USE OF PARTICULAR PYRIDINIUM SALTS FOR THE TREATMENT OF KERATIN SUBSTANCES, COMPOSITIONS AND IMPLEMENTATION METHODS

Abstract

The present invention relates to the use of one or more particular pyridinium salts for the treatment of keratin substances, particularly human keratin fibres such as hair. The invention also relates to a method for the treatment of keratin substances using said salts and optionally one or more chemical oxidizing agents. The invention also relates to a composition for lightening keratin substances comprising one or more pyridinium salts as defined hereinafter and one or more chemical oxidizing agents. The present invention also relates to one or more particular pyridinium salts and also to compositions containing them, especially compositions comprising a physiologically acceptable medium.

Claims

1.-16. (canceled)

17. A method for treating keratin substances, the method comprising applying to the keratin substances at least one compound represented by formula (I) or the addition salts or solvates thereof: ##STR00019## wherein: R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be identical or different, each represent: a hydrogen or halogen atom; a linear or branched C.sub.1-C.sub.10 alkyl substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; a linear or branched C.sub.1-C.sub.10 alkoxy substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; a —CO.sub.2R.sup.9 substituent, a —COR.sup.10 substituent, or two adjacent substituents R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4 and/or R.sup.4 and R.sup.5 can form together with the carbon atoms to which they are attached a cycloalkyl group including 5 to 10 members or an aryl group including 6 to 10 members, it being understood that said cycloalkyl or aryl group optionally comprises one or more heteroatoms and is optionally substituted by one or more halogen atoms, one or more linear or branched C.sub.1-C.sub.10 alkyl substituents, one or more linear or branched C.sub.1-C.sub.10 alkoxy substituents, one or more hydroxyl groups, one or more C.sub.1-C.sub.4 hydroxyalkyl substituents and one or more —NR.sup.7R.sup.8 groups; ALK represents a linear or branched, saturated or unsaturated C.sub.1-C.sub.10 alkyl substituent; R.sup.6 represents: a hydrogen or halogen atom, a linear or branched, saturated or unsaturated C.sub.1-C.sub.10 alkyl substituent, optionally interrupted by one or more heteroatoms chosen from oxygen and nitrogen and/or optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; an aryl substituent including 5 to 12 members optionally substituted by one or more halogen atoms, one or more linear or branched C.sub.1-C.sub.10 alkyl substituents, one or more linear or branched C.sub.1-C.sub.10 alkoxy substituents, one or more hydroxyl groups, one or more C.sub.1-C.sub.4 hydroxyalkyl substituents and one or more —NR.sup.7R.sup.8 groups; X represents a heteroatom chosen from an oxygen atom or a sulfur atom, or a —NR.sup.11 substituent; R.sup.7, R.sup.8, R.sup.9, R.sup.10, and R.sup.11, which may be identical or different, denote a hydrogen atom or a linear or branched C.sub.1-C.sub.10 alkyl substituent optionally substituted with one or more hydroxyl or C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and amino groups; wherein one of the substituents R.sup.1 or R.sup.5 may form a ring with the substituent R.sup.6. Q.sup.− represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in compounds of formula (I).

18. The method according to claim 17, characterized in that X represents an oxygen atom.

19. The method according to claim 17, characterized in that ALK represents a linear C.sub.1-C.sub.10 alkylene substituent, a linear C.sub.2-C.sub.10 alkenylene substituent or a linear C.sub.2-C.sub.10 alkylnylene substituent.

20. The method according to claim 17, characterized in that the substituents R.sup.1 and R.sup.5 represent a hydrogen atom.

21. The method according to claim 17, characterized in that the substituents R.sup.2 and R.sup.4, which may be identical or different, represent a hydrogen atom or a linear C.sub.1-C.sub.4 alkyl substituent, in particular a methyl substituent.

22. The method according to claim 17, characterized in that R.sup.3 represents a hydrogen atom or a —COR.sup.10 substituent with R.sup.10 denoting a linear C.sub.1-C.sub.10 alkyl substituent, particularly a linear C.sub.1-C.sub.4 alkyl substituent.

23. The method according to claim 17, characterized in that R.sup.7, R.sup.8, R.sup.9 and R.sup.10, which may be identical or different, denote a linear or branched C.sub.1-C.sub.10 alkyl substituent optionally substituted with one or more hydroxyl, C.sub.1-C.sub.10 alkoxy and amino groups.

