Claims
- 1. A compound of the formula ##STR301## or a salt thereof, wherein Da is ##STR302## wherein R.sub.6 is hydrogen or sulfo,
- R.sub.7 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or (C.sub.1-4 alkyl)carbonylamino,
- x is 0 or 1, and
- y is 1 or 2,
- Kb is ##STR303## wherein Q.sub.1a is hydrogen; cyano; amino; hydroxy; methyl; ethyl; 2-hydroxyethyl; 2-(C.sub.1-2 alkoxy)ethyl; methoxy; ethoxy; cyclohexyl; phenyl; phenyl substituted by 1 or 2 substituents selected from methyl, methoxy, chloro, carboxy and sulfo; phenyl(C.sub.1-2 alkyl); phenyl(C.sub.1-2 alkyl) the phenyl group of which is substituted by 1 or 2 substituents selected from methyl, methoxy, chloro, carboxy and sulfo; pyridiniummethyl; --CO--R.sub.10a or --(CH.sub.2).sub.r --R.sub.11a, wherein
- R.sub.10a is hydroxy, amino, methoxy or ethoxy,
- R.sub.11a is cyano, chloro, sulfo, --O--SO.sub.3 H, pyridyl or --CO--R.sub.12a, wherein R.sub.12a is hydroxy, amino, methyl, ethyl, methoxy or ethoxy, and
- Q.sub.2a is hydrogen; cyano; chloro; sulfo; --NR.sub.13b R.sub.14b ; methyl; ethyl; C.sub.1-2 alkyl monosubstituted by hydroxy, phenyl, sulfo or --O--SO.sub.3 H; --CO--R.sub.15a ; --CH.sub.2 --NHCO--R.sub.16a --E.sub.1b ; pyridinium; pyrimidinium,; benzoimidazolium; or pyridinium, pyrimidinium or benzoimidazolium monosubstituted by methyl, amino, methylamino or dimethylamino, wherein
- E.sub.1b is hydrogen, chloro, --NR.sub.23a R.sub.24a, --N.sup..sym. R.sub.25a R.sub.26a R.sub.27a or sulfo,
- each of R.sub.13b and R.sub.14b is independently hydrogen, methyl or --CO--R.sub.16a --E.sub.1b, wherein E.sub.1b is as defined above, and
- R.sub.15a is hydroxy, amino methylamino, dimethylamino, methyl, ethyl, methoxy or ethoxy, or
- Q.sub.1a and Q.sub.2a taken together are --CH.sub.2 --Y.sub.3 --CH.sub.2 --, wherein Y.sub.3 is --(CH.sub.2).sub.r --, ##STR304## and the * denotes the carbon atom attached to the --CH.sub.2 -- radical in the Q.sub.1a -position,
- Q.sub.3a is hydrogen; --NR.sub.18a R.sub.19a ; phenyl; phenyl(C.sub.1-2 alkyl); cyclohexyl; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by hydroxy, cyano, C.sub.1-2 alkoxy, --CO--R.sub.20a, sulfo or --O--SO.sub.3 H; --R.sub.16b --E.sub.2a ; ##STR305## wherein E.sub.2a is --NR.sub.23 R.sub.24, --NR.sup..sym. R.sub.25 R.sub.26 R.sub.27 ##STR306## wherein each R.sub.22a is independently chloro or --N(R.sub.30).sub.2,
- R.sub.16b is linear or branched C.sub.1-3 alkylene,
- each of R.sub.18a and R.sub.19a is independently hydrogen, methyl, ethyl or phenyl,
- R.sub.20a is hydroxy, methoxy or ethoxy, and
- R.sub.21a is --NR.sub.23 R.sub.24, --N.sup..sym. R.sub.25 R.sub.26 R.sub.27, --NHCO--R.sub.16a --NR.sub.23 R.sub.24, --NHCO--R.sub.16a --N.sup..sym. R.sub.25 R.sub.26 R.sub.27, --SO.sub.2 NH--R.sub.16a --NR.sub.23 R.sub.24, --SO.sub.2 NH--R.sub.16a --N.sup..sym. R.sub.25 R.sub.26 R.sub.27, --CONH--R.sub.16a --NR.sub.23 R.sub.24 or --CONH--R.sub.16a --N.sup..sym. R.sub.25 R.sub.26 R.sub.27,
- Q.sub.4 is hydrogen or hydroxy, with the proviso that Q.sub.4 is hydrogen when Q.sub.1a is hydroxy,
- R.sub.8b is methyl, carboxy or --CONH.sub.2,
- R.sub.9a is hydrogen, methyl, phenyl or phenyl substituted by 1 or 2 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, chloro, acetamido, --NHCO--R.sub.16 --NR.sub.23 R.sub.24, --NHCO--R.sub.16 --N.sup..sym. R.sub.25 R.sub.26 R.sub.27, --SO.sub.2 NH--R.sub.16 --NR.sub.23 R.sub.24, --SO.sub.2 NH--R.sub.16 --N.sup..sym. R.sub.25 R.sub.26 R.sub.27, carboxy and sulfo, wherein R.sub.16 is linear or branched C.sub.1-6 alkylene,
