure, in particular, having a vapor pressure ranging from 0.13 Pa to 40,000 Pa (10 ^-3 to 300 mm Hg), and preferably ranging from 1.3 Pa to 13,000 Pa (0.01 to 100 mm Hg), and preferably ranging from 1.3 Pa to 1300 Pa (0.01 to 10mm Hg).

By " non-volatile oil " is meant an oil having a vapor pressure of less than 0.13 Pa.

As volatile silicone oils, mention may be made of volatile linear or cyclic silicone oils, in particular those having a viscosity of  8 centistokes (cSt) (8 x 10 ^-6 m ² /s), and having, in particular, from 2 to 10 silicon atoms, and in particular, from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms. As volatile silicone oil that can be used in the invention, mention may be made, in particular, of dimethicones with a viscosity of 5 and 6 cSt, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, l hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.

As non-volatile silicone oils, mention may be made of non-volatile, linear or cyclic polydimethylsiloxanes (PDMS); polydimethylsiloxanes comprising alkyl, alkoxy and/or phenyl groups, pendent or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones, phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy, diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenyl ethyl trimethyl-siloxysilicates and pentaphenyl silicone oils different from the plasticizers v) of the invention.

The hydrocarbon-based oil may be chosen from hydrocarbon-based oils having from 8 to 14 carbon atoms, and in particular:
- branched C ₈ -C ₁₄ alkanes such as C ₈ -C ₁₄ isoalkanes of petroleum origin (also called isoparaffins) such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, and for example the oils sold under the trade names Isopars' or Permetyls,
- linear alkanes, for example such as n-dodecane (C12) and n-tetradecane (C14) sold by Sasol respectively under the references PARAFOL 12-97 and PARAFOL 14-97 , as well as their mixtures, the undecane- tridecane, the mixtures of n-undecane (C11) and n-tridecane (C13) obtained in examples 1 and 2 of application WO2008/155059 from the company Cognis, and mixtures thereof.
- short chain esters (having 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate
- hydrocarbon oils of plant origin such as triglycerides consisting of esters of fatty acids and glycerol, the fatty acids of which may have chain lengths varying from C ₄ to C ₂₄ , the latter possibly being linear or branched, saturated or unsaturated; these oils are in particular triglycerides of heptanoic acid or octanoic acid, or alternatively wheat germ, sunflower, grapeseed, sesame, corn, apricot, castor, shea, avocado, olive, soy, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, bancoulier, passionflower, muscat rose; shea butter; or caprylic/capric acid triglycerides such as those sold by Stéarineries Dubois or those sold under the names Miglyol 810 ^® , 812 ^® and 818 ^® by Dynamit Nobel,
- synthetic ethers having 10 to 40 carbon atoms;
- linear or branched hydrocarbons, of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam ®, squalane, paraffin oils, and mixtures thereof,
- synthetic esters such as oils of formula R ₁ C(O)-OR ₂ in which R ₁ represents the residue of a linear or branched fatty acid comprising from 1 to 40 carbon atoms and R ₂ represents a hydrocarbon chain in particular branched chain containing from 1 to 40 carbon atoms provided that R ₁ + R ₂ is ³ 10, such as Purcellin's oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, benzoates of C ₁₂ to C ₁₅ alcohols, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethyl-hexyl palmitate, isostearyl isostearate, 2-hexyl laurate -decyl, 2-octyl-decyl palmitate, 2-octyl-dodecyl myristate, heptanoates, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, di-isostearyl malate, 2-octyl-dodecyl lactate; polyol esters and pentaerythritol esters,
- fatty alcohols that are liquid at room temperature with a branched and/or unsaturated carbon chain having from 12 to 26 carbon atoms, such as octyl dodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, and 2-undecylpentadecanol.

The dispersion (A) in addition to the hydrocarbon oil, can comprise a silicone oil. If silicone oil is present in the dispersion (A), it is preferably present in an amount which does not exceed 10% by weight relative to the weight of the dispersion (A), more particularly in an amount less than 5% and more preferably 2%. The term “silicone oil” means an oil comprising at least one silicon atom, and in particular at least one Si—O group. Silicone oil can be volatile or non-volatile.

According to a particular embodiment, the dispersion (A) comprises a hydrocarbon oil in a content ranging from 60 to 100% by weight of the total weight of the oils present in the composition and from 0 to 40% by weight of silicone oil. According to a preferred mode of the invention, the composition contains as oil only a hydrocarbon oil.

Advantageously, the hydrocarbon oil(s) of the invention are apolar, i.e. formed solely of carbon and hydrogen atoms.

The hydrocarbon-based oil or oils are preferably chosen from hydrocarbon-based oils having from 8 to 14 carbon atoms, in particular volatile ones, more particularly the apolar oils, described previously.

Preferably, the hydrocarbon oil(s) of the invention are isododecane.

According to another advantageous embodiment of the invention, the hydrocarbon oil or oils are a mixture of non-volatile and volatile oil, preferably the mixture comprises isododecane as volatile oil. In particular, in the mixture, the non-volatile oil is a phenyl silicone oil preferably chosen from pentaphenyl silicone oils different from the plasticizers v) of the invention.

According to a particular embodiment of the invention, the compositions used in process (B) and (C) also comprise at least one oil as defined previously, in particular a hydrocarbon oil.

The polymer particles of the dispersion preferably have a number-average size ranging from 5 and 500 nm, in particular ranging from 10 to 400 nm, and better still ranging from 20 to 300 nm.

The final particle size is preferably greater than 100 nm. In particular a number-average size ranging from 100 nm and 500 nm; more particularly ranging from 150 nm to 400 nm, even more particularly ranging from 160 nm to 300 nm.

The average particle size is determined by conventional methods known to those skilled in the art. A MALVERN model NanoZS laser particle sizer (particularly well suited to submicronic dispersions) is used to measure the size distribution of these samples. The operating principle of this type of device is based on dynamic light scattering (DLS), also called quasi-elastic light scattering (QELS) or photon correlation spectroscopy (PCS).

The sample is pipetted into a single-use plastic tank (4 transparent sides, 1 cm side and 4 mL capacity) placed in the measuring cell. The data are analyzed on the basis of a cumulant method which leads to a unimodal particle size distribution characterized by an average diameter in intensity d(nm) and a polydispersity factor in sizes Q. The results can also be expressed in the form of data statistics such as D10; D50 (median), D90 and mode.

Other granulometry techniques make it possible to obtain this type of information, such as analysis of individual particle tracking (Nanoparticle Tracking Analysis, NTA), laser diffraction (DL), acoustic extinction spectroscopy (AES) , Doppler velocimetry by spatial filter or image analysis.

Dispersion preparation method (A)

Without this being limiting, in general, the dispersion according to the invention can be prepared in the following way:

The polymerization is carried out in " dispersion ", that is to say by precipitation of the polymer during formation, with protection of the particles formed with one or more stabilizing agents, preferably a stabilizing agent.
In a first step, the stabilizing polymer (or stabilizing agent ii)) is prepared by mixing the monomer or monomers constituting the stabilizing polymer c) or d), with vii) a radical initiator, in a solvent called synthesis solvent, and by polymerizing these monomers;
In a second stage, the monomers constituting the polymer of the particles i) are added to the stabilizing polymer formed in the preceding stage and the polymerization of these added monomers is carried out in the presence of the radical initiator.

When the non-aqueous medium is a non-volatile iii) hydrocarbon-based oil, the polymerization can be carried out in an apolar organic solvent (synthetic solvent) then add the non-volatile hydrocarbon-based oil (which must be miscible with said synthetic solvent) and distill selectively the synthesis solvent.

The plasticizer(s) v), is (are) added during the first step. According to another variant, the plasticizer(s) v), is (are) added during the second stage or after the second stage.

According to yet another variant, the plasticizer(s) v), is (are) added after the second step.

The cosmetic agent(s), preferably pigment(s), is (are) added during the first stage. According to another variant, the cosmetic agent(s), preferably pigment(s), is (are) added during the second stage or after the second stage.

A synthetic solvent is therefore chosen such that the monomers of the stabilizing polymer, and the radical initiator, are soluble therein, and the polymer particles obtained are insoluble therein so that they precipitate therein during their formation.

In particular, the synthesis solvent which is apolar organic is chosen, preferably chosen from alkanes such as heptane or cyclohexane.

When the non-aqueous medium is a volatile iii) hydrocarbon-based oil, the polymerization can be carried out directly in said oil, which therefore also acts as a synthesis solvent. The monomers must also be soluble therein, as well as the radical initiator, and the polymer of the particles obtained must be insoluble therein.

The cosmetic agent(s) v) preferably pigment(s) little(ven)t added during the first stage. According to another variant, the dye(s) and/or pigment(s) is (are) added during the second stage or after the second stage.

A synthetic solvent is therefore chosen such that the monomers of the stabilizing polymer, and the radical initiator, are soluble therein, and the polymer particles obtained are insoluble therein so that they precipitate therein during their formation.

In particular, the synthesis solvent which is apolar organic is chosen, preferably chosen from alkanes such as heptane or cyclohexane.

When the non-aqueous medium is a volatile iii) hydrocarbon-based oil, the polymerization can be carried out directly in said oil, which therefore also acts as a synthesis solvent. The monomers must also be soluble therein, as well as the radical initiator, and the polymer of the particles obtained must be insoluble therein.

The monomers are preferably present in the synthesis solvent, before polymerization, in a proportion of 5% to 45% by weight. All of the monomers can be present in the solvent before the start of the reaction, or part of the monomers can be added as the polymerization reaction progresses.

The polymerization is preferably carried out in the presence vii) of one or more radical initiators, in particular of the type:
- peroxide in particular chosen from tert-Butyl peroxy-2-ethylhexanoate: Trigonox 21S; 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane: Trigonox 141; tert-butyl peroxypivalate: Trigonox 25C75 from AkzoNobel; Where
- azo in particular chosen from AIBN: azobisisobutyronitrile; V50: 2,2'-azo-bis(2-amidinopropane) dihydrochloride.

The polymerization is preferably carried out at a temperature ranging from 70 to 110° C. and at atmospheric pressure.

The polymer particles i) are stabilized at the surface, when they form during the polymerization, thanks to the stabilizer ii).

The stabilization can be carried out by any known means, and in particular by direct addition of the stabilizer ii), during the polymerization.

The stabilizer ii) is preferably also present in the mixture before polymerization of the monomers of the polymer of the particles i). However, it is also possible to add it continuously, in particular when the monomers of the polymer of the particles i) are also continuously added.

It is possible to use from 10 to 30% by weight of the stabilizing agent(s) relative to the total weight of monomers used (stabilizing agents ii)+polymer particles i)), and preferably from 15 to 25% by weight.

The dispersion of polymer particles (A) advantageously comprises from 30 to 65% by weight of dry matter, relative to the total weight of said dispersion, and preferably from 40 to 60% by weight relative to the total weight of said dispersion.

The composition according to the invention preferably comprises a content of particle polymers i) + dispersant polymers ii) ranging from 1 to 50% by weight, relative to the total weight of composition (A), and preferably ranging from 2 to 30% in weight.

According to a preferred embodiment of the invention, the dispersion (A) according to the invention is an anhydrous composition.

By “ anhydrous ” dispersion or composition is meant a dispersion or composition containing less than 2% by weight of water, or even less than 0.5% of water, and in particular free of water. Where appropriate, such small amounts of water can in particular be supplied by ingredients of the composition which can contain residual amounts thereof.

According to another embodiment of the present patent application, the dispersion (A) is in an inverse emulsion, i.e. of the water-in-oil (W/O) or “water-in-oil (W/O)” type. In this case the composition comprises one or more surfactants, preferably nonionic. The inverse emulsions of (A) are preferably chosen in makeup and in particular in mascaras.

Composition (B)

Composition B of the process of the invention comprises one or more amine compounds iv).

The amino compound(s) iv)

The amine compounds used in the process of the invention are chosen from:
e) polyamines having several primary amine and/or secondary amine groups, and
f) amino alkoxysilanes,

The amino compound(s) used in the process according to the invention is (are) chosen in particular from amino alkoxysilane compounds, diamino compounds, triamino compounds.

According to a particular embodiment of the invention, the polyamino compound(s) particularly comprise from 2 to 20 carbon atoms, in particular the polyamino compound(s) compound is (are) not polymer(s).

By “ nonpolymeric ” compound(s) is meant one or more compound(s) which is or are not directly obtained by a polymerization reaction of monomers.

