Hair compositions comprising at least one disulfide direct dye and at least one alkaline hydroxide agent and simultaneous hair shaping and dyeing processes

• US 8,097,044 B2
• Filed: 07/24/2008
• Issued: 01/17/2012
• Est. Priority Date: 07/24/2007
• Status: Active Grant

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Guerin, Frédéric, de Boni, Maxime
• Primary Examiner(s): Elhilo, Eisa
• Application Number:
  US12/219,616
• Publication Number:
  US 20090126755A1
• Time in Patent Office: 1,272 Days
• Field of Search: 840/5, 842/6, 843/2, 843/7, 856/5, 856/6, 856/7, 856/8, 857/0, 132/202, 132/208
• US Class Current: 8/405
• CPC Class Codes: A61K 8/466 containing sulfonic acid derivatives; Salts
• CPC Class Codes: A61K 8/4926 having six membered rings
• CPC Class Codes: A61K 8/494 with more than one nitrogen as the only hetero atom
• CPC Class Codes: A61K 8/4966 Triazines or their condensed derivatives
• CPC Class Codes: A61Q 5/065 Preparations for temporary colouring the hair, e.g. direct dyes

Abstract

Disclosed herein are compositions for simultaneous shaping, dyeing, and/or lightening of keratin fibers comprising at least one disulfide direct dye and at least one organic or mineral hydroxide alkaline agent. Also disclosed herein are processes for simultaneous shaping, dyeing, and/or lightening of keratin fibers using said compositions and compartmentalized devices comprising said compositions. The compositions disclosed herein may make it possible to obtain a long-lasting dyeing effect, while limiting the degradation of the keratin fibers.

Claims

1. A composition for simultaneous shaping, dyeing, and/or lightening of keratin fibers comprising, in a cosmetically acceptable medium:

at least one disulfide direct dye; and

at least one alkaline agent chosen from mineral and organic hydroxides and present in the composition in an amount such that the pH of the composition ranges from 10 to 14.

2. The composition according to claim 1, wherein the at least one disulfide direct dye is chosen from compounds of Formulae (I), (II), or (III):

3. The composition according to claim 2, wherein, in Formulae (I), (II), or (III), when p is equal to 1, X represents the sequence -(T)_t-(Y)_y—

(Z)_z—

, and when p′

is equal to 1, X′

represents the sequence -(T)_t-(Y)_y—

(Z)_z—

, said sequence being present in Formulae (I), (II) or (III) as follows;

A-(T)_t-(Y)_y—

(Z)_z-C_aat or C′

_sat-(T)_t-(Y)_y—

(Z)_z-K, wherein;

i) T is chosen from —

SO₂—

, —

O—

, —

S—

, —

N(R)—

, —

N⁺(R)(R′

), and —

CO—

, and combinations thereof, wherein R and R″

are, independently of one another, chosen from hydrogen atoms, C₁-C₄ alkyl radicals, and C₁-C₄ hydroxyalkyl radicals; and

the coefficient t is chosen from 0 and 1;

ii) Y is chosen from;

radicals chosen from —

(CH₂)₂—

SO₂— and

—

CH₂—

CHR—

CO—

NR′

—

radicals wherein R and R″

are, independently of one another, chosen from hydrogen atoms and C₁-C₄ alkyl radicals;

groups of formula (a), (a′

), or (a″

);

4. The composition according to claim 2, wherein Y is chosen from the groups:

5. The composition according to claim 2, wherein Z is chosen from:

6. The composition according to claim 2, wherein the at least one disulfide direct dye of formula (I) is chosen such that v is equal to 0.

