Black trisazo metal complex dyes
First Claim
1. A metal complex of a trisazo dye of the general formula (4) whereR1 is aryl substituted by one or more substituents selected from the group consisting of OH, O(C1-C6)-alkyl, O (C1-C6)-alkyl-COOM, O(C1-C6)-alkyl-SO3M, O(hydroxy(C1-C6)-alkyl), (C1-C6)-alkyl, COOM, SO3M, SO2NH2, SO2N(hydroxy(C1-C6)-alkyl)2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, NH2, NH(C1-C6)-alkyl, NHacyl, NHaryl, N(hydroxy(C1-C6)-alkyl)2, N((C1-C6)-alkyl)2 and halogen;
- R2 is OH, O(C1-C6)-alkyl, COOM or SO3M;
R3, R4 and R5 are identical or different and are each selected from the group consisting of H, OH, O(C1-C6)-alkyl, O(C1-C6)-alkyl-COOM, O(C1-C6)-alkyl-SO2M, O(hydroxy(C1-C6)-alkyl), (C1-C6)-alkyl, COOM, SO3M, SO2NH2, SO2N(hydroxy(C1-C6)-alkyl)2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, NH2, NH(C1-C6)-alkyl, NHacyl, NHaryl, N(hydroxy(C1-C6)-alkyl)2, N((C1-C6)-alky)2, and halogen, R6 is a heterocyclic aromatic which is unsubstituted or substituted by one or more substituents selected from the group consisting of OH, O(C1-C6)-alkyl, O(C1-C6)-alkyl-COOM, O(C1-C6)-alkyl-SO3M, O(hydroxy(C1-C6)-alkyl), (C1-C6)-alkyl, COOM, SO3M, SO2NH2, CONH-phenyl, SO2NH-phenyl, SO2N(hydroxy(C1-C6)-alkyl)2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, NH2, NH(C1-C6)-alkyl, NHacyl, NHaryl, N(hydroxy(C1-C6)-alkyl)2, N((C1-C6)-alkyl)2, halogen and phenylsulfo, or is a similarly substituted pyrazole or pyridone radical; and
M is hydrogen, a monovalent metal cation, one equivalent of a polyvalent metal cation or an unsubstituted or alkyl-, alkoxyalkyl- or hydroxyalkyl-substituted ammonium ion.
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Accused Products
Abstract
Disclosed are metal complexes of trisazo dyes of the general formula 4
wherein R1 through R6 are as defined in the specification. The dyes are useful for dyeing and printing natural and synthetic fiber materials, recording fluids, especially for the inkjet process, liquid formulations for paper pulp dyeing, and also as colorants for electrophotographic toners, powder coatings and color filters including the dyes of the invention.
43 Citations
14 Claims
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1. A metal complex of a trisazo dye of the general formula (4)
where R1 is aryl substituted by one or more substituents selected from the group consisting of OH, O(C1-C6)-alkyl, O (C1-C6)-alkyl-COOM, O(C1-C6)-alkyl-SO3M, O(hydroxy(C1-C6)-alkyl), (C1-C6)-alkyl, COOM, SO3M, SO2NH2, SO2N(hydroxy(C1-C6)-alkyl)2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, NH2, NH(C1-C6)-alkyl, NHacyl, NHaryl, N(hydroxy(C1-C6)-alkyl)2, N((C1-C6)-alkyl)2 and halogen; -
R2 is OH, O(C1-C6)-alkyl, COOM or SO3M;
R3, R4 and R5 are identical or different and are each selected from the group consisting of H, OH, O(C1-C6)-alkyl, O(C1-C6)-alkyl-COOM, O(C1-C6)-alkyl-SO2M, O(hydroxy(C1-C6)-alkyl), (C1-C6)-alkyl, COOM, SO3M, SO2NH2, SO2N(hydroxy(C1-C6)-alkyl)2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, NH2, NH(C1-C6)-alkyl, NHacyl, NHaryl, N(hydroxy(C1-C6)-alkyl)2, N((C1-C6)-alky)2, and halogen, R6 is a heterocyclic aromatic which is unsubstituted or substituted by one or more substituents selected from the group consisting of OH, O(C1-C6)-alkyl, O(C1-C6)-alkyl-COOM, O(C1-C6)-alkyl-SO3M, O(hydroxy(C1-C6)-alkyl), (C1-C6)-alkyl, COOM, SO3M, SO2NH2, CONH-phenyl, SO2NH-phenyl, SO2N(hydroxy(C1-C6)-alkyl)2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, NH2, NH(C1-C6)-alkyl, NHacyl, NHaryl, N(hydroxy(C1-C6)-alkyl)2, N((C1-C6)-alkyl)2, halogen and phenylsulfo, or is a similarly substituted pyrazole or pyridone radical; and
M is hydrogen, a monovalent metal cation, one equivalent of a polyvalent metal cation or an unsubstituted or alkyl-, alkoxyalkyl- or hydroxyalkyl-substituted ammonium ion.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14)
where M1 is Al, Cr, Fe, Co, Ni or Cu, R20 is C1-C6-alkyl, n is 0 or 1, and X is a chemical bond, — - CO—
or —
SO2—
.
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9. A process for preparing a metal complex of a trisazo dye as claimed in claim 1, which comprises diazotizing a naphtholamine of the formula (14)
to give a diazonium salt, coupling said diazonium salt with a compound of the formula (15) -
10. A method for dyeing and printing natural or synthetic fiber materials, paper, electrophotographic toners, recording fluids and powder coating comprising the step of adding a metal complex of a disazo dye as claimed in claim 1 to said fiber material, paper, a binder for an electrophotographic toner or powder coating, or to a base of a recording fluid.
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11. A recording fluid comprising one or more metal complex dyes as claimed in claim 1.
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12. A recording fluid as claimed in claim 11, including 0.1 to 50% by weight of one or more of the metal complex dyes, 0 to 99% by weight of water and 0.5 to 99.5% by weight of organic solvents, humectants or a combination thereof.
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13. A recording fluid as claimed in claim 11, including 0.5 to 15% by weight of one or more of the metal complex dyes, 35 to 75% by weight of water and 10 to 50% by weight of organic solvents, humectants or a combination thereof.
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14. A recording fluid as claimed in claim 11, including 0.5 to 15% by weight of one or more of the metal complex dyes, 0 to 20% by weight of water and 70 to 99.5% by weight of organic solvents, humectants or a combination thereof.
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Specification