Disazo compound their preparation and their use as dyestuffs

A disazo compound corresponding to the formula (I)

• in which
• M is hydrogen or an alkali metal;
• R is hydrogen or sulfo bonded in the 2- or 3- or 4-position of the 6-sulfo-8-naphthol radical;
• R1 is hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted, or is phenyl, unsubstituted or substituted;
• D1 is phenyl or naphthyl, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b)
• —CO—O—R2 (a)
• in which
• R2 is alkyl having 1 to 4 carbon atoms, phenyl or phenyl which is substituted by substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy,
• R20 is hydrogen or alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or alkoxy having 1 to 4 carbon atoms, and
• R21 is alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, 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, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy;
• D2 is phenylene or naphthylene, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, 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 (4)
• in which
• E1 is hydrogen or fluorine,
• E2 is hydrogen, chlorine or fluorine and
• R5 is hydrogen or alkyl having 1 to 4 carbon atoms;
• the amino group —N(R1)— bonded to the acetoacetyl grouping is bonded to the 6-sulfo-8-naphthol radical in the 1-, 2- or 3-position.

A disazo compound corresponding to the formula (I)

• in which
• M is hydrogen or an alkali metal;
• R is hydrogen or sulfo bonded in the 2- or 3- or 4-position of the 6-sulfo-8-naphthol radical;
• R1 is hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted, or is phenyl, unsubstituted or substituted;
• D1 is phenyl or naphthyl, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b) —CO—O—R2 (a)
• in which
• R2 is alkyl having 1 to 4 carbon atoms, phenyl or phenyl which is substituted by substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy,
• R20 is hydrogen or alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or alkoxy having 1 to 4 carbon atoms, and
• R21 is alkyl having 1 to 4 carbon atoms optionally 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, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy;
• D2 is phenylene or naphthylene, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, 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 (5)
• in which:
• R5 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R6 is alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkanoylamino having 2 to 5 carbon atoms or alkylamino having 1 to 4 carbon atoms;
• R7 has one of the meanings of R6;
• R8 is hydrogen or alkyl having 1 to 4 carbon atoms;
• X1 is fluorine, chlorine, hydroxy, amino, cyanoamino, alkoxy having 1 to 6 carbon atoms, which can optionally be substituted, or is a group of the formula —NR10R11, in which R10 is hydrogen or alkyl having 1 to 6 carbon atoms and R11 has one of the meanings of R10 or is phenyl or substituted phenyl, or the group —NR10R11 is the radical of a 5- or 6-membered saturated heterocyclic ring, the alkylene radical of which optionally being interrupted by a hetero group;
• X2 has one of the meanings of X1;
• G is hydrogen or a group of the formula —SO2—Y, and where
• Y is vinyl or is ethyl which is substituted in the β position by a substituent which is eliminated under the action of an alkaline reacting compound to form the vinyl group:
• and the amino group —N(R1)— bonded to the acetoacetyl grouping is bonded to the 6-sulfo-8-naphthol radical in the 1-, 2- or 3-position.

A disazo compound corresponding to the formula (I)

• in which
• M is hydrogen or an alkali metal;
• R is hydrogen or sulfo bonded in the 2- or 3- or 4-position of the 6-sulfo-8-naphthol radical;
• R1 is hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted, or is phenyl, unsubstituted or substituted;
• D1 is phenyl or naphthyl, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b)
• —CO—O—R2 (a)
• in which
• R2 is alkyl having 1 to 4 carbon atoms, phenyl or phenyl which is substituted by substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy,
• R20 is hydrogen or alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, acetyloxy, propionyloxy, sulfo, carboxy or alkoxy having 1 to 4 carbon atoms, and
• R21 is alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, 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, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy;
• D2 is phenylene or naphthylene, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, 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 (6)
• in which
• Y is vinyl or is ethyl which is substituted in the β position by a substituent which is eliminated under the action of an alkaline reacting compound to form the vinyl group:
• A is alkylene having 1 to 4 carbon atoms 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—, or is phenylene unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is naphthylene optionally substituted by 1 or 2 sulfo groups;
• R5 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R9 is hydrogen, alkyl having 1 to 4 carbon atoms 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;
• X2 is fluorine, chlorine, hydroxy, amino, cyanoamino, alkoxy having 1 to 6 carbon atoms, which can optionally be substituted, or is a group of the formula —NR10R11, in which R10 is hydrogen or alkyl having 1 to 6 carbon atoms and R11 has one of the meanings of R10 or is phenyl or substituted phenyl, or the group —NR10R11 is the radical of a 5- or 6-membered saturated heterocyclic ring, the alkylene radical of which optionally being interrupted by a hetero group;
• and
• the amino group —N(R1)— bonded to the acetoacetyl grouping is bonded to the 6-sulfo-8-naphthol radical in the 1-, 2- or 3-position.