As polyamino compounds, mention may in particular be made of N-methyl-1,3-diaminopropane, N-propyl 1,3-diaminopropane, N-isopropyl 1,3-diaminopropane, N-cyclohexyl 1,3-diaminopropane, 2-(3-aminopropylamino) ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methyl bis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4 -diaminobutane, N,N-dimethyldipropylene, triamine, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine, ethylene diamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine, cystamine, xylene diamine, tris(2-aminoethyl)amine, spermidine.

According to another particular embodiment of the invention, the amino compound(s) iv) is (are) chosen from f) amino alkoxysilanes, such as those of formula (IVa):

(IVa)
Formula (IVa) in which:
- R'₁is a C hydrocarbon chain₁-VS₁₀, linear or branched, saturated or unsaturated, cyclic or acyclic, substituted by one or more groups chosen from the groups: i) primary amine NH₂or secondary N(H)R with R representing a group (C₁-VS₄)alkyl, ii) aryl or aryloxy substituted by an amino group, (C₁-VS₄)alkylamino or by a C aminoalkyl group₁-VS₄and iii) aldehyde –C(O)-H, carboxy –C(O)-OH, amide –C(O)-NH₂or urea –NH-C(O)-NH₂; R'₁is optionally interrupted in its hydrocarbon chain by one or more heteroatoms (in particular O, S, NH), a carbonyl group (CO), or their combination such as ester –C(O)-O-, or amide –C(O) -NH-, R'₁being bonded to the silicon atom directly via a carbon atom,
- R'₂and R'₃identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms,
- z denotes an integer ranging from 1 to 3,
- and x denotes an integer ranging from 0 to 2, with z+x =3.

Preferably, R′ ₂ represents an alkyl group comprising from 1 to 4 carbon atoms.

Preferably, R′ ₂ represents a linear alkyl group comprising from 1 to 4 carbon atoms.

Preferably, R′ ₂ represents the ethyl group.

Preferably, R′ ₃ represents an alkyl group comprising from 1 to 4 carbon atoms.

Preferably, R′ ₃ represents a linear alkyl group comprising from 1 to 4 carbon atoms.

Preferably, R′ ₃ represents the methyl or ethyl group.

Preferably R' ₁ is an acyclic chain.

Preferably R'1 is a C ₁ -C ₆ hydrocarbon chain, linear or branched, saturated or unsaturated, substituted by an amine group NH ₂ or N(H)R with R representing a C ₁ -C ₆ alkyl group, C ₃ -C ₆ cycloalkyl or C ₆ aromatic.

Preferably, R′ ₁ is a saturated linear C ₁ -C ₆ hydrocarbon chain substituted by an NH ₂ amine group.

More preferably, R′ ₁ is a saturated linear C ₂ -C ₄ hydrocarbon chain substituted by an NH ₂ amine group.

Preferably, R' ₁ is a saturated linear C ₁ -C ₆ hydrocarbon chain substituted by an amine group NH ₂ ,

R' ₂ represents an alkyl group comprising from 1 to 4 carbon atoms,

R′ ₃ represents an alkyl group comprising from 1 to 4 carbon atoms.

Preferably z is equal to 3.

Preferably, the amino alkoxysilane of formula (IVa) is chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.

Preferably, the amino alkoxysilane (IVa) is chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane.

Preferably the amino alkoxysilane (IVa) is 3-aminopropyl triethoxysilane (APTES).

Preferably, the amino compound(s) are chosen from 3-aminopropyltriethoxysilane (APTES), N-methyl-1,3-diaminopropane, N-propyl 1,3-diaminopropane, Nisopropyl1,3-diaminopropane, N- cyclohexyl 1,3-diaminopropane, 2-(3-aminopropylamino) ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methyl bis(3-aminopropyl)amine, N-( 3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylene triamine, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine , ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine.

Preferably, the amino compound is chosen from ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, 3-aminopropyltriethoxysilane (APTES).

More preferably, the amino compound is ethylenediamine or 3-aminopropyltriethoxysilane (APTES).

The amine compound(s) can also be chosen from e) polyamines having several primary amine and/or secondary amine groups and in particular amino polymers, in particular having a weight-average molecular weight ranging from 500 to 1,000,000, preferably ranging from from 500 to 500,000, and preferably ranging from 500 to 100,000.

As amino or polyamino polymers e) it is possible to use poly((C ₂ -C ₅ )alkylene imines), and in particular:
- polyethyleneimines and polypropyleneimines, in particular poly(ethyleneimine) (for example that sold under the reference 46,852-3 by the company Aldrich Chemical);
- poly(allylamine), for example that sold under the reference 47,913-6 by the company Aldrich Chemical);
- polyvinylamines and their copolymers, in particular with vinylamides; mention may in particular be made of vinylamine/vinylformamide copolymers such as those marketed under the name LUPAMIN® 9030 by the company BASF;
- polyamino acids having NH ₂ groups such as polylysine, for example that sold by the company JNC Corporation (formerly Chisso); amino dextran, such as that sold by the company CarboMer Inc;
- polyvinyl amino alcohol such as that sold by the company CarboMer Inc, copolymers based on acrylamidopropylamine;
- chitosan; and
- polydi(C ₁ -C ₄ )alkylsiloxanes, in particular polydimethylsiloxanes, comprising amine groups at the end of the chain or on the side chains, are particularly terminal or lateral amino(C ₁ -C ₆ )alkyl groups such as aminopropyl , more particularly those of formula (IVb) or (IVc) or (IVd):

(IVb)
Formula (IVb) in which R ^a , and R ^b , which are identical or different, preferably identical, represent a (C ₁ -C ₄ )alkyl group such as methyl, (C ₁ -C ₄ )alkoxy such as methoxy, aryl such as as phenyl, aryloxy such as phenoxy, aryl(C ₁ -C ₄ )alkyl such as benzyl, or aryl(C ₁ -C ₄ )alkoxy such as benzoxy, preferably (C ₁ -C ₄ )alkyl such as methyl, R ^c and R' ^c , identical or different, preferably identical, represent a hydrogen atom, a (C ₁ -C ₄ )alkyl group, an amino(C ₁ -C ₄ )alkyl or (C ₁ -C ₄ )alkylamino(C ₁ -C ₄ )alkyl, preferably a hydrogen atom or an amino(C ₁ -C ₄ )alkyl group such as aminoethyl; X represents a covalent bond, an oxygen atom, preferably a covalent bond, ALK and ALK', identical or different, preferably identical, represent a (C ₁ -C ₆ )alkylene group, preferably (C ₁ -C ₄ ) alkylene such as propylene; n representing an integer greater than 2 and more particularly the value of n is such that the weight-average molecular weight of the silicone is between 500 and 55,000;

Preferably, the polydi(C ₁ -C ₄ )alkylsiloxanes of formula (IVb) are of the following formula (IV'b) or (IV''b):

(IV'b)

(IV''b)
formula (IVb) in which the value of n is such that the weight-average molecular weight of the silicone is between 500 and 55,000. As an example of amino silicone (IVb) or (IV'b), mention may be made of those sold under the names “DMS-A11”, “DMS-A12”, “DMS-A15”, “DMS-A21”, “DMS-A31”, “DMS-A32, “DMS-A35” by the company GELEST;
Formula (IV''b) with R ^c , R' ^c , ALK, ALK', and n as previously defined for (IVb). Preferably ALK and ALK' are identical and represent a (C ₁ -C ₄ )alkylene group such as propylene R ^c and R' ^c are identical and represent an amino(C ₁ -C ₄ )alkyl group such as aminoethyl
particular mention may be made of Dimethoxysilyl Ethylenediaminopropyl Dimethicone (RN: 71750-80-6), under the trade name GP-RA-157, marketed by Genesee Polymers.

(IVc)
Formula (IVc) in which R ^a , R ^b , and R ^d , which are identical or different, preferably identical, represent a (C ₁ -C ₄ )alkyl group such as methyl, (C ₁ -C ₄ )alkoxy such as methoxy , aryl such as phenyl, aryloxy such as phenoxy, aryl(C ₁ -C ₄ )alkyl such as benzyl, or aryl(C ₁ -C ₄ )alkoxy such as benzoxy, preferably (C ₁ -C ₄ )alkyl such as methyl, R ^d may also represent a (C ₁ -C ₆ )alkyl group substituted by a (C ₁ -C ₄ )alkylamino or amino group, R ^c represents a hydrogen atom or a (C ₁ -C ₄ ) group alkyl, preferably hydrogen atom; ALK represents a (C ₁ -C ₆ )alkylene group, preferably (C ₁ -C ₄ )alkylene such as propylene; n and m, identical or different, representing an integer greater than 2 and more particularly the values of m and n are such that the weight-average molecular weight of the silicone is between 1,000 and 55,000;

Preferably, the polydi(C ₁ -C ₄ )alkylsiloxanes of formula (IVc) are of the following formula (IV'c):

(IV'c)
formula (IV'c), in which the values of n and m are such that the weight-average molecular weight of the silcone is between 1000 and 55,000. As examples of silicone (IVc), mention may be made of those sold under the names “AMS-132”, “AMS-152”, “AMS-162”, “AMS-163”, “AMS-191”, “AMS-1203” by the company GELEST;

(IVd)
Formula (IVd) in which R ^a , and R ^b , which are identical or different, preferably identical, represent a (C ₁ -C ₄ )alkyl group such as methyl, (C ₁ -C ₄ )alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(C ₁ -C ₄ )alkyl such as benzyl, or aryl(C ₁ -C ₄ )alkoxy such as benzoxy, preferably (C ₁ -C ₄ )alkyl such as methyl, and R ^d represents a (C ₁ -C ₆ )alkyl group optionally substituted by a (C ₁ -C ₄ )alkylamino or amino group, preferably (C ₁ -C ₄ )alkyl, such as isobutyl, terbutyl or n -butyl , R ^c represents a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom; ALK represents a (C ₁ -C ₆ )alkylene group, preferably (C ₁ -C ₄ )alkylene such as propylene; n representing an integer greater than 2 and more particularly the value of n is such that the weight-average molecular weight of the silicone is between 500 and 5000;

Preferably, the polydi(C ₁ -C ₄ )alkylsiloxanes of formula (IVd) are of the following formula (IV'd):

(IV’d)
formula (IV'd), in which the value of n is such that the weight-average molecular weight of the silicone is between 500 and 3000. As an example of silicone (IVd), mention may be made of those sold under the names "MCR -A11”, “MCR-A12” by the company GELEST;
- amodimethicones of formula (IVe):

(IV)
Formula (IVe) in which:
- R ^a , and R ^b , identical or different, preferably identical, represent a group (C ₁ -C ₄ )alkyl such as methyl, (C ₁ -C ₄ )alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(C ₁ -C ₄ )alkyl such as benzyl, or aryl(C ₁ -C ₄ )alkoxy such as benzoxy, preferably (C ₁ -C ₄ )alkyl such as methyl,
- R ^c represents a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom;
- R ^e represent a hydroxy, (C ₁ -C ₄ )alkoxy, amino, (C ₁ -C ₄ )alkylamino group,
- R ^f , represents a (C ₁ -C ₄ )alkyl group such as methyl, (C ₁ -C ₄ )alkoxy such as methoxy, a hydroxy group or -O–(SiR ₂ ) _x -R' with R representing a (C ₁ -C ₄ )alkyl or (C ₁ -C ₄ )alkoxy group and R' representing a (C ₁ -C ₄ )alkoxy or hydroxy group, preferably R ^f represents a (C ₁ -C ₄ )alkyl group , (C1-C4)alkoxy, or -O–(SiR ₂ ) _x -R' with R representing a (C ₁ -C ₄ )alkyl group such as methyl and R' a hydroxy or (C ₁ -C ₄ ) group alkoxy such as methoxy;
- R ^g represents a hydrogen atom, a (C ₁ -C ₆ )alkyl group
- ALK and ALK', which are identical or different, represent a (C ₁ -C ₆ )alkylene group, preferably (C ₁ -C ₄ )alkylene such as ethylene or propylene; n and m, identical or different, representing an integer greater than 2, p and x are integers greater than or equal to 0, preferably p is between 2 and 20 and more particularly the values of m, n, p and x are such that the weight-average molecular weight of the silicone is between 2,000 and 700,000, preferably between 5,000 and 500,000;

