Cosmetic composition containing sulphinic acid derivatives

• US 20050008589A1
• Filed: 09/23/2002
• Published: 01/13/2005
• Est. Priority Date: 09/26/2001
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Lagrange, Alain, Legrand, Frederic
• Application Number:
  US10/490,622
• Publication Number:
  US 20050008589A1
• Time in Patent Office: Days
• US Class Current: 424/62
• CPC Class Codes: A61K 2800/88 Two- or multipart kits
• CPC Class Codes: A61K 8/046 Aerosols; Foams
• CPC Class Codes: A61K 8/46 containing sulfur A61K8/44 takes precedence
• CPC Class Codes: A61Q 5/00 Preparations for care of the hair
• CPC Class Codes: A61Q 5/08 Preparations for bleaching the hair
• CPC Class Codes: C07C 315/04 by reactions not involving the formation of sulfone or sulfoxide groups

Abstract

The invention relates to a cosmetic composition, especially for bleaching human keratin fibers dyed with oxidation dyes and/or direct dyes, in particular the hair, comprising, in a cosmetically acceptable medium at a pH of between 1.5 and 9, sulfinic acid derivatives of formula (I). The invention also relates to the novel compounds of formula (I), to multi-compartment devices for dyeing and bleaching said fibers and to the bleaching process using this composition.

Claims

1-36. -36. (Canceled).

37. A cosmetic composition, comprising, in a cosmetically acceptable medium at a pH ranging from 1.5 to 9, at least one sulfinic acid derivative of formula (I):

38. The composition according to claim 37, wherein X is chosen from a hydrogen atom, alkali metal ions and ionic equivalents of alkaline-earth metals and of zinc;

Y is chosen from hydroxyl radicals and NH₂ radicals, R₁ is a CH₃ group, and R₂ is chosen from CH₃, CH₂OH and phenyl radicals.

39. The composition according to claim 38, wherein X is Na, Y is a hydroxyl radical, R₁ is a CH₃ group, and R₂ is chosen from CH₃, CH₂OH and phenyl radicals.

40. The composition according to claim 37, further comprising at least one α

-oxocarboxylic acid and/or at least one cosmetically acceptable salt thereof.

41. The composition according to claim 40, wherein the at least one α

-oxocarboxylic acid is chosen from α

-ketoglutaric acid and from alkali metal and/or alkaline-earth metal salts thereof.

42. The composition according to claim 40, wherein the at least one α

-oxocarboxylic acid is chosen from oxalic acid, glyoxalic acid, and pyruvic acid, and from alkali metals and/or alkaline-earth metal salts thereof.

43. A process for bleaching human keratin fibers comprising

applying to human keratin fibers that have previously been dyed with at least one dye chosen from oxidation dyes and direct dyes, a dye-reducing composition comprising, in an aqueous cosmetic medium that is suitable for bleaching, at a pH ranging from 1.5 to 9, at least one sulfinic acid derivative of formula (I):

wherein;

X is chosen from a hydrogen atom, monovalent metal ions, and ionic equivalents of divalent metals from groups Ia, IIa, IIb, IVa and VIIIb of the Periodic Table of Elements,

Y is chosen from hydroxyl radicals and NR₃R₄ radicals in which R₃ and R₄, which may be identical or different, are chosen from hydrogen atoms and C₁-C₆ alkyl radicals;

R₃ and R₄ may also form an aliphatic ring that may be interrupted with a hetero atom chosen from oxygen, nitrogen and sulfur atoms,

R₁ and R₂, which may be identical or different, are chosen from C₁-C₆ alkyl radicals, C₁-C₆ hydroxyalkyl radicals, C₁-C₆ alkenyl radicals, C₁-C₆ cycloalkyl radicals, and aryl radicals optionally substituted with 1 to 3 radicals, which may be identical or different, chosen from hydroxyl radicals, C₁-C₆ alkyl radicals, C₁-C₆ alkoxy radicals, halogens and CF₃ radicals;

R₁ and R₂ may also form a 5- or 6-membered cycloalkane ring optionally substituted with at least one radical chosen from C₁-C₆ alkyl and C₁-C₆ alkoxy radicals.

44. The process according to claim 43, wherein the human keratin fibers are hair.

45. The process according to claim 43, wherein the pH ranges from 1.8 to 6.

67. The process according to claim 43, wherein said dye-reducing composition is obtained by extemporaneous mixing, at the time of use, of an anhydrous composition comprising at least one sulfinic acid derivative of formula (I) as defined in claim 43 with an aqueous composition at a pH ranging from 1.5 to 9.

