DE1544542A1 - Reactive dyes and processes for their preparation - Google Patents

Description

Reactive dyes and processes for their preparation The present invention relates to valuable new reactive dyes of the general composition in this formula, F denotes the remainder of an organic one Dye, X a grouping - -, -S02-, -Asylene -, - -Alkylene- or -N = N-, which directly with the radical A and either directly or via another pontic is linked to the radical F, where R is hydrogen or a substituent, "asylene" for an arylene radical and "alkylene" represents a lower alkylene radical ; A means that. Residue of a 6-membered heterocyclic Ring containing at least one reactive sulfonyl tuenten on a carbon atom of the heterocyclic Ring contains bound and the condensed may have aromatic rings, and m is a number from 0.5 to B. In the dyes of the general formula I, the radical A is by definition, via the remainder X with the paraffin remainder F links, where the remainder X in turn either directly or via Another bridge member is bound to the dye residue F. The bridge members X are nitrogen-containing bridge members preferred, in particular -NH- and -N (CH3) groups as well as R. Sulfonamide or carbonamide groups. The amino or amide groups can carry further substituents, such as lower alkyl (preferably C 1 to C5), aralkyl, cycloalkyl or aryl groups, but are preferably in the non- substituted -NH- form. The amino groups -N (R) -are linked directly to the radical A on the one hand and can either directly or via a further bridge member, such as -S02- or -CO- (as in the case of the amide group already mentioned) or via a Alkylene group, an alkylene-C0-, an arylene, arylene-S02-, arylene-C0-, aryleneamino or aralkyleneamino group, a urea grouping or a triazine or diazine ring, an arylenamidosulfonyl group or other types of members may be bonded to an aromatic ring of the dye F. . If such further bridge members contain heterocyclic ring systems, as in the case of triazinyl or pyrimidinyl radicals, then these too can still have reactive atoms or groups, such as halogen atoms or sulfonyl substituents. The other possible bridge members -SO2-, alkylene and arylene are on the one hand bound directly to the retrocycle A and can be linked on the other hand either directly or via further bridge members to the radical F ; if there are further bridge members between these radicals X and F, the following groupings result, for example: -OC-arylene-A; -OC-alkylene-A; -OC-aralkylene-A; -OC-alkarylene-A; -02S-arylene-A; -02S-alkylene-A; -02S-aralkylene-A; -02S-alkarylene-A, - (R) N-alkylene A; - (R) N-aralkylene-A; - (R) N-alkarylene-A; - (R) N-arylene-A; - (R) NO2S-alkylene-A; - (R) NO 2S-Aralkyien-A; - (R) NO2S-alkarylene-A; - (R) NO2 S-Arylene-A; - (R) N-OC-alkylene-A; - (R) N-0C-aralkylene-A; - (R) N-0C-alkarylene-A; - (R) N-OC-arylin-A; @ - h = N-aralkylene-A; -NN = arylene-A; - (R) N02S-Al The reactive sulfonyl substituents in radical A are lower alkylsulfonyl radicals with preferably 1 - 5 carbon atoms, such as methylsulfonyl, ethylsulfonyl or propylsulfonyl radicals, arylsulfonyl radicals, such as phenylsulfonyl, p-toluenesulfonyl radicals, p-toluenesulfonyl radicals Aralkylsulphonyl radicals, such as benzylsulphonyl and p-toluylmethylsulphonyl radicals, and also heterosulphonyl radicals, such as 2-benzothiazolesulphonyl, are possible: The 6-membered heterocyclic ring A, which has at least one reactive, ie, under the known conditions of reactive dye use, is, for example, a monentenoazine-substituted sulfonyl -, diazine or triazine ring, such as a pyridine, pyrimidine, pyridazine, pyrazine, thiazine