US4171203A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hair dye compositions containing 3,5-diamino-2-substituted-alkylbenzenes
Assignee: Henkel AG and Co KGaA
•
Filing: 1977-06-20
•
Granted: 1979-10-16
•
Expires: 1997-06-20
Abstract
Abstract Dyestuffs of the oxidizable developer-coupler type wherein the coupler is a 3,5-diamino-2-substituted-alkylbenzene of the formula <IMAGE> wherein R1 is straight- or branched-chain alkyl of 1-8 carbon atoms, R2 is a straight- or branched-chain alkyl of 1-8 carbon atoms, phenyl, or phenyl substituted by alkyl of 1-4 carbon atoms or halogen atoms and the inorganic and organic salts thereof are very satisfactory for coloring hair. They are readily oxidized by atmospheric oxygen at room temperature without a catalyst, and they provide intense, bright and fast dyeings in a short tie. They are applied in conventional manner from an aqueous medium.
Inventors
- 👤 David Rose
- 👤 Erwin Weinrich
- 👤 Edgar Lieske
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 04:55
CPC Classifications
A; A61; A61Q; A61Q5/00; A61Q5/10; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/41; A61K8/411
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
154 words
An aqueous preparation of the developer-coupler type for the dyeing of hair, consisting essentially of (a) 0.2 to 5% by weight of a developer-coupler comtination of, as a coupler, (A) a 3,5-diamino-2-substituted alkyl benzene of the formula ##STR5## wherein R 1 is a straight- or branched-chain alkyl of 1 to 8 carbon atoms and R 2 is a member selected from the group consisting of a straight- or branched-chain alkyl radical of 1 to 8 carbon atoms, phenyl, and phenyl substituted by a member selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and halogen atoms, or (B) a water-soluble acid addition salt of (A), and a conventional developer therefor, said coupler and said developer being present in the molar range of about 2:1 to 1:2; (b) 0% to 30% by weight of a surfactant; (c) 0% to 25% by weight of a thickener; and (d) the remainder water.
Claim 2
Dependent Claim
154 words
An aqueous preparation of the developer-coupler type for the dyeing of hair, consisting essentially of (a) 0.2 to 5% by weight of a developer-coupler comtination of, as a coupler, (A) a 3,5-diamino-2-substituted alkyl benzene of the formula ##STR5## wherein R 1 is a straight- or branched-chain alkyl of 1 to 8 carbon atoms and R 2 is a member selected from the group consisting of a straight- or branched-chain alkyl radical of 1 to 8 carbon atoms, phenyl, and phenyl substituted by a member selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and halogen atoms, or (B) a water-soluble acid addition salt of (A), and a conventional developer therefor, said coupler and said developer being present in the molar range of about 2:1 to 1:2; (b) 0% to 30% by weight of a surfactant; (c) 0% to 25% by weight of a thickener; and (d) the remainder water.
Claim 3
Dependent Claim
20 words
The preparation of claim 1, wherein R 1 and R 2 are alkyl radicals of 1 to 4 carbon atoms.
Claim 4
Dependent Claim
23 words
The preparation of claim 1 wherein R 1 is an alkyl radical of 1 to 4 carbon atoms and R 2 is phenyl.
Claim 5
Dependent Claim
44 words
The preparation of claim 1 wherein R 1 is an alkyl radical of 1 to 4 carbon atoms and R 2 is phenyl substituted by a member selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and halogen atoms.
Claim 6
Dependent Claim
31 words
The preparation of claim 1 wherein R 1 is an alkyl radical of 1 to 4 carbon atoms and R 2 is an alkyl radical of 4 to 8 carbon atoms.
Claim 7
Dependent Claim
10 words
The preparation of claim 1 wherein the coupler is 3,5-diamino-2-methoxytoluene.
Claim 8
Dependent Claim
17 words
The preparation of claim 1 wherein the coupler is in the form of a dermatologically-acceptable water-soluble salt.
Claim 9
Dependent Claim
191 words
The preparation of claim 1 wherein the developer is (A) a tetraaminopyrimidine of the formula ##STR6## wherein R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each selected from the group consisting of hydrogen, phenyl, alkyl having 1 to 4 carbon atoms, phenylalkyl having 7 to 10 carbon atoms, phenylalkenyl having 7 to 10 carbon atoms, X--(CH.sub.2).sub.n -- wherein n is an integer from 1 to 4, and X is selected from the group consisting of hydroxyl, halogen and NR 9 R 10 -- in which R 9 and R 10 are each independently hydrogen or alkyl having 1 to 4 carbon atoms, and together with the nitrogen atom R 9 and R 10 can form a heterocyclic ring optionally containing an additional nitrogen atom or oxygen atom, and wherein R 3 and R 4 , R 5 and R 6 , and R 7 and R 8 , together with the nitrogen atom can form a five to six membered heterocyclic ring optionally containing another nitrogen or oxygen atom in the ring and (B) a water-soluble acid addition salt of (A).
