US5053053A
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Process for dyeing keratinous fibres with a hydroxyindole in combination with a quinone derivative; and novel 1,4-benzoquinones
Assignee: L'Oréal SA
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Filing: 1989-12-06
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Granted: 1991-10-01
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Expires: 2009-12-06
Abstract
Abstract Process for dyeing keratinous fibres, comprising the step of applying to these fibres at least one composition A containing, in a medium appropriate for dyeing, at least one mono- or di-hydroxyindole the application of the composition A being preceded or followed by the application of a composition B containing, in a medium appropriate for dyeing, at least one quinone derivative chosen from ortho- or para-benzoquinones, monoimines or diimines of ortho- or para-benzoquinones, 1,2- or 1,4-naphthoquinones, sulphonimides of ortho- or para-benzoquinones, alpha , omega -alkylene-bis-1,4-benzoquinones, or 1,2- or 1,4-naphthoquinone-monoimines or -diimines; the mono- or di-hydroxyindoles and the quinone derivatives being chosen such that the oxidation-reduction potential difference DELTA E between the oxidation-reduction potential Ei of the mono- or di-hydroxyindoles, determined at pH 7 in a phosphate medium on a vitreous carbon electrode by voltametry, and the oxidation-reduction potential Eq of the quinone derivative determined at pH 7 in a phosphate medium by polarography on a mercury electrode and relative to a saturated calomel electrode is such that DELTA E=Ei-Eq</=320 mV.
Inventors
- 👤 Arnaud DE Labbey
- 👤 Alain Baudry
- 👤 Daniel Bauer
- 👤 Pierre Bore
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 20:30
CPC Classifications
D; D06; D06P; D06P3/00; D06P3/02; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/34; A61K8/347; A61K8/35; A61K8/355; A61K8/49; A61K8/4906; A61K8/4913; A61K8/492; A61Q; A61Q5/00; A61Q5/06; A61Q5/065
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
177 words
A process for dyeing kratinous fibers comprising applying to said fibers at least one composition A comprising in a cosmetically acceptable medium at least one monohydroxyindole or dihydroxyindole, the application of said composition A to said fibers being preceded or followed by the application to said fibers of composition B comprising in a cosmetically acceptable medium at least one quinone derivative selected from the group consisting of orthobenzoquinone, parabenzoquinone, orthobenzoquinone monoimine, orthobenzoquinone diimine, parabenzoquinone monoimine, parabenzoquinone diimine, 1,2-naphthoquinone, 1,4-naphthoquinone, orthobenzoquinone sulphonamide, parabenzoquinone sulphonamide, α,ω-alkylene-bis-1,4-benzoquinone, 1,2-naphthoquinone monoimine, 1,2-naphthoquinone diimine, 1,4-naphthoquinone monoimine, and 1,4-naphthoquinone diimine; the said monohydroxyindole or dihydroxyindole and said quinone derivative being chosen such that the oxidation-reduction potential difference, ΔE, between the oxidation-reduction potential E i of said monohydroxyindole or dihydroxyindole, determined at pH 7 in a phosphate medium on a vitreous carbon electrode by voltametry, and the oxidation-reduction potential E q of said quinone derivative, determined at pH 7 in a phosphate medium by polarography on a mercury electrode and relative to a saturated calomel electrode, is such that ΔE=E i -E q ≦320 mV.
Claim 2
Dependent Claim
177 words
A process for dyeing kratinous fibers comprising applying to said fibers at least one composition A comprising in a cosmetically acceptable medium at least one monohydroxyindole or dihydroxyindole, the application of said composition A to said fibers being preceded or followed by the application to said fibers of composition B comprising in a cosmetically acceptable medium at least one quinone derivative selected from the group consisting of orthobenzoquinone, parabenzoquinone, orthobenzoquinone monoimine, orthobenzoquinone diimine, parabenzoquinone monoimine, parabenzoquinone diimine, 1,2-naphthoquinone, 1,4-naphthoquinone, orthobenzoquinone sulphonamide, parabenzoquinone sulphonamide, α,ω-alkylene-bis-1,4-benzoquinone, 1,2-naphthoquinone monoimine, 1,2-naphthoquinone diimine, 1,4-naphthoquinone monoimine, and 1,4-naphthoquinone diimine; the said monohydroxyindole or dihydroxyindole and said quinone derivative being chosen such that the oxidation-reduction potential difference, ΔE, between the oxidation-reduction potential E i of said monohydroxyindole or dihydroxyindole, determined at pH 7 in a phosphate medium on a vitreous carbon electrode by voltametry, and the oxidation-reduction potential E q of said quinone derivative, determined at pH 7 in a phosphate medium by polarography on a mercury electrode and relative to a saturated calomel electrode, is such that ΔE=E i -E q ≦320 mV.