or as , Cinnoline, quinazoline, quinoxaline, acridine, phenazine or phenanthridine ring. The heterocyclic ring A is preferably one which, as in the above-mentioned compounds, contains one or more ring nitrogen atoms. Aas-fused rings are, by definition, of an aromatic nature; they can be carbocyclic or heterocyclic. The aaskondensed rings can be 5- or 6-membered. Of particular interest are pyrimidine and sym. Triazine rings A. The binding of the heterocyclic ring A to X either starts from the heterocyclic ring which bears the reactive sulfonyl substituent (s), or the bond starts from an optionally aas-fused carbocyclic or heterocyclic ring system. in the event that the bridge member X starts from the heterocyclic ring which has the reactive sulfonyl substituent (s), X is linked to either a carbon atom or a heteroatom, among these generally a nitrogen atom of the heterocyclic 6-membered ring. X is preferably bonded to a carbon atom of the hetero ring A. Examples of suitable heterocyclic rings A which have at least one reactive sulfonyl group and which may contain further rings fused on are: 2-carboxymethylsulfonyl-4-pyrimidinyl, 2-methylsulfonyl-4-methyl-6-pyrimidinyl 2- Phenylsulfonyl-4-methyl-6-pyrimidinyl-, 2-phenylsulfonyl-4-methyl-5-chloro-6-pyrimidinyl-, 2,4-bis-methylaulfonyl-6-pyrimidinyl-, 2,4-bis-methylaulfonyl-5 -aulfamidyl-pyrimidine, 3-phenylsulfonyl-6-pyridazinyl-, 3-methylaulfonyl-4-methyl-6-pyridazinyl-, 2,5-bis-methylsulfonyl = 6-pyrazinyl, 1-methylsulfonyl-3-triazinyl-, 1- Methylaulfonyl-3- (3'-sulfophenylamino) -5-triazinyl-, 1-methylsulfonyl-3- (2'-hydroxyethylamino) -5-triazinyl, 1-methylaulfonyl-3-amino-5-triazinyl-, 1-methylsulfonyl- 3-methoxy-5-triazinyl-, 1-methylsulfonyl-3- (2'-benzthiazolyl) -thio-5-triazinyl-, 1- (4'-methylphenylsulfonyl) -3-phenyl-5-triazinyl-, also 2- Methylsulfonyl-4-quinazolyl-, 2-methylsulfonyl-4-pyrimidinyl-2-phenylsulfonyl-4-pyrimidinyl, 2-1'4ethyls ulfony1-4-methyl-6-pyrimidinyl, 2-methylsulfonyl-4-methyl-5-chloro-6-pyrimidinyl, 2-carboxymethylsulfonyl-4-methyl-5-chloro-6-pyrimidinyl, 3- (4'- Nitrophenyl) sulfonyl-6-pyridazynyl 1,5-chloro-6-methylaulfonyl-4-pyridazinyl, 1-phenylsulfonyl-3-methoxy-5-triazinyl, 1,3-bis-phenylaulfonyl-5-triazinyl, 1-methyleulfonyl-3 -phenoxy-5-triazinyl, 1-methylaulfonyl-3-phenyl-5-triazinyl. The reactive sulfonyl substituent or substituents in the core A can be further substituted in the aryl, alkyl or hetero radicals by ionic or non-ionic groups, e.g. D. by carboxy (for example in the form of carboxymethyl), sulfo, hydroxy, nitro or halogen (C1, ßr) radicals, such as those in carboxy-methyisulfonyl, chloromethylsulfonyl, chloroethylsulfonyl, hydroxyethylsulfonyl -, nitrophenylsulfonyl, sulfophenylsulfonyl groups are present. The following examples should be mentioned from the large number of -XA groups: -NH-A, -N (CH @ _A, -N (C2H5) -A, -N (C3H7) -A, -CONH-A, -SO 2NH -A, -NFIO 2 SA, -CON (CH3) -A, -SO ? N (CH3) -A, - (CH3) -N02S-A, as well as the corresponding N-ethyl- and N-propylamides, -HN -CO-NH-A, -IIN-CH2-CO-NH-A, -N (CH3) -CH2-CONH-A, -HN-CH2-CH2-NH-'be and the corresponding N-alkyl (1-5 C) amides or amines and the corresponding N-alkyl (1-5 C) amides or amines of the compounds mentioned. Another suitable bridge member X is the azo group -N = N-. In a special case, the new dyes correspond to the formula F 1 '--- @ - N = NA), (II) where F., the remaining component of an azo dye , A has the meaning already given above, and k is the number 1 or 2; In this formula, F1 is, for example, the remainder of a coupling component; F1 can, however, also represent any other aromatic carbocyclic