7. The composition according to claim 2, wherein, in Formulae (I), (II), or (III), A and A′

are chosen from radicals comprising at least one chromophore derived from dyes of the following type;

acridines, acridones, anthranthrones, anthrapyrimidines, anthraquinones, azines, azos, azomethines, benzanthrones, benzimidazoles, benzimidazolones, benzindoles, benzoxazoles, benzopyrans, benzothiazoles, benzoquinones, bisazines, bisisoindolines, carboxanilides, coumarins, cyanins, diazines, diketopyrrolopyrroles, dioxazines, diphenylamines, diphenylmethanes, dithiazines, flavonoids, fluorindines, formazans, hydrazones, hydroxy ketones, indamines, indanthrones, indigoids and pseudo-indigoids, indophenols, indoanilines, isoindolines, isoindolinones, isoviolanthrones, lactones, methines, naphthalimides, naphthanilides, naphtholactams, naphthoquinones, nitro dyes, oxadiazoles, oxazines, perilones, perinones, perylenes, phenazines, phenothiazines, phthalocyanin, polyenes/carotenoids, porphyrins, pyranthrones, pyrazolanthrones, pyrazolones, pyrimidinoanthrones, pyronines, quinacridones, quinolines, quinophthalones, squaranes, stilbenes, tetrazoliums, thiazines, thioindigo, thiopyronines, triarylmethanes and xanthenes.

8. The composition according to claim 7, wherein, in Formulae (I), (II), or (III), A and A′

are chosen from radicals comprising a chromophore chosen from chromophores of the azo, anthraquinone, and hydrazone type.

9. The composition according to claim 1, wherein the at least one disulfide direct dye is chosen from:

10. The composition according to claim 2, wherein, in Formulae (I), (II), or (III), at least one of A and A′

comprises a cationic chromophore.

11. The composition according to claim 10, wherein the cationic chromophore comprises a cationic radical which is a quaternary ammonium.

12. The composition according to claim 2, wherein the at least one disulfide direct dye is a dye of Formula (I), (II), or (III) in which at least one of A and A′

is chosen from radicals comprising one or more cationic or non-cationic fluorescent chromophores.

13. The composition according to claim 12, wherein at least one of A and A′

comprises a styryl chromophore.

14. The composition according to claim 2, wherein X and X′

are, independently of one another, chosen from —

N(R)—

groups.

15. The composition according to claim 2, wherein the at least one disulfide direct dye is chosen such that v or v′

is equal to 0, and A and A′

are, independently of one another, chosen from W—

N═

N—

Ar—

, —

W—

N═

N—

Ar, W—

C(R^c)═

C(R^d)—

Ar—

, and —

W—

C(R^c)═

C(R^d)—

Ar groups, wherein W is chosen from fused and non-fused, aromatic and non-aromatic heterocycles comprising a quaternary ammonium;

Ar is chosen from (hetero)aryl radicals having from 5 to 6 ring members, and (hetero)aromatic bicyclic rings of naphthyl, benzopyridinium, indolinyl, or benzoindolinyl type, optionally substituted with at least one group chosen from halogen atoms, alkyl groups, hydroxyl groups, alkoxy groups, hydroxyalkyl groups, amino and (di)alkylamino groups, acylamino groups;

heterocycloalkyl and heteroaryl groups having from 5 to 6 ring members; and

wherein R^c and R^d are, independently of one another, chosen from hydrogen atoms and C₁-C₄ alkyl groups.

16. The composition according to claim 15, wherein W is chosen from imidazolium, pyridinium, benzopyridinium, benzimidazolium, quinolinium, pyrazolium, and benzothiazolium groups.

17. The composition according to claim 1, wherein the at least one disulfide direct dye is chosen from:

18. The composition according to claim 1, wherein the at least one disulfide direct dye is chosen from:

19. The composition according to claim 1, wherein the at least one disulfide direct dye is chosen from:

20. The composition according to claim 1, wherein the at least one alkaline agent chosen from mineral and organic hydroxides is chosen from the hydroxides of alkali metals, alkaline-earth-metals, transition metals, lanthanides, and actinides, ammonium and guanidine hydroxides, and mixtures thereof.

21. The composition according to claim 20, wherein the at least one alkaline agent is chosen from sodium, potassium, calcium, and guanidine hydroxides, and mixtures thereof.

22. The composition according to claim 1, the at least one alkaline agent is present in the composition in an amount ranging from 0.5 to 10% by weight relative to the weight of the composition.

