| PATENT ASSIGNEE'S COUNTRY | Germany |
| UPDATE | 05.00 |
| PATENT NUMBER | This data is not available for free |
| PATENT GRANT DATE | 09.05.00 |
| PATENT TITLE |
Water-soluble fiber-reactive dyes, processes for their preparation, and their use |
| PATENT ABSTRACT |
The disclosed dyes (which are fiber-reactive and are useful for dyeing materials containing OH and/or carboxamide groups) are compounds of the formula (1) Fb--Z.sub.n (1) in which: Fb is the radical of various classes of dyestuffs, including the formazans, azomethines, phthalocyanines, etc., and particularly sulfo group-containing monoazo or disazo dyes of the formulas (a-1) through (a-5): D.sup.1 --N.dbd.N--K.sup.2 -- (a-1) --D.sup.2 --N.dbd.N--(E--N.dbd.N).sub.v --K.sup.1 (a-2) --D.sup.2 --N.dbd.N--(E--N.dbd.N).sub.v --K.sup.2 -- (a-3) D.sup.1 --N.dbd.N--K.sup.0 --N.dbd.N--D.sup.2 -- (a-4) --D.sup.1 --N.dbd.N--K.sup.0 --N.dbd.N--D.sup.2 -- (a-5) in which in which D.sup.1 is a substituted or unsubstituted phenyl or naphthyl radical, D.sup.2 is the radical of a diazo component and K.sup.1, K.sup.2, and K.sup.0 are various coupling components, and E is a middle component. |
| PATENT INVENTORS | This data is not available for free |
| PATENT ASSIGNEE | This data is not available for free |
| PATENT FILE DATE | 01.12.97 |
| PATENT FOREIGN APPLICATION PRIORITY DATA | This data is not available for free |
| PATENT REFERENCES CITED | This data is not available for free |
| PATENT CLAIMS |
We claim: 1. A dye corresponding to the formula (1) Fb--Z.sub.n ( 1) in which: Fb is the radical of a sulfo group containing monoazo dye of the formula (a-1) D.sup.1 --N.dbd.N--K.sup.2 -- (a-1) in which D.sup.1 is a substituted or unsubstituted phenyl or naphthyl radical, and K.sup.2 is the substituted or unsubstituted residue of an aniline, aminonaphthalene, acetic acid (aminoaryl)amide or 1-aminophenyl-pyrazolone coupling component, or Fb is the radical of a sulfo group containing mono-or disazo dye conforming to the formulae (a-2) to (a-5) --D.sup.2 --N.dbd.N--(E--N.dbd.N).sub.v --K.sup.1 (a- 2) --D.sup.2 --N.dbd.N--(E--N.dbd.N).sub.v --K.sup.2 -- (a-3) D.sup.1 --N.dbd.N--K.sup.0 --N.dbd.N--D.sup.2 -- (a-4) --D.sup.1 --N.dbd.N--K.sup.0 --N.dbd.N--D.sup.2 -- (a-5) in which D.sup.1 and K.sup.2 are as previously defined, v is zero or 1, E is the substituted or unsubstituted phenyl or naphthyl radical of a middle component, D.sup.2 is the substituted or unsubstituted diaminophenyl or diaminonaphthyl radical of a diazo component and K.sup.1 is the substituted or unsubstituted phenyl, naphthyl, pyrazolone, 6-hydroxy-pyrid-2-one or acetoacetic acid arylamide radical of a coupling component, and K.sup.0 is the radical of a bivalent coupling component having a substituted or unsubstituted naphthalene nucleus, provided that D.sup.1, D.sup.2, and K.sup.0 together contain at least one sulfo group, or Fb is the radical of a sulfo-containing heavy metal complex mono-, dis- or trisazo, azomethine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthine, nitroaryl, naphthoquinone, pyrenequinone, perylenetetracarbimide, formazan, phthalocyanine, or triphendioxazine dye, and with respect to formulae a-1 through a-5 and the said radicals D.sup.1, D.sup.2, K.sup.1, K.sup.2, K.sup.0 and E, when substituted, these formulae or radicals contain, additionally to sulfo, at least one of the following substituents: alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; alkanoylamino of 2 to 5 carbon atoms; benzoylamino unsubstituted or substituted by substituents selected from sulfo, carboxy, methyl, ethyl, methoxy, ethoxy and chlorine; primary and mono- or disubstituted amino groups, where the substituents are selected from alkyl of 1 to 4 carbon atoms and phenyl, where the alkyls are unsubstituted or substituted by phenyl, sulfophenyl, hydroxy, sulfato, sulfo or carboxy and the phenyl groups are unsubstituted or substituted by substituents selected from chlorine, sulfo, carboxy, methyl and methoxy; alkoxycarbonyl having an alkyl of 1 to 4 carbon atoms; alkylsulfonyl of 1 to 4 carbon atoms; trifluoromethyl; nitro; cyano; halogen; carbamoyl; carbamoyl mono- or disubstituted by alkyl of 1 to 4 carbon atoms, where the alkyls are unsubstituted or substituted by hydroxy, sulfato, sulfo, carboxy, phenyl or sulfophenyl; sulfamoyl; sulfamoyl mono- or disubstituted by alkyl of 1 to 4 carbon atoms, the alkyls being unsubstituted or substituted by hydroxy, sulfato, sulfo, carboxy, phenyl or sulfophenyl; N-phenyl-N-alkysulfamoyl having an alkyl of 1 to 4 carbon atoms, the alkyls being unsubstituted or substituted by hydroxy, sulfato, sulfo, carboxy, phenyl or sulfophenyl; N-phenylsulfamoyl; ureido; carboxy; sulfomethyl or from one to two fiber-reactive groups of the formula Y--SO.sub.2 --W.sup.0 -- in which W.sup.0 is an alkylene of 1 to 4 carbon atoms or is --N(CH.sub.3 -- or --N(C.sub.2 H.sub.5)-- or --(C.sub.2 -C.sub.4 -alkylene)--NH-- or a direct covalent bond and Y is vinyl or is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-(C.sub.2 -C.sub.5 -alkanoxyloxy) ethyl, .beta.-benzoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy) ethyl or .beta.-haloethyl; n is the number 1, 2 or 3; Z is a group of the formula (2) ##STR53## in which Q is a covalent bond or a group of the formula ##STR54## in which R is hydrogen or alkyl of 1 to 4 carbon atoms optimally substituted by halogen, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, carboxy, sulfamoyl, sulfo, sulfato or phosphato, W is a covalent bond of a bridging member, except that Q is necessarily a covalent bond if W is a covalent bond, and the amino groups --N(R.sup.A)-- and --N(R)-- are bonded to one carbon atom of the bridging member W or to one carbon atom of a substituent of W, and R is hydrogen, or is alkyl of 1 to 4 carbon atoms optionally substituted by halogen, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, carboxy, sulfamoyl, sulfo, sulfato or phosphate. 2. A dye as claimed in claim 1, wherein Fb is a radical of the formula 3g ##STR55## wherein n is 1 or 2, M is hydrogen, an alkali metal, or the molar equivalent of an alkaline earth metal, Z is a group of the formula (2), and D is defined in the same manner as D.sup.1 if unsubstituted by Z, or is defined in the same manner as D.sup.2 if substituted by Z. 3. A dye as claimed in claim 1, wherein Fb is the radical of a sulfo group-containing 1:1 copper complex mono- or disazo dye. 4. A dye as claimed in claim 1, wherein Fb is the radical of a sulfo group-containing copper formazan dye. 5. A dye as claimed in claim 1, wherein Fb is the radical of a sulfo group-containing aluminum phthalocyanine, copper phthalocyanine or nickel phthalocyanine dye. 6. A dye as claimed in claim 1, wherein Fb is the radical of a sulfo group-containing triphendioxazine dye. 7. A dye as claimed in claim 1, wherein Q is a direct bond or a group of the formula --N(R.sup.A)-- wherein R.sup.A is defined as in claim 1. 8. A dye as claimed in claim 7, wherein R.sup.A is hydrogen. 9. A dye as claimed in claim 1, wherein n is the number 1. 10. A dye as claimed in claim 1, wherein R is hydrogen. 11. A dye as claimed in claim 1, wherein Q and W are both a covalent bond. 12. A dye as claimed in claim 1, wherein W is straight-chain or branched alkylene of 1 to 6 carbon atoms, or is alkylene of 2 to 8 carbon atoms which is interrupted by 1 or 2 hetero groups selected from the group consisting of --NH--, --N(R.sup.A)-- with R.sup.A having the meaning mentioned in claim 1, --SO.sub.2 --, --CO--, --O--, --NH--SO.sub.2 --, --SO.sub.2 --NH--, --CO--NH-- and --NH--CO--, or is optionally substituted arylene or optionally substituted arylenealkylene or is a radical containing two arylene radicals whose arylene radicals are bonded with one another via a covalent bond, a hetero group or an alkylene of 1 to 4 carbon atoms or an olefinic radical of 2 to 4 carbon atoms, or is the bivalent radical of a heterocyclic system to which optionally the bivalent radical of an optionally substituted phenylene-amino, phenylene-methylene-amino, naphthylene-amino or (C.sub.1 -C.sub.6)-alkylene-amino radical is bonded. 