Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2000-01-07
2001-02-13
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S637000, C534S642000, C534S643000
Reexamination Certificate
active
06187912
ABSTRACT:
DESCRIPTION
Disazo compounds, their preparation and their use as dyestuffs
With respect to the dyeing quality of dyestuffs which have a fiber-reactive group, and the dyeings obtainable with them, customers are imposing ever higher requirements regarding fastness properties during processing and use. In the red sector in particular, dyestuffs are expected which not only have a high tinctorial strength but are also highly fast in depth of color and color shade in respect of the properties of their dyeings during use and processing.
The present invention now provides novel disazo compounds which correspond to the formula (1)
in which:
M is hydrogen or an alkali metal, such as lithium, sodium or potassium, and is preferably hydrogen or potassium and particularly preferably lithium or sodium;
R is hydrogen or sulfo bonded in the 2- or 3- or 4-position of the 6-sulfo-8-naphthol radical;
R
1
is hydrogen or alkyl having 1 to 6 carbon atoms, such as methyl, ethyl and propyl, which can be substituted, such as, for example, by sulfo, carboxy, hydroxy, halogen, such as chlorine, alkoxy having 1 to 4 carbon atoms, such as methoxy and ethoxy, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, alkanoylamino of 2 to 5 carbon atoms, such as acetylamino, or ureido, or is phenyl, which can be substituted, such as, for example, by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, hydroxy, halogen, such as chlorine, bromine and fluorine, alkoxy having 1 to 4 carbon atoms, such as methoxy and ethoxy, alkyl having 1 to 4 carbon atoms, such as methyl and ethyl, amino, sulfamoyl, carbamoyl, alkanoylamino having 2 to 5 carbon atoms, such as acetylamino, and ureido, and is preferably hydrogen, methyl or ethyl;
D
1
is phenyl or naphthyl, each optionally substituted by 1, 2 or 3 substituents chosen from the following group of substituents: fluorine, chlorine, cyano, alkyl having 1 to 4 carbon atoms, such as ethyl and, in particular, methyl, alkoxy having 1 to 4 carbon atoms, such as ethoxy and, in particular, methoxy, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, such as ethylamino and methylamino, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl, alkanoyl having 2 to 5 carbon atoms, such as acetyl and propionyl, alkanoylamino having 2 to 5 carbon atoms, such as acetylamino and propionylamino, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b) —CO—O—R
2
(a)
in which
R
2
is alkyl having 1 to 4 carbon atoms, such as methyl and ethyl, or is phenyl or phenyl which is substituted by substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy,
R
20
is hydrogen or alkyl having 1 to 4 carbon atoms, such as methyl and ethyl, which can be substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or alkoxy having 1 to 4 carbon atoms, such as methoxy and ethoxy, and
R
21
is alkyl having 1 to 4 carbon atoms, such as methyl and ethyl, which can be substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or phenyl, or is phenyl optionally substituted by 1 or 2 substituents selected from the group consisting of alkyl having 1 to 4 carbon atoms, such as ethyl and, in particular, methyl, alkoxy having 1 to 4 carbon atoms, such as ethoxy and, in particular, methoxy, chlorine, sulfo and carboxy;
D
2
is a phenylene or naphthylene, each optionally substituted by 1, 2 or 3 substituents chosen from the following group of substituents: fluorine, chlorine, cyano, alkyl having 1 to 4 carbon atoms, such as ethyl and, in particular, methyl, alkoxy having 1 to 4 carbon atoms, such as ethoxy and, in particular, methoxy, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, such as ethylamino and methylamino, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl, alkanoyl having 2 to 5 carbon atoms, such as acetyl and propionyl, alkanoylamino having 2 to 5 carbon atoms, such as acetylamino and propionylamino, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b) mentioned and defined above;
W is a group of the formula —SO
2
—Y or a group of the formula (2), (3), (4), (5) or (6)
in which
Y is vinyl or is ethyl which is substituted in the &bgr;-position by a substituent which is eliminated under the action of an alkaline reacting compound to form the vinyl group, such as, for example, by chlorine, sulfato, thiosulfato, phosphate and acetyloxy, and is preferably vinyl or &bgr;-sulfatoethyl;
R
3
is a group of the formula (c)
—A—SO
2
—Y (c)
in which
Y has one of the abovementioned meanings and
A is alkylene having 1 to 4 carbon atoms, such as n-ethylene and n-propylene, or alkylene having 3 to 6 carbon atoms which is interrupted by 1 or 2 hetero groups from the group consisting of —O—and —NH—, such as, for example, a group of the formula —CH
2
—CH
2
—O—CH
2
—CH
2
—, or is phenylene, which can be substituted by 1 or 2 substituents selected from the group consisting of alkoxy having 1 to 4 carbon atoms, such as ethoxy and, in particular, methoxy, alkyl having 1 to 4 carbon atoms, such as ethyl and, in particular, methyl, chlorine, sulfo and carboxy, or is naphthylene unsubstituted or substituted by 1 or 2 sulfo groups;
R
4
is hydrogen or alkyl having 1 to 4 carbon atoms, such as methyl and ethyl, which can be substituted by hydroxy, sulfato, phosphate, acetyloxy, propionyloxy, sulfo, carboxy or phenyl, or is phenyl, which can be substituted by 1 or 2 substituents selected from the group consisting of alkyl having 1 to 4 carbon atoms, such as ethyl and, in particular, methyl, alkoxy having 1 to 4 carbon atoms, such as ethoxy and, in particular, methoxy, chlorine, sulfo and carboxy, or is an abovementioned and defined group of the formula (c);
E
1
is hydrogen or fluorine, preferably fluorine;
E
2
is hydrogen, chlorine or fluorine, preferably hydrogen or chlorine;
R
5
is hydrogen or alkyl having 1 to 4 carbon atoms, such as ethyl or methyl;
R
6
is hydrogen, fluorine, chlorine, nitro, amino, hydroxy, sulfo, carboxy, alkyl having 1 to 4 carbon atoms, such as ethyl and, in particular, methyl, alkoxy having 1 to 4 carbon atoms, such as ethoxy and, in particular, methoxy, sulfamoyl, carbamoyl, alkanoylamino having 2 to 5 carbon atoms, such as acetylamino, or alkylamino having 1 to 4 carbon atoms, such as methylamino and ethylamino, and is preferably hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo and carboxy;
R
7
has one of the meanings of R
6
;
R
8
is hydrogen or alkyl having 1 to 4 carbon atoms, such as methyl and ethyl;
R
9
is hydrogen, alkyl having 1 to 4 carbon atoms, such as methyl and ethyl, or is phenyl or phenyl which is substituted by 1 or 2 substituents selected from the group consisting of chlorine, methyl, ethyl, methoxy, ethoxy, sulfo and carboxy, and is preferably hydrogen, methyl, ethyl, phenyl and sulfophenyl;
X
1
is fluorine, chlorine, hydroxy, amino, cyanoamino, alkoxy having 1 to 6 carbon atoms, such as methoxy and ethoxy, which can optionally be substituted, such as, for example, by methoxy or ethoxy, or is a group of the formula —NR
10
R
11
, in which R
10
is hydrogen or alkyl having 1 to 6 carbon atoms, such as methyl and ethyl, and R
11
has one of the meanings of R
10
or is phenyl, which can be substituted, such as, for example, by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, or the group —NR
10
R
11
is the radical of a 5- or 6-membered saturated heterocyclic ring, the alkylene radical of which can also be interrupted by a hetero group, such as, for example, by —O—or —NH—, such as, for example, morpholino and piperazino, and X
1
is preferably chlorine, fluorine or cyanoamino;
X
2
has one of the meanings of X
1
;
G is hydrogen or a group of the formula —SO
2
—Y, where Y has one of the abovementioned meanings, and where G is pref
Connolly Bove & Lodge & Hutz LLP
Dystar Textifarben GmbH & Co.
Powers Fiona T.
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