23. The composition according to claim 1, comprising from 0.001 to 10% by weight of disulfide direct dye(s) relative to the total weight of the composition.

24. The composition according to claim 1, wherein the cosmetically acceptable medium is a medium comprising water and optionally at least one organic solvent.

25. The composition according to claim 24, wherein the at least one organic solvent is chosen from C₁-C₄ lower alkanols, polyols, polyol ethers, aromatic alcohols, and mixtures thereof.

26. The composition according to claim 24, comprising from 1 to 40% by weight of the at least one organic solvent, relative to the total weight of the composition.

27. The composition according to claim 1, further comprising at least one inert organic liquid phase.

28. The composition according to claim 27, wherein the at least one inert organic liquid phase is chosen from polydecenes of formula C_10nH_[(20n)+2] wherein n varies from 3 to 9, esters, esters and diesters of sugars and of C₁₂-C₂₄ fatty acids, and cyclic esters, cyclic ethers, silicone oils, mineral oils, plant oils, and mixtures thereof.

29. The composition according to claim 27, wherein the at least one inert organic liquid phase is present in the composition in an amount ranging from 5 to 60% by weight, relative to the total weight of the composition.

30. The composition according to claim 1, further comprising at least one surfactant chosen from non-ionic, anionic, cationic, and amphoteric surfactants, and mixtures thereof.

31. The composition according to claim 30, wherein the at least one surfactant is present in an amount ranging from 0.5 to 30% by weight, relative to the total weight of the composition.

32. The composition according to claim 1, further comprising at least one additional direct dye of non-ionic, cationic, or anionic nature, wherein said additional direct dye does not comprise a disulfide bond.

33. The composition according to claim 32, comprising from 0.0005 to 12% by weight of additional direct dye(s), relative to the total weight of the composition.

34. A process for simultaneous shaping, dyeing, and/or lightening of keratin fibers, comprising:

applying a composition for treating keratin fibers to the keratin fibers for a sufficient time to obtain a desired shaping and dyeing, and/or lightening, and the optional rinsing and washing of the keratin fibers;

wherein the composition for treating keratin fibers comprises, in a cosmetically acceptable medium;

at least one disulfide direct dye; and

at least one alkaline agent chosen from mineral and organic hydroxides and present in the composition in an amount such that the pH of the composition ranges from 10 to 14; and

shaping the keratin fibers.

35. The process according to claim 34, comprising the following steps:

a) the composition for treating keratin fiber is applied to the fibers;

b) the fibers are subjected to a mechanical shaping operation that makes it possible to give them a new shape;

c) the composition is left on for a time ranging from 10 to 30 minutes;

d) optionally, a smoothing operation is carried out; and

e) the hair is rinsed.

36. The process according to claim 34, wherein the composition for treating keratin fibers is applied to fibers having a tone level of less than or equal to 6.

37. The process according to claim 34, wherein the keratin fibers are artificially pigmented or colored.

38. A multi-compartment device, comprising at least one first compartment (i) comprising at least one alkaline agent chosen from mineral and organic hydroxides is chosen from the hydroxides of alkali metals, alkaline-earth-metals, transition metals, lanthanides, and actinides, ammonium and guanidine hydroxides, and mixtures thereof;

and at least one second compartment (ii) comprising a composition comprising at least one disulfide direct dye;

the pH of the mixture of the contents of the various compartments ranging from 10 to 14.

39. A multi-compartment device, comprising at least one first compartment (i) comprising guanidine carbonate and at least one disulfide direct dye;

and at least one second compartment (ii) comprising at least one alkaline agent chosen from alkali metal and alkaline-earth metal hydroxides;

the pH of the mixture of the contents of the various compartments ranging from 10 to 14.

40. A multi-compartment device, comprising at least one first compartment (i) comprising guanidine carbonate;

at least one second compartment (ii) comprising at least one alkaline agent chosen from alkali metal and alkaline-earth metal hydroxides; and

at least a third compartment (iii) comprising at least one disulfide direct dye;

the pH of the mixture of the contents of the various compartments ranging from 10 to 14.