13. A dye as claimed in claim 1, wherein W is a group of the formula (a) ##STR56## in which G is fluorine, chlorine, bromine, cyanoamino, optionally substituted amino, hydroxy, alkoxy of 1 to 4 carbon atoms, phenoxy, phenoxy optionally substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, or is alkylthio of 1 to 4 carbon atoms, R.sup.B is hydrogen, or alkyl of 1 to 4 carbon atoms optionally substituted by halogen, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, carboxy, sulfamoyl, sulfo, sulfato or phosphate, and W.sup.A is straight-chain alkylene of 2 to 6 carbon atoms or branched alkylene of 3 to 6 carbon atoms, each of which is interrupted by one or two hetero groups which are selected from the groups of the formulae --O--, --CO--, --SO.sub.2 --, --NH--, --N(R.sup.A) with R.sup.A having one of the meanings mentioned in claim 1, --NH--CO--, --CO--NH--, --SO.sub.2 --NH-- and --NH--SO.sub.2 --, or is phenylene optionally substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy. 14. A dye as claimed in claim 13, wherein W is a group of the formula (a) ##STR57## in which G is fluorine, chlorine, bromine, cyanoamino, optionally substituted amino, hydroxy, alkoxy of 1 to 4 carbon atoms, phenoxy, phenoxy optionally substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, or is alkylthio of 1 to 4 carbon atoms, R.sup.B is hydrogen, or alkyl of 1 to 4 carbon atoms optionally substituted by halogen, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, carboxy, sulfamoyl, sulfo, sulfato or phosphate, and W.sup.A is straight-chain alkylene of 2 to 6 carbon atoms or branched alkylene of 3 to 6 carbon atoms, each of which is interrupted by one or two hetero groups which are selected from the groups of the formulae --O--, --CO--, --SO.sub.2 --, --NH--, --N(R.sup.A) with R.sup.A having one of the meanings mentioned in claim 1, --NH--CO--, --CO--NH--, --SO.sub.2 --NH-- and --NH--SO.sub.2 --, or is phenylene optionally substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy. 15. A process for dyeing a material containing hydroxy or carboxamide groups or both, in which a dye is applied to the material and the dye is fixed to the material by means of heat or with the aid of an alkaline agent or by means of both measures, which comprises employing as a dye a dye as defined in claim 1. 16. A process according to claim 15, wherein the material is a fiber-material. -------------------------------------------------------------------------------- |
| PATENT DESCRIPTION |
The invention is in the technical field of fiber-reactive dyes. The practise of dyeing with fiber-reactive dyes additionally leads to increased demands on the quality of the dyeings and the economy of the dyeing process, which is why novel fiber-reactive dyes are required which have improved properties, not only good fastnesses, but also a high degree of fixing to the material to be dyed. Thus in German Offenlegungsschrift No. 4 122 100 and U.S. Pat. Nos. 5,319,074, 5,340,928, 5,436,324 and 5,538,518, fiber-reactive dyes are disclosed which contain a 2,4-difluoropyrimidin-6-yl radical as a fiber-reactive component. Because of the increased demands addressed, these known dyes are worthy of improvement, in particular with respect to their degree of fixing and the color intensity of the dyeings and prints obtainable using them. With the present invention, novel fiber-reactive dyes having a 5,6-difluoropyrimidin-4-yl radical as a fiber-reactive group have been found, which correspond to the formula (1) Fb--Z.sub.n (1) defined below and differ advantageously from the known dyes and yield dyeings and prints having high color intensity. In the formula (1): Fb is the radical of a sulfo group-containing mono-, dis- or polyazo dye, such as a trisazo dye, or heavy metal complex mono-, dis- or trisazo dye or anthraquinone, azomethine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthene, nitroaryl, naphthoquinone, pyrenequinone, perylenetetracarbimide, formazan, copper formazan, phthalocyanine, copper phthalocyanine, nickel phthalocyanine, cobalt phthalocyanine, aluminum phthalocyanine or triphendioxazine dye; n is the number 1, 2 or 3, preferably 1 or 2, particularly preferably 1; Z is a group of the formula (2) ##STR1## in which Q is a covalent bond or a group of the formula ##STR2## preferably a group of the formula --N(R.sup.A)-- or a covalent bond, in which R.sup.A is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, optionally substituted by halogen, such as chlorine and bromine, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, alkoxycarbonyl of 2 to 5 carbon atoms, such as carbethoxy and carbomethoxy, carboxy, sulfamoyl, sulfo, sulfato or phosphato, and is preferably methyl or ethyl and particularly preferably hydrogen, W is a covalent bond or a bridging member, such as, for example, a straight-chain or branched alkylene radical of 1 to 6 carbon atoms or an alkylene radical of 2 to 8 carbon atoms, which is interrupted by 1 or 2 hetero groups from the group consisting of --NH--, --N(R.sup.A)-- with R.sup.A having the abovementioned meaning, --SO.sub.2 --, --CO--, --O--, --NH--SO.sub.2 --, --SO.sub.2 --NH--, --CO--NH-- and --NH--CO--, or an optionally substituted arylene radical or an optionally substituted arylene-alkylene radical or, for example, a radical containing two arylene radicals which are bonded to one another via a covalent bond, a hetero group, such as --NH-- or --O--, or an alkylene radical of 1 to 4 carbon atoms or an olefinic radical of 2 to 4 carbon atoms, or, for example, the bivalent radical of a heterocycle, such as a triazine, to which the bivalent radical of an optionally substituted phenylene-amino, naphthylene-amino, phenylene-methylamino or (C.sub.1 -C.sub.6)-alkylene-amino radical can be bonded, but where Q is compulsorily a covalent bond if W is a covalent bond, and where the amino groups --N(R.sup.A)-- and --N(R)-- are bonded to one carbon atom of the bridging member W or to one carbon atom of a substituent of W, and R is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, optionally substituted by halogen, such as chlorine and bromine, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, alkoxycarbonyl of 2 to 5 carbon atoms, such as carbomethoxy and carbethoxy, carboxy, sulfamoyl, sulfo, sulfato or phosphato, preferably methyl or ethyl and particularly preferably hydrogen. Arylene radicals are preferably phenylene radicals which are optionally substituted, such as, for example, by one or two substituents from the group consisting of sulfo, carboxy, alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, chlorine, hydroxy and alkanoylamino of 2 to 4 carbon atoms, such as propionylamino and acetylamino, and naphthylene radicals are optionally substituted, for example, by 1, 2 or 3 sulfo groups or by 1 or 2 carboxy groups or by alkyl of 1 to 4 carbon atoms, such as ethyl and methyl, or alkoxy of 1 to 4 carbon atoms, such as ethoxy and methoxy, or by two or three substituents from the group consisting of alkyl of 1 to 4 carbon atoms, such as ethyl and methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and methoxy, sulfo and carboxy. Alkylene radicals are preferably those of 1 to 4 carbon atoms. Fb is preferably the radical of a mono- or disazo dye or the radical of a heavy metal complex azo dye, such as a 1:2 chromium complex, 1:2 cobalt complex and in particular of a o,o'-1:1 copper complex monoazo or disazo dye, or the radical of an anthraquinone or copper formazan or of a nickel, copper or aluminum phthalocyanine dye or of a triphendioxazine dye. The dye radical Fb has one or more, such as 2 to 6, sulfo groups. The radical Fb can contain further substituents which are customary in organic dyes. Such substituents are, for example: alkyl groups of 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl or butyl, of these preferably ethyl and in particular methyl; alkoxy groups of 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy and butoxy, of these preferably ethoxy and in particular methoxy; alkanoylamino groups of 2 to 5 carbon atoms, such as the acetylamino and propionylamino groups; benzoylamino groups optionally substituted by sulfo, carboxy, methyl, ethyl, methoxy, ethoxy and/or chlorine; primary and mono- or disubstituted amino groups, where the substituents are, for example, alkyl groups of 1 to 4 carbon atoms and/or phenyl groups, such as monoalkylamino and dialkylamino groups having 1 to 4 carbon atoms in the alkyl radical, phenylamino or N--(C.sub.1 -C.sub.4 -alkyl)-N-phenylamino groups, where the alkyl radicals can also be substituted, for example by phenyl, sulfophenyl, hydroxy, sulfato, sulfo and carboxy, and the phenyl groups can also be substituted, such as by chlorine, sulfo, carboxy, methyl and/or methoxy, i.e., for example, methylamino, ethylamino, propylamino, isopropylamino, butylamino, N,N-di-(.beta.