High wet fast disperse dye mixtures

Abstract

Dye mixtures based on dye(s) of formula (1) ##STR00001##
and dye(s) of formula (2) ##STR00002##
formula (3) ##STR00003##
formula (4) ##STR00004##
formula (5a) ##STR00005##
and/or formula (5b) ##STR00006##

Claims

1. A dye mixture comprising comprising at least one dye of formula (1) ##STR00070## and at least one dye of formula (2) ##STR00071## and optionally one or more dyes selected from the group consisting of dyes of formulae (3), (4), (5a) and (5b) ##STR00072## wherein independent from each other R.sup.1 is hydrogen, (C.sub.1-C.sub.4)-alkyl or halogen, R.sup.2 is hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.3 to R.sup.6 is (C.sub.1-C.sub.4)-alkyl, (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, (CH.sub.2).sub.n-phenyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.4)-alkyl, X.sup.1 to X.sup.8 is hydrogen, halogen, nitro, cyano, SCN, carboxy or CONR.sup.2R.sup.3, Y.sup.1 is hydrogen, (C.sub.1-C.sub.4)-alkyl, substituted (C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl or (CH.sub.2).sub.m-phenyl, Y.sup.2 is phenyl or (CH.sub.2).sub.m-phenyl, both substituted by Y.sup.6, Y.sup.3 is hydrogen or (C.sub.1-C.sub.4)-alkyl, Y.sup.4 is (C.sub.1-C.sub.8-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.5 is hydrogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkoxy, Y.sup.6 is hydrogen, nitro, cyano, carboxy, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkoxy, and n and m is 1, 2, 3 or 4.

2. The dye mixture according to claim 1, wherein independent from each other R.sup.1 is hydrogen or (C.sub.1-C.sub.2)-alkyl, R.sup.2 is (C.sub.1-C.sub.2)-alkyl, R.sup.3 to R.sup.6 is (C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.n-phenyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3 and X.sup.7 are nitro or cyano, X.sup.4 is hydrogen, nitro or cyano, X.sup.5 and X.sup.6 are hydrogen, bromo, chloro, nitro or cyano, X.sup.8 is hydrogen, nitro or cyano, Y.sup.1 is (C.sub.1-C.sub.4)-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.2 is phenyl or (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen, or (C.sub.1-C.sub.2)-alkyl Y.sup.4 is (C.sub.1-C.sub.8-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.5 is hydrogen, (C.sub.1-C.sub.2)-alkyl or (C.sub.1-C.sub.2)-alkoxy, and n and m is 1 or 2.

3. The dye mixture according to claim 1, wherein independent from each other R.sup.1 is hydrogen or methyl, R.sup.2 is methyl or ethyl, R.sup.3 to R.sup.6 is (C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.n-phenyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3, X.sup.4 and X.sup.7 are nitro, X.sup.5 and X.sup.6 are hydrogen, bromo, chloro, nitro or cyano, X.sup.8 is hydrogen, Y.sup.1 and Y.sup.2 are (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen or methyl, Y.sup.4 is (C.sub.1-C.sub.8)-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.5 is hydrogen, O-methyl or O-ethyl, and n and m is 1 or 2.

4. The dye mixture according to claim 1, wherein independent from each other R.sup.1 is hydrogen, R.sup.2 is methyl or ethyl, R.sup.3 to R.sup.6 is (C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.n-phenyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3, X.sup.4 and X.sup.7 are nitro, X.sup.5 and X.sup.6 are hydrogen, bromo, chloro, nitro or cyano, X.sup.8 is hydrogen, Y.sup.1 and Y.sup.2 are (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen, Y.sup.4 is (C.sub.1-C.sub.4)-alkyl, Y.sup.5 is hydrogen or O-methyl, and n and m is 1 or 2.

5. The dye mixture according to claim 1, comprising at least one dye selected from the group consisting of dyes of formulae (3), (4), (5a) and (5b).

6. The dye mixture according to claim 1, comprising at least two dyes of formula (3).

7. The dye mixture according to claim 1, comprising at least two dyes of formula (3) and at least one dye selected from the group consisting of dyes of formulae (4), (5a) and (5b).