- Y.sub.1 is hydroxy or amino, and
- Y.sub.2a is .dbd.O, .dbd.S, .dbd.NH, .dbd.NCN or .dbd.NCONH.sub.2,
- R.sub.1x is hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, chloro, cyano, carboxy or sulfo,
- each of R.sub.2x and R.sub.3x is independently hydrogen, halo, C.sub.1-4 alkyl, sulfo(C.sub.1-4 alkyl), --(CH.sub.2).sub.t --NR.sub.23a R.sub.24a, --(CH.sub.2).sub.t --N.sup..sym. R.sub.25a R.sub.26a R.sub.27a, C.sub.1-4 alkoxy, sulfo(C.sub.1-4 alkoxy), --NHCO--R.sub.5x, --NR.sub.23a R.sub.24a, --N.sup..sym. R.sub.25a R.sub.26a R.sub.27a or sulfo, wherein R.sub.5x is C.sub.1-4 alkyl, --(CH.sub.2).sub.t --NR.sub.23a R.sub.24a, --(CH.sub.2).sub.t --N.sup..sym. R.sub.25a R.sub.26a R.sub.27a, C.sub.1-4 alkoxy or amino, with the proviso that R.sub.2x is other than sulfo,
- R.sub.4x is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, nitro or sulfo, and
- Xa is --CO--, --CH.sub.2 --, --SO.sub.2 --, --CONR.sub.1x -- or ##STR307## wherein Y.sub.x is hydroxy, C.sub.1-4 alkoxy, phenoxy, amino, C.sub.1-2 alkylamino, C.sub.2-4 hydroxyalkylamino, N,N-di-(C.sub.2-4 hydroxyalkyl)amino, --NH--(CH.sub.2).sub.m --SO.sub.3 H, anilino, morpholino, piperidino, piperazino or N-methylpiperazino, wherein m is 2 or 3, and
- R.sub.1x is as defined above,
- wherein
- each R.sub.1b is independently hydrogen, methyl or ethyl,
- each R.sub.16a is independently C.sub.1-2 alkylene,
- each R.sub.23 and R.sub.24 is independently hydrogen, C.sub.1-2 alkyl, n-C.sub.2-3 hydroxyalkyl or benzyl, or
- --NR.sub.23 R.sub.24 is pyrrolidino, piperidino, morpholino, piperazino or N-methylpiperazino,
- each R.sub.23a and R.sub.24a is independently hydrogen, methyl or ethyl, or
- --NR.sub.23a R.sub.24a is piperidino, morpholino, piperazino or N-methylpiperazino,
- each R.sub.25 and R.sub.26 is independently C.sub.1-2 alkyl, n-C.sub.2-3 hydroxyalkyl or benzyl, and
- each R.sub.27 is independently methyl, ethyl or benzyl, or
- --N.sup..sym. R.sub.25 R.sub.26 R.sub.27 is pyridinium, pyridinium monosubstituted or disubtituted by methyl or ##STR308## wherein Z is a direct bond, --CH.sub.2 --, --O--, --NH-- or --N(CH.sub.3)--, and
- R.sub.27 is as defined above,
- each R.sub.25a, R.sub.26a and R.sub.27a is independently methyl or ethyl, or
- --N.sup..sym. R.sub.25a R.sub.26a R.sub.27a is pyridinium, pyridinium monosubstituted or disubstituted by methyl or ##STR309## wherein Z' is --CH.sub.2 --, --O--, --NH-- or --N(CH.sub.3)--, and
- R.sub.27a is as defined above,
- each R.sub.30 is independently hydrogen, C.sub.1-2 alkyl or C.sub.1-2 alkyl monosubstituted by hydroxy, cyano or C.sub.1-2 alkoxy,
- each r is independently 1 or 2,
- each t is independently 1, 2 or 3, and
- each halo is independently fluoro, chloro or bromo,
- with the provisos that the compound contains 1, 2, 3 or 4 sulfo groups, the total number of sulfo and carboxy groups equals or exceeds the total number of basic and cationic groups, and the positive charge of each cationic group independently is balanced by the negative charge of an --SO.sub.3.sup..crclbar. or --COO.sup..crclbar. group of the molecule or of a non-chromophoric anion, or a mixture of such compounds each of which is in free acid or salt form.
