Claims
- 1. A tinctorial composition for dyeing keratinous fibers comprising in a medium suitable for dyeing said fibers at least one oxidation dyestuff precursor selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a bis-phenylalkylenediamine, an ortho aminophenol and an orthophenylenediamine, in combination with at least one heterocyclic coupler having the formula ##STR7## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl,
- R.sub.2 represents hydrogen, C.sub.1 -C.sub.4 lower alkyl, carboxyl or alkoxycarbonyl,
- R.sub.3 represents hydrogen, halogen, C.sub.1 -C.sub.4 lower alkyl, carboxyl, alkoxycarbonyl or formyl,
- X represents hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, acetylamino or di(C.sub.1 -C.sub.4) alkylaminomethyl, with the proviso that at least one of X, R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen, and the salts thereof,
- said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 percent by weight based on the total weight of said composition, and the combined weight of said oxidation dyestuff precursor and said heterocyclic coupler ranging from 0.3 to 7 percent based on the total weight of said composition,
- said composition being free of any benzoquinone or naphthoquinone capable of oxidizing said heterocyclic coupler of formula I and being free of any iodide or nitrite in an amount capable of oxidizing said oxidation dyestuff precursor and the said heterocyclic coupler of formula I.
- 2. The tinctorial composition of claim 1 wherein said heterocyclic coupler of formula I is selected from the group consisting of
- 4-hydroxy-5-methylindole,
- 4-hydroxy-3-chloroindole,
- 4-hydroxy-5-dimethylaminomethylindole,
- 4-hydroxy-3-formyl-2-methyl-1-ethylindole,
- 4-hydroxy-3-formylindole,
- 4-hydroxy-3-formyl-2,6-dimethylindole,
- 4-hydroxy-3-formyl-1-methylindole,
- 4-hydroxy-1,5-dimethylindole,
- 4-hydroxy-5-methyl-2-carboxyindole,
- 4-hydroxy-6-methyl-3-ethoxycarbonylindole,
- 4-hydroxy-7-methylindole,
- 4-hydroxy-2,5-dimethyl-1-ethylindole,
- 4-hydroxy-2,6-dimethyl-1-ethylindole,
- 4-hydroxy-2-methyl-1-ethylindole,
- 4-hydroxy-3-ethylindole,
- 4-hydroxy-2,6-dimethylindole,
- 4-hydroxy-6-methylindole and
- 4-hydroxy-2-carboxy-5-methylindole.
- 3. The tinctorial composition of claim 1 wherein said paraphenylenediamine has the formula ##STR8## wherein R.sub.4, R.sub.5 and R.sub.6, each independently, represent hydrogen, halogen, alkyl having 1-4 carbon atoms or alkoxy having 1-4 carbon atoms,
- R.sub.7 and R.sub.8, each independently, represent hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, carbamyl alkyl, mesyl aminoalkyl, acetylamino alkyl, ureidoalkyl, carbalkoxyaminoalkyl, piperidinoalkyl or morpholinoalkyl, wherein the alkyl and alkoxy moieties have from 1-4 carbon atoms, or R.sub.7 and R.sub.8, together with the nitrogen atom to which they are attached, form a piperidino or morpholino heterocycle, with the proviso that R.sub.4 or R.sub.6 represents hydrogen when R.sub.7 and R.sub.8 do not represent hydrogen,
- and the salts of said paraphenylenediamine.
