US4200432A
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Dye composition containing oxidation dye and diphenylamine
Assignee: L'Oréal SA
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Filing: 1977-11-21
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Granted: 1980-04-29
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Expires: 1997-11-21
Abstract
Abstract A hair dye composition comprising at least one oxidation dye and at least one diphenylamine of the formula <IMAGE> wherein R1 and R4 each independently represent hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, acylamino or ureido; R2 and R3 each independently represent hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, amino, N-alkylamino wherein the alkyl has 1-6 carbon atoms, N-hydroxyalkylamino wherein the alkyl has 1-6 carbon atoms, acylamino, N-carbamylalkylamino wherein the alkyl has 1-6 carbon atoms or ureido; R5 represents hydrogen, halogen, lower alkyl having 1-6 carbon atoms or lower alkoxy having 1-6 carbon atoms; R6, R7 and R8, each independently represent hydrogen, halogen, lower alkyl having 1-6 carbon atoms or lower alkoxy having 1-6 carbon atoms; Y represents hydroxy or amino; and Z represents hydroxy or <IMAGE> wherein R9 and R10 each independently represents hydrogen, lower alkyl containing 1-6 carbon atoms, hydroxyalkyl containing 1-6 carbon atoms, carbamyl alkyl wherein the alkyl has 1-6 carbon atoms, amino alkyl wherein the alkyl has 1-6 carbon atoms, monoalkylamino alkyl wherein each alkyl has 1-6 carbon atoms, dialkylamino alkyl wherein each alkyl has 1-6 carbon atoms, acylaminoalkyl wherein the alkyl has 1-6 carbon atoms, alkylsulfonamido alkyl wherein each alkyl has 1-6 carbon atoms, arylsulfonamidoalkyl wherein the alkyl has 1-6 carbon atoms, sulfoalkyl wherein the alkyl has 1-6 carbon atoms, piperidinoalkyl wherein the alkyl has 1-6 carbon atoms or morpholinoalkyl wherein the alkyl has 1-6 carbon atoms; or a salt thereof.
Inventors
- 👤 Gregoire Kalopissis
- 👤 Andree Bugaut
- 👤 Francoise Estradier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 00:22
CPC Classifications
C; C09; C09B; C09B53/00; C09B53/02; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/41; A61K8/413; A61Q; A61Q5/00; A61Q5/10
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
463 words
A hair dye composition in the form of an aqueous or hydroalcoholic solution, a cream, an emulsion, a dispersion or an aerosol comprising an oxidation dye and a diphenylamine selected from the group consisting of (i) a diphenylamine of the formula ##STR10## wherein R 1 and R 4 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, acetylamino and ureido; R 2 and R 3 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, amino, N-alkylamino wherein the alkyl moiety has 1-6 carbon atoms, N-hydroxyalkylamino wherein the alkyl moiety has 1-6 carbon atoms, acetylamino, N-carbamylalkylamino wherein the alkyl moiety has 1-6 carbon atoms and ureido; R 5 represents a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms and lower alkoxy having 1-6 carbon atoms; R 6 , R 7 and R 8 , each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms and lower alkoxy having 1-6 carbon atoms; Y represents a member selected from the group consisting of hydroxy and amino; and Z represents a member selected from the group consisting of hydroxy and ##STR11## wherein R 9 and R 10 each independently represent a member selected from the group consisting of hydrogen, lower alkyl containing 1-6 carbon atoms, hydroxyalkyl containing 1-6 carbon atoms, carbamyl alkyl wherein the alkyl moiety has 1-6 carbon atoms, amino alkyl wherein the alkyl moiety has 1-6 carbon atoms, monoalkylamino alkyl wherein each of the alkyl moieties has 1-6 carbon atoms, dialkylamino alkyl wherein each of the alkyl moieties has 1-6 carbon atoms, acylaminoalkyl wherein the alkyl moiety has 1-6 carbon atoms, alkylsulfonamido alkyl wherein each of the alkyl moieties has 1-6 carbon atoms, arylsulfonamidoalkyl wherein the alkyl moiety has 1-6 carbon atoms, sulfoalkyl wherein the alkyl moiety has 1-6 carbon atoms and piperidinoalkyl wherein the alkyl moiety has 1-6 carbon atoms, with the proviso that R 2 and R 3 are other than amino or acetylamino (1) when (a) Z is OH, (b) Y is amino and (c) each of R 1 and R 4 is hydrogen or alkyl or (2) when (d) Z is OH, (e) Y is amino, (f) R 1 or R 4 is alkoxy, and (g) each of R 5 , R 6 , R 7 and R 8 is hydrogen, alkyl or halogen, one of R 5 , R 6 , R 7 and R 8 being other than hydrogen, or (ii) a salt of the diphenylamine of (i), said diphenylamine and said oxidation dye being present in a tinctorially effective amount.
