COMPOSITION FOR DYEING KERATIN FIBRES COMPRISING A DIRECT DYE BEARING A DISULPHIDE/THIOL FUNCTION, A NONIONIC SURFACTANT, AN AMPHOTERIC SURFACTANT, AN ETHOXYLATED FATTY ALCOHOL, AN ALKALINE AGENT AND A REDUCING AGENT

• US 20140137342A1
• Filed: 02/17/2012
• Published: 05/22/2014
• Est. Priority Date: 02/25/2011
• Status: Active Grant

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Guerin, Frdric, Pourille, Chrystel
• Granted Patent: US 9,265,705 B2
• Time in Patent Office: Days
• US Class Current: 8/405
• CPC Class Codes: A61K 2800/4322 in preparations for temporarily coloring the hair further containing an oxidizing agent
• CPC Class Codes: A61K 2800/596 Mixtures of surface active compounds
• CPC Class Codes: A61K 2800/882 Mixing prior to application
• CPC Class Codes: A61K 8/41 Amines
• CPC Class Codes: A61K 8/442 substituted by amido group(s)
• CPC Class Codes: A61K 8/46 containing sulfur A61K8/44 takes precedence
• CPC Class Codes: A61K 8/49 containing heterocyclic compounds
• CPC Class Codes: A61K 8/4926 having six membered rings
• CPC Class Codes: A61K 8/4933 having sulfur as an exocyclic substituent, e.g. pyridinethione
• CPC Class Codes: A61K 8/494 with more than one nitrogen as the only hetero atom
• CPC Class Codes: A61K 8/4946 Imidazoles or their condensed derivatives, e.g. benzimidazoles
• CPC Class Codes: A61K 8/604 Alkylpolyglycosides; Derivatives thereof, e.g. esters
• CPC Class Codes: A61Q 5/065 Preparations for temporary colouring the hair, e.g. direct dyes
• CPC Class Codes: A61Q 5/10 Preparations for permanently dyeing the hair

Abstract

The invention relates to a process for dyeing and/or lightening keratin fibres such as the hair, using i) at least one direct dye bearing a disulfide, thiol or protected-thiol function and ii) at least one nonionic surfactant, iii) at least one amphoteric surfactant, iv) at least one alkaline agent, and v) at least one reducing agent. The invention also relates to a composition comprising the ingredients i) to v), to the use of the combination of i), ii), iii), iv) and v) for the dyeing and/or lightening of keratin fibres, and to a multi-compartment kit comprising the ingredients i) to v). The dyeing process and the composition according to the invention especially afford a long-lasting coloration on keratin fibres, which is strong, chromatic and/or homogeneous, with or without the use of an oxidizing agent.

Claims

1-23. -23. (canceled)

24. A cosmetic composition comprising:

i) at least one direct dye chosen from dyes of formula (I), comprising at least one functional group chosen from disulfide, thiol, and protected-thiol functional groups;

A-(X)_p—

C_sat—

S—

U 

 

(I)

the salts thereof with an organic or mineral acid, optical or geometric isomers thereof, tautomers thereof, and solvates thereof,

wherein;

U is a radical chosen from;

a) —

S—

C′

_sat—

(X′

)_p′

-A′

; and

b) —

Y;

A and A′

, which may be identical or different, are chosen from radicals comprising at least one quaternized cationic chromophore and radicals comprising at least one chromophore bearing a quaternized or quaternizable cationic group;

Y is chosen from i) hydrogen; and

ii) thiol-function protecting groups;

X and X′

, which may be identical or different, are chosen from linear or branched, saturated or unsaturated divalent C₁-C₃₀ hydrocarbon-based chains, optionally interrupted and/or optionally terminated at one or both of its ends with at least one divalent group chosen from;

—

N(R)—

, —

N⁺(R)(R)—

, —

O—

, —

S—

, —

CO—

, and —

SO₂—

wherein R, which may be identical or different, is chosen from hydrogen and C₁-C₄ alkyl, hydroxyalkyl, and aminoalkyl radicals;

aromatic or non-aromatic, saturated or unsaturated, fused or non-fused (hetero)cyclic radicals optionally comprising at least one identical or different, optionally substituted heteroatom;

p and p′

, which may be identical or different, are equal to 0 or 1;

C_sat and C′

_sat, which may be identical or different, are chosen from optionally cyclic, optionally substituted linear or branched C₁-C₁₈ alkylene chains;

ii) at least one nonionic surfactant;

iii) at least one amphoteric surfactant;

iv) at least one alkaline agent; and

v) at least one reducing agent.