Claim 3
Dependent Claim
334 words
The process of claim 1 wherein said monohydroxyindole or dihydroxyindole has the formula ##STR16## wherein R 1 represents hydrogen or C 1 -C 4 alkyl, R 2 and R 3 , each independently, represent hydrogen, C 1 -C 4 alkyl, carboxyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 hydroxyalkyl or C 1 -C 4 aminoalkyl, and R 4 , R 5 , R 6 and R 7 , each independently represent hydrogen; C 1 -C 4 alkyl; amino; amino substituted by one or two C 1 -C 4 alkyl groups; amino substituted by one or two C 1 -C 4 hydroxyalkyl groups; C 2 -C 6 acylamino; carboxyl; C 1 -C 4 carboxyalkyl; C 1 -C 4 alkoxycarbonyl; ##STR17## wherein r and R', each independently, represent hydrogen or C 1 -C 4 alkyl; halogen; C 1 -C 4 hydroxyalkyl; C 1 -C 4 aminoalkyl; OH; and OZ wherein Z represents linear or branched C 1 -C 20 alkyl, aralkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenyl, --SiR 11 R 12 R 13 , --P(O)(OR 8 ) 2 or R 8 OSO 2 --, or the pairs R 4 and R 5 , or R 5 and R 6 , or R 6 and R 7 , form, together with the carbon atoms to which each pair is attached, a ring containing a carbonyl group, a thiocarbonyl group, a ##STR18## group or a ##STR19## group, with the proviso that at least one of R 4 , R 5 , R 6 and R 7 represents an OH group, R 8 and R 9 represent hydrogen or C 1 -C 4 alkyl, R 10 represents C 1 -C 4 alkoxy, C 1 -C 4 monalkylamino or C 1 -C 4 dialkylamino, and R 11 , R 12 and R 13 , each independently, represent linear or branched alkyl, and the alkali metal, alkaline earth metal, ammonium and amine salts of said monohydroxyindole or dihydroxyindole.
Claim 4
Dependent Claim
41 words
The process of claim 1 wherein said monohydroxyindole or dihydroxyindole is selected from the group consisting of 4-hydroxyindole 4-hydroxy-5-methoxyindole 4-hydroxy-5-ethoxyindole 5-hydroxyindole 2-carboxy-5-hydroxyindole 5-hydroxy-6-methoxyindole 6-hydroxyindole 6-hydroxy-7-methoxyindole 5-methoxy-6-hydroxyindole 2-carboxy-6-hydroxyindole 2-ethoxycarbonyl-6-hydroxyindole 7-hydroxyindole 2,3-dimethyl-7-hydroxy-4-methoxyindole 5,6-dihydroxyindole 1-methyl-5,6-dihydroxyindole 2-methyl-5,6-dihydroxyindole 3-methyl-5,6-dihydroxyindole 2,3-dimethyl-5,6-dihydroxyindole 5-acetoxy-6-hydroxyindole 6acetoxy-5-hydroxyindole, 2-ethoxycarbonyl-5,6-dihydroxyindole 2-carboxy-5,6-dihydroxyindole 2,3-dimethyl-5-hydroxy-6-aminoindole 2,3-dimethyl-5-amino-6-hydroxyindole.
Claim 5
Dependent Claim
304 words
The process of claim 1 wherein said quinone derivative has formula II or formula III ##STR20## wherein X represents oxygen or NR 19 , Y represents oxygen or NR 20 , R 19 and R 20 , each independently, represent hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkylsulphonyl or phenylsulphonyl, p1 R 14 , R 15 , R 16 , R 17 and R 18 , each independently, represent hydrogen; C 1 -C 4 alkyl; carboxyl; C 1 -C 4 alkylcarbonyl; C 1 -C 4 alkoxycarbonyl; C 1 -C 4 alkoxymethyl; C 1 -C 4 alkylthiomethyl; C 1 -C 4 hydroxyalkylthiomethyl; C 1 -C 4 hydroxyalkylsulphinyl; ##STR21## wherein r and R', each independently, represent hydrogen, or C 1 -C 4 alkyl; carboxyalkyl; halogen; C 1 -C 4 hydroxyalkyl; amino; amino substituted by one or two C 1 - 4 alkyl groups; amino substituted by one or two C 1 -C 4 hydroxyalkyl groups; C 2 -C 6 acylamin; SO 3 M wherein M represents hydrogen, K or Na; sulphoxide, sulphone; sulphonamide; OZ 1 wherein Z 1 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 carboxyalkyl; carboxyphenyl; C 4 carboxyphenyl substituted by C 1 -C 4 alkoxy; or --SZ 2 wherein Z 2 represents C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 dihydroxyalkyl or C 1 -C 4 carboxyalkyl, or R 14 and R 15 form together with the carbon atoms to which they are attached a cyclic group having the formula ##STR22## wherein R' 1 , R' 2 , R' 3 and R' 4 have the meanings given above for R 14 , R 15 , R 16 , R 17 and R 18 when they do not form a ring.
