Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/42—Amides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/42—Colour properties
  • A61K2800/43—Pigments; Dyes
  • A61K2800/432—Direct dyes
  • A61K2800/4324—Direct dyes in preparations for permanently dyeing the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

• the present invention relates to a composition for the direct dyeing of keratinous fibres, in particular human keratinous fibres, such as the hair, comprising, in a medium appropriate for dyeing, at least one cationic or anionic direct dye and at least one specific ammonium salt .
• dyeing compositions comprising direct dyes.
• These dyes can be anionic, cationic or neutral.
• the conventional dyes which are used are in particular dyes of the nitrobenzene, anthraquinone, nitropyridine, azo, cationic azo, xanthene, acridine, azine or triarylmethane type or natural dyes.
• These dyes which are coloured and colouring molecules having an affinity for the fibres, are applied to the keratinous fibres for a time necessary for the desired colouring to be obtained and then rinsed out.
• the colourings which result therefrom are particularly chromatic colourings which, however, are temporary or semipermanent as the nature of the interactions which bind direct dyes to the keratinous fibre and their desorption from the surface and/or from the core of the fibre are responsible for their weak dyeing power and for their poor resistance to washing operations or to perspiration.
• these direct dyes are generally sensitive to light due to the weak resistance of the chromophore with regard to photochemical attacks and result over time in dulling of the colour of the hair .
• the cationic direct dyes available in the field of the dyeing of keratinous fibres, in particular human keratinous fibres, are known to include dyes, generally known as Arianor dyes, comprising an exocyclic quaternary trialkylammonium group, which result in colourings exhibiting characteristics which are still inadequate .
• the colouring obtained is unsatisfactory.
• the aim of the present invention is to develop direct dyeing compositions possessing improved cosmetic properties which also make it possible to obtain powerful and chromatic shades which are luminous, with low selectivities and good persistence with regard to chemical agents, such as shampoos or perms, or natural agents, such as light, perspiration or sebum.
• a subject-matter of which is a composition for the direct dyeing of keratinous fibres, in particular human keratinous fibres, such as the hair, comprising, in a medium appropriate for dyeing: i) at least one direct dye chosen from anionic direct dyes and direct dyes possessing an endocyclic cationic charge; and ii) at least one ammonium salt of formula (I) : in which formula (I) :
• R represents a CH 3 CH 2 -CH (R 3 ) -CH 2 - (CH 2 ) m - group, with R 3 representing a saturated or unsaturated and linear or branched alkyl group and m representing an integer of between 0 and 30 inclusive;
• ⁇ Ri and R2 which are identical or different, represent a group chosen from i) alkyl; ii) alkenyl; iii) alkoxy and iv) alkenyloxy and v) aryl; it being possible for the alkyl or alkenyl group of the groups from i) to iv) to be interrupted by one or more identical or different heteroatoms chosen from oxygen, sulphur or N(Ra), with Ra representing a hydrogen atom or an alkyl group;
• ⁇ X represents the following aminoalkylene group -N (R 4 ) - (CH 2 ) p -, with R 4 representing a hydrogen atom or a linear or branched alkyl group, preferably a hydrogen atom, and p representing an integer of between 1 and 6 inclusive, preferably 3;
• ⁇ Y represents an alkyl or alkoxy group; it being possible for the alkyl group of the alkyl or alkoxy groups to be interrupted by one or more identical or different heteroatoms chosen from oxygen, sulphur or N(Ra) with Ra as defined above;
• ⁇ Q " represents the anionic counterion associated with the quaternary ammonium.
• the invention is also targeted at a method for colouring keratinous fibres and in particular human keratinous fibres, such as the hair, which consists in applying, to the fibres, the composition of the invention .
• a subject-matter of the present invention is the use, as direct dye in direct dyeing compositions for keratinous fibres, of a combination comprising i) at least one direct dye chosen from anionic direct dyes and direct dyes possessing an endocyclic cationic charge; and ii) at least one ammonium salt of formula (I) as defined above.
• composition of the present invention makes it possible to obtain a colouring of keratinous fibres of very good quality in terms of power, of homogeneity and of toughness which additionally exhibits, after colouring, a particularly pleasant feel on the fibres, in particular on the dry fibres.
• the colouring is persistent with regard in particular to shampoos.
• the disentangling of the fibres is facilitated and the particularly shiny appearance of the keratinous fibres is highly attractive.
• an "alkyl radical” is a linear or branched Ci- Ci6, preferably Ci-C ⁇ , hydrocarbon radical;
• an "alkenyl radical” is a linear or branched C 2 -
• C16 hydrocarbon radical comprising from 1 to 5 conjugated or nonconjugated ⁇ double bonds, preferably a Ci-C ⁇ hydrocarbon radical comprising 1 or 2 double bonds;
• an "alkoxy radical” is an alkyl-oxy (alkyl-O-) radical for which the alkyl radical is a radical as defined above;
• an "alkenyloxy radical” is an alkenyl-oxy radical for which the alkenyl radical is a radical as defined above;
• a "polyhaloalkyl radical” is an alkyl radical comprising from 1 to 6 identical or different halogens, such as trifluoromethyl;
• - an "aryl” radical represents a mono- or fused or nonfused polycyclic group comprising from 6 to 19 carbon atoms, at least one ring of which is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl, xylyl, anthracyl, phenanthryl, in
• the anionic direct dyes of the invention are dyes commonly referred to as "acid" direct dyes for their affinity with alkaline substances.
• the term "anionic direct dyes” is understood to mean any direct dye comprising, in its structure, at least one CO2R or SO3R substituent with R denoting a hydrogen atom or a cation originating from a metal or from an amine or an ammonium ion.
• the anionic dyes can be chosen from acid nitro direct dyes, acid azo dyes, acid azine dyes, acid triarylmethane dyes, acid indoamine dyes, acid anthra- quinone dyes, indigoids and acid natural dyes.
• R 7 , R 8 , Rg, Rio, R' 7 , R' 8, R' 9 and R'io which are identical or different, represent a hydrogen atom or a group chosen from: - alkyl; alkoxy, alkylthio; hydroxyl, mercapto; nitro, nitroso; - R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X) -X"-, with
• R° representing a hydrogen atom or an alkyl or aryl group and X, X' and X", which are identical or different, representing an oxygen or sulphur atom or NR with R representing a hydrogen atom or an alkyl group;
• W represents a sigma ⁇ bond, an oxygen or sulphur atom or a divalent radical i) -NR-, with R as defined above, or ii) methylene -C (R a ) (Rb)-, with R a and R] 3 , which are identical or different, representing a hydrogen atom or an aryl group, or then R a and R] 3 form, together with the carbon atom which carries them, a spiro cycloalkyl; preferably, W represents a sulphur atom or R a and R b together form a cyclohexy
• dyes of formula (II) of: Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3, Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2 ; and mention may be made, as example of dyes of formula (II) , of: Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid
• ⁇ Rn, Ri2 and R13 which are identical or different, represent a hydrogen or halogen atom or an alkyl or -(O) 2 S(O " ) M + group, with M + as defined above;
• ⁇ Ri 4 represents a hydrogen atom, an alkyl group or a -C(O)O " M + group, with M + as defined above;
• ⁇ Ri 5 represents a hydrogen atom
• Ri6 represents an oxo group, in which case R'i6 is absent, or then R 15 with R i6 together form a double bond;
• Ri 7 and R i8 which are identical or different, represent a hydrogen atom or a group chosen from:
• R'i6, R'i9 and R'20 which are identical or different, represent a hydrogen atom or an alkyl or hydroxyl group
• ⁇ R21 represents a hydrogen atom or an alkyl or alkoxy group
• R a and Rb which are identical or different, are as defined above; preferably, R a represents a hydrogen atom and R b represents an aryl group;
• ⁇ Y represents either a hydroxyl group or an oxo group
• ⁇ represents a single bond when Y is an oxo group; and represents a double bond when Y represents a hydroxyl group;
• formulae (III) and (III 1 ) comprise at least one sulphonate radical (O) 2 S(O " )- M + or one carboxylate radical -C(O)O " M + on either of the D or E rings; preferably sodium sulphonate.
• dyes of formula (III) of: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and mention may be made, as example of dyes of formula (III 1 ), of: Acid Yellow 17.
• R 22 , R23, R24, R25, R26 and R 27 which are identical or different, represent a hydrogen or halogen atom or a group chosen from: - alkyl; hydroxyl, mercapto; alkoxy, alkylthio; optionally substituted aryloxy or arylthio, preferably substituted by one or more groups chosen from alkyl and (O) 2 S(O " )- M + , with M + as defined above; aryl (alkyl) amino optionally substituted by one or more groups chosen from alkyl and (O) 2 S(O " )- M + , with M + as defined above; - (di) (alkyl) amino;
• ⁇ Z' represents a hydrogen atom or an NR 28 R 29 group with R 28 and R 29 , which are identical or different, representing a hydrogen atom or a group chosen from: alkyl; polyhydroxyalkyl, such as hydroxyethyl; aryl optionally substituted by one or more groups, particularly i) alkyl, such as methyl, n-dodecyl or n-butyl; ii) (O) 2 S(O " )- M + , with M + as defined above; iii) R°-C(X)-X'-, R°-X'-C(X)- or R°-X'-C (X) -X"-, with R°, X, X' and X" as defined above; preferably, R° represents an alkyl group; cycloalkyl; in particular cyclohexyl;
• ⁇ Z represents a group chosen from hydroxyl and NR' 28 R' 29 with R' 28 and R' 29 , which are identical or different, representing the same atoms or groups as R 28 and R 29 as defined above;
• formulae (IV) and (IV) comprise at least one sulphonate radical (O) 2 S(O " )- M + or one carboxylate radical -C(O)O " M + ; preferably sodium sulphonate
• dyes of formula (IV) of: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; and mention may be made, as example of dyes of formula (IV), of: Acid Black 48.
• R 30 , R31 and R32 which are identical or different, represent a hydrogen or halogen atom or a group chosen from: alkyl; - alkoxy optionally substituted by one or more hydroxyl groups, alkylthio optionally substituted by one or more hydroxyl groups; hydroxyl, mercapto; nitro, nitroso; - polyhaloalkyl;
• R c and Rd which are identical or different, represent a hydrogen atom or an alkyl group
• ⁇ W is as defined above; W particularly represents an -NH- group;
• ALK represents a divalent, linear or branched, Ci-C ⁇ alkylene group; particularly, ALK represents a -CH2-CH2- group;
• ⁇ n has the value 1 or 2; ⁇ P represents an integer of between 1 and 5 inclusive;
• ⁇ q represents an integer of between 1 and 4 inclusive
• ⁇ u has the value 0 or 1; ⁇ when n has a value 1, J represents a nitro or nitroso group, particularly a nitro group;
• J represents an oxygen or sulphur atom or a divalent radical -S(O) m - with m representing an integer 1 or 2; preferably, J represents an -SO2- radical;
• ⁇ M' represents a hydrogen atom or a cationic counterion
• YN which is present or absent, represents a benzo group optionally substituted by one or more R30 groups as defined above;
• formulae (V) and (V) comprise at least one sulphonate radical (O) 2 S(O " )- M + or one carboxylate radical -C(O)O " M + ; preferably sodium sulphonate .
• dyes of formula (V) of: Acid Brown 13; Acid Orange 3; mention may be made, as example of dyes of formula (V), of: Acid Yellow 1, sodium salt of 2, 4-dinitro-l-naphthol-7-sulphonic acid, 2-piperidino-5-nitrobenzenesulphonic acid, 2- (4' -N, N- (2 "-hydroxyethyl) amino-2 ' -nitro) anilineethanesulphonic acid or 4- ( ⁇ -hydroxyethylamino) -3-nitrobenzenesulphonic acid.
• R 33 , R 34 , R 35 and R 36 which are identical or different, represent a hydrogen atom or a group chosen from alkyl, optionally substituted aryl and optionally substituted arylalkyl; particularly an alkyl group and benzyl group optionally substituted by an (O) m S (CT)- M + group, with M + and m as defined above;
• R3 7 , R38 r R39/ R40/ R41/ R-42/ R43 and R44 which are identical or different, represent a hydrogen atom or a group chosen from: alkyl; alkoxy, alkylthio; (di) (alkyl) amino; hydroxyl, mercapto; - nitro, nitroso;
• R 37 to R 4 o represent a hydrogen atom and R 4 1 to R 44 , which are identical or different, represent a hydroxyl or (O) 2 S(O " )- M + " group; and, when R 43 with R 44 together form a benzo group, it is preferably substituted by a (O) 2 S (0 " ) - group;
• At least one of the G, H, I or I' rings comprises at least one sulphonate radical (O) 2 S(O " )- or one carboxylate radical -C(O)O " ; preferably sulphonate .
• dyes of formula (VI) of: Acid Blue 1, Acid Blue 3, Acid Blue 7, Acid Blue 9, Acid Violet 49, Acid Green 50.
• R49, R50, R51 and R52 which are identical or different, represent a hydrogen or halogen atom or a group chosen from: - alkyl; alkoxy, alkylthio; hydroxyl, mercapto; - nitro, nitroso;
• R 53 R 54 , R 55 and R 4 s represent a hydrogen or halogen atom
• G represents an oxygen or sulphur atom or an NR e group with R e as defined above; particularly, G represents an oxygen atom;
• ⁇ L represents an alkoxide 0 ⁇ M + ; a thioalcoholate S ⁇ M + or an NR f group, with R f representing a hydrogen atom or an alkyl group, and M + as defined above; M + is particularly sodium or potassium;
• ⁇ L' represents an oxygen or sulphur atom or an ammonium group: N + R f R g , with R f and R g , which are identical or different, representing a hydrogen atom or an optionally substituted aryl or alkyl group; L' particularly represents an oxygen atom or a phenylamino group optionally substituted by one or more alkyl or (0) m S(0 " )- M + groups, with m and M + as defined above;
• ⁇ Q and Q' which are identical or different, represent an oxygen or sulphur atom; particularly, Q and Q' represent an oxygen atom; ⁇ M + is as defined above.
• dyes of formula (VII) of: Acid Yellow 73, Acid Red 51, Acid Red 87, Acid Red 92, Acid Red 95, Acid Violet 9.
• dyes derived from indole of formula (VIII) of:
• R-53 / R-54 / R-55 / R-56 / R-57 r R-58 r R-59 and R.60 r whi ch are identical or different, represent a hydrogen atom or a group chosen from:
• R°-C(X)-X'-, R°-X'-C(X)- or R° -X ' -C (X) -X"- R° representing a hydrogen atom or an alkyl or aryl group
• X, X' and X" which are identical or different, representing an oxygen or sulphur atom or NR, with R representing a hydrogen atom or an alkyl group
• G represents an oxygen or sulphur atom or an NR e group with R e as defined above; particularly, G represents an oxygen atom;
• R 1 and Rh which are identical or different, represent a hydrogen atom or an alkyl group; it being understood that the formula (VIII) comprises at least one sulphonate radical (O) 2 S(O " )- M + or one carboxylate radical -C(O)O " M + ; preferably sodium sulphonate .
