Fiber-reactive azo dyes and dye mixtures, preparation thereof and use thereof

Abstract

The present invention relates to azo dyes of the formula (1), in which R, M, and Y are defined as stated in claim 1, to dye mixtures comprising them, to processes for preparing them, and to their use.

Description

(1) Technical field

[0001] The invention relates to the technical field of fiber reactive azo dyes. (2) Background technology

[0002] Within the textile industry, there is a need for orange reactive dyes with very good buildup and very good fastnesses, which are required especially when dyeing in mixtures with other dyes.

[0003] The dyes disclosed in EP 0 785 237 A1 and KR 20020038989 do not yet meet this requirement. There is therefore a further need for such dyes. (3) Contents of the invention

[0004] The present invention succeeds in providing a dye which highly satisfies the requirements for lifting power, wash-off ability and fastness.

[0005] The present invention provides azo dyes having formula (1)

[0006]

[0007] In formula (1)

[0008] Y is -CH=CH 2 or -CH 2 CH 2 Z, where

[0009] Z is a base-separable group;

[0010] R is a group -COOR 1 , -CN or -CONR 2 R 3 ,in

[0011] R 1 for M or (C 1 -C 4 )-alkyl;

[0012] R 2 and R 3 each indep...

Examples

Embodiment 1

[0125] a) 13.7 parts of 3-aminobenzoic acid are introduced into 100 parts of water. 20 parts of concentrated hydrochloric acid and 100 parts of ice were added, and a solution obtained by dissolving 7 parts of sodium nitrite in 20 parts of water was added dropwise over 30 minutes. This was followed by stirring at 0-5°C for 1 hour. Excess nitrite is decomposed with sulfamic acid.

[0126] b) 56 parts of 2,4-diamino-5-[2-sulfo-4-(2-sulfoxyethylsulfonyl)phenylazo]benzenesulfonic acid dissolved in 300 parts of water at pH 6-7 , the diazo compound prepared in step a) is added dropwise, and the pH is maintained between 6-7 with 20% strength sodium carbonate solution. The temperature is 20-25°C, and the stirring is continued until the reaction is completed. The finally obtained reaction mixture was dried under reduced pressure.

[0127] The obtained dye (λ max =430nm) accord with formula (1a)

[0128]

[0129] And dyes the cotton an orange hue.

Embodiment 2

[0131] The 3-aminobenzoic acid in embodiment 1 is replaced with 13.6 parts of 3-amino-benzamide, adopts the reaction process identical with embodiment 1, makes the dyestuff (λ with formula (1b) max =427nm).

[0132]

[0133] (λ max =427nm).

Embodiment 3

[0135] The 3-aminobenzoic acid in embodiment 1 is replaced by 3-aminobenzonitrile, adopts the reaction process identical with embodiment 1, obtains the dyestuff (λ with formula (1c) max =421nm).

[0136]

[0137] (λ max =421nm).

[0138] Examples 4 to 15, preparation of compounds of general formula (1d), wherein D is as defined in the table, can be prepared by the same steps as in Example 1.

[0139]

[0140]

[0141]

(1) Technical field

[0001] The invention relates to the technical field of fiber reactive azo dyes. (2) Background technology

[0002] Within the textile industry, there is a need for orange reactive dyes with very good buildup and very good fastnesses, which are required especially when dyeing in mixtures with other dyes.

[0003] The dyes disclosed in EP 0 785 237 A1 and KR 20020038989 do not yet meet this requirement. There is therefore a further need for such dyes. (3) Contents of the invention

[0004] The present invention succeeds in providing a dye which highly satisfies the requirements for lifting power, wash-off ability and fastness.

[0005] The present invention provides azo dyes having formula (1)

[0006]

[0007] In formula (1)

[0008] Y is -CH=CH 2 or -CH 2 CH 2 Z, where

[0009] Z is a base-separable group;

[0010] R is a group -COOR 1 , -CN or -CONR 2 R 3 ,in

[0011] R 1 for M or (C 1 -C 4 )-alkyl;

[0012] R 2 and R 3 each indep...

Examples

Embodiment 1

[0125] a) 13.7 parts of 3-aminobenzoic acid are introduced into 100 parts of water. 20 parts of concentrated hydrochloric acid and 100 parts of ice were added, and a solution obtained by dissolving 7 parts of sodium nitrite in 20 parts of water was added dropwise over 30 minutes. This was followed by stirring at 0-5°C for 1 hour. Excess nitrite is decomposed with sulfamic acid.

[0126] b) 56 parts of 2,4-diamino-5-[2-sulfo-4-(2-sulfoxyethylsulfonyl)phenylazo]benzenesulfonic acid dissolved in 300 parts of water at pH 6-7 , the diazo compound prepared in step a) is added dropwise, and the pH is maintained between 6-7 with 20% strength sodium carbonate solution. The temperature is 20-25°C, and the stirring is continued until the reaction is completed. The finally obtained reaction mixture was dried under reduced pressure.

[0127] The obtained dye (λ max =430nm) accord with formula (1a)

[0128]

[0129] And dyes the cotton an orange hue.

Embodiment 2

[0131] The 3-aminobenzoic acid in embodiment 1 is replaced with 13.6 parts of 3-amino-benzamide, adopts the reaction process identical with embodiment 1, makes the dyestuff (λ with formula (1b) max =427nm).

[0132]

[0133] (λ max =427nm).

Embodiment 3

[0135] The 3-aminobenzoic acid in embodiment 1 is replaced by 3-aminobenzonitrile, adopts the reaction process identical with embodiment 1, obtains the dyestuff (λ with formula (1c) max =421nm).

[0136]

[0137] (λ max =421nm).

[0138] Examples 4 to 15, preparation of compounds of general formula (1d), wherein D is as defined in the table, can be prepared by the same steps as in Example 1.

[0139]

[0140]

[0141]

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