24. The method according to claim 17, characterized in that the compounds(s) of formula (I) are chosen from the compounds of formula (II) and addition salts and solvates thereof: ##STR00020## in which: R.sup.1 and R.sup.5 represent a hydrogen atom; R.sup.2 and R.sup.4, which may be identical or different, represent: a hydrogen atom, a linear or branched C.sub.1-C.sub.10 alkyl substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, and —NR.sup.7R.sup.8 groups, a linear or branched C.sub.1-C.sub.10 alkoxy substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy and —NR.sup.7R.sup.8 groups, a —CO.sub.2H substituent, a —COR.sup.10 substituent, R.sup.3 represents: a hydrogen atom; a linear or branched C.sub.2-C.sub.10 alkyl substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy and —NR.sup.7R.sup.8 groups, a linear or branched C.sub.1-C.sub.10 alkoxy substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; a —CO.sub.2R.sup.9 substituent, a —COR.sup.10 substituent, ALK represents a methylene substituent, —R.sup.6 represents a methylene substituent, R.sup.7 and R.sup.8, which may be identical or different, denote a hydrogen atom or a linear or branched C.sub.1-C.sub.10 alkyl substituent optionally substituted with one or more hydroxyl, C.sub.1-C.sub.10 alkoxy and amino groups; R.sup.9 and R.sup.19, which may be identical or different, denote a linear or branched C.sub.1-C.sub.10 alkyl substituent optionally substituted with one or more hydroxyl, C.sub.1-C.sub.10 alkoxy and amino groups; Q.sup.− represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in compounds of formula (II).

25. The method according to claim 17, characterized in that the compound(s) of formula (I) are chosen from the following compounds: ##STR00021## and mixtures thereof, wherein Q.sup.− represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in said compounds.

26. The method according to claim 17, wherein the method is for improving the oxidizing activity of one or more chemical oxidizing agents.

27. A composition comprising: at least one compound represented by formula (I) or the addition salts or solvates thereof: ##STR00022## wherein: R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be identical or different, each represent: a hydrogen or halogen atom; a linear or branched C.sub.1-C.sub.10 alkyl substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; a linear or branched C.sub.1-C.sub.10 alkoxy substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; a —CO.sub.2R.sup.9 substituent, a —COR.sup.10 substituent, or two adjacent substituents R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4 and/or R.sup.4 and R.sup.5 can form together with the carbon atoms to which they are attached a cycloalkyl group including 5 to 10 members or an aryl group including 6 to 10 members, it being understood that said cycloalkyl or aryl group optionally comprises one or more heteroatoms and is optionally substituted by one or more halogen atoms, one or more linear or branched C.sub.1-C.sub.10 alkyl substituents, one or more linear or branched C.sub.1-C.sub.10 alkoxy substituents, one or more hydroxyl groups, one or more C.sub.1-C.sub.4 hydroxyalkyl substituents and one or more —NR.sup.7R.sup.8 groups; ALK represents a linear or branched, saturated or unsaturated C.sub.1-C.sub.10 alkyl substituent; R.sup.6 represents: a hydrogen or halogen atom, a linear or branched, saturated or unsaturated C.sub.1-C.sub.10 alkyl substituent, optionally interrupted by one or more heteroatoms chosen from oxygen and nitrogen and/or optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; an aryl substituent including 5 to 12 members optionally substituted by one or more halogen atoms, one or more linear or branched C.sub.1-C.sub.10 alkyl substituents, one or more linear or branched C.sub.1-C.sub.10 alkoxy substituents, one or more hydroxyl groups, one or more C.sub.1-C.sub.4 hydroxyalkyl substituents and one or more —NR.sup.7R.sup.8 groups; X represents a heteroatom chosen from an oxygen atom or a sulfur atom, or a —NR.sup.11 substituent; R.sup.7, R.sup.8, R.sup.9, R.sup.10, and R.sup.11, which may be identical or different, denote a hydrogen atom or a linear or branched C.sub.1-C.sub.10 alkyl substituent optionally substituted with one or more hydroxyl or C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and amino groups; wherein one of the substituents R.sup.1 or R.sup.5 may form a ring with the substituent R.sup.6. Q.sup.− represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in compounds of formula (I); and one or more chemical oxidizing agents.

28. The composition according to claim 27, characterized in that the chemical oxidizing agent is hydrogen peroxide.

29. The treatment method according to claim 17, wherein the one or more compounds of formula (I) are applied in the presence of one or more chemical oxidizing agents.

30. Compounds of formula (II) and addition salts and solvates thereof: ##STR00023## in which: R.sup.1 and R.sup.5 represent a hydrogen atom; R.sup.2 and R.sup.4, which may be identical or different, represent: a hydrogen atom, a linear or branched C.sub.1-C.sub.10 alkyl substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, and —NR.sup.7R.sup.8 groups, a linear or branched C.sub.1-C.sub.10 alkoxy substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, and —NR.sup.7R.sup.8 groups, a —CO.sub.2H substituent, a —COR.sup.10 substituent, R.sup.3 represents: a hydrogen atom; a linear or branched C.sub.2-C.sub.10 alkyl substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, and —NR.sup.7R.sup.8 groups, a linear or branched C.sub.1-C.sub.10 alkoxy substituent, optionally substituted by one or more hydroxyl, C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.4 hydroxyalkyl and —NR.sup.7R.sup.8 groups; a —CO.sub.2R.sup.9 substituent, a —COR.sup.10 substituent, ALK represents a methylene substituent, R.sup.6 represents a methylene substituent, R.sup.7 and R.sup.8, which may be identical or different, denote a hydrogen atom or a linear or branched C.sub.1-C.sub.10 alkyl substituent optionally substituted with one or more hydroxyl, C.sub.1-C.sub.10 alkoxy and amino groups; R.sup.9 and R.sup.10, which may be identical or different, denote a linear or branched C.sub.1-C.sub.10 alkyl substituent optionally substituted with one or more hydroxyl, alkoxy and amino groups; and Q.sup.− represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in compounds of formula (II), wherein formula (II) cannot represent: the following compound having formula (III): ##STR00024## X.sup.− representing an anion chosen from chloride ion (Cl.sup.−), bromide ion (Br.sup.−), iodide ion (I.sup.−), perchlorate ion (ClO.sub.4.sup.−), methosulfate ion (MeSO.sub.4.sup.−), hexafluorophosphate ion (PF.sub.6.sup.−), picrate ion (C.sub.6H.sub.2N.sub.3O.sub.7.sup.−), mesylate ion (CH.sub.3SO.sub.3.sup.−) and triflate ion (CF.sub.3SO.sub.3.sup.−); the following compound having formula (IV): ##STR00025## the following compound having formula (V): ##STR00026## the compounds of formulas (VI) and (VII): ##STR00027## the compound having of (VIII): ##STR00028## the compound having formula (IX): ##STR00029##