Claim 2
Dependent Claim
463 words
A hair dye composition in the form of an aqueous or hydroalcoholic solution, a cream, an emulsion, a dispersion or an aerosol comprising an oxidation dye and a diphenylamine selected from the group consisting of (i) a diphenylamine of the formula ##STR10## wherein R 1 and R 4 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, acetylamino and ureido; R 2 and R 3 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, amino, N-alkylamino wherein the alkyl moiety has 1-6 carbon atoms, N-hydroxyalkylamino wherein the alkyl moiety has 1-6 carbon atoms, acetylamino, N-carbamylalkylamino wherein the alkyl moiety has 1-6 carbon atoms and ureido; R 5 represents a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms and lower alkoxy having 1-6 carbon atoms; R 6 , R 7 and R 8 , each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms and lower alkoxy having 1-6 carbon atoms; Y represents a member selected from the group consisting of hydroxy and amino; and Z represents a member selected from the group consisting of hydroxy and ##STR11## wherein R 9 and R 10 each independently represent a member selected from the group consisting of hydrogen, lower alkyl containing 1-6 carbon atoms, hydroxyalkyl containing 1-6 carbon atoms, carbamyl alkyl wherein the alkyl moiety has 1-6 carbon atoms, amino alkyl wherein the alkyl moiety has 1-6 carbon atoms, monoalkylamino alkyl wherein each of the alkyl moieties has 1-6 carbon atoms, dialkylamino alkyl wherein each of the alkyl moieties has 1-6 carbon atoms, acylaminoalkyl wherein the alkyl moiety has 1-6 carbon atoms, alkylsulfonamido alkyl wherein each of the alkyl moieties has 1-6 carbon atoms, arylsulfonamidoalkyl wherein the alkyl moiety has 1-6 carbon atoms, sulfoalkyl wherein the alkyl moiety has 1-6 carbon atoms and piperidinoalkyl wherein the alkyl moiety has 1-6 carbon atoms, with the proviso that R 2 and R 3 are other than amino or acetylamino (1) when (a) Z is OH, (b) Y is amino and (c) each of R 1 and R 4 is hydrogen or alkyl or (2) when (d) Z is OH, (e) Y is amino, (f) R 1 or R 4 is alkoxy, and (g) each of R 5 , R 6 , R 7 and R 8 is hydrogen, alkyl or halogen, one of R 5 , R 6 , R 7 and R 8 being other than hydrogen, or (ii) a salt of the diphenylamine of (i), said diphenylamine and said oxidation dye being present in a tinctorially effective amount.
Claim 3
Dependent Claim
24 words
The composition of claim 1 wherein said oxidation dye is selected from the group consisting of paraphenylenediamine, para amino phenol and a heterocyclic base.
Claim 4
Dependent Claim
232 words
The composition of claim 2 wherein said paraphenylenediamine has the formula ##STR12## wherein R 11 and R 12 each independently represent a member selected from the group consisting of hydrogen, straight or branch chained lower alkyl having 1-6 carbon atoms, hydroxy alkyl having 1-6 carbon atoms and one or more hydroxy groups, piperidinoalkyl wherein the alkyl moiety has 1-6 carbon atoms, carbamylalkyl wherein the alkyl moiety has 1-6 carbon atoms, dialkyl carbamylalkyl wherein each alkyl moiety has 1-6 carbon atoms, aminoalkyl having 1-6 carbon atoms, monoalkylaminoalkyl wherein each alkyl moiety has 1-6 carbon atoms, dialkylaminoalkyl wherein each alkyl moiety has 1-6 carbon atoms, ω-amino-sulfonylalkyl wherein the alkyl moiety has 1-6 carbon atoms, carboxyalkyl wherein the alkyl moiety has 1-6 carbon atoms, alkylsulfonamidoalkyl wherein each alkyl has 1-6 carbon atoms, arylsulfonamidoalkyl wherein the alkyl moiety has 1-6 carbon atoms, morpholinoalkyl wherein the alkyl moiety has 1-6 carbon atoms, acylaminoalkyl wherein the alkyl moiety has 1-6 carbon atoms and sulfoalkyl wherein the alkyl moiety has 1-6 carbon atoms, or R 11 and R 12 together with the nitrogen atom to which they are attached form a member selected from the group consisting of morpholino and piperidinyl; and R 13 , R 14 , R 15 and R 16 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl containing 1-6 carbon atoms and lower alkoxy containing 1-6 carbon atoms.