Preferably, the amodimethicones of formula (IVe) are of the following formula (IV'e):

(IV)
Formula (IV'e) in which:
- ALK represents a (C ₁ -C ₆ )alkylene group, preferably ethylene,
- ALK' represents a (C ₁ -C ₆ )alkylene group, preferably propylene, and
- m, n and p represent greater than 2, with m and n and p being such that the weight-average molecular mass of the compound is between 5,000 and 500,000 approximately; preferably p represents an integer between 8 and 20;

according to another preferred embodiment, the amodimethicones of formula (IVe) are chosen from that of formula:

(IV''e)
Formula (IV''e) in which
- R ^a , and R ^b , identical or different, preferably identical, represent a group (C ₁ -C ₄ )alkyl such as methyl, (C ₁ -C ₄ )alkoxy such as methoxy, preferably (C ₁ -C ₄ ) alkyl such as methyl,
- R ^c represents a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom;
- R ^g represent a hydrogen atom, or a (C ₁ -C ₄ )alkyl group;
- R ^f , represents a (C ₁ -C ₄ )alkyl group such as methyl, (C ₁ -C ₄ )alkoxy such as methoxy, or -O–(SiR ₂ ) _x -R' with R representing a (C ₁ -C ₄ )alkyl such as methyl and R' a hydroxy or (C ₁ -C ₄ )alkoxy group such as methoxy;
- R ^g represents a hydrogen atom, a (C ₁ -C ₆ )alkyl group,
- ALK represents a (C ₁ -C ₆ )alkylene group, preferably ethylene,
- ALK' represents a (C ₁ -C ₆ )alkylene group, preferably propylene,
- n and m, identical or different, representing an integer greater than 2, x is an integer greater than or equal to 0, preferably the values of m, n, and x are such that the weight-average molecular weight of the silicone is between 2,000 and 700,000, preferably between 5,000 and 500,000;

Even more particularly (IV’’e) represents:

Formula (IV''e) in which R ^f , R ^g , ALK, ALK', m, n as defined for (IV''e). The amodimethicone and trimethylsiloxyamodimethicone belonging to the formula (IV''e) and the formula above are, for example, the amodimethicone and trimethylsiloxyamodimethicone of the ADM type sold by the company Wacker-Belsil®, mention may also be made of POLYDIMETHYLSILOXANE WITH AMINOETHYLAMINOPROPYL GROUPS, WITH METHOXY AND/OR HYDROXY AND ALPHA-OMEGA SILANOLS FUNCTION IN AQ CATIONIC EMULSION AT 60% (Supplier reference: XIAMETER MEM-8299 EMULSION for DOW CORNING or Supplier reference: BELSIL ADM 4000 E for WACKER); POLY DIMETHYLSILOXANE WITH AMINOETHYL IMINOPROPYL GROUP IN 15% PRESERVED NON-IONIC MICROEMULSION (Supplier reference: BELSIL ADM LOG 1);
- Polyether amines, in particular known under the reference JEFFAMINE from the company HUNSTMAN; and in particular: Polyethylene glycol and/or polypropylene glycol α, ω-diamine (with amine function at the end of the chain) such as those sold under the names JEFFAMINE D-230, D-400, D-2000, D-4000, ED-600, ED-9000, ED-2003.
- Polytetrahydrofuran (or polytetramethylene glycol) α, ω-diamine, polybutadienes α, ω-diamine;
- Polyamidoamine (PANAM) dendrimers with terminal amine functions;
- Poly(meth)acrylates or poly(meth)acrylamides carrying lateral primary or secondary amine functions such as poly(3-aminopropyl)methacrylamide, poly(2-aminoethyl) methacrylate.

As polyamino compounds having several primary amine groups and/or secondary amine amino polymer e), polydi(C ₁ -C ₄ )alkylsiloxanes comprising primary amine groups at the end of the chain or on the side chains are preferably used.

Advantageously, the polyamino compounds e) used in the process according to the invention are chosen from polydi(C ₁ -C ₄ )alkylsiloxanes comprising primary amine groups at the end of the chain and/or on the side chains.

Preferably, the amino compound(s) iv) is (are) chosen from polysaccharide(s) containing amine group(s) as well as their organic or mineral acid salts, their α or β, their optical isomers of L or D configuration and their solvates such as hydrates.

According to a preferred embodiment of the invention, the polysaccharide(s) containing amine group(s) has(have) an average molecular weight MW less than or equal to 400 KDa, particularly less than 200 KDa. According to a particular embodiment, the polysaccharide(s) containing amine group(s) have a low average molecular weight MW, ie have a MW <100 KDa, preferentially have an average MW which is <40 KDa, more preferentially have an average MW which is comprised inclusively between 1 KDa and 30 KDa, even more preferentially have an average PM which is comprised inclusively between 3 KDa and 28 KDa.

The polysaccharide(s) with amine group(s) of the invention is (are) of natural animal or plant origin, or else be derived from synthesis, hemisynthesis or biosynthesis.

According to a particular embodiment of the invention, the polysaccharide(s) containing amine group(s) is (are) chosen from those containing C ₅ -C ₇ sugar units, as well as their salts. of organic or mineral acid, their α or β anomers, their optical isomers of L or D configuration and their solvates such as hydrates.

More particularly, the polysaccharide(s) with amine group(s) of the invention is(are) with a C ₆ sugar unit with amine group(s), these polysaccharides with amine group(s) (s) are then called polyhexosamines.

According to a particular embodiment, the sugar units of the polysaccharide with amine group(s) of the invention are of β (beta) anomeric configuration and/or of D configuration.

According to a particular embodiment, the osidic units of the polysaccharide with amine group(s) b) are interconnected between the atoms of carbon 1 of one osidic unit and carbon 4 of the other osidic unit, denoted ( 1 → 4), such as the polysaccharide with amine group(s) of formula (B) below, as well as their organic or mineral acid salts, their α or β anomers, their optical isomers of L or D configuration and their solvates such as hydrates:

(B)

Formula (B) in which:

- R radicals_at, R_b, R_vsof each osidic unit can be identical or different;
-notis an integer greater than or equal to 2, particularly comprised inclusively between 3 and 3000, more particularly between 5 and 2500, preferentially between 10 and 2300;
-R _at ,R _b , andR _vs , identical or different, represent i) hydroxy, ii) (C₁-VS₄)alkoxy, the alkyl group of which may be optionally substituted, in particular by one or more hydroxy, iii) carboxy, and iv) NR groups₁R₂with R₁and R₂as previously defined, in particular R₁and R₂are chosen from the hydrogen atom and –C(O)-R’₁in which R'₁is as defined previously; preferably R₁and R₂represent i) hydrogen atom or ii) –C(O)-R’₁and R'₁representing a group (C₁-VS₄) alkyl such as methyl;
it being understood that at least one of the radicals R_at, R_bor R_vsof at least one carbohydrate unit represents an NR group₁R₂and that at least one of the NR groups₁R₂of at least one saccharide unit represents a NH group₂; preferablyR _at of at least one sugar unit represents an NR group₁R₂with R₁which represents a hydrogen atom and R₂is selected from i) a hydrogen atom or ii) a –C(O)-R’ group₁, andR _b andR _vs , represent a hydroxy group, it being understood that at least one of the NR groups₁R₂of at least one saccharide unit represents a NH group_{2 .}

More particularly, the polysaccharide(s) containing amine group(s) of the invention is (are) of the following formula (B ₁ ) , as well as their organic or mineral acid salts, their α or β anomers , their optical isomers of L or D configuration and their solvates such as hydrates:

(B ₁ )

Formula (B1) in which:

- R' represents a hydrogen atom or a (C ₁ -C ₄ )alkylcarbonyl group such as acetyl CH ₃ -C(O)-;
- R'' represents a hydrogen atom or a (C ₁ -C ₄ )alkyl group optionally substituted by a carboxy group such as –CH(CO ₂ H)-CH ₃ ;
- n is an integer greater than or equal to 2, particularly comprised inclusively between 3 and 3000, more particularly between 5 and 2500, preferentially between 10 and 2300;
it being understood that in the polysaccharide ( B ₁ ) at least one osidic unit carries an amino group NH ₂ and at least one other osidic unit carries at least one N(H)-R' group with R' representing a group (C ₁ - C ₄ )alkylcarbonyl such as acetyl CH ₃ -C(O)-.

Preferably, the sugar units of formula (B) or (B ₁ ) are of D configuration or also called D-glucopyrane. In particular, the units of formula (B) or (B ₁ ) are of β (beta) anomeric configuration. According to a particular embodiment, the polysaccharides of the invention are chosen from the compounds of formula (B ₂ ) below as well as their acid, organic or mineral salts, and their solvates such as hydrates:

(B ₂ )

Formula (B2) in which:

-R _at ,R _b , andR _vs , are as defined for(B)previously; and.
- R radicals_at, R_b, R_vsof each osidic unit can be identical or different;
- notis an integer greater than or equal to 2, particularly comprised inclusively between 3 and 3000, more particularly between 5 and 2500, preferentially between 10 and 2300;
it being understood that in the polysaccharide (B ₂ ) at least one of the radicals R_at, R_bor R_vsof at least one carbohydrate unit represents an NR group₁R₂and that at least one of the NR groups₁R₂of at least one saccharide unit represents a NH group₂; preferably at least one osidic unit bears an R group_atamino NH₂and at least one other sugar unit bears an R group_atwhich represents -N(H)-R’ with R’ representing a group (C₁-VS₄)alkylcarbonyl such as acetyl CH₃-CO)-.

Preferably, the polysaccharide(s) containing amine group(s) of the invention is (are) chosen from chitin and chitosan and their derivatives, preferably chitosan.

More particularly, the polysaccharide(s) containing amine group(s) of the invention is (are) chosen from those of the following formula (B ₃ ) as well as their salts of organic or mineral acids, and their solvates such as hydrates,

(B ₃ )

Formula (B3) in which,

- R ₁ and R ₂ are as defined in formulas (B), (B ₁ ) or (B ₂ ); and
- n is an integer greater than or equal to 2, particularly comprised inclusively between 3 and 3000, more particularly between 5 and 2500, preferentially between 10 and 2300;
it being understood that in the polysaccharide b) of formula ( B ₃ ) at least one osidic unit bears an amino group NH ₂ .

In particular, the polysaccharide(s) containing amine group(s) of the invention is (are) chosen from chitosans, salified with organic acid, preferably with the aid of carboxylic acid, in particular (C ₁ -C ₆ )alkylcarboxylic acid such as acetic acid.

More preferably, the amino compound(s) iv) comprised in composition (B) of the process of the invention is (are) chosen from those of formulas (IVb) and (IVe) as defined previously and even more preferentially (IV′b) and (IV′e) as defined previously.

According to a particular embodiment of the invention, composition (B) also comprises one or more hydrocarbon-based oils iii) as defined above. Advantageously, the hydrocarbon oils contained in the dispersion (A) and the composition (B) are identical.

According to a preferred embodiment of the invention, the hydrocarbon-based oil or oils of composition (B) are chosen from hydrocarbon-based oils having from 8 to 14 carbon atoms, in particular the apolar oils, described above. Even more preferentially, the hydrocarbon oil or oils of composition (B) are isododecane.

According to a particular embodiment of the invention, composition (B) is aqueous or aqueous-alcoholic, preferably aqueous. By hydroalcoholic is meant a mixture of water and C ₂ -C ₄ alkanol, linear or branched, preferably water and ethanol.

According to an advantageous embodiment of the invention, composition (B) is aqueous or aqueous-alcoholic and preferably also comprises one or more polysaccharides containing amine groups, preferably chitosan, and/or one or more polyamino acids, preferably polylysines, more preferably chitosan.

According to another advantageous embodiment of the invention, composition (B) is aqueous and comprises one or more alkoxysilane f) as defined above in emulsion in water, in particular of the oil-in-water (W/O) or "water in oil (W/O)”.

According to yet another advantageous embodiment of the invention, composition (B) is aqueous and comprises one or more polyamines e) as defined previously in oil-in-water (O/W) or “oil in water (O/W) type emulsion )”.

Advantageously, the amino compound(s) used in the process according to the invention are implemented according to an amino group molar ratio of the amino compound iv) / of anhydride compound with ethylenic unsaturation anhydride b) as defined previously ranging from 0.01 to 10, preferably ranging from 0.1 to 5, preferably ranging from 0.1 to 2, and more preferably ranging from 0.1 to 1.

