Cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one particular additional compound, for improving the color of artificially dyed keratin fibers

Disclosed herein are processes for improving the color of artificially dyed keratin fibers, for protecting the color of artificially dyed keratin fibers and also their cosmetic properties with respect to washing, and/or for unifying the color of keratin fibers after dyeing them, comprising applying to the fibers a cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral and organic bases, and C1-C8 lower alcohols.

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Description

This application claims benefit of U.S. Provisional Application No. 60/801,066, filed May 18, 2006, the contents of which are incorporated herein by reference. This application also claims benefit of priority under 35 U.S.C. § 119 to French Patent Application No. FR 06/03279, filed Apr. 13, 2006, the contents of which are also incorporated herein by reference.

Disclosed herein is a process for improving the coloration of artificially dyed keratin fibers, for example, human keratin fibers, such as human hair, comprising applying a cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one additional agent chosen from conditioning agents and additional compounds.

Also disclosed herein are pretreatment and/or post-treatment processes for the dyeing of keratin fibers comprising applying a composition of the present disclosure to the keratin fibers.

Further disclosed herein are dyeing processes for keratin fibers comprising applying a composition of the present disclosure to the keratin fibers.

It is known practice to dye keratin fibers, for example, human keratin fibers such as the hair, with dye compositions comprising oxidation dye precursors, which are generally known as oxidation bases. These oxidation bases are colorless or weakly colored compounds, which, when combined with oxidizing products, give rise to colored compounds via a process of oxidative condensation. It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloration modifiers. The variety of molecules used as oxidation bases and couplers allows a wide range of colors to be obtained.

It is also known practice to dye keratin fibers by direct dyeing. The process conventionally used in direct dyeing comprises applying to the keratin fibers direct dyes, which are colored and coloring molecules that have affinity for the fibers, leaving them to act, and then rinsing the fibers.

The colorations resulting therefrom are particularly chromatic colorations, but are, however, temporary or semi-permanent since the nature of the interactions that bind the direct dyes to the keratin fiber and their desorption from the surface and/or core of the fiber are responsible for their weak dyeing power and their poor wash-fastness.

The artificial color of hair provided by a direct or oxidation dyeing treatment is generally satisfactory on the day of application. However, these colors gradually diminish as a result of repeated washing, and the tints fade to produce colors that are less vivid and less aesthetic. This is particularly noticeable for “warm” shades containing red or coppery hues.

The use of commercial rinse-out and leave-in care products has hitherto not sufficiently improved the color-fastness of the artificial color of hair.

It is thus desirable to develop methods for protecting the artificial color from the effect of repeated washing and the effect of time.

Moreover, depending on the treatments to which the hair has been subjected (e.g, permanent-waving, successive bleaching, and/or dyeing), its condition may be relatively heterogeneous on the same head of hair. When a coloration is applied to this hair, commonly known as sensitized hair, the overall color obtained is not always uniform. It is thus desirable to provide treatments that, when applied before dyeing, make it possible to obtain a more uniform overall dyeing result, also known as unison.

Accordingly, there is a need for compositions that can lessen the inherent effect of the quality of the keratin fiber to be dyed on the expected hair coloration.

It is known practice, for instance, as described in French Patent Application No. 2 833 489 to use hair treatment compositions comprising electrophilic monomers, which can produce a coating on the hair that can remain after shampooing.

The present inventors have discovered, surprisingly and unexpectedly, that it is possible to use at least one electrophilic monomer in the presence of at least one conditioning agent and/or at least one additional compound for the purpose of solving at least one of the problems mentioned above.

The present inventors have also discovered, surprisingly and unexpectedly, that by applying a composition as disclosed herein to the hair, remanent coating or sheathing is formed in situ. Without wishing to be bound by theory, it appears that the hydroxide ions (OH−) contained in water at neutral pH are absorbed by the hair and trigger the anionic polymerization process at the composition-hair interface. The at least one conditioning agent and/or the at least one additional compound present in this composition are thus incorporated into the polymer structure obtained following the in situ polymerization of the cyanoacrylate monomer. The production of a particular coating covering the artificially dyed keratin fiber may have a “barrier effect”, thus avoiding the loss of the dyes during successive shampooing, and thus preserving the color of the fiber.

Furthermore, the present inventors have discovered, surprisingly and unexpectedly, that in addition to the effects obtained on the quality and remanence of the hair colorations, the cosmetic properties, such as pleasant feel, softness and/or ease of disentangling, can also be conserved during successive washing. Similarly, the production of a particular coating covering a sensitized keratin fiber may make it possible to unify the surface state of the hair before dyeing, without, however, opposing the uptake of the dyes, and may do so in a long-lasting manner.

The present inventors have also discovered, surprisingly and unexpectedly, that the application of a cosmetic composition of the present disclosure before or after hair dyeing can make it possible to obtain highly cosmetic deposits on the hair, the hairs not being stuck together and the deposit being smooth and being able to remain after shampooing.

Depending on the chosen formulation, this deposit may be accompanied by a gain in mass and in styling properties for the entire head of hair, or, in contrast, may have a non-“visible” natural feel.

As used herein, the term “human keratin fibers” means head hair and body hair, for example, the beard, moustache, eyelashes, and eyebrows.

As used herein, the term “artificially dyed keratin fibers” means keratin fibers dyed via a direct dyeing process and/or via an oxidation dyeing process.

As used herein, the term “washing” means at least one application to keratin fibers of a rinse-out aqueous composition, which is usually detergent, such as a shampoo. This expression also includes bathing and swimming, for example, in the sea and in a swimming pool.

As used herein, the term “conditioning agent” means any agent whose function is to improve the cosmetic properties of the hair, for example, the softness, disentangling, feel, smoothness, and/or static electricity.

Disclosed herein is thus a process for improving the color of artificially dyed keratin fibers, for example, human keratin fibers such as human hair, comprising applying a cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral bases, organic bases, and C1-C8 lower alcohols.

Also disclosed herein is a process for protecting the color of artificially dyed keratin fibers and their cosmetic properties with respect to washing.

Further disclosed herein is a process for treating keratin fibers to unify the color of the fibers following the dyeing thereof.

Still further disclosed herein is a dyeing process comprising applying to human keratin fibers, for example, the hair, a dye composition (A), and a composition (B) comprising a cosmetic composition of the present disclosure, wherein composition (B) is applied to the fibers before and/or after the application of composition (A).

Also disclosed herein is a multi-compartment coloring kit comprising at least one first compartment comprising a dye composition and at least one second compartment comprising a composition of the present disclosure.

The various embodiments of the present disclosure are described in more detail below. All meanings and definitions provided herein with respect to the compounds used in the present disclosure are applicable to all embodiments of the present disclosure.

Cyanoacrylate Monomers

The at least one cyanoacrylate monomer present in the composition of the present disclosure can be chosen, for example, from the monomers of formula (I):

wherein:

    • X is chosen from NH, S, and O,
    • R1 and R2, which may be identical or different, are chosen from sparingly electron-withdrawing groups and non-electron-withdrawing groups (sparingly inductive-withdrawing groups and non-inductive-withdrawing groups) such as:
    • hydrogen,
    • saturated or unsaturated, linear, branched, or cyclic hydrocarbon-based groups comprising, for example, from 1 to 20, or from 1 to 10 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR, —COOR, —COR, —SH, —SR, —OH, and halogen atoms,
    • modified or unmodified polyorganosiloxane residues, and
    • polyoxyalkylene groups,
      • R is chosen from saturated and unsaturated, linear, branched, and cyclic hydrocarbon-based groups comprising, for example, from 1 to 20, or from 1 to 10 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur atoms, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues that may be obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups; and
    • R′3 is chosen from hydrogen and saturated and unsaturated, linear, branched, and cyclic hydrocarbon-based groups comprising from 1 to 20, for instance, from 1 to 10 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur atoms, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues that may be obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups.

As used herein, the term “electron-withdrawing groups and inductive-withdrawing groups (—I)” means any group that is more electronegative than carbon. Such groups are described, for instance, in P. R. Wells, Prog. Phys. Org. Chem., Vol. 6, 111 (1968).

As used herein, the term “sparingly electron-withdrawing groups and non-electron-withdrawing groups” means any group whose electronegativity is less than or equal to that of carbon.

In at least one embodiment, the alkenyl and alkynyl groups may comprise from 2 to 20 carbon atoms, for example, from 2 to 10 carbon atoms.

Examples of saturated, unsaturated, linear, branched, and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, include, but are not limited to, linear or branched alkyl, alkenyl, and alkynyl groups, such as methyl, ethyl, n-butyl, tert-butyl, isobutyl, pentyl, hexyl, octyl, butenyl, and butynyl groups; cycloalkyl groups and aromatic groups.

Non-limiting examples of substituted hydrocarbon-based groups include, for instance, hydroxyalkyl groups and polyhaloalkyl groups.

Examples of unmodified polyorganosiloxanes include, but are not limited to, polyalkylsiloxanes such as polydimethylsiloxanes, polyarylsiloxanes such as polyphenylsiloxanes, and polyarylalkylsiloxanes such as polymethylphenylsiloxanes.

Suitable modified polyorganosiloxanes include, by way of non-limiting example, polydimethylsiloxanes containing at least one group chosen from polyoxyalkylene, siloxy, silanol, amine, imine, and fluoroalkyl groups.

Non-limiting examples of polyoxyalkylene groups include polyoxyethylene groups and polyoxypropylene groups comprising, for example, from 1 to 200 oxyalkylene units.

Suitable mono- and polyfluoroalkyl groups include, but are not limited to, groups such as —(CH2)n—(CF2)m—CF3 and —(CH2)n—(CF2)m—CHF2, wherein n is a number ranging from 1 to 20 and m is a number ranging from 1 to 20.

In at least one embodiment, the substituents R1 and R2 may be optionally substituted with a group having cosmetic activity, for instance, groups with coloring, antioxidant, UV-screening and conditioning functions.

Non-limiting examples of groups with a coloring function include, for instance, azo, quinone, methine, cyanomethine, and triarylmethane groups.

Non-limiting examples of groups with an antioxidant function include, but are not limited to, butylhydroxyanisole (BHA) groups, butylhydroxytoluene (BHT) groups, and vitamin E groups.

Non-limiting examples of groups with a UV-screening function include benzophenone, cinnamate, benzoate, benzylidenecamphor, and dibenzoylmethane groups.

Non-limiting examples of groups with a conditioning function include, but are not limited to, cationic groups and fatty ester groups.

In at least one embodiment, R1 and R2 are hydrogen atoms.

In another embodiment, R′3 is chosen from saturated hydrocarbon-based groups comprising from 1 to 10 carbon atoms and alkenyl groups comprising from 2 to 10 carbon atoms.

In yet another embodiment, X is O.

Examples of compounds of formula (I) that are suitable for use in accordance with the present disclosure include, but are not limited to, the monomers:

a) belonging to the family of polyfluoroalkyl 2-cyanoacrylates, such as:

the ester 2,2,3,3-tetrafluoropropyl 2-cyano-2-propenoate of formula (II):

and the ester 2,2,2-trifluoroethyl 2-cyano-2-propenoate of formula (III):

b) the alkyl and alkoxyalkyl 2-cyanoacrylates of formula (IV):

wherein R′3 is chosen from C1-C10 alkyl radicals and (C1-C4)alkoxy(C1-C10)alkyl radicals.

Further examples of such monomers include, but are not limited to, ethyl 2-cyanoacrylate, methyl 2-cyanoacrylate, n-propyl 2-cyanoacrylate, isopropyl 2-cyanoacrylate, tert-butyl 2-cyanoacrylate, n-butyl 2-cyanoacrylate, isobutyl 2-cyanoacrylate, 3-methoxybutyl cyanoacrylate, n-decyl cyanoacrylate, hexyl 2-cyanoacrylate, 2-ethoxyethyl 2-cyanoacrylate, 2-methoxyethyl 2-cyanoacrylate, allyl 2-cyanoacrylate, 2-octyl 2-cyanoacrylate, 2-methoxypropyl 2-cyanoacrylate, 2-propoxyethyl 2-cyanoacrylate, n-octyl 2-cyanoacrylate, and isoamyl cyanoacrylate.

In at least one embodiment, the at least one cyanoacrylate monomer is chosen from those of formula (IV). According to another embodiment, the at least one cyanoacrylate monomer is chosen from C6-C10 alkyl cyanoacrylates.

In another embodiment, the at least one cyanoacrylate monomer is chosen from octyl cyanoacrylates of formula (V) and mixtures thereof:

wherein R′3 is chosen from:

    • —(CH2)7—CH3;
    • —CH(CH3)—(CH2)5—CH3;
    • —CH2—CH(C2H5)—(CH2)3—CH3;
    • —(CH2)5—CH(CH3)—CH3; and
    • —(CH2)4—CH(C2H5)—CH3.

A non-limiting example of a suitable cyanoacrylate monomer that can be used in at least one embodiment of the present disclosure is methylheptyl cyanoacrylate.

The monomers used in accordance with the present disclosure may be covalently bonded to supports such as polymers, oligomers, and dendrimers. The polymers and oligomers may be linear, branched, in comb form, and in block form. The distribution of the monomers of the present disclosure over the polymeric, oligomeric, or dendritic structure may be random, in an end position, or in the form of blocks.