-hydroxyethyl)amino, N,N-di-(.beta.-sulfatoethyl)amino, sulfobenzylamino, N,N-di-(sulfobenzyl)amino and diethylamino groups and also phenylamino and sulfophenylamino groups; alkoxycarbonyl groups having an alkyl radical of 1 to 4 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; alkylsulfonyl groups of 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl; trifluoromethyl, nitro and cyano groups; halogen atoms, such as fluorine, chlorine and bromine; carbamoyl groups which can be mono- or disubstituted by alkyl of 1 to 4 carbon atoms, where the alkyl radicals can in turn be substituted, for example by hydroxy, sulfato, sulfo, carboxy, phenyl and sulfophenyl, such as, for example, N-methylcarbamoyl and N-ethylcarbamoyl; sulfamoyl groups which can be mono- or disubstituted by alkyl groups of 1 to 4 carbon atoms, and N-phenyl-N-alkylsulfamoyl groups having an alkyl group of 1 to 4 carbon atoms, where these alkyl groups in turn can be substituted by hydroxy, sulfato, sulfo, carboxy, phenyl and sulfophenyl, such as, for example N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-(.beta.-hydroxyethyl)sulfamoyl and N,N-di-(.beta.-hydroxyethyl)sulfamoyl; N-phenylsulfamoyl, ureido, hydroxy, carboxy, sulfomethyl and sulfo groups. The dye radical Fb can furthermore have one or two fiber-reactive groups of the formula Y--SO.sub.2 --W.sup.O --, in which W.sup.O is an alkylene radical of 1 to 4 carbon atoms or an amino group of the formula --N(CH.sub.3)-- or --N(C.sub.2 H.sub.5)-- or a group of the formula --(C.sub.2 -C.sub.4 -alkylene)--NH-- or a direct covalent bond and Y is vinyl or is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-(C.sub.2 -C.sub.5 -alkanoyloxy)ethyl, such as .beta.-acetyloxyethyl, .beta.-benzoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-haloethyl, such as .beta.-bromoethyl or .beta.-chloroethyl, and is preferably vinyl and particularly preferably .beta.-chloroethyl or .beta.-sulfatoethyl. Bridge members W are in particular 1,2-ethylene, 1,3-propylene, 1,4-butylene, 1,2-propylene, 1,3-butylene, straight-chain alkylene of 2 to 6 carbon atoms and branched alkylene of 3 to 6 carbon atoms, each of which is interrupted by 1 or 2 hetero groups, which are selected from the groups of the formulae --O--, --CO--, --SO.sub.2 --, --NH--, --N(R.sup.A)-- with R.sup.A having one of the abovementioned meanings, --NH--CO--, --CO--NH--, --SO.sub.2 --NH-- or --NH--SO.sub.2 --, phenylene which can be substituted by 1 or 2 substituents from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, such as, for example, phen-1,3-ylene, phen-1,4-ylene, 6-sulfophen-1,3-ylene, 6-sulfophen-1,4-ylene, 3,6-disulfophen-1,4-ylene, 6-methoxyphen-1,3-ylene or benzylidene which can be substituted by 1 or 2 substituents from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, such as, for example 1,4-benzylidene, 1,3-benzylidene, 2-sulfophen-1-yl-4-methylene, 2-sulfophen-1-ylene-5-methylene and 2-methoxyphen-1-yl-4-methylene, in addition the radical of 1,1-diphen-4,4'-ylene, which can be substituted in each phenylene radical by methyl, methoxy or sulfo, or is the 1,1'-stilben-4,4'-ylene radical, which can be substituted in each phenylene radical by methyl, methoxy or sulfo, furthermore a radical of the formula (a) ##STR3## in which G is fluorine, chlorine, bromine, cyanoamino, optionally substituted amino, hydroxy, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, phenoxy optionally substituted by 1 or 2 substituents from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, or alkylthio of 1 to 4 carbon atoms, such as methylthio and ethylthio, but preferably chlorine or fluorine, R.sup.B is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, optionally substituted by halogen, such as chlorine and bromine, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, alkoxycarbonyl of 2 to 5 carbon atoms, such as carbethoxy and carbomethoxy, carboxy, sulfamoyl, sulfo, sulfato or phosphate, and is preferably methyl or ethyl and particularly preferably hydrogen, and W.sup.A is straight-chain alkylene of 2 to 6 carbon atoms or branched alkylene of 3 to 6 carbon atoms, each of which can be interrupted by one or two hetero groups which are selected from the groups of the formulae --O--, --CO--, --SO.sub.2 --, --NH--, --N(R.sup.A)-- with R.sup.A having one of the abovementioned meanings, --NH--CO--, --CO--NH--, --SO.sub.2 --NH-- or --NH--SO.sub.2 --, or is phenylene optionally substituted by 1 or 2 substituents from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, such as, for example, phen-1,3-ylene, phen-1,4-ylene, 6-sulfophen-1,3-ylene, 6-sulfophen-1,4-ylene, 3,6-disulfophen-1,4-ylene, 6-methoxyphen-1,3-ylene or benzylidene optionally substituted by 1 or 2 substituents from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy and ethoxy, such as, for example, 1,4-benzylidene, 1,3-benzylidene, 2-sulfophen-1-yl-4-methylene, 2-sulfophen-1-yl-5-methylene or 2-methoxyphen-1-yl-4-methylene. In the above and in the following formulae, the individual formula members, of both a different and also the same description within the formula, can have meanings which are identical to one another or different from one another in their scope. The groups "sulfo", "thiosulfato", "carboxy", "phosphate" and "sulfato" include both their acid form and their salt form. Accordingly, sulfo groups are groups corresponding to the formula --SO.sub.3 M, thiosulfato groups are groups corresponding to the formula --S--SO.sub.3 M, carboxy groups are groups corresponding to the formula --COOM, phosphate groups are groups corresponding to the formula --OPO.sub.3 M.sub.2 and sulfato groups are groups corresponding to the formula --OSO.sub.3 M, in which M is hydrogen or an alkali metal, such as sodium, potassium or lithium, or the molar equivalent of an alkaline earth metal, such as of calcium, and preferably hydrogen or an alkali metal. Important azo dyes corresponding to the formula (1) are those in which Fb is the radical of a sulfo group-containing dye of the benzeneazonaphthol, the benzeneazo-1-phenyl-5-pyrazolone, the benzeneazobenzene, the naphthaleneazobenzene, the benzeneazoaminonaphthalene, the naphthaleneazonaphthalene, the naphthaleneazo-1-phenyl-5-pyrazolone, the benzeneazopyridone and the naphthaleneazopyridone series. Of the 1:1 copper complex azo dyes according to the invention, those of the benzene and naphthalene series are preferred. Preferred mono- and disazo dyes of the formula (1) are, for example, those of the formulae (3a), (3b), (3c) and (3d) ##STR4## and the heavy metal complex compounds derived therefrom, such as 1:1-copper complex compounds, in which D.sup.1 is the radical of a diazo component of the benzene or naphthalene series, D.sup.2 is the radical of a diazo component of the diaminobenzene or diaminonaphthalene series, E is the radical of a middle component of the benzene or naphthalene series, K.sup.1 is the radical of a coupling component of the benzene, naphthalene, pyrazolone, 6-hydroxypyrid-2-one or acetoacetic acid arylamide series, K.sup.2 is the bivalent radical of a coupling component of the aniline, aminonaphthalene, acetic acid (aminoaryl)amide or 1-aminophenylpyrazolone series, where D.sup.1, D.sup.2, E, K.sup.1 and K.sup.2 can contain one or more of the substituents mentioned for Fb and the radicals D.sup.1, D.sup.2, E, K.sup.1 and K.sup.2 together have at least one, preferably at least two, sulfo groups, v is the number zero or 1 