Use of 4-nitro-2,1,3,-benzoxadiazole derivatives as dyes in...

Details Use of 4-nitro-2,1,3,-benzoxadiazole derivatives as dyes in... Use of 4-nitro-2,1,3,-benzoxadiazole derivatives as dyes in...

2002-03-26

2004-06-15

Mruk, Brian P. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S437000, C008S451000, C008S455000, C008S462000, C548S181000

Reexamination Certificate

active

06749645

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to colorants for keratin fibers, particularly human hair, containing 4-nitro-2,1,3-benzoxadiazole derivatives as dye.
As a rule, the color-changing treatment of keratin-containing fibers, for example human hair, wool or furs, is carried out by use of two dyeing methods. By the first method, the color is produced with oxidative or permanent colorants by use of a mixture of different developers and couplers and an oxidant. If necessary, to finish the coloring or to create special color effects, direct dyes may be added. The second method makes exclusive use of direct dyes which are applied to the fibers in a suitable carrier composition. This method is simple to use, quite mild and causes only minor damage to the keratin fibers. The direct dyes used for this purpose must meet numerous requirements. They must be toxicologically and dermatologically innocuous and must make it possible to achieve colorations of the desired intensity, which also assumes adequate water solubility, among other things. Moreover, the resulting colorations must be resistant to light, acids and rubbing.
The direct dyes for keratin fibers usually consist of a combination of different nonoxidative dyes. Because the choice of red and blue dyes that can be used in colorants for keratin fibers is limited, a need for such dyes continues to exist.
SUMMARY OF THE INVENTION
The object of the present invention is the use of 4-nitro-2,1,3-benzoxadiazole derivatives of general formula (I) as dye in colorants for keratin fibers, for example wool, silk, furs or hair, particularly human hair,
wherein
X denotes oxygen, sulfur or NR
a
, R
a
standing for hydrogen, a (C
1
-C
4
)-alkyl group, a monohydroxy-(C
1
-C
4
)-alkyl group, a polyhydroxy-(C
2
-C
4
)-alkyl group or a mono-(C
1
C
4
)-alkoxy-(C
1
-C
4
)-alkyl group,
R1 and R2 can be 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 halogen-substituted (C
1
-C
4
)-alkyl group, a (C
1
-C
4
)-alkoxy group, a nitro group or an NR
b
R
c
group, the R
b
and R
c
groups being equal or different and independently of each other denoting hydrogen, a (C
1
-C
4
)-alkyl group, an optionally substituted aromatic carbon ring or a (C
1
-C
4
)-alkanecarbonyl group, or R
b
and R
c
together with the nitrogen atom forming a heterocyclic (C
3
-C
6
) group (for example, an imidazolidino, piperidino, pyrrolidino, pyrazolidino, piperazino or morpholino group);
Q denotes hydrogen, an aliphatic group, an aromatic isocyclic group or an aromatic heterocyclic group, preferably an aromatic monocyclic to tetracyclic group, particularly an aromatic monocyclic or bicyclic group.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred compounds of formula (I) are those wherein Q has the following meaning: methyl, ethyl, phenyl, biphenyl, C
6
H
4
R3, C
6
H
3
R3R4 or C
6
H
2
R3R4R5 wherein R3, R4 and R5 are equal or different and independently of each other stand for F, Cl, Br, I, CN, NO
2
, CF
3
, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, monohydroxy-(C
1
-C
4
)-alkyl polyhydroxy-(C
2
-C
4
)-alkyl, mono-(C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio, hydroxy NR
d
R
e
, CHO, COR
f
, COOH, COOR
g
, CONHR
h
or NHCOR
i
, wherein R
d
and R
e
independently of each other denote hydrogen, a (C
1
-C
4
)-alkyl group, a monohydroxy-C
1
-C
4
-alkyl group, a polyhydroxy-(C
2
-C
4
)-alkyl group or an optionally substituted aromatic carbon ring, and R
f
, R
g
, R
h
and R
i
independently of each other denote a (C
1
-C
4
)-alkyl group or an optionally substituted aromatic carbon ring.
Particularly preferred among the abovesaid compounds of formula (I) are those wherein: X stands for oxygen or NR
