US3985499A
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Diazamerocyanines for dyeing keratinous fibers
Assignee: L'Oréal SA
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Filing: 1975-03-03
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Granted: 1976-10-12
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Expires: 1995-03-03
Abstract
Abstract Some novel diazo compounds, and salts thereof, useful for dyeing keratinous fibers, particularly human hair are disclosed. Illustrative of these compounds are the methyl sulfate salts of 1'-(4'-N,N-dimethylaminobenzene) 2-azo 4-cyano 1-methyl pyridinium methyl sulfate and 1'-(4'-amino 8'-hydroxy naphthalene) 2-azo 1-methyl pyridinium. Hair setting lotions, hair dye compositions and hair lacquers containing these compounds, preferably in alcoholic solutions, are also disclosed.
Inventors
- 👤 Gerard Lang
- 👤 Andree Bugaut
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 06:25
CPC Classifications
C; C09; C09B; C09B23/00; C09B23/16; C09B23/162; C09B23/166; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/41; A61K8/413; A61K8/49; A61K8/4906; A61K8/4926; A61K8/494; A61K8/4946; A61Q; A61Q5/00; A61Q5/10; Y; Y10; Y10S; Y10S424/00; Y10S424/02; Y10S8/00; Y10S8/916; Y10S8/917
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
598 words
A dye composition for dyeing keratinous fibers comprising an aqueous solution having a pH of between about 3 and about 8, of from about 0.0001 to about 5% by weight of at least one diazamerocyanine dye, including the mesomorphic forms thereof, having the formula A=N--N=B wherein A represents a nitrogen heterocycle selected from the group consisting of ##SPC80## wherein R represents a member selected from the group consisting of lower alkyl having 1-4 carbon atoms and phenyl; X represents a member selected from the group consisting of sulfur, --NR'--, wherein R' represents lower alkyl having 1-4 carbon atoms, --CR' 9 =CR' 10 wherein R' 9 is hydrogen, alkyl of 1 to 4 carbon atoms or cyano and wherein R' 10 is hydrogen or alkyl of 1 to 4 carbon atoms, and --C(R")(R")--, wherein each R" is independently selected from the group consisting of hydrogen and lower alkyl having 1-4 carbon atoms; Z represents a member selected from the group consisting of --CH=CH-- and --NR'", wherein R'" represents lower alkyl having 1-4 carbon atoms, R 7 represents a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms, cyano and phenyl, R 8 represents a member selected from the group consisting of hydrogen, halogen and lower alkyl having 1-4 carbon atoms, provided that R 7 and R 8 , when taken together with the carbon atoms to which they are linked, represent benzene; B represents a member selected from the group consisting of i. 1-phenyl-3-methyl-5-pyrazolone, ii. a cycle of the formula ##SPC81## wherein Y represents a member selected from the group consisting of oxygen and ##EQU1## wherein R 1 and R 2 each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms, hydroxyalkyl having 1-4 carbon atoms and phenyl, and Z - is an anion derived from a member selected from the group consisting of an inorganic acid and an organic acid, R 3 represents a member selected from the group consisting of hydrogen, lower alkyl, lower alkoxy and phenylcarbamyl, R 4 and R 6 each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms and lower alkoxy having 1-4 carbon atoms, and R 5 represents a member selected from the group consisting of hydrogen, halogen, alkyl of 1 to 4 carbon atoms, nitro, amino, acetylamino; R 5 and R 6 together with the carbon atoms to which they are attached being benzene or hydroxybenzene, iii. a cycle having the formula ##SPC82## wherein R 1 and R 9 , together with the nitrogen and carbon atoms to which they are attached, represent morpholine in which case R 10 is hydrogen and R 2 represents a member selected from the group consisting of hydrogen and lower alkyl having 1-4 carbon atoms, and wherein R 2 and R 10 , when taken together with the nitrogen and carbon atoms to which they are attached, represent morpholine in which case R 9 is hydrogen and R 1 represents a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms and acyl having 2 to 5 carbon atoms, and R 11 represents a member selected from the group consisting of hydrogen and lower alkyl having 1-4 carbon atoms, and iv. a cycle having the formula ##SPC83## wherein R 1 , r 2 , r 9 , r 10 and R 11 have the meaning given above and X - represents an anion derived from a member selected from the group consisting of an inorganic acid and an organic acid.