Claim 6
Dependent Claim
164 words
The process of claim 1 wherein said quinone derivative is a benzoquinone having formula (II) or (II') ##STR23## wherein R=hd 14, R 15 , R 16 , R 17 and R 18 , each independently, represent hydrogen; C 1 -C 4 lower alkyl; C 1 -C 4 lower alkoxy; halogen; C 2 -C 6 acylamino; SO 3 M wherein M represents hydrogen, K or Na; C 1 -C 4 alkoxy methyl; carboxy C 1 -C 4 alkyl; C 1 -C 4 alkoxycarbonyl; dialkylamino; OZ 1 wherein Z 1 represents carboxy C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl; or SZ 2 wherein Z 2 represents C 1 -C 4 hydroxyalkyl, C 1 -C 4 dihydroxyalkyl, carboxy C 1 -C 4 alkyl or C 1 -C 4 alkyl; X represents oxygen or NR 19 , Y represents oxygen or NR 20 , R 19 and R 20 , each independently, represent hydrogen, halogen, C 1 -C 4 lower alkyl, methylsulphonyl or phenylsulphony.
Claim 7
Dependent Claim
244 words
The process of claim 1 wherein said quinone derivative has formula (V) or formula (VI) ##STR24## wherein R' 1 , R' 2 , R' 3 , R' 4 , R' 16 , R 17 and R 18 , each independently, represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy; carboxyl; C 1 -C 4 alkylcarbonyl; C 1 -C 4 alkoxycarbonyl; C 1 -C 4 alkoxymethyl; C 1 -C 4 alkylthiomethyl; C 1 -C 4 hydroxyalkylthiomethyl; C 1 -C 4 hydroxyalkylsulphinyl; ##STR25## wherein r and r', each independently, represent hydrogen or C 1 -C 4 alkyl; carboxyalkyl; halogen; C 1 -C 4 hydroxyalkyl; amino; amino substituted by one or two C 1 -C 4 alkyl groups; amino substituted by one or two C 1 -C 4 hydroxyalkyl groups; C 2 -C 6 acylamino; SO 3 M wherein M represents hydrogen, K or NA; dialkylamino; sulphoxide, sulphone; sulphonamide; OZ 1 wherein Z 1 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 carboxyalkyl; carboxyphenyl; C 4 carboxyphenyl substituted by C 1 -C 4 alkoxy; or --SZ 2 wherein Z 2 represents C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 dihydroxyalkyl or C 1 -C 4 carboxyalkyl, X represents oxygen or NR 19 , Y represents oxygen or NR 20 and R 19 and R 20 , each independently, represent hydrogen, halogen, C 1 -C 4 lower alkyl, methylsulphonyl or phenylsulphonyl.
Claim 8
Dependent Claim
54 words
The process of claim 1 wherein said quinone derivative is selected from the group consisting of 1,4-benzoquinone, 2-methoxy-1,4-benzoquinone, 2-methyl-1,4-benzoquinone, 2,6-dimethyl-1,4-benzoquinone, 2,3,5-trichloro-6-methyl-1,4-benzoquinone, 2-acetylamino-1,4-benzoquinone, 2-acetylamino-3,5-dimethyl-1,4-benzoquinone, 2,6-dimethyl-5acetylamino-1,4-benzoquinone, 2-chloro-1,4-benzoquinone, tetrachloro-1,2-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-β-carboxyethoxy-1,4-benzoquinone, 2-methoxymethyl-1,4-benzoquinone, 2-(βhydroxyethyl)-1,4-benzoquinone, 2-(βhydroxyethylthio)-1,4-benzoquinone, 2,5-bis(β-hydroxyethylthio)-1,4-benzoquinone, 2-(β,γ-dihydroxypropylthio)-1,4-benzoquinone, 2-(β-carboxyethylthio)-1,4-benzoquinone, 2-carboxymethyl-1,4-benzoquinone, 2-(β-hydroxyethylthio)-6-methyl-1,4-benzoquinone, 2-methoxycarbonyl-3-methoxy-1,4-benzoquinone, 2-methoxycarbonyl-1,4-benzoquinone, 2-methylthio-1,4-benzoquinone, 2-dimethylamino-1,4-benzoquinone, 2-acetylamino-5-methoxy-1,4-benzoquinone, 2-(β-hydroxyethylthio) methyl-1,4-benzoquinone, 2-(methylthio) methyl-1,4-benzoquinone, 4,5-dimethoxy-1,2-benzoquinone, 4-methyl-5-chloro-1,2-benzoquinone, 4,5-dimethyl-1,2-benzoquinone, 2,3-dimethyl-1,4benzoquinone, 2-β-hydroxyethoxy-1,4-benzoquinone, N-methylsulphonyl-1,4-benzoquinone monoimine, N-phenylsulphonyl-1,4-benzoquinone monoimine,
Claim 9
Dependent Claim
8 words
4-naphthoquinone, 1,2-naphthoquinone, 1,2-naphthoquinone-4-sulphonic acid 2,3-dichloro-1,4-naphthoquinone and N-2,6-trichloro-1,4-benzoquinone imine.