25. The composition according to claim 24, wherein the radicals A and/or A′

of the at least one direct dye of formula (I), which may be identical or different, are chosen from radicals comprising at least one quaternized cationic chromophore.

26. The composition according to claim 24, wherein the at least one direct dye of formula (I) is a disulfide dye, wherein U is a radical a) —

S—

C′

_sat—

(X′

)_p′

-A′

.

27. The composition according to claim 26, wherein the at least one direct dye of formula (I) is a symmetrical disulfide dye of the following formula (Ia):

A-(X)_p—

C_sat—

S—

S—

C′

_sat—

(X′

)_p′

-A′

 

 

(Ia)

wherein A=A′

, X=X′

, p=p′

, and C_sat=C′

_sat.

28. The composition according to claim 24, wherein the at least one direct dye of formula (I) is a dye comprising a thiol or protected-thiol function, wherein U is the radical b) Y, chosen from hydrogen and the following radicals:

(C₁-C₄)alkylcarbonyl;

(C₁-C₄)alkylthiocarbonyl;

(C₁-C₄)alkoxycarbonyl;

(C₁-C₄)alkoxythiocarbonyl;

(C₁-C₄)alkylthio-thiocarbonyl;

(di)(C₁-C₄)(alkyl)aminocarbonyl;

(di)(C₁-C₄)(alkyl)aminothiocarbonyl;

arylcarbonyl, for instance phenylcarbonyl;

aryloxycarbonyl;

aryl(C₁-C₄)alkoxycarbonyl;

(di)(C₁-C₄)(alkyl)aminocarbonyl;

(C₁-C₄)(alkyl)arylaminocarbonyl;

carboxyl;

SO₃⁻

;

M⁺ wherein M⁺ is chosen from alkali metal ions, or alternatively a counterion of the cationic chromophore A and M⁺ are absent;

optionally substituted aryl;

optionally substituted heteroaryl;

optionally cationic, optionally substituted heterocycloalkyl;

—

C(NR′

^cR′

^d)═

N⁺R′

^eR′

^f;

An′

″

⁻

wherein R′

^c, R′

^d, R′

^e and R′

^f, which may be identical or different, are chosen from hydrogen atom and (C₁-C₄)alkyl groups and An′

″

⁻

is a counterion;

—

C(NR′

^cR′

^d)═

NR′

^e;

wherein R′

^c, R′

^d and R′

^e are defined above;

optionally substituted (di)aryl(C₁-C₄)alkyl;

optionally substituted (di)heteroaryl(C₁-C₄)alkyl;

CR¹R²R³ wherein R¹, R² and R³, which may be identical or different, are chosen from halogen and the following groups;

(C₁-C₄)alkyl;

(C₁-C₄)alkoxy;

optionally substituted aryl;

optionally substituted heteroaryl;

P(Z¹)R′

¹R′

²R′

³ wherein R′

¹ and R′

², which may be identical or different, are chosen from hydroxyl, (C₁-C₄)alkoxy and alkyl groups, and Z¹ is chosen from oxygen and sulfur;

sterically hindered rings; and

optionally substituted alkoxyalkyl.

29. The composition according to claim 24, wherein, in formula (I), C_sat and C′

_sat, which may be identical or different, are chosen from —

(CH₂)_k—

chains wherein k is an integer ranging from 1 to 8 inclusive.