8. A dye mixture comprising at least one dye of formula (3) and at least one dye of formula (4) ##STR00073## and at least one dye of formula (1) ##STR00074## and optionally one or more dyes selected from the group consisting of dyes of formulae (2), (5a) and (5b) ##STR00075## wherein independent from each other R.sup.1 is hydrogen, (C.sub.1-C.sub.4)-alkyl or halogen, R.sup.2 is hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.3 and R.sup.4 are identical or different and are (C.sub.1-C.sub.4)-alkyl, (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, (CH.sub.2).sub.n-phenyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.4)-alkyl, R.sup.5 and R.sup.6 are identical or different and are (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, (CH.sub.2).sub.n-phenyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.4)-alkyl, n1 is 1, 3 or 4, X.sup.1 to X.sup.8 is hydrogen, halogen, nitro, cyano, SCN, carboxy or CONR.sup.2R.sup.3, Y.sup.1 is hydrogen, (C.sub.1-C.sub.4)-alkyl, substituted (C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl or (CH.sub.2).sub.m-phenyl, Y.sup.2 is phenyl or (CH.sub.2).sub.m-phenyl, both substituted by Y.sup.6, Y.sup.3 is hydrogen or (C.sub.1-C.sub.4)-alkyl, Y.sup.4 is (C.sub.1-C.sub.8-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.5 is hydrogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkoxy, Y.sup.6 is hydrogen, nitro, cyano, carboxy, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkoxy, and n and m is 1, 2, 3 or 4.

9. The dye mixture according to claim 8, wherein independent from each other R.sup.1 is hydrogen or (C.sub.1-C.sub.2)-alkyl, R.sup.2 is (C.sub.1-C.sub.2)-alkyl, R.sup.3 to R.sup.6 is (C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.n-phenyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3 and X.sup.7 are nitro or cyano, X.sup.4 is hydrogen, nitro or cyano, X.sup.5 and X.sup.6 are hydrogen, bromo, chloro, nitro or cyano, X.sup.8 is hydrogen, nitro or cyano, Y.sup.1 is (C.sub.1-C.sub.4)-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.2 is phenyl or (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen, or (C.sub.1-C.sub.2)-alkyl, Y.sup.4 is (C.sub.1-C.sub.8-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.5 is hydrogen, (C.sub.1-C.sub.2)-alkyl or (C.sub.1-C.sub.2)-alkoxy, and n and m is 1 or 2.

10. The dye mixture according to claim 8, wherein independent from each other R.sup.1 is hydrogen or methyl, R.sup.2 is methyl or ethyl, R.sup.3 to R.sup.6 is (C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.n-phenyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3, X.sup.4 and X.sup.7 are nitro, X.sup.5 and X.sup.6 are hydrogen, bromo, chloro, nitro or cyano, X.sup.8 is hydrogen, Y.sup.1 and Y.sup.2 are (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen or methyl, Y.sup.4 is (C.sub.1-C.sub.8)-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.5 is hydrogen, O-methyl or O-ethyl, and n and m is 1 or 2.

11. The dye mixture according to claim 8, wherein independent from each other R.sup.1 is hydrogen, R.sup.2 is methyl or ethyl, R.sup.3 to R.sup.6 is (C.sub.1-C.sub.2)-alkyl, (CH.sub.2).sub.n-phenyl, (CH.sub.2).sub.nCOO(C.sub.1-C.sub.2)-alkyl or (CH.sub.2).sub.nCOO(CH.sub.2).sub.mCO(C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3, X.sup.4 and X.sup.7 are nitro, X.sup.5 and X.sup.6 are hydrogen, bromo, chloro, nitro or cyano, X.sup.8 is hydrogen, Y.sup.1 and Y.sup.2 are (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen, Y.sup.4 is (C.sub.1-C.sub.4)-alkyl, Y.sup.5 is hydrogen or O-methyl, and n and m is 1 or 2.

12. The dye mixture according to claim 8, comprising at least two dyes of formula (3).

13. The dye mixture according to claim 8, comprising at least one dye of formula (2).

14. The dye mixture according to claim 8, comprising at least one dye of formulae (4) and (5a).

15. A dye mixture comprising at least one dye of formula (1) ##STR00076## and one or more dyes selected from the group consisting of dyes of formulae (2), (5a) and (5b) ##STR00077## wherein independent from each other R.sup.1 is hydrogen, (C.sub.1-C.sub.4)-alkyl or halogen, R.sup.2 is hydrogen or (C.sub.1-C.sub.4)-alkyl, X.sup.1 to X.sup.4 and X.sup.8 are independently a hydrogen, halogen, nitro, cyano, SCN, carboxy or CONR.sup.2R.sup.2, Y.sup.1 is hydrogen, (C.sub.1-C.sub.4)-alkyl, substituted (C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl or (CH.sub.2).sub.m-phenyl, Y.sup.2 is phenyl or (CH.sub.2).sub.m-phenyl, both substituted by Y.sup.6, Y.sup.3 is hydrogen or (C.sub.1-C.sub.4)-alkyl, Y.sup.4 is (C.sub.1-C.sub.8)-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.6 is hydrogen, nitro, cyano, carboxy, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkoxy, and n and m is 1, 2, 3 or 4.

16. The dye mixture according to claim 15, wherein independent from each other R.sup.1 is hydrogen or (C.sub.1-C.sub.2)-alkyl, R.sup.2 is (C.sub.1-C.sub.2)-alkyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3 is nitro or cyano, X.sup.4 and X.sup.8 are hydrogen, nitro or cyano, Y.sup.1 is (C.sub.1-C.sub.4)-alkyl or (CH.sub.2).sub.m-phenyl, Y.sup.2 is phenyl or (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen, or (C.sub.1-C.sub.2)-alkyl, Y.sup.4 is (C.sub.1-C.sub.3)-alkyl, and n and m is 1 or 2.