The at least one polymerizable cyanoacrylate monomer is present in the composition in an amount ranging from 0.1% to 99% by weight, or from 1% to 30% by weight relative to the total weight of the cosmetic composition.

The at least one cyanoacrylate monomer of formula (I) according to the present disclosure may be synthesized according to methods described in the art, for example, the cyanoacrylate monomers may be synthesized as disclosed in U.S. Pat. Nos. 3,527,224, 3,591,767, 3,667,472, 3,995,641, 4,035,334, and 4,650,826.

Conditioning Agents

The at least one conditioning agent may be in a form chosen from liquids, semi-solids, and solids, for instance, oils, waxes, and gums.

The at least one conditioning agent according to the present disclosure can be chosen, for example, from:

organic acids, and

oils.

According to one embodiment, the at least one conditioning agent according to the present disclosure may be chosen from organic acids, such as C1-C12 organic acids, comprising at least one group chosen from carboxylic groups and sulfonic groups, and, in at least one embodiment, having a pKa ranging from 0 to 6, such as benzenesulfonic acid, toluenesulfonic acid, acetic acid, formic acid, propionic acid, benzoic acid, mono-, di-, or trichloroacetic acid, salicylic acid, trifluoroacetic acid, citric acid, octanoic acid, heptanoic acid, and hexanoic acid.

In another embodiment, the at least one conditioning agent is chosen from acetic acid, citric acid, and octanoic acid.

When the at least one conditioning agent is chosen from organic acids, the organic acid can be present in the composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the composition, for example, from 0.1% to 15% by weight relative to the total weight of the composition.

According to another embodiment, the at least one conditioning agent may be chosen from oils, such as mineral, organic, and plant oils.

In at least one embodiment, the at least one conditioning agent may be chosen from plant oils, such as triglycerides.

Examples of suitable oils include, but are not limited to, olive oil, castor oil, rapeseed oil, coconut oil, wheatgerm oil, sweet almond oil, avocado oil, polybutene oil, macadamia oil, apricot kernel oil, isononyl isononanoate, safflower oil, candlenut oil, isostearyl malate, jojoba oil, sunflower oil, sesame seed oil, groundnut oil, grapeseed oil, soybean oil, corn oil, hazelnut oil, shea butter, palm oil, beauty-leaf oil, camelina oil, tamanu kernel oil, pentaerythrityl tetraisostearate, tridecyl trimellitate, and lemon oil.

According to another embodiment, the at least one conditioning agent may be chosen from oils such as volatile silicones. Suitable volatile silicones include, but are not limited to, linear and cyclic silicones with a viscosity at room temperature and at atmospheric pressure of less than 8 mm2/s (8 cSt).

The viscosity may be measured by capillary viscometry, for example, using a capillary viscometer, such as Ubbelohde viscometers, at a temperature of 25° C., according to ASTM standard D445-97. The falling-ball method may also be used.

The volatile silicones generally have a boiling point ranging from 60° C. to 260° C., and may be chosen, for instance, from:

(i) cyclic volatile silicones comprising from 3 to 7, for example, from 4 to 5 silicon atoms. They may be chosen, for example, from octamethylcyclotetrasiloxane, such as those sold under the names Volatile Silicone 7207 by Union Carbide and Silbione® 70045 V 2 by Rhodia, decamethylcyclopentasiloxane, such as those sold under the names Volatile Silicone 7158 by Union Carbide, Silbione® 70045 V 5 by Rhodia, and DC245 Fluid by Dow Corning, and mixtures thereof.

The cyclic volatile silicones may also include, for example, cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, such as Volatile Silicone FZ 3109 sold by the company Union Carbide, having the chemical structure:

Non-limiting mention may also be made of mixtures of cyclic silicones with organosilicon compounds, such as the mixture of octamethylcyclotetrasiloxane and tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1,1′-bis[2,2,2′,2′,3,3′-hexakis(trimethylsilyloxy)]neopentane;

(ii) linear volatile silicones comprising from 2 to 9 silicon atoms and having a viscosity of less than or equal to 5 mm2/s at 25° C. A non-limiting example of such silicones is decamethyltetrasiloxane sold, for example, under the name SH 200 by the company Toray Silicone. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 76, pp. 27-32, Todd & Byers “Volatile Silicone Fluids for Cosmetics”.

In at least one embodiment, the at least one conditioning agent is decamethylcyclopentasiloxane, more commonly known as D5.

According to another embodiment, the at least one conditioning agent may be chosen from oils such as fluid silicones.

As used herein, the term “fluid silicone” means a silicone whose dynamic viscosity measured at 25° C. ranges from 0.1 cSt to 1,000,000 cSt, for example, from 1 cSt to 30,000 cSt.

The silicones that may be used in accordance with the present disclosure may be soluble or insoluble in water, and in at least one embodiment, may be chosen from water-insoluble polyorganosiloxanes.

Organopolysiloxanes are defined, for instance, in Walter Noll's “Chemistry and Technology of Silicones” (1968), Academic Press. They may be volatile or non-volatile.

Examples of non-volatile silicones include, but are not limited to, polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, silicone gums, and polyorganosiloxanes modified with organofunctional groups.

The organomodified silicones that can be used in accordance with the present disclosure may be chosen from silicones as defined above and comprising in their structure at least one organofunctional group attached via a hydrocarbon-based group.

Examples of organomodified silicones include, but are not limited to, polyorganosiloxanes comprising:

    • polyethyleneoxy and/or polypropyleneoxy groups optionally comprising C6-C24 alkyl groups, such as the products known as dimethicone copolyol sold by the company Dow Corning under the name DC 1248 and the oils Silwet® L 722, L 7500, L 77, and L 711 by the company Union Carbide, and the (C1-2)alkylmethicone copolyol sold by the company Dow Corning under the name Q2 5200;
    • substituted or unsubstituted amine groups, such as the products sold under the name GP 4 Silicone Fluid and GP 7100 by the company Genesee, and the products sold under the names Q2 8220 and Dow Corning 929 and 939 by the company Dow Corning. The substituted amine groups include, for instance, C1-C4 aminoalkyl groups;
    • thiol groups such as the products sold under the names GP 72 A and GP 71 from Genesee;
    • alkoxylated groups such as the product sold under the name Silicone Copolymer F-755 by SWS Silicones and Abil Wax® 2428, 2434, and 2440 by the company Goldschmidt;
    • hydroxylated groups such as the polyorganosiloxanes comprising a hydroxyalkyl functional group, such as those described in French Patent Application No. 85-16334;
    • acyloxyalkyl groups such as the polyorganosiloxanes described in U.S. Pat. No. 4,957,732;
    • anionic groups of carboxylic acid type, for example, those in the products described in European Patent No. 0 186 507 from the company Chisso Corporation, and of alkylcarboxylic type, such as those present in the product X-22-3701E from the company Shin-Etsu; 2-hydroxyalkyl sulfonate; 2-hydroxyalkyl thiosulfate such as the products sold by the company Goldschmidt under the names Abil® S201 and Abil® S255;
    • hydroxyacylamino groups, such as the polyorganosiloxanes described in European Patent Application No. 0 342 834, and the product Q2-8413 from the company Dow Corning.

In at least one embodiment, the silicone oils in the compositions according to the present disclosure comprise a PDMS (polydimethylsiloxane) volatile oil and a dimethicone or dimethiconol gum. Examples of such mixtures that are already commercially available include, but are not limited to:

D5 and dimethiconol mixtures, for instance, DC 1501 Fluid (Dow Corning),

D5 and dimethicone mixtures, such as DC 1411 Fluid from Dow Corning and SF1214 from Bayer, and

PDMS fluid and dimethiconol mixtures, such as DC 1503 Fluid from Dow Corning.

When the at least one conditioning agent is chosen from oils, it is present in the composition in an amount ranging from 1% to 99.9% by weight relative to the total weight of the composition, for example, from 20% to 95% by weight relative to the total weight of the composition.

Additional Compounds

Fillers

The at least one additional compound can be chosen from fillers, such as mineral and organic fillers of any form, which may be platelet-shaped, spherical, or oblong, irrespective of the crystallographic form (for example, lamellar, cubic, hexagonal, orthorhombic, etc.). Examples of suitable fillers include, but are not limited to talc, mica, silica, silica surface-treated with a hydrophobic agent, kaolin, bentone, polyamide (Nylon®) powder (Orgasol® from Atochem), poly-β-alanine powder, polyethylene powder, tetrafluoroethylene polymer (Teflon®) powders, lauroyllysine, starch, boron nitride, hollow polymer microspheres such as those of polyvinylidene chloride/acrylonitrile, for instance Expancel® (Nobel Industrie) and of acrylic acid copolymers (Polytrap® from the company Dow Corning) and silicone resin microbeads (for example Tospearls® from Toshiba), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, hydroxyapatite, hollow silica microspheres (Silica Beads® from Maprecos), glass microcapsules, ceramic microcapsules, and metal soaps derived from organic carboxylic acids comprising from 8 to 22 carbon atoms, such as from 12 to 18 carbon atoms, for example, zinc stearate, magnesium stearate, lithium stearate, zinc laurate, and magnesium myristate.

In at least one embodiment, the filler may be fumed silica that has optionally undergone a hydrophobic surface treatment. It is possible to chemically modify the surface of silica by chemical reaction generating a reduction in the number of silanol groups present at the surface of the silica. It is also possible to replace silanol groups with hydrophobic groups to obtain a hydrophobic silica. The hydrophobic groups may be chosen, for example, from:

trimethylsiloxyl groups, which may be obtained by treating fumed silica in the presence of hexamethyldisilazane. Silicas that have been thus treated are known as “Silica silylate” according to the CTFA (6th edition, 1995). They are sold, for example, under the references Aerosil R812® and Aerosil R8200 by the company Degussa, and Cab-O—Sil TS-530® by the company Cabot,

dimethylsiloxyl and polydimethylsiloxane groups, which may be obtained by treating fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane. Silicas that have been thus treated are known as “Silica dimethyl silylate” according to the CTFA (6th edition, 1995). They are sold, for example, under the references Aerosil R972® and Aerosil R974©) by the company Degussa, and Cab-O—Sil TS-61 0) and Cab-O—Sil TS-720® by the company Cabot.

The hydrophobic fumed silica may, in at least one embodiment, have a particle size ranging from nanometric to micrometric, for example, ranging from 5 to 200 nm.

Boron nitride may also be used as a filler in accordance with the present disclosure, for instance, the Belsil BNP range from Wacker and CC6098 and CC6004 from Advanced Ceramics.

The particles may be treated by coating or grafting. Mixed mineral/organic particles may thus be obtained and used as fillers in accordance with one embodiment of the present disclosure.

The particles may also be compounds that have been made hydrophilic by chemical coating or grafting using materials such as chitosan, titanium dioxide, silica, and hydrophilic polymers, for example, sulfonic polyesters and polyquaternary ammoniums.

Hydrophobic pulverulent compounds chosen from pulverulent compounds of hydrophobic and hydrophilic nature, may also be used as fillers in accordance with the present disclosure. In the latter case, they are made hydrophobic by chemical coating or grafting with products such as silicones, amino acids, metal soaps, fluoro derivatives, mineral oils, lecithin, isopropyl triisostearyl titanate, polyethylene, collagen and derivatives thereof, and polyacrylates.

Non-limiting examples of such fillers include the polymethylhydrogenosiloxane-coated silica microbeads sold under the trade name Silica SI SB 700 by Miyoshi and the sericite coated with methicone/hydrogenated egg oil sold under the trade name Sericite SNI S100 by Miyoshi.

When the at least one additional compound is chosen from fillers, it may be present in the composition in an amount ranging from 0.01% to 50% by weight, for example, from 0.01% to 30% by weight relative to the total weight of the composition.

Mineral and Organic Bases

The at least one additional compound can also be chosen from mineral and organic bases, such as aqueous ammonia, monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine, alkali metal carbonates and bicarbonates, ammonium carbonates and bicarbonates, organic carbonates such as guanidine carbonate, alkali metal hydroxides such as sodium hydroxide; and in at least one embodiment, monoethanolamine.

When the at least one additional compound is chosen from bases, it may be present in the composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the composition, for example, from 0.01% to 5% by weight relative to the total weight of the composition.

C1-C8 Lower Alcohols

In another embodiment, the at least one additional compound may be chosen from C1-C8 lower alcohols, for example, lower monoalcohols comprising from 1 to 5 carbon atoms, such as ethanol and isopropanol, glycols comprising from 2 to 8 carbon atoms such as propylene glycol, ethylene glycol, 1,3-butylene glycol, and dipropylene glycol, and in at least one embodiment, ethanol.

When the at least one additional compound is chosen from C1-C8 alcohols, it may be present in the composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the composition, for example, from 0.01% to 5% by weight relative to the total weight of the composition.

Nucleophilic Agents

In at least one embodiment, the electrophilic cyanoacrylate monomers of formula (I) are monomers capable of undergoing anionic polymerization in the presence of a nucleophilic agent. As used herein, the term “anionic polymerization” means the mechanism defined in the book “Advanced Organic Chemistry,” Third Edition, by Jerry March, pages 151 to 161.