30. The composition according to claim 24, wherein, in formula (I), when p and p′

are equal to 1, X and X′

, which may be identical or different, are chosen from the following sequence;

-(T)_t-(Z)_z-(T′

)_t′

-

wherein the sequence is linked in formula (I) symmetrically as follows;

C_sat(or C′

_sat)-(T)_t-(Z)_z-(T′

)_t′

-(A or A′

);

wherein;

T and T′

, which may be identical or different, are chosen from at least one of;

—

O—

;

—

S—

;

—

N(R)—

;

—

N⁺(R)(R^o)—

;

—

S(O)—

;

—

S(O)₂—

; and

—

C(O)—

;

wherein R, R^o, which may be identical or different, are chosen from hydrogen, C₁-C₄ alkyl radicals, C₁-C₄ hydroxyalkyl radicals and aryl(C₁-C₄)alkyl radicals; and

a cationic or non-cationic, optionally monocyclic heterocycloalkyl or heteroaryl radical, optionally comprising two heteroatoms;

t and t′

, which may be identical or different, are equal to 0 or 1;

Z is chosen from;

—

(CH₂)_m—

radicals wherein m is an integer ranging from 1 to 8 inclusive;

—

(CH₂CH₂O)_q— and

—

(OCH₂CH₂)_q—

wherein q is an integer ranging from 1 to 5 inclusive;

aryl, alkylaryl and arylalkyl radicals wherein the alkyl radical is chosen from C₁-C₄ alkyl radicals, optionally substituted with at least one group SO₃M wherein M is chosen from hydrogen, alkali metal ions and ammonium groups substituted with at least one identical or different, linear or branched C₁-C₁₈ alkyl radical optionally bearing at least one hydroxyl group;

z is 0 or 1.

31. The composition according to claim 24, wherein the at least one direct dye of formula (I) comprises a chromophore A and optionally a chromophore A′

, wherein A and A′

may be identical or different and are chosen from the hydrazono cationic chromophores of formulae (II) and (III′

), the azo chromophores of formulae (IV) and (IV′

) and the diazo chromophores of formulae (V) and (V′

) below;

(*)-Het⁺-C(R^a)═

N—

N(R^b)—

Ar,Q⁻

 

 

(II)

Q⁻

,Het⁺-C(R^a)═

N—

N(R^b)—

Ar′

-(*), 

 

(II′

)

(*)-Het⁺-N(R^a)—

N═

C(R^b)—

Ar,Q⁻

 

 

(III)

Q⁻

,Het⁺-N(R^a)—

N═

C(R^b)—

Ar′

-(*), 

 

(III′

)

(*)-Het⁺-N═

N—

Ar,Q⁻

 

 

(IV)

Q⁻

,Het⁺-N═

N—

Ar′

-(*) 

 

(IV′

)

(*)-Ar⁺—

N═

N—

Ar″

,Q⁻

 

 

(V)

Q⁻

,Ar⁺—

N═

N—

Ar″

-(*) 

 

(V′

)

wherein;

Het⁺ is a cationic heteroaryl radical;

Ar⁺ is an aryl radical bearing an exocyclic cationic charge;

Ar is an optionally substituted aryl group;

Ar′

is an optionally substituted divalent (hetero)arylene group;

Ar″

is an optionally substituted (hetero)aryl group;

R^a and R^b, which may be identical or different, are chosen from hydrogen and optionally substituted (C₁-C₈)alkyl groups;

or alternatively the substituent R^a with a substituent of Het⁺ and/or R^b with a substituent of Ar form, together with the atoms that bear them, a (hetero)cycloalkyl;

Q⁻

is chosen from organic or mineral anionic counterions;

(*) represents the part of the chromophore linked to the rest of the molecule of formula (I).

32. The composition according to claim 24, wherein the at least one direct dye of formula (I) comprises a chromophore A and optionally a chromophore A′

, wherein A and A′

may be identical or different and are chosen from;

a) polymethinyl radicals of formulae (VI) and (VI′

) below;

W⁺—

[C(R^c)═

C(R^d)]_m′

—

Ar′

-(*)Q⁻

 

 

(VI)

Ar—

[C(R^d)═

C(R^c)]_m′

—

W′

⁺-(*)Q⁻

 

 

(VI′

)

wherein;

W⁺ is chosen from cationic heterocyclic and heteroaryl groups;

W′

⁺ is chosen from divalent heterocyclic and heteroaryl radicals as defined for W⁺;

Ar is an optionally substituted aryl group;

Ar′

is a divalent aryl radical as defined for Ar;

m′

is an integer ranging from 1 to 4 inclusive;