17. The dye mixture according to claim 15, wherein independent from each other R.sup.1 is hydrogen or methyl, R.sup.2 is methyl or ethyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3, and X.sup.4 are nitro, X.sup.8 is hydrogen, Y.sup.1 and Y.sup.2 are (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen or methyl, Y.sup.4 is (C.sub.1-C.sub.8)-alkyl, and n and m is 1 or 2.

18. The dye mixture according to claim 15, wherein independent from each other R.sup.1 is hydrogen, R.sup.2 is methyl or ethyl, X.sup.1 and X.sup.2 are hydrogen, bromo, chloro, nitro or cyano, X.sup.3, and X.sup.4 are nitro, X.sup.8 is hydrogen, Y.sup.1 and Y.sup.2 are (CH.sub.2).sub.m-phenyl, Y.sup.3 is hydrogen, Y.sup.4 is (C.sub.1-C.sub.4)-alkyl, and n and m is 1 or 2.

19. The dye mixture according to claim 15, comprising at least one dye of formula (2).

20. The dye mixture according to claim 15, comprising at least one dye of formula (5a).

21. The dye mixture according to claim 15, comprising at least one dye of formula (5b).

22. An aqueous solution for dying comprising the dye mixture according to claim 1.

23. A process for the production of the dye mixture according to claim 1 comprising a) mixing dye(s) of formula (1) with the required amount of dye(s) according to formulae (2), (3), (4), (5a) and/or (5b), b) homogenizing the mixture obtained in step a).

24. A process for dyeing or printing carboxamido- and/or hydroxyl-containing material, comprising contacting the carboxamido- and/or hydroxyl-containing material with the dye mixture according to claim 1.

25. An ink for digital textile printing comprising the dye mixture according to claim 1.

26. Fiber and blends containing such fiber selected from the group consisting of: synthetic fiber materials, nylon materials, nylon-6, nylon-6.6 and aramid fibres, vegetable fibres, seed fibres, cotton, organic cotton, kapok, coir from coconut husk; bast fibers, flax, hemp, jute, kenaf, ramie, rattan; leaf fibres, sisal, henequen, banana; stalk fibres, bamboo; fibres from animals, wool, organic wool, silk, cashmere wool, alpaca fiber, mohair, Angora fibre as well as fur and leather materials; manufactured, regenerated and recycled fibres, cellulosic fibres; paper fibres, cellulosic regenerated fibres, viscose rayon fibres, acetate and triacetate fibers, and Lyocell fibers comprising the dye mixture according to claim 1 either in chemically and/or physically bound form.

27. The dye mixture according to claim 1 which comprises a) at least two different dyes of formula (3), b) at least one dye of formula (3) and at least one dye of formula (4) or c) at least two different dyes of formula (3) and at least one dye of formula (4).

28. An aqueous solution for dying comprising the dye mixture according to claim 8.

29. A process for the production of the dye mixture according to claim 8 comprising a) mixing dye(s) of formula (1) with the required amount of dye(s) according to formulae (2), (3), (4), (5a) and/or (5b), b) homogenizing the mixture obtained in step a).

30. A process for dyeing or printing carboxamido- and/or hydroxyl-containing material, comprising contacting the carboxamido- and/or hydroxyl-containing material with the dye mixture according to claim 8.

31. An ink for digital textile printing comprising the dye mixture according to claim 8.

32. Fiber and blends containing such fiber selected from the group consisting of: synthetic fiber materials, nylon materials, nylon-6, nylon-6.6 and aramid fibres, vegetable fibres, seed fibres, cotton, organic cotton, kapok, coir from coconut husk; bast fibers, flax, hemp, jute, kenaf, ramie, rattan; leaf fibres, sisal, henequen, banana; stalk fibres, bamboo; fibres from animals, wool, organic wool, silk, cashmere wool, alpaca fiber, mohair, Angora fibre as well as fur and leather materials; manufactured, regenerated and recycled fibres, cellulosic fibres; paper fibres, cellulosic regenerated fibres, viscose rayon fibres, acetate and triacetate fibers, and Lyocell fibers comprising the dye mixture according to claim 8 either in chemically and/or physically bound form.

33. An aqueous solution for dying comprising the dye mixture according to claim 15.

34. A process for the production of the dye mixture according to claim 15 comprising a) mixing dye(s) of formula (1) with the required amount of dye(s) according to formulae (2), (3), (4), (5a) and/or (5b), b) homogenizing the mixture obtained in step a).