The nucleophilic agents capable of initiating the anionic polymerization may be chosen from systems known in the art, which are capable of generating a carbanion on contact with a nucleophilic agent, such as the hydroxide ions contained in water at neutral pH. As used herein, the term “carbanion” means the chemical species defined in “Advanced Organic Chemistry,” Third Edition, by Jerry March, page 141.

The nucleophilic agents may be applied separately from the composition of the present disclosure. They may also be mixed with the composition of the present disclosure at the time of use.

The nucleophilic agent may be chosen from molecular compounds, oligomers, dendrimers, and polymers containing nucleophilic functional groups. Non-limiting examples of nucleophilic functional groups include: R2N−, NH2−, Ph3C−, R3C−, PhNH−, pyridine, ArS−, R—C≡C−, RS−, SH−, RO−, R2NH, ArO−, N3−, OH−, ArNH2, NH3, I−, Br−, Cl−, RCOO−, SCN−, ROH, RSH, NCO−, CN−, NO3−, ClO4−, and H2O, wherein Ph is a phenyl group; Ar is an aryl group, and R is chosen from C1-C10 alkyl groups.

Optional Additives

The composition of the present disclosure may also comprise at least one polymerization inhibitors other than organic acids, such as anionic and/or free-radical polymerization inhibitors, so as to increase the stability of the composition over time. Examples of suitable polymerization inhibitors include, but are not limited to: sulfur dioxide, nitric oxide, boron trifluoride, hydroquinone and derivatives thereof such as hydroquinone monoethyl ether, TBHQ, benzoquinone and derivatives thereof such as duroquinone, catechol and derivatives thereof such as t-butylcatechol and methoxycatechol, anisole and derivatives thereof such as methoxyanisole and hydroxyanisole, pyrogallol and derivatives thereof, p-methoxyphenol, hydroxybutyltoluene, alkyl sulfates, alkyl sulfites, alkyl sulfones, alkyl sulfoxides, alkyl sulfides, mercaptans, 3-sulfonene, and mixtures thereof. In at least one embodiment, the alkyl groups may be chosen from alkyl groups comprising from 1 to 6 carbon atoms.

The at least one polymerization inhibitor may be present in the cosmetic composition in an amount ranging from 10 ppm to 5% by weight, for example, from 10 ppm to 0.5% by weight relative to the total weight of the composition.

The composition of the present disclosure may also comprise at least one organic UV-screening agent (systems for screening out UV radiation) chosen from water-soluble or liposoluble, silicone or non-silicone screening agents.

The organic screening agents can be chosen, for example, from dibenzoylmethane derivatives; anthranilates; cinnamic derivatives; salicylic derivatives; camphor derivatives; benzophenone derivatives; diphenylacrylate derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bis-benzazolyl derivatives described in European Patent No. 0 669 323 and U.S. Pat. No. 2,463,264; p-aminobenzoic acid (PABA) derivatives; benzoxazole derivatives described in European Patent Application Nos. 0 832 642, 1 027 883, and 1 300 137 and German Patent Application No. 101 62 844; screening polymers and screening silicones such as those described in International Patent Application Publication No. WO 93/04665; α-alkylstyrene-based dimers, such as those described in German Patent Application No. 198 55 649; 4,4-diarylbutadienes such as those described in European Patent Application Nos. 0 967 200, 1 008 586, 1 133 980, and EP 133 981, and German Patent Application Nos. 197 46 654 and 197 55 649, and mixtures thereof.

Further examples of organic UV-screening agents include, but are not limited to, those denoted hereinbelow under their INCI name:

para-Aminobenzoic Acid Derivatives:

PABA,

Ethyl PABA,

Ethyl dihydroxypropyl PABA,

Ethylhexyl dimethyl PABA sold, for instance, under the name Escalol 507 by ISP,

Glyceryl PABA, and

PEG-25 PABA sold, for example, under the name Uvinul P25 by BASF.

Cinnamic Derivatives:

Ethylhexyl methoxycinnamate sold, for instance, under the trade name Parsol MCX by Hoffmann LaRoche,

Isopropyl methoxycinnamate,

Isoamyl methoxycinnamate sold, for example, under the trade name Neo Heliopan E 1000 by Haarmann and Reimer,

Cinoxate,

DEA methoxycinnamate,

Diisopropyl methylcinnamate, and

Glyceryl ethylhexanoate dimethoxycinnamate.

Dibenzoylmethane Derivatives:

Butylmethoxydibenzoylmethane sold, for instance, under the trade name Parsol 1789 by Hoffmann LaRoche, and

Isopropyldibenzoylmethane sold, for example, under the trade name Eusolex 8020 by Merck.

Salicylic Derivatives:

Homosalate sold, for instance, under the name Eusolex HMS by Rona/EM Industries,

Ethylhexyl salicylate sold, for example, under the name Neo Heliopan OS by Haarmann and Reimer,

Dipropylene glycol salicylate sold, for instance, under the name Dipsal by Scher, and

TEA salicylate sold, for example, under the name Neo Heliopan TS by Haarmann and Reimer.

Diphenylacrylate Derivatives:

Octocrylene sold, for instance, under the trade name Uvinul N539 by BASF, and

Etocrylene sold, for example, under the trade name Uvinul N35 by BASF.

Benzophenone Derivatives:

Benzophenone-1 sold, for instance, under the trade name Uvinul 400 by BASF,

Benzophenone-2 sold, for example, under the trade name Uvinul D50 by BASF,

Benzophenone-3 or Oxybenzone sold, for instance, under the trade name Uvinul M40 by BASF,

Benzophenone-4 sold, for example, under the trade name Uvinul MS40 by BASF,

Benzophenone-5,

Benzophenone-6 sold, for instance, under the trade name Helisorb 11 by Norquay,

Benzophenone-8 sold, for example, under the trade name Spectra-Sorb UV-24 by American Cyanamid,

Benzophenone-9 sold, for instance, under the trade name Uvinul DS-49 by BASF,

Benzophenone-12, and

n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate.

Benzylidenecamphor Derivatives:

3-Benzylidenecamphor sold, for example, under the name Mexoryl SD by Chimex,

4-Methylbenzylidenecamphor sold, for instance, under the name Eusolex 6300 by Merck,

Benzylidenecamphorsulfonic acid sold, for example, under the name Mexoryl SL by Chimex,

Camphor benzalkonium methosulfate sold, for instance, under the name Mexoryl SO by Chimex,

Terephthalylidenedicamphorsulfonic acid sold, for example, under the name Mexoryl SX by Chimex, and

Polyacrylamidomethylbenzylidenecamphor sold, for instance, under the name Mexoryl SW by Chimex.

Phenylbenzimidazole Derivatives:

Phenylbenzimidazolesulfonic acid sold, for example, under the trade name Eusolex 232 by Merck, and

Disodium phenyl dibenzimidazole tetrasulfonate sold, for instance, under the trade name Neo Heliopan AP by Haarmann and Reimer.

Phenylbenzotriazole Derivatives:

Drometrizole trisiloxane sold, for example, under the name Silatrizole by Rhodia Chimie, and

Methylenebis(benzotriazolyl)tetramethylbutylphenol sold, for instance, in solid form under the trade name Mixxim BB/100 by Fairmount Chemical, or in micronized form as an aqueous dispersion under the trade name Tinosorb M by Ciba Specialty Chemicals.

Triazine Derivatives:

Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold, for example, under the trade name Tinosorb S by Ciba Geigy,

Ethylhexyltriazone sold, for instance, under the trade name Uvinul T150 by BASF,

Diethylhexylbutamidotriazone sold, for example, under the trade name Uvasorb HEB by Sigma 3V, and

2,4,6-tris(diisobutyl 4′-aminobenzalmalonate)-s-triazine.

Anthranilate Derivatives:

Menthyl anthranilate sold, for instance, under the trade name Neo Heliopan MA by Haarmann and Reimer.

Imidazoline Derivatives:

Ethylhexyldimethoxybenzylidenedioxoimidazoline propionate.

Benzalmalonate Derivatives:

Polyorganosiloxane containing benzalmalonate functions, for instance, Polysilicone-15, sold under the trade name Parsol SLX by Hoffmann LaRoche.

4,4-Diarvibutadiene Derivatives:

1,1-Dicarboxy(2,2′-dimethylpropyl)-4,4-diphenylbutadiene.

Benzoxazole Derivatives:

2,4-bis[5-(1-dimethylpropyl)benzoxazol-2-yl(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine sold, for example, under the name Uvasorb K2A by Sigma 3V,

and mixtures thereof.

Non-limiting examples of liposoluble (or lipophilic) organic UV-screening agents that are suitable for use in accordance with the present disclosure include:

ethylhexyl methoxycinnamate,

butylmethoxydibenzoylmethane,

Homosalate,

ethylhexyl salicylate,

Octocrylene,

Benzophenone-3,

n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate,

4-methylbenzylidenecamphor,

ethylhexyl triazone,

bis-ethylhexyloxyphenol methoxyphenyl triazine,

diethylhexyl butamido triazone,

drometrizole trisiloxane,

Polysilicone-15,

1,1-dicarboxy(2,2′-dimethylpropyl)-4,4-diphenylbutadiene, and

2,4-bis[5-1 (dimethylpropyl)benzoxazol-2-yl(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine.

Suitable water-soluble (or hydrophilic) organic UV-screening agents include, by way of non-limiting example:

PABA,

PEG-25 PABA,

benzylidenecamphorsulfonic acid,

camphorbenzalkonium methosulfate,

terephthalylidenedicamphorsulfonic acid,

phenylbenzimidazolesulfonic acid,

disodium phenyl dibenzimidazole tetrasulfonate,

Benzophenone-4, and

Benzophenone-5.

The composition used in accordance with the present disclosure may also comprise at least one polymer.

As used herein, the term “polymer” means any natural or synthetic polymer that may be used in cosmetics, for instance, polymers obtained by a process chosen from free-radical polymerization, anionic polymerization, polycondensation, and ring opening. These polymers may be chosen from linear, branched, and star polymers.

The composition according to the present disclosure may also comprise at least one reducing agent chosen from thio acids and salts thereof (e.g., thioglycolic acid, thiosulfate, cysteine, and cysteamine), alkali metal sulfites, alkaline-earth metal sulfites, reducing sugars such as glucose, vitamin C and derivatives thereof, sulfovinic acid derivatives, and phosphines.

The composition according to the present disclosure may also comprise at least one coloring agent chosen from linear or aromatic (heterocyclic or non-heterocyclic) conjugated structures. Examples of such coloring agents include, but are not limited to, nitrobenzene dyes, aromatic dyes, aminobenzene dyes, azo dyes, anthraquinone dyes, aromatic diamines, aminophenols, phenols, naphthols, porphyrins, tetraphenylporphyrins, metalloporphyrins, phthalocyanins, carotenoids, flavonoids, and fluorescent molecules (e.g, fluorescein, rhodamine, coumarin, etc.).

The medium of the composition according to the present disclosure may be chosen from water, at least one liquid organic solvents, and mixtures of water and at least one liquid organic solvent.

In at least one embodiment, the support for the composition according to the present disclosure can be anhydrous and non-hygroscopic.

As used herein, the term “anhydrous support” means a support containing less than 1% water.

In one embodiment, the liquid organic solvents may be chosen from compounds other than the cyanoacrylate monomers according to the present disclosure that are liquid at a temperature of 25° C. and at 105 Pa (760 mmHg).

In another embodiment, the support may comprise the at least one conditioning agent as mentioned above.

Examples of suitable liquid organic solvents that may be used include, but are not limited to:

aromatic alcohols such as benzyl alcohol;

liquid fatty alcohols comprising at least 12 carbon atoms;

liquid paraffins and liquid alkanes, such as C5-C10 alkanes;

liquid fatty acids comprising at least 12 carbon atoms, liquid fatty amides, and fatty esters, for instance, fatty alkyl benzoates and salicylates.

According to one embodiment, the support for the composition of the present disclosure may be in the form of capsules in dispersion, either in an anhydrous medium as defined above, in an aqueous medium, or in the form of an emulsion.

According to another embodiment, the support for the composition of the present disclosure may be in the form of an emulsion comprising an aqueous phase and an organic phase in which the cyanoacrylate monomer is stabilized.

The cosmetic composition of the present disclosure may also comprise at least one common cosmetic additive chosen, by way of non-limiting example, from reducing agents, oxidizing agents, sequestrants, polymeric or non-polymeric thickeners, moisturizers, emollients, plasticizers, optical brighteners, clays, colloidal minerals, colloidal metals, semi-conductive particles of “quantum well” type based on metals or on silicon, photochromic or thermochromic compounds, nacreous agents, fragrances, peptizers, preserving agents, proteins, vitamins, anti-dandruff agents, oxyethylenated or non-oxyethylenated waxes, anionic, cationic, or amphoteric fixing or non-fixing polymers, and anionic, cationic, amphoteric, and nonionic surfactants.

The formulations may be in a galenical form chosen from lotions, aerosol mousses, hair conditioners, shampoos, gels, and waxes. The compositions may be contained in a container such as pump-dispenser bottles and aerosol sprays. After application to the hair, the compositions of the present disclosure may be rinsed out or left on.