Claim 5
Dependent Claim
83 words
The composition of claim 2, wherein said paraphenylenediamine is selected from the group consisting of paraphenylenediamine, paratolylenediamine, methoxy paraphenylenediamine, chloroparaphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,5-dimethyl paraphenylenediamine, 2-methyl-5-methoxy paraphenylenediamine, 2,6-dimethyl-5-methoxy paraphenylenediamine, N,N-dimethyl paraphenylenediamine, 3-methyl-4-amino-N,N-(diethyl) aniline, N,N-(di-β-hydroxyethyl) paraphenylenediamine, 3-methyl-4-amino-N,N-(di-β-hydroxyethyl) aniline, 3-chloro-4-amino-N,N-(di-β-hydroxyethyl) aniline, 4-amino-N,N-(ethyl, carbamylmethyl) aniline, 3-methyl-4-amino-N,N-(ethyl, carbamylmethyl) aniline, 4-amino-N,N-(ethyl, morpholinoethyl) aniline, 3-methyl-4-amino-N,N-(ethyl morpholinoethyl) aniline, 4-amino-N,N-(ethyl, acetylaminoethyl) aniline, 3-methyl-4-amino-N,N-(ethyl, acetylaminoethyl) aniline, 4-amino-N,N-(ethyl, mesylaminoethyl) aniline, 3-methyl-4-amino-N,N-(ethyl, mesylaminoethyl) aniline, 4-amino-N,N-(ethyl, β-sulfoethyl) aniline, 3-methyl-4-amino-N,N-(ethyl, β-sulfoethyl) aniline, N-[(4'-amino)phenyl]morpholine, N-[(4'-amino)phenyl]piperidine, 4-amino-N,N-(ethyl, piperidinoethyl) aniline, 3-methyl-4-amino-N-methyl aniline, 2-chloro-4-amino-N,N-(ethyl, sulfonamidoethyl) aniline, 2-chloro-4-amino-N-(ethyl) aniline and 2-methyl-4-amino-N-(β-hydroxyethyl) aniline.
Claim 6
Dependent Claim
37 words
The composition of claim 2 wherein said para amino phenol is selected from the group consisting of para amino phenol, 2-methyl-4-amino phenol, 3-methyl-4-amino phenol, 2-chloro-4-amino phenol, 3-chloro-4-amino phenol, 2,6-dimethyl-4-amino phenol, 3,5-dimethyl-4-amino phenol, 2,3-dimethyl-4-amino phenol and 2,5-dimethyl-4-amino phenol.
Claim 7
Dependent Claim
28 words
The composition of claim 2 wherein said heterocyclic base is selected from the group consisting of 2,5-diamino pyridine, 2-dimethyl amino-5-amino pyridine, 2-diethylamino-5-amino pyridine, 3-methyl-7-amino phenomorpholine and 5-amine indole.
Claim 8
Dependent Claim
25 words
The composition of claim 1 wherein said salt of the diphenylamine is selected from the group consisting of the hydrochloride, the hydrobromide and sulfate thereof.
Claim 9
Dependent Claim
25 words
The composition of claim 1 which also includes a coupler in an amount of about 0.001 to 5 percent by weight of the total composition.