- 4. The tinctorial composition of claim 3 wherein said paraphenylenediamine of formula II is selected from the group consisting of
- paraphenylenediamine,
- paratoluylenediamine,
- methoxyparaphenylenediamine,
- chloroparaphenylenediamine,
- 2,6-dimethylparaphenylenediamine,
- 2,5-dimethylparaphenylenediamine,
- 2-methyl-5-methoxyparaphenylenediamine,
- 2,6-dimethyl-5-methoxyparaphenylenediamine,
- N,N-dimethylparaphenylenediamine,
- 3-methyl-4-amino,N,N-diethylaniline,
- N,N-di(.beta.-hydroxyethyl) paraphenylenediamine,
- 3-methyl-4-amino-N,N-di-(.beta.-hydroxyethyl) aniline,
- 3-chloro-4-amino-N,N-di-(.beta.-hydroxyethyl) aniline,
- 4-amino-N,N-(ethyl, carbamylmethyl) aniline,
- 3-methyl-4-amino-N,N-(ethyl, carbamylmethyl) aniline,
- 4-amino-N,N-(ethyl, .beta.-piperidinoethyl) aniline,
- 3-methyl-4-amino-N,N-(ethyl, .beta.-piperidinoethyl) aniline,
- 4-amino-N,N-(ethyl, .beta.-morpholinoethyl) aniline,
- 3-methyl-4-amino-N,N-(ethyl, .beta.-morpholinoethyl) aniline,
- 4-amino-N,N-(ethyl, .beta.-acetylaminoethyl) aniline,
- 4-amino-N-(.beta.-methoxyethyl) aniline,
- 3-methyl-4-amino-N,N-(ethyl, .beta.-acetylaminoethyl) aniline,
- 4-amino-N,N-(ethyl, .beta.-mesylaminoethyl) aniline,
- 3-methyl-4-amino-N,N-(ethyl, .beta.-mesylaminoethyl) aniline,
- 4-amino-N,N-(ethyl, .beta.-sulphoethyl) aniline,
- 3-methyl-4-amino-N,N-(ethyl, .beta.-sulphoethyl) aniline,
- N-[(4'-amino) phenyl] morpholine,
- N-[(4'-amino) phenyl] piperidine and the salts thereof.
- 5. The tinctorial composition of claim 1 where said para aminophenol is selected from the group consisting of para aminophenol,
- 2-methyl-4-aminophenol,
- 3-methyl-4-aminophenol,
- 2-chloro-4-aminophenol,
- 3-chloro-4-aminophenol,
- 2,6-dimethyl-4-aminophenol,
- 3,5-dimethyl-4-aminophenol,
- 2. 3-dimethyl-4-aminophenol,
- 2-hydroxymethyl-4-aminophenol,
- 2-(.beta.-hydroxyethyl)-4-aminophenol,
- 2-methoxy-4-aminophenol,
- 3-methoxy-4-aminophenol,
- 2,5-dimethyl-4-aminophenol and
- 2-methoxymethyl-4-aminophenol.
- 6. The tinctorial composition of claim 1 wherein said bis-phenylalkylenediamine has the formula ##STR9## wherein Z.sub.1 and Z.sub.2, each independently, represent hydroxyl or NHR.sub.3 wherein R.sub.3 represents hydrogen or lower alkyl,
- R.sub.1 and R.sub.2, each independently, represent hydrogen, halogen or alkyl,
- R represents hydrogen, alkyl, hydroxyalkyl, or aminoalkyl wherein the amino moiety is substituted or unsubstituted, and
- Y represents a member selected from the group consisting of --(CH.sub.2).sub.n --, --(CH.sub.2).sub.n,--O--(CH.sub.2).sub.n,--, --(CH.sub.2).sub.n, --CHOH--(CH.sub.2).sub.n,-- and ##STR10## where n is an integer ranging from 0 to 8 and n' is an integer ranging from 0 to 4, and the acid addition salt of said bis-phenylalkylenediamine.
- 7. The tinctorial composition of claim 6 wherein said bis-phenylalkylenediamine of formula IIa is selected from the group consisting of
- N,N'-bis (.beta.-hydroxyethyl)-N,N'-bis (4'-aminophenyl)-1,3-diaminopropan-2-ol,
- N,N'-bis (.beta.-hydroxyethyl)-N,N'-bis(4'-aminophenyl) ethylenediamine,
- N,N'-bis (4-aminophenyl)-tetramethylenediamine,
- N,N'-bis (.beta.-hydroxyethyl)-N,N'-bis (4-aminophenyl) tetramethylenediamine,
- N,N'-bis (4-methylaminophenyl) tetramethylenediamine and
- N,N'-bis (ethyl)-N,N'-bis (4'-amino-3'-methylphenyl) ethylenediamine.