and Z is a group of the formula (2) of the above meaning. Preferred disazo dyes are furthermore those of the formulae (3e) and (3f) D.sup.1 --N.dbd.N--K.sup.o --N.dbd.N--D.sup.2 --Z (3e) Z--D.sup.2 --N.dbd.N--K.sup.o --N.dbd.N--D.sup.2 --Z (3f) in which Z, D.sup.1 and D.sup.2 have the abovementioned meanings and K.sup.o is the radical of a bivalent coupling component of the naphthalene series, where D.sup.1, D.sup.2 and K.sup.o can contain the substituents mentioned for Fb and D.sup.1, D.sup.2 and K.sup.o together contain at least one sulfo group. Azo dyes of the formulae (3d) and (3e) are particularly dyes of the formula (3g) ##STR5## in which n has the abovementioned meaning, M is hydrogen or alkali metal, such as sodium, potassium or lithium, or the molar equivalent of an alkaline earth metal, such as of calcium, Z is a radical of the formula (2), which if n is 1 is on one of the radicals D and if n is 2 is bonded to both Ds, and D each has the meaning of D.sup.1 or D.sup.2, depending on whether the radical Z is bonded to D. Of the 1:1 copper complex azo dyes, for example, those of the formula (3h) and (3i) ##STR6## are to be emphasized, in which Z, K.sup.2 and v have the abovementioned meanings, D.sup.4 is the radical of a diazo component which in the ortho-position relative to the azo group contains the copper complex-binding oxy group, and K.sup.3 is the radical of a coupling component which in the ortho-position or vicinal position relative to the azo group has the copper complex-binding oxy group, and K is the bivalent radical of a coupling component. Aromatic radicals of diazo components which bear no fiber-reactive group of the formula (2), such as of those which correspond to the formulae D.sup.1 --NH.sub.2 and D.sup.3 --NH.sub.2, are, for example, those of the formulae (4a), (4b), (5a) and (5b) ##STR7## in which R.sup.G is hydrogen, sulfo or a group of the formula Y--SO.sub.2 --W.sup.o -- with W.sup.o and Y having the above meaning, P.sup.1 is hydrogen, methyl, ethyl, methoxy, ethoxy, alkanoyl of 2 to 5 carbon atoms, such as acetyl and propionyl, cyano, sulfo, carboxy, alkoxycarbonyl of 2 to 5 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl, carbamoyl, N--(C.sub.1 -C.sub.4 -alkyl)carbamoyl, fluorine, chlorine, bromine or trifluoromethyl, P.sup.2 is hydrogen, methyl, ethyl, methoxy, ethoxy, cyano, nitro, carboxy, sulfo, chlorine, alkanoylamino of 2 to 5 carbon atoms, such as acetylamino, alkoxycarbonyl of 2 to 5 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl, carbamoyl, N--(C.sub.1 -C.sub.4 -alkyl)sulfamoyl, sulfophenylamidocarbonyl, phenylamidocarbonyl, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl or phenoxy, where the benzene nucleus in formulae (4a) and (4b) can additionally contain a hydroxy group in the ortho-position relative to the free bond which leads to the azo group, m is the number zero, 1 or 2 (where if m is zero this group is a hydrogen atom) and M has the abovementioned meaning. Of these, P.sup.1 is preferably hydrogen, methyl, methoxy, bromine, chlorine, sulfo and carboxy, and P.sup.2 is hydrogen, methyl, methoxy, chlorine, carboxy, sulfo and acetylamino. Groups of the formulae (4a) and (4b) are, for example: phenyl, 2-methylphenyl, 3- and 4-methylphenyl, 2-methoxyphenyl, 3- and 4-methoxyphenyl, 2-chlorophenyl, 3- and 4-chlorophenyl, 2,5-dichlorophenyl, 2,5-dimethylphenyl, 2-methoxy-5-methylphenyl, 2-methoxy-4-nitrophenyl, 4-phenylphen-1-yl, 3-phenoxyphenyl, 2-sulfamoylphenyl, 3- and 4-sulfamoylphenyl, 2-, 3- and 4-(N-methylsulfamoyl), -(N-ethylsulfamoyl), -(N,N-dimethylsulfamoyl) and -(N,N-diethylsulfamoyl)phenyl, 2-sulfo-5-trifluoromethylphenyl, 2-nitrophenyl, 3- and 4-nitrophenyl, 3-acetylaminophenyl, 4-acetylaminophenyl, 2-carboxyphenyl, 4-carboxyphenyl, 3-carboxyphenyl, 3-chloro-6-carboxyphenyl, 2-sulfophenyl, 3-sulfophenyl, 4-sulfophenyl, 2,5-disulfophenyl, 2,4-disulfophenyl, 3,5-disulfophenyl, 2-methyl-5-sulfophenyl, 2-methoxy-5-sulfophenyl, 2-methoxy-4-sulfophenyl, 2-sulfo-5-methylphenyl, 2-methyl-4-sulfophenyl, 3-sulfo-4-methoxy-phenyl, 5-sulfo-2-ethoxyphenyl, 4-sulfo-2-ethoxyphenyl, 2-carboxy-5-sulfophenyl, 2-carboxy-4-sulfophenyl, 2,5-dimethoxy-4-sulfophenyl, 2,4-dimethoxy-5-sulfophenyl, 2-methoxy-5-methyl-4-sulfophenyl, 2-sulfo-4-methoxyphenyl, 2-sulfo-4-methylphenyl, 2-methyl-4-sulfo-phenyl, 2-chloro-4-sulfophenyl, 2-chloro-5-sulfophenyl, 2-bromo-4-sulfophenyl, 2,6-dichloro-4-sulfophenyl, 2-sulfo-4- and -5-chlorophenyl, 2-sulfo-4,5-dichlorophenyl, 2,5-dichloro-6-sulfophenyl, 2,5-dichloro-4-sulfophenyl, 2-sulfo-5-chloro-4-methylphenyl, 2-sulfo-4-chloro-5-methylphenyl, 2-sulfo-5-methoxyphenyl, 2-methoxy-5-sulfophenyl, 2-methoxy-4-sulfophenyl, 2,4-dimethoxy-6-sulfophenyl, 2-sulfo-5-acetylamino-4-methylphenyl, 2-methyl-4,6-disulfophenyl, 2,5-disulfo-4-methoxyphenyl, 2-sulfo-5-nitrophenyl, 2-sulfo-4-nitrophenyl, 2,6-dimethyl-3-sulfophenyl, 2,6-dimethyl-4-sulfophenyl, 3-acetylamino-6-sulfophenyl, 4-acetylamino-2-sulfophenyl, 4-sulfonaphth-1-yl, 3-sulfonaphth-1-yl, 5-sulfonaphth-1-yl, 6-sulfonaphth-1-yl, 7-sulfonaphth-1-yl, 8-sulfonaphth-1-yl, 3,6-disulfo- and 5,7-disulfonaphth-1-yl, 3,7-disulfonaphth-1-yl, 3,6,8-trisulfonaphth-1-yl, 4,6,8-trisulfonaphth-1-yl, 5-sulfonaphth-2-yl, 6- or 8-sulfonaphth-2-yl, 3,6,8-trisulfonaphth-2-yl, 1,5,7-trisulfonaphth-2-yl, 1,7-disulfonaphth-2-yl, 5,7-disulfonaphth-2-yl, 2,5,7-trisulfonaphth-1-yl, 4,6,8-trisulfonaphth-2-yl, 6,8-disulfonaphth-2-yl, 1,6-disulfonaphth-2-yl, 1-sulfonaphth-2-yl, 1,5-disulfonaphth-2-yl, 3,6-disulfonaphth-2-yl, 4,8-disulfonaphth-2-yl, 2-hydroxy-5-sulfophenyl, 2-hydroxy-4-sulfophenyl, 2-hydroxy-3,5-disulfophenyl, 2-hydroxy-5-acetylamino-3-sulfophenyl, 2-hydroxy-3-acetylamino-4-sulfophenyl, 2-hydroxy-5-chloro-4-sulfophenyl, 2-hydroxy-5-methylsulfonylphenyl, 2-hydroxy6-nitro-4-sulfonaphth-1-yl and 1-hydroxy-4,8-disulfonaphth-2-yl, 2-(.beta.-sulfatoethylsulfonyl)phenyl, 3-(.beta.-sulfatoethylsulfonyl)phenyl, 4-(.beta.-sulfatoethylsulfonyl)phenyl, 2-carboxy-5-(.beta.-sulfatoethylsulfonyl)phenyl, 2-chloro-3-(sulfatoethylsulfonyl)phenyl, 2-chloro4-(.beta.-sulfatoethylsulfonyl)phenyl, 2-bromo-4-(.beta.-sulfatoethylsulfonyl)phenyl, 4-methoxy-3-(.beta.-sulfatoethylsulfonyl)phenyl, 4-chloro-3-(.beta.-sulfatoethylsulfonyl)phenyl, 2-ethoxy-4- or -5-(.beta.-sulfatoethylsulfonyl)phenyl, 2-methyl-4-(.beta.-sulfatoethylsulfonyl)phenyl, 2-methoxy-5- or 4-(.beta.-sulfatoethylsulfonyl)phenyl, 2,4-diethoxy-5-(.beta.-sulfatoethylsulfonyl)phenyl, 2,4-dimethoxy-5-(.beta.-sulfatoethylsulfonyl)phenyl, 2,5-dimethoxy-4-(.beta.-sulfatoethylsulfonyl)phenyl, 2-methoxy-5-methyl-4-(.beta.-sulfatoethylsulfonyl)phenyl, 2- or 3- or 4-(.beta.-thiosulfatoethylsulfonyl)phenyl, 2-methoxy-5-(.beta.-thiosulfatoethylsulfonyl)phenyl, 2-sulfo-4-(.beta.-phosphatoethylsulfonyl)phenyl, 2-sulfo-4-vinylsulfonylphenyl, 2-hydroxy-4- or -5-(.beta.-sulfatoethylsulfonyl)phenyl, 2-chloro-4- or -5-(.beta.-chloroethylsulfonyl)phenyl, 2-hydroxy-5-(.beta.-sulfatoethylsulfonyl)phenyl, 2-hydroxy-3-sulfo-5-(.beta.-sulfatoethylsulfonyl)phenyl, 3- or 4-(.beta.-acetoxyethylsulfonyl)phenyl, 6-carboxy-1-sulfonaphth-2-yl, 5-(.beta.-sulfatoethylsulfonyl)naphth-2-yl, 6- or 7- or 8-(.beta.-sulfatoethylsulfonyl)naphth-2-yl, 6-(.beta.-sulfatoethylsulfonyl)-1-sulfonaphth-2-yl, 5-(.beta.-sulfatoethylsulfonyl)-1-sulfonaphth-2-yl, 8-(.beta.-sulfatoethylsulfonyl)-6-sulfonaphth-2-yl, 4-[N-methyl-N-(.beta.-sulfatoethylsulfonyl)]aminophenyl, 3-[N-methyl-N-(.beta.-sulfatoethylsulfonyl)]aminophenyl, 4-[.beta.-(.beta.'-sulfatoethylsulfonyl)ethyl]phenyl, 3- or 4-[.beta.-(.beta.'-chloroethylsulfonyl)ethylamino]phenyl, 3- or 4-[.beta.-(.beta.'-sulfatoethylsulfonyl)ethylamino]phenyl, 3- or 4-[.gamma.-(.beta.'-chloroethylsulfonyl)propylamino]phenyl, 3- or 4-[.gamma.-(.beta.'-sulfatoethylsulfonyl)propylamino]phenyl, 3- or 4-[.gamma.-(vinylsulfonyl)propylamino]phenyl, 4-[.beta.-(.beta.'-sulfatoethylsulfonyl)ethylamino]-2- or -3-sulfophenyl, 4-[.beta.-(.beta.'-chloroethylsulfonyl)ethylamino]-2- or -3-sulfophenyl, 4-[.gamma.-(.beta.'-sulfatoethylsulfonyl)propylamino]-2- or -3-sulfophenyl, 4-[.gamma.-(.beta.'-chloroethylsulfonyl)propylamino]-2- or -3-sulfophenyl, 4-[.beta.-(.beta.'