• ⁇ R.61 represents a hydrogen or halogen atom or an alkyl group
• R 6 2, R63 and R.64 which are identical or different, represent a hydrogen atom or an (O) 2 S(O " )- M + group, with M + representing a hydrogen atom or a cationic counterion;
• R 6 i with R 6 2 or R 6 i with R 64 together 0 form a benzo group optionally substituted by one or more (O) 2 S(O " )- M + groups, with M + representing a hydrogen atom or a cationic counterion; it being understood that the formula (IX) comprises at least one sulphonate radical (O) 2 S(O " )- M + , 5 preferably sodium sulphonate.
• dyes of formula (IX) of: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.
• dyes of formulae (II) to (VII) of use in the invention are chosen from:
• the anionic dyes which are more particularly preferred are the dyes denoted in the Colour Index under the code C.I. 58005 (monosodium salt of 1, 2-dihydroxy-9, 10- 0 anthraquinone-3-sulphonic acid), C.I. 60730 (monosodium salt of 2- [ (9, 10-dihydro-4-hydroxy-9, 10-dioxo-l- anthracenyl) amino] -5-methylbenzenesulphonic acid), C.I. 15510 (monosodium salt of 4- [ (2-hydroxy-l- naphthyl) azo] benzenesulphonic acid), C.I.
• the anionic direct dye or dyes particularly represent from 0.001 to 20% by weight approximately of the total weight of the composition and preferably from 0.005 to 10% by weight approximately. More particularly, the anionic dye or dyes represent from 0.01 to 5% by weight.
• cationic direct dye possessing an endocyclic cationic charge is understood to mean any direct dye comprising, in its structure, at least one quaternized nitrogen atom included in a ring.
• the term “dye with permanent cationic charge” is used, in contrast to dyes comprising functional groups with primary, secondary or tertiary amines. It being understood that the quaternized atom included in the ring cannot represent a nitroso group (NO) .
• cationic direct dye possessing an endocyclic quaternary ammonium group is understood to mean a dye capable of colouring keratinous fibres in the absence of any oxidizing agent comprising, in its structure, at least one saturated or unsaturated heterocycle comprising, in its sequence of ring members, at least one nitrogen atom carrying a positive permanent charge, the said heterocycle comprising from 4 to 8 ring members and being optionally fused with one or more other aromatic nuclei or heterocycles and optionally comprising one or more other heteroatoms chosen from nitrogen, sulphur and oxygen. Each of these rings can optionally be substituted.
• the nitrogen atom carrying a permanent positive charge is preferably substituted by an optionally substituted C1-C30 alkyl radical or by an optionally substituted phenyl radical.
• the optional substituents of the alkyl groups are preferably chosen from halogen atoms or hydroxyl, amino, mono- or di (C1-C4) alkylamino, mono- or dihydroxy (Ci-C 4 ) alkylamino, C6-C30 aryl or cyano groups.
• the optional substituents of the aryl groups are preferably chosen from halogen atoms or C1-C30 alkyl, hydroxyl, amino, mono- or di (Ci-C 4 ) alkylamino, mono- or dihydroxy (Ci-C 4 ) alkylamino, cyano, nitro or C2-C10 acyl groups.
• this substituent on the nitrogen atom carrying a permanent charge is a Ci-C 4 alkyl group.
• this substituent is a methyl group .
• Mention may more particularly be made, as azo, methine or azomethine direct dyes possessing a quaternary ammonium group included in a ring in the context of the present invention, of: i) the following direct dyes described in Patent Application EP 1 025 834: of formula (X) G-N N-J (X) in which : the symbol G represents a group chosen from the following structures Gi to G3 :
• R 24 denotes a Ci-C 4 alkyl radical or a phenyl radical which can be substituted by a Ci-C 4 alkyl radical or a halogen atom chosen from chlorine, bromine, iodine and fluorine;
• R 25 denotes a Ci-C 4 alkyl radical or a phenyl radical
• R 26 and R 27 which are identical or different, represent a Ci-C 4 alkyl radical or a phenyl radical or together form, in Gi, a benzene ring substituted by one or more Ci-C 4 alkyl, Ci-C 4 alkoxy or NO 2 radicals or together form, in G 2 , a benzene ring optionally substituted by one or more Ci-C 4 alkyl, Ci-C 4 alkoxy or NO 2 radicals;
• R 26 can additionally denote a hydrogen atom
• Z denotes an oxygen or sulphur atom or an -NR 25 group
• M represents a -CH, -CR (R denoting Ci-Cz alkyl) or -NR 28 (X " ) r group;
• > K represents a -CH, -CR (R denoting Ci-Cz alkyl) or -NR 28 (X “ ) r group;
• > P represents a -CH, -CR (R denoting Ci-C 4 alkyl) or -NR 28 (X " ) r group;
• R28 represents an 0 ⁇ atom, a Ci-C 4 alkoxy radical or a Ci-C 4 alkyl radical
• R29 and R30 which are identical or different, represent a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a Ci- C 4 alkyl radical, a Ci-C 4 alkoxy radical or an -NO2 radical;
• X ⁇ represents an anionic counterion preferably chosen from chloride, iodide, methyl sulphate, ethyl sulphate, acetate and perchlorate; he symbol J represents: a) a group of following structure Ji:
• R 31 represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a Ci-C 4 alkyl radical, a Ci-C 4 alkoxy radical or an -OH, -NO 2 , -NHR 34 , -NR 35 R 36 or -NHCO (Ci-C 4 ) alkyl radical or forms, with R 32 , a 5- or 6-membered ring comprising or not comprising one or more heteroatoms chosen from nitrogen, oxygen or sulphur;
• R 32 represents a hydrogen atom, a halogen atom chosen from chlorine, bromine, iodine and fluorine, a Ci-C 4 alkyl radical or a Ci-C 4 alkoxy radical;
• R 33 or R 34 a 5- or 6-membered ring comprising or not comprising one or more heteroatoms chosen from nitrogen, oxygen or sulphur;
• R 33 represents a hydrogen atom, an -OH radical, an -NHR 34 radical or an -NR 35 R 36 radical;
• R34 represents a hydrogen atom, a Ci-C 4 alkyl radical, a Ci-C 4 monohydroxyalkyl radical, a C2 ⁇ C 4 - polyhydroxyalkyl radical or a phenyl radical;
• ⁇ R35 and R36 which are identical or different, represent a Ci-C 4 alkyl radical, a Ci-C 4 monohydroxyalkyl radical or a C 2 ⁇ C 4 polyhydroxyalkyl radical;
• a 5- or 6-membered nitrogenous heterocyclic group capable of including other heteroatoms and/or carbonyl groups and which can be substituted by one or more Ci-C 4 alkyl, amino or phenyl radicals, and in particular a group of following structure
• R 37 and R 38 which are identical or different, represent a hydrogen atom, a Ci 3 -Ci 0 alkyl radical or a phenyl radical;
• ⁇ n represents 0 or 1 with, when n denotes 1, U denoting the -CO- radical;
• R12 represents a hydrogen atom or a Ci-C 4 alkyl radical
• Ri3 represents a hydrogen atom, an alkyl radical which can be substituted by a -CN radical or by an amino group, or a 4'- aminophenyl radical or forms, with R12, an optionally oxygen-comprising and/or nitrogen- comprising heterocycle which can be substituted by a C1-C4 alkyl radical,
• Ri 4 and Ri5 which are identical or different, represent a hydrogen atom, a halogen atom, such as bromine, chlorine, iodine or fluorine, a Ci- C 4 alkyl or Ci-C 4 alkoxy radical or a -CN radical,
• X ⁇ represents an anion preferably chosen from chloride, methyl sulphate and acetate,
• B represents a group chosen from the following structures Bi to B 6 :
• Ri 6 represents a Ci-C 4 alkyl radical
• Ri7 and R18/ which are identical or different, represent a hydrogen atom or a Ci-C 4 alkyl radical
• Rig represents a hydrogen atom, a Ci-C 4 alkoxy radical, a halogen atom, such as bromine, chlorine, iodine or fluorine, or an amino radical,
• R20 represents a hydrogen atom or a Ci-C 4 alkyl radical or forms, with a carbon atom of the benzene ring, a heterocycle which optionally comprises oxygen and/or is substituted by one or more Ci-C 4 alkyl groups,
• R21 represents a hydrogen atom or a halogen atom, such as bromine, chlorine, iodine or fluorine,
• R22 and R23 which are identical or different, represent a hydrogen atom or a Ci-C 4 alkyl radical
• ⁇ Di and D2 which are identical or different, represent a nitrogen atom or the -CH group
• X ⁇ represents an anionic counterion preferably chosen from chloride, methyl sulphate and acetate,
• E represents a group chosen from the following structures Ei to E 8 :
• i n wh i ch R ' represents a Ci-C 4 al kyl radical ;
• E when m represents 0 and when D 1 represents a nitrogen atom, then E can also denote a group of following structure E 9 :
• R' represents a Ci-C 4 alkyl radical
• ⁇ Z and D which are identical or different, represent a nitrogen atom or the -CH group
• ⁇ R 7 and Rs which are identical or different, represent a hydrogen atom
• a Ci-C 4 alkyl radical which can be substituted by a -CN, -OH or -NH 2 radical or forms, with a carbon atom of the benzene ring, an optionally oxygen-comprising or nitrogen-comprising heterocycle which can be substituted by one or more Ci-C 4 alkyl radicals
• a 4 ' -aminophenyl radical
• ⁇ Rg and R' 9 which are identical or different, represent a hydrogen or halogen atom chosen from chlorine, bromine, iodine and fluorine, a cyano radical, a Ci-C 4 alkyl radical, a Ci-C 4 alkoxy radical or an acetyloxy radical,
• X ⁇ represents an anionic counterion, preferably chosen from chloride, methyl sulphate and acetate,
• A represents a group chosen from the following structures Ai to Ai 9 :
• R 10 which are identical or different, represent a Ci-C 4 alkyl radical which can be substituted by a hydroxyl radical and Rn represents a Ci-C 4 alkoxy radical
• Ri and R2 represent, independently of one another, a hydrogen atom or a Ci-C 4 alkyl group or can form, together with two nitrogen atoms to which they are attached and with Z or Z 2 , a 5-, 6- or 7-membered ring,
• ⁇ X represents the residue of a link forming a bridge
• n an integer 2, 3 or 4,
• > KK represents a coupler compound residue
• ⁇ R3 and R 4 represent, independently of one another, a hydrogen atom or a Ci-C 4 alkyl group
• R 5 and Re represent, independently of one another, a hydrogen atom, a Ci-C 4 alkyl group or a Ci-C 4 alkoxy group, >
• An " represents an anionic counterion which is preferably colourless.