- 8. The tinctorial composition of claim 1 which also contains, in addition to the heterocyclic coupler of formula (I), a metadiphenol, a meta-aminophenol, a metaphenylenediamine, a meta-acylaminophenol, a meta-ureidophenol, a metacarbalkoxyamino-phenol .alpha.-naphthol, 4-hydroxyindole, a .beta.-ketocompound or a pyrazolone.
- 9. The tinctorial composition of claim 1 which also contains a direct dye.
- 10. The tinctorial composition of claim 1 wherein said medium suitable for dyeing said fibers is an aqueous medium having a pH ranging from 8 to 11.
- 11. The tinctorial composition of claim 1 which also contains an anionic, cationic, nonionic or amphoteric surfactant or a mixture thereof.
- 12. The tinctorial composition of claim 1 which also contains an organic solvent present in an amount ranging from 1 to 40 percent by weight based on the total weight of said composition.
- 13. The tinctorial composition of claim 1 which also contains one or more of a thickener, an antioxidant, a penetration agent, a sequestering agent, a buffer and a perfume.
- 14. The tinctorial composition of claim 1 in the form of a liquid, a cream, a gel or an aerosol packaged in the presence of a propellant.
- 15. A method for dyeing keratinous fibers comprising applying to said fibers in an amount sufficient to dye said fibers the said tinctorial composition of claim 1 in the presence of an oxidizing agent, leaving said composition in contact with said fibers for a period of time ranging from 10 to 40 minutes, rinsing said fibers, washing said fibers, rinsing said fibers and drying said fibers.
- 16. A tinctorial composition for dyeing keratinous fibers comprising in a medium suitable for dyeing said fibers at least one oxidation dyestuff precursor selected from a paraphenylenediamine, a paraaminophenol, a bis-phenylalkylenediamine, an orthoaminophenol, and an orthophenylenediamine, in combination with at least one heterocyclic coupler having the formula ##STR11## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl,
- R.sub.2 represents hydrogen or C.sub.1 -C.sub.4 lower alkyl,
- R.sub.3 represents hydrogen or formyl,
- X represents hydrogen or C.sub.1 -C.sub.4 alkyl with the proviso that at least one of X, R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen, and the salts thereof,
- said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 percent by weight based on the total weight of said composition, and the combined weight of said oxidation dyestuff precursor and said heterocyclic coupler ranging from 0.3 to 7 percent based on the total weight of said composition,
- said composition being free of any benzoquinone or naphthoquinone capable of oxidizing said heterocyclic coupler of formula I and being free of any iodide or nitrite in an amount capable of oxidizing said oxidation dyestuff precursor and the said heterocyclic coupler of formula I.
- 17. The composition of claim 16 wherein said heterocyclic coupler is selected from the group consisting of 4-hydroxy-5-methylindole and 4-hydroxy-3-formylindole.
- 18. A method for dyeing keratinous fibers comprising
- in a first step applying to said fibers a first composition comprising in a medium suitable for dyeing said fibers at least one oxidation dyestuff precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol, a bis-phenylalkylenediamine, an orthoaminophenol and an orthophenylenediamine,
- in a second step applying to said fibers a second composition comprising in a medium suitable for dyeing said fibers a heterocyclic coupler having the formula ##STR12## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl,
- R.sub.2 represents hydrogen, C.sub.1 -C.sub.4 lower alkyl, carboxyl or alkoxycarbonyl,
- R.sub.3 represents hydrogen, halogen, C.sub.1 -C.sub.4 lower alkyl, carboxyl, alkoxycarbonyl or formyl,
- X represents hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, acetylamino or di(C.sub.1 -C.sub.4) alkylaminomethyl,
- with the proviso that at least one of X, R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen,
- and the salts thereof, present in an amount ranging from 0.05 to 3.5 percent by weight and introducing an oxidizing agent into said composition applied to said fibers in said second step just before application thereof to said fibers, or
- in a third step applying to said fibers said oxidizing agent,
- the combined weight of said oxidation dyestuff precursor and said heterocyclic coupler applied to said fibers ranging from 0.3 to 7 percent based on the total weight of said first and second compositions.