When the composition is contained in an aerosol, it may further comprise at least one propellant. The at least one propellant may comprise at least one compressed or liquefied gas conventionally used for the preparation of aerosol compositions. Examples of such gases include, but are not limited to, air, carbon dioxide, compressed nitrogen, soluble gases such as dimethyl ether, halogenated hydrocarbons (for example, fluorohydrocarbons), non-halogenated hydrocarbons (for instance, butane, propane, and isobutane), and mixtures thereof.

Processes

Disclosed herein is a process for treating keratin fibers, for instance, human keratin fibers such as the hair, wherein a composition of the present disclosure is applied to the fibers in the presence of at least one nucleophilic agent.

According to one embodiment, the at least one nucleophilic agent capable of initiating the polymerization of the at least one cyanoacrylate monomer may be applied to the keratin fibers before application of the cosmetic composition of the present disclosure. The at least one nucleophilic agent may be used pure, as a solution, in the form of an emulsion, or it may be encapsulated. It may also be added to the anhydrous composition at the time of use just before application to the keratin fibers.

In one embodiment, the at least one nucleophilic agent is water. This water may be provided, for example, by premoistening the keratin fibers. In another embodiment, water may also be added directly to the composition before application.

According to a further embodiment, it is possible to modify the polymerization kinetics by premoistening the fiber with an aqueous solution whose pH has been adjusted using an agent chosen from bases, acids, and acid/base mixtures. The acid and/or the base may be mineral or organic.

It is also possible to perform multiple applications of the composition of the present disclosure in order to obtain a superposition of coats to achieve specific properties for the deposit in terms of chemical nature, mechanical strength, thickness, appearance, and/or feel.

In order to improve, inter alia, the adhesion of the poly(cyanoacrylate) formed in situ, the fiber may be pretreated with any type of polymer.

To modify the anionic polymerization kinetics, the nucleophilicity of the fiber may also be increased by chemical transformation of the keratin fibers. For example, the disulfide bridges, of which keratin is partly composed, may be reduced to thiols before applying the composition of the present disclosure. Examples of reducing agents for the disulfide bridges of which keratin is partly composed, include, but are not limited to: anhydrous sodium thiosulfate, powdered sodium metabisulfite, thiourea, ammonium sulfite, thioglycolic acid, thiolactic acid, ammonium thiolactate, glyceryl monothioglycolate, ammonium thioglycolate, thioglycerol, 2,5-dihydroxybenzoic acid, diammonium dithioglycolate, strontium thioglycolate, calcium thioglycolate, zinc formosulfoxylate, isooctyl thioglycolate, DL-cysteine, and monoethanolamine thioglycolate.

Also disclosed herein is a process for improving the color of artificially dyed keratin fibers, wherein at least one cosmetic composition of the present disclosure is applied before and/or after dyeing the said fibers, in the presence of at least one nucleophilic agent as defined above; wherein the at least one nucleophilic agent is present in the cosmetic composition or contained separately.

According to one embodiment, when the composition according to the present disclosure is applied to the fibers after dyeing the hair, the process can make it possible to protect the color from successive washes and to improve the cosmetic properties following these washes.

This process may be performed in a single stage or in two stages. When the process for protecting the color is performed in two stages, the first stage comprises applying a composition containing at least one nucleophilic agent to the fibers after the fibers have been dyed and wrung dry. The fibers may then be optionally dried. The second stage comprises applying a cosmetic composition as defined above and not containing a nucleophilic agent to the fibers.

It one embodiment, prior to applying the composition containing at least one nucleophilic agent, a composition containing at least one cosmetic additive may be applied to the fibers.

In another embodiment, the fibers may be rinsed and/or washed with shampoo before the application of the composition containing at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound as defined herein.

In yet another embodiment, the process may further comprise totally or partially drying the keratin fibers with a hairdryer and optionally a final shampooing.

According to a further embodiment, the process for protecting the color of the keratin fibers may comprise a step of heating the cosmetic composition to a desired temperature, and then applying the heated composition directly to the keratin fibers. The temperature may range, for example, from 60 to 120° C.

According to another embodiment, the process for treating the color of the keratin fibers may comprise a step of heating the keratin fibers after application of the cosmetic composition.

The heating of the keratin fibers may be performed, for example, using an iron, a liquid water/steam mixture, and/or by using a heating hood.

The heating iron can be chosen from those conventionally used in the field of haircare, for example, crimping irons and smoothing irons. Other examples of irons that are useful in accordance with the present disclosure include flat or round irons described in U.S. Pat. Nos. 4,103,145, 4,308,878, 5,983,903, 5,957,140, and 5,494,058. The iron may be applied by successive separate touches of a few seconds, or by gradually moving or sliding it along the locks. In at least one embodiment, there may be a pause between the application of the color-protecting composition and the application of the heating iron to the keratin fibers. Such a pause can range, for example, from 30 seconds to 60 minutes, such as from 1 to 30 minutes.

The liquid water/steam mixture which may be used in accordance with the present disclosure may have a temperature of at least 35° C.

The liquid water/steam mixture may constitute a mist and may also comprise at least one other gas such as oxygen and nitrogen, mixtures of gases such as air, and other vaporizable compounds.

In at least one embodiment, the temperature of the liquid water/steam mixture may be greater than or equal to 40° C., for example, it may range from 40° C. to 75° C.

In another embodiment, the liquid water/steam mixture can be placed in contact with the fiber for a time ranging from 1 second to 1 hour, for instance, from 5 minutes to 15 minutes. The application of the mixture may be repeated several times on the same fiber, each operation being performed for a time as indicated above. In at least one embodiment, the cosmetic composition is first applied to the hair and these locks thus impregnated are then subjected to the action of the liquid water/steam mixture under the conditions mentioned above, and the locks thus treated are then cooled, for example by sending over or through them a stream of cold or via ambient temperature air.

The liquid water/steam mixture used in accordance with the present disclosure may be produced using any apparatus known in the art and intended for this purpose. According to the present disclosure, the liquid water/steam mixture is diffused onto the keratin fibers using an apparatus comprising at least one steam generator directly connected to a hood. A non-limiting example of this type of apparatus is that sold under the name Micromist® by the company Takara Belmont.

The processes mentioned above may be performed on the actual day of dyeing or at least one day (for instance, from 1 to 60 days) after dyeing.

Also disclosed herein is also a process for treating keratin fibers to unify the color of the fibers after dyeing them. This process comprises washing the fibers, wringing the fibers dry, dyeing the fibers, and then applying to the fibers a cosmetic composition of the present disclosure comprising at least one nucleophilic agent.

According to one embodiment, the process for treating the keratin fibers to unify the color of the fibers after dyeing them may be performed in two stages. The first stage comprises washing the fibers, wringing the fibers dry, dyeing the fibers, applying to the fibers a composition comprising at least one nucleophilic agent, and optionally drying the fibers. The second stage comprises applying to the fibers a cosmetic composition of the present disclosure which does not comprise any nucleophilic agent.

According to at least one embodiment, a composition containing at least one cosmetic additive may be applied to the fibers prior to the application of the composition containing at least one nucleophilic agent.

The processes according to the present disclosure may further comprise totally or partially drying the keratin fibers with a hairdryer and optionally a final shampooing.

Further disclosed herein is a dyeing process comprising applying a dye composition (A) to human keratin fibers, such as the hair, this composition possibly containing at least one direct dye (A1), or at least one direct dye and one oxidizing agent, leading to a lightening direct dye composition (A2), or at least one oxidation dyeing base and optionally at least one coupler (A3), or alternatively at least one oxidation dyeing base and optionally at least one coupler, and at least one direct dye (A4), for a time that is sufficient to develop the color, and following or preceding this application by the application of a composition (B) containing the cosmetic composition of the present disclosure comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral and organic bases, and C1-C8 lower alcohols in the presence of at least one nucleophilic agent as defined above; wherein the nucleophilic agent may be present in the cosmetic composition or may be contained separately in a composition (C).

The application of the dye composition (A) may be followed by rinsing and/or drying of the keratin fibers.

The application of composition (B) may be followed by rinsing and/or drying of the keratin fibers. Composition (B) may be preheated under the same conditions defined above. The application of composition (B) may be followed by heating of the keratin fibers under the same conditions defined above.

Composition (B) may be applied immediately after dyeing, or after an interval. As used herein, the term “after an interval” means an application is performed a few hours, one day or several days (for example, from 1 to 60 days) after dyeing. In at least one embodiment, composition (B) may be applied immediately after dyeing the keratin fibers; the applications of the composition may be repeated between two colorations.

The nature and concentration of the dyes present in the dye composition (A) is not critical and may be chosen in accordance with the general knowledge in the art.

As used herein, the term “dyeing” means any dyeing process that uses dyes other than pigments, which are defined by any organic and/or mineral species whose solubility in water is less than 0.01%, for example, less than 0.0001% at 20° C., and which has an absorption between 350 and 700 nm, and in one embodiment, an absorption with a maximum.

In the case of lightening direct dyeing, the dye compositions (A2) result from the mixing at the time of use of a dye composition containing at least one direct dye and of a composition (A5) containing an oxidizing agent.

In the case of oxidation dyeing, the dye compositions (A3) and (A4) result from the mixing at the time of use of a dye composition containing at least one oxidation base and optionally at least one coupler and/or at least one direct dye and of a composition (A5) containing an oxidizing agent.

The direct dyes may be chosen from compounds that absorb light radiation in the visible range (400-750 nm). They may further be chosen from nonionic, anionic, and cationic direct dyes.

In at least one embodiment, the direct dyes may be chosen from nitrobenzene dyes, azo dyes, anthraquinone dyes, naphthoquinone dyes, benzoquinone dyes, phenothiazine dyes, indigoid dyes, xanthene dyes, phenanthridine dyes, phthalocyanin dyes, triarylmethane-based dyes, and mixtures thereof.

Examples of nitrobenzene dyes include but are not limited to, red and orange compounds, such as 1-hydroxy-3-nitro-4-N-(γ-hydroxypropyl)aminobenzene, N-(β-hydroxy-ethyl)amino-3-nitro-4-aminobenzene, 1-amino-3-methyl-4-N-(β-hydroxyethyl)amino-6-nitro-benzene, 1-hydroxy-3-nitro-4-N-(β-hydroxyethyl)aminobenzene, 1,4-diamino-2-nitrobenzene, 1-amino-2-nitro-4-methylaminobenzene, N-(β-hydroxyethyl)-2-nitro-para-phenylenediamine, 1-amino-2-nitro-4-(β-hydroxyethyl)amino-5-chlorobenzene, 2-nitro-4-aminodiphenylamine, 1-amino-3-nitro-6-hydroxybenzene, 1-(β-aminoethyl)amino-2-nitro-4-(β-hydroxyethyloxy)benzene, 1-(β,γ-dihydroxypropyl)oxy-3-nitro-4-(β-hydroxyethyl)amino-benzene, 1-hydroxy-3-nitro-4-aminobenzene, 1-hydroxy-2-amino-4,6-dinitrobenzene, 1-methoxy-3-nitro-4-(β-hydroxyethyl)aminobenzene, 2-nitro-4′-hydroxydiphenylamine, 1-amino-2-nitro-4-hydroxy-5-methylbenzene, and mixtures thereof.

The nitrobenzene direct dyes may also be chosen from yellow and green-yellow dyes, for instance, 1-β-hydroxyethyloxy-3-methylamino-4-nitrobenzene, 1-methylamino-2-nitro-5-(β,γ-dihydroxypropyl)oxybenzene, 1-(β-hydroxyethyl)amino-2-methoxy-4-nitrobenzene, 1-(β-aminoethyl)amino-2-nitro-5-methoxybenzene, 1,3-bis(β-hydroxyethyl)amino-4-nitro-6-chlorobenzene, 1-amino-2-nitro-6-methylbenzene, 1-(β-hydroxyethyl)amino-2-hydroxy-4-nitrobenzene, N-(β-hydroxyethyl)-2-nitro-4-trifluoromethylaniline, 4-(D-hydroxyethyl)amino-3-nitrobenzenesulfonic acid, 4-ethylamino-3-nitrobenzoic acid, 4-(β-hydroxyethyl)amino-3-nitrochlorobenzene, 4-(β-hydroxyethyl)amino-3-nitromethylbenzene, 4-(β,γ-dihydroxypropyl)amino-3-nitrotrifluoro-methylbenzene, 1-(β-ureidoethyl)amino-4-nitrobenzene, 1,3-diamino-4-nitrobenzene, 1-hydroxy-2-amino-5-nitrobenzene, 1-amino-2-[tris(hydroxymethyl)methyl]amino-5-nitrobenzene, 1-(β-hydroxyethyl)amino-2-nitrobenzene, and 4-(β-hydroxyethyl)amino-3-nitrobenzamide.