The at least two-step process of the invention makes it possible to obtain deposits of cosmetic agents and in particular of pigments having good resistance to external attacks that keratin materials can undergo, in particular good resistance to soap and water, shower gel, and cooking oils.

In addition, the method of the invention makes it possible to trap non-volatile compounds, in particular oils, for example to improve the cosmetics, or to provide shine to keratin materials, preferably the skin, in particular the skin of the face such as the lips and this in a remanent way vis-à-vis external aggressions.

As non-volatile oils, mention may be made of: hydrocarbon-based oils of animal origin such as perhydrosqualene; vegetable hydrocarbon oils such as liquid triglycerides of fatty acids with 4 to 10 carbon atoms such as triglycerides of heptanoic or octanoic acids, or else sunflower, corn, soybean, grapeseed, sesame, apricot, macadamia, castor, avocado, caprylic/capric acid triglycerides, jojoba oil, shea butter; linear or branched hydrocarbons, of mineral or synthetic origin such as paraffin oils and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as parleam; synthetic esters and ethers, in particular of fatty acids such as, for example, Purcellin's oil, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dodecyl stearate, erucate octyl-2-dodecyl, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearylmalate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters such as propylene glycol dioctanoate, neopentylglycol diheptanoate, diethyleneglycol diisononanoate; and pentaerythritol esters; fatty alcohols having 12 to 26 carbon atoms such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol; partially hydrocarbon and/or silicone fluorinated oils; silicone oils such as volatile or non-volatile, linear or cyclic polymethylsiloxanes (PDMS), liquid or pasty at room temperature such as cyclomethicones, dimethicones, optionally comprising a phenyl group, such as phenyl trimethicones, phenyltrimethylsiloxydiphenyl siloxanes, diphenylmethyldimethyl-trisiloxanes, diphenyl dimethicones, phenyl dimethicones, polymethylphenyl siloxanes; their mixtures.

These oils may be present in a content ranging from 0.01 to 60%, and better still from 0.1 to 50% by weight, relative to the total weight of the dispersion (A).

Dispersion (A) and compositions (B) and (C) according to the invention may also comprise one or more dyestuffs chosen from fat-soluble dyes, and pulverulent dyestuffs such as pigments, nacres, and well-known flakes. known to those skilled in the art. The dyestuffs may be present, in the composition, in a content ranging from 0% to 30% by weight, relative to the weight of the dispersion or composition which comprises them, preferably from 0% to 10% by weight.

The dispersion (A) and the compositions (B) and (C) according to the invention may also comprise one or more fillers, in particular in a content ranging from 0.01% to 30% by weight, relative to the weight of the dispersion or composition which includes them.

the plasticizer(s)

By " plasticizer " or " plasticizing agent " is meant an organic chemical compound, which is in the solid state or in the liquid state, at room temperature and at atmospheric pressure, and which is added to a composition comprising different types of polymerizable ingredients (monomers), to make the polymer softer, more flexible, and/or improve its mechanical strength. Plasticizers are known to those skilled in the art, mention may be made, for example, of “Plasticizers”, Encyclopedia of polymer Science and Technology , Helmut Reinecke, Rodrigo Navarro, Mónica Pérez, https://doi.org/10.1002/0471440264.pst245. pub215 September 2011.

The plasticizers within the meaning of the invention have a molecular weight of between 200 and 1000 g/mol, particularly between 300 and 700, preferably between 350 and 600. The agents are also organic compounds consisting of carbon atoms , hydrogen, and one or more heteroatoms chosen from oxygen, sulfur and silicon atoms, in particular chosen from oxygen and silicon atoms, preferably at least 3 heteroatoms even more preferably between 4 and 10 heteroatoms, and may have one or more aryl groups such as benzyl. In particular, they comprise one or more groups chosen from esters, phthalates, benzoates, sulphonates, citrates and siloxanes.

Preferably, the plasticizer(s) of the invention are chosen from those of the families of phthalates, esters, citrates, benzoates, citrates and siloxanes.

According to a particular embodiment of the invention, the plasticizer(s) are chosen from the compounds (V) and (VI) below:

(V)

Formula (V) in which:

- R ^h , and R ⁱ , which are identical or different, represent a group (C ₁ -C ₂₀ )alkyl, aryl such as phenyl, aryl (C ₁ -C ₄ )alkyl such as benzyl, preferably (C ₁ -C ₄ ) alkyl such as n -butyl;

- n is 1, 2 or 3, preferably 2; and

- L represents a group a) C ₁ -C ₁₀ alkyl, di, tri or tetravalent, preferably (C ₂ -C ₈ ) trivalent alkyl, said di, tri or tetravalent alkyl, possibly being substituted by one or more groups hydroxy, b) di, or trivalent cycloalkyl, or c) di, tri or tetravalent aryl, preferably di, or trivalent phenyl, preferably L represents a group a);

(VI)

Formula (VI) in which:

-R ^I , identical or different, preferably identical, represents a group (C₁-VS₁₀)alkyl, aryl such as phenyl, aryl(C₁-VS₄)alkyl such as benzyl, preferably aryl such as phenyl,
-R ^I identical or different, preferably identical represents a hydrogen atom, or a hydroxy group, (C₁-VS₆)alkyl, or (C₁-VS₆)alkoxy,
- L'represents a group selected from a) C-alkyl₂-VS₁₀, divalent, preferably (C₄-VS₈)divalent alkyl, which may be optionally substituted by one or more hydroxy groups, and/or interrupted by one or more oxygen atoms, and/or interrupted by one or more divalent groups -Si(R^I)(R^k)- with R^Iand R^kas previously defined, b) di, or trivalent cycloalkyl, c) di, tri or tetravalent aryl, and d) -Si(R^I)(R^k)-, preferably L' represents a group d) -Si(R^I)(R^k)-.

According to a particular embodiment of the invention, the compounds of formula (V) are chosen from the compounds of formula (V') :

(V')

Formula (V) in which:

- R ^h , and R ⁱ , which are identical or different, represent a group (C ₁ -C ₆ )alkyl, aryl (C ₁ -C ₄ )alkyl such as benzyl, preferably (C ₁ -C ₄ )alkyl such as n - butyl;

- n is 1, or 2, preferably 2; and

- L represents a group a) C ₂ -C ₆ alkyl, di, tri or tetravalent, preferably (C ₂ -C ₈ )trivalent alkyl, said alkyl possibly being substituted by one or more hydroxy groups, preferably substituted by a hydroxy group.

According to a particular embodiment of the invention, the compounds of formula (VI) are chosen from the compounds of formula (VI') :

(VI')

Formula (VI') in which:

-R ^I , identical or different, preferably identical, represents an aryl group such as phenyl, aryl(C₁-VS₄)alkyl such as benzyl, preferably aryl such as phenyl, and
-R ^I identical or different, preferably identical, represents a group represents (C₁-VS₆)alkyl, preferably (C₁-VS₄)alkyl such as methyl.

In particular, the plasticizer(s) of the invention are chosen from: di n -hexyl phthalate (DnHP), diisoheptyl phthalate (DIHP), diheptyl phthalate (DnHP), di(2-ethylhexyl) phthalate (DEHP), diheptylnonyl phthalate (DnHNP ), di n -octyldecylphthalate (DNODP), diheptylnonylundecylphthalate (DnHNUP), diisononyl phthalate (DINP), dinonyl phthalate (DNP), di n -nonyl phthalate (DnNP) diisodecyl phthalate (DIDP), di n -nonyldecylundecyl phthalate (DnNDUP), dinonylundecyl phthalate (DnNUP), diundecyl phthalate (DUP), diisoundecyldodecylphthalate (UDP), ditridecyl phthalate (DTDP), di(2-ethylhexyl)teraphthalate (DOTP), butylbenzyl phthalate (BBP), diheptylnonyl adipate (DnHNA), di(2- ethylhexyl) adipate (DEHA), diisononyl adipate (DINA), diisodecyl adipate (DIDA), triheptylnonyl trimellitate (TnHNTM), tri(2-ethylhexyl)trimellitate (TOTM), triisononyl trimellitate (TINTM), di(2-ethylhexyl) sebacate ( DOS), di(2-ethylhexyl) azelate (DOZ), tributyl citrate and trimethylpentaphenyltrisiloxane , preferably the plasticizer(s) of the invention are chosen from: tri(C ₁ -C ₆ )alkylcitrates such as tributyl citrate and trimethylpentaphenyltrisiloxane.

The plasticizer(s) v) of the invention may be present in composition (A), and/or in composition (B), and/or in another composition (C). Preferably, the plasticizer(s) of the invention are present in composition (A).

According to a particular embodiment of the invention, the plasticizer(s) is present in an amount of between 5 and 50% by weight, relative to the total weight of the polymer(s) a) to d) of the particles.

According to a particular embodiment of the invention of the invention, the plasticizer(s) is present in an amount of between 0.5 and 30% by weight, in particular between 1 and 20%, preferably from 1.5 to 10 % by weight relative to the total weight of composition (A), and/or in composition (B), and/or in another composition (C), preferably relative to the total weight of composition (A).

the cosmetic active ingredient(s) vi)

The cosmetic active ingredient(s) of the invention is (are) chosen from a) pigments, b) active ingredients for caring for keratin materials, preferably the skin, and c) UV filters as well and d) their mixtures.

According to a preferred embodiment of the present patent application, the cosmetic active ingredient(s) vi) of the invention is (are) chosen from a) dyes and/or pigments.

According to a particular embodiment of the present patent application, the cosmetic active ingredient(s) vi) of the invention is (are) chosen from b) active ingredients for the care of keratin materials, preferably skin care actives.

According to yet another particular embodiment of the present patent application, the cosmetic active ingredient(s) vi) of the invention is (are) chosen from c) UV filters.

According to a particular embodiment of the invention, the dispersion (A) and/or the composition (B) and/or the composition (C) of the invention comprise vi) one or more cosmetic active ingredient(s).

According to a particular embodiment of the invention, the dispersion (A) comprises vi) one or more cosmetic active agents, preferably one or more pigment(s).

According to another particular embodiment of the invention, composition (B) comprises vi) one or more cosmetic active agents, preferably one or more pigment(s).

According to a preferred embodiment of the invention, composition (C) comprises vi) one or more cosmetic active agents, preferably one or more pigment(s).

The hair dye(s) represent more particularly from 0.001 to 10% by weight of the total weight of the composition which comprises them, and preferably from 0.005 to 5% by weight.

According to a particular embodiment of the invention, the dispersion (A) and/or the composition (B) and/or the composition (C) of the invention comprise vi) one or more hair dye(s) and /or pigment(s).

According to a particular embodiment of the invention, the dispersion (A) comprises vi) one or more hair dye(s).

According to another particular embodiment of the invention, composition (B) comprises vi) one or more hair dye(s).

According to a preferred embodiment of the invention, composition (C) comprises vi) one or more hair dye(s).

By “ hair dyes ” is meant oxidation dyes, direct dyes and direct dyes used to color keratin fibres, in particular human fibres, such as the hair.

Among the hair dyes we can mention:
- oxidation dyes which are generally chosen from one or more oxidation bases, optionally combined with one or more coupling agents.
By way of example, the oxidation bases are chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases and the corresponding addition salts optionally combined with coupling agents, it is in particular chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based coupling agents and heterocyclic coupling agents as well as the corresponding addition salts.
- direct dyes, in particular azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures. Direct dyes can be anionic, cationic or neutral.
- natural dyes chosen in particular from hennotannic acid, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogalline, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orcein as well as extracts or decoctions containing these natural dyes.

The hair dye(s) represent more particularly from 0.001 to 10% by weight of the total weight of the composition which comprises them, and preferably from 0.005 to 5% by weight.

According to a particular embodiment of the invention, the dispersion (A) comprises vi) one or more cosmetic active ingredient(s), in particular one or more pigment(s).

According to another particular embodiment of the invention, composition (B) comprises vi) one or more cosmetic active ingredient(s), in particular one or more pigment(s).

According to yet another preferred embodiment of the invention, composition (C) comprises vi) one or more cosmetic active ingredient(s), in particular one or more pigment(s).

By “ pigment ”, is meant all the pigments providing color to keratin materials, of synthetic or natural origin. The solubility of the pigments in water at 25° C. and at atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01%.

These are solid, white or colored particles, naturally insoluble in the liquid hydrophilic and lipophilic phases usually used in cosmetics or rendered insoluble by formulation in the form of a lacquer, where appropriate. More particularly pigments with little or no solubility in hydro-alcoholic media.

