IP Library Granted Patent US 7,699,898
Granted Patent B2
US 7,699,898 · App. 11/908,981 · Granted Apr 20, 2010

Metal complex dye mixtures

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Quick Facts
Patent No.
US 7,699,898
App. No.
11/908,981
Granted
Apr 20, 2010
Kind
B2
Abstract

Dye mixtures comprising one or more, such as two or three, preferably 1 or 2, dyes of the formula (1) and at least 2 dyes of the formula (2) in which Me, M, n, and V 1 to V 11 are as defined in claim 1 , their preparation, and their use for dyeing and printing hydroxyl- and carboxamido-containing material.

Claims (55)

1. A dye mixture which comprises one or more dyes of the formula (1)

and at least one dye of the formula (2)

in which

Me is Cr (3+) or Co (2+) ,

M is hydrogen, an alkali metal, or the equivalent of an alkaline earth metal,

n is 1 or 2

V 1 to V 8 are independently of one another and are hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkoxy, halogen, nitro, sulfo, sulfamoyl, N—C 1-4 -alkylsulfamoyl, N—C 1-4 -dialkylsulfamoyl or N—C 1-2 -alkoxy-C 1-2 -alkylsulfamoyl,

V 9 and V 10 are independently of one another and are phenyl, C 1 -C 4 -alkylphenyl, nitrophenyl, sulfophenyl, N—C 1-4 -alkylsulfamoylphenyl, halophenyl, cyanophenyl, or sulfamoylphenyl,

V 11 is hydrogen, phenyl, C 1 -C 4 -alkylphenyl, nitrophenyl, sulfophenyl, N—C 1-4 -alkylsulfamoylphenyl, halophenyl or cyanophenyl,

and, if V 11 is not hydrogen, at least one of the radicals V 7 or V 8 is N—C 1-4 -dialkyl-sulfamoyl.

2. The dye mixture as claimed in claim 1 , comprising at least one dye of the formula (1a)

and also at least one dye of the formula (2b)

wherein

Me is Cr (3+) or Co (2+) ,

M is hydrogen, an alkali metal, or the equivalent of an alkaline earth metal,

n is 1 or 2,

V 1 to V 6 are independently of one another hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkoxy, halogen, nitro, sulfo, sulfamoyl, N—C 1-4 -alkylsulfamoyl, N—C 1-4 -dialkylsulfamoyl or N—C 1-2 -alkoxy-C 1-2 -alkylsulfamoyl,

V 9 and V 10 are independently of one another phenyl, C 1 -C 4 -alkylphenyl, nitrophenyl, sulfophenyl, N—C 1-4 -alkylsulfamoylphenyl, halophenyl or cyanophenyl.

3. The dye mixture as claimed in claim 1 , comprising at least one dye of the formula (1b), at least one dye of the formula (2a), and at least one dye of the formula (2b)

in which V 1 to V 6 and V 9 and V 10 are as defined in claim 1 .

4. The dye mixture as claimed in claim 1 , comprising dyes of the formula (1) and dyes of the formula (2) in a molar ratio of dye or dyes (1) to dye or dyes (2) of 95:5 to 5:95.

5. The dye mixture as claimed in claim 1 , comprising dyes of the formula (1) and dyes of the formula (2) in a molar ratio of dye or dyes (1) to dye or dyes (2) of 80:20 to 40:60.

6. A process for preparing a dye mixture which comprises one or more dyes of the formula (1)

and at least one dye of the formula (2)

in which

Me is Cr (3+) or Co (2+) ,

M is hydrogen, an alkali metal, or the equivalent of an alkaline earth metal,

n is 1or 2

V 8 to are independently of one another and are hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkoxy, halogen, nitro, sulfo, sulfamoyl, N—C 1-4 -alkylsulfamoyl, N—C 1-4 -dialkylsulfamoyl or N—C 1-2 -alkoxy-C 1-2 -alkylsulfamoyl,

V 9 and V 10 are independently of one another and are phenyl, C 1 -C 4 -alkylphenyl, nitrophenyl, sulfophenyl, N—C 1-4 -alkylsulfamoylphenyl, halophenyl, cyanophenyl, preferably or sulfamoylphenyl,

V 11 is hydrogen, phenyl, C 1 -C 4 -alkylphenyl, nitrophenyl, sulfophenyl, N—C 1-4 -alkylsulfamoylphenyl, halophenyl or cyanophenyl,

and, if V 11 is not hydrogen, at least one of the radicals V 7 or V 8 is N—C 1-4 -dialkylsulfamoyl,

which comprises mechanical mixing of the individual dyes, whether in the form of their powders or granules or their synthesis solution or of aqueous solutions of the individual dyes.

