Novel 1,4-diamino-2-alkenylbenzene derivatives, and dyes containing these compounds

{
  "publication_number": "US2003121110A1",
  "country": "US",
  "kind": "A1",
  "title": "Novel 1,4-diamino-2-alkenylbenzene derivatives, and dyes containing these compounds",
  "abstract": "1,4-Diamino-2-alkenylbenzene derivatives of general formula (I) or physiologically tolerated water-soluble salts thereof as well as agents for oxidative dyeing of fibers, containing these compounds.",
  "claims": [
    "1. 1,4-Diamino-2-alkenylbenzene derivative of general formula (I) or a physiologically tolerated, water-soluble salt thereof wherein R1, R2, R3 and R4 independently of each other denote hydrogen, a C 1 -C 6 -alkyl group, C 2 -C 4 -hydroxyalkyl group, C 3 -C 4 -dihydroxyalkyl group or C 1 -C 4 -alkoxy-(C 1 -C 2)-alkyl group, or R1 and R2 or R3 and R4 form a four-membered to eight-membered ali-phatic ring, with at least two of the R1 to R4 groups denoting hydrogen; R5 denotes hydrogen, a halogen atom, a C 1 -C 4 -alkyl group, C 1 -C 4 -hydroxyalkyl group or C 1 -C 4 -alkoxy group; R6, R7 and R8 independently of each other denote hydrogen, a halogen atom, a cyano group, C 1 -C 4 -alkoxy group, C 1 -C 6 -alkyl group, - C(O)H group, - Si(CH 3) 3 group, C 1 -C 4 -hydroxyalkyl group, C 3 -C 4 -dihydroxyalkyl group, - CH 2 - Si(CH 3) 3 group or a group of formula (II) and R9 denotes hydrogen, an amino group, a halogen atom (F, Cl, Br, l), a nitro group or a hydroxyl group. 2. 1,4-Diamino-2-alkenylbenzene derivative according to claim 1, characterized in that in formula (I) one or more of groups R5 to R8 denote hydrogen. 3. 1,4-Diamino-2-alkenylbenzene derivative according to claim 1 or 2, characterized in that in formula (I) groups R1, R2, R3 and R4 denote hydrogen. 4. 1,4-Diamino-2-alkenylbenzene derivative according to one of claims 1 to 3, characterized in that in formula (I) one or more of groups R6, R7 and R8 denote a C 1 -C 4 -alkyl group or a C 1 -C 4 -hydroxyalkyl group. 5. 1,4-Diamino-2-alkenylbenzene derivative according to one of claims 1 to 4, characterized in that it is selected from among 1,4-diamino-2-styrylbenzene; 1,4-diamino-2-propenylbenzene; 1,4-diamino-2-(1-methylpropenyl)benzene; 1,4-diamino-2-(2-methylpropenyl)benzene; 1,4-diamino-2-(1,2-dimethylpropenyl)benzene; 1,4-diamino-2-propenylbenzene; 2-(2,5-diaminophenyl)-2-propen-1-ol; 3-(2,5-diaminophenyl)-2-propen-1-ol; and 3-(2,5-diaminophenyl)2-propen-1-ol [sic-Translator]. 6. Agent for oxidative dyeing of keratin fibers, based on a developer-coupler combination, characterized in that it contains as developer at least one 1,4-diamino-2-alkenylbenzene derivative of formula (I) according to one of claims 1 to 5. 7. Agent according to claim 6, characterized in that it contains the 1,4-diamino-2-alkenylbenzene derivative of formula (I) in an amount from 0.005 to 20.0 wt. %. 