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US 10,259,942 B2Granted
Black trisazo dyes, their preparation and their use
AssigneeDFI Chem GmbH
InventorsKurt Baettig, Damien Moigno
Life of this patent
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Abstract
The present invention provides trisazo dyes of formula (V), wherein A, M and R1, R2, R3, R4 are as defined in the specification, processes for their preparation, recording liquids and liquid dye preparations containing them and their use in inks as well as processes for applying them and printed articles comprising them.
Claims19
A trisazo dye of general formula (V):
- where
- M is selected from the group consisting of H, a metal cation, an ammonium cation N(HkR5m),
- wherein
- each R5 is selected from the group consisting of —H, an substituted or unsubstituted, saturated or unsaturated aliphatic group having 1 to 18 carbon atoms, and
- k is an integer selected from 0, 1, 2, 3, 4 and
- m=4−k,
- where
- R1, R2 independently represent a hydrogen atom, a SO3M group, a COOM group, a halogen atom, a NO2 group, an ester group, an alkyl- or alkoxy group each having from 1 to 6 carbon atoms, an unsubstituted or substituted amide or sulfonamide group or sulfone group each having up to 12 carbon atoms, wherein the substituents are selected from the group consisting of COOM, OH, OCH3, NH2, Cl, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM,
- where
- R3, R4 independently represent a hydrogen atom, an alkyl- or alkoxy group each having from 1 to 6 carbon atoms, an unsubstituted or substituted amide or sulfonamide group each having up to 6 carbon atoms, wherein the substituents are selected from the group consisting of COOM, OH, OCH3, NH2, Cl, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM,
- where
- either A represents a moiety of general formula (VI):
- wherein
- R6, R7, R8, R9, R10 independently represent a hydrogen atom, a SO3M group, a NO2 group, a nitrile group, an amino group, a COOM group, a halogen atom, an ester group, an alkyl or alkoxy group each having from 1 to 2 carbon atoms, an unsubstituted or substituted amide or sulfonamide group or sulfone group each having up to 6 carbon atoms, wherein the substituents are selected from the group consisting of COOM, Cl, OH, OCH3, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM;
- or A represents a moiety of general formula (VII):
- wherein
- o is 0 or 1
- and
- R11, R12, R13, R14 independently represent a hydrogen atom, a SO3M group, a NO2 group, a COOM group, an unsubstituted or substituted amide or sulfonamide group having up to 6 carbon atom, wherein the substituents are selected from the group consisting of COOM, OH, OCH3, NH2, Cl, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM.
16 more elements
A method of preparation of a trisazo dye according to general formula (V)
- wherein
- an amine of general formula (VIII)
- where R1 and R2 independently represent a hydrogen atom, a SO3M group, a COOM group, a halogen atom, a NO2 group, an ester group, an alkyl- or alkoxy group each having from 1 to 6 carbon atoms, an unsubstituted or substituted amide or sulfonamide group or sulfone group each having up to 12 carbon atoms, wherein the substituents are selected from the group consisting of COOM, OH, OCH3, NH2, Cl, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM,
- is diazotized and subsequently coupled with a compound of general formula (IX),
- where R3 and R4 independently represent a hydrogen atom, an alkyl- or alkoxy group each having from 1 to 6 carbon atoms, an unsubstituted or substituted amide or sulfonamide group each having up to 6 carbon atoms, wherein the substituents are selected from the group consisting of COOM, OH, OCH3, NH2, Cl, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM,
- at an acid value of pH situated between 1.0 and 3.0, under formation of the intermediate dye of general formula (X),
- wherein the intermediate dye of general formula (X) is diazotized and subsequently coupled with K-Acid at an acid value of pH situated between 0.5 and 2.0 under formation of the intermediate dye of general formula (XII),
- wherein
- M is the cation of the base used during the coupling reaction to maintain the pH value at the defined pH range,
- wherein the intermediate dye of general formula (XII) is subsequently coupled with a diazonium compound of general formula (XIII)
- where R6, R7, R8, R9 and R10 independently represent a hydrogen atom, a SO3M group, a NO2 group, a nitrile group, an amino group, a COOM group, a halogen atom, an ester group, an alkyl or alkoxy group each having from 1 to 2 carbon atoms, an unsubstituted or substituted amide or sulfonamide group or sulfone group each having up to 6 carbon atoms, wherein the substituents are selected from the group consisting of COOM, Cl, OH, OCH3, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM and X is the anion of the acid used during the diazotization,
- or of general formula (XIV)
- where o is 0 or 1, R11, R12, R13 and R14 independently represent a hydrogen atom, a SO3M group, a NO2 group, a COOM group, an unsubstituted or substituted amide or sulfonamide group having up to 6 carbon atom, wherein the substituents are selected from the group consisting of COOM, OH, OCH3, NH2, Cl, COOCH3, COOCH2CH3, CH3, CH2CH2COOM, (CH2)3COOM and CH2OCH2COOM and X is the anion of the acid used during the diazotization,
- at a more or less neutral value of pH situated between about 5.0 and 9.0 yielding the dye of general formula (V).
11 more elements
Dependencies are inferred from the claim text.