35. A process for dyeing or printing carboxamido- and/or hydroxyl-containing material, comprising contacting the carboxamido- and/or hydroxyl-containing material with the dye mixture according to claim 15.

36. An ink for digital textile printing comprising the dye mixture according to claim 15.

37. Fiber and blends containing such fiber selected from the group consisting of: synthetic fiber materials, nylon materials, nylon-6, nylon-6.6 and aramid fibres, vegetable fibres, seed fibres, cotton, organic cotton, kapok, coir from coconut husk; bast fibers, flax, hemp, jute, kenaf, ramie, rattan; leaf fibres, sisal, henequen, banana; stalk fibres, bamboo; fibres from animals, wool, organic wool, silk, cashmere wool, alpaca fiber, mohair, Angora fibre as well as fur and leather materials; manufactured, regenerated and recycled fibres, cellulosic fibres; paper fibres, cellulosic regenerated fibres, viscose rayon fibres, acetate and triacetate fibers, and Lyocell fibers comprising the dye mixture according to claim 15 either in chemically and/or physically bound form.

Description

EXAMPLES

Example 1

(1) 15 parts dye of the formula (1-1)

(2) ##STR00021##
were mixed with 30 parts of a dye of the formula (2-1)

(3) ##STR00022##
and mixed with 55 parts of a dye powder of the formula (3-1)

(4) ##STR00023##

(5) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep black dyeings and prints, on polyester or polyester blends using dyeing conditions typical for disperse dyes.

Example 2

(6) 20 parts dye of the formula (1-2)

(7) ##STR00024##
were mixed with 24 parts of a dye of the formula (2-2)

(8) ##STR00025##
and mixed with 56 parts of a dye powder of the formula (4-1)

(9) ##STR00026##

(10) The resulting inventive dye mixture was formulated using dispersing agent and dried via spray drying and gives deep black dyeings and prints e.g. on polyester or polyester blends when used under the dyeing conditions typical for disperse dyes.

Example 3

(11) 20 parts dye of the formula (1-3)

(12) ##STR00027##
were mixed with 22 parts of a dye of the formula (2-3)

(13) ##STR00028##
and mixed with 26 parts of a dye powder of the formula (3-2)

(14) ##STR00029##
and mixed with 32 parts of a dye powder of the formula (4-2)

(15) ##STR00030##

(16) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep black dyeings or prints, on polyester or polyester blends for example when applying the dyeing conditions typical for disperse dyes.

Example 4

(17) 18 parts dye of the formula (1-4)

(18) ##STR00031##
were mixed with 20 parts of a dye of the formula (2-4)

(19) ##STR00032##
and mixed with 32 parts of a dye powder of the formula (3-3)

(20) ##STR00033##
and mixed with 22 parts of a dye powder of the formula (3-4)

(21) ##STR00034##
and mixed with 8 parts of a dye powder of the formula (5a-1)

(22) ##STR00035##

(23) The resulting inventive dye mixture was formulated using dispersing agent and dried via spray drying and gives deep black dyeings and prints e.g. on polyester or polyester blends under the dyeing conditions typical for disperse dyes.

Example 5

(24) 25 parts dye of the formula (1-4)

(25) ##STR00036##
were mixed with 20 parts of a dye of the formula (2-4)

(26) ##STR00037##
and mixed with 49 parts of a dye powder of the formula (4-3)

(27) ##STR00038##
and mixed with 6 parts of a dye powder of the formula (5b-1)

(28) ##STR00039##

(29) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep black dyeings and prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 6

(30) 18 parts dye of the formula (1-4)

(31) ##STR00040##
were mixed with 17 parts of a dye of the formula (2-4)

(32) ##STR00041##
and mixed with 25 parts of a dye powder of the formula (3-3)

(33) ##STR00042##
and mixed with 32 parts of a dye powder of the formula (3-5)

(34) ##STR00043##
and mixed with 8 parts of a dye powder of the formula (5a-1)

(35) ##STR00044##

(36) The resulting inventive dye mixture was formulated using dispersing agent and dried via spray drying and gives deep black dyeings or prints both on polyester or polyester blends for example using the dyeing conditions typical for disperse dyes.

Example 7

(37) 29 parts dye of the formula (1-4)

(38) ##STR00045##
were mixed with 34 parts of a dye of the formula (2-5)

(39) ##STR00046##
and mixed with 37 parts of a dye powder of the formula (5b-1)

(40) ##STR00047##

(41) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep brown dyeings or prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 8

(42) 21 parts dye of the formula (1-6)

(43) ##STR00048##
and 47 parts of a dye powder of the formula (1-7)

(44) ##STR00049##
were mixed with 32 parts of a dye of the formula (2-6)

(45) ##STR00050##

(46) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep brown dyeings or prints, on polyester or polyester blends both e.g. under the dyeing conditions typical for disperse dyes.

Example 9

(47) 45 parts dye of the formula (1-7)

(48) ##STR00051##
were mixed with 55 parts of a dye of the formula (3-5)

(49) ##STR00052##

(50) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep black dyeings or prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 10

(51) 25 parts dye of the formula (1-4)

(52) ##STR00053##
and mixed with 75 parts of a dye powder of the formula (4-3)

(53) ##STR00054##

(54) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep black dyeings or prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 11

(55) 31 parts dye of the formula (1-1)

(56) ##STR00055##
were mixed with 69 parts of a dye of the formula (2-1)

(57) ##STR00056##

(58) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep brown dyeings and prints, both on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 12

(59) 75 parts dye of the formula (1-2)

(60) ##STR00057##
were mixed with 20 parts of a dye of the formula (2-2)

(61) ##STR00058##
and mixed with 5 parts of a dye powder of the formula (5a-1)

(62) ##STR00059##

(63) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives yellow brown dyeings and prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 13

(64) 85 parts dye of the formula (1-3)

(65) ##STR00060##
were mixed with 15 parts of a dye powder of the formula (5b-1)

(66) ##STR00061##

(67) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives yellow brown dyeings and prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 14

(68) 71 parts dye of the formula (1-4)

(69) ##STR00062##
were mixed with 29 parts of a dye powder of the formula (5b-2)

(70) ##STR00063##

(71) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep brown dyeings or prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 15

(72) 29 parts dye of the formula (1-4)

(73) ##STR00064##
were mixed with 34 parts of a dye of the formula (2-2)

(74) ##STR00065##
and mixed with 37 parts of a dye powder of the formula (5b-1)

(75) ##STR00066##

(76) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep brown dyeings or prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

Example 16

(77) 21 parts dye of the formula (1-5)

(78) ##STR00067##
were mixed with 47 parts of a dye powder of the formula (1-6)

(79) ##STR00068##
and mixed with 32 parts of a dye of the formula (2-6)

(80) ##STR00069##

(81) The resulting dye mixture of the invention was formulated using dispersing agent and dried via spray drying and gives deep brown dyeings or prints, on polyester or polyester blends for example, under the dyeing conditions typical for disperse dyes.

(82) All examples of the following tables are prepared as formulations as explained above.

(83) TABLE-US-00005 TABLE 1 Dye of formula Dye of formula 1.sup.st Dye of formula 2.sup.nd Dye of Example (1) (2) (3) formula (3) 17 X.sup.1 = CN, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.5 = Cl X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-(p- X.sup.6 = NO.sub.2 R.sup.1 = CH.sub.3 Toloudin) R.sup.2 = C.sub.2H.sub.5 R.sup.2 = C.sub.2H.sub.5 Y.sup.4 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = C.sub.2H.sub.5 R.sup.3 = C.sub.2H.sub.4COOCH.sub.3 Y.sup.3 = H R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 18 X.sup.1 = NO.sub.2, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-(p- R.sup.1 = H R.sup.2 = C.sub.2H.sub.5 Chloro-phenyl) Y.sup.1 = C.sub.2H.sub.5 Y.sup.4 = C.sub.2H.sub.5 Y.sup.3 = H n = 2, m = 1 19 X.sup.1 = CN, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.5 = Cl X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-(p- X.sup.6 = NO.sub.2 R.sup.1 = H R.sup.2 = CH.sub.3 methoxy-phenyl) R.sup.2 = CH.sub.3 Y.sup.1 = C.sub.2H.sub.5 Y.sup.4 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.3 = H R.sup.3 = CH.sub.2COOCH.sub.3 n = 2, m = 1 R.sup.4 = CH.sub.2COOCH.sub.3 20 X.sup.1 = CN, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.5 = CN X.sup.5 = CN X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.5 = H Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = C.sub.2H.sub.5 R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 21 X.sup.1 = CN, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl R.sup.1 = H Y.sup.4 = C.sub.2H.sub.5 R.sup.2 = C.sub.2H.sub.5 Y.sup.1 = CH.sub.2- phenyl n = 2, m = 1 22 X.sup.1 = CN, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.5 = H X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = CH.sub.3 Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = CH.sub.3 R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 23 X.sup.1 = NO.sub.2, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl R.sup.1 = H Y.sup.4 = C.sub.2H.sub.5 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2, m = 1 24 X.sup.1 = CN, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2, m = 1 25 X.sup.1 = Br, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl R.sup.1 = H Y.sup.4 = C.sub.2H.sub.5 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2, m = 1 26 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2, m = 1 27 X.sup.1 = Br, X.sup.2 = Br X.sup.4 = CN X.sup.5 = Br X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = CH.sub.3 Y.sup.4 = C.sub.2H.sub.5 R.sup.2 = CH.sub.3 R.sup.2 = C.sub.2H.sub.5 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = CH.sub.3 R.sup.4 = CH.sub.2-phenyl n = 2, m = 1 28 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.5 = CN X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = H Y.sup.1 = CH.sub.2-phenyl R.sup.3 = C.sub.2H.sub.4COOCH.sub.2COCH.sub.3 Y.sup.3 = H R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 29 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl R.sup.1 = H Y.sup.4 = C.sub.3H.sub.7 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2, m = 1 30 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.5 = Cl X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 31 X.sup.1 = Cl, X.sup.2 = Br X.sup.4 = NO.sub.2 X.sup.5 = Br X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = CH.sub.2-phenyl n = 2, m = 1 32 X.sup.1 = Br, X.sup.2 = Br X.sup.4 = NO.sub.2 X.sup.5 = Cl X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = C.sub.2H.sub.5 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = CH.sub.3 n = 2, m = 1 33 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.5 = CN X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 34 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2, m = 1 35 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.5 = Br X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = C.sub.2H.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 36 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.5 = Br X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 37 X.sup.1 = CN, X.sup.2 = H X.sup.4 = NO.sub.2 X.sup.5 = Cl X.sup.5 = CN X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.5 = H Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH2COOCH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = CH2COOCH.sub.3 R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 38 X.sup.1 = Cl, X.sup.2 = Cl X.sup.4 = NO.sub.2 X.sup.5 = Cl X.sup.5 = CN X.sup.3 = NO.sub.2 Y.sup.2 = CH.sub.2-phenyl X.sup.6 = NO.sub.2 X.sup.6 = NO.sub.2 R.sup.1 = H Y.sup.4 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 Y.sup.5 = H Y.sup.1 = CH.sub.2-phenyl R.sup.3 = CH.sub.2COOCH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.3 = H R.sup.4 = CH2COOCH.sub.3 R.sup.4 = C.sub.2H.sub.5 n = 2, m = 1 39 X.sup.1 = Cl X.sup.5 = CN X.sup.2 = Br X.sup.6 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.1 = H Y.sup.5 = H R.sup.2 = CH.sub.3 R.sup.3 = C.sub.2H.sub.4COOCH.sub.2COCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.4 = C.sub.2H.sub.5 Y.sup.3 = H n = 2 m = 1 40 X.sup.1 = Cl X.sup.5 = Cl X.sup.5 = CN X.sup.2 = Cl X.sup.6 = NO.sub.2 X.sup.6 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.1 = H Y.sup.5 = OCH.sub.3 Y.sup.5 = H R.sup.2 = CH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.4 = CH.sub.2COOCH.sub.3 R.sup.4 = C2H.sub.5 Y.sup.3 = H n = 2 m = 1 41 X.sup.1 = Cl X.sup.5 = CN X.sup.2 = Br X.sup.6 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.1 = H Y.sup.5 = H R.sup.2 = CH.sub.3 R.sup.3 = C.sub.2H.sub.4COOCH.sub.2COCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.4 = C.sub.2H.sub.5 Y.sup.3 = H n = 2 m = 1 42 X.sup.1 = Cl X.sup.5 = Cl X.sup.5 = CN X.sup.2 = Br X.sup.6 = NO.sub.2 X.sup.6 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 R.sup.1 = H Y.sup.5 = OCH.sub.3 Y.sup.5 = H R.sup.2 = CH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.4 = CH.sub.2COOCH.sub.3 R.sup.4 = C.sub.2H.sub.5 Y.sup.3 = H n = 2 m = 1 43 X.sup.1 = Cl X.sup.5 = Cl X.sup.2 = Br X.sup.6 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.1 = H Y.sup.5 = OCH.sub.3 R.sup.2 = CH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.4 = C.sub.2H.sub.5 Y.sup.3 = H n = 2 m = 1 44 X.sup.1 = Cl X.sup.2 = Br X.sup.3 = NO.sub.2 R.sup.1 = H R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2 m = 1 45 X.sup.1 = NO.sub.2 X.sup.2 = Br X.sup.3 = NO.sub.2 R.sup.1 = H R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2 m = 1 46 X.sup.1 = NO.sub.2 X.sup.5 = CN X.sup.2 = Cl X.sup.6 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.1 = H Y.sup.5 = OCH.sub.3 R.sup.2 = CH.sub.3 R.sup.3 = CH.sub.2COOCH.sub.3 Y.sup.1 = CH.sub.2-phenyl R.sup.4 = C.sub.2H.sub.5 Y.sup.3 = H n = 2 m = 1 Dye of Ratio Shade on Example Dye of formula (4) formula (5) (1):(2):(3):(3):(4)(5) Polyester 17 16:7:77::: Navy 18 X.sup.7 = NO.sub.2 10:10:::80: Navy R.sup.2 = C.sub.2H.sub.5 Y.sup.5 = OCH.sub.3 R.sup.5 = C2H4COOCH.sub.3 R.sup.6 = C2H4COOCH.sub.3 19 X.sup.7 = NO.sub.2 15:8:45::32: Navy R.sup.2 = C.sub.2H.sub.5 Y.sup.5 = OCH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 R.sup.6 = CH.sub.2COOCH.sub.3 20 (5a) 10:8:40:39::3 Navy X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H 21 X.sup.7 = NO.sub.2 (5b) 10:12:::72:6 Navy R.sup.2 = CH.sub.3 X.sup.8 = H Y.sup.5 = OCH.sub.3 R.sup.2 = C.sub.2H.sub.5 R.sup.5 = CH.sub.2COOCH.sub.3 Y.sup.6 = H R.sup.6 = CH.sub.2COOCH.sub.3 22 X.sup.7 = NO.sub.2 (5a) 10:10:51::25:4 Navy R.sup.2 = CH.sub.3 X.sup.8 = H Y.sup.5 = OCH.sub.3 R.sup.2 = C.sub.2H.sub.5 R.sup.5 = CH.sub.2COOCH.sub.3 Y.sup.6 = H R.sup.6 = C.sub.2H.sub.5 23 42:58:::: Brown 24 (5b) 35:40::::25 Brown X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H 25 65:35:::: Brown 26 (5a) 65:25::::10 Brown X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H 27 32:8:60::: Black 28 X.sup.7 = NO.sub.2 32:6:42::20: Black R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 R.sup.6 = C.sub.2H.sub.5 29 X.sup.7 = NO.sub.2 40:5:::55: Black R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 R.sup.6 = CH.sub.2COOCH.sub.3 30 (5a) 30:9:55:::6 Black X.sup.8 = H R.sup.2 = C.sub.3H.sub.7 Y.sup.6 = H 31 X.sup.7 = NO.sub.2 (5a) 32:6:32::23:7 Black R.sup.2 = CH.sub.3 X.sup.4 = H Y.sup.5 = OCH.sub.3 R.sup.3 = CH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 Y.sup.6 = H R.sup.6 = CH.sub.2-phenyl 32 18:5:77::: Navy 33 X.sup.7 = NO.sub.2 15:6:60::19: Navy R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 R.sup.6 = C.sub.2H.sub.5 34 X.sup.7 = NO.sub.2 13:5:::82: Navy R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 R.sup.6 = CH.sub.2-phenyl 35 (5a) 11:6:75:::8 Navy X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H 36 X.sup.7 = NO.sub.2 (5a) 11:7:65::12:5 Navy R.sup.2 = CH.sub.3 X.sup.4 = H Y.sup.5 = OCH.sub.3 R.sup.3 = C.sub.2H.sub.5 R.sup.5 = CH.sub.2COOCH.sub.3 Y.sup.6 = H R.sup.6 = C.sub.2H.sub.5 37 (5b) 18:17:32:25::8 Black X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H 38 (5b) 25:10:29:28::8 Black X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H 39 X.sup.7 = NO.sub.2 38::42::20: Black R.sup.2 = CH.sub.3 Y.sup.5 = OCH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 R.sup.6 = C.sub.2H.sub.5 40 43::29:28:: Black 41 X.sup.7 = NO.sub.2 (5b) 32::42::20:6 Black R.sup.2 = CH.sub.3 X.sup.8 = H Y.sup.5 = OCH.sub.3 R.sup.2 = CH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 Y.sup.6 = H R.sup.6 = C2H.sub.5 42 (5a) 35::29:28::8 Black X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H 43 (5a) 39::55:::6 Black X.sup.8 = H R.sup.2 = C.sub.3H.sub.7 Y.sup.6 = H 44 X.sup.7 = NO.sub.2 (5b) 13::::82:5 Navy R.sup.2 = CH.sub.3 X.sup.8 = H Y.sup.5 = OCH.sub.3 R.sup.2 = CH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 Y.sup.6 = H R.sup.6 = CH.sub.2-phenyl 45 X.sup.7 = NO.sub.2 (5b) 40:::;55:5 Black R.sup.2 = CH.sub.3 X.sup.8 = H Y.sup.5 = OCH.sub.3 R.sup.2 = CH.sub.3 R.sup.5 = CH.sub.2COOCH.sub.3 Y.sup.6 = H R.sup.6 = CH.sub.2COOCH.sub.3 46 (5a) 48::42:::10 Black X.sup.8 = H R.sup.2 = CH.sub.3 Y.sup.6 = H