Claim 10
Dependent Claim
174 words
The composition of claim 8 wherein said coupler has the formula ##STR13## wherein R 17 and R 18 each independently represent a member selected from the group consisting of hydroxy and --NHR wherein R represents a member selected from the group consisting of hydrogen, acyl, ureido, carbalkoxy wherein the alkoxy moiety has 1-6 carbon atoms, carbamylalkyl, wherein the alkyl moiety has 1-6 carbon atoms, alkyl having 1-6 carbon atoms, dialkylcarbamylalkyl wherein each alkyl moiety has 1-6 carbon atoms and hydroxy alkyl having 1-6 carbon atoms; R 17 and R 18 each independently can also represent a member selected from the group of hydrogen, alkoxy containing 1-6 carbon atoms and alkyl containing 1-6 carbon atoms with the proviso that at least one of R 17 and R 18 is hydroxy; and R 19 and R 20 each independently represent a member selected from the group consisting of hydrogen, straight or branched alkyl containing 1-6 carbon atoms, alkoxy containing 1-6 carbon atoms, halogen, amino, aminoalkyl wherein the alkyl moiety has 1-6 carbon atoms, acylamino and ureido.
Claim 11
Dependent Claim
31 words
The composition of claim 9 wherein said coupler is selected from the group consisting of resorcinol, metaamino phenol, 2,4-diamino anisole, 2-methyl-5-ureido phenol, 2,6-dimethyl-5-amino phenol, 2-methyl-5-acetylamino phenol, 2,6-dimethyl-5-acetylamino phenol and 3-amino-4-methoxy phenol.
Claim 12
Dependent Claim
30 words
The composition of claim 8 wherein said coupler is a member selected from the group consisting of 6-hydroxy phenomorpholine, 6-amino phenomorpholine, a pyridine derivative, a diketone compound and a pyrazolone.
Claim 13
Dependent Claim
34 words
The composition of claim 1 which also includes a direct hair dye selected from the group consisting of an azo dye, an anthraquinone dye, a nitro-benzene dye, an indamine, an indoaniline and an indophenol.
Claim 14
Dependent Claim
14 words
The composition of claim 1 which also includes an effective amount of a glycol.
Claim 15
Dependent Claim
26 words
The composition of claim 13 wherein said glycol is selected from the group consisting of butyl glycol, propylene glycol and the monomethyl ester of diethylene glycol.
Claim 16
Dependent Claim
22 words
The composition of claim 1 wherein the alcohol of the hydroalcoholic solution is selected from the group consisting of ethanol and isopropanol.
Claim 17
Dependent Claim
13 words
The composition of claim 1 having a pH of about 5 to 11.
Claim 18
Dependent Claim
14 words
The composition of claim 16 wherein said pH ranges from about 8 to 10.
Claim 19
Dependent Claim
39 words
A composition comprising the hair dye composition of claim 1 in admixture with an oxidizing agent, said oxidizing agent being present in an amount ranging from 1-3 parts by weight per part by weight of said hair dye composition.
Claim 20
Dependent Claim
25 words
The composition of claim 18 wherein said oxidizing agent is selected from the group consisting of hydrogen peroxide, urea peroxide, a persulfate and a perborate.
Claim 21
Dependent Claim
25 words
The composition of claim 1 wherein said diphenylamine is present in an amount of about 0.01 to 3 percent by weight of the total composition.
Claim 22
Dependent Claim
22 words
The composition of claim 1 wherein said oxidation dye is present in an amount of about 0.03 to 2 percent by weight.
Claim 23
Dependent Claim
21 words
The composition of claim 8 wherein said coupler is present in an amount of about 0.015 to 1 percent by weight.
Claim 24
Dependent Claim
16 words
The composition of claim 1 which also includes an effective amount of a surface active agent.
Claim 25
Dependent Claim
17 words
The composition of claim 1 which also includes an effective amount of a cosmetic film forming resin.
Claim 26
Dependent Claim
15 words
The composition of claim 1 which also includes an effective amount of a reducing agent.
Claim 27
Dependent Claim
14 words
The composition of claim 1 which also includes an effective amount of a sequesterant.
Claim 28
Dependent Claim
15 words
The composition of claim 1 which also includes an effective amount of an alkalizing agent.
Claim 29
Dependent Claim
15 words
The composition of claim 1 which also includes an effective amount of an acidifying agent.