-chloroethylsulfonyl)ethylamino]-2-carboxyphenyl, 4-[.beta.-(.beta.'-sulfatoethylsulfonyl)ethylamino]-2-carboxyphenyl, 4-[.gamma.-(.beta.'-chloroethylsulfonyl)propylamino]-2-carboxyphenyl and 4-[.gamma.-(.beta.'-sulfatoethylsulfonyl)propylamino]-2-carboxyphenyl. Groups corresponding to the formula radicals D--N.dbd.N--E-- and D.sup.1 --N.dbd.N--E-- are, for example, 4-(4'-sulfophenyl)azo-2-sulfophenyl, 4-(2',4'-disulfophenyl)azo-2-methoxy-5-methylphenyl, 4-(2',5'-disulfophenyl)azo-2-methyl-5-methoxyphenyl, 4-(3',6',8'-trisulfonaphth-2'-yl)-azo-3-ureidophenyl, 4-(4',8'-disulfonaphth-2'-yl)azo-3-acetylaminophenyl, 7-(1',5'-disulfonaphth-2'-yl)azo-6-sulfo-8-hydroxynaphth-3-yl and 4-(4'-sulfophenyl)azo-6-sulfonaphth-1-yl, 4-[4'-(.beta.-sulfatoethylsulfonyl)phenyl]azo-2-methyl-5-methoxyphenyl, 4-[3'-(.beta.'-sulfatoethylsulfonyl)phenyl]azo-3-methylphenyl, 4-[4'-(.beta.-sulfatoethylsulfonyl )phenyl]azo-3-ureidophenyl, 4-[6'-(.beta.-sulfatoethylsulfonyl)naphth-2'-yl]azo-3-ureidophenyl, 7-[2'-methoxy-5'-(.beta.-sulfatoethylsulfonyl)phenyl]azo-8-hydroxy-6-sulfo naphth-3-yl, 4-(2',5'-disulfophenyl)azo-6- or -7-sulfonaphth-1-yl, 4-(2',4'-disulfophenyl)azo-6- or -7-sulfonaphth-1-yl, 4-(4',8'-disulfonaphth-2'-yl)azo-6- or -7-sulfonaphth-1-yl, 4-(3',6',8'-trisulfonaphth-2'-yl)azo-6- or -7-sulfonaphth-1-yl and 4-(4',6',8'-trisulfonaphth-2'-yl)azo-6- or -7-sulfonaphth-1-yl. Aromatic radicals Z--D.sup.2 -- of compounds of the formula Z--D.sup.2 --NH.sub.2 serving as diazo components or of their diaminobenzene and diaminonaphthalene compounds corresponding to the formula H.sub.2 N--D.sup.2 --NH.sub.2 are preferably radicals of the formulae (6a) and (6b) ##STR8## in which Z, M, m, P.sup.1 and P.sup.2 have the particularly preferred meanings indicated above, Alk is alkylene of 1 to 3 C-atoms, preferably methylene, and x is the number zero or 1, where the respective benzene nucleus in the ortho position relative to the free bond which leads to the azo group can additionally contain a hydroxy group. Aromatic radicals E of a couplable and diazotizable compound of the formula H--E--NH.sub.2 are, for example, those of the formulae (7a), (7b) and (7c) ##STR9## in which P.sup.1, M and m have the meanings indicated above, Q.sup.1 is a group of the formula --Q--W--N(R)-- with Q, W and R having the abovementioned particularly preferred meanings, and P.sup.3 is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, chlorine, alkanoylamino of 2 to 5 carbon atoms, such as acetylamino and propionylamino, benzoylamino, ureido, phenylureido, alkylureido having 1 to 4 carbon atoms in the alkyl radical, phenylsulfonyl or alkylsulfonyl of 1 to 4 carbon atoms or a radical of the formula --Q.sup.1 --H with Q.sup.1 having the meaning indicated above, of these preferably the group --NH--. Radicals K.sup.1 of coupling components of the formula H--K.sup.1, which bear no fiber-reactive group of the formula (2), are, for example, those of the formulae (8a) to (8h) ##STR10## in which R.sup.G, P.sup.1, P.sup.2, m and M have the abovementioned meanings, P.sup.4 is alkanoylamino of 2 to 5 carbon atoms, such as propionylamino and in particular acetylamino, or phenylureido optionally substituted in the phenyl radical by substituents from the group consisting of chlorine, methyl, methoxy, sulfo and carboxy and/or by a group --SO.sub.2 --Y with Y having one of the above meanings, or is benzoylamino optionally substituted in the phenyl radical by substituents from the group consisting of chlorine, methyl, methoxy, nitro, sulfo and carboxy and/or by a group --SO.sub.2 --Y with Y having one of the above meanings, P.sup.5 is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, bromine, chlorine or sulfo, P.sup.6 is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, chlorine, alkanoylamino of 2 to 7 carbon atoms, such as acetylamino and propionylamino, ureido or phenylureido, P.sup.7 is hydrogen or alkyl of 1 to 4 carbon atoms optionally substituted by hydroxy, cyano, carboxy, sulfo, sulfato, methoxycarbonyl, ethoxycarbonyl or acetoxy, P.sup.8 is alkyl of 1 to 4 carbon atoms optionally substituted by hydroxy, cyano, carboxy, sulfo, sulfato, methoxycarbonyl, ethoxycarbonyl or acetoxy, or is benzyl or phenyl or phenyl substituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, chlorine and/or sulfo, P.sup.9 is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl, cyano, carboxy, carbalkoxy of 2 to 5 carbon atoms, such as carbomethoxy and carbethoxy, carbamoyl or phenyl, preferably methyl, carboxy, methoxycarbonyl, ethoxycarbonyl or phenyl and in particular methyl or carboxy, T is a benzene or naphthalene ring, preferably a benzene ring, P.sup.10 is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl, or alkyl of 1 to 4 carbon atoms substituted by alkoxy of 1 to 4 carbon atoms, such as methoxy, or by cyano, or is phenyl, preferably alkyl of 1 to 4 carbon atoms or phenyl, P.sup.11 is hydrogen, chlorine, bromine, sulfo, carbamoyl, methylsulfonyl, phenylsulfonyl, cyano or sulfoalkyl of 1 to 4 carbon atoms, preferably hydrogen, sulfo, sulfoalkyl having an alkyl radical of 1 to 4 carbon atoms, such as sulfomethyl, cyano or carbamoyl, B is alkylene of 1 to 4 carbon atoms, methylenephenylene, ethylenephenylene, phenylenemethylene, phenyleneethylene or phenylene or methylenephenylene, ethylenephenylene or phenylene substituted in the benzene radical by fluorine, chlorine, bromine, methyl, methoxy, cyano, sulfo, carboxy, acetyl, nitro, carbamoyl and/or sulfamoyl and D.sup.1 is a radical of the formula (4a) or (4b). Radicals --K.sup.2 --Z of coupling components of the formula H--K.sup.2 --Z, or their starting amino compounds H--K.sup.2 --N(R.sup.A)H or H--K.sup.2 --Q--W--N(R)H (Z being here --N(R.sup.A)H or --N(R)H) into which the fiber-reactive radical of the formula (2a) ##STR11## (with G, R.sup.B, W.sup.A and R having the abovementioned meaning) or the 5,6-difluoropyrimidin-4-yl radical has to be introduced subsequently, are, for example, radicals of the formulae (9a) to (9h) ##STR12## in which P.sup.1, P.sup.2, P.sup.9, P.sup.10, P.sup.11, B, T, M, m and Z have the particularly preferred meanings indicated above, and D.sup.5 as a radical of a diazo component is a radical of the abovementioned and defined formula (6a) or (6b). In the above formulae (8a), (8b) and (9a), the free bond which leads to the azo group is bonded to the aromatic nucleus in the ortho position relative to the hydroxy group. Radicals K.sup.3 in the formulae (3h) and (3i) having a metal complex-binding oxygen atom are in particular those of the formulae (10a) to (10e) ##STR13## in which the individual formula members have one of the abovementioned meanings and P* is hydrogen or a radical Z or a group of the formula --N.dbd.N--K.sup.2 --Z or --N.dbd.N--K--H with K.sup.2, Z and K having the abovementioned meaning. Of the azo dyes, those are furthermore preferred which correspond to the formulae (11A) to (11Z), (11AA) and (11AB) ##STR14## in which: Z.sup.1 is a radical of the abovementioned and defined formula (2a) or the 5,6-difluoropyrimidin-4-yl radical; M has one of the abovementioned meanings; D is a benzene ring or is a naphthalene ring, where the azo group is preferably bonded to the naphthalene ring in the .beta.