68. The process according to claim 43, wherein said dye-reducing composition is obtained by extemporaneous mixing, at the time of use, of at least two aqueous compositions, at least one of which comprises at least one sulfinic acid derivative of formula (I) as defined in claim 43, at acidic or alkaline pH, and wherein at least one other comprises an aqueous composition at acidic pH.

46. A composition for bleaching human keratin fibers, wherein the fibers have been dyed with at least one dye chosen from oxidation dyes and direct dyes, comprising, in an aqueous cosmetic medium that is suitable for bleaching, at a pH ranging from 1.5 to 9, at least one dye reducing agent chosen from sulfinic acid derivatives of formula (I):

47. The composition according to claim 46, wherein the human keratin fibers are hair.

48. The composition according to claim 46, wherein the reducing agent further comprises at least one α

-oxocarboxylic acid, and/or at least one cosmetically acceptable salt thereof.

49. The composition according to claim 48, wherein the at least one α

-oxocarboxylic acid is chosen from α

-ketoglutaric acid and from alkali metal and/or alkaline-earth metal salts thereof.

50. The composition according to claim 48, wherein the at least one α

-oxocarboxylic acid is chosen from oxalic acid, glyoxalic acid, and pyruvic acid, and from alkali metals and/or alkaline-earth metal salts thereof.

51. The composition according to claim 46, wherein the pH ranges from 1.8 to 6.

52. The composition according to claim 46, wherein the at least one sulfinic acid derivative of formula (I) is present in an amount ranging from 0.01% to 20% by weight, relative to the total weight of the composition.

53. The composition according to claim 52, wherein the at least one sulfinic acid derivative of formula (I) is present in an amount ranging from 0.1% to 10% by weight, relative to the total weight of the composition.

54. The composition according to claim 46, further comprising at least one thickener.

55. The composition according to claim 54, wherein the thickener is chosen from cellulose derivatives, guar derivatives, gums of microbial and plant origin, and synthetic thickeners.

56. The composition according to claim 54, wherein the at least one thickener is present in an amount ranging from 0.01% to 10% by weight, relative to the total weight of the composition.

57. The composition according to claim 46, further comprising at least one acidifying or basifying agent in an amount ranging from 0.01% to 30% by weight, relative to the total weight of the composition.

58. The composition according to claim 57, wherein the at least one acidifying agent is chosen from mineral and organic acids.

59. The composition according to claim 58, wherein the mineral and organic acids are chosen from etidronic acid, hydrochloric acid, orthophosphoric acid, carboxylic acids, and sulfonic acids.

60. The composition according to claim 59, wherein the carboxylic acids are chosen from tartaric acid, citric acid and lactic acid.

61. The composition according to claim 57, wherein the at least one basifying agent is chosen from aqueous ammonia, alkaline carbonates, alkanolamines, 2-methyl-2-amino-1-propanol and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (III):

62. The composition according to claim 61, wherein the alkanolamines are chosen from monoethanolamine, diethanolamine and triethanolamine.

63. The composition according to claim 46, wherein the composition is obtained by extemporaneous mixing, at the time of use, of an anhydrous composition comprising at least one sulfinic acid derivative of formula (I) as defined in claim 46 with an aqueous composition at a pH ranging from 1.5 to 9.

64. The bleaching composition according to claim 63, wherein said aqueous composition has a pH ranging from 1.8 to 6.

65. The bleaching composition according to claim 46, wherein said composition is obtained by extemporaneous mixing, at the time of use, of at least two aqueous compositions, at least one of which comprises at least one sulfinic acid derivative of formula (I) as defined in claim 50, at acidic or alkaline pH, and wherein the at least one other comprises an aqueous composition at acidic pH.

66. The composition according to claim 46, wherein it is in the form of a gel, a cream, a mousse, a solution or an emulsion.

69. A multi-compartment kit for dyeing and then for bleaching human keratin fibers previously dyed with oxidation dyes and/or direct dyes, comprising

at least one first compartment comprising at least one dyeing composition chosen from oxidation dyeing compositions and non-oxidation dyeing compositions for keratin fibers, and

at least one second compartment comprising a composition for the reductive bleaching of the dyed fibers comprising, in an aqueous cosmetic medium that is suitable for bleaching, at a pH ranging from 1.5 to 9, at least one dye reducing agent chosen from sulfinic acid derivatives of formula (I):

wherein;

X is chosen from a hydrogen atom, monovalent metal ions, and ionic equivalents of divalent metals from groups Ia, IIa, IIb, IVa and VIIIb of the Periodic Table of Elements,

Y is chosen from hydroxyl radicals and NR₃R₄ radicals in which R₃ and R₄, which may be identical or different, are chosen from hydrogen atoms and C₁-C₆ alkyl radicals;

R₃ and R₄ may also form an aliphatic ring that may be interrupted with a hetero atom chosen from oxygen, nitrogen and sulfur atoms,

R₁ and R₂, which may be identical or different, are chosen from C₁-C₆ alkyl radicals, C₁-C₆ hydroxyalkyl radicals, C₁-C₆ alkenyl radicals, C₁-C₆ cycloalkyl radicals, and aryl radicals optionally substituted with 1 to 3 radicals, which may be identical or different, chosen from hydroxyl radicals, C₁-C₆ alkyl radicals, C₁-C₆ alkoxy radicals, halogens and CF₃ radicals;

R₁ and R₂ may also form a 5- or 6-membered cycloalkane ring optionally substituted with at least one radical chosen from C₁-C₆ alkyl and C₁-C₆ alkoxy radicals.

70. The multi-compartment kit according to claim 69, wherein the human keratin fibers are hair.

71. The multi-compartment kit according to claim 69, wherein, in the at least one first compartment, the at least one oxidation dyeing composition comprises oxidation bases and/or couplers that form an oxidation dye when mixed with at least one oxidizing agent.

72. The multi-compartment kit according to claim 71, wherein, in the at least one first compartment, the at least one oxidation dyeing composition also comprises at least one direct dye.

73. The multi-compartment kit according to claim 72, wherein the at least one direct dye forms a lightening direct dye by mixing with at least one oxidizing agent.

74. The multi-compartment kit according to claim 73, wherein the at least one direct dye is chosen from cationic direct dyes.

75. The multi-compartment kit according to claim 69, wherein the at least one non-oxidation dyeing composition comprises at least one direct dye.

76. The multi-compartment kit according to claim 75, wherein the at least one direct dye is chosen from cationic direct dyes.

77. The multi-compartment kit according to claim 74 or 76, wherein the cationic direct dyes are chosen from the dyes of formulae (I) to (VII), and the mesomeric forms thereof:

78. The multi-compartment kit according to claim 77, wherein the halogens are chosen from bromine, chlorine, iodine and fluorine.

79. The multi-compartment kit according to claim 77, wherein J is chosen from 5- or 6-membered nitrogenous heterocyclic radicals of structure J₂:

80. A process for bleaching human keratin fibers previously dyed with oxidation dyes and/or direct dyes, comprising

applying to human keratin fibers that have previously been dyed with at least one dye chosen from oxidation dyes and direct dyes, a dye-reducing composition comprising, in an aqueous cosmetic medium that is suitable for bleaching, at a pH ranging from 1.5 to 9, at least one sulfinic acid derivative of formula (I):

wherein;

X is chosen from a hydrogen atom, monovalent metal ions, and ionic equivalents of divalent metals from groups Ia, IIa, IIb, IVa and VIIIb of the Periodic Table of Elements,

Y is chosen from hydroxyl radicals and NR₃R₄ radicals in which R₃ and R₄, which may be identical or different, are chosen from hydrogen atoms and C₁-C₆ alkyl radicals;

R₃ and R₄ may also form an aliphatic ring that may be interrupted with a hetero atom chosen from oxygen, nitrogen and sulfur atoms,

R₁ and R₂, which may be identical or different, are chosen from C₁-C₆ alkyl radicals, C₁-C₆ hydroxyalkyl radicals, C₁-C₆ alkenyl radicals, C₁-C₆ cycloalkyl radicals, and aryl radicals optionally substituted with 1 to 3 radicals, which may be identical or different, chosen from hydroxyl radicals, C₁-C₆ alkyl radicals, C₁-C₆ alkoxy radicals, halogens and CF₃ radicals;

R₁ and R₂ may also form a 5- or 6-membered cycloalkane ring optionally substituted with at least one radical chosen from C₁-C₆ alkyl and C₁-C₆ alkoxy radicals,

wherein the composition is applied to the fibers at an application temperature ranging from room temperature to 80°

C., and left on the fibers for a time that is sufficient to partially or totally strip the dye from the fibers.

81. The process according to claim 80, wherein the human keratin fibers are hair.

82. The process according to claim 80, wherein the application temperature ranges from 35°

C. to 50°

C.

83. The process according to claim 80, wherein the time that is sufficient to partially or totally strip the dye from the fibers ranges from 1 to 60 minutes.

84. The process according to claim 83, wherein the time that is sufficient to partially or totally strip the dye from the fibers ranges from 5 to 30 minutes.

85. A compound of formula (I):

86. A compound of formula (I) below: