HIGH WET FAST DISPERSE DYE MIXTURES

Abstract

The present invention is directed to dye mixtures comprising dye(s) of formula (1)

##STR00001##

and specific other dyes, the process for the production of these mixtures as well as their use for dyeing textiles.

Claims

1. A dye mixture comprising at least one dye of formula (1) ##STR00040## and at least one dye selected from the group consisting of dyes of formulae (3a), (3b), (3c), (3d), (3e), (3f), (3g), (3h) and (3i) ##STR00041## ##STR00042## wherein independent from each other R.sup.1 is hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkenyl, (CH.sub.2).sub.nO(C.sub.1-C.sub.4)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.4)-alkyl, (CH.sub.2).sub.nCOOR.sup.100 or (CH.sub.2).sub.nCN, R.sup.2 is hydrogen, NHCO(C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkyl, R.sup.3 is hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.4 and R.sup.5 are hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkenyl, (CH.sub.2).sub.nO(C.sub.1-C.sub.4)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.4)-alkyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.4)-alkyl or CHCH.sub.3COO(C.sub.1-C.sub.4)-alkyl, R.sup.6 and R.sup.7 are hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy or halogen, R.sup.8 and R.sup.9 are hydrogen, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.4)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.4)-alkyl, R.sup.10 and R.sup.11 are hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkenyl, (CH.sub.2).sub.nO(C.sub.1-C.sub.4)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.4)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.4)-alkyl, R.sup.12 to R.sup.16 are hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.100 is (C.sub.1-C.sub.4)-alkyl, phenyl or benzyl, X.sup.1 and X.sup.2 are hydrogen, nitro, cyano, halogen or carboxy, X.sup.3 and X.sup.4 are hydrogen, cyano, or halogen, Y.sup.1 is hydrogen, (CH.sub.2).sub.m-phenyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkenyl, (CH.sub.2).sub.nO(C.sub.1-C.sub.4)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.4)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.4)-alkyl, T.sup.1 to T.sup.3 are hydrogen, carboxy, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkyoxy, halogen, cyano or nitro n is 1, 2, 3 or 4, m is 1, 2, 3 or 4, V is hydrogen, OH, O(C.sub.1-C.sub.4)-alkyl, halogen, OCH.sub.2COCH.sub.3, CH.sub.2-pyrolidonyl or SO.sub.2NH(CH.sub.2).sub.nO(C.sub.1-C.sub.4)-alkyl, k is 2 to 8 and U.sup.1 and U.sup.2 are TABLE-US-00007 U.sup.1 U.sup.2 H H H H H H H H H whereby * marks the linkage to the phenyl-ring.

2. The dye mixture according to claim 1 wherein independent from each other R.sup.1 is hydrogen, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.2)-alkenyl, (CH.sub.2)O(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCN, R.sup.2 is hydrogen, NHCO(C.sub.1-C.sub.2)-alkyl or (C.sub.1-C.sub.2)-alkyl, R.sup.3 is hydrogen, methyl or ethyl, R.sup.4 and R.sup.5 are hydrogen, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.2)-alkenyl, (CH.sub.2).sub.nO(C.sub.1-C.sub.2)-alkyl, (CH.sub.2)OCO(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or CHCH.sub.3COO(C.sub.1-C.sub.2)-alkyl, R.sup.6 and R.sup.7 are hydrogen, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.2)-alkoxy, bromo or chloro, R.sup.8 and R.sup.9 are hydrogen, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl, R.sup.10 and R.sup.11 are hydrogen, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.2)-alkoxy, (C.sub.1-C.sub.4)-alkenyl, (CH.sub.2).sub.nO(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl, R.sup.12 to R.sup.16 are hydrogen or (C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, nitro, cyano, bromo, chloro or COO(C.sub.1-C.sub.2)-alkyl X.sup.3 and X.sup.4 are hydrogen, bromo or chloro, Y.sup.1 is hydrogen, (CH.sub.2).sub.m-phenyl, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.4)-alkenyl, (CH.sub.2)O(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl, T.sup.1 to T.sup.3 are hydrogen, COO(C.sub.1-C.sub.2)-alkyl, bromo, chloro, cyano or nitro n is 1, 2 or 3, m is 1 or 2, V is hydrogen, OH, O(C.sub.1-C.sub.2)-alkyl, halogen, OCH.sub.2COCH.sub.3, CH.sub.2-pyrolidonyl or SO.sub.2NH(CH.sub.2).sub.nO(C.sub.1-C.sub.2)-alkyl, k is 3 to 6 and U.sup.1 and U.sup.2 are TABLE-US-00008 U.sup.1 U.sup.2 H H H whereby * marks the linkage to the phenyl-ring.

3. The dye mixture according to claim 1, wherein independent from each other R.sup.1 is ethyl, cyanoethyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl, R.sup.2 is hydrogen or NHCOCH.sub.3, R.sup.3 is methyl or ethyl, R.sup.4 and R.sup.5 are (C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nO(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or CHCH.sub.3COO(C.sub.1-C.sub.2)-alkyl, R.sup.6, R.sup.7, R.sup.12 to R.sup.16 and T.sup.2 are hydrogen, R.sup.8 and R.sup.9 are (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl, R.sup.10 and R.sup.11 are (CH.sub.2).sub.nO(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl, X.sup.1, X.sup.2, X.sup.3, T.sup.1 and T.sup.3 are hydrogen, nitro, cyano, bromo or chloro, X.sup.4 is bromo or cyano, Y.sup.1 is (CH.sub.2).sub.n-phenyl, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.4)-alkenyl, (C.sub.1-C.sub.2)-alkoxy, (CH.sub.2).sub.nO(C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.nOCO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl, n and m are 1 or 2 and U.sup.1 and U.sup.2 are TABLE-US-00009 U.sup.1 U.sup.2 H H H whereby * marks the linkage to the phenyl-ring.

4. The dye mixture according to claim 1, wherein the dye or dyes of formula (1) is/are selected from the group consisting of: ##STR00068## ##STR00069##

5. The dye mixture according to claim 1, wherein the dye or dyes of formula (3a) are selected from the group consisting of ##STR00070##

6. The dye mixture according to claim 1, wherein the dye or dyes of formula (3b) are selected from the group consisting of ##STR00071##

7. The dye mixture according to claim 1, wherein the dye or dyes of formula (3c) are selected from the group consisting of ##STR00072##

8. The dye mixture according to claim 1, wherein the dye or dyes of formula (3d) are selected from the group consisting of ##STR00073## ##STR00074##

9. The dye mixture according to claim 1, wherein the dye or dyes of formula (3e) are selected from the group consisting of: ##STR00075##

10. The dye mixture according to claim 1, wherein the dye or dyes of formula (3f) are selected from the group consisting of: ##STR00076##

11. The dye mixture according to claim 1, wherein the dye or dyes of formula (3i) are selected from the group consisting of: ##STR00077##

12. The dye mixture according to claim 1, wherein the amount of dyes in weight % of the overall amount of dyes in the mixture is: TABLE-US-00010 (1) 80 to 20 sum of (3a/3b/3c/3d/3e/3f/3g/3h/3i) 20 to 80.

13. A process for the production of a dye mixture according to claim 1, comprising a) mixing at least one dye of formula (1) with at least one dye of any one of formula (3a) to (3i) and b) homegenizing the mixture obtained in step a) forms another aspect of the present invention.

14. Aqueous solution comprising the dye mixture according to claim 1.

Description

EXAMPLE 1

[0109] 50 parts dye of the formula (1-7) were mixed with 50 parts of a dye of the formula (3d-1).

[0110] The resulting dye mixture of the invention was formulated using dispersing agent, glass bead milling and dried via spray drying. The resulting Dyestuff mixture gives deep red dyeing's and prints with good build-up and wet-fastness, both on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

EXAMPLE 2

[0111] 70 parts dye of the formula (1-6) were mixed with 25 parts of a dye of the formula (3f-1) and mixed with 5 parts of a dye powder of the formula (1-3).

[0112] The resulting dye mixture of the invention was formulated using dispersing agent, glass bead milling and dried via spray drying. The resulting Dyestuff mixture gives bright scarlet dyeing's and prints with very good wet-fastness, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

EXAMPLE 3

[0113] 60 parts dye of the formula (1-6) were mixed with 40 parts of a dye powder of the formula (3a-1).

[0114] The resulting dye mixture of the invention was formulated using dispersing agent, glass bead milling and dried via spray drying. The resulting Dyestuff mixture gives red dyeing's and prints with good build-up and wet-fastness, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

EXAMPLE 4

[0115] 71 parts dye of the formula (1-6) were mixed with 29 parts of a dye powder of the formula (3f-2).

[0116] The resulting dye mixture of the invention was formulated using dispersing agent, glass bead milling and dried via spray drying. The resulting Dyestuff mixture gives bright red dyeing's or prints with very good wet-fastness, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

EXAMPLE 5

[0117] 50 parts dye of the formula (1-7) were mixed with 50 parts of a dye of the formula (3g-1).

[0118] The resulting dye mixture of the invention was formulated using dispersing agent, glass bead milling and dried via spray drying. The resulting Dyestuff mixture gives bright red dyeing's or prints with good wet-fastness, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

EXAMPLE 6

[0119] 55 parts dye of the formula (1-6) were mixed with 5 parts of a dye of the formula (1-3) and mixed with 40 parts of a dye of the formula (3c-4).