- 2. A compound according to claim 1, or a salt thereof.
- 3. A compound according to claim 2, or a salt thereof, wherein Xa is --CO--, --CH.sub.2 --, --CO--NR.sub.1a -- or ##STR310## wherein R.sub.1a is hydrogen, methyl, ethyl or C.sub.1-3 alkyl monosubstituted by hydroxy, chloro, cyano, carboxy or sulfo, and
- Y.sub.ax is hydroxy, methoxy, amino, C.sub.1-2 -alkylamino, C.sub.2-4 hydroxyalkylamino, N,N-di-(C.sub.2-4 hydroxyalkyl)amino, --NH--(CH.sub.2).sub.m --SO.sub.3 H, anilino, morpholino, piperidino, piperazino or N-methylpiperazino, wherein m is 2 or 3.
- 4. A compound according to claim 2, or a salt thereof, wherein Xa is --CO--, --SO.sub.2 -- or ##STR311## wherein Y.sub.ax is hydroxy, methoxy, amino, C.sub.1-2 alkylamino, C.sub.2-4 hydroxyalkylamino, N,N-di-(C.sub.2-4 hydroxyalkyl)amino, --NH--(CH.sub.2).sub.m --SO.sub.3 H, anilino, morpholino, piperidino, piperazino or N-methylpiperazino, wherein m is 2 or 3.
- 5. A compound according to claim 2, or a salt thereof, wherein each R.sub.1x is independently hydrogen, methyl, ethyl or C.sub.1-3 alkyl monosubstituted by hydroxy, chloro, cyano, carboxy or sulfo.
- 6. A compound according to claim 2, or a salt thereof, wherein
- R.sub.2x is in the 6-position of Ring A, and
- R.sub.3x is in the 3-position of Ring A.
- 7. A compound according to claim 6, or a salt thereof, wherein
- R.sub.2x is hydrogen, methyl, methoxy, acetamido or --NHCONH.sub.2, and
- R.sub.3x is hydrogen, methyl or methoxy.
- 8. A compound according to claim 2, or a salt thereof, wherein the Kb--N.dbd.N-- group is in the 3- or 4-position of Ring B.
- 9. A compound according to claim 2, or a salt thereof, wherein Da is 4,8-disulfonaphthyl-2, 6,8-disulfonaphthyl-2 or ##STR312## wherein R.sub.7b is hydrogen, methyl or methoxy, and Xa is --CO-- or ##STR313## wherein Y.sub.ax is hydroxy, methoxy, amino, C.sub.1-2 -alkylamino, C.sub.2-4 hydroxyalkylamino, N,N-di(C.sub.2-4 hydroxyalkyl)amino, --NH--(CH.sub.2).sub.m --SO.sub.3 H, anilino, morpholino, piperidino, piperazino, or N-methylpiperazino, wherein m is 2 or 3.
- 10. A compound according to claim 1, or a salt thereof, wherein Kb is ##STR314## or a mixture of such compounds each of which is in free acid or salt form.
- 11. A compound according to claim 1, or a salt thereof.
- 12. A compound according to claim 11, or a salt thereof, wherein the Kb--N.dbd.N-- group is in the 3- or 4-position of Ring B.
- 13. A compound according to claim 12, or a salt thereof, wherein Xa is --CO--, --CH.sub.2 --, --CONR.sub.1a -- or ##STR315## wherein R.sub.1a is hydrogen, methyl, ethyl or C.sub.1-3 alkyl monosubstituted by hydroxy, chloro, cyano, carboxy or sulfo, and Y.sub.ax is hydroxy, methoxy, amino, C.sub.1-2 -alkylamino, C.sub.2-4 hydroxyalkylamino, N,N-di-(C.sub.2-4 hydroxyalkyl)amino, --NH (CH.sub.2).sub.m --SO.sub.3 H, anilino, morpholino, piperidino, piperazino or N-methylpiperazino, wherein m is 2 or 3.
- 14. A compound according to claim 11, or a salt thereof, wherein
- each R.sub.1x is independently hydrogen, methyl, ethyl or C.sub.1-3 alkyl monosubstituted by hydroxy, chloro, cyano, carboxy or sulfo,
- R.sub.2x is hydrogen, chloro, methyl, methoxy, --NHCO--R.sub.5a, --(CH.sub.2).sub.t --SO.sub.3 H, --O--(CH.sub.2).sub.3 --SO.sub.3 H, --(CH.sub.2).sub.t --NR.sub.23a R.sub.24 a or --(CH.sub.2).sub.t --N.sup..sym. R.sub.25a R.sub.26a R.sub.27 a, wherein R.sub.5a is methyl, methoxy, amino, --(CH.sub.2).sub.t --NR.sub.23a R.sub.24a or --(CH.sub.2).sub.t --N.sup..sym. R.sub.25a R.sub.26a R.sub.27a,
- R.sub.3x is hydrogen, methyl or methoxy, and
- Y.sub.x is hydroxy, methoxy, amino, C.sub.1-2 alkylamino, C.sub.2-4 hydroxyalkylamino, N,N-di-(C.sub.2-4 hydroxyalkyl)amino, --NH--(CH.sub.2).sub.m --SO.sub.3 H, anilino, morpholino, piperidino, piperazino or N-methylpiperazino.
- 15. A compound according to claim 14, or a salt thereof, wherein
- R.sub.2x is in the 6-position of Ring A, and
- R.sub.3x is in the 3-position of Ring A.
- 16. A compound according to claim 14, or a salt thereof, wherein R.sub.2x is hydrogn, methyl, methoxy, acetamido or --NHCONH.sub.2.
- 17. A compound according to claim 16, or a salt thereof, wherein the Kb--N.dbd.N-- group is in the 3- or 4-position of Ring B.
- 18. A compound according to claim 17, or a salt thereof, wherein Kb is ##STR316##
- 19. A compound according to claim 17, or a salt thereof, wherein Kb is ##STR317##
- 20. A compound according to claim 17 having the formula ##STR318## or a salt thereof, wherein R.sub.2b is hydrogen, methyl, methoxy, acetamido or --NHCONH.sub.2,
- R.sub.3a is hydrogen, methyl or methoxy,
- R.sub.4ax is hydrogen, C.sub.1-2 alkyl, C.sub.1-2 alkoxy or sulfo, and
- X.sub.c is --CO--, --SO.sub.2 -- or ##STR319## wherein Yax is hydroxy, methoxy, amino, C.sub.1-2 alkylamino, C.sub.2-4 hydroxyalkylamino, N,N-di-(C.sub.2-4 hydroxyalkyl)amino, --NH--(CH.sub.2).sub.m --SO.sub.3 H, anilino, morpholino, piperidino, piperazino or N-methylpiperazino,
- with the provisos that the compound contains 1, 2, 3 or 4 sulfo groups and the number of sulfo groups equals or exceeds the total number of basic and cationic groups.
- 21. A compound according to claim 20, or a salt thereof, wherein Xc is ##STR320##
- 22. A compound according to claim 20, or a salt thereof, wherein Da is 1,5-, 3,6-, 4,8-, 5,7- or 6,8-disulfonaphthyl-2, 3,6,8- or 4,6,8-trisulfonaphthyl-2, 3,6-, 4,6-, 3,8- or 4,8-disulfonaphthyl-1, 3,6,8-trisulfonaphthyl-1 or ##STR321## wherein R.sub.7a is hydrogen, chloro, methyl, methoxy or acetamido.
- 23. A compound according to claim 20, or a salt thereof, wherein R.sub.1b is hydrogen.
- 24. A compound according to claim 20, or a salt thereof, wherein R.sub.4ax is hydrogen.
- 25. A compound according to claim 20, or a salt thereof, wherein Xc is --CO--.
- 26. A compound according to claim 20, or a salt thereof, wherein the Kb--N.dbd.N-- group is in the 4-position of Ring B.
- 27. A compound according to claim 26, or a salt thereof, wherein
- R.sub.1b is hydrogen,
- R.sub.4ax is hydrogen, and
- Xc is --CO--.
- 28. A compound according to claim 27, or a salt thereof, wherein Kb is ##STR322## wherein Y.sub.2b is .dbd.NCN or .dbd.NCONH.sub.2.
- 29. The compound according to claim 28 having the formula ##STR323## or a salt thereof.
- 30. The compound according to claim 29 in sodium salt form.
- 31. The compound according to claim 28 having the formula ##STR324## or a salt thereof.
- 32. A storage-stable, liquid aqueous dyeing preparation containing a compound according to claim 1, in water-soluble salt form.
Priority Claims (1)
Number |
Date |
Country |
Kind |
3515083 |
Apr 1985 |
DEX |
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Parent Case Info
This is a continuation-in-part of application Ser. No. 06/856,606, filed Apr. 25, 1986 and now abandoned.
US Referenced Citations (9)
Foreign Referenced Citations (3)
Number |
Date |
Country |
2357611 |
Feb 1978 |
FRX |
533161 |
Jan 1973 |
CHX |
633790 |
Dec 1949 |
GBX |
Non-Patent Literature Citations (1)
Entry |
Colour Index, 3rd Edition, pp. 4267 to 4270, 6400, and 7278 to 7279 (CI 29000 to 29090) (1971). |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
856606 |
Apr 1986 |
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