Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2002-11-12
2004-04-27
Lambkin, Deborah C. (Department: 1626)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S408000, C008S415000, C008S421000, C548S125000
Reexamination Certificate
active
06726730
ABSTRACT:
BACKGROUND OF THE INVENTION
The object of the present invention are new 7-nitro-2,1,3-benzoxadiazole or 7-nitro-2,1,3-benzthiadiazole derivatives and dyeing agents for keratin fibers, especially human hair, containing these compounds.
For the color-changing treatment of keratin-containing fibers, such as human hair, wool or fur, two dyeing methods are generally employed. In the first method, the dyeing is produced with so-called oxidative or permanent dyeing agents using a mixture of different developer and coupler substances and an oxidizing agent. If necessary, so-called substantive (non-oxidative) dyes may be added to round off the dyeing result or to produce special color effects. The second method makes use exclusively of substantive dyes, which are applied on the fibers in a suitable carrier composition. This method is easily employed, very mild and distinguished by little damage to the keratin fibers. The substantive dyes, used here, must satisfy a plurality of requirements. They must be safe from toxicological and dermatological points of view and make it possible to achieve dyeings of the desired intensity. Among other things, this also presupposes an adequate solubility in water. In addition, the dyeings achieved are expected to have a good light fastness, acid fastness, crocking resistance and good stability when washed.
As a rule, a combination of different, non-oxidative dyeing agents are required for substantive (non-oxidative) dyes for keratin fibers. Since the selection of red and blue dyes, which can be used in dyeing agents for keratin fibers, is limited, there continues to be a need for such dyes.
SUMMARY OF THE INVENTION
The object of the present invention therefore are new 7-nitro-2,1,3-benzoxadiazole oxadiazole compounds and 7-nitro-2,1,3-benzthiadiazole compounds of formula (I)
wherein X is oxygen or sulfur;
Y1 and Y2 are the same or different and, independently of one another, each represent a nitrogen atom or a nitrogen monoxide group;
R1 and R2 are the same or different and, independently of one another, each represent hydrogen, a halogen atom (F, Cl, Br, I), a (C
1
-C
4
)-alkyl group, a substituted (C
1
-C
4
)-alkyl group substituted with a halogen atom, a (C
1
-C
4
-alkoxy group, a nitro group or an NR
a
R
b
group, the R
a
and R
b
are the same or different and, independently of one another, each represent hydrogen, a (C
1
-C
4
-alkyl group, an optionally substituted, aromatic carbocyclic group or a (C
1
-C
4
)-alkane carbonyl group, or
R
a
and R
b
, together with the nitrogen atom, form a heterocyclic (C
3
-C
6
)-group;
V represents hydrogen, an aliphatic group, an aromatic isocyclic group, an aromatic heterocyclic group, a cyano group or a carbonyl function (CO)—R3, wherein R3 represents hydrogen, a hydroxy group, a (C
1
-C
4
-alkoxy group, an amino group, a (C
1
-C
4
)-alkylamino group, a (C
1
-C
6
)-alkyl group or an aryl group;
W represents a cyano group or a carbonyl function (CO)—R4, R4 representing hydrogen, a hydroxy group, a (C
1
-C
4
)-alkoxy group, an amino group, a (C
1
-C
4
-alkylamino group, a (C
1
-C
6
)-alkyl group or an aryl group; alternatively, V and W together form an aliphatic or aromatic isocyclic or heterocyclic ring system; and
Kat
+
represents an alkali cation, an alkaline earth cation, a quaternary ammonium group, a quaternary phosphonium group or a sulfonium group.
All other tautomeric forms of the general Formula (I) are also included.
Preferred are compounds of Formula (I), in which
X is oxygen or sulfur,
Y1 and Y2 may be the same or different and, independently of one another, represent nitrogen or a nitrogen monoxide group (NO),
R1 and R2 may be the same or different and, independently of one another, represent hydrogen, a halogen atom (F, Cl, Br, I), a (C1-C4) alkyl group or a nitro group,
V is hydrogen, an aliphatic group, an aromatic isocyclic group, an aromatic heterocyclic group, a cyano group or a carbonyl function (CO)—R3, R3 being hydrogen, a hydroxy group, a (C
1
-C
4
) alkoxy group, an amino group, a (C
1
-C
4
) alkylamino group, a (C
1
-C
6
) alkyl group or an aryl group,
W represents a cyano group or a carbonyl function (CO)—R4, R4 being hydrogen, a hydroxy group, a (C
1
-C
4
) alkoxy group, an amino group, a (C
1
-C
4
) alkylamino group, a (C
1
-C
6
) alkyl group or an aryl group; alternatively, V and W may also jointly form an aliphatic or aromatic isocyclic or heterocyclic ring system and
Kat
+
corresponds to an alkali cation, an alkaline earth cation, a quaternary ammonium group, a quaternary phosphonium group or a sulfonium group.
Especially preferred 7-nitro-2,1,3-benzoxadiazole derivatives of Formula (I) are the sodium salt of 4-(dicyanomethyl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(1-cyano-2-ethoxy-2-oxoethyl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(dicyanomethyl)-7-nitro-2,1,3-benzoxadiazole-N-oxide, the sodium salt of 4-(dihydro-2,4,6(1H,5H)-pyrimidine-trione-5-yl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(1-cyano-3,3-dimethyl-2-oxobutyl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(bis(methoxycarbonyl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(4,5-dihydro-3-methyl-1-phenyl-1H-pyrazole-5-one-4-yl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(cyano-(4-nitrophenyl)-methyl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-((aminocarbonyl)-cyano-methyl)-7-nitro-2,1,3-benzoxadiazole-1 -oxide, the sodium salt of 4-(1-cyano-2-ethoxy-2-oxoethyl)-7-nitro-2,1,3-benzoxadiazole-1 -oxide, the sodium salt of 4-(1,3-cyclohexane-dione-2-yl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(carboxy-cyanomethyl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(2-ethoxy-1-nitro-2-oxoethyl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-((aminocarbonyl)cyanomethyl)-7-nitro-2,1,3-benzoxadiazole,the sodium salt of 4-(dihydro-2-thioxo-4,6(1H,5H)-pyrimidine-dione-5-yl)-7-nitro-2,1,3-benzoxadiazole-1-oxide, the sodium salt of 4-(1,3-dioxo-indan-2-yl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(2-oxo-2,3-dihydro-1H-indole-3-yl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(4-oxo-2-thioxo-thiazolidine-5-yl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(dihydro-6-thioxo-2,4-(1H, 5H)-pyrimidine-dione-3-yl)-7-nitro-2,1,3-benzoxadiazole, the sodium salt of 4-(1-cyano-2-oxo-2-phenylethyl)-2,1,3-benzoxadiazole and the sodium salt of 4-(cyano-(2-nitrophenyl)-methyl)-7-nitro-2,1,3-benzoxadiazole.
Especially preferred 7-nitro-2,1,3-benzthiadiazole derivative of Formula (I) are the sodium salt of 4-(dicyanomethyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(1-cyano-2-ethoxy-2-oxoethyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(cyano-(4-nitrophenyl)-methyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(dicyanomethyl)-7-nitro-2,1,3-benzthiadiazole-N-oxide, the sodium salt of 4-(dihydro-2,4,6(1H,5H)-pyrimidine-trione-5-yl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(1-cyano-3,3-dimethyl-2-oxobutyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(bis(methoxycarbonyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(4,5-dihydro-3-methyl-1-phenyl-1H-pyrazole-5-one-4-yl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(1,3-cyclohexane-dione-2-yl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(carboxy-cyanomethyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(2-ethoxy-1-nitro-2-oxoethyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-((aminocarbonyl)cyanomethyl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(dihydro-2-thioxo-4,6(1H,5H)-pyrimidine-dione-5-yl)-7-nitro-2,1,3-benzthiadiazole-1-oxide, the sodium salt of 4-(1,3-dioxo-indan-2-yl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(2-oxo-2,3-dihydro-1H-indole-3-yl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(4-oxo-2-thioxo-thiazolidine-5-yl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(dihydro-6-thioxo-2,4-(1H,5H)-pyrimidine-dione-3-yl)-7-nitro-2,1,3-benzthiadiazole, the sodium salt of 4-(1-cyano-2-oxo-2-phenylethyl)-2,1,3-benzthiadiazole and the sodium salt of 4-(cyano-(2-nitrophenyl)-m
Braun Hans-Juergen
Mueller Catherine
Oberson Sylviane
Umbricht Gisela
Lambkin Deborah C.
Shiao Robert
Wella Aktiengesellschaft
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