-position and where in the case in which D is the naphthalene ring R.sup.2 and R.sup.3 are preferably each, independently of one another, a hydrogen atom or a sulfo group; R.sup.1 is hydrogen or sulfo or a group Y--SO.sub.2 --W.sup.o -- of the abovementioned meaning; R.sup.2 is hydrogen, alkyl or 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, halogen, such as chlorine and bromine, carboxy or sulfo and is preferably hydrogen, methyl, methoxy, bromine, chlorine, sulfo or carboxy and particularly preferably hydrogen, methoxy or sulfo; R.sup.3 is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and in particular methoxy, halogen, such as chlorine and bromine, nitro, carboxy or sulfo, preferably hydrogen, methyl, methoxy, chlorine, carboxy, sulfo or acetylamino and particularly preferably hydrogen, methoxy or sulfo; R.sup.4 is hydroxy or amino, preferably hydroxy; R.sup.5 is methyl, carboxy, carbomethoxy or carbethoxy, preferably methyl or carboxy; R.sup.6 is acetylamino, propionylamino, ureido or methyl; R.sup.7 is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, halogen, such as bromine and in particular chlorine, preferably hydrogen, methyl, ethyl, methoxy or ethoxy; R.sup.8 is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkanoylamino of 2 to 5 carbon atoms, such as acetylamino and propionylamino, or ureido, preferably hydrogen, methyl, ethyl, methoxy, ethoxy, acetylamino or ureido; R.sup.9 is hydrogen, cyano, carbamoyl, sulfamoyl or sulfomethyl, preferably hydrogen or carbamoyl; R.sup.21 has one of the meanings of R.sup.1 ; R.sup.22 has one of the meanings of R.sup.2 ; R.sup.23 has one of the meanings of R.sup.3 ; ALK is alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, or alkyl of 2 to 4 carbon atoms, such as ethyl and propyl, which can be substituted by hydroxy, carboxy, sulfo or sulfato; G.sup.1 is alkylene of 1 to 4 carbon atoms, such as ethylene and propylene, or is phenylene or phenylene substituted by sulfo, carboxy and/or alkyl of 1 to 4 carbon atoms, such as methyl; G.sup.2 is a group of the formula --NH-alk-, --NH-phen- or -alk-, in which alk is alkylene of 2 to 4 carbon atoms and phen is sulfophenylene or phenylene; x is the number zero or 1; m is the number zero, 1 or 2 (where if m is zero this group is hydrogen); p is the number zero or 1 (where if p is zero this group is hydrogen); in the compounds of the formulae (11A), (11F), (11N) and (11V) the amino or amido group in the 2- or 3-position is bonded to the 8-naphthol radical, and in the compounds of the formulae (11C), (11D), (11L), (11M), (11R) and (11U) one group --SO.sub.3 M is bonded in the meta- or para-position relative to the amino or acylamino group. Heavy metal complex azo dyes of particular importance are, for example, the 1,2-chromium complex and 1,2-cobalt complex and in particular the 1:1 copper complex monoazo compounds of the azo compounds of the following formulae (12A) and (12B): ##STR15## in which M, m and Z.sup.1 have the abovementioned particularly preferred meanings, and p is the number zero or 1 (where if p is zero this group is hydrogen). Of the phthalocyanine dyes according to the invention, those are preferred which correspond to the formula (13) ##STR16## in which Pc is the radical of an aluminum, nickel or preferably copper phthalocyanine; R.sup.o is an amino group of the formula --NR.sup.13 R.sup.14, in which R.sup.13 and R.sup.14 independently of one another are hydrogen or alkyl of 1 to 4 carbon atoms, which can be substituted by hydroxy or sulfo, or is a heterocyclic, N-containing radical, such as the morpholino or piperidino radical; R.sup.12 is a hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl and ethyl; G.sup.3 is phenylene optionally substituted by 1 or 2 substituents from the group consisting of alkyl of 1 to 4 carbon atoms, such as ethyl and methyl, halogen, such as chlorine and bromine, carboxy and sulfo, for example sulfophenylene, or is alkylene of 2 to 6 carbon atoms, such as ethylene; Z is the fiber-reactive group of the formula (2); a is a number from zero to 3, b is a number from zero to 3 and c is a number from 1 to 2, where the sum of (a+b+c) is a number from 2 to 4. Of these, those are particularly to be mentioned which correspond to the formulae (13a) and (13b) ##STR17## in which a is a number from 1 to 3, b is a number from 0 to 2 and c is a number from 1 to 2, where the sum of (a+b+c) is a number from 2 to 4, Pc is the radical of a nickel or preferably copper phthalocyanine and alk is alkylene of 2 to 4 carbon atoms, preferably ethylene, and Z.sup.1 has the above meaning. Copper formazan dyes according to the invention are in particular those which correspond to the formula (14) ##STR18## in which: Z.sup.1 has the abovementioned meaning; X.sup.1 is an oxygen atom or preferably the carbonyloxy group of the formula --COO--; P.sub.1 and P.sub.2 are, independently of one another, each a benzene or naphthalene ring, where the nitrogen atom and the group X.sup.1 are bonded to P.sub.1 in the ortho-position relative to one another and the oxygen atom and the nitrogen atom are bonded to P.sub.2 in the ortho-position relative to one another and the benzene nuclei or naphthalene nuclei can additionally be substituted by one or two substituents from the group consisting of halogen, such as chlorine, nitro, alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, sulfamoyl, sulfamoyl mono- or disubstituted by alkyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl, and phenylsulfonyl, where both P.sub.1 and P.sub.2 are preferably a benzene ring; P.sub.3 is a straight-chain or branched alkylene group of 2 to 6 carbon atoms, preferably of 2 to 4 carbon atoms, which can be substituted by a sulfophenyl group, or is a phenylene group or a naphthylene group which can be substituted by 1 or 2 substituents from the group consisting of methyl, ethyl, methoxy, ethoxy and chlorine, where P.sub.3 is preferably a benzene ring; T.sup.1, T.sup.2 and T.sup.3 are, independently of one another, each a sulfo or carboxy group, preferably sulfo group; e, f and g are, independently of one another, each the number zero, 1 or 2, where the sum of (e+f+g) is an integer from 1 to 4 and preferably 2 or 3, in particular 2, where if e or f or g is zero the group T.sup.1 or T.sup.2 or T.sup.3 is a hydrogen atom; k is the number 1 or 2, preferably 1, where the group --NH--Z.sup.1 can be bonded to an aromatic radical of P.sub.1, P.sub.2 or P.sub.3 and is preferably bonded to P.sub.2. Of the copper formazan dyes of the formula (14), those are preferred in which P.sub.1 and P.sub.2 are both a benzene ring, the group --NH--Z.sup.1 is bonded to P.sub.2 and T.sup.1 and T.sup.2 are each a sulfo group, where e and g both are the number 1. If the group --NH--Z.sup.1 is bonded to P.sub.1, e is the number zero, g is the number 2 and T.sup.2 is a sulfo group. The group --P.sub.3 --(T.sup.3).sub.f is furthermore preferably the phenyl or a 2- or 4-sulfophenyl radical. Of these, in particular those copper formazan dyes are to be emphasized which correspond to the formula (14a) ##STR19## in which M and Z.sup.1 have the abovementioned particularly preferred meanings. Of the triphendioxazine dyes according to the invention, those are to be emphasized which correspond to the formula (15) ##STR20## in which M and Z have one of the abovementioned meanings and the two sulfo groups --SO.sub.3 M are preferably bonded to the benzene nucleus in the ortho-position relative to the oxygen atom of the heterocyclic ring. Of the anthraquinone dyes according to the invention, those are particularly to be mentioned which correspond to the formula (16) ##STR21## in which M, Z and p have one of the abovementioned meanings and Ph is phenylene optionally substituted by 1 or 2 substituents from the group consisting of alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, halogen, such as chlorine and bromine, carboxy and sulfo, or is phenylene which is substituted by 3 or 4 methyl groups, or is cyclohexylene. The present invention furthermore relates to processes for the preparation of the dyes of the formula (1) according to the invention. They can be prepared in a manner which is customary per se analogously to known synthesis routes specific for the respective class of dye by reacting precursors typical of the respective dye, of which at least one contains one or two groups of the formula (2), with one another, or by reacting a compound of the formula (20) ##STR22## with Fb, R, Q, W and n having the abovementioned meanings with 4,5,6-trifluoropyrimidine in an equivalent amount, or by reacting a compound of the formula Fb--N(R.sup.A)H with Fb and R.sup.A having the abovementioned meaning, with a compound of the formula (21) ##STR23## in which Hal is halogen, such as fluorine and chlorine, and G, R.sup.B, W.sup.A and R have the abovementioned meanings, or by reacting a compound of the formula (22) ##STR24## with Fb, R.sup.A, G and Hal having the abovementioned meaning, with a compound of the formula (23) ##STR25## with R.sup.B, W.sup.A and R having the