• - cationic dyes possessing xanthene rings such as Basic Red 1, Basic Red 3, Basic Red 4, Basic Violet 10 and Basic Violet 11
• - cationic dyes possessing acridine rings such as Basic Orange 15, Basic Orange 16 and Basic Orange 17;
• the azo, methine or azomethine direct dye or dyes possessing an endocyclic cationic charge according to the invention preferably represent from 0.0001 to 20% by weight approximately of the total weight of the dyeing composition and more particularly still from 0.001 to 10% by weight approximately of this weight.
• the direct dye or dyes possessing an endocyclic cationic charge represent from 0.01 to 5% by weight approximately of the total weight of the dyeing composition.
• composition of the invention also comprises at least one ammonium salt of formula (I) as defined above .
• the ammonium salt of formula (I) comprises an R group representing an alkyl group comprising between 8 and 40 carbon atoms and m is an integer of between 3 and 25 inclusive, advantageously between 10 and 20. More advantageously, the ammonium salt of formula (I) does not have an R radical resulting from anteiso-lanoleic acid.
• the ammonium salt of formula (I) particularly comprises an R 3 group which represents an alkyl group comprising less than 12 carbon atoms, particularly from 1 to 6 carbon atoms; by way of example, R 3 represents a methyl group; and Ri and R2 particularly represent an alkyl or alkoxy group comprising from 1 to 8 carbon atoms, such as ethoxy, polyethoxy, propoxy, polypropoxy or methyl.
• ammonium salt of formula (I) comprising a group Y representing an alkoxy group, such as ethoxy, polyethoxy, propoxy or polypropoxy, or an alkyl group comprising from 1 to 6 carbon atoms.
• Y represents an ethyl group.
• Q ⁇ represents the anionic counterion of the ammonium salt of formula (I) which can be chosen from halides, alkyl sulphates, such as methyl sulphate and ethyl sulphate, alkoxy sulphates, such as methoxy sulphate and ethoxy sulphate, phosphates, lactate, citrate and acetate.
• the ammonium salt of formula (I) is 18MEA in quaternized form which comprises an R group originating from 18- methyleicosanoic acid, i.e. R 3 is a methyl and m has the value 15.
• 18MEA in quaternized form implies a quaternary ammonium salt derived from methyleicosanoic fatty acid (MethylEicosanoic Acid - 18MEA) .
• Such a compound 18MEA in quaternized form is sold by Croda (Incroquat Behenyl 18MEA) . More particularly, 18MEA in quaternized form corresponds to the quaternized derivatives of methyleicosanoic acid of Cio ⁇ C40 isoalkylamidopropylethyldimonium methosulphate R- C(O)-NH-(CH 2 )S-N + (Me) 2 Et CH 3 CH 2 -OSO 3 " with R representing the following alkyl group: CH 3 CH 2 -CH (CH 3 ) -CH 2 - (CH 2 ) 15 - .
• ammonium salt of formula (I) is not derived from linolinic acid especially anteiso linolinic acid.
• ammonium salt of formula (I) above occurs in the composition of the invention in an amount of between 0.001 and 2% by weight, with respect to the total weight of the composition, particularly between 0.01 and 1%.
• the ammonium salt occurs in the composition in an amount of between 0.02 and 0.4%.
• the dyeing composition can additionally comprise direct dyes other than anionic acid direct dyes or cationic direct dyes possessing an endocyclic cationic charge.
• These other direct dyes of use according to the invention are chosen, for example, from neutral or cationic nitro direct dyes, neutral or cationic azo direct dyes, neutral or cationic azomethine dyes, neutral or cationic quinone and in particular anthraquinone direct dyes, neutral or cationic azine direct dyes, cationic triarylmethane direct dyes, neutral or cationic indoamine direct dyes and natural or anionic direct dyes and cationic direct dyes possessing an exocyclic cationic charge.
• benzene direct dyes without implied limitation, of the following compounds: 1, 4-diamino-2-nitrobenzene, l-amino-2-nitro-4- ( ⁇ - hydroxyethylamino) benzene, l-amino-2-nitro-4- (bis ( ⁇ - hydroxyethyl) amino) benzene, 1, 4-bis ( ⁇ -hydroxyethyl- amino) -2-nitrobenzene, 1- ( ⁇ -hydroxyethylamino) -2-nitro- 4- (bis ( ⁇ -hydroxyethyl) amino) benzene, 1- ( ⁇ -hydroxyethylamino) -2-nitro-4-aminobenzene, 1- ( ⁇ -hydroxyethylamino) - 2-nitro-4- (ethyl ( ⁇ -hydroxyethyl) amino) benzene, 1-amino- 3-methyl-4- ( ⁇ -hydroxyethylamino) -6-nitrobenzene, 1- amino-2-nitro-4- ( ⁇
• Acid Yellow 9 Acid Black 1, Acid Yellow 36, Acid Orange 7, Acid Red 33, Acid Red 35, Acid Yellow 23 and Acid Orange 24.