A disazo compound corresponding to the formula (I)

• in which
• M is hydrogen or an alkali metal;
• R is hydrogen or sulfo bonded in the 2- or 3- or 4-position of the 6-sulfo-8-naphthol radical;
• R1 is hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted, or is phenyl, unsubstituted or substituted;
• D1 is phenyl or naphthyl, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b)
• —CO—O R2 (a)
• in which
• R2 is alkyl having 1 to 4 carbon atoms, phenyl or phenyl which is substituted by substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy,
• R20 is hydrogen or alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, acetyloxy, propionyloxy, sulfo, carboxy or alkoxy having 1 to 4 carbon atoms, and
• R21 is alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, 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, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy;
• D2 is phenylene unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is naphthylene which is substituted by 1 or 2 sulfo groups;
• W is a group of the formula —SO2—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 β position by a substituent which is eliminated under the action of an alkaline reacting compound to form the vinyl group:
• R3 is a group of the formula (c)
• —A—SO2—Y (c)
• in which
• Y has one of the abovementioned meanings and
• A is alkylene having 1 to 4 carbon atoms 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—, or is phenylene unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is naphthylene optionally substituted by 1 or 2 sulfo groups;
• R4 is hydrogen or alkyl having 1 to 4 carbon atoms unsubstituted or substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or phenyl, or is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is an abovementioned and defined group of the formula (c);
• E1 is hydrogen or fluorine;
• E2 is hydrogen, chlorine or fluorine;
• R5 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R6 is alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkanoylamino having 2 to 5 carbon atoms or alkylamino having 1 to 4 carbon atoms;
• R7 has one of the meanings of R6;
• R8 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R9 is hydrogen, alkyl having 1 to 4 carbon atoms 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;
• X1 is fluorine, chlorine, hydroxy, amino, cyanoamino, alkoxy having 1 to 6 carbon atoms, which can optionally be substituted, or is a group of the formula —NR10R11, in which R10 is hydrogen or alkyl having 1 to 6 carbon atoms and R11 has one of the meanings of R10 or is phenyl or substituted phenyl, or the group —NR10R11 is the radical of a 5- or 6-membered saturated heterocyclic ring, the alkylene radical of which optionally being interrupted by a hetero group;
• X2 has one of the meanings of X1;
• G is hydrogen or a group of the formula —SO2—Y, where Y has one of the abovementioned meanings;
• the amino group —N(R1)— bonded to the acetoacetyl grouping is bonded to the 6-sulfo-8-naphthol radical in the 1-, 2- or 3-position.

A process for the preparation of a compound of the formula (I)

• in which
• M is hydrogen or an alkali metal;
• R is hydrogen or sulfo bonded in the 2- or 3- or 4-position of the 6-sulfo-8-naphthol radical;
• R1 is hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted, or is phenyl, unsubstituted or substituted;
• D1 is phenyl or naphthyl, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b)
• —CO—O—R2 (a)
• in which
• R2 is alkyl having 1 to 4 carbon atoms, phenyl or phenyl which is substituted by substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy,
• R20 is hydrogen or alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, acetyloxy, propionyloxy, sulfo, carboxy or alkoxy having 1 to 4 carbon atoms, and
• R21 is alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, 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, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy;
• D2 is phenylene or naphthylene, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, 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 —SO2—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 β position by a substituent which is eliminated under the action of an alkaline reacting compound to form the vinyl group:
• R3 is a group of the formula (c)
• —A—SO2—Y (c)
• in which
• Y has one of the abovementioned meanings and
• A is alkylene having 1 to 4 carbon atoms 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—, or is phenylene unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is naphthylene optionally substituted by 1 or 2 sulfo groups;
• R4 is hydrogen or alkyl having 1 to 4 carbon atoms unsubstituted or substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or phenyl, or is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is an abovementioned and defined group of the formula (c);
• E1 is hydrogen or fluorine;
• E2 is hydrogen, chlorine or fluorine;
• R5 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R6 is alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkanoylamino having 2 to 5 carbon atoms or alkylamino having 1 to 4 carbon atoms;
• R7 has one of the meanings of R6;
• R8 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R9 is hydrogen, alkyl having 1 to 4 carbon atoms 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;
• X1 is fluorine, chlorine, hydroxy, amino, cyanoamino, alkoxy having 1 to 6 carbon atoms, which can optionally be substituted, or is a group of the formula —NR10R11, in which R10 is hydrogen or alkyl having 1 to 6 carbon atoms and R11 has one of the meanings of R10 or is phenyl or substituted phenyl, or the group —NR10R11 is the radical of a 5- or 6-membered saturated heterocyclic ring, the alkylene radical of which optionally being interrupted by a hetero group;
• X2 has one of the meanings of X1;
• G is hydrogen or a group of the formula —SO2—Y, where Y has one of the abovementioned meanings;
• the amino group —N(R1)— bonded to the acetoacetyl grouping is bonded to the 6-sulfo-8-naphthol radical in the 1-, 2- or 3-position which comprises coupling a diazonium salt compound of an amine of the formula D1—NH2 in which D1 is defined above, with a compound of the formula (7)
• in which M, R and R1 are defined above, R is bonded in the 2-, 3- or 4-position of the 6-sulfo-8-naphthol radical and the amino group —N(R1)H is bonded to the 6-sulfo-8-naphthol radical in the 1-, 2- or 3-position, reacting the azo compound thus prepared with diketene at a temperature of 20 to 70° C. and a pH of 4 to 11 to give the compound of the formula (8)
• in which the individual members of the formula have the meanings defined above, and then coupling it with a diazonium salt compound of an amine of the formula H2N—D2—W where D2 and W have the abovementioned meaning, to give the compound of the formula (1), or reacting a compound of the formula (7) with diketene at a temperature of 20 to 60° C. and a pH of 4 to 11 and coupling the acetoacetylamino-mono- or -disulfo-naphthol compound obtained with the diazonium salt of an amine of the formula D1—NH2, where D1 has the meaning given above, and with a second diazonium salt of an amine of the formula H2N—D2—W, where D2 and W have the meaning given above, at a pH of between 4 and 7 and at a temperature between 5 and 20° C.