[0120] The resulting dye mixture of the invention was formulated using dispersing agent, glass bead milling and dried via spray drying. The resulting Dyestuff mixture gives deep red dyeings or prints with good build-up and wet-fastness, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

[0121] All examples of the following tables are prepared as formulations as explained above. The shades of the dyeings or prints on polyester are red or scarlet.

TABLE-US-00006 Example Dye of formula (1) Dye of formula (1) Dye of formula (1) Dye of formula (3) Dye of formula (3) Ratio 7 1-3 3a-1 61:39 8 1-3 3b-1 70:30 9 1-3 3b-2 60:40 10 1-3 3b-3 70:30 11 1-3 3b-4 40:60 12 1-3 3c-4 70:30 1 1-3 3c-4 60:40 14 1-3 3c-4 50:50 15 1-3 3d-1 70:30 16 1-3 3d-1 60:40 17 1-3 3d-1 50:50 18 1-3 3d-3 65:35 19 1-3 3d-5 40:60 20 1-3 3d-9 70:30 21 1-3 3e-1 75:25 22 1-3 3f-1 80:20 23 1-3 3f-2 70:30 24 1-3 3f-3 50:50 25 1-3 3f-4 60:40 26 1-3 3i-1 70:30 27 1-3 3g-1 40:60 28 1-9 3g-2 20:80 29 1-3 3g-3 50:50 30 1-3 3g-4 50:50 31 1-10 3h-1 55:45 32 1-6 3b-1 65:35 33 1-6 3b-2 60:40 34 1-6 3b-3 70:30 35 1-6 3b-4 65:35 36 1-6 3c-4 70:30 37 1-6 3c-4 60:40 38 1-6 3c-4 50:50 39 1-6 3d-1 75:25 40 1-6 3d-1 65:35 41 1-6 3d-1 55:45 42 1-6 3d-3 65:35 43 1-6 3d-5 50:50 44 1-6 3d-9 70:30 45 1-6 3e-1 75:25 46 1-6 3f-1 80:20 47 1-6 3f-3 50:50 48 1-6 3f-4 60:40 49 1-6 3i-1 70:30 50 1-6 3g-1 40:60 51 1-6 3g-2 55:45 52 1-6 3g-3 20:80 53 1-6 3g-4 50:50 54 1-6 3h-1 55:45 55 1-7 3a-1 65:35 56 1-7 3b-1 65:35 57 1-7 3b-2 60:40 58 1-7 3b-3 70:30 59 1-7 3b-4 65:35 60 1-7 3c-4 70:30 61 1-7 3c-4 60:40 62 1-7 3c-4 50:50 63 1-7 3d-1 75:25 64 1-7 3d-1 65:35 65 1-7 3d-3 65:35 66 1-7 3d-5 50:50 67 1-7 3d-9 70:30 68 1-7 3e-1 75:25 69 1-7 3f-1 80:20 70 1-9 3f-2 70:30 71 1-7 3f-3 50:50 72 1-7 3f-4 40:60 73 1-10 3i-1 70:30 74 1-7 3g-2 40:60 75 1-7 3g-3 50:50 76 1-7 3g-4 20:80 77 1-7 3h-1 55:45 78 1-3 1-6 1-7 3c-4 30:10:20:40 79 1-3 1-6 3c-4 55:10:35 80 1-3 1-7 3c-4 60:10:30 81 1-6 1-7 3c-4 60:5:35 82 1-3 3c-4 3d-1 50:25:25 83 1-3 3c-4 3d-5 60:20:20 84 1-6 3c-4 3d-1 60:15:25 85 1-6 3c-4 3d-5 55:20:25 86 1-6 1-3 3a-1 59:6:35 87 1-6 1-3 3b-1 59:6:35 88 1-6 1-3 3b-2 55:5:40 89 1-6 1-3 3b-3 64:6:30 90 1-6 1-3 3b-4 59:6:35 91 1-6 1-3 3c-4 55:5:40 92 1-6 1-3 3d-1 55:5:40 93 1-6 1-3 3d-3 50:5:45 94 1-6 1-3 3d-5 59:6:35 95 1-6 1-3 3d-9 46:4:50 96 1-6 1-3 3e-1 64:6:30 97 1-6 1-3 3f-2 73:7:20 98 1-6 1-3 3f-3 64:6:30 99 1-6 1-3 3f-4 45:5:50 100 1-6 1-3 3i-1 54:6:40 101 1-6 1-3 3g-1 64:6:30 102 1-6 1-3 3g-2 55:5:40 103 1-6 1-3 3g-3 50:5:45 104 1-6 1-3 3g-4 45:5:50 105 1-6 1-3 3h-1 45:5:50 106 1-6 1-3 3h-1 3d-1 45:5:25:25