Blue and violet nitrobenzene dyes may also be used, for instance, 1-(β-hydroxyethyl)amino-4-N,N-bis(β-hydroxyethyl)amino-2-nitrobenzene, 1-(γ-hydroxy-propyl)amino-4-N,N-bis(β-hydroxyethyl)amino-2-nitrobenzene, 1-(β-hydroxyethyl)amino-4-(N-methyl, N-β-hydroxyethyl)amino-2-nitrobenzene, 1-(β-hydroxyethyl)amino-4-(N-ethyl, N-β-hydroxyethyl)amino-2-nitrobenzene, 1-(β,γ-dihydroxypropyl)amino-4-(N-ethyl, N-β-hydroxyethyl)amino-2-nitrobenzene, and 2-nitro-para-phenylenediamines of the following formula:

wherein:

    • R6 is chosen from C1-C4 alkyl radicals, β-hydroxyethyl radicals, β-hydroxypropyl radicals, and γ-hydroxypropyl radicals;
    • R5 and R7, which may be identical or different, are chosen from β-hydroxyethyl radicals, β-hydroxypropyl radicals, γ-hydroxypropyl radicals, and β,γ-dihydroxypropyl radicals, wherein at least one of the radicals R6, R7, or R5 is a γ-hydroxypropyl radical and R6 and R7 are not simultaneously a β-hydroxyethyl radical when R5 is a γ-hydroxypropyl radical, such as those described in French Patent No. 2 692 572.

As used herein in, it is to be understood that azo dyes are compounds comprising in their structure at least one —N═N— sequence not included in a ring; methine dyes are compounds comprising in their structure at least one —C═C— sequence not included in a ring; and azomethine dyes are compounds comprising in their structure at least one —C═N— sequence not included in a ring.

The triarylmethane-based dyes comprise in their structure at least one sequence of formula:

wherein A is chosen from oxygen and nitrogen.

The xanthene dyes comprise in their structure at least one sequence of formula:

The phenanthridine dyes comprise in their structure at least one sequence of formula:

The phthalocyanin dyes comprise in their structure at least one sequence of formula:

The phenothiazine dyes comprise in their structure at least one sequence of formula:

The direct dyes may also be chosen from basic dyes such as those listed in the Color Index, 3rd edition, for example those listed under the names Basic Brown 16, Basic Brown 17, Basic Yellow 57, Basic Red 76, Basic Violet 10, Basic Blue 26, and Basic Blue 99; acidic direct dyes listed in the Color Index, 3rd edition, under the names Acid Orange 7, Acid Orange 24, Acid Yellow 36, Acid Red 33, Acid Red 184, Acid Black 2, Acid Violet 43, and Acid Blue 62; and cationic direct dyes such as those described in International Patent Application Publication Nos. WO 95/01772 and WO 95/15144 and European Patent Application No. 0 714 954, the contents of which are incorporated herein in their entireties, such as Basic Red 51, Basic Orange 31, and Basic Yellow 87.

The direct dyes may also be chosen from colored polymers as described in French Patent Application Nos. 2 361 447, 2 456 764, 2 457 306, U.S. Pat. Nos. 3,567,678, 4,381,260, 4,533,484, 4,871,371, 4,911,731, 4,921,589, 5,310,887, 5,637,637, 5,951,718, 6,194,534, 6,342,618, and 6,653,390, European Patent Application Nos. 0 747 036 and 0 852 943, and U.S. Patent Application Publication Nos. 2002/0006977 and 2003/0221587.

The direct dyes may also be chosen from hydrophobic direct dyes whose logP is greater than 2, as described in French Patent Application Nos. 2 874 177 and 2 874 178, the value of the logP conventionally representing the partition coefficient of the dye between octanol and water.

When present, the at least one direct dye may be present in the composition in an amount ranging from 0.0005% to 12% by weight relative to the total weight of the dye composition, for example, from 0.005% to 6% by weight approximately relative to the total weight of thecomposition.

The oxidation bases may be chosen from oxidation bases conventionally used in oxidation dyeing, for example, para-phenylenediamines, bis(phenyl)alkylene-diamines, para-aminophenols, ortho-aminophenols, and heterocyclic bases.

Examples of para-phenylenediamines include, but are not limited to, para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, N,N-diethyl-4-amino-3-methylaniline, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 4N,N-bis(β-hydroxyethyl)amino-2-methylaniline, 4N,N-bis(β-hydroxy-ethyl)amino-2-chloroaniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N-ethyl-N-(β-hydroxyethyl)-para-phenylenediamine, N-(β,γ-dihydroxypropyl)-para-phenylenediamine, N-(4′-aminophenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetyl-aminoethyloxy-para-phenylenediamine, N-(β-methoxyethyl)-para-phenylenediamine, and acid addition salts thereof.

In at least one embodiment, the para-phenylenediamines may be chosen from para-phenylenediamine, para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2-β-hydroxyethyl-para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine, 2-β-acetylaminoethyloxy-para-phenylenediamine, and the acid addition salts thereof.

Non-limiting examples of bis(phenyl)alkylenediamines include N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(4-methyl-aminophenyl)tetramethylenediamine, N,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)-ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and the acid addition salts thereof.

Suitable para-aminophenols may be chosen, by way of non-limiting example, from para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(β-hydroxyethylaminomethyl)phenol, 4-amino-2-fluorophenol, and the acid addition salts thereof.

Examples of ortho-aminophenols include, but are not limited to, 2-amino-phenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the acid addition salts thereof.

Suitable heterocyclic bases include, by way of non-limiting example, pyridine derivatives, pyrimidine derivatives, and pyrazole derivatives.

Non-limiting examples of pyridine derivatives include the compounds described, for example, in British Patent Nos. 1 026 978 and 1 153 196, such as 2,5-di-aminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(β-methoxyethyl)amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and the acid addition salts thereof.

Examples of pyrimidine derivatives include, but are not limited to, those described in German Patent No. 2 359 399; Japanese Patent Application No. 88-169 571; Japanese Patent No. 05-163 124; European Patent No. 0 770 375, and International Patent Application Publication No. WO 96/15765, such as 2,4,5,6-tetraminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, and 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in French Patent Application No. 2 750 048, such as pyrazolo[1,5-a]-pyrimidine-3,7-diamine; 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; pyrazolo[1,5-a]pyrimidine-3,5-diamine; 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine; 3-aminopyrazolo[1,5-a]pyrimidin-7-ol; 3-aminopyrazolo[1,5-a]pyrimidin-5-ol; 2-(3-amino-pyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)(2-hydroxyethyl)amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 3-amino-5-methyl-7-imidazolylpropylaminopyrazolo[1,5-a]pyrimidine, the acid addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists.

Suitable pyrazole derivatives include, for example, the compounds described in patents German Patent Nos. 3 843 892 and 4 133 957, International Patent Application Publication Nos. WO 94/08969 and WO 94/08970, French Patent Application No. 2 733 749, and German Patent Application No. 195 43 988, such as 4,5-diamino-1-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydra-zinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-amino-5-(2′-aminoethyl)amino-1,3-dimethyl-pyrazole, 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole, 3,5-diamino-4-(β-hydroxyethyl)amino-1-methylpyrazole, the acid addition salts thereof.

When present, the at least one oxidation base may be present in the composition in an amount ranging from 0.0005% to 12% by weight relative to the total weight of the dye composition, for example, from 0.005% to 6% by weight relative to the total weight of the composition.

The oxidation dye compositions in accordance with the present disclosure may also comprise at least one coupler and/or at least one direct dye, to modify the shades and/or to enrich them with tints.

The at least one coupler that may be used in the oxidation dye compositions in accordance with the present disclosure may be chosen from couplers conventionally used in oxidation dyeing, for example, meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthols, and heterocyclic couplers, for instance, indole derivatives, indoline derivatives, pyridine derivatives, indazole derivatives, pyrazolo[1,5-b]-1,2,4-triazole derivatives, pyrazolo[3,2-c]-1,2,4-triazole derivatives, benzimidazole derivatives, benzothiazole derivatives, benzoxazole derivatives, 1,3-benzodioxole derivatives, pyrazolones, and the acid addition salts thereof.

In at least one embodiment, the at least one coupler may be chosen from 2-methyl-5-aminophenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene, 2,4-diamino-1-(β-hydroxyethyloxy)benzene, 2-amino-4-(β-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, x-naphthol, 2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methyl-indole, 6-hydroxyindoline, 6-hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxy-pyridine, 1-N(β-hydroxyethyl)amino-3,4-methylenedioxy-benzene, 2,6-bis(β-hydroxy-ethyleneamino)toluene, 2,6-dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, and the acid addition salts thereof.

When present, the at least one coupler may be present in the composition in an amount ranging from 0.0001% to 10% by weight relative to the total weight of the dye composition, for example, from 0.005% to 5% by weight relative to the total weight of the dye composition.

The dye composition in accordance with the present disclosure may also contain at least one adjuvant conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric, and zwitterionic surfactants and mixtures thereof; anionic, cationic, nonionic, amphoteric, and zwitterionic polymers and mixtures thereof; mineral and organic thickeners; antioxidants; penetrants; sequestrants; fragrances; buffers; dispersants; conditioning agents, for instance, silicones; film-forming agents; preserving agents; and opacifiers.

It is to be understood that a person skilled in the art will take care to select the at least one optional additional compound such that the beneficial properties intrinsically associated with the oxidation dye composition in accordance with the present disclosure are not, or are not substantially, adversely affected by the envisaged addition.

The dye composition according to the present disclosure may be in various forms, for instance, liquids, creams, and gels, or in any other form that is suitable for dyeing keratin fibers, such as human hair.

The nature of the oxidizing agent used in the lightening direct dyeing operation (direct dyeing with an oxidizing agent) or in the oxidation dyeing operation is not critical and may be chosen in accordance with the general knowledge in the art.

In at least one embodiment, the at least one oxidizing agent may be chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, ferricyanides, and persalts such as perborates and persulfates. Redox enzymes such as laccases, peroxidases, and two-electron oxidoreductases (such as uricase) may also be used as oxidizing agents, where appropriate in the presence of the respective donor or cofactor thereof.

The compositions according to the present disclosure may be of variable viscosity. They may be applied in successive drops and then massaged with the fingers, with an optional step of combing, or they may be applied by brush, for example, using a brush board to obtain good distribution of the composition along the length of the fibers.

When the composition of the present disclosure is applied after dyeing, the color-protecting effect of the coating may lead to more uniform protection of the color when the application is performed by brush. Thus, in at least one embodiment, the composition of the present disclosure is applied by brush.

Further disclosed herein is a multi-component coloring agent or kit comprising at least one first component comprising a direct dye composition (A1) as defined above and at least one second component comprising a composition (B) containing the cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral and organic bases, and C1-C8 lower alcohols, as defined above and optionally a composition (D) containing at least one nucleophilic agent.

Still further disclosed herein is a multi-component coloring agent or kit comprising at least one first component comprising a dye composition, such as a composition that may comprise at least one direct dye, or a composition comprising at least one oxidation dyeing base and optionally at least one coupler (A3), or alternatively a composition comprising at least one oxidation dyeing base and optionally at least one coupler, and at least one direct dye (A4), at least one second component comprising a composition (B) comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral and organic bases, and C1-C8 lower alcohols, as defined above, at least one third component comprising a composition (C) comprising at least one oxidizing agent; and optionally at least one fourth component comprising a composition (D) comprising at least one nucleophilic agent.

Other than in the examples, or where otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the present disclosure. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should be construed in light of the number of significant digits and ordinary rounding approaches.

Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the disclosure are approximations, unless otherwise indicated the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective testing measurements.

By way of non-limiting illustration, concrete examples of certain embodiments of the present disclosure are given below.

EXAMPLES

Dyes Tested

A series of natural or permanent-waved 1-g locks were dyed using the following commercial products:

oxidation dyeing:

    • Majirouge 6.66
    • Majirel 7.1

dyeing in locks

    • Maji Contrast, of coppery-red shade

direct dyeing

    • Color Pulse Rouge Pulse
    • Renovative, ash-chestnut and golden light chestnut
    • Expression, of coppery shade
    • Dedicace, of auburn chestnut shade
      A. Tests of Color Protection and of the Cosmetic Properties after Successive Washing

Two identical locks were prepared for each type of dyeing.

One lock was shampooed and the other was treated with the compositions of the present disclosure and then received the same number of shampoo washes.

The color of the locks was subjected to examination by a panel of experts. Colorimetric measurements were also taken, which confirmed the visual evaluations.

Example 1 Dyeing with Coppery-Red Maji Contrast

The following composition was prepared:

α,ω-Dihydroxylated polydimethylsiloxane/cyclo- 45 g pentadimethylsiloxane (14.7/85.3) sold by Dow Corning under the name DC 1501 Fluid Cyclopentadimethylsiloxane sold by Dow Corning under the 44.75 g name DC245 Fluid Acetic acid 0.25 g Methylheptyl cyanoacrylate from Chemence 10 g

0.25 g of this composition was applied by brush to a lock of 1 g of grey hair dyed beforehand with coppery-red Maji Contrast. The lock was dried under a hood for 30 minutes and then combed. At this stage, the lock may be subjected to a final shampooing. The hair felt soft and tangle-free.

After shampooing 15 times, the color of the lock dyed and then treated according to the present disclosure was markedly more vivid than that of the lock dyed identically with coppery-red Maji Contrast and shampooed 15 times according to the same procedure.