a
, with R
a
denoting hydrogen, a (C
1
-C
4
)-alkyl group, a monohydroxy-(C
1
-C
4
)-alkyl group, a polyhydroxy-(C
2
-C
4
)-alkyl group or a mono-(C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl group;
R1=R2=hydrogen; Q stands for methyl, ethyl, phenyl, biphenyl, C
6
H
4
R3, C
6
H
3
R3R4 or C
6
H
2
R3R4R5, wherein R3, R4 and R5 are equal or different and independently of each other stand for F, Cl, Br, I, CN, NO
2
, CF
3
, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, monohydroxy-(C
1
-C
4
)-alkyl, polyhydroxy-(C
2
-C
4
)-alkyl, mono-(C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio, hydroxy, NR
d
R
e
, CHO, COR
f
, COOH, COOR
g
, CONHR
h
or NHCOR
l
wherein R
d
and R
e
independently of each other denote hydrogen, a (C
1
-C
4
)-alkyl group, a monohydroxy-(C
1
-C
4
)-alkyl group, a polyhydroxy-(C
2
-C
4
)-alkyl group or an optionally substituted aromatic carbon ring, and R
f
, R
g
, R
h
and R
i
independently of each other denote a (C
1
-C
4
)-alkyl group or an optionally substituted aromatic carbon ring.
Suitable 4-nitro-2,1,3-benzoxadiazole derivatives of formula (I) are, for example: 4-amino-7-nitro-2,1,3-benzoxadiazole; 4-N,N-dimethylamino-7-nitro-2,1,3-benzoxadiazole; 4-nitro-7-methoxy-2,1,3-benzoxadiazole; 4-nitro-7-ethoxy-2,1,3-benzoxadiazole; 4-nitro-7-phenoxy-2,1,3-benzoxadiazole; 4-nitro-7-(4′-nitrophenoxy)-2,1,3-benzoxadiazole; 4-nitro-7-(2′,4′,6′-trimethylphenoxy)-2,1,3-benzoxadiazole; 7-nitro-4-(N-phenylamino)-2,1,3-benzoxadiazole; 4-[N-1-(naphthalenyl)amino]-7-nitro-2,1,3-benzoxadiazole; 4-[N-(4′-chlorophenyl)amino]-7-nitro-2,1,3-benzoxadiazole; 4-[N-(4′-fluorophenyl)amino]-7-nitro-2,1,3-benzoxadiazole; 7-nitro-4-[N-(4′-nitrophenyl)amino]-2,1,3-benzoxadiazole; 7-nitro-4-[N-(3′-nitrophenyl)amino]-2,1,3-benzoxadiazole; 4-[N-(2′,4′-dinitrophenyl)amino]-7-nitro-2,1,3-benzoxadiazole; 4-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]benzonitrile; 4-[N-(4′-methylphenyl)amino]-7-nitro-2,1,3-benzoxadiazole; 4-[N-(2′-methylphenyl)amino]-7-nitro-2,1,3-benzoxadiazole; 4-[N-(4′-methoxyphenyl)amino]-7-nitro-2,1,3-benzoxadiazole; 4-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]phenol; 4-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-3-chloro-5-nitrophenol; 3-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]phenol; 2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]phenol; N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-1,4-diaminobenzene; N,N-dimethyl-N′-(7-nitro-2,1,3-benzoxadiazol-4-yl)-1,4-diaminobenzene; N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-2-(2′-hydroxyethyl)-1,4-diaminobenzene; N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-2-(1′-hydroxyethyl)-1,4-diaminobenzene; N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-2-methoxymethyl-1,4-diaminobenzene; N,N-di-(2′-hydroxyethyl)-N′-(7-nitro-2,1,3-benzoxadiazol-4-yl)-2-nitro-1,4-diaminobenzene; methyl 4-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]benzoate; 4-nitro-7-(phenylthio)-2,1,3-benzoxadiazole; 4-[(4′-chlorophenyl)thio]-7-nitro-2,1,3-benzoxadiazole; 4-[(3′-chlorophenyl)thio]-7-nitro-2,1,3-benzoxadiazole; 4-[(4′-bromophenyl)thio]-7-nitro-2,1,3-benzoxadiazole; 4-[(4′-methylphenyl)thio]-7-nitro-2,1,3-benzoxadiazole; 4-[(3′-methoxyphenyl)thio]-7-nitro-2,1,3-benzoxadiazole; 4-nitro-7-[(4′-nitrophenyl)thio]-2,1,3-benzoxadiazole; 2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)thio]benzoic acid; 5,7-dinitro-N-phenyl-4-amino-2,1,3-benzoxadiazole; 4-{N-[(1,1′-biphenyl)-4-yl]amino}-5,7-dinitro-2,1,3-benzoxadiazole; 4-[N-(4′-chlorophenyl)amino]-5,7-dinitro-2,1,3-benzoxadiazole; 4-[N-(4′-bromophenyl)amino]-5,7-dinitro-2,1,3-benzoxadiazole; 4-[N-(3′-bromophenyl)amino]-5,7-dinitro-2,1,3-benzoxadiazole; 5,7-dinitro-4-[N-(4′-nitrophenyl)amino]-2,1,3-benzoxadiazole; 5,7-dinitro-4-[N-(3′-nitrophenyl)amino]-2,1,3-benzoxadiazole; 4-[N-(4′-methoxyphenyl)amino]-5,7-dinitro-2,1,3-benzoxadiazole; 4-[N-(4′-methylphenyl)amino]-5,7-dinitro-2,1,3-benzoxadiazole; N′-(5,7-dinitro-2,1,3-benzoxadiazol-4-yl)-N,N-dimethyl-1,4-diamin

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