R^c and R^d, which may be identical or different, are chosen from hydrogen and optionally substituted (C₁-C₈)alkyl groups, or alternatively R^c contiguous with W⁺ or W′

⁺ and/or R^d contiguous with Ar or Ar′

form, together with the atoms that bear them, a (hetero)cycloalkyl;

Q⁻

is an anionic counterion;

(*) represents the part of the chromophore linked to the rest of the molecule of formula (I); and

b) naphthalimidyl radicals of formula (VII) and (VII′

) below;

33. The composition according to claim 24, wherein the at least one direct dye of formula (I) is a disulfide dyes chosen from those of formulae (VIII) to (XIV) and thiol or protected-thiol dyes chosen from those of formulae (VIII′

) to (XIV′

);

34. The composition according to claim 24, wherein the at least one direct dye of formula (I) is chosen from:

dyes of formulae (XV) and (XV′

) below;

35. The composition according to claim 24, wherein the at least one direct dye of formula (I) is chosen from dyes of the following chemical structures:

36. The composition according to claim 35, wherein An⁻

and M′

are identical and/or are chosen from halides and alkyl sulphates.

37. The composition according to claim 25, wherein the at least one direct dye of formula (I) is chosen from dyes of formulae 44, 49, 49a and 55.

38. The composition according to claim 24, wherein the at least one nonionic surfactant ii) is chosen from:

polyethoxylated, polypropoxylated and/or polyglycerolated fatty alcohols, α

-diols, and alkylphenols comprising a fatty chain;

copolymers of ethylene oxide and propylene oxide, condensates of ethylene oxide and propylene oxide on fatty alcohols;

polyethoxylated fatty amides comprising from 2 to 30 mol of ethylene oxide;

polyglycerolated fatty amides comprising on average 1 to 5 glycerol groups;

oxyethylenated fatty acid esters of sorbitan comprising from 2 to 30 mol of ethylene oxide;

fatty acid esters of sucrose;

fatty acid esters of polyethylene glycol;

alkylpolyglycosides;

N-alkylglucamine derivatives, amine oxides such as (C₁₀-C₁₄)alkylamine oxides and N-acylaminopropylmorpholine oxides.

39. The composition according to claim 38, wherein the at least one nonionic surfactant ii) is chosen from polyethoxylated, polypropoxylated and/or polyglycerolated fatty alcohols, α

-diols, and alkylphenols comprising a C₈-C₂₂ fatty chain, wherein the number of ethylene oxide and/or propylene oxide units ranges from 2 to 50 inclusive and/or the number of glycerol groups ranges from 2 to 30 inclusive.

40. The composition according to claim 38, wherein the at least one nonionic surfactant is chosen from (poly)ethoxylated fatty alcohols;

glycerolated fatty alcohols; and

alkylpolyglycosides.

41. The composition according to claim 24, wherein the at least one amphoteric surfactant iii) is chosen from (C₈-C₂₀ alkyl)betaines, (C₈-C₂₀ alkyl)amido(C₂-C₈ alkyl)betaines and compounds of formulae (XVIII) and (XIX) below:

R_a—

C(O)—

NH—

CH₂—

CH₂—

N⁺(R_b)(R_c)—

CH₂—

C(O)—

O⁻

 

 

(XVIII)

wherein in formula (XVIII);

R_a is chosen from C₁₀-C₃₀ alkyl and alkenyl groups derived from an acid R_a—

C(O)—

OH, or a heptyl, nonyl or undecyl group;

R_b is a β

-hydroxyethyl group; and

R_c is a carboxymethyl group; and

R_a′

—

C(O)—

NH—

CH₂—

CH₂—

N(B)B′

 

 

(XIX)

wherein in formula (XIX);

B is —

CH₂CH₂OX′

;

B′

is —

(CH₂)_z—

Y′

, wherein z=1 or 2;

X′

is chosen from —

CH₂—

C(O)—

OH, —

CH₂—

C(O)—

OZ′

, —

CH₂CH₂—

C(O)—

OH, —

CH₂—

CH₂—

C(O)—

OZ′

, and hydrogen;

Y′

is chosen from —

C(O)—

OH, —

C(O)—

OZ′

, —

CH₂—

CH(OH)—

SO₃H and —

CH₂—

CH(OH)—

SO₃Z′

;

Z′

is chosen from ions derived from alkali or alkaline-earth metals;

ammonium ions; and

ions derived from an organic amine;

R_a′

is chosen from C₁₀-C₃₀ alkyl and alkenyl groups of an acid R_a′

C(O)—

OH, alkyl groups, and unsaturated Cl₇ groups.

and mixtures thereof.

