# US 10,765,615 B2 · Use of particular pyridinium salts for the treatment of keratin substances, compositions and implementation methods

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- Number: US 10,765,615 B2
- Document ID: US10765615B2
- Status: Granted
- Kind: B2
- Application number: 15/536,731
- Filed: 2015-12-21
- Published: 2017-11-30
- Granted: 2020-09-08
- Earliest claimed: 2014-12-19
- Assignees: L'oreal
- Applicants: L'oreal
- Inventors: Leila Hercouet; Stephane Sabelle
- Web page: https://patentgrep.com/patent/US10765615B2

## CPC

- A61K 8/4926: {having six membered rings}
- A61K 8/22: Peroxides; Oxygen; Ozone
- A61K 8/466: {containing sulfonic acid derivatives; Salts}
- A61Q 5/08: Preparations for bleaching the hair
- C07C 309/30: of six-membered aromatic rings substituted by alkyl groups
- C07D 213/20: Quaternary compounds thereof
- C07D 213/50: Ketonic radicals
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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

### Claim 1

A method for treating keratin substances, the method comprising applying to the keratin substances at least one compound chosen from compounds represented by formula (I), addition salts thereof, or solvates thereof:
wherein:
R1, R2, R3, R4 and R5, which may be identical or different, each represent:
a hydrogen or halogen atom;
a linear or branched C1-C10 alkyl substituent, optionally substituted by one or more hydroxyl, C1-C10 alkoxy, C1-C4 hydroxyalkyl and —NR7R8 groups;
a linear or branched C1-C10 alkoxy substituent, optionally substituted by one or more hydroxyl, C1-C10 alkoxy, C1-C4 hydroxyalkyl and —NR7R8 groups;
or two adjacent substituents R1 and R2, R2 and R3, R3 and R4 and/or R4 and R5 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 C1-C10 alkyl substituents, one or more linear or branched C1-C10 alkoxy substituents, one or more hydroxyl groups, one or more C1-C4 hydroxyalkyl substituents and one or more —NR7R8 groups;
ALK represents a linear or branched, saturated or unsaturated C1-C10 alkyl substituent;
R6 represents:
a hydrogen or halogen atom,
a linear or branched, saturated or unsaturated C1-C10 alkyl substituent, optionally interrupted by one or more heteroatoms chosen from oxygen and nitrogen and/or optionally substituted by one or more hydroxyl, C1-C10 alkoxy, C1-C4 hydroxyalkyl and —NR7R8 groups;
an aryl substituent including 5 to 12 members optionally substituted by one or more halogen atoms, one or more linear or branched C1-C10 alkyl substituents, one or more linear or branched C1-C10 alkoxy substituents, one or more hydroxyl groups, one or more C1-C4 hydroxyalkyl substituents and one or more —NR7R8 groups;
X represents a heteroatom chosen from an oxygen atom or a sulfur atom, or a —NR11 substituent;
R7, R8, and R11, which may be identical or different, denote a hydrogen atom or a linear or branched C1-C10 alkyl substituent optionally substituted with one or more hydroxyl or C1-C10 alkoxy, C1-C4 hydroxyalkyl and amino groups;
wherein one of the substituents R1 or R5 may form a ring with the substituent R6;
Q− represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in compounds of formula (I).

### Claim 2 (depends on 1)

The method according to claim 1, characterized in that X represents an oxygen atom.

### Claim 3 (depends on 1)

The method according to claim 1, characterized in that ALK represents a linear C1-C10 alkylene substituent, a linear C2-C10 alkenylene substituent or a linear C2-C10 alkynylene substituent.

### Claim 4 (depends on 1)

The method according to claim 1, characterized in that the substituents R1 and R5 represent a hydrogen atom.

### Claim 5 (depends on 1)

The method according to claim 1, characterized in that the substituents R2 and R4, which may be identical or different, represent a hydrogen atom or a linear C1-C4 alkyl substituent.

### Claim 6 (depends on 1)

The method according to claim 1, characterized in that R3 represents a hydrogen atom or a —COR10 substituent with R10 denoting a linear C1-C10 alkyl substituent.

### Claim 7 (depends on 6)

The method according to claim 6, characterized in that R7, R8, and R10, which may be identical or different, denote a linear or branched C1-C10 alkyl substituent optionally substituted with one or more hydroxyl, C1-C10 alkoxy and amino groups.

### Claim 8 (depends on 1)

The method according to claim 1, characterized in that the at least one compound of formula (I) is chosen from the compounds of formula (H), addition salts thereof, or solvates thereof:
in which:
R1 and R5 represent a hydrogen atom;
R2 and R4, which may be identical or different, represent:
a hydrogen atom,
a linear or branched C1-C10 alkyl substituent, optionally substituted by one or more hydroxyl, C1-C10 alkoxy, and —NR7R8 groups,
a linear or branched C1-C10 alkoxy substituent, optionally substituted by one or more hydroxyl, C1-C10 alkoxy and —NR7R8 groups;
R3 represents:
a hydrogen atom;
a linear or branched C2-C10 alkyl substituent, optionally substituted by one or more hydroxyl, C1-C10 alkoxy and —NR7R8 groups,
a linear or branched C1-C10 alkoxy substituent, optionally substituted by one or more hydroxyl, C1-C10 alkoxy, C1-C4 hydroxyalkyl and —NR7R8 groups:
ALK represents a methylene substituent,
R6 represents a methylene substituent,
R7 and R8, which may be identical or different, denote a hydrogen atom or a linear or branched C1-C10 alkyl substituent optionally substituted with one or more hydroxyl, C1-C10 alkoxy and amino groups;
Q+ represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in compounds of formula (II).

### Claim 9 (depends on 1)

The method according to claim 1, characterized in that the compound(s) of formula (I) are chosen from the following compounds:
and mixtures thereof,
wherein a represents an anion or a mixture of organic or inorganic anions that ensure electroneutrality in said compounds.

### Claim 10 (depends on 1)

The method according to claim 1, wherein the method is for improving the oxidizing activity of one or more chemical oxidizing agents.

### Claim 11 (depends on 1)

The treatment method according to claim 1, wherein the one or more compounds of formula (I) are applied in the presence of one or more chemical oxidizing agents.