The pigments which can be used are in particular chosen from the organic and/or inorganic pigments known in the art, in particular those which are described in the encyclopedia of chemical technology by Kirk-Othmer and in the encyclopedia of industrial chemistry by Ullmann. Mention may in particular be made, as pigments, of organic and inorganic pigments such as those defined and described in Ullmann's Encyclopedia of Industrial Chemistry "Pigment organics", 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a20 371 and ibid, "Pigments, Inorganic, 1. General” 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim10.1002/14356007.a20_243.pub3

These pigments can be in the form of powder or pigment paste. They can be coated or uncoated.

The pigments can for example be chosen from mineral pigments, organic pigments, lakes, special effect pigments such as nacres or glitter, and mixtures thereof.

The pigment can be an inorganic pigment. By mineral pigment, we mean any pigment that meets the definition of the Ullmann encyclopedia in the chapter inorganic pigment. Mention may be made, among the mineral pigments useful in the present invention, of iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.

The pigment may be an organic pigment. By organic pigment, we mean any pigment that meets the definition of the Ullmann encyclopedia in the organic pigment chapter. The organic pigment can in particular be chosen from nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane, quinophthalone compounds.

In particular, the white or colored organic pigments can be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Color Index under Cl references 42090, 69800, 69825, 73000, 74100, 74160, yellow pigments codified in the Color Index under Cl references 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, green pigments codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120 12370, 12420, 12490, 14700, 15525, 15580, 15800, 15850, 15865, 15880, 17200, 45, 4580, 458, 73915, 73360, 73915, 73360, 73915, 73360, 73915, 75470, the pigments obtained by oxidizing polymerization of indolic derivatives , phenolic as described in patent FR 2,679,771.

According to a particular embodiment of the invention, pigment pastes of organic pigments such as the products sold by the company HOECHST under the name:
- YELLOW COSMENYL IOG: Pigment YELLOW 3 (Cl 11710);
- COSMENYL G YELLOW: Pigment YELLOW 1 (Cl 11680);
- ORANGE COSMENYL GR: Pigment ORANGE 43 (Cl 71105);
- COSMENYL RED R: Pigment RED 4 (Cl 12085);
- CARMIN COSMENYL FB: Pigment RED 5 (Cl 12490);
- VIOLET COSMENYL RL: Pigment VIOLET 23 (Cl 51319);
- COSMENYL BLUE A2R: Pigment BLUE 15.1 (Cl 74160);
- GREEN COSMENYL GG: Pigment GREEN 7 (Cl 74260);
- COSMENYL BLACK R: Pigment BLACK 7 (Cl 77266).

The pigments in accordance with the invention may also be in the form of composite pigments as described in patent EP 1 184 426. These composite pigments may be composed in particular of particles comprising:
- an inorganic core,
- at least one binder ensuring the fixing of the organic pigments on the core, and
- at least one organic pigment at least partially covering the core.

The term " lacquer " means the dyes adsorbed on insoluble particles, the assembly thus obtained remaining insoluble during use. The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum. Among the organic dyes, mention may be made of cochineal carmine.

Examples of lacquers include the products known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410 ), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 7 (CI 15 850:1), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985), D & C Green (CI 61 570), D & C Yellow 1 O (CI 77 002), D&C Green 3 (CI 42053), D&C Blue 1 (CI 42090).

The inorganic substrates on which the dyes are adsorbed are for example alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.

Among the dyes, mention may be made of cochineal carmine. Mention may also be made of the dyes known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985), D & C Green (CI 61 570), D & C Yellow 1 O (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 ( CI 42 090).

As examples of lacquers, mention may be made of the product known under the following name: D & C Red 7 (CI 15 850:1).

The pigment or pigments can also be special effect pigments.

By " special effect pigments " is meant pigments which generally create a colored appearance (characterized by a certain shade, a certain vividness and a certain clarity) which is not uniform and changes according to the conditions of observation (light , temperature, viewing angles, etc.). They are thereby opposed to colored pigments which provide a uniform opaque, semi-transparent or transparent classic tint.

There are several types of special effect pigments, those with a low refractive index such as fluorescent, photochromic or thermochromic pigments, and those with a higher refractive index such as pearlescent or glitter.

Examples of special effect pigments include pearlescent pigments such as titanium mica covered with an iron oxide, mica covered with an iron oxide, mica covered with bismuth oxychloride, titanium mica covered with chromium oxide, titanium mica covered with an organic dye, in particular of the aforementioned type, as well as pearlescent pigments based on bismuth oxychloride . They may also be particles of mica on the surface of which are superimposed at least two successive layers of metal oxides and/or of organic coloring matter.

The nacres may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or copper color or sheen.

By way of illustration of the nacres that can be used in the context of the present invention, mention may be made in particular of the gold-colored nacres marketed in particular by the company ENGELHARD under the name Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); mother-of-pearl bronzes sold in particular by the company MERCK under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona), by the company Eckart under the name Prestige Bronze and by the company ENGELHARD under the name Super bronze (Cloisonne ); the orange nacres sold in particular by the company ENGELHARD under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company MERCK under the name Passion orange (Colorona) and Matte orange (17449) (Microna); brown mother-of-pearl in particular marketed by the company ENGELHARD under the name Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); mother-of-pearl with a copper sheen sold in particular by the company ENGELHARD under the name Copper 340A (Timica) and by the company Eckart under the name Prestige Copper; nacres with a red sheen in particular marketed by the company MERCK under the name Sienna fine (17386) (Colorona); nacres with a yellow sheen in particular marketed by the company ENGELHARD under the name Yellow (4502) (Chromalite); nacres of red tint with a gold sheen in particular marketed by the company ENGELHARD under the name Sunstone G012 (Gemtone); black mother-of-pearl with a gold sheen, in particular marketed by the company ENGELHARD under the name Nu antique bronze 240 AB (Timica), blue mother-of-pearl, in particular marketed by the company MERCK under the name Matte blue (17433) (Microna), Dark Blue (117324) (Colorona), white nacres with a silver sheen in particular marketed by the company MERCK under the name Xirona Silver and pinkish orange-golden nacres in particular marketed by the company MERCK under the name Indian summer (Xirona) and mixtures thereof.

In addition to nacres on a mica support, one can consider multilayer pigments based on synthetic substrates such as alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.

Mention may also be made of pigments with an interference effect not fixed on a substrate, such as liquid crystals (Helicones HC from Wacker), holographic interference flakes (Geometric Pigments or Spectra f/x from Spectratek). Special effect pigments also include fluorescent pigments, whether fluorescent in daylight or which produce ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, marketed for example by the Quantum Dots Corporation.

The variety of pigments which can be used in the present invention makes it possible to obtain a rich palette of colors, as well as particular optical effects such as metallic and interference effects.

The size of the pigment used in the cosmetic composition according to the present invention is generally between 10 nm and 200 μm, preferably between 20 nm and 80 μm, and more preferably between 30 nm and 50 μm.

The pigments can be dispersed in the product thanks to a dispersing agent.

By “ dispersing agent ” is meant a compound which makes it possible to protect the dispersed particles against their agglomeration or flocculation. This dispersing agent can be a surfactant, an oligomer, a polymer or a mixture of several of them, bearing one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they can cling physically or chemically to the surface of the pigments. These dispersing agents also have at least one functional group that is compatible or soluble in the continuous medium. Said agent can be charged, it can be anionic, cationic, zwitterionic or neutral.

According to a particular embodiment of the invention, the dispersing agents used are chosen from esters of 12-hydroxystearic acid, more particularly of C ₈ to C ₂₀ fatty acids, and of polyol such as glycerol, diglycerin, such as poly(12-hydroxystearic) acid stearate with a molecular weight of approximately 750 g/mole such as that sold under the name Solsperse 21,000 by the company Avecia, polygyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel or alternatively polyhydroxystearic acid such as that sold under the reference Arlacel P100 by the company Uniqema and their mixtures.

As other dispersant that can be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17000 sold by the company Avecia, mixtures of polydimethylsiloxane/oxypropylene such as those sold by the company Dow Corning under the references DC2-5185, DC2-5225 C.

The pigments used in the cosmetic composition according to the invention can be surface-treated with an organic agent.

Thus the pigments previously surface-treated useful in the context of the invention are pigments which have undergone totally or partially a surface treatment of a chemical, electronic, electro-chemical, mechano-chemical or mechanical nature, with an organic agent such as those which are described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, p. 53-64 before being dispersed in the composition in accordance with the invention. These organic agents can for example be chosen from amino acids; waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminum salts of fatty acids, for example aluminum stearate or laurate; metal alkoxides; polysaccharides, for example chitosan, cellulose and its derivatives; polyethylene; (meth)acrylic polymers, for example polymethylmethacrylates; polymers and copolymers containing acrylate units; the proteins ; alkanoamines; silicone compounds, for example silicones, polydimethylsiloxanes, alkoxysilanes, alkylsilanes, siloxysilicates; fluorinated organic compounds, for example perfluoroalkyl ethers; fluoro-silicone compounds.

The surface-treated pigments useful in the cosmetic composition according to the invention may also have been treated with a mixture of these compounds and/or have undergone several surface treatments.

The surface-treated pigments useful in the context of the present invention can be prepared according to surface treatment techniques well known to those skilled in the art or found as such in commerce.

Preferably, the surface-treated pigments are covered by an organic layer.

The organic agent with which the pigments are treated can be deposited on the pigments by solvent evaporation, chemical reaction between the molecules of the surfactant or creation of a covalent bond between the surfactant and the pigments. Surface treatment can thus be carried out, for example, by chemical reaction of a surfactant with the surface of the pigments and creation of a covalent bond between the surfactant and the pigments or the fillers. This method is described in particular in US patent 4,578,266.

Preferably, an organic agent bound to the pigments covalently will be used.

The surface treatment agent can represent from 0.1 to 50% by weight of the total weight of the surface-treated pigments, preferably from 0.5 to 30% by weight, and even more preferably from 1 to 10% by weight.

Preferably, the surface treatments of the pigments are chosen from the following treatments:
- a PEG-Silicone treatment such as the AQ surface treatment marketed by LCW;
- a Chitosan treatment such as the CTS surface treatment marketed by LCW;
- a Triethoxycaprylylsilane treatment such as the AS surface treatment marketed by LCW;
- a Methicone treatment such as the SI surface treatment marketed by LCW;
- a Dimethicone treatment such as the Covasil 3.05 surface treatment marketed by LCW;
- a Dimethicone/Trimethylsiloxysilicate treatment such as the Covasil 4.05 surface treatment marketed by LCW;
- a Lauroyl Lysine treatment such as the LL surface treatment marketed by LCW - a Lauroyl Lysine Dimethicone treatment such as the LL/SI surface treatment marketed by LCW;
- a Magnesium Myristate treatment such as the MM surface treatment marketed by LCW;
- an Aluminum Dimyristate treatment such as the MI surface treatment marketed by Miyoshi;
- a Perfluoropolymethylisopropyl ether treatment such as the FHC surface treatment marketed by LCW;
- an Isostearyl Sebacate treatment such as the HS surface treatment marketed by Miyoshi;
- a Disodium Stearoyl Glutamate treatment such as the NAI surface treatment marketed by Miyoshi;
- a Dimethicone/Disodium Stearoyl Glutamate treatment such as the SA/NAI surface treatment marketed by Miyoshi;
- a Perfluoroalkyl Phosphate treatment such as the PF surface treatment marketed by Daito;
- an acrylate copolymer/dimethicone and perfluoalkyl phosphate treatment such as the FSA surface treatment marketed by Daito;
- a Polymethylhydrogen siloxane/Perfluoroalkyl Phosphate treatment such as the FS01 surface treatment marketed by Daito;
- a Lauryl Lysine/Aluminum Tristearate treatment such as the LL-StAI surface treatment marketed by Daito;
- an Octyltriethylsilane treatment such as the OTS surface treatment marketed by Daito;
- an Octyltriethylsilane/Perfluoroalkyl Phosphate treatment such as the FOTS surface treatment marketed by Daito;
- an Acrylate/Dimethicone Copolymer treatment such as the ASC surface treatment marketed by Daito;
- an Isopropyl Titanium Triisostearate treatment such as the ITT surface treatment marketed by Daito;
- a Microcrystalline Cellulose and Carboxymethyl Cellulose treatment such as the AC surface treatment marketed by Daito;
- a Cellulose treatment such as the C2 surface treatment marketed by Daito;
- an Acrylate copolymer treatment such as the APD surface treatment marketed by Daito;
- a Perfluoroalkyl Phosphate / Isopropyl Titanium Triisostearate treatment such as the PF + ITT surface treatment marketed by Daito

The composition in accordance with the present invention may also comprise one or more surface-untreated pigments.