42. The composition according to claim 41, wherein the at least one amphoteric surfactant iii) is chosen from cocoylamidopropylbetaine and cocoylbetaine and the N-cocoylamidocarboxymethyl glycinate of an alkali metal.

43. The composition according to claim 24, wherein the at least one alkaline agent iv) is chosen from aqueous ammonia, alkali metal carbonates and bicarbonates, sodium hydroxide, potassium hydroxide, and mixtures thereof, alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and compounds of formula (XX) below:

44. The composition according to claim 43, wherein the at least one alkaline agent iv) is ethanonlamine.

45. The composition according to claim 24, wherein the at least one reducing agent v) is chosen from thioglycolic acid, thiolactic acid, 3-mercaptopropionic acid, thiomalic acid, 2,3-dimercaptosuccinic acid, cysteine, N-glycyl-L-cysteine, L-cysteinylglycine and also esters and salts thereof, thioglycerol, cysteamine and C₁-C₄ acyl derivatives thereof, N-mesylcysteamine, N-acetylcysteine, N-mercaptoalkylamides of sugars such as N-(mercapto-2-ethyl) gluconamide, pantetheine, N-(mercaptoalkyl)-ω

-hydroxyalkylamides, N-mono- or N,N-dialkylmercapto-4-butyramides, aminomercaptoalkyl amides, N-(mercaptoalkyl)succinamic acids and N-(mercaptoalkyl)succinimides, alkylamino mercaptoalkyl amides, the azeotropic mixture of 2-hydroxypropyl thioglycolate and of (2-hydroxy-1-methyl)ethyl thioglycolate, mercaptoalkylamino amides, and N-mercaptoalkylalkanediamides.

46. The composition according to claim 45, wherein the at least one reducing agent v) is chosen from thioglycolic acid, cysteine, and salts thereof.

47. A method for dyeing and/or lightening keratin fibers, comprising applying to the keratin fibers:

i) at least one direct dye of formula (I) according to claim 24;

ii) at least one nonionic surfactant;

iii) at least one amphoteric surfactant;

iv) at least one alkaline agent; and

v) at least one reducing agent; and

vi) optionally at least one chemical oxidizing agent; and

vii) optionally at least one thickening organic polymer;

wherein the ingredients i) to vii) are applied to the keratin fibers together or separately.

48. The method according to claim 47, wherein a composition according to claim 24 is applied to the keratin fibers.

49. The method according to claim 47, comprising applying to the keratin fibers a reducing composition comprising iv) at least one alkaline agent and v) at least one reducing agent, followed by the application of a dye composition comprising i) at least one direct dye of formula (I), ii), at least one nonionic surfactant, iii) at least one amphoteric surfactant, and optionally vii) at least one thickening organic polymer.

50. The method according to claim 47, wherein the keratin fibers are dark keratin fibers having a tone depth of less than or equal to 6, wherein the at least one direct dye of formula (I) is chosen from:

dyes of formulae (XIII), (XIII′

), (XIV), and (XIV′

), as defined in claim 33; and

dyes of formulae (XV), (XV′

), (XVI), and (XVI′

), as defined in claim 34.

51. The method according to claim 50, wherein the at least one direct dye of formula (I) is chosen from dyes of the following chemical structures:

52. A multi-compartment dyeing device or kit for dyeing keratin fibers comprising:

a first compartment comprising a dye composition comprising at least one direct dye of formula (I) according to claim 24;

a second compartment comprising v) at least one reducing agent;

and, optionally, a third compartment comprising vi) at least one chemical oxidizing agent;

wherein the first and/or second compartment further comprises ii) at least one nonionic surfactant, iii) at least one amphoteric surfactant, iv) at least one alkaline agent, and/or vii) at least one thickening organic polymer.