abovementioned meaning. In the condensation reactions, care is to be taken that the fiber-reactive groups are not damaged in the alkaline range. The reactions of the starting compounds are carried out in suspension or solution in aqueous or aqueous-organic medium. If the reactions are carried out in an aqueous-organic medium, the organic medium is, for example, acetone, dimethylformamide, dimethyl sulfoxide or N-methyl-pyrrolidone. Advantageously, the hydrogen halide liberated in the condensation is continuously neutralized by addition of aqueous alkali metal or alkaline earth metal hydroxides, carbonates or bicarbonates. The condensation reaction of the 4,5,6-trifluoropyrimidine is as a rule carried out at a temperature between -5.degree. C. and +50.degree. C., preferably at a temperature between 0.degree. C. and +40.degree. C., and at a pH between 2 and 11, preferably between 4 and 10. The reaction of the starting compounds of the formula Fb--N(R.sup.A)H and of the formula (21) is as a rule carried out at a temperature between -5.degree. C. and +60.degree. C., if Hal is fluorine preferably at a temperature between 0.degree. C. and 30.degree. C., and at a pH between 3 and 10, preferably between 6 and 9. The reaction of the compounds of the formulae (22) and (23) is as a rule carried out at a temperature between -5.degree. C. and +30.degree. C., if Hal is fluorine preferably at a temperature between 0.degree. C. and 30.degree. C., and at a pH between 3 and 10, preferably between 6 and 9. The starting compounds Fb--N(R.sup.A)H or of the formula (20) and their precursors are generally known and described in large numbers in the literature. The starting compounds of the formulae (21) and (23) can be prepared in a manner which is customary and known per se by reaction of a dihalo-s-triazine substituted by the substituent G with an amine of the formula H(R.sup.B)N--W.sup.A --N(R)H and then with 4,5,6-trifluoropyrimidine or by reaction of this diamino compound with 4,5,6-trifluoropyrimidine. The starting compound of the formula (22) is obtained analogously by procedures known per se by reaction of a compound of the formula Fb--N(R.sup.A)H of the abovementioned meaning with a dihalo-s-triazine substituted by the substituent G. Aromatic amines which serve as diazo components for the synthesis of the azo dyes of the formula (1) according to the invention and correspond to the formula D.sup.1 --NH.sub.2 are, for example: 1-amino-2-, -3- or -4-methoxybenzene, 1-amino-2-, -3- or 4-chlorobenzene, 1-amino-2,5-dichlorobenzene, 1-amino-2,5-dimethylbenzene, 1-amino-3-methyl-6-methoxybenzene, 1-amino-2-methoxy-4-nitrobenzene, 4-aminodiphenyl, 1-aminobenzene-2-, -3- or 4-carboxyic acid, 2-aminodiphenyl ether, 1-aminobenzene-2-, -3- or 4-sulfonic acid amide, -N-methylamide, -N-ethylamide, -N,N-dimethylamide or -N,N-diethylamide, dehydrothio-p-toluidinesulfonic acid, 1-amino-3-trifluoromethyl-6-sulfonic acid, 1-amino-3- or -4-nitrobenzene, 1-amino-3- or -4-acetylaminobenzene, 1-aminobenzene-2-, -3- or -4-sulfonic acid, 1-aminobenzene-2,4- and -2,5-disulfonic acid, 1-amino-4-methylbenzene-2-sulfonic acid, 1-amino-3-methylbenzene-6-sulfonic acid, 1-amino-6-methylbenzene-3- or -4-sulfonic acid, 1-amino-2-carboxybenzene-4-sulfonic acid, 1-amino-4-carboxybenzene-2-sulfonic acid, 1-amino4- or -5-chlorobenzene-2-sulfonic acid, 1-amino6-chlorobenzene-3- or -4-sulfonic acid, 1-amino-3,4-dichlorobenzene-6-sulfonic acid, 1-amino-2,5-dichlorobenzene-6-sulfonic acid, 1-amino-2,5-dichlorobenzene-4-sulfonic acid, 1-amino4-methyl-5-chlorobenzene-2-sulfonic acid, 1-amino-5-methyl-4-chlorobenzene-2-sulfonic acid, 1-amino-4- or -5-methoxybenzene-2-sulfonic acid, 1-amino-6-methoxybenzene-3- or -4-sulfonic acid, 1-amino6-ethoxybenzene-3- or -4-sulfonic acid, 1-amino-2,4-dimethoxybenzene-4-sulfonic acid, 1-amino-2,5-dimethoxybenzene-4-sulfonic acid, 1-amino-3-acetylaminobenzene-6-sulfonic acid, 1-amino-4-acetylaminobenzene-2-sulfonic acid, 1-amino-3-acetylamino-4-methylbenzene-6-sulfonic acid, 2-amino-1-methylbenzene-3,5-disulfonic acid, 1-amino-4-methoxybenzene-2,5-disulfonic acid, 1,4-diaminobenzene-2,5-disulfonic acid, 1-amino-3- or 4-nitrobenzene-6-sulfonic acid, 1-aminonaphthalene, 2-aminonaphthalene, 1-aminonaphthalene-2-, 4-, -5-, -6-, -7- or -8-sulfonic acid, 2-aminonaphthalene-3,6- or -5,7-disulfonic acid, 1-amino-naphthalene-3,6- or -5,7-disulfonic acid, 2-aminonaphthalene-1-sulfonic acid, 2-aminonaphthalene-1,5-, -1,7-, -3,6-, -5,7-, 4,8- or -6,8-disulfonic acid, 1-aminonaphthalene-2,5,7-trisulfonic acid, 2-aminonaphthalene-1,5,7-, 3,6,8- or 4,6,8-trisulfonic acid, 1-hydroxy-2-aminobenzene-4-sulfonic acid, 1-hydroxy-2-aminobenzene-5-sulfonic acid, 1-hydroxy-2-aminobenzene-4,6-disulfonic acid, 1-hydroxy-2-amino-4-acetylaminobenzene-6-sulfonic acid, 1-hydroxy-2-amino-6-acetylaminobenzene-4-sulfonic acid, 1-hydroxy-2-amino-4-chlorobenzene-5-sulfonic acid, 1-hydroxy-2-amino-4-methylsulfonylbenzene, 1-amino-2-hydroxy-6-nitronaphthalene-4-sulfonic acid, 2-amino-1-hydroxynaphthalene-4,8-disulfonic acid, 4-aminoazobenzene-3,4'-disulfonic acid, 3-methoxy-4-amino-6-methylazobenzene-2',4'-disulfonic acid, 3-methoxy-4-amino-6-methylazobenzene-2',5'-disulfonic acid, 2-(.beta.-sulfatoethylsulfonyl)aniline, 3-(.beta.-sulfatoethylsulfonyl)aniline, 4-(.beta.-sulfatoethylsulfonyl)aniline, 2-carboxy-5-(.beta.-sulfatoethylsulfonyl)aniline, 2-chloro-3-(sulfatoethylsulfonyl)aniline, 2-chloro-4-(.beta.-sulfatoethylsulfonyl)aniline, 2-bromo-4-(.beta.-sulfatoethylsulfonyl)aniline, 4-methoxy-3-(.beta.-sulfatoethylsulfonyl)aniline, 4-chloro-3-(.beta.-sulfatoethylsulfonyl)aniline, 2-ethoxy-4- or -5-(.beta.-sulfatoethylsulfonyl)aniline, 2-methyl-4-(.beta.-sulfatoethylsulfonyl)aniline, 2-methoxy-5- or 4-(.beta.-sulfatoethylsulfonyl)aniline, 2,4-diethoxy-5-(.beta.-sulfatoethylsulfonyl)aniline, 2,4-dimethoxy-5-(.beta.-sulfatoethylsulfonyl)aniline, 2,5-dimethoxy-4-(.beta.-sulfatoethylsulfonyl)aniline, 2-methoxy-5-methyl-4-(.beta.-sulfatoethylsulfonyl)aniline, 2- or 3- or 4-(.beta.-thiosulfatoethylsulfonyl)aniline, 2-methoxy-5-(.beta.-thiosulfatoethylsulfonyl)aniline, 2-sulfo-4-(.beta.-phosphatoethylsulfonyl)aniline, 2-sulfo-4-vinylsulfonylaniline, 2-hydroxy-4- or -5-(.beta.-sulfatoethylsulfonyl)aniline, 2-chloro-4- or -5-(.beta.-chloroethylsulfonyl)aniline, 2-hydroxy-5-(.beta.-sulfatoethylsulfonyl)aniline, 2-hydroxy-3-sulfo-5-(.beta.-sulfatoethylsulfonyl)aniline, 3- or 4-(.beta.-acetoxyethylsulfonyl)aniline, 6-carboxy-1-sulfo-2-aminonaphthalene, 5-(.beta.-sulfatoethylsulfonyl)-2-aminonaphthalene, 6- or 7- or 8-(.beta.-sulfatoethylsulfonyl)-2-aminonaphthalene, 6-(.beta.-sulfatoethylsulfonyl)-1-sulfo-2-aminonaphthalene, 5-(.beta.-sulfatoethylsulfonyl)-1-sulfo-2-aminonaphthalene, 8-(.beta.-sulfatoethylsulfonyl)-6-sulfo-2-aminonaphthalene, 4-[N-methyl-N-(.beta.-sulfatoethylsulfonyl)]aminoaniline, 3-[N-methyl-N-(.beta.-sulfatoethylsulfonyl)]aminoaniline, 4-[.beta.-(.beta.-sulfatoethylsulfonyl)ethyl]aniline, 3- or 4-[.beta.-(.beta.'-chloroethylsulfonyl)ethylamino]aniline, 3- or 4-[.beta.-(.beta.'-sulfatoethylsulfonyl)ethylamino]aniline, 3- or 4-[.gamma.-(.beta.'-chloroethylsulfonyl)propylamino]aniline, 3- or 4-[.gamma.-(.beta.'-sulfatoethylsulfonyl)propylamino]aniline and 3- or 4-[.gamma.