• Basic Red 76 Basic Yellow 57, Basic Brown 16, Basic Brown 17, Basic Red 51, Basic Orange 31 and Basic Yellow 87.
• Disperse Red 15 Solvent Violet 13, Acid Violet 43, Disperse Violet 1, Disperse Violet 4, Disperse Blue 1, Disperse Violet 8, Disperse Blue 3, Disperse Red 11, Acid Blue 62, Disperse Blue 7, Basic Blue 22 and Disperse Violet 15; and of the following compounds: l-aminopropylamino-4- (methylamino) anthraquinone,
• the additional direct dye or dyes particularly represent from 0.001 to 20% by weight approximately of the total weight of the composition and preferably from 0.005 to 10% by weight approximately. More particularly, the additional direct dye or dyes represent from 0.01 to 5% by weight.
• composition of the present invention can furthermore comprise oxidation bases and couplers conventionally used for colouring by oxidation.
• Mention may be made, by way of example, of para- phenylenediamines, bisphenylalkylenediamines, para- aminophenols, ortho-aminophenols, heterocyclic bases and their addition salts.
• the couplers are, for example, meta-phenylenediamine couplers, meta-aminophenol couplers, meta-diphenol couplers, naphthalene couplers, heterocyclic couplers, and their addition salts.
• the oxidizing agent of use in the oxidation colouring is preferably chosen from hydrogen peroxide, urea hydrogen peroxide, alkali metal bromates or ferrocyanides, or persalts, such as perborates and persulphates .
• the use of hydrogen peroxide is particularly preferred.
• Use may also be made, as oxidizing agent, of one or more oxidation/reduction enzymes, such as laccases, peroxidases and 2-electron oxidoreductases, such as uricase, if appropriate in the presence of their respective donor or cofactor.
• the bases and couplers are each generally present in an amount of between 0.001 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
• composition according to the invention can additionally comprise at least one compound of ceramide type.
• Ceramides or their analogues are known to protect and/or repair the skin and/or hair fibres from the attacks of the various agents and treatments mentioned above. In particular, they have a barrier effect which limits the escape of proteins and they also strengthen cuticular cohesion.
• a description has been given, for example, in Patent Applicatoin WO 00/44345 of a means for improving cosmetic properties, such as disentangling of the hair, by the application of a composition comprising a compound of ceramide type, such as N-oleoyldihydrosphingosine, in combination with a hydrogenated sunflower wax and behenyl- trimethylammonium chloride in water.
• the term "compound of ceramide type” is understood to mean ceramides and/or glycoceramides and/or pseudoceramides and/or neoceramides, which may be natural or synthetic, of formula (XXI) below.
• Ri 4 denotes: i) a saturated or unsaturated and linear or branched Ci-C 50 , preferably C 5 -C 50 , hydrocarbon radical, it being possible for this radical to be substituted by one or more hydroxyl groups optionally esterified by an acid Ri 9 COOH, with Ri 9 being a saturated or unsaturated, linear or branched, optionally mono- or polyhydroxylated Ci- C 35 hydrocarbon radical, it being possible for the hydroxyl group or groups of the R i9 radical to be esterified by a saturated or unsaturated, linear or branched, optionally mono- or polyhydroxylated Ci-C 35 fatty acid; ii) an R' '- (NR-CO) q -R' radical, with R denoting a hydrogen atom or a mono- or polyhydroxylated, preferably monohydroxylated, Ci-C 20 hydrocarbon radical; R' and R" are hydrocarbon radicals, the sum of the carbon atoms of which is between 9 and 30, R' being a
• ⁇ Ri 5 is chosen from a hydrogen atom, a radical of saccharide type, in particular a (glycosyl) n , (galactosyl) or sulphogalactosyl radical, a sulphate or phosphate residue, a phosphorylethylamine radical and a phosphorylethylammonium radical, in which n is an integer of between 1 and 4 inclusive and m is an integer of between 1 and 8 inclusive;
• ⁇ Ri6 denotes a saturated or unsaturated and hydroxylated or nonhydroxylated Ci-C 33 hydrocarbon radical, it being possible for the hydroxyl group or groups to be esterified by an inorganic acid or an acid R19COOH, R19 having the same meanings as above, and it being possible for the hydroxyl group or groups to be etherified by a (glycosyl) , (galactosyl) , sulphogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, it also being possible for Ri 6 to be substituted by one or more Ci-Ci 4 alkyl radicals; preferably, Ri 6 denotes a C15-C26 ⁇ -hydroxyalkyl radical, the hydroxyl group optionally being esterified by a C16-C30 ⁇ -hydroxy acid; ⁇ Ri 7 denotes a hydrogen atom, a saturated or unsaturated, linear or branched, optionally hydroxylated, C3-C
• the compounds of ceramide type more particularly preferred according to the invention are the compounds of formula (XXI) for which Ri 4 denotes an optionally hydroxylated alkyl or alkenyl derived from C14-C22 fatty acids; particularly, Ri 4 represents a C12-C20 alkenyl chain comprising one or two ⁇ double bonds, preferably one; Ri 5 denotes a hydrogen atom; and R16 denotes an optionally hydroxylated linear Cn-Ci 7 radical and preferably C13-C15 radical; more particularly, Ri 6 represents an alkyl group, such as methyl or ethyl, hydroxylated by one or more hydroxyl groups, preferably by one hydroxyl group.