According to a particular embodiment of the invention, the pigment or pigments are mineral pigments.

According to another particular embodiment of the invention, the pigment or pigments are chosen from nacres.

According to one particular embodiment of the invention, the dispersing agent is present with organic pigments in the dispersion (A), and/or the composition (B), and/or (C) or inorganic in the form sub-micron sized particle.

By “ sub-micronic ” or in English “ sub-micronic ” is meant pigments whose particle size has been micronized by the micronization method and whose average particle size is less than one micronmeter (μm), in particular between 0.1 and 0.9 μm, and preferably between 0.2 and 0.6 μm

According to one embodiment, the dispersing agent and the pigment(s) are present in an amount (dispersant: pigment) of between 0.5:1 and 2:1, particularly between 0.75:1 and 1.5:1 or better between 0.8:1 and 1.2:1.

According to a particular embodiment, the dispersing agent is suitable for dispersing the pigments and is compatible with a formulation curable by condensation.

“ Compatible ” means, for example, that said dispersing agent is miscible in the oily phase of the composition or of the dispersion containing the pigment(s), it does not delay or reduce the hardening. The dispersing agent is preferably cationic.

The dispersing agent(s) can therefore have a silicone backbone, such as silicone polyether and dispersants of the amino-silicone type. Among the suitable dispersing agents, mention may be made of:
- amino-silicones, ie silicones comprising one or more amino groups such as those marketed under the names and references: BYK LPX 21879, by BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, marketed by Genesee polymers,
- silicone acrylates such as Tego ^® RC 902, Tego ^® RC 922, Tego ^® RC 1041, and Tego ^® RC 1043, marketed by Evonik,
- polydimethylsiloxane (PDMS) silicones with carboxylic groups such as X-22162 and X-22370 by Shin-Etsu, silicone epoxy such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682, and GP-695, by Genesee Polymers, or Tego ^® RC 1401, Tego ^® RC 1403, Tego ^® RC 1412, by Evonik.

According to a particular embodiment, the dispersing agent(s) are of the amino-silicone type and are positively charged.

Mention may also be made of dispersing agents having chemical groups capable of reacting with the reagents of the oily phase and thus are capable of improving the 3D network formed from the amino-silicone. For example, silicone epoxy pigment dispersing agents can react chemically with the amino-silicone prepolymer amino group(s) to increase the cohesion of the amino-silicone film comprising the pigment(s).

Preferably, the pigment(s) v) of the invention are chosen from carbon black, iron oxides, in particular red and black, and micas coated with iron oxide, triarylmethane pigments, in particular blue and purple, such as BLUE 1 LAKE, azo pigments in particular red such as D&C RED 7 alkali metal salt of lithol red such as the calcium salt of lithol red B.

According to a particular embodiment of the invention, the quantity of pigments varies from 0.5% up to 40%, and preferably from 1 to 20% relative to the weight of the composition and dispersion comprising them.

Process in at least 2 application steps:

According to an advantageous variant of the invention, the method of the invention is a method for treating keratin materials, in particular the skin, preferably human, and more preferably the face such as the lips, comprising:
1) the application to said materials of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously; and
ii) one or more stabilizing agent(s) consisting of ethylenic polymer(s) chosen from c) and d) as defined above;
iii) one or more hydrocarbon oil(s) as defined above, v) one or more plasticizer(s) and vi) one or more cosmetic agent(s), preferably pigment (s);
followed by
2) the application to said materials of a composition (B), comprising:
iv) one or more amine compound(s) chosen from e) and f) as defined above and optionally a polar protic solvent such as water.

According to another advantageous variant of the invention, the method of the invention is a method for treating keratin fibers, in particular human fibers, preferably the hair, comprising:
1) the application to said fibers of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously; and
ii) one or more stabilizing agent(s) consisting of ethylenic polymer(s) chosen from c) and d) as defined above;
iii) one or more hydrocarbon oil(s) as defined above, v) one or more plasticizer(s) and vi) one or more dye(s) and/or pigment(s) ;
followed by
2) the application to said fibers of a composition (B), comprising:
iv) one or more amino compound(s) chosen from e) and f) as defined above and optionally one or more polar protic solvent(s) such as water.

According to another advantageous variant of the invention, the method of the invention is a method for treating keratin materials, in particular the skin, preferably human, and more preferably the face such as the lips, comprising:
1) the application to said materials of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined above;
ii) one or more stabilizing agent(s) consisting of ethylenic polymer(s) chosen from c) and d) as defined above; and
iii) one or more hydrocarbon oil(s) as defined above and v) one or more plasticizer(s);
followed by
2) the application to said materials of a composition (B) comprising:
iv) one or more amino compound(s) chosen from e) and f) as defined previously; and vi) one or more cosmetic agent(s), preferably one or more pigment(s); and optionally one or more polar protic solvent(s) such as water.

According to yet another advantageous variant of the invention, the method of the invention is a method for treating keratin fibres, in particular human fibers, preferably the hair, comprising:
1) the application to said fibers of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously; and
ii) one or more stabilizing agent(s) consisting of ethylenic polymer(s) chosen from c) and d) as defined above; and
iii) one or more hydrocarbon oil(s) as defined above; and v) one or more plasticizer(s);
followed by
2) the application to said fibers of a composition (B) comprising:
iv) one or more amino compound(s) chosen from e) and f) as defined previously; and vi) one or more dye(s) and/or pigment(s) and optionally one or more polar protic solvent(s) such as water.

According to yet another advantageous variant of the invention, the method of the invention is a method for treating keratin fibres, in particular human fibers, preferably the hair, comprising:
1) the application to said fibers of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously; and
ii) one or more stabilizing agent(s) consisting of ethylenic polymer(s) chosen from c) and d) as defined previously; and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
2) the application to said fibers of a composition (B) comprising:
iv) one or more amino compound(s) chosen from e) and f) as defined previously; and v) one or more plasticizer(s) and one or more colorant(s) and/or pigment(s); and optionally one or more polar protic solvent(s) such as water.

According to yet another variant of the invention, the method of the invention is a method for treating keratin materials, in particular the skin, preferably human, and more preferably the face such as the lips, comprising:
1) the application to said materials of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously;
ii) one or more stabilizing agent(s) consisting of ethylenic polymer(s) chosen from c) and d) as defined previously; and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
2) the application to said materials of a composition (B), comprising: vi) one or more cosmetic active ingredient(s), preferably pigment(s) and iv) one or more amine compound(s) s) chosen from e) and f) as defined above and optionally iii) one or more hydrocarbon oil(s) as defined above and optionally one or more solvent(s) polar protic(s) such as water;
followed by
3) the application to said materials of a composition (C) comprising v) one or more plasticizer(s) and optionally iii) one or more hydrocarbon oil(s) as defined above .

According to yet another variant of the invention, the method of the invention is a method for treating keratin fibers, in particular human fibers, preferably the hair, comprising:
1) the application to said fibers of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously;
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from c) and d) as defined previously; and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
2) the application to said fibers of a composition (B), comprising:
iv) one or more amino compound(s) chosen from e) and f) as defined above and optionally one or more polar protic solvent(s) such as 'water ;
followed by
3) the application to said fibers of a composition (C) comprising one or more plasticizer(s); and vi) one or more dye(s) and/or pigment(s) and optionally iii) one or more hydrocarbon oil(s) as defined above.

According to yet another advantageous variant of the invention, the method of the invention is a method for treating keratin materials, in particular the skin, preferably human, and more preferably the face such as the lips, comprising:
1) the application to said materials of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously;
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from c) and d) as defined previously; and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
2) the application to said materials of a composition (C) comprising; v) one or more plasticizer(s) and vi) one or more cosmetic active ingredient(s), preferably pigment(s); followed by the application to said materials of a composition (B) comprising iv) one or more amine compound(s) chosen from e) and f) as defined previously and optionally one or more solvent(s) s) polar protic(s) such as water.

According to yet another advantageous variant of the invention, the method of the invention is a method for treating keratin fibres, in particular human fibers, preferably the hair, comprising:
1) the application to said fibers of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously;
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from c) and d) as defined previously; and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
2) the application to said fibers of a composition (C) comprising v) one or more plasticizer(s), and vi) one or more one or more cosmetic active ingredient(s), preferably coloring agent(s) and / or pigment(s) and optionally iii) one or more hydrocarbon oil(s) as defined above; followed by
3) the application to said fibers of a composition (B) comprising iv) one or more amine compound(s) chosen from e) and f) as defined previously and optionally one or more solvent(s) s) polar protic(s) such as water.

According to yet another variant of the invention, the method of the invention is a method for treating keratin fibers, in particular human fibers, preferably the hair, comprising:
1) the application to said fibers of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously; and
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from c) and d) as defined previously; and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
2) the application to said fibers of a composition (B), comprising: v) one or more plasticizer(s) and iv) one or more amino compound(s) chosen from e) and f ) as defined above and optionally one or more polar protic solvent(s) such as water;
followed by
3) the application to said fibers of a composition (C) comprising vi) one or more cosmetic agent(s), preferably coloring agent(s) and/or pigment(s) and optionally iii) one or more oil (s) hydrocarbon(s) as defined above.

According to a particularly preferred variant of the invention, the method of the invention is a method for treating keratin materials, in particular the skin, preferably human, and more preferably the face such as the lips, comprising:
1) the application to said materials of a composition (C) comprising v) one or more cosmetic active ingredient(s), preferably pigment(s) and optionally iii) one or more hydrocarbon oil(s) ) as defined above; followed by
2) the application to said materials of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously; and
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from c) and d) as defined previously; v) one or more plasticizer(s), and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
3) the application to said materials of a composition (B) comprising iv) one or more amine compound(s) chosen from e) and f) as defined previously and optionally one or more solvent(s) s) polar protic(s) such as water.

According to yet another variant of the invention, the method of the invention is a method for treating keratin fibers, in particular human fibers, preferably the hair, comprising:
1) the application to said materials of a composition (C) comprising v) one or more cosmetic active ingredient(s), preferably pigment(s) and optionally iii) one or more hydrocarbon oil(s) ) as defined above; followed by
2) the application to said materials of an oily dispersion (A) comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s) a) and b) as defined previously; and
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from c) and d) as defined previously; v) one or more plasticizer(s), and
iii) one or more hydrocarbon oil(s) as defined above;
followed by
3) the application to said materials of a composition (B) comprising iv) one or more amine compound(s) chosen from e) and f) as defined previously and optionally one or more solvent(s) s) polar protic(s) such as water.

According to another particular variant of the invention, the cosmetic agent(s) vi) as defined above, in particular the pigments, are found in a composition (C). The latter can be applied simultaneously with composition (A), or with composition (B). Preferably, composition (C) is applied after step 1), ie after applying composition (A), more preferably compositions (A) and (B) do not include hair dye and it is applied after step 1) of the process of the invention a composition (C) comprising one or more hair dyes v) as defined above, followed by the application to the keratin materials of the composition (B).

The dispersion of the invention the dispersion (A), and the compositions (B) and (C) are cosmetic, i.e. they only comprise cosmetically acceptable ingredients.

According to a preferred embodiment of the invention, the dispersion (A), and the compositions (B) and (C) are anhydrous.

According to another advantageous embodiment, dispersion (A) and composition (B) are anhydrous, and composition (C) is aqueous.

According to a particular embodiment of the invention, composition (B) is aqueous or aqueous-alcoholic.

According to another particularly advantageous embodiment of the invention, composition (C) is aqueous or aqueous-alcoholic.

According to yet another advantageous embodiment, dispersion (A) is anhydrous and composition (B) and composition (C) are aqueous or aqueous-alcoholic, preferably aqueous.

Compositions (B) and (C) and dispersion (A) according to the invention may comprise a cosmetic additive chosen from water, perfumes, preservatives, fillers, oils, waxes, surfactants, moisturizers , vitamins, ceramides, antioxidants, anti-free radical agents, polymers, thickeners, coloring matter.

The compositions (B) and (C) and dispersion (A) according to the invention can also comprise other dyestuffs such as fat-soluble dyes, water-soluble dyes. This dyestuff may be present in a content ranging from 0.01% to 30% by weight, relative to the total weight of the composition containing them, preferably from 0.01% to 10% by weight.

Examples of fat-soluble dyes are Sudan Red, D&C Red 17, D&C Green 6, β-carotene, soybean oil, Sudan Brown, D&C Yellow 11, D&C Violet 2, D&C Orange 5, quinoline yellow, annatto. Water-soluble dyes are for example beet juice, methylene blue.

According to one embodiment, the dispersion (A) and the compositions (B) and (C) according to the invention are anhydrous compositions.

Preferably, the first step of the process of the invention is the application of the dispersion (A) in one or more volatile apolar solvents, in particular isododecane.

According to another variant, step 2) follows step 1) without intermediate rinsing or drying. Preferably after application of the dispersion (A) during step 1), one waits between 1 minute and 6 hours, in particular between 10 minutes and 5 hours, more particularly between 30 minutes and 4 hours, preferably around 3 hours , to apply composition (B).

If the first step is the step of applying composition (C) followed by the application of the oily dispersion (A) then the application of composition (A) between the application of composition (C) (step 1) and the step of applying the dispersion (A) (step 2) the keratin materials are preferably air-dried.

If the first step is the step of applying the oily dispersion (A) and the second step is that of applying the composition (C) and the third step is that of applying the composition (B) between the application of composition (C) as defined above (step 2) and the step of applying composition (B) (step 3) the keratin materials are preferably air-dried.

If the first step is the application of the oily dispersion (A) then the application of the composition (B) then the application of the composition (C) between the application of the composition (C) (step 3) and the step of applying composition (B) (step 2) the keratin materials are preferably air-dried.

The set

The invention also relates to a kit or device with several separate compartments comprising:
- in a first compartment: the dispersion (A) as defined previously,
- in a second separate compartment: composition (B) as defined above, and
- optionally in a third compartment separate from the other two: the composition (C) as defined above.

The packaging assembly for the compositions is, in a known manner, any packaging suitable for storing cosmetic compositions (bottles, tube, spray bottle, aerosol bottle in particular).

A subject of the invention is also the oily dispersion (A) as defined previously comprising v) one or more plasticizer(s) and v) the cosmetic agent(s) as defined previously.

A subject of the invention is also the oily dispersion (A) which is in an inverse emulsion (W/O) as defined previously.

The invention is further illustrated in the following examples.

EXAMPLES

Example 1:

The oily dispersions (A) are formed as a whole [particles i) + stabilizing agent ii)] at:
- 70% by weight of a) (C ₁ -C ₄ )(alkyl)acrylate (C ₁ -C ₄ )alkyl (such as Ethyl Acrylate),
- 10% by weight of b) ethylenically unsaturated anhydride compound (such as maleic anhydride), and
- 20% by weight of c) polymers of (C ₁ -C ₆ )(alkyl)acrylate monomers of (C ₃ -C ₁₂ )cycloalkyl (such as Isobornyl Acrylate).

The preparation of these oily dispersions was carried out in a 1 liter controlled reactor. The synthesis is carried out in two steps:

During a first step, Isobornyl Acrylate is polymerized in Isododecane / Ethyl Acetate (60/40) in the presence of a small amount of Ethyl Acrylate and a radical initiator (T21S). In the first step, the Isobornyl Acrylate / Ethyl Acrylate mass ratio is 92/8.

During the second step, the rest of the Ethyl Acrylate and the Maleic Anhydride are poured in the presence of Isododecane / Ethyl Acetate (60/40) and Trigonox 21S (T21S) radical initiator.

After stripping, the polymer has a dry extract of 52% in Isododecane. The ratios used to obtain the stabilizing agent and the particulate core are summarized in the Table below:

Quantity of reagents:

Experimental protocol :

Isododecane/Ethyl Acetate (60/40), Isobornyl Acrylate, Ethyl Acrylate and T21S are introduced into a reactor at the bottom of the tank. The medium is heated to 90° C., under argon and with stirring. The dry extract during this first step is 35.9%, at least 2 hours.

After 2 hours of reaction, isododecane / ethyl acetate (60/40) are introduced into the base stock. The medium is heated to 90° C. and then the Ethyl Acrylate/Maleic Anhydride, Isododecane/Ethyl Acetate (60/40), and the T21S are introduced over 2 hours by pouring. At the end of the casting the medium is milky. The mixture is left for at least 7 h at 90° C. with stirring.

1L of isododecane and ethyl acetate are then stripped (the NMR indicates that there are no more monomers and the ethyl acetate is completely removed from the dispersion).

Polyamine used:

Application process on keratin materials:

The different process steps for the treatment of keratin materials on keratin fibers to evaluate the coloring of natural white hair at 90% white:
1. Application to dry hair of compositions (A1) to (A5) according to a bath ratio of 0.5 g of formula/g of hair;
2. The lock is dried with a hair dryer;
3. After application of compositions (A1) to (A5), application of composition (B) according to a bath ratio of 0.5 g of formula/g of hair;
4. The wick is dried with a hair dryer
5. Shampoo resistance evaluations are thus conducted 1 hour after application, followed by 5 shampoos

Color measurements:

The colorimetric data of each of the locks are measured with a Minolta CM-3610d spectrophotometer. In this L* a* b* system, L* represents the brightness, a* indicates the green/red color axis and b* the blue/yellow color axis. The higher the value of L, the lighter or less intense the color. Conversely, the lower the value of L, the darker or more intense the color. The higher the value of a* the more red the shade and the higher the value of b* the more yellow the shade.

The increase in color on the hair therefore corresponds to the variation in color between the locks of uncolored hair BN (natural white to 90% white) and the colored hair which is measured by (ΔE) according to the following equation:

In this equation, L*, a* and b* represent the values measured after coloring the BN hair and L0*, a0* and b0* represent the values measured before coloring. The higher the value of ΔE, the better the rise of the color.

Results:

The shampoo persistence results are presented in the table below:

It appears from the results that the color is more intense for the processes according to the invention compared to the comparative process. In addition, the persistence results show that the presence of plasticizer of the process according to the invention makes it possible to significantly improve the persistence of shampoos.

Claims (23)

Process for treating keratin materials, preferably human, in particular the skin, and more preferably the face such as the lips, or keratin fibers, in particular human, such as the hair, comprising:
1) the application to said materials of an oily dispersion (A), preferably anhydrous, comprising:
i) one or more particle(s) consisting of one or more ethylenic copolymer(s):
a) (C ₁ -C ₄ )(alkyl)acrylate (C ₁ -C ₄ )alkyl, preferably (meth)acrylate (C ₁ -C ₄ )alkyl and
b) an ethylenically unsaturated anhydride compound, preferably maleic anhydride; and
ii) one or more stabilizing agents consisting of ethylenic polymers chosen from:
c) polymers of (C ₁ -C ₆ )(alkyl)acrylate (C ₃ -C ₁₂ )cycloalkyl monomers; and
d) copolymers of (C ₁ -C ₆ )(alkyl)acrylate, (C ₃ -C ₁₂ )cycloalkyl and (C ₁ -C ₄ )(alkyl)acrylate (C ₁ -C ₄ )alkyl; and
iii) one or more hydrocarbon oil(s); followed by
2) the application to said materials of a composition (B), preferably anhydrous, comprising:
iv) one or more amino compound(s) chosen from:
e) polyamino compounds having several primary amine and/or secondary amine groups, and
f) amino alkoxysilanes,
it being understood that the process of the invention uses v) one or more plasticizer(s), and vi) one or more cosmetic active ingredient(s) chosen from a) dyes and/or pigments, b) active ingredients for the care of keratin materials, in particular the skin, and c) UV filters as well as d) mixtures thereof, the ingredients v) and vi) possibly being found in composition (A), and/or in composition ( B), and/or in another composition (C). Process according to the preceding claim, in which the oily dispersion (A) comprises one or more particles consisting of one or more ethylenic copolymers of a) of (C ₁ -C ₄ )(alkyl)acrylate of (C ₁ -C ₄ )alkyl which has the formula H ₂ C=C(R)-C(O)-O-R' with R representing a hydrogen atom or a (C ₁ -C ₄ )alkyl group such as methyl, and R' representing a (C ₁ -C ₄ )alkyl such as methyl or ethyl, preferably C ₁ -C _{4 alkyl (meth)acrylate,} particularly the polymer of the particles is a polymer of C ₁ -C ₄ alkyl (meth)acrylate ;
particularly a) is chosen from C ₁ -C ₄ alkyl (meth)acrylate such as methyl acrylate (meth)acrylate, ethyl (meth)acrylate, n- propyl, isopropyl (meth)acrylate, n-butyl (meth)acrylate, or tert-butyl (meth)acrylate; preferably chosen from methyl acrylate and ethyl acrylate. Process according to any one of the preceding claims, in which the oily dispersion (A) comprises one or more particles consisting of one or more ethylenic copolymers of b) ethylenically unsaturated anhydride compound b) chosen from derivatives of maleic anhydride (Ib) and itaconic anhydride (IIb):

Formulas (Ib) and (IIb) in which R _a , R _b and R _c , identical or different, representing a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably R _a , R _b , and R _c represent a hydrogen atom;
preferentially, ingredient b) is of formula (Ib) and more preferentially is maleic anhydride. Process according to any one of the preceding claims, in which the polymer(s) of the particles i) of the dispersion (A) comprise, or consist essentially of, from 80 to 99.99% by weight of the ingredient a) and from 0, 01 to 20% by weight of ingredient b), based on the total weight of the polymer. Process according to any one of the preceding claims, in which the polymer of the particles i) is present in the dispersion (A) in an amount ranging from 20 to 60% by weight, relative to the total weight of the dispersion (A), in particular between 21% to 58.5% by weight, relative to the total weight of the dispersion (A), preferably ranging from 30 to 50% by weight, relative to the total weight of the dispersion (A), more preferably ranging from 36 % to 42% by weight relative to the total weight of the dispersion (A).
. Process according to any one of the preceding claims, in which the stabilizing agent(s) ii) of the dispersion (A) consists of ethylenic polymers chosen from:
c) polymers of monomers of formula H₂C=C(R)-C(O)-O-R’’ with R representing a hydrogen atom or group (C₁-VS₄)alkyl such as methyl, and R’’ representing a group (C₅-VS₁₀)cycloalkyl such as norbornyl, or isobornyl preferably isobornyl ; and d) copolymers of H₂C=C(R)-C(O)-O-R’ and of H₂C=C(R)-C(O)-O-R'' with R, R' and R'' as previously defined; particularly the stabilizing agent ii) is an isobornyl (meth)acrylate polymer chosen from isobornyl (meth)acrylate homopolymer and random copolymers of isobornyl (meth)acrylate and isobornyl (meth)acrylate C-alkyl₁-VS₄preferably present according to an isobornyl (meth)acrylate / C-alkyl (meth)acrylate weight ratio₁-VS₄greater than 4; advantageously, said weight ratio ranges from 4.5 to 19 Process according to any one of the preceding claims, in which the combination of i) particle(s) + ii) stabilizing agent(s) present in the dispersion (A) comprises from 10 to 50% by weight of copolymers d) better from 15 to 30% by weight of copolymer d) and from 50 to 90% by weight of polymer c) better from 70 to 85% by weight of polymer c), relative to the total weight of the whole i ) stabilizing agent(s) + ii) polymer particle(s). Process according to any one of the preceding claims, in which the hydrocarbon oil(s) iii) of the dispersion (A) is (are) apolar, ie formed solely of carbon and hydrogen atoms, in particularly volatile; more particularly chosen from hydrocarbon oils having from 8 to 14 carbon atoms; preferentially isododecane and octyldodecanol, more preferentially isododecane; or else a mixture of non-volatile and volatile oil, preferably the mixture comprises isododecane as the volatile oil and a phenyl silicone oil such as a pentaphenyl silicone oil. Process according to any one of the preceding claims, in which the dispersion (A) is in an inverse emulsion, i.e. of the water-in-oil (W/O) type and comprises one or more surfactants, preferably nonionic. Process according to any one of the preceding claims, in which the amino compound(s) iv) of composition (B) is (are) chosen from amino alkoxysilanes f) in particular chosen from those of formula(IVa):
R' ₁ -If(OR' ₂ ) _z (R' ₃ ) _x (IVa)
Formula(IVa)in which :
-R' ₁ is a C hydrocarbon chain₁-VS₁₀, linear or branched, saturated or unsaturated, cyclic or acyclic, substituted by one or more groups chosen from the groups: i) primary amine NH₂or secondary N(H)R with R representing a group (C₁-VS₄)alkyl, ii) aryl or aryloxy substituted by an amino group, (C₁-VS₄)alkylamino or by a C aminoalkyl group₁-VS₄and ii) aldehyde –C(O)-H, carboxy –C(O)-OH, amide –C(O)-NH₂or urea –NH-C(O)-NH₂;
-R' ₁ is optionally interrupted in its hydrocarbon chain by one or more heteroatoms (in particular O, S, NH), a carbonyl group (CO), or their combination such as ester –C(O)-O-, or amide –C(O) -NH-, R'₁being bonded to the silicon atom directly via a carbon atom,
-R' ₂ andR' ₃ identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atoms,
-zdenotes an integer ranging from 1 to 3, and
-xdenotes an integer ranging from 0 to 2, with z+x=3;
preferably, the amino alkoxysilane of formula (IVa) is chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane; more preferentially 3-aminopropyl triethoxysilane (APTES). Process according to any one of Claims 1 to 9, in which the amino compound(s) iv) of composition (B) is (are) chosen from e) polyamino compounds having several primary amine groups and / or secondary amine chosen in particular from:
- poly((C ₂ -C ₅ )alkylene imines), and in particular polyethyleneimines and polypropyleneimines, preferably poly(ethyleneimine);
- poly(allylamines);
- polyvinylamines and their copolymers, in particular with vinylamides;
- polyamino acids having NH ₂ groups such as polylysine;
- amino dextran;
- polyvinyl amino alcohol,
- copolymers based on acrylamidopropylamine;
- polysaccharides containing amine group(s) such as chitosan; and
polydi(C ₁ -C ₄ )alkylsiloxanes comprising amine groups at the end of the chain or on the side chains. Process according to any one of Claims 1 to 11, in which the amino compound(s) iv) of composition (B) is (are) chosen from e) polyamino compounds having several primary amine groups and / or secondary amine chosen in particular from polysaccharides containing amine group(s) as well as their organic or mineral acid salts, their α or β anomers, their optical isomers of L or D configuration and their solvates such as than hydrates; more particularly the polysaccharide(s) containing amine group(s) of is(are) containing a C sugar unit₆with amine(s) group(s), preferably interconnected between the atoms of carbon 1 of an osidic unit and of carbon 4 of the other osidic unit, denoted (1→4), such as the polysaccharide with group (s) amine(s) of formula(B)following, as well as their organic or inorganic acid salts, their α or β anomers, their optical isomers of L or D configuration and their solvates such as hydrates:
(B)
Formula(B)in which :
- R radicals_at, R_b, R_vsof each osidic unit can be identical or different;
-notis an integer greater than or equal to 2, particularly comprised inclusively between 3 and 3000, more particularly between 5 and 2500, preferentially between 10 and 2300;
-R _at ,R _b , andR _vs , identical or different, represent i) hydroxy, ii) (C₁-VS₄)alkoxy, the alkyl group of which may be optionally substituted, in particular by one or more hydroxy, iii) carboxy, and iv) NR groups₁R₂with R₁and R₂as previously defined, in particular R₁and R₂are chosen from the hydrogen atom and –C(O)-R’₁in which R'₁is as defined above; preferably R₁and R₂represent i) hydrogen atom or ii) –C(O)-R’₁and R'₁representing a group (C₁-VS₄) alkyl such as methyl;
it being understood that at least one of the radicals R_at, R_bor R_vsof at least one carbohydrate unit represents an NR group₁R₂and that at least one of the NR groups₁R₂of at least one saccharide unit represents a NH group₂; preferablyR _at of at least one sugar unit represents an NR group₁R₂with R₁which represents a hydrogen atom and R₂is selected from i) a hydrogen atom or ii) a –C(O)-R’ group₁, andR _b andR _vs , represent a hydroxy group, provided that at least one of the NR groups₁R₂of at least one saccharide unit represents a NH group_2;preferably the polysaccharides of the invention are chosen from the compounds of formula(B ₂ )following as well as their acid salts, organic or inorganic, and their solvates such as hydrates:
(B ₂ )
Formula(B ₂ )in which :
-R _at ,R _b , andR _vs , are as defined for(B)previously; and.
- R radicals_at, R_b, R_vsof each osidic unit can be identical or different;
- notis an integer greater than or equal to 2, particularly comprised inclusively between 3 and 3000, more particularly between 5 and 2500, preferentially between 10 and 2300;
it being understood that in the polysaccharide (B ₂ ) at least one of the radicals R_at, R_bor R_vsof at least one carbohydrate unit represents an NR group₁R₂and that at least one of the NR groups₁R₂of at least one saccharide unit represents a NH group₂; preferably at least one osidic unit bears an R group_atamino NH₂and at least one other sugar unit bears an R group_atwhich represents -N(H)-R’ with R’ representing a group (C₁-VS₄)alkylcarbonyl such as acetyl CH₃-C(O)-;
particularly the polysaccharide(s) containing amine group(s) of the invention is (are) chosen from chitosans, salified with organic acid, preferably with carboxylic acid, in particular acid (C₁-VS₆)alkylcarboxylic acid such as acetic acid. Process according to any one of Claims 1 to 12, in which the plasticizer(s) v) is (are) chosen from those of the families of phthalates, esters, citrates, benzoates, citrates and siloxanes, in particular the plasticizer(s) are chosen from the compounds(V),and(VI')below :
R ^h -OC(O)-L-[C(O)-OR ^I ] _not (V)
Formula(V)in which :
-R ^h , andR ^I , same or different represent a group (C₁-VS₂₀)alkyl, aryl such as phenyl, aryl(C₁-VS₄)alkyl such as benzyl, preferably (C₁-VS₄)alkyl such asnot-butyl;
- notis 1, 2 or 3, preferably 2; and
- Lis a) C-alkyl₁-VS₁₀, di, tri or tetravalent, preferably (C₂-VS₈) trivalent alkyl, said di, tri or tetravalent alkyl, possibly being substituted by one or more hydroxy groups, b) di, or trivalent cycloalkyl, or c) di, tri or tetravalent aryl, preferably di, or trivalent phenyl, of preferably L represents a group a); preferably the compounds(V)are chosen from the compounds of(V')below :
R ^h -OC(O)-L-[C(O)-OR ^I ] _not (V')
Formula(V')in which :
-R ^h , andR ^I , same or different represent a group (C₁-VS₆)alkyl, aryl(C₁-VS₄)alkyl such as benzyl, preferably (C₁-VS₄)alkyl such asnot-butyl;
- notis 1, or 2, preferably 2; and
- Lis a) C-alkyl₂-VS₆, di, tri or tetravalent, preferably (C₂-VS₈) trivalent alkyl, said alkyl possibly being substituted by one or more hydroxy groups, preferably substituted by a hydroxy group;
(VI)
Formula(VI)in which :
-R ^I , identical or different, preferably identical, represents a group (C₁-VS₁₀)alkyl, aryl such as phenyl, aryl(C₁-VS₄)alkyl such as benzyl, preferably aryl such as phenyl,
-R ^I identical or different, preferably identical represents a hydrogen atom, or a hydroxy group, (C₁-VS₆)alkyl, or (C₁-VS₆)alkoxy,
- L'represents a group selected from a) C-alkyl₂-VS₁₀, divalent, preferably (C₄-VS₈)divalent alkyl, which may optionally be substituted by one or more hydroxy groups, and/or interrupted by one or more oxygen atoms, and/or interrupted by one or more divalent groups -Si(R^I)(R^k)- with R^Iand R^kas defined above, b) di, or trivalent cycloalkyl, c) di, tri or tetravalent aryl, and d) -Si(R^I)(R^k)-, preferably L' represents a group d) -Si(R^I)(R^k)-;
preferably the compounds of formula(VI)are chosen from the compounds of formula(VI'):
(VI')
Formula(VI')in which :
-R ^I , identical or different, preferably identical, represents an aryl group such as phenyl, aryl(C₁-VS₄)alkyl such as benzyl, preferably aryl such as phenyl, and
-R ^I identical or different, preferably identical, represents a group represents (C₁-VS₆)alkyl, preferably (C₁-VS₄)alkyl such as methyl. Process according to any one of Claims 1 to 13, in which the plasticizer(s) v) is (are) present in the composition (A), and/or in the composition (B), and/or in a another composition (C); preferably the plasticizer(s) as defined in claim 1 or 13 is (are) present in composition (A) and/or in an amount of between 0.5 and 30% by weight, in particular between 1 and 20%, preferably from 1.5 to 10% by weight relative to the total weight of composition (A), and/or in composition (B), and/or in another composition (C), preferably relative to the total weight of composition (A). Process according to any one of the preceding claims, in which the composition (B) is aqueous and preferably also comprises one or more polysaccharides containing amine group(s) such as chitosan and/or one or more polyamino acids, preferably polylysines . Process according to any one of the preceding claims, in which vi) the cosmetic agent(s) is (are) chosen from dyes and/or pigments, preferably pigments, in particular chosen from:
- organic pigments nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, of metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane, quinophthalone; the white or colored organic pigments are chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Color Index under the references pigment BLUE 1 LAKE Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Color Index under the references Cl 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005 codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120 12370, 12420, 12490, 14700, 15525, 15580, 15800, 15850, 15865, 15880, 17200, 45, 4580, 458, 73915, 73360, 73915, 73360, 73915, 73360, 73915, 75470, the pigments obtained by oxidizing polymerization of indolic derivatives , or phenolics;
- Mineral pigments or inorganic pigments chosen from the mineral pigments useful in the present invention, iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide ;
more preferably the pigments vi) are chosen from carbon black, iron oxides in particular red and black and micas coated with iron oxide, triarylmethane pigments in particular blue and violet such as BLUE 1 LAKE, azo pigments in particular reds such as D&C RED 7 alkali metal salt of lithol red such as calcium salt of lithol red B. Process according to any one of the preceding claims, in which vi) the cosmetic agent(s), preferably pigment(s) as defined in claim 1, or 16 and the plasticizer(s) s) as defined in any one of claims 1, 13 or 14, is (are) in the dispersion (A) as defined in any one of claims 1 to 9. Process according to any one of Claims 1 to 16, in which vi) the cosmetic active ingredient(s), preferably pigment(s) as defined in Claim 1, or 16 and the the plasticizer(s) as defined in any one of Claims 1, 13 or 14, is (are) in composition (B) as defined in any one of Claims 1, 10 to 15. A method according to any of claims 1 to 16 comprising:
1) the application to said materials of an oily dispersion (A) as defined in any one of claims 1 to 9 and 14; followed by
2) the application to said materials of a composition (C) comprising v) one or more cosmetic active ingredient(s), preferably pigment(s) as defined in any one of the claims 1, or 16; followed by
3) the application to said materials of a composition (B) as defined in any one of claims 1, 10 to 15. A method according to any of claims 1 to 16 comprising:
1) the application to said materials of a composition (C) comprising v) one or more cosmetic active ingredient(s), preferably pigment(s) as defined in any one of the claims 1, or 16; followed by
2) the application to said materials of an oily dispersion (A) as defined in any one of claims 1 to 9 and 14; followed by
3) the application to said materials of a composition (B) as defined in any one of claims 1, 10 to 15. Process according to any one of the preceding claims, in which between stage 1) and stage 2), there is no rinsing, and the keratin materials are dried in air, preferably after application of the dispersion (A) during step 1) one waits between 1 minute and 6 hours, in particular between 10 minutes and 5 hours, more particularly between 30 minutes and 4 hours, preferably around 3 hours, to apply the composition ( B). kit or device with several separate compartments comprising:
- in a first compartment: the dispersion (A) as defined in any one of claims 1 to 9 and 14,
- in a second separate compartment: composition (B) as defined in any one of claims 1, 10 to 15, and
- optionally in a third compartment distinct from the other two: the composition (C) comprising one or more cosmetic agents as defined in claim 1, or 14. Oily dispersion (A) as defined in any one of claims 1 to 9 and 14 comprising one or more plasticizer(s) v) as defined in any one of claims 1, 13 or 14 and vi) one or more cosmetic active ingredient(s), preferably pigment(s) as defined in any one of claims 1 or 16.