Claim 10
Dependent Claim
8 words
4-naphthoquinone, 1,2-naphthoquinone, 1,2-naphthoquinone-4-sulphonic acid 2,3-dichloro-1,4-naphthoquinone and N-2,6-trichloro-1,4-benzoquinone imine.
Claim 11
Dependent Claim
46 words
The process of claim 1 wherein said composition A contains, 5,6-dihydroxyindole and said composition B contains a quinone derivative selected from the group consisting of 1,4-benzoquinone, 2-methyl-1,4-benzoquinone, 2,6-dimethyl-1,4-benzoquinone, 2-methoxy-1,4-benzoquinone, 2-chloro-1,4-benzoquinone, 2,3,5-trichloro-6-methyl-1,4-benzoquinone, 2-acetylamino-1,4-benzoquinone, 2-acetylamino-3-methoxy-1,4benzoquinone, 2,6-dimethyl-5-acetylamino-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-methoxymethyl-1,4-benzoquinone, 2-(β-hydroxyethyl)-1,4-benzoquinone, 2-(β,γ-dihydroxypropylthio)-1,4-benzoquinone, 2-(β-carboxyethylthio)-1,4-benzoquinone, 2-carboxymethyl-1,4-benzoquinone, 1,4-naphthoquinone, N-2,6-trichloro-1,4-benzoquinoneimine, 1,2-naphthoquinone and 1,2-naphthoquinone-4-sulphonic acid.
Claim 12
Dependent Claim
26 words
The process of claim 1 wherein said monohydroxyindole or dihydroxyindole is present in said composition A in an amount ranging from about 0.01 to 0.3 mole/liter.
Claim 13
Dependent Claim
24 words
The process of claim 1 wherein said quinone derivative is present in said composition B in an amount ranging from 0.005 to 1 mole/liter.
Claim 14
Dependent Claim
21 words
The process of claim 1 wherein the pH of said compositions A and B, each independently, ranges from 2 to 10.
Claim 15
Dependent Claim
13 words
The process of claim 1 wherein said composition B has an acidic pH.
Claim 16
Dependent Claim
28 words
The process of claim 1 wherein said cosmetically acceptable medium for said compositions A and B comprises water or a mixture of water and a cosmetically acceptable solvent.
Claim 17
Dependent Claim
27 words
The process of claim 1 wherein said cosmetically acceptable medium for said compositions A and B comprises a cosmetically acceptable anhydrous solvent containing less than 1% water.
Claim 18
Dependent Claim
56 words
The process of claim 1 wherein said compositions A and B, each independently, also contain an anionic, cationic, nonionic or amphoteric surfactant or a mixture thereof; a thickener; a fragrance; a sequestering agent; a film-forming agent; a treatment agent; a dispersing agent; a conditioner; a preservative; an opacifying agent; or a swelling agent for keratinous fibers.
Claim 19
Dependent Claim
50 words
The process of claim 1 wherein said composition A or said composition B or both said compositions also contains another dye selected from a direct dye, an oxidation dye, a coupler or a rapid oxidation dyestuff precursor having a benzenic structure and generating a colored compound when oxidized in air.
Claim 20
Dependent Claim
67 words
The process of claim 1 wherein said composition A or said composition B or both said compositions also contains another quinone dye selected from the group consisting of a benzoquinone dye, a benzoquinoneimine dye, a benzoquinonediiimine dye, a naphthoquinone dye, a naphthoquinoneimine dye, a naphthoquinonediimine dye and a quinone indole dye, said another quinone dye having an oxidation-reduction potential such that ΔE is greater than 320 mV.
Claim 21
Dependent Claim
33 words
A multicompartment kit for use in dyeing keratinous fibers comprising a first compartment housing said composition A defined in claim 1 and a second compartment housing said composition B defined in claim 1.
Claim 22
Dependent Claim
92 words
A multicompartment kit for use in dyeing keratinous fibers comprising a first compartment housing said composition A defined in claim 1, a second compartment housing said composition B defined in claim 1, wherein the said cosmetically acceptable medium of at least one of said compositions A and B comprises a cosmetically acceptable anhydrous solvent, and a third compartment housing a cosmetically acceptable aqueous medium to be admixed just before use with contents of said compartment containing one or the other of said compositions A and B in said cosmetically acceptable anhydrous solvent.
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