Claim 30
Dependent Claim
48 words
The hair dye composition of claim 1 wherein said diphenylamine is present in an amount of about 0.005 to 5 percent by weight of the total composition and said oxidation dye is present in an amount of about 0.001 to 5 percent by weight of the total composition.
Claim 31
Dependent Claim
25 words
The composition of claim 1, wherein said diphenylamine is present in an amount of about 0.005 to 5 percent by weight of the total composition.
Claim 32
Dependent Claim
27 words
The composition of claim 1, wherein said oxidation dye is present in an amount of about 0.001 to 5 percent by weight of the total composition. PG,96
Claim 33
Dependent Claim
53 words
A process for dyeing hair comprising impregnating hair to be dyed with the composition of claim 21 in an amount effective to dye said hair, permitting said composition to remain in contact with said hair for a period of time ranging from 5 to 40 minutes, rinsing said hair and shampooing said hair.
Claim 34
Dependent Claim
219 words
A hair dye composition comprising an aqueous or hydroalcoholic solution of an oxidation dye and a diphenylamine selected from the group consisting of (i) a diphenylamine of the formula ##STR14## wherein Y is hydroxy or amino, and R 1 -R 8 and Z are selected from the combinations consisting of (a) R 1 is CH 3 , R 2 is H, R 3 is NH 2 , R 4 is H, R 5 , R 6 , R 7 and R 8 are each H and Z is N,N-dimethylamino, (b) R 1 is H, R 2 is NH 2 , R 3 is H, R 4 is OCH 3 , R 5 , R 6 , R 7 and R 8 are each H and Z is OH and (c) R 1 is H, R 2 is NH 2 , R 3 is H, R 4 is OCH 3 , R 5 , R 6 , R 7 and R 8 are each H and Z is N,N-(ethyl, carbamylmethyl) amino; and (ii) a salt of the diphenylamine of (i), said diphenylamine being present in an amount of about 0.005 to 5 percent by weight of the total composition and said oxidation dye being present in an amount of about 0.001 to 5 percent by weight of the total composition.
Claim 35
Dependent Claim
219 words
A hair dye composition comprising an aqueous or hydroalcoholic solution of an oxidation dye and a diphenylamine selected from the group consisting of (i) a diphenylamine of the formula ##STR14## wherein Y is hydroxy or amino, and R 1 -R 8 and Z are selected from the combinations consisting of (a) R 1 is CH 3 , R 2 is H, R 3 is NH 2 , R 4 is H, R 5 , R 6 , R 7 and R 8 are each H and Z is N,N-dimethylamino, (b) R 1 is H, R 2 is NH 2 , R 3 is H, R 4 is OCH 3 , R 5 , R 6 , R 7 and R 8 are each H and Z is OH and (c) R 1 is H, R 2 is NH 2 , R 3 is H, R 4 is OCH 3 , R 5 , R 6 , R 7 and R 8 are each H and Z is N,N-(ethyl, carbamylmethyl) amino; and (ii) a salt of the diphenylamine of (i), said diphenylamine being present in an amount of about 0.005 to 5 percent by weight of the total composition and said oxidation dye being present in an amount of about 0.001 to 5 percent by weight of the total composition.
Claim 36
Dependent Claim
85 words
A hair dye composition comprising an aqueous or hydroalcoholic solution of an oxidation dye and a diphenylamine selected from the group consisting of (i) a diphenylamine of the formula ##STR15## wherein Y is hydroxy or amino; and (ii) a salt of the diphenylamine of (i), said diphenylamine being present in an amount of about 0.005 to 5 percent by weight of the total composition and said oxidation dye being present in an amount of about 0.001 to 5 percent by weight of the total composition.
Claim 37
Dependent Claim
85 words
A hair dye composition comprising an aqueous or hydroalcoholic solution of an oxidation dye and a diphenylamine selected from the group consisting of (i) a diphenylamine of the formula ##STR15## wherein Y is hydroxy or amino; and (ii) a salt of the diphenylamine of (i), said diphenylamine being present in an amount of about 0.005 to 5 percent by weight of the total composition and said oxidation dye being present in an amount of about 0.001 to 5 percent by weight of the total composition.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-29 | 1983-10-29 | 1984-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-29 | 1987-10-29 | 1988-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-29 | 1991-10-29 | 1992-04-29 | $7700.00 | Window Closed / Lapsed |