or heterocyclic radical which is used to build up the azo dye II, for example by condensation. The new dyes can belong to the most varied of classes , 2.B. the series of metal-free or metal-containing mono or polyazo dyestuffs, metal-free or metal-containing azaporphin dyestuffs, such as copper or Nickelphthalncyaninfarbstoffe, the Athrachinon-, Oaazin-, dioxazine, triphenylmethane - #, nitro, azomethine, benzanthrone and Dibenzanthranfarbstoffe and the polycyclic condensation compounds von anthraquinone, benzanthrone and dibenzanthrone compounds. As part of this Farbetoffklgesen are among other dyes of the folasnün general zuea mme neetsungen particularly valuable 1. Azo dyes where B and D represent aromatic, carbocyclic or heterocyclic radicals, in particular B the radical of a carbocyclic diazo component of the benzene or naphthalene series, and D the radical of an enol or phenolic coupling component, for example a 5-pyrazolone, an acetoacetic acid amide, an oxynaphthalene or an aminonaphthalene ; B and D can also have any substituents customary in azo carbates, including other azo groups; R stands for a substituent or preferably an hydrogen atom, Q stands for a direct bond or a group -SO2- and m 'stands for an integer, preferably the number 1 or 2; A is a 6-membered heterocyclic ring having at least one reactive sulfonyl substituent on a carbon atom bound form of the heterocyclic ring and which may have fused rings carbocyalisohe for the rest. Particularly valuable dyes of this series are adlche which are water-soluble, and in particular those which contain sulfonic acid and / or carboxylic acid groups. The azo dyes can be both metal-free and metal-containing, with the copper, chromium and cobalt complexes being of preferred interest among the metal complexes. Important azo dyes are, for example, those of the benzene-azo-naphthalene series, the benzene-azo-1-phenyl-5-pyrazolone series, the benzene-azo-aminonaphthalene series, the japhthalene-azanaphthalene series, the naphthalene-azo-1-phenylpyrazolone-5 series and the Stilbene-azo-benzene series, the dyes containing sulfonic acid groups being preferred here too. In the case of metal complex azo carbates, the metal complex bonded groups are preferably in the o-positions to the azo group, for example: B. in the form of ö, o'-dihydroxy, o hydzrozy-v'-carboxy, o-carboxy-o'-amino and o-hydroxy-o'-ßmiao-azo groups. 2. Anthraquinone dyes herein Z denotes hydrogen or subatituents, among these in particular the sulfonic acid group, p the number 1, 2 or 3, R1 is a substituent or preferably hydrogen, Q is a direct bond or a grouping -SO- and A a 6-membered heterocyclic ring, the mikestene a reactive sulfonyl substituent on a carbon atom of the heterocyclic ring has bonded and may contain fused carbocyclic rings. The water-soluble ones are also in the range of these dyes Products because of their excellent suitability for dyeing and Printing of cellulosic fibers is preferred, whereby the dyes substituted by sulfonic acid groups as prove particularly suitable. 3. Azaporphine dyes (Z) r d Pc 02NH- # ( CH Q i 1 with . In this formula, Pc stands for the remainder of a phthalocyanine, ine particular of a copper or nickel phthalocyanine or one Tetraphenyl copper or nickel phthalocyanine, Z for water substance or a substituent, the substituent being the Sulfonic acid group is preferred, r is the number 1 or 2, q for the number 0, 1 or 2, R for a substituent or preferably hydrogen, .Q for no direct bond or a -S02 grouping, A for a 6-membered heterocyclic Ring that has at least one reactive sulfonyl substituent has a carbon atom of