• Ri 4 denotes an optionally hydroxylated alkyl or alkenyl derived from C14-C22 fatty acids
• Ri 4 represents a C12-C20 alkenyl chain comprising one or two ⁇ double bonds, preferably one
• Ri 5 denotes a hydrogen atom
• Such compounds are, for example:
• Use may also be made of specific mixtures, such as, for example, the mixtures of ceramide(s) 2 and of ceramide(s) 5 according to the Downing classification.
• R i4 denotes a saturated or unsaturated alkyl radical derived from C12-C22 fatty acids
• Ri 5 denotes a galactosyl or sulphogalactosyl radical
• Questamide H bis (N- hydroxyethyl-N-cetyl) malonamide
• the concentration of compounds of ceramide type can vary between 0.0001% and 20% by weight approximately, with respect to the total weight of the composition, and from between 0.001 and 10% by weight approximately and more preferably still between 0.01 and 3% by weight .
• the medium appropriate for dyeing is generally composed of water or of a mixture of water and of at least one organic solvent in order to dissolve the compounds which would not be sufficiently soluble in water.
• organic solvent for example, of lower Ci-C 4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers, such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and diethylene glycol monomethyl ether; and aromatic alcohols, such as benzyl alcohol or phenoxyethanol; and their mixtures.
• the solvents are preferably present in proportions preferably of between 1 and 40% by weight approximately, with respect to the total weight of the dyeing composition, and more preferably still between 5 and 30% by weight approximately.
• the dyeing composition in accordance with the invention can also include various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surface- active agents or their mixtures, other than the cationic surface-active agents of formula (I), anionic, cationic, nonionic, amphoteric or zwitterionic polymers or their blends, inorganic or organic thickening agents and in particular anionic, cationic, non-ionic and amphoteric polymeric associative thickeners, antioxidizing agents, penetration agents, sequestering agents, fragrances, buffers, dispersing agents, conditioning agents, such as, for example, volatile or non-volatile and modified or unmodified silicones, film-forming agents, ceramides, preserving agents or opacifying agents.
• adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surface
• composition according to the invention can also comprise one or more fatty alcohols: R""-OH, with R"" representing an alkyl or alkenyl group having from 8 to
• these fatty alcohols being introduced in the pure form or in the form of a mixture. Mention may more particularly be made, among them, of lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol and their mixtures.
• the above adjuvants are generally present in an amount of, for each of them, between 0.01 and 20% by weight, with respect to the weight of the composition.
• the pH of the dyeing composition in accordance with the invention is generally between 2 and 11.5 approximately and preferably between 6 and 11.5 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents commonly used in dyeing keratinous fibres or alternatively using conventional buffering systems .
• basifying agents by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines, such as mono-, di- and triethanolamines and their derivatives, hydroxyalkylamines, such as 2-amino-2-methylpropanol, and ethylenediamines which are oxyethylenated and/or oxypropylenated, sodium hydroxide, potassium hydroxide and the compounds of following formula (XXII) :
• T is a propylene residue optionally substituted by a hydroxyl group or a Ci-C 4 alkyl radical
• R a , R b , R c and R d which are identical or different, represent a hydrogen atom or a Ci-C 4 alkyl or a Ci-C 4 hydroxyalkyl radical.
• the acidifying agents are conventionally, by way of example, inorganic or organic acids, such as hydrochloric acid, orthophosphoric acid, carboxylic acids, such as tartaric acid, citric acid or lactic acid, or sulphonic acids.
• inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids, such as tartaric acid, citric acid or lactic acid, or sulphonic acids.
• the dyeing composition according to the invention can be provided in various formulation forms, such as in the liquid, lotion, cream or gel form or in any other form appropriate for carrying out dyeing of keratinous fibres .
• It can also be packaged under pressure in an aerosol container in the presence of a propellant and form a mousse .
• Another subject-matter of the present invention is a dyeing method starting from the composition described above.
• this dyeing method according to the invention consists in applying the composition of the invention, in leaving it to act for a leave-in time preferably varying from 1 to 60 minutes approximately and more preferably from 10 to 45 minutes approximately, then rinsing the fibres, and then optionally washing them with a shampoo, then rinsing them again and then drying them.
• compositions 1 and 2 prepared in the proportions mentioned above are applied to permed grey hair comprising 90% of white hairs.
• the hair is rinsed and dried.
• the hair coloured with these compositions exhibits good dyeing properties and a very good feel, in particular with regard to dry hair.

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