Example 2 Dyeing with Coppery-Red Maji Contrast

The following composition was prepared:

Olive oil 90 g Methylheptyl cyanoacrylate from Chemence 10 g

0.25 g of this composition was applied by brush to a lock of 1 g of grey hair dyed beforehand with coppery-red Maji Contrast. The lock was dried under a hood for 30 minutes and then combed. At this stage, the lock may be subjected to a final shampooing. The hair felt soft and tangle-free.

After shampooing 15 times, the color of the lock dyed and then treated according to the present disclosure was markedly more vivid than that of the lock dyed identically with coppery-red Maji Contrast and shampooed 15 times according to the same procedure.

Example 3 Dyeing with Coppery-Red Maji Contrast

Lotion A containing 0.6% of monoethanolamine in water was prepared.

Composition B below was prepared:

α,ω-Dihydroxylated polydimethylsiloxane/cyclo- 45 g pentadimethylsiloxane (14.7/85.3) sold by Dow Corning under the name DC 1501 Fluid Cyclopentadimethylsiloxane sold by Dow Corning under the 45 g name DC245 Fluid Methylheptyl cyanoacrylate from Chemence 10 g

Three locks of 1 g of grey hair, M1, M2, and M3, were dyed with a Maji Contrast coppery-red dye.

0.25 g of lotion A was applied to lock M1. 0.25 g of composition B was then applied by brush. The lock was dried under a hood for 30 minutes and then combed. At this stage, the lock may be subjected to a final shampooing.

In parallel, 0.25 g of composition B was applied by brush to lock M2. The lock was dried under a hood for 30 minutes and then combed. At this stage, the lock may be subjected to a final shampooing.

Lock M1 was shinier than lock M2.

After shampooing 15 times, the color of the two locks dyed and then treated according to the invention, M1 and M2, was markedly more vivid than that of lock M3 dyed identically with coppery-red Maji Contrast and shampooed 15 times according to the same procedure.

The combination of lotion A and of composition B made it possible to improve the appearance of the locks while at the same time maintaining a color-protecting effect of the same level as that obtained with composition B alone.

Example 4 Dyeing with Coppery-Red Maji Contrast

Composition C below was prepared:

α,ω-Dihydroxylated polydimethylsiloxane/cyclo- 45 g pentadimethylsiloxane (14.7/85.3) sold by Dow Corning under the name DC 1501 Fluid Cyclopentadimethylsiloxane sold by Dow Corning under the 41 g name DC245 Fluid Boron nitride powder CC6004 from Advanced Ceramics  4 g Methylheptyl cyanoacrylate from Chemence 10 g

Depending on the case, acetic acid may be added in an amount of 0.25% by weight relative to the total weight of the composition.

Composition D below was prepared:

α,ω-Dihydroxylated polydimethylsiloxane/cyclo- 45 g pentadimethylsiloxane (14.7/85.3) sold by Dow Corning under the name DC 1501 Fluid Cyclopentadimethylsiloxane sold by Dow Corning under the 40 g name DC245 Fluid Hydrophobic silica Aerosil R8200 from Degussa  5 g Methylheptyl cyanoacrylate from Chemence 10 g

Depending on the case, acetic acid may be added in an amount of 0.25% by weight relative to the total weight of the composition.

Composition E below was prepared:

α,ω-Dihydroxylated polydimethylsiloxane/cyclo- 34 g pentadimethylsiloxane (14.7/85.3) sold by Dow Corning under the name DC 1501 Fluid Cyclopentadimethylsiloxane sold by Dow Corning under the 51.5 g name DC245 Fluid Ethanol 4.5 g Methylheptyl cyanoacrylate from Chemence 10 g

Depending on the case, acetic acid may be added in an amount of 0.25% by weight relative to the total weight of the formula.

Five 1-g grey locks were dyed with the coppery-red Maji Contrast dye.

The locks were wrung dry, and four locks were then treated, respectively, with 0.25 g of compositions B, C, D, and E, applied by brush. The locks were dried under a hood for 30 minutes and then combed. The fifth lock was simply dried.

The five locks were shampooed 15 times.

The color of the locks treated with composition B, C, D, and E was markedly more vivid than that of the lock simply dyed and shampooed.

B. Tests to Compare the Unison of a Dyed Lock

The following composition was prepared:

α,ω-Dihydroxylated polydimethylsiloxane/cyclo- 45 g pentadimethylsiloxane (14.7/85.3) sold by Dow Corning under the name DC 1501 Fluid Cyclopentadimethylsiloxane sold by Dow Corning under the 44.75 g name DC245 Fluid Acetic acid 0.25 g Methylheptyl cyanoacrylate from Chemence 10 g

0.25 g of this composition was applied by brush to a lock M of 1 g of permanent-waved grey hair.

The lock M was dried under a hood for 30 minutes and then combed. At this stage, the lock may be subjected to a final shampooing. The hair felt soft and tangle-free.

The coppery-red Maji Contrast dye was applied to this lock M.

The dye was also applied to a control permanent-waved grey lock, noted as T.

It was observed that the lock M that received the composition comprising the cyanoacrylate had a more uniform color along its length than the simply dyed control lock T. The lock M had better unison than the control lock T.

Claims

1. A process for improving the color of artificially dyed keratin fibers comprising applying to the fibers at least one cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral or organic bases, and C1-C8 lower alcohols.

2. A process for protecting the color of keratin fibers and their cosmetic properties after washing comprising applying to the fibers at least one cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral or organic bases, and C1-C8 lower alcohols.

3. A process for improving the unison of the color of artificially dyed keratin fibers comprising applying to the fibers at least one cosmetic composition comprising at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral or organic bases, and C1-C8 lower alcohols.

4. The process of claim 1, wherein the at least one cyanoacrylate monomer is chosen from those of formula (I):

wherein: X is chosen from NH, S, and O, R1 and R2, which may be identical or different, are chosen from sparingly electron-withdrawing groups and non-electron-withdrawing groups, R is chosen from saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups; R′3 is chosen from hydrogen and saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups.

5. The process of claim 4, wherein R1 and R2, which may be identical or different, are chosen from:

hydrogen,
saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR, —COOR, —COR, —SH, —SR, —OH, and halogens,
modified and unmodified polyorganosiloxane residues, and
polyoxyalkylene groups.

6. The process of claim 4, wherein the at least one cyanoacrylate monomer of formula (I) is chosen from the alkyl and alkoxyalkyl 2-cyanoacrylates of formula (IV):

wherein:
R1 and R2 have the same meaning as for formula (I), and
R′3 is chosen from C1-C10 alkyl radicals and (C1-C4)alkoxy(C1-C10)alkyl radicals.

7. The process of claim 6, wherein the at least one cyanoacrylate monomer is chosen from ethyl 2-cyanoacrylate, methyl 2-cyanoacrylate, n-propyl 2-cyanoacrylate, isopropyl 2-cyanoacrylate, tert-butyl 2-cyanoacrylate, n-butyl 2-cyanoacrylate, isobutyl 2-cyanoacrylate, 3-methoxybutyl cyanoacrylate, 2-methoxypropyl 2-cyanoacrylate, allyl 2-cyanoacrylate, n-decyl cyanoacrylate, hexyl 2-cyanoacrylate, 2-ethoxyethyl 2-cyanoacrylate, 2-methoxyethyl 2-cyanoacrylate, 2-octyl 2-cyanoacrylate, 2-propoxyethyl 2-cyanoacrylate, n-octyl 2-cyanoacrylate, and isoamyl cyanoacrylate.

8. The process of claim 7, wherein the at least one cyanoacrylate monomer is chosen from C6-C10 alkyl 2-cyanoacrylates.

9. The process of claim 8, wherein the at least one cyanoacrylate monomer is chosen from the octyl 2-cyanoacrylates of formula (V):

wherein:
R1 and R2 have the same meaning as for formula (I), and
R′3 is chosen from: —(CH2)7—CH3; —CH(CH3)—(CH2)5—CH3; —CH2—CH(C2H5)—(CH2)3—CH3; —(CH2)5—CH(CH3)—CH3; and —(CH2)4—CH(C2H5)—CH3.

10. The process of claim 9, wherein the 2-cyanoacrylate monomer is methylheptyl cyanoacrylate.

11. The process of claim 1, wherein the at least one cyanoacrylate monomer of formula (I) is covalently bonded to at least one support chosen from polymers, oligomers, and dendrimers.

12. The process of claim 1, wherein the at least one cyanoacrylate monomer of formula (I) is present in the cosmetic composition in an amount ranging from 0.1% to 50% by weight relative to the total weight of the cosmetic composition.

13. The process of claim 12, wherein the at least one cyanoacrylate monomer of formula (I) is present in the cosmetic composition in an amount ranging from 1% to 30% by weight relative to the total weight of the cosmetic composition.

14. The process of claim 1, wherein the at least one conditioning agent is chosen from organic acids and oils.

15. The process of claim 14, wherein the at least one conditioning agent is a C1-C12 organic acid bearing at least one group chosen from carboxylic groups and sulfonic groups.

16. The process of claim 15, wherein the at least one organic acid is chosen from benzenesulfonic acid, toluenesulfonic acid, acetic acid, formic acid, propionic acid, benzoic acid, mono-, di-, or trichloroacetic acid, salicylic acid, trifluoroacetic acid, citric acid, octanoic acid, heptanoic acid, and hexanoic acid.

17. The process of claim 16, wherein the at least one organic acid is chosen from acetic acid, citric acid, and octanoic acid.

18. The process of claim 15, wherein the at least one organic acid is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

19. The process of claim 18, wherein the at least one organic acid is present in the cosmetic composition in an amount ranging from 0.1% to 15% by weight relative to the total weight of the cosmetic composition.

20. The process of claim 14, wherein the at least one conditioning agent is chosen from mineral oils, organic oils, and plant oils.

21. The process of claim 20, wherein the at least one conditioning agent is a plant oil chosen from olive oil, castor oil, rapeseed oil, coconut oil, wheatgerm oil, sweet almond oil, avocado oil, polybutene oil, macadamia oil, apricot kernel oil, isononyl isononanoate, safflower oil, candlenut oil, isostearyl malate, jojoba oil, sunflower oil, sesame seed oil, groundnut oil, grapeseed oil, soybean oil, corn oil, hazelnut oil, shea butter, palm oil, beauty-leaf oil, camelina oil, tamanu kernel oil, pentaerythrityl tetraisostearate, tridecyl trimellitate, and lemon oil.

22. The process of claim 21, wherein the plant oil is olive oil.

23. The process of claim 20, wherein the at least one conditioning agent is an oil chosen from volatile silicone oils.

24. The process of claim 23, wherein the at least one volatile silicone oil is chosen from octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, and mixtures of cyclic silicones with organosilicon compounds.

25. The process of claim 24, wherein the at least one volatile silicone oil is chosen from mixtures of octamethylcyclotetrasiloxane and of tetrakis(trimethylsilyl)pentaerythritol (50/50) and mixtures of octamethylcyclotetrasiloxane and of oxy-1,1′-bis[2,2,2′,2′,3,3′-hexakis(trimethylsilyloxy)]neopentane.

26. The process of claim 24, wherein the at least one volatile silicone oil is decamethylcyclopentasiloxane.

27. The process of claim 20, wherein the at least one conditioning agent is a fluid silicone chosen from:

decamethylcyclopentasiloxane and dimethiconol mixtures,
decamethylcyclopentasiloxane and dimethicone mixtures, and
fluid PDMS and dimethiconol mixtures.

28. The process of claim 20, wherein the at least one conditioning agent is present in the cosmetic composition in an amount ranging from 1% to 99.9% by weight relative to the total weight of the cosmetic composition.

29. The process of claim 28, wherein the at least one conditioning agent is present in the cosmetic composition in an amount ranging from 20% to 85% by weight relative to the total weight of the cosmetic composition.

30. The process of claim 1, wherein the at least one additional compound is a filler chosen from mineral and organic fillers.

31. The process of claim 30, wherein the at least one filler is chosen from talc, mica, silica, fumed silica optionally surface-treated with a hydrophobic agent, kaolin, bentone, polyamide powder, poly-β-alanine powder and polyethylene powder, tetrafluoroethylene polymer powders, lauroyllysine, starch, boron nitride, hollow polymer microspheres, elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, hydroxyapatite, hollow silica microspheres, glass and ceramic microcapsules, and metal soaps derived from organic carboxylic acids comprising from 8 to 22 carbon atoms.

32. The process of claim 1, wherein the hollow polymer microspheres are chosen from polyvinylidene chloride/acrylonitrile copolymer microspheres, acrylic acid copolymer microspheres, and silicone resin microbeads.

33. The process of claim 31, wherein the at least one metal soap is chosen from zinc stearate, magnesium stearate, lithium stearate, zinc laurate, and magnesium myristate.

34. The process of claim 31, wherein the at least one filler is chosen from fumed silicas optionally surface-treated with a hydrophobic agent and boron nitride.

35. The process of claim 30, wherein the at least one filler is present in the cosmetic composition in an amount ranging from 0.01% to 50% by weight relative to the total weight of the composition.

36. The process of claim 35, wherein the at least one filler is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

37. The process of claim 1, wherein the at least one additional compound is a mineral or organic base chosen from aqueous ammonia, monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine, alkali metal carbonates and bicarbonates, ammonium carbonates and bicarbonates, organic carbonates, and alkali metal hydroxides.

