IP Library › Granted Patent US 12,409,124
Granted Patent B2
US 12,409,124 · App. 18/268,065 · Granted Sep 9, 2025

Composition comprising a particular oxidation dye precursor and a particular carboxylic acid

Inventors: Laurence Cottard-Mei (Saint-Ouen, FR); Robin Protat (Saint-Ouen, FR)
Assignee: L'OREAL
A61K8/49A61K8/22A61K8/415A61K8/44A61K8/4973A61Q5/10A61K2800/882
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Quick Facts
Patent No.
US 12,409,124
App. No.
18/268,065
Granted
Sep 9, 2025
Kind
B2
Abstract

The invention relates to a composition comprising at least one oxidation dye coupler chosen from 6-hydroxy benzomorpholine of formula (I), hydroxyethyl-3.4-methy lenedioxyaniline of formula (II). 2-amino-5-ethylphenol of formula (III), one of their addition salts, their solvates and/or the solvates of their salts, and at least one compound chosen from N,N-dicarboxymethyl glutamic acid, one of its salts and mixtures thereof. The invention also relates to a process for dyeing keratin fibres, preferably the hair, comprising the application of the composition to said keratin fibres.

Claims (42)

1. A composition comprising:

a) at least one oxidation coupler chosen from:

i) 6-hydroxybenzomorpholines of formula (I), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

ii) hydroxyethyl-3,4-methylenedioxyanilines of formula (II), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

iii) 2-amino-5-ethylphenols of formula (III), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

iv) mixtures of two or more thereof; and

b) at least one compound chosen from N,N-dicarboxymethyl glutamic acid, salts thereof, or mixtures of two or more thereof.

2. The composition of claim 1 , wherein the total amount of oxidation coupler(s) ranges from 0.001% to 20% by weight, relative to the total weight of the composition.

3. The composition of claim 1 , wherein the total amount of oxidation coupler(s) ranges from 0.05% to 10% by weight, relative to the total weight of the composition.

4. The composition of claim 1 , further comprising at least one oxidation base.

5. The composition of claim 4 , wherein the at least one oxidation base is chosen from para-phenylenediamines, bis (phenyl) alkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, addition salts thereof, or mixtures of two or more thereof.

6. The composition of claim 4 , wherein the total amount of oxidation base(s) ranges from 0.001% to 20% by weight, relative to the weight of the composition.

7. The composition of claim 4 , wherein the weight ratio of the total amount of oxidation base(s) to the total amount of oxidation coupler(s) ranges from 0.1:1 to 10:1.

8. The composition of claim 1 , wherein the at least one compound is chosen from alkali metal salts of N,N-dicarboxymethyl glutamic acid.

9. The composition of claim 1 , in which the total amount of compound(s) chosen from N,N-dicarboxymethyl glutamic acid, salts thereof, or mixtures thereof ranges from 0.001% to 15% by weight, relative to the total weight of the composition.

10. The composition of claim 1 , further comprising at least one fatty substance.

11. The composition of claim 10 , wherein the at least one fatty substance is chosen from liquid fatty substances, solid fatty substances, and mixtures thereof.

12. The composition of claim 11 , wherein the at least one liquid fatty substance is chosen from liquid hydrocarbons comprising more than 16 carbon atoms, plant oils, liquid fatty alcohols, liquid fatty esters, silicone oils, or mixtures of two or more thereof.

13. The composition of claim 11 , wherein the at least one solid fatty substance is chosen from solid fatty acids, solid fatty alcohols, solid esters of fatty acids, solid esters of fatty alcohols, waxes, ceramides, or mixtures of two or more thereof.

14. The composition of claim 1 , further comprising at least one surfactant.

15. The composition of claim 14 , wherein the at least one surfactant is chosen from anionic surfactants, non-ionic surfactants, or mixtures of two or more thereof.

16. The composition of claim 1 , further comprising at least one alkaline agent.

17. The composition of claim 16 , wherein the at least one alkaline agent is chosen from alkanolamines.

18. The composition of claim 1 , further comprising at least one chemical oxidizing agent.

19. A method for dyeing keratin fibers comprising mixing a dyeing composition (A) with an oxidizing composition (B),

wherein the dyeing composition (A) comprises:

a) at least one oxidation coupler chosen from:

i) 6-hydroxybenzomorpholines of formula (I), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

ii) hydroxyethyl-3,4-methylenedioxyanilines of formula (II), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

iii) 2-amino-5-ethylphenols of formula (III), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

iv) mixtures of two or more thereof; and

b) at least one compound chosen from N,N-dicarboxymethyl glutamic acid, salts thereof, or mixtures of two or more thereof; and

wherein the oxidizing composition (B) comprises at least one chemical oxidizing agent; and applying the mixture to the keratin fibers.