7. A process for dyeing or printing material which comprises contacting the material with a dye mixture, wherein the dye mixture comprises one or more dyes of the formula (1)

and at least one dye of the formula (2)

in which

Me is Cr (3+) or Co (2+) ,

M is hydrogen, an alkali metal, or the equivalent of an alkaline earth metal,

n is 1or 2

V 1 to V 8 are independently of one another and are hydrogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkoxy, halogen, nitro, sulfo, sulfamoyl, N—C 1-4 -alkylsulfamoyl, N—C 1-4 -dialkylsulfamoyl or N—C 1-2 -alkoxy-C 1-2 -alkylsulfamoyl,

V 9 and V 10 are independently of one another and are phenyl, C 1 -C 4 -alkylphenyl, nitrophenyl, sulfophenyl, N—C 1-4 -alkylsulfamoylphenyl, halophenyl, cyanophenyl, preferably or sulfamoylphenyl,

V 11 is hydrogen, phenyl, C 1 -C 4 -alkylphenyl, nitrophenyl, sulfophenyl, N—C 1-4 -alkylsulfamoylphenyl, halophenyl or cyanophenyl, and, if V 11 is not hydrogen, at least one of the radicals V 7 or V 8 is N—C 1-4 -dialkylsulfamoyl.

8. The process as claimed in claim 7 , wherein the material is hydroxyl- and carboxamido-containing material.

9. The process as claimed in claim 7 , wherein the material is a natural or synthetic polyamide fiber material.

10. The process as claimed in claim 9 , wherein the process is for the single-bath on-tone dyeing of blends of natural and synthetic polyamide fiber materials.

11. The dye mixture as claimed in claim 1 , which further comprises a blue-dyeing acid dye, a black-dyeing acid dye, a yellow-dyeing acid dye or an orange-dyeing acid dye.

12. The dye mixture as claimed in claim 1 , which further comprises at least one of the following CI dyes: Acid Blue 170, 171, 199, 200, 229, 317, 284, 296, 334, 335, Acid Black 058, 060, 061, 063, 099, 107, 131, 132, 140, 207, 218, 220, 222, 244, Acid Yellow 059, 116, 119, 137, 151, 155, 177, 182, 220, 232, 235, Acid Orange 060, 080, 086, 088, 107, 108, 117, 130, 144, 154, 162, 166, and 168.

13. The dye mixture as claimed in claim 1 , wherein

M is hydrogen, sodium, potassium or lithium,

V 1 to V 8 are independently of one another nitro, sulfo or dimethylsulfamoyl and

V 11 is phenyl or C 1 -C 4 -alkylphenyl.

14. The dye mixture as claimed in claim 2 , wherein

M is hydrogen, sodium, potassium or lithium,

V 1 to V 6 are independently of one another and are nitro, sulfo, or dimethylsulfamoyl,

V 9 and V 10 are independently of one another are phenyl and C 1 -C 4 -alkylphenyl or sulfamoylphenyl.

Assignments (3)
MERGER Recorded Jun 26, 2012
From: DYSTAR COLOURS DEUTSCHLAND GMBH
To: DYSTAR COLOURS DISTRIBUTION GMBH
Reel/Frame 028440/0305 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2010
From: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG
To: DYSTAR COLOURS DEUTSCHLAND GMBH
Reel/Frame 025204/0348 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2007
From: RUCHSER, THOMAS; STEINAU, OLIVER; GIEHL, ANDREAS
To: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG
Reel/Frame 019998/0598 →