Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2002-04-05
2004-08-10
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S426000, C008S437000, C008S451000, C008S454000, C008S461000, C008S462000, C008S463000, C548S181000
Reexamination Certificate
active
06773463
ABSTRACT:
The object of the present invention is an agent for dyeing keratin fibers, for example silk, wool or hair, particularly human hair, and which contains a combination of (i) at least one 4-nitro-2,1,3-benzoxadiazole derivative, 4-nitro-2,1,3-benzothiadiazole derivative or 4-nitro-2,1,3-benzoselenadiazole derivative and (ii) at least one amine, aminonitrobenzene or phenol, and a method for dyeing keratin fibers by use of said dyeing agent.
Depending on the starting color of the hair to be dyed and the desired final result, hair colorants are divided mainly into oxidative colorants and toners. Oxidative hair colorants are very well suited for covering higher proportions of gray hair. The oxidative colorants used for a gray proportion of up to 50% are usually referred to as oxidative toners whereas the oxidative colorants used for hair with a proportion of gray hair greater than 50%, or for “brightening”, are usually referred to as oxidative colorants. Direct dyes are contained mainly in non-oxidative colorants (toners). Because of their small molecular size, some direct dyes, for example the nitro dyes, can penetrate into hair and—at least in the outer regions—dye it directly. Such toners are very gentle to the hair and as a rule can withstand six to eight hair washings. Direct dyes, particularly nitro dyes, are also frequently used in oxidative colorants to create certain shades or to intensify the color.
Nevertheless, there still exists a great need for colorants capable of both intense and gentle coloration under mild conditions.
Surprisingly, we have now found that by use of a combination of (i) at least one-4-nitro-2,1,3-benzoxadiazole derivative, 4-nitro-2,1,3-benzothiadiazole derivative or 4-nitro-2,1,3-benzoselenadiazole derivative and (ii) at least one amine, aminonitrobenzene or phenol, intense colorations with a great variety of shades can be achieved under mild conditions gentle to the hair.
Hence, the object of the present invention is an agent for dyeing fibers (A), for example wool, silk, cotton or hair and particularly human hair, which is prepared by mixing two components (A1) and (A2) and is characterized in that component (A1) contains at least one compound of formula (I)
wherein X denotes a halogen atom (F, Cl, Br, I), a methoxy group or an ethoxy group; Y denotes an oxygen atom, a sulfur atom or a selenium atom; R1 and R2 are equal or different and independently of each other denote hydrogen, a halogen atom (F, Cl, Br, I), a (C
1
-C
4
)-alkyl group, a (C
1
-C
4
)-alkyl group substituted with a halogen atom (F, Cl, Br, I), a (C
1
-C
4
)-alkoxy group, a nitro group, an acetamido group or an NR
a
R
b
group, wherein the R
a
and R
b
groups are equal or different and independently of each other denote hydrogen, a (C
1
-C
4
)-alkyl group, an optionally substituted aromatic carbon ring or a (C
1
-C
4
)-alkanecarbonyl group, or R
a
and R
b
together with the nitrogen atom form a heterocyclic (C
3
-C
6
) group (for example an imidazolidino, piperidino, pyrrolidino, pyrazolidino, piperazino or morpholino group); and component (A2) contains at least one compound selected from the group consisting of amines, aminonitrobenzenes and phenols.
Suitable compounds of formula (I) are, in particular, the following 4-nitro-2,1,3-benzoxadiazoles, 4-nitro-2,1,3-benzothiadiazoles and 4-nitro-2,1,3-benzoselenadiazoles:
4-chloro-7-nitro-2,1,3-benzoxadiazole; 4-bromo-7-nitro-2,1,3-benzoxadiazole; 4-fluoro-7-nitro-2,1,3-benzoxadiazole; 4-methoxy-7-nitro-2,1,3-benzoxediazole; 4-ethoxy-7-nitro-2,1,3-benzoxadiazole; 4-chloro-5,7-dinitro-2,1,3-benzoxadiazole; 5,7-dichloro-4-nitro-2,1,3-benzoxadiazole; 5,7-dibromo-4-nitro-2,1,3-benzoxadiazole; 7-chloro-4-nitro-5-diethylamino-2,1,3-benzoxadiazole; 5-amino-7-chloro-4-nitro-2,1,3-benzoxadiazole; 7-chloro-4-nitro-5-(1-piperidinyl)-2,1,3-benzoxadiazole; 4-chloro-7-nitro-2,1,3-benzothiadiazole; 4-bromo-7-nitro-2,1,3-benzothiadiazole; 4-methoxy-7-nitro-2,1,3-benzothiadiazole; 4-ethoxy-7-nitro-2,1,3-benzothiadiazole; 4-chloro-5,7-dinitro-2,1,3-benzothiadiazole; 4-bromo-5,7-dinitro-2,1,3-benzothiadiazole, 4,5-dichloro-7-nitro-2,1,3-benzothiadiazole; 5,7-dichloro-4-nitro-2,1,3-benzothiadiazole; 4,5-dibromo-7-nitro-2,1,3-benzothiadiazole; 5,7-dibromo-4-nitro-2,1,3-benzothiadiazole; 4,6-dichloro-5,7-dinitro-2,1,3-benzothiadiazole;4,6-dibromo-5,7-dinitro-2,1,3-benzothiadiazole; 5-chloro-7-fluoro-4-nitro-2,1,3-benzothiadiazole; 5-anilino-7-bromo-4-nitro-2,1,3-benzothiadiazole; 5-amino-7-chloro-4-nitro-2,1,3-benzothiadiazole; 7-bromo-5-(diethylamino)-4-nitro-2,1,3-benzothiadiazole; 4-chloro-5-methyl-7-nitro-2,1,3-benzothiadiazole;4-bromo-5-methyl-4-nitro-2,1,3-benzothiadiazole;7-bromo-5-(bromomethyl)-7-nitro-2,1,3-benzothiadiazole; N-(7-chloro-4-nitro-2,1,3-benzothiadiazole-5-yl)acetamide; 4-chloro-7-nitro-2,1,3-benzoselenadiazole; 4-bromo-7-nitro-2,1,3-benzoselenadiazole; 4-methoxy-7-nitro-2,1,3-benzoselenadiazole; 4-ethoxy-7-nitro-2,1,3-benzoselenadiazole; 5,7-dibromo-4-nitro-2,1,3-benzoselenadiazole; 5,7-dichloro-4-nitro-2,1,3-benzoselenadiazole; 7-bromo-5-methyl-4-nitro-2,1,3-benzoselenadiazole and 7-bromo-5-(bromomethyl)-4-nitro-2,1,3-benzoselenadiazole, among which the following compounds are particularly preferred: 4-chloro-7-nitro-2,1,3-benzoxadiazole; 4-bromo-7-nitro-2,1,3-benzoxadiazole; 4-chloro-7-nitro-2,1,3-benzothiadiazole; 4-bromo-7-nitro-2,1,3-benzothiadiazole; 4-chloro-7-nitro-2,1,3-benzoselenadiazole and 4-bromo-7-nitro-2,1,3-benzoselenadiazole.
Some of the compounds of formula (I) are commercially available. The compounds of formula (I), however, can also be prepared by methods of synthesis known from the literature, for example as described in the Journal of Organic Chemistry 36 (1), pages 207-209 (1971); Recueil Trav. Chim. Pays-Bas 86 (12), pages 1159-1181 (1967); Journal of Medicinal Chemistry, vol 17 (2), pages 203-206 (1974); Journal of the Chemical Society (B), 1967, pages 909-911 or in U.S. Pat. No. 3,577,427.
Suitable amines are aliphatic or aromatic (isocyclic or heterocyclic) compounds with at least one amino group. Suitable aminonitrobenzenes are aromatic (isocyclic or heterocyclic) compounds with at least one nitro group and at least one amino group, and suitable phenols are aromatic (isocyclic or heterocyclic) compounds with at least one hydroxyl group. Examples of the amines, aminonitrobenzenes and phenols contained in component (A2) are, in particular, the following:
ethanolamine; propylamine; 3-amino-1-propanol; butylamine; 4-amino-1-butanol; 1,4-diaminobenzene (p-phenylenediamine); 1,4-diamino-2-methylbenzene (p-toluylenediamine); 1,4-diamino-2,6-dimethylbenzene; 1,4-diamino-3,5-diethylbenzene; 1,4-diamino-2,5-dimethylbenzene; 1,4-diamino-2,3-dimethylbenzene; 2-chloro-1,4-diaminobenzene; 2,5-diaminobiphenyl; 1,4-diamino-2-hydroxymethylbenzene; 1,4-diamino-2-(2-hydroxyethoxy)benzene; 2-[2-(acetylamino)ethoxy]-1,4-diaminobenzene; N-methylaniline; 4-phenylaminoaniline; 4-dimethylaminoaniline; 4-diethylaminoaniline; 4-dipropylaminoaniline; 4-[ethyl(2-hydroxyethyl)amino]aniline; 4-[di(2′-hydroxyethyl)amino]aniline; 4-[di(2-hydroxyethyl)amino]-2-methylaniline; 4-[(2′-methoxyethyl)amino]aniline; 4-[(3′-hydroxypropyl)amino]aniline; 4-[(2,3-dihydroxypropyl)amino]aniline; 1,4-diamino-2-(2′-hydroxyethyl)benzene; 1,4-diamino-2-(1′-hydroxyethyl)benzene; 1,4-diamino-2-(1′-methylethyl)benzene; 1,4-diamino-2-(methoxymethyl)benzene; 1,4-diamino-2-(aminomethyl)benzene; 1,3-bis-[(4′-aminophenyl) (2′-hydroxyethyl)amino]-2-propanol; 1,4-bis-[(4-aminophenyl)amino]butane; 1,8-bis-(2′,5′-diaminophenoxy)-3,6-dioxaoctane; phenol; hydroquinone; 2-methylphenol; 3-methylphenol; 4-methylphenol; 5-methyl-2-(1′-methylethyl)phenol; 4-aminophenol; 4-amino-3-methylphenol; 4-amino-3-(hydroxymethyl)phenol; 4-amino-3-fluorophenol; 4-methylaminophenol; 4-amino-2-(aminomethyl)phenol; 4-amino-2-(hydroxymethyl)phenol; 4-amino-2-fluorophenol; 4-amino-[(2′-hydroxyethyl)amino]-methylphenol;
Braun Hans-Jürgen
Charrière Véronique
Pasquier Cecile
Elhilo Eisa
Gupta Yogendra N.
Striker Michael J.
Wella Aktiengesellschaft
LandOfFree
Agent and method for dyeing keratin fibers does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Agent and method for dyeing keratin fibers, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Agent and method for dyeing keratin fibers will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3331214