8. Agent according to claim 6 or 7, characterized in that the coupler is selected from among 2,6-diaminopyridine, 2-amino-4-[(2-hydroxyethyl)amino]anisole, 2,4-diamino-1-fluoro-5-methylbenzene, 2,4-diamino-1-methoxy-5-methylbenzene, 2,4-diamino-1-ethoxy-5-methylbenzene, 2,4-diamino-1-(2-hydroxyethoxy)-5-methylbenzene, 2,4-di[(2-hydroxyethyl)amino]-1,5-dimethoxybenzene, 2,3-diamino-6-methoxypyridine, 3-amino-6-methoxy-2-(methylamino)pyridine, 2,6-diamino-3,5-dimethoxypyridine, 3,5-diamino-2,6-dimethoxypyridine, 1,3-diaminobenzene, 2,4-diamino-1-(2-hydroxyethoxy)benzene, 2,4-diamino-1,5-di(2-hydroxyethoxy)benzene, 1-(2-aminoethoxy)-2,4-diaminobenzene, 2-amino-1-(2-hydroxyethoxy)-4-methylaminobenzene, 2,4-diaminophenoxyacetic acid, 3-[di(2-hydroxyethyl)amino]aniline, 4-amino-2-di[(2-hydroxyethyl)amino]-1-ethoxybenzene, 5-methyl-2-(1-methylethyl)phenol, 3-[(2-hydroxyethyl)amino]aniline, 3-[(2-aminoethyl)amino]aniline, 1,3-di(2,4-diaminophenoxy)propane, di(2,4-diaminophenoxy)methane, 1,3-diamino-2,4-dimethoxybenzene, 2,6-bis(2-hydroxyethyl)aminotoluene, 4-hydroxyindole, 3-dimethylaminophenol, 3-diethylaminophenol, 5-amino-2-methylphenol, 5-amino-4-fluoro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5-amino-4-ethoxy-2-methylphenol, 3-amino-2,4-dichlorophenol, 5-amino-2,4-dichlorophenol, 3-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 3-aminophenol, 2-[(3-hydroxyphenyl)amino]acetamide, 5-[(2-hydroxyethyl)amino]-2-methylphenol, 3-[(2-hydroxyethyl)amino]phenol, 3-[(2-meth-oxyethyl)amino]phenol, 5-amino-2-ethylphenol, 2-(4-amino-2-hydroxyphenoxy)ethanol, 5-[(3-hydroxypropyl)amino]-2-methylphenol, 3-[(2,3-dihydroxypropyl)amino]-2-methylphenol, 3-[(2-hydroxyethyl)amino]-2-methylphenol, 2-amino-3-hydroxypyridine, 5-amino-4-chloro-2-methylphenol, 1-naphthol, 1,5-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 2-methyl-1-naphthol acetate, 1,3-dihydroxybenzene, 1-chloro-2,4-dihydroxybenzene, 2-chloro-1,3-dihydroxybenzene, 1,2-dichloro-3,5-dihydroxy-4-methylbenzene, 1,5-dichloro-2,4-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 3,4-methylenedioxyphenol, 3,4-methylenedioxyaniline, 5-[(2-hydroxyethyl)amino]-1,3-benzodioxole, 6-bromo-1-hydroxy-3,4-methylenedioxybenzene, 3,4-diaminobenzoic acid, 3,4-dihydro-6-hydroxy-1,4(2H)benzoxazine, 6-amino-3,4-dihydro-1,4(2H)benzoxazine, 3-methyl-1-phenyl-5-pyrazolone, 5,6-dihydroxyindole, 5,6-dihydroxyindoline, 5-hydroxyindole, 6-hydroxyindole, 7-hydroxyindole and 2,3-indolinedione. 9. Agent according to one of claims 6 to 8, characterized in that besides the 1,4-diamino-2-alkenylbenzene derivative of formula (I) it contains at least one additional developer from the group consisting of 1,4-diaminobenzene, 2,5-diaminotoluene, 2-(2,5-diaminophenyl)ethyl alcohol, 4-aminophenol and its derivatives, 4,5-diaminopyrazole derivatives and tetraminopyrimidines. 10. Agent according to one of claims 6 to 9, characterized in that it contains a total amount of developers and couplers from 0.005 to 20 wt. %, based on the total amount of oxidation colorant 11. Agent according to one of claims 6 to 10, characterized in that it contains additionally at least one direct dye. 12. Agent according to one of claims 6 to 11, characterized in that it has a pH of 6.5 to 11.5. 13. Agent according to one of claims 6 to 12, characterized in that it is in the form of an aqueous or aqueous-alcoholic solution, a cream, a gel or an emulsion. 14. Agent according to one of claims 6 to 13, characterized in that it is a hair colorant."
  ],
  "cpc": [
    "A61Q 5/10",
    "A61K 8/411",
    "C07C 211/51"
  ],
  "filing_date": "2001-09-10",
  "publication_date": "2003-07-03",
  "priority_date": "2001-01-18",
  "application_number": "US-16989602-A",
  "family_id": "7670943",
  "citations": [
    "US5224965A",
    "US5292896A"
  ]
}