Claim 10
Dependent Claim
130 words
The preparation of claim 8, wherein in the developer R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, n-propyl, butyl, phenyl, benzyl, benzylidene and --(CH 2 ) n --X, and wherein R 3 and R 4 , or R 5 and R 6 , or R 7 and R 8 , together with the nitrogen atom form a substituent selected from the group consisting of piperidino and morpholino; and wherein n is 1, 2 or 3 and X is selected from the group consisting of hydroxyl, halogen and --NR 9 R 10 in which R 9 and R 10 are each hydrogen or alkyl having 1 to 4 carbon atoms.
Claim 11
Dependent Claim
54 words
The preparation of claim 8 wherein the coupler is selected from the group consisting of 3,5-diamino-2-methoxytoluene, 3,5-diamino-2-ethoxytoluene, 3,5-diamino-2-methoxyethyl-benzene, 3,5-diamino-2-octyloxytoluene, 3,5-diamino-2-phenyloxytoluene, and the water-soluble acid addition salts of the above couplers, and the developer is selected from the group consisting of 2,4,5,6-tetraaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2-morpholino-4,5,6-triaminopyrimidine, 2,4-bis-dimethylamino-5,6-diaminopyrimidine, and the water-soluble acid addition salts of the above developers.
Claim 12
Dependent Claim
10 words
The preparation of claim 1 wherein the developer is p-toluenediamine.
Claim 13
Dependent Claim
34 words
The preparation of claim 1 wherein R 1 and R 2 are alkyl radicals of 1 to 4 carbon atoms and the developer is selected from the group consisting of p-toluenediamine, p-phenylene-diamine and p-aminophenol.
Claim 14
Dependent Claim
16 words
The preparation of claim 1 which contains 1% to 3% by weight of the developer-coupler combination.
Claim 15
Dependent Claim
41 words
A process for the dyeing of hair comprising applying to said hair, at temperatures ranging substantially from 15° C. to 40° C. for a time sufficient to effect dyeing through atmospheric oxidation, an effective amount of the preparation of claim 1.
Claim 16
Dependent Claim
24 words
The process for the dyeing of hair of claim 14 wherein the oxidation is also effected by the action of a chemical oxidizing agent.
Claim 17
Dependent Claim
78 words
A compound selected from the group consisting of (A) a 3,5-diamino-2-substituted alkyl benzene of the formula ##STR7## wherein R 1 is a straight- or branched-chain alkyl radical of 1 to 8 carbon atoms and R 2 is a member selected from the group consisting of phenyl and phenyl substituted by a member selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and halogen atoms and (B) a water-soluble acid addition salt of A.
Claim 18
Dependent Claim
78 words
A compound selected from the group consisting of (A) a 3,5-diamino-2-substituted alkyl benzene of the formula ##STR7## wherein R 1 is a straight- or branched-chain alkyl radical of 1 to 8 carbon atoms and R 2 is a member selected from the group consisting of phenyl and phenyl substituted by a member selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and halogen atoms and (B) a water-soluble acid addition salt of A.
Claim 19
Dependent Claim
23 words
The compound of claim 16 wherein R 1 is an alkyl radical of 1 to 4 carbon atoms and R 2 is phenyl.
Claim 20
Dependent Claim
44 words
The compound of claim 16 wherein R 1 is an alkyl radical of 1 to 4 carbon atoms and R 2 is phenyl substituted by a member selected from the group consisting of alkyl radicals of 1 to 4 carbon atoms and halogen atoms.
Claim 21
Dependent Claim
14 words
The compound of claim 16 which is the water-soluble acid addition salt of (A).
Claim 22
Dependent Claim
8 words
The compound of claim 16 which is 3,5-diamino-2-phenyloxytoluene.
References Cited (Backward Citations)
US1574337A
Cited
US2548574A
Cited
US3210252A
Cited
US3563684A
Cited
US3576876A
Cited
US3413073A
Cited
US4031160A
Cited
US3649160A
Cited
US3712790A
Cited
US3884627A
Cited
US4003699A
Cited
US4065255A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-10-15 | 1983-04-16 | 1983-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-10-15 | 1987-04-16 | 1987-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-10-15 | 1991-04-16 | 1991-10-16 | $7700.00 | Window Closed / Lapsed |