-(vinylsulfonyl)propylamino]aniline. Starting compounds corresponding to the formula H(R)N--W--Q--D.sup.2 --NH.sub.2 are, for example, 1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-diamino-4-chlorobenzene, 1,3-diamino-4-methylbenzene, 1,3-diamino-4-ethylbenzene, 1,3-diamino-4-methoxybenzene, 1,3-diamino-4-ethoxybenzene, 1,4-diamino-2-methylbenzene, 1,4-diamino-2-methoxybenzene, 1,4-diamino-2-ethoxybenzene, 1,4-diamino-2-chlorobenzene, 1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2,5-diethylbenzene, 1,4-diamino-2-methyl-5-methoxybenzene, 1,4-diamino-2,5-dimethoxybenzene,1,4-diamino-2,5-diethoxybenzene, 2,6-diaminonaphthalene, 1,3-diamino-2,4,6-trimethylbenzene, 1,4-diamino-2,3,5,6-tetramethylbenzene, 1,3-diamino-4-nitrobenzene, 4,4'-diaminostilbene, 4,4'-diaminodiphenylmethane, 4,4'-diaminobiphenyl (benzidine), 3,3'-dimethylbenzidine, 3,3'-dimethoxybenzidine, 3,3'-dichlorobenzidine, 3,3'-dicarboxybenzidine, 3,3'-dicarboxymethoxybenzidine, 2,2'-dimethylbenzidine, 4,2'-diaminodiphenyl (diphenyl), 2,6-diaminonaphthalene-4,8-disulfonic acid, 1,4-diaminobenzene-2-sulfonic acid, 1,4-diaminobenzene-2,5-disulfonic acid, 1,4-diaminobenzene-2,6-disulfonic acid, 1,3-diaminobenzene-4-sulfonic acid, 1,3-diaminobenzene-4,6-disulfonic acid, 1,4-diamino-2-chlorobenzene-5-sulfonic acid, 1,4-diamino-2-methylbenzene-5-sulfonic acid, 1,5-diamino-6-methylbenzene-3-sulfonic acid, 1,3-diamino-6-methylbenzene-4-sulfonic acid, 3-(3'- or 4'-aminobenzoylamino)-1-aminobenzene-6-sulfonic acid, 1-(4'-aminobenzoylamino)-4-aminobenzene-2,5-disulfonic acid, 1,4-diaminobenzene-2-carboxylic acid, 1,3-diaminobenzene4-carboxylic acid, 1,2-diaminobenzene-4-carboxylic acid, 1,3-diaminobenzene-5-carboxylic acid, 1,4-diaminobenzene-2-methylbenzene, 4,4'-diaminodiphenyl oxide, 4,4'-diaminodiphenylurea-2,2'-disulfonic acid, 4,4'-diaminodiphenyloxyethane-2,2'-disulfonic acid, 4,4'-diaminostilbene-2,2'-disulfonic acid, 4,4'-diaminodiphenylethane-2,2'-disulfonic acid, 2-amino-5-aminomethylnaphthalene-1-sulfonic acid, 2-amino-5-aminomethylnaphthalene-1,7-disulfonic acid, 1-amino-4-methoxy-5-aminomethylbenzene-6-sulfonic acid, 1-amino-4-methyl-5-aminomethylbenzene-6-sulfonic acid, 4,4'-diaminodiphenyl-3-sulfonic acid, 1,4-diaminonaphthalene-6-sulfonic acid, 1,4-diamino-naphthalene-2-sulfonic acid, 2,6-diaminonaphthalene-4,8-disulfonic acid and 2,6-diaminonaphthalene-8-sulfonic acid. Starting compounds which serve for the preparation of disazo dyes of the formula (1) according to the invention first as a coupling component and then, in the form of the amino azo compound formed, as a diazo component and correspond to the formula H--E--NH.sub.2 are, for example, aniline, 3-methylaniline, 2-methoxy-5-methylaniline, 2,5-dimethylaniline, 3-ureidoaniline, 3-acetylaminoaniline, 3-propionylaminoaniline, 3-butyrylaminoaniline, 3-methoxyaniline, 2-methyl-5-acetylaminoaniline, 2-methoxy-5-acetylaminoaniline, 2-methoxy-5-methylaniline, 3-(hydroxyacetylamino)aniline, 1,3-diaminobenzene-4-sulfonic acid, 1-aminonaphthalene-6-, -7- or -8-sulfonic acid, 1-amino-2-methoxy-naphthalene-6-sulfonic acid, 2-amino-5-hydroxynaphthalene-7-sulfonic acid, 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid, 2-amino-8-hydroxynaphthalene-6-sulfonic acid, 2-(4'-aminobenzoylamino)-5-naphthol-7-sulfonic acid, 1-(4'-amino-2'-sulfophenyl)-3-methyl-5-pyrazolone, 1-(4'-amino-2'-sulfophenyl)-3-carboxy-5-pyrazolone and N-(acetoacetyl)-3-sulfo-4-aminoanilide. Starting compounds for the preparation of the azo compounds of the formula (1) according to the invention which can serve as coupling components and correspond to the formula H--K.sup.1 or H--K.sup.2 --Q--W--N(R)H or H--K--H are, for example: phenol, 1-hydroxy-3- or 4-methylbenzene, 1-hydroxybenzene-4-sulfonic acid, 1-hydroxynaphthalene, 2-hydroxynaphthalene, 2-hydroxynaphthalene-6- or -7-sulfonic acid, 2-hydroxynaphthalene-3,6- or 6,8-disulfonic acid, 1-hydroxynaphthalene-4-sulfonic acid, 1-hydroxynaphthalene-4,6- or 4,7-disulfonic acid, 1-amino-3-methylbenzene, 1-amino-2-methoxy-5-methylbenzene, 1-amino-2,5-dimethylbenzene, 3-aminophenylurea, 1-amino-3-acetylaminobenzene, 1-amino-3-hydroxyacetylaminobenzene, 1,3-diaminobenzene-4-sulfonic acid, 1-aminonaphthalene-6- or -8-sulfonic acid, 1-amino-2-methoxynaphthalene-6-sulfonic acid, 2-aminonaphthalene-5,7-disulfonic acid, 1-amino-8-hydroxynaphthalene-6-sulfonic acid, 1-amino-8-hydroxynaphthalene-2,4-disulfonic acid, 2-hydroxy-3-aminonaphthalene-5,7-disulfonic acid, 1-amino-8-hydroxynaphthalene-2,4,6-trisulfonic acid, 1-hydroxy-8-acetylaminonaphthalene-3-sulfonic acid, 1-benzoylamino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 2-benzoylamino-5-hydroxynaphthalene-7-sulfonic acid, 2-amino-5-hydroxynaphthalene-7-sulfonic acid, 2-methyl- and 2-ethylamino-5-hydroxynaphthalene-7-sulfonic acid, 2-(N-acetyl-N-methylamino)-5-hydroxynaphthalene-7-sulfonic acid, 2-acetylamino-5-hydroxynaphthalene-7-sulfonic acid, 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid, 2-amino-8-hydroxynaphthalene-6-sulfonic acid, 2-methyl- or ethylamino-8-hydroxynaphthalene-6-sulfonic acid, 2-(N-acetyl-N-methylamino)-8-hydroxynaphthalene-6-sulfonic acid, 2-acetylamino-8-hydroxynaphthalene-6-sulfonic acid, 2-amino-8-hydroxynaphthalene-3,6-disulfonic acid, 2-acetylamino-8-hydroxynaphthalene-3,6-disulfonic acid, 1-amino-5-hydroxynaphthalene-7-sulfonic acid, 1-amino-8-hydroxynaphthalene3,6- or -4,6-disulfonic acid, 1-acetylamino-8-hydroxynaphthalene-3,6- and -4,6-disulfonic acid (1-(4'-aminobenzoylamino)-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-(4'-nitrobenzoylamino)-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-(3'-aminobenzoylamino)-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-(3'-nitrobenzoylamino)-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 2-(4'-amino-3'-sulfophenylamino)-5-hydroxynaphthalene-7-sulfonic acid, 3-methylpyrazolone-(5), 1-phenyl-3-methyl-5-pyrazolone, 1-(4'-sulfophenyl)-3-methyl-5-pyrazolone, 1-(4'-sulfophenyl)pyrazolone-(5)-3-carboxylic acid, 1-(3'-aminophenyl)-3-methyl-5-pyrazolone, 1-(2',5'-disulfophenyl)-3-methyl-5-pyrazolone, 1-(2'-methyl-4'-sulfophenyl)-5-pyrazolone-3-carboxylic acid, 1-(4',8'-disulfonaphthyl-[2']-3-methyl-5-pyrazolone, 1-(5',7'-disulfonaphthyl-[2']-3-methyl-5-pyrazolone, 1-(2',5'-dichloro-4'-sulfophenyl)-3-methyl-5-pyrazolone, 3-aminocarbonyl-4-methyl-6-hydroxypyrid-2-one, 1-ethyl-3-cyano- or -3-chloro-4-methyl-6-hydroxypyrid-2-one, 1-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyridone-2,2,4,6-triamino-3-cyanop yridine, 2-(3'-sulfophenylamino)-4,6-diamino-3-cyanopyridine, 2-(2'-hydroxyethylamino-3-cyano-4-methyl-6-aminopyridine, 2,6-bis(2'-hydroxyethylamino)-3-cyano-4-methylpyridine, 1-ethyl-3-carbamoyl-4-methyl-6-hydroxypyrid-2-one, 1-ethyl-3-sulfomethyl-4-methyl-5-carbamoyl-6-hydroxypyrid-2-one, N-acetoacetylaminobenzene, 1-(N-acetoacetylamino)-2-methoxybenzene-5-sulfonic acid, 4-hydroxyquinol-2-one, 1-amino-8-hydroxy-7-(phenylazo)naphthalene-3,6-disulfonic acid, 1-amino-8-hydroxy-7-(4'-sulfophenylazo)naphthalene-3,6-disulfonic acid, 1-amino-8-hydroxy-7-(2',5'-disulfophenylazo)naphthalene-3,6-disulfonic acid, 1-[4'-(.beta.-sulfatoethylsulfonyl)phenyl]-3-methyl-5-pyrazolone, 1-[4'-(vinylsulfonyl)phenyl]-3-methyl-5-pyrazolone, 1-[4'-(.beta.-sulfatoethylsulfonyl)phenyl]-3-carboxy-5-pyrazolone, 1-[3'-[.beta.-chloroethylsulfonyl)benzoylamino]-3,6-disulfo-8-naphthol, 1-[3'-(vinylsulfonyl)benzoylamino]-3,6-disulfo-8-naphthol, 1-[3'-(vinylsulfonyl)benzoylamino]-4,6-disulfo-8-naphthol, 1-[3'-(.beta.-sulfatoethylsulfonyl)benzoylamino]-4,6-disulfo-8-naphthol, 2-[3'-(.beta.-chloroethylsulfonyl)benzoylamino]-6-sulfo-8-naphthol, 2-[3'-(vinylsulfonyl)benzoylamino]-6-sulfo-8-naphthol, 3-[3'-(.beta.-chloroethylsulfonyl)benzoylamino]-6-sulfo-8-naphthol, 3-[3'-(vinylsulfonyl)benzoylamino]-6-sulfo-8-naphthol, 6-sulfo-1-[3'-(.beta.-chloroethylsulfonyl)benzoylamino]naphthol, 7-sulfo-[3'-(vinylsulfonyl)benzoylamino]naphthol, 2-[N-methyl-N-(.beta.-sulfatoethylsulfonyl)amino]-6-sulfo-8-naphthol, 3-[N-methyl-N-(.beta.-sulfatoethylsulfonyl)amino]-6-sulfo-8-naphthol, 2-[N-ethyl-N-(.beta.-sulfatoethylsulfonyl)amino]-6-sulfo-8-naphthol, 1-[N'-(3'-.beta.-chloroethylsulfonylphenyl)ureido]-3,6-disulfo-8-naphthol, 1-[N'-(3'-vinylsulfonylphenyl)ureido]-3,6-disulfo-8-naphthol, 1-[N'-(3'-vinylsulfonylpropyl)ureido]-3,6-disulfo-8-naphthol, 1-[N'-(3'-.beta.-chloroethylsulfonylphenyl)ureido]-4,6-disulfo-8-naphthol, 1-[N'-(3'-vinylsulfonylphenyl)ureido]-4,6-disulfo-8-naphthol, 1-[N'-(3'-.beta.-chloroethylsulfonylpropyl)ureido]-4,6-disulfo-8-naphthol, 2-[N'-(3'-.beta.-sulfatoethylsulfonylphenyl)ureido]-6-sulfo-8-naphthol, 2-[N'-(3'-chloroethylsulfonylpropyl)ureido]-6-sulfo-8-naphthol, 3-[N'-(3'-.beta.-chloroethylsulfonylphenyl)ureido]-6-sulfo-8-naphthol, 3-[N'-(3'-vinylsulfonylpropyl)ureido]-6-sulfo-8-naphthol, 2-sulfo-5-[N'-(3"-.beta.-chloroethylsulfonyl)phenyl]ureidoaniline, 3-[N'-(3"-.beta.-sulfatoethylsulfonyl)phenyl]ureidoaniline and 6-sulfo-1-[N'-(3"-.beta.-sulfatoethylsulfonyl)phenyl]ureido-8-naphthol. |
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