38. The process of claim 37, wherein the at least one mineral or organic base is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

39. The process of claim 38, wherein the at least one mineral or organic base is present in the cosmetic composition in an amount ranging from 0.01% to 5% by weight relative to the total weight of the cosmetic composition.

40. The process of claim 1, wherein the at least one additional compound is a C1-C8 lower alcohol chosen from lower monoalcohols comprising from 1 to 5 carbon atoms and glycols comprising from 2 to 8 carbon atoms.

41. The process of claim 40, wherein the at least one C1-C8 lower alcohol is ethanol.

42. The process of claim 40, wherein the at least one C1-C8 lower alcohol is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

43. The process of claim 42, wherein the at least one C1-C8 lower alcohol is present in the cosmetic composition in an amount ranging from 0.01% to 5% by weight relative to the total weight of the cosmetic composition.

44. The process of claim 1, wherein the at least one cosmetic composition further comprises at least one polymerization inhibitor.

45. The process of claim 44, wherein the at least one polymerization inhibitor is present in the cosmetic composition in an amount ranging from 10 ppm to 5% by weight relative to the total weight of the composition.

46. The process of claim 1, wherein the at least one cosmetic composition further comprises at least one organic UV-screening agent.

47. The process of claim 1, wherein the at least one cosmetic composition further comprises at least one polymer.

48. The process of claim 1, wherein the at least one cosmetic composition is in an anhydrous support.

49. The process of claim 1, wherein the at least one cosmetic composition comprises a support comprising at least one ingredient chosen from aromatic alcohols, liquid fatty alcohols comprising at least 12 carbon atoms, oxyethylenated and/or non-oxyethylenated waxes, paraffins, alkanes, fatty acids comprising at least 12 carbon atoms, fatty amides, and fatty esters.

50. The process of claim 1, wherein the at least one cosmetic composition comprises at least one common cosmetic additive chosen from reducing agents, oxidizing agents, sequestrants, polymeric and non-polymeric thickeners, moisturizers, emollients, plasticizers, optical brighteners, clays, colloidal minerals, colloidal metals, semi-conductive particles of “quantum well” type based on metals or on silicon, photochromic and thermochromic compounds, nacreous agents, fragrances, peptizers, preserving agents, proteins, vitamins, anti-dandruff agents, oxyethylenated and non-oxyethylenated waxes, anionic, cationic, and amphoteric fixing and non-fixing polymers, and anionic, cationic, amphoteric, and nonionic surfactants.

51. The process of claim 1, wherein the at least one cosmetic composition on the keratin fibers further comprises at least one nucleophilic agent; said nucleophilic agent being either in a mixture in the cosmetic composition according to claim 1, or contained separately prior to application.

52. The process of claim 51, wherein the at least one nucleophilic agent is water.

53. A dyeing process comprising applying a dye composition (A) to keratin fibers, for a time that is sufficient to develop the color, and applying, in the presence of at least one nucleophilic agent, a composition (B) comprising a cosmetic composition, following or preceding the application of the dye composition (A);

wherein the at least one nucleophilic agent is mixed at the time of use into the cosmetic composition (B) or applied separately;
wherein the dye composition (A) is chosen from: dye compositions containing at least one direct dye (A1), lightening direct dye compositions containing at least one direct dye and at least one oxidizing agent (A2), dye compositions comprising at least one oxidation dyeing base and optionally at least one coupler (A3), and dye compositions comprising at least one oxidation dyeing base, optionally at least one coupler, and at least one direct dye (A4); and
wherein the cosmetic composition comprises at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral and organic bases, and C1-C8 lower alcohols.

54. A multi-component coloring kit comprising

at least one first component comprising a dye composition (A),
at least one second component comprising a composition (B) containing a cosmetic composition, optionally at least one third component comprising a composition (C) comprising at least one oxidizing agent, and optionally at least one fourth component comprising a composition (D) containing at least one nucleophilic agent; wherein the dye composition (A) is chosen from: dye compositions containing at least one direct dye (A1), lightening direct dye compositions containing at least one direct dye and at least one oxidizing agent (A2), dye compositions comprising at least one oxidation dyeing base and optionally at least one coupler (A3), and dye compositions comprising at least one oxidation dyeing base, optionally at least one coupler, and at least one direct dye (A4); and wherein the cosmetic composition (B) comprises at least one polymerizable cyanoacrylate monomer and at least one conditioning agent and/or at least one additional compound chosen from fillers, mineral and organic bases, and C1-C8 lower alcohols.

55. The process of claim 2, wherein the at least one cyanoacrylate monomer is chosen from those of formula (I):

wherein:
X is chosen from NH, S, and O,
R1 and R2, which may be identical or different, are chosen from sparingly electron-withdrawing groups and non-electron-withdrawing groups,
R is chosen from saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups;
R′3 is chosen from hydrogen and saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups.

56. The process of claim 55, wherein R1 and R2, which may be identical or different, are chosen from:

hydrogen,
saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR, —COOR, —COR, —SH, —SR, —OH, and halogens,
modified and unmodified polyorganosiloxane residues, and
polyoxyalkylene groups.

57. The process of claim 55, wherein the at least one cyanoacrylate monomer of formula (I) is chosen from the alkyl and alkoxyalkyl 2-cyanoacrylates of formula (IV):

wherein:
R1 and R2 have the same meaning as for formula (I), and
R′3 is chosen from C1-C10 alkyl radicals and (C1-C4)alkoxy(C1-C10)alkyl radicals.

58. The process of claim 57, wherein the at least one cyanoacrylate monomer is chosen from ethyl 2-cyanoacrylate, methyl 2-cyanoacrylate, n-propyl 2-cyanoacrylate, isopropyl 2-cyanoacrylate, tert-butyl 2-cyanoacrylate, n-butyl 2-cyanoacrylate, isobutyl 2-cyanoacrylate, 3-methoxybutyl cyanoacrylate, 2-methoxypropyl 2-cyanoacrylate, allyl 2-cyanoacrylate, n-decyl cyanoacrylate, hexyl 2-cyanoacrylate, 2-ethoxyethyl 2-cyanoacrylate, 2-methoxyethyl 2-cyanoacrylate, 2-octyl 2-cyanoacrylate, 2-propoxyethyl 2-cyanoacrylate, n-octyl 2-cyanoacrylate, and isoamyl cyanoacrylate.

59. The process of claim 58, wherein the at least one cyanoacrylate monomer is chosen from C6-C10 alkyl 2-cyanoacrylates.

60. The process of claim 59, wherein the at least one cyanoacrylate monomer is chosen from the octyl 2-cyanoacrylates of formula (V):

wherein: R1 and R2 have the same meaning as for formula (I), and R′3 is chosen from: —(CH2)7—CH3; —CH(CH3)—(CH2)5—CH3; —CH2—CH(C2H5)—(CH2)3—CH3; —(CH2)5—CH(CH3)—CH3; and —(CH2)4—CH(C2H5)—CH3.

61. The process of claim 60, wherein the 2-cyanoacrylate monomer is methylheptyl cyanoacrylate.

62. The process of claim 2, wherein the at least one cyanoacrylate monomer of formula (I) is covalently bonded to at least one support chosen from polymers, oligomers, and dendrimers.

63. The process of claim 2, wherein the at least one cyanoacrylate monomer of formula (I) is present in the cosmetic composition in an amount ranging from 0.1% to 50% by weight relative to the total weight of the cosmetic composition.

64. The process of claim 63, wherein the at least one cyanoacrylate monomer of formula (I) is present in the cosmetic composition in an amount ranging from 1% to 30% by weight relative to the total weight of the cosmetic composition.

65. The process of claim 2, wherein the at least one conditioning agent is chosen from organic acids and oils.

66. The process of claim 65, wherein the at least one conditioning agent is a C1-C12 organic acid bearing at least one group chosen from carboxylic groups and sulfonic groups.

67. The process of claim 66, wherein the at least one organic acid is chosen from benzenesulfonic acid, toluenesulfonic acid, acetic acid, formic acid, propionic acid, benzoic acid, mono-, di-, or trichloroacetic acid, salicylic acid, trifluoroacetic acid, citric acid, octanoic acid, heptanoic acid, and hexanoic acid.

68. The process of claim 67, wherein the at least one organic acid is chosen from acetic acid, citric acid, and octanoic acid.

69. The process of claim 66, wherein the at least one organic acid is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

70. The process of claim 69, wherein the at least one organic acid is present in the cosmetic composition in an amount ranging from 0.1% to 15% by weight relative to the total weight of the cosmetic composition.

71. The process of claim 65, wherein the at least one conditioning agent is chosen from mineral oils, organic oils, and plant oils.

72. The process of claim 71, wherein the at least one conditioning agent is a plant oil chosen from olive oil, castor oil, rapeseed oil, coconut oil, wheatgerm oil, sweet almond oil, avocado oil, polybutene oil, macadamia oil, apricot kernel oil, isononyl isononanoate, safflower oil, candlenut oil, isostearyl malate, jojoba oil, sunflower oil, sesame seed oil, groundnut oil, grapeseed oil, soybean oil, corn oil, hazelnut oil, shea butter, palm oil, beauty-leaf oil, camelina oil, tamanu kernel oil, pentaerythrityl tetraisostearate, tridecyl trimellitate, and lemon oil.

73. The process of claim 72, wherein the plant oil is olive oil.

74. The process of claim 71, wherein the at least one conditioning agent is an oil chosen from volatile silicone oils.

75. The process of claim 74, wherein the at least one volatile silicone oil is chosen from octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, and mixtures of cyclic silicones with organosilicon compounds.

76. The process of claim 75, wherein the at least one volatile silicone oil is chosen from mixtures of octamethylcyclotetrasiloxane and of tetrakis(trimethylsilyl)pentaerythritol (50/50) and mixtures of octamethylcyclotetrasiloxane and of oxy-111′-bis[2,2,2′,2′,3,3′-hexakis(trimethylsilyloxy)]neopentane.

77. The process of claim 75, wherein the at least one volatile silicone oil is decamethylcyclopentasi loxane.

78. The process of claim 71, wherein the at least one conditioning agent is a fluid silicone chosen from:

decamethylcyclopentasiloxane and dimethiconol mixtures,
decamethylcyclopentasiloxane and dimethicone mixtures, and
fluid PDMS and dimethiconol mixtures.

79. The process of claim 71, wherein the at least one conditioning agent is present in the cosmetic composition in an amount ranging from 1% to 99.9% by weight relative to the total weight of the cosmetic composition.

80. The process of claim 79, wherein the at least one conditioning agent is present in the cosmetic composition in an amount ranging from 20% to 85% by weight relative to the total weight of the cosmetic composition.

81. The process of claim 2, wherein the at least one additional compound is a filler chosen from mineral and organic fillers.

82. The process of claim 81, wherein the at least one filler is chosen from talc, mica, silica, fumed silica optionally surface-treated with a hydrophobic agent, kaolin, bentone, polyamide powder, poly-β-alanine powder and polyethylene powder, tetrafluoroethylene polymer powders, lauroyllysine, starch, boron nitride, hollow polymer microspheres, elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, hydroxyapatite, hollow silica microspheres, glass and ceramic microcapsules, and metal soaps derived from organic carboxylic acids comprising from 8 to 22 carbon atoms.

83. The process of claim 2, wherein the hollow polymer microspheres are chosen from polyvinylidene chloride/acrylonitrile copolymer microspheres, acrylic acid copolymer microspheres, and silicone resin microbeads.

84. The process of claim 82, wherein the at least one metal soap is chosen from zinc stearate, magnesium stearate, lithium stearate, zinc laurate, and magnesium myristate.

85. The process of claim 82, wherein the at least one filler is chosen from fumed silicas optionally surface-treated with a hydrophobic agent and boron nitride.

86. The process of claim 81, wherein the at least one filler is present in the cosmetic composition in an amount ranging from 0.01% to 50% by weight relative to the total weight of the composition.

87. The process of claim 86, wherein the at least one filler is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

88. The process of claim 2, wherein the at least one additional compound is a mineral or organic base chosen from aqueous ammonia, monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine, alkali metal carbonates and bicarbonates, ammonium carbonates and bicarbonates, organic carbonates, and alkali metal hydroxides.

89. The process of claim 88, wherein the at least one mineral or organic base is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

90. The process of claim 89, wherein the at least one mineral or organic base is present in the cosmetic composition in an amount ranging from 0.01% to 5% by weight relative to the total weight of the cosmetic composition.

91. The process of claim 2, wherein the at least one additional compound is a C1-C8 lower alcohol chosen from lower monoalcohols comprising from 1 to 5 carbon atoms and glycols comprising from 2 to 8 carbon atoms.

92. The process of claim 91, wherein the at least one C1-C8 lower alcohol is ethanol.

93. The process of claim 91, wherein the at least one C1-C8 lower alcohol is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

94. The process of claim 93, wherein the at least one C1-C8 lower alcohol is present in the cosmetic composition in an amount ranging from 0.01% to 5% by weight relative to the total weight of the cosmetic composition.

95. The process of claim 2, wherein the at least one cosmetic composition further comprises at least one polymerization inhibitor.