Claim 2
Dependent Claim
598 words
A dye composition for dyeing keratinous fibers comprising an aqueous solution having a pH of between about 3 and about 8, of from about 0.0001 to about 5% by weight of at least one diazamerocyanine dye, including the mesomorphic forms thereof, having the formula A=N--N=B wherein A represents a nitrogen heterocycle selected from the group consisting of ##SPC80## wherein R represents a member selected from the group consisting of lower alkyl having 1-4 carbon atoms and phenyl; X represents a member selected from the group consisting of sulfur, --NR'--, wherein R' represents lower alkyl having 1-4 carbon atoms, --CR' 9 =CR' 10 wherein R' 9 is hydrogen, alkyl of 1 to 4 carbon atoms or cyano and wherein R' 10 is hydrogen or alkyl of 1 to 4 carbon atoms, and --C(R")(R")--, wherein each R" is independently selected from the group consisting of hydrogen and lower alkyl having 1-4 carbon atoms; Z represents a member selected from the group consisting of --CH=CH-- and --NR'", wherein R'" represents lower alkyl having 1-4 carbon atoms, R 7 represents a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms, cyano and phenyl, R 8 represents a member selected from the group consisting of hydrogen, halogen and lower alkyl having 1-4 carbon atoms, provided that R 7 and R 8 , when taken together with the carbon atoms to which they are linked, represent benzene; B represents a member selected from the group consisting of i. 1-phenyl-3-methyl-5-pyrazolone, ii. a cycle of the formula ##SPC81## wherein Y represents a member selected from the group consisting of oxygen and ##EQU1## wherein R 1 and R 2 each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms, hydroxyalkyl having 1-4 carbon atoms and phenyl, and Z - is an anion derived from a member selected from the group consisting of an inorganic acid and an organic acid, R 3 represents a member selected from the group consisting of hydrogen, lower alkyl, lower alkoxy and phenylcarbamyl, R 4 and R 6 each independently represent a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms and lower alkoxy having 1-4 carbon atoms, and R 5 represents a member selected from the group consisting of hydrogen, halogen, alkyl of 1 to 4 carbon atoms, nitro, amino, acetylamino; R 5 and R 6 together with the carbon atoms to which they are attached being benzene or hydroxybenzene, iii. a cycle having the formula ##SPC82## wherein R 1 and R 9 , together with the nitrogen and carbon atoms to which they are attached, represent morpholine in which case R 10 is hydrogen and R 2 represents a member selected from the group consisting of hydrogen and lower alkyl having 1-4 carbon atoms, and wherein R 2 and R 10 , when taken together with the nitrogen and carbon atoms to which they are attached, represent morpholine in which case R 9 is hydrogen and R 1 represents a member selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms and acyl having 2 to 5 carbon atoms, and R 11 represents a member selected from the group consisting of hydrogen and lower alkyl having 1-4 carbon atoms, and iv. a cycle having the formula ##SPC83## wherein R 1 , r 2 , r 9 , r 10 and R 11 have the meaning given above and X - represents an anion derived from a member selected from the group consisting of an inorganic acid and an organic acid.
Claim 3
Dependent Claim
25 words
The dye composition of claim 1 which also contains a low molecular weight alkanol present in an amount of 20-70 weight percent of said composition.
Claim 4
Dependent Claim
24 words
The dye composition of claim 1, wherein R 5 and R 6 together with the carbon atoms to which they are attached is benzene.
Claim 5
Dependent Claim
40 words
The dye composition of claim 1 wherein R 5 and R 6 together with the carbon atoms to which they are attached is hydroxybenzene, and each of R 1 , R 2 , R 3 and R 4 is hydrogen.
Claim 6
Dependent Claim
22 words
The dye composition of claim 2 wherein said low molecular weight alkanol is selected from the group consisting of ethanol and isopropanol.
Claim 7
Dependent Claim
39 words
The dye composition of claim 1 also including a dye selected from the group consisting of an azo dye other than the dye of claim 1, an anthraquinone dye, a nitrobenzene dye, an indophenol, and indoaniline and an indamine.
Claim 8
Dependent Claim
46 words
A process of dyeing keratinous fibers, comprising impregnating said fibers to be dyed with the composition of claim 1, permitting said composition to remain in contact with said fibers for a period ranging from about 3 to 30 minutes, rinsing said fibers and drying said fibers.
Claim 9
Dependent Claim
14 words
The dye composition of claim 2 which also contains a cosmetic film forming resin.
Claim 10
Dependent Claim
14 words
The dye composition of claim 5 which also contains a cosmetic film forming resin.
Claim 11
Dependent Claim
46 words
The dye composition of claim 8 wherein said cosmetic film forming resin is selected from the group consisting of polyvinyl pyrrolidone, a copolymer of cortonic acid and vinyl acetate, a copolymer of vinyl pyrrolidone and vinyl acetate, and a copolymer of maleic anhydride and butylvinyl ether.
Claim 12
Dependent Claim
27 words
The dye composition of claim 8 wherein said film forming cosmetic resin is present in an amount of about 1 to 3% by weight of said composition.
Claim 13
Dependent Claim
20 words
The composition of claim 1, wherein said dye is present in an amount between about 0.01 and 1.5 weight percent.
Claim 14
Dependent Claim
19 words
The composition of claim 8, wherein said dye is present in an amount between about 0.01 and 1.5 percent.
Claim 15
Dependent Claim
12 words
The composition of claim 1 which further includes a surface active agent.
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) | 1979-10-12 | 1980-04-12 | 1980-10-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-12 | 1984-04-12 | 1984-10-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-12 | 1988-04-12 | 1988-10-12 | $7700.00 | Window Closed / Lapsed |