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US 7,723,494 B2Granted
Yellow anionic disazo dyes
AssigneeCiba Specialty Chemicals Corporation
InventorsMichael Lennartz, Adolf Käser, Sandra Weiss
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel yellow anionic dyes, a process for their preparation, certain novel intermediates necessary for their preparation and the use of these dyes for dyeing natural or synthetic materials, in particular, paper.
Claims9
A compound of the formula (13)
- in which
- R1 represents hydrogen, C1-C4alkyl, C4-C4alkoxy or SO3H,
- R2 represents SO3H or CO2H,
- R3 represents hydrogen, a C1-C4alkyl group, halogen, hydroxy, C1-C4alkoxy, carboxy, NH2 or NHC1-C4alkyl,
- R3a represents hydrogen or NH2 and
- A1 and A2, independently of the other, is selected from the group consisting of
- an acetoacetylated amine of the formula (2)
- in which
- X1 represents C1-C4alkyl, or phenyl which is unsubstituted or monosubstituted by C1-C4alkyl, C1-C4alkoxy or halogen and
- X2 represents phenyl which is di- or tri-substituted by one or two SO3H, SO2NHC1-C4alkyl groups which alkyl groups may be substituted, SO2C1-C4alkyl, C1-C4substituted or unsubstituted alkyl, hydroxy, C1-C4alkoxy, halogen, CF3, NH2, NHCOC1-C4alkyl, NHCOOC1-C4alkyl, NHCONHC1-C4alkyl, CO2H, CONHC1-C4alkyl or NO2;
- or X2 is phenyl which is mono-substituted by SO3H, SO2NHC1-C4 alkyl groups which alkyl groups may be substituted, SO2C1-C4alkyl, hydroxy, C1-C4alkoxy, CF3, NH2, NHCOC1-C4alkyl, NHCOOC1-C4alkyl, NHCONHC1-C4alkyl, CO2H, CONHC1-C4alkyl or NO2;
- or X2 is a 1- or 2-naphthyl residue which is unsubstituted or substituted by one or two SO3H, SO2NHC1-C4alkyl, carboxy, CONHC1-C4alkyl, carboxyC1-C4alkyl or carboxyaryl groups or a 5- or 6-membered heterocyclic ring containing 1-3 heteroatoms and which may be benzannelated and be further substituted by C1-C4alkyl, C1-C4alkoxy or halogen and which may be attached to the NH-atom in formula (2) either via the hetero- or benzo-nucleus, in the case of benzannelated heterocycles;
- a derivative of barbituric acid of the formula (3)
- in which
- Y represents O, NCN or NCONH2;
- a 2,4,6-triaminopyrimidine derivative;
- a pyridone derivative of the formula (4)
- in which
- Q1 represents hydrogen, hydroxy, C1-C2alkyl, hydroxyethyl, 2-(C1-C2alkoxy)alkyl, C1-C2alkoxy, COOH, CONH2 or COOC1-C2alkyl,
- Q2 represents hydrogen, CN, CONH2, halogen, SO3H or C1-C2alkyl which is unsubstituted or substituted by hydroxy, phenyl or SO3H,
- Q3 represents hydrogen, phenyl, C1-C2alkylphenyl, cyclohexyl or C1-C4alkyl which is unsubstituted or substituted by hydroxy, CN, C1-C2alkoxy or SO3H and
- Q4 represents hydrogen or hydroxy;
- an aminopyrazole or a pyrazolone derivative of formula (5), (6), (7) or (8)
- in which
- R4 represents hydrogen, substituted or unsubstituted C1-C4alkyl, C2-C4alkenyl, NHCOC1-C4alkyl or CO2H,
- R5 represents hydrogen, halogen, C1-C4alkyl, SO3H or CO2H,
- R6 represents halogen, C1-C4alkyl, SO3H or CO2H in formula (5) and represents halogen, SO3H or CO2H in formula (7);
- and
- R7 represents hydrogen or C1-C4alkyl;
- and
- a benzoic acid derivative of formula (9) or (10)
- in which
- R7 represents hydrogen or C1-C4alkyl and
- R8 represents hydrogen or hydroxy, or
- A1 and A2, each one independently of the other, represent a phenol residue of the formula (11) or (12)
- in which
- R9 and R10, each one independently of the other, represent hydrogen, C1-C4alkyl, C1-C4alkoxy, hydroxy, halogen, NH2, NHCOC1-C4alkyl, NO2, SO3H, CO2C1-C4alkyl or CONHC1-C4alkyl groups,
- with the proviso that in the compounds of formula (13), if
- R1, R2, R3 and R3a each, independently of the others, are hydrogen or SO3H, then
- A1 and A2 are not both a 1-phenyl or 1-sulphophenyl-3-methyl-5-aminopyrazole residue, or, if
- R1, R3 and R3a are hydrogen and R2 is SO3H and one of
- A1 and A2 represents a 1-sulphophenyl-3-methyl pyrazol-5-one residue, then the other is not a residue of formula (11) in which both
- R9 and R10 are hydrogen, or if
- A1 represents a 1-nitrophenyl-, a 1-phenyl- or an unsubstituted 3-methyl pyrazol-5-one residue,
- A2 is not a residue of formula (9) in which R7 represents hydrogen, or if
- R1, R3 and R3a represent hydrogen, R2 is CO2H and
- A1 represents a residue of formula (9), in which R7 is hydrogen,
- A2 is not a residue of formula (2) or formula (7).
45 more elements
Dependencies are inferred from the claim text.