- 19. In a process for the oxidation dyeing of keratinous fibers employing a composition containing at least one oxidation dye precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol, a bis-phenylalkylenediamine, an orthoaminophenol and an orthophenylenediamine in combination with a coupler, the improvement comprising, as said coupler for said oxidation dyeing of said keratinous fibers, a heterocyclic coupler having the formula ##STR13## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl,
- R.sub.2 represents hydrogen, C.sub.1 -C.sub.4 lower alkyl, carboxyl or alkoxycarbonyl,
- R.sub.3 represents hydrogen, halogen, C.sub.1 -C.sub.4 lower alkyl, carboxyl, alkoxycarbonyl or formyl,
- X represents hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, acetylamino or di(C.sub.1 -C.sub.4) alkylaminomethyl,
- with the proviso that at least one of X, R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen, and the salts thereof, present in an amount ranging from 0.05 to 3.5 percent by weight,
- and the combined weight of said oxidation dye precursor and said heterocyclic coupler used in said process ranging from 0.3 to 7 percent by weight of said composition.
- 20. A method for dyeing keratinous fibers comprising
- in a first step applying to said fibers a first composition comprising in a medium suitable for dyeing said fibers at least one oxidation dyestuff precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol, a bis-phenylalkylenediamine, an orthoaminophenol and an orthophenylenediamine,
- in a second step applying to said fibers a second composition comprising in a medium suitable for dyeing said fibers, a heterocyclic coupler having the formula ##STR14## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl,
- R.sub.2 represents hydrogen or C.sub.1 -C.sub.4 lower alkyl,
- R.sub.3 represents hydrogen or formyl,
- X represents hydrogen or C.sub.1 -C.sub.4 alkyl with the proviso that at least one of X, R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen, and the salts thereof, present in an amount ranging from 0.05 to 3.5 percent by weight and introducing an oxidizing agent into said composition applied to said fibers in said second step just before application thereof to said fibers, or
- in a third step applying to said fibers said oxidizing agent,
- the combined weight of said oxidation dyestuff precursor and said heterocyclic coupler applied to said fibers ranging from 0.3 to 7 percent based on the total weight of said first and second compositions.
- 21. In a process for the oxidation dyeing of keratinous fibers employing a composition containing at least one oxidation dye precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol, a bis-phenylalkylenediamine, an orthoaminophenol and an orthophenylenediamine in combination with a coupler, the improvement comprising, as said coupler for said oxidation dyeing of said keratinous fibers, a heterocyclic coupler having the formula ##STR15## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl,
- R.sub.2 represents hydrogen or C.sub.1 -C.sub.4 lower alkyl,
- R.sub.3 represents hydrogen or formyl,
- X represents hydrogen or C.sub.1 -C.sub.4 alkyl with the proviso that at least one of X, R.sub.1, R.sub.2 and R.sub.3 is other than hydrogen, and the salts thereof, present in an amount ranging from 0.05 to 3.5 percent by weight,
- and the combined weight of said oxidation dye precursor and said heterocyclic coupler used in said process ranging from 0.3 to 7 percent by weight of said composition.
Priority Claims (1)
Number |
Date |
Country |
Kind |
8914794 |
Nov 1989 |
FRX |
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Parent Case Info
This is a continuation of application Ser. No. 07/933,937, filed Aug. 24, 1992, now abandoned which is a continuation of application Ser. No. 07/611,139 filed Nov. 9, 1990, now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4013404 |
Parent et al. |
Mar 1977 |
|
5034015 |
Junino et al. |
Jul 1991 |
|
5131911 |
Lang et al. |
Jul 1992 |
|
Foreign Referenced Citations (5)
Number |
Date |
Country |
0271186 |
Jun 1988 |
EPX |
0360638 |
Mar 1990 |
EPX |
2636235 |
Mar 1990 |
FRX |
2636237 |
Mar 1990 |
FRX |
3031709 |
Apr 1982 |
DEX |
Non-Patent Literature Citations (1)
Entry |
English Language Translation of DE, 3,031,709, Wella AG, Apr. 22, 1982, pp. 1-12. |
Continuations (2)
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Number |
Date |
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Parent |
933937 |
Aug 1992 |
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Parent |
611139 |
Nov 1990 |
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