20. A kit comprising:

a first compartment comprising a dyeing composition comprising:

a) at least one oxidation coupler chosen from:

i) 6-hydroxybenzomorpholines of formula (I), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

ii) hydroxyethyl-3,4-methylenedioxyanilines of formula (II), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

iii) 2-amino-5-ethylphenols of formula (III), addition salts thereof, solvates thereof, solvates of its salts thereof, or mixtures of two or more thereof:

iv) mixtures of two or more thereof, and

b) at least one compound chosen from N,N-dicarboxymethyl glutamic acid, salts thereof, or mixtures of two or more thereof; and

a second compartment comprising an oxidizing composition comprising at least one chemical oxidizing agent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2024
From: COTTARD-MEI, LAURENCE; PROTAT, ROBIN
To: L'OREAL
Reel/Frame 069091/0786 →
Priority Claims (1)
FR 2013469 · Dec 17, 2020 · national
Continuity (1)
Related Publication 20240307286A1 · Sep 19, 2024
References Cited (45)
US 3589578A · Kamal et al. · 1971 [cited by applicant]
US 4003699A · Rose et al. · 1977 [cited by applicant]
US 4013307A · Dowd et al. · 1977 [cited by applicant]
US 4137180A · Naik et al. · 1979 [cited by applicant]
US RE30199E · Rose et al. · 1980 [cited by applicant]
US 4823985A · Grollier et al. · 1989 [cited by applicant]
US 4874554A · Lange et al. · 1989 [cited by applicant]
US 5061289A · Clausen et al. · 1991 [cited by applicant]
US 5380340A · Neunhoeffer et al. · 1995 [cited by applicant]
US 5534267A · Neunhoeffer et al. · 1996 [cited by applicant]
US 5663366A · Neunhoeffer et al. · 1997 [cited by applicant]
US 5766576A · Löwe et al. · 1998 [cited by applicant]
US 6099592A · Vidal et al. · 2000 [cited by applicant]
US 6284003B1 · Rose et al. · 2001 [cited by applicant]
US 6730789B1 · Birault et al. · 2004 [cited by applicant]
US 11213471B2 · Nicou et al. · 2022 [cited by applicant]
US 20130081647A1 · Vohra et al. · 2013 [cited by applicant]
US 20190224088A1 · Gross · 2019 [cited by examiner]
US 20200163851A1 · Nicou · 2020 [cited by examiner]
DE 2359399A1 · 1975 [cited by applicant]
DE 3843892A1 · 1990 [cited by applicant]
DE 4133957A1 · 1993 [cited by applicant]
DE 19543988A1 · 1997 [cited by applicant]
EP 0770375A1 · 1997 [cited by applicant]
EP 3295923A1 · 2018 [cited by examiner]
FR 2586913A1 · 1987 [cited by applicant]
FR 2733749A1 · 1996 [cited by applicant]
FR 2801308A1 · 2001 [cited by applicant]
FR 2886136A1 · 2006 [cited by applicant]
FR 3045379A1 · 2017 [cited by applicant]
GB 1026978A · 1966 [cited by applicant]
GB 1153196A · 1969 [cited by applicant]
IT 201900005622A1 · 2020 [cited by applicant]
JP 02019576A · 1990 [cited by applicant]
JP 05163124A · 1993 [cited by applicant]
JP 2017160198A · 2017 [cited by examiner]
WO 9408969A1 · 1994 [cited by applicant]
WO 9408970A1 · 1994 [cited by applicant]
WO 9615765A1 · 1996 [cited by applicant]
WO 2022129377A1 · 2022 [cited by applicant]
International Search Report and Written Opinion for counterpart Application No. PCT/EP2021/086263, dated Apr. 21, 2022. [cited by applicant]
International Search Report and Written Opinion for counterpart Application No. PCT/EP2021/086267, dated May 3, 2022. [cited by applicant]
Grevalcuore et al., “Hair Care Composition,” Research Disclosure, Kenneth Mason Publications, Hampshire, UK, GB, vol. 672, No. 75, Apr. 1, 2020, (4 pages). [cited by applicant]
Porter, M.R., “Handbook of Surfactants,” published by Blackie & Son (Glasgow and London), 1991, pp. 116-178. [cited by applicant]
Todd, Charles, et al., “Volatile Silicone Fluids for Cosmetic Formulations,” Cosmetics and Toiletries, vol. 91, Jan. 1976, pp. 29-32. [cited by applicant]