(84) TABLE-US-00006 TABLE 2 1.sup.st Dye 2.sup.nd Dye Ratio Example of formula (1) of formula (1) Dye of formula (2) Dye of formula (5) (1):(1):(2):(5) Shade on Polyester 47 X.sup.1 = NO.sub.2 (5b) 70:::30 Brown X.sup.2 = H X.sup.8 = H X.sup.3 = NO.sub.2 R.sup.2 = C.sub.2H.sub.5 R.sup.1 = H R.sup.2 = C.sub.2H.sub.5 Y.sup.6 = H Y.sup.1 = C.sub.2H.sub.5 Y.sup.3 = H n = 2 m = 1 48 X.sup.1 = NO.sub.2 X.sup.4 = NO.sub.2 (5a) 30::33:37 Brown X.sup.2 = H Y.sup.2 = CH.sub.2-(p-Chloro- X.sup.8 = H X.sup.3 = NO.sub.2 phenyl) R.sup.2 = CH.sub.3 R.sup.1 = H R.sup.2 = C.sub.2H.sub.5 Y.sup.4 = C.sub.2H.sub.5 Y.sup.6 = H Y.sup.1 = C.sub.2H.sub.5 Y.sup.3 = H n = 2 m = 1 49 X.sup.1 = Cl X.sup.4 = NO.sub.2 77::23:: Yellowbrown X.sup.2 = Br Y.sup.2 = CH.sub.2-(p-methoxy- X.sup.3 = NO.sub.2 phenyl) R.sup.1 = H R.sup.2 = CH.sub.3 Y.sup.4 = CH.sub.3 Y.sup.1 = CH.sub.3 Y.sup.3 = H n = 2 m = 1 50 X.sup.1 = Br (5a) 87:::13 Yellowbrown X.sup.2 = Br X.sup.8 = H X.sup.3 = NO.sub.2 R.sup.2 = C.sub.2H.sub.5 R.sup.1 = H Y.sup.6 = H R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2 m = 1 51 X.sup.1 = Br X.sup.4 = NO.sub.2 (5b) 72::22:6 Yellowbrown X.sup.2 = Cl Y.sup.2 = CH.sub.2-phenyl X.sup.8 = H X.sup.3 = NO.sub.2 Y.sup.4 = C.sub.2H.sub.5 R.sup.2 = CH.sub.3 R.sup.1 = H Y.sup.6 = H R.sup.2 = C.sub.2H.sub.5 Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H n = 2 m = 1 52 X.sup.1 = CN X.sup.1 = Cl X.sup.4 = NO.sub.2 (5a) 18:26:21:35 Brown X.sup.2 = H X.sup.2 = Cl Y.sup.2 = CH.sub.2-phenyl X.sup.8 = H X.sup.3 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.4 = C.sub.2H.sub.5 R.sup.2 = CH.sub.3 R.sup.1 = H R.sup.1 = H Y.sup.6 = H R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H Y.sup.3 = H n = 2 n = 2 m = 1 m = 1 53 X.sup.1 = NO.sub.2 X.sup.1 = Cl X.sup.4 = NO.sub.2 (5b) 24:24:18:34 Brown X.sup.2 = H X.sup.2 = Br Y.sup.2 = CH.sub.2-phenyl X.sup.8 = H X.sup.3 = NO.sub.2 X.sup.3 = NO.sub.2 Y.sup.4 = CH.sub.3 R.sup.2 = C.sub.2H.sub.5 R.sup.1 = H R.sup.1 = H Y.sup.6 = H R.sup.2 = CH.sub.3 R.sup.2 = C.sub.2H.sub.5 Y.sup.1 = CH.sub.2-phenyl Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H Y.sup.3 = H n = 2 n = 2 m = 1 m = 1 54 X.sup.1 = CN X.sup.1 = Br (5b) 32:44::24 Brown X.sup.2 = H X.sup.2 = Br X.sup.8 = H X.sup.3 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.1 = H R.sup.1 = H Y.sup.6 = H R.sup.2 = C.sub.2H.sub.5 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H Y.sup.3 = H n = 2 n = 2 m = 1 m = 1 55 X.sup.1 = NO.sub.2 X.sup.1 = Br (5a) 30:42::28 Brown X.sup.2 = H X.sup.2 = Cl X.sup.8 = H X.sup.3 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = C.sub.3H.sub.7 R.sup.1 = H R.sup.1 = H Y.sup.6 = H R.sup.2 = CH.sub.3 R.sup.2 = C.sub.2H.sub.5 Y.sup.1 = CH.sub.2-phenyl Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H Y.sup.3 = H n = 2 n = 2 m = 1 m = 1 56 X.sup.1 = NO.sub.2 X.sup.1 = Cl (5b) 20:48::32 Brown X.sup.2 = Cl X.sup.2 = Cl X.sup.8 = H X.sup.3 = NO.sub.2 X.sup.3 = NO.sub.2 R.sup.2 = CH.sub.3 R.sup.1 = H R.sup.1 = H Y.sup.6 = H R.sup.2 = CH.sub.3 R.sup.2 = CH.sub.3 Y.sup.1 = CH.sub.2-phenyl Y.sup.1 = CH.sub.2-phenyl Y.sup.3 = H Y.sup.3 = H n = 2 n = 2 m = 1 m = 1