31. Compounds of formula (II) according to claim 30 chosen from 1-(2-oxo-propyl)-pyridinium toluene-4-sulfonate and 4-acetyl-1-(2-oxo-propyl)-pyridinium chloride.

32. A composition comprising one or more compounds of formula (II) according to claim 30.

Description

EXAMPLES

Example 1

Synthesis of 4-Acetyl-1-(2-oxo-propyl)-pyridinium chloride (Compound 3)

[0231] ##STR00016##

[0232] To a solution of 0.5 g of 4-acetylpyridine (4.1 mmoles) in 2.5 g of absolute ethanol heated to 70° C. is added 0.40 g of chloroacetone (6.2 mmoles) according to the procedure described in patent WO 02/18311 A1. The entirety is heated at 75° C. for 22 hours. The reaction medium is then evaporated and washed twice with 15 mL of ethyl acetate.

[0233] The finished product is obtained as a viscous brown liquid (0.5 g, 57%).

[0234] The spectrometry and spectroscopy results agree with the structure of compound (3).

Example 2

Synthesis of 1-(2-oxo-propyl)-pyridinium toluene-4-sulfonate (Compound 2)

[0235] ##STR00017##

[0236] To a solution of 7.38 g of 1-(2-oxopropyl)pyridinium chloride (4.3 mmoles) in 40 mL of water is added 12 g silver tosylate (4.3 mmoles). A white precipitate is filtered after 1 h stirring at ambient temperature, protected from light. The filtrate is evaporated to dryness.

[0237] The finished product is obtained as a yellow-brown hardening oil (11.4 g, 86%).

[0238] The spectrometry and spectroscopy results agree with the structure of compound 2.

Example 3

[0239] In this example, the effect of improvement on the oxidizing power produced by the pyridinium salts according to the invention is studied.

[0240] I. Preparation of Synthetic Melanin

[0241] The synthetic melanin used for the evaluation is obtained by polymerizing 5,6-dihydroxyindole with hydrogen peroxide according to the following procedure:

[0242] To 456 g of water heated to 80° C. is added 100 g of 5,6 dihydroxyindole. After 10 minutes of stirring, 1 mL of a 20% aqueous ammonia solution is added then the medium is held for 30 minutes at 80° C. 152 g of 30% hydrogen peroxide is then added dropwise and the stirring is held for 2.5 hours at 80° C. After cooling, the suspension formed is filtered and washed with water.

[0243] This yields 86 g of synthetic melanin.

[0244] II. Compositions Tested

[0245] The compositions used in this example have been obtained from the following ingredients (the percentages indicated are percentages by weight relative to the total weight of the composition).

[0246] Compositions B and C are compositions according to the invention.

[0247] Comparative composition D comprises the following pyridinium salt:

##STR00018##

TABLE-US-00001 Compo- Compo- Compo- Compo- sition A sition B sition C sition D H2O2 6% 6% 6% 6% 1-2-oxo- — 36 mg 15 mg — propyl)pyridinium chloride (compound 1) 2-acetyl-1- — — — 36 mg methylpyridinium toluene-4- sulfonate Water qs 100 qs 100 qs 100 qs 100

[0248] III. Procedure

[0249] The following procedure is applied for each composition described in the table in section II.

[0250] To 1 mg synthetic melanin obtained in accordance with section I are added 1 mL of water, 1 mL of aqueous ammonia and ammonium chloride buffer at pH=9.5, and 1 mL of the composition studied (compositions A, B, C and D).

[0251] The lightening (L*) obtained after fifty minutes of incubation is measured.

[0252] IV. Results

TABLE-US-00002 Composition Composition Composition Composition A B C D Lightening level 36 68 71 62 (L*)

[0253] The lightening obtained that is observed is higher for compositions B and C according to the invention than for compositions A and D.

[0254] Particularly, the presence of pyridinium salts improving the oxidizing power of hydrogen peroxide and therefore boosting its activity is observed (comparison between composition A and compositions B and C).

[0255] Moreover, it is observed that the presence of pyridinium salts according to the invention improves the oxidizing power of hydrogen peroxide compared to a pyridinium salt having a different structure.