96. The process of claim 95, wherein the at least one polymerization inhibitor is present in the cosmetic composition in an amount ranging from 10 ppm to 5% by weight relative to the total weight of the composition.

97. The process of claim 2, wherein the at least one cosmetic composition further comprises at least one organic UV-screening agent.

98. The process of claim 2, wherein the at least one cosmetic composition further comprises at least one polymer.

99. The process of claim 2, wherein the at least one cosmetic composition is in an anhydrous support.

100. The process of claim 2, wherein the at least one cosmetic composition comprises a support comprising at least one ingredient chosen from aromatic alcohols, liquid fatty alcohols comprising at least 12 carbon atoms, oxyethylenated and/or non-oxyethylenated waxes, paraffins, alkanes, fatty acids comprising at least 12 carbon atoms, fatty amides, and fatty esters.

101. The process of claim 2, wherein the at least one cosmetic composition comprises at least one common cosmetic additive chosen from reducing agents, oxidizing agents, sequestrants, polymeric and non-polymeric thickeners, moisturizers, emollients, plasticizers, optical brighteners, clays, colloidal minerals, colloidal metals, semi-conductive particles of “quantum well” type based on metals or on silicon, photochromic and thermochromic compounds, nacreous agents, fragrances, peptizers, preserving agents, proteins, vitamins, anti-dandruff agents, oxyethylenated and non-oxyethylenated waxes, anionic, cationic, and amphoteric fixing and non-fixing polymers, and anionic, cationic, amphoteric, and nonionic surfactants.

102. The process of claim 2, wherein the at least one cosmetic composition on the keratin fibers further comprises at least one nucleophilic agent; said nucleophilic agent being either in a mixture in the cosmetic composition according to claim 1, or contained separately prior to application.

103. The process of claim 102, wherein the at least one nucleophilic agent is water.

104. The process of claim 3, wherein the at least one cyanoacrylate monomer is chosen from those of formula (I):

wherein:
X is chosen from NH, S, and O,
R1 and R2, which may be identical or different, are chosen from sparingly electron-withdrawing groups and non-electron-withdrawing groups,
R is chosen from saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups;
R′3 is chosen from hydrogen and saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR′, —COOR′, —COR′, —SH, —SR′, —OH, and halogens, and polymer residues obtained by a process chosen from free-radical polymerization, polycondensation, and ring opening, wherein R′ is chosen from C1-C10 alkyl groups.

105. The process of claim 104, wherein R1 and R2, which may be identical or different, are chosen from:

hydrogen,
saturated and unsaturated, linear, branched and cyclic hydrocarbon-based groups comprising from 1 to 20 carbon atoms, and optionally comprising at least one atom chosen from nitrogen, oxygen, and sulfur, and optionally substituted with at least one entity chosen from —OR, —COOR, —COR, —SH, —SR, —OH, and halogens,
modified and unmodified polyorganosiloxane residues, and
polyoxyalkylene groups.

106. The process of claim 104, wherein the at least one cyanoacrylate monomer of formula (I) is chosen from the alkyl and alkoxyalkyl 2-cyanoacrylates of formula (IV):

wherein:
R1 and R2 have the same meaning as for formula (I), and
R′3 is chosen from C1-C10 alkyl radicals and (C1-C4)alkoxy(C1-C10)alkyl radicals.

107. The process of claim 106, wherein the at least one cyanoacrylate monomer is chosen from ethyl 2-cyanoacrylate, methyl 2-cyanoacrylate, n-propyl 2-cyanoacrylate, isopropyl 2-cyanoacrylate, tert-butyl 2-cyanoacrylate, n-butyl 2-cyanoacrylate, isobutyl 2-cyanoacrylate, 3-methoxybutyl cyanoacrylate, 2-methoxypropyl 2-cyanoacrylate, allyl 2-cyanoacrylate, n-decyl cyanoacrylate, hexyl 2-cyanoacrylate, 2-ethoxyethyl 2-cyanoacrylate, 2-methoxyethyl 2-cyanoacrylate, 2-octyl 2-cyanoacrylate, 2-propoxyethyl 2-cyanoacrylate, n-octyl 2-cyanoacrylate, and isoamyl cyanoacrylate.

108. The process of claim 107, wherein the at least one cyanoacrylate monomer is chosen from C6-C10 alkyl 2-cyanoacrylates.

109. The process of claim 108, wherein the at least one cyanoacrylate monomer is chosen from the octyl 2-cyanoacrylates of formula (V):

wherein: R1 and R2 have the same meaning as for formula (I), and R′3 is chosen from: —(CH2)7—CH3; —CH(CH3)—(CH2)5—CH3; —CH2—CH(C2H5)—(CH2)3—CH3; —(CH2)5—CH(CH3)—CH3; and (CH2)4—CH(C2H5)—CH3.

110. The process of claim 109, wherein the 2-cyanoacrylate monomer is methylheptyl cyanoacrylate.

111. The process of claim 3, wherein the at least one cyanoacrylate monomer of formula (I) is covalently bonded to at least one support chosen from polymers, oligomers, and dendrimers.

112. The process of claim 3, wherein the at least one cyanoacrylate monomer of formula (I) is present in the cosmetic composition in an amount ranging from 0.1% to 50% by weight relative to the total weight of the cosmetic composition.

113. The process of claim 112, wherein the at least one cyanoacrylate monomer of formula (I) is present in the cosmetic composition in an amount ranging from 1% to 30% by weight relative to the total weight of the cosmetic composition.

114. The process of claim 3, wherein the at least one conditioning agent is chosen from organic acids and oils.

115. The process of claim 114, wherein the at least one conditioning agent is a C1-C12 organic acid bearing at least one group chosen from carboxylic groups and sulfonic groups.

116. The process of claim 115, wherein the at least one organic acid is chosen from benzenesulfonic acid, toluenesulfonic acid, acetic acid, formic acid, propionic acid, benzoic acid, mono-, di-, or trichloroacetic acid, salicylic acid, trifluoroacetic acid, citric acid, octanoic acid, heptanoic acid, and hexanoic acid.

117. The process of claim 116, wherein the at least one organic acid is chosen from acetic acid, citric acid, and octanoic acid.

118. The process of claim 115, wherein the at least one organic acid is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

119. The process of claim 118, wherein the at least one organic acid is present in the cosmetic composition in an amount ranging from 0.1% to 15% by weight relative to the total weight of the cosmetic composition.

120. The process of claim 114, wherein the at least one conditioning agent is chosen from mineral oils, organic oils, and plant oils.

121. The process of claim 120, wherein the at least one conditioning agent is a plant oil chosen from olive oil, castor oil, rapeseed oil, coconut oil, wheatgerm oil, sweet almond oil, avocado oil, polybutene oil, macadamia oil, apricot kernel oil, isononyl isononanoate, safflower oil, candlenut oil, isostearyl malate, jojoba oil, sunflower oil, sesame seed oil, groundnut oil, grapeseed oil, soybean oil, corn oil, hazelnut oil, shea butter, palm oil, beauty-leaf oil, camelina oil, tamanu kernel oil, pentaerythrityl tetraisostearate, tridecyl trimellitate, and lemon oil.

122. The process of claim 121, wherein the plant oil is olive oil.

123. The process of claim 120, wherein the at least one conditioning agent is an oil chosen from volatile silicone oils.

124. The process of claim 123, wherein the at least one volatile silicone oil is chosen from octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, and mixtures of cyclic silicones with organosilicon compounds.

125. The process of claim 124, wherein the at least one volatile silicone oil is chosen from mixtures of octamethylcyclotetrasiloxane and of tetrakis(trimethylsilyl)pentaerythritol (50/50) and mixtures of octamethylcyclotetrasiloxane and of oxy-111′-bis[2,2,2′,2′,3,3′-hexakis(trimethylsilyloxy)]neopentane.

126. The process of claim 124, wherein the at least one volatile silicone oil is decamethylcyclopentasiloxane.

127. The process of claim 120, wherein the at least one conditioning agent is a fluid silicone chosen from:

decamethylcyclopentasiloxane and dimethiconol mixtures,
decamethylcyclopentasiloxane and dimethicone mixtures, and
fluid PDMS and dimethiconol mixtures.

128. The process of claim 120, wherein the at least one conditioning agent is present in the cosmetic composition in an amount ranging from 1% to 99.9% by weight relative to the total weight of the cosmetic composition.

129. The process of claim 128, wherein the at least one conditioning agent is present in the cosmetic composition in an amount ranging from 20% to 85% by weight relative to the total weight of the cosmetic composition.

130. The process of claim 3, wherein the at least one additional compound is a filler chosen from mineral and organic fillers.

131. The process of claim 130, wherein the at least one filler is chosen from talc, mica, silica, fumed silica optionally surface-treated with a hydrophobic agent, kaolin, bentone, polyamide powder, poly-β-alanine powder and polyethylene powder, tetrafluoroethylene polymer powders, lauroyllysine, starch, boron nitride, hollow polymer microspheres, elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, hydroxyapatite, hollow silica microspheres, glass and ceramic microcapsules, and metal soaps derived from organic carboxylic acids comprising from 8 to 22 carbon atoms.

132. The process of claim 3, wherein the hollow polymer microspheres are chosen from polyvinylidene chloride/acrylonitrile copolymer microspheres, acrylic acid copolymer microspheres, and silicone resin microbeads.

133. The process of claim 131, wherein the at least one metal soap is chosen from zinc stearate, magnesium stearate, lithium stearate, zinc laurate, and magnesium myristate.

134. The process of claim 131, wherein the at least one filler is chosen from fumed silicas optionally surface-treated with a hydrophobic agent and boron nitride.

135. The process of claim 130, wherein the at least one filler is present in the cosmetic composition in an amount ranging from 0.01% to 50% by weight relative to the total weight of the composition.

136. The process of claim 135, wherein the at least one filler is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

137. The process of claim 3, wherein the at least one additional compound is a mineral or organic base chosen from aqueous ammonia, monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine, alkali metal carbonates and bicarbonates, ammonium carbonates and bicarbonates, organic carbonates, and alkali metal hydroxides.

138. The process of claim 137, wherein the at least one mineral or organic base is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

139. The process of claim 138, wherein the at least one mineral or organic base is present in the cosmetic composition in an amount ranging from 0.01% to 5% by weight relative to the total weight of the cosmetic composition.

140. The process of claim 3, wherein the at least one additional compound is a C1-C8 lower alcohol chosen from lower monoalcohols comprising from 1 to 5 carbon atoms and glycols comprising from 2 to 8 carbon atoms.

141. The process of claim 140, wherein the at least one C1-C8 lower alcohol is ethanol.

142. The process of claim 140, wherein the at least one C1-C8 lower alcohol is present in the cosmetic composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the cosmetic composition.

143. The process of claim 142, wherein the at least one C1-C8 lower alcohol is present in the cosmetic composition in an amount ranging from 0.01% to 5% by weight relative to the total weight of the cosmetic composition.

144. The process of claim 3, wherein the at least one cosmetic composition further comprises at least one polymerization inhibitor.

145. The process of claim 144, wherein the at least one polymerization inhibitor is present in the cosmetic composition in an amount ranging from 10 ppm to 5% by weight relative to the total weight of the composition.

146. The process of claim 3, wherein the at least one cosmetic composition further comprises at least one organic UV-screening agent.

147. The process of claim 3, wherein the at least one cosmetic composition further comprises at least one polymer.

148. The process of claim 3, wherein the at least one cosmetic composition is in an anhydrous support.

149. The process of claim 3, wherein the at least one cosmetic composition comprises a support comprising at least one ingredient chosen from aromatic alcohols, liquid fatty alcohols comprising at least 12 carbon atoms, oxyethylenated and/or non-oxyethylenated waxes, paraffins, alkanes, fatty acids comprising at least 12 carbon atoms, fatty amides, and fatty esters.

150. The process of claim 3, wherein the at least one cosmetic composition comprises at least one common cosmetic additive chosen from reducing agents, oxidizing agents, sequestrants, polymeric and non-polymeric thickeners, moisturizers, emollients, plasticizers, optical brighteners, clays, colloidal minerals, colloidal metals, semi-conductive particles of “quantum well” type based on metals or on silicon, photochromic and thermochromic compounds, nacreous agents, fragrances, peptizers, preserving agents, proteins, vitamins, anti-dandruff agents, oxyethylenated and non-oxyethylenated waxes, anionic, cationic, and amphoteric fixing and non-fixing polymers, and anionic, cationic, amphoteric, and nonionic surfactants.

151. The process of claim 3, wherein the at least one cosmetic composition on the keratin fibers further comprises at least one nucleophilic agent; said nucleophilic agent being either in a mixture in the cosmetic composition according to claim 1, or contained separately prior to application.

152. The process of claim 151, wherein the at least one nucleophilic agent is water.

Patent History
Publication number: 20070261179
Type: Application
Filed: Apr 13, 2007
Publication Date: Nov 15, 2007
Inventors: Jocelyne Dorkel (le Plessis - Bouchard), Gabin Vic (Venette), Henri Samain (Bievres)
Application Number: 11/783,998
Classifications
Current U.S. Class: 8/441.000; 8/442.000
International Classification: D06P 5/08 (20060101);