A process for dyeing fibers which comprises applying a dyestuff comprising the disazo compound

• in which
• M is hydrogen or an alkali metal;
• R is hydrogen or sulfo bonded in the 2- or 3- or 4-position of the 6-sulfo-8-naphthol radical;
• R1 is hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted, or is phenyl, unsubstituted or substituted;
• D1 is phenyl or naphthyl, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, benzoyl, benzoylamino, sulfobenzoylamino, methylbenzoylamino, a group of the formula (a) and a group of the formula (b) —CO—O—R2 (a)
• in which
• R2 is alkyl having 1 to 4 carbon atoms, phenyl or phenyl which is substituted by substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy,
• R20 is hydrogen or alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or alkoxy having 1 to 4 carbon atoms, and
• R21 is alkyl having 1 to 4 carbon atoms optionally substituted by hydroxy, sulfato, phosphate, 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, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy;
• D2 is phenylene or naphthylene, each optionally substituted by 1, 2 or 3 substituents selected from the group consisting of:
• fluorine, chlorine, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, amino, hydroxy, alkylamino having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkylsulfonyl having 1 to 4 carbon atoms, alkanoyl having 2 to 5 carbon atoms, alkanoylamino having 2 to 5 carbon atoms, 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 —SO2—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 β position by a substituent which is eliminated under the action of an alkaline reacting compound to form the vinyl group:
• R3 is a group of the formula (c)
• —A—SO2—Y (c)
• in which
• Y has one of the abovementioned meanings and
• A is alkylene having 1 to 4 carbon atoms 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—, or is phenylene unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is naphthylene optionally substituted by 1 or 2 sulfo groups;
• R4 is hydrogen or alkyl having 1 to 4 carbon atoms unsubstituted or substituted by hydroxy, sulfato, phosphato, acetyloxy, propionyloxy, sulfo, carboxy or phenyl, or is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, chlorine, sulfo and carboxy, or is an abovementioned and defined group of the formula (c);
• E1 is hydrogen or fluorine;
• E2 is hydrogen, chlorine or fluorine;
• R5 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R6 is alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfamoyl, carbamoyl, alkanoylamino having 2 to 5 carbon atoms or alkylamino having 1 to 4 carbon atoms;
• R7 has one of the meanings of R6;
• R8 is hydrogen or alkyl having 1 to 4 carbon atoms;
• R9 is hydrogen, alkyl having 1 to 4 carbon atoms 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;
• X1 is fluorine, chlorine, hydroxy, amino, cyanoamino, alkoxy having 1 to 6 carbon atoms, which can optionally be substituted, or is a group of the formula —NR10R11, in which R10 is hydrogen or alkyl having 1 to 6 carbon atoms and R11 has one of the meanings of R10 or is phenyl or substituted phenyl, or the group —NR10R11 is the radical of a 5- or 6-membered saturated heterocyclic ring, the alkylene radical of which optionally being interrupted by a hetero group;
• X2 has one of the meanings of X1;
• G is hydrogen or a group of the formula —SO2—Y, where Y has one of the abovementioned meanings;
• the amino group —N(R1)—bonded to the acetoacetyl grouping is bonded to the 6-sulfo-8-naphthol radical in the 1-, 2- or 3-position, to a fiber material and the dyestuff is fixed on the material by means of
• (A) heat,
• (B) by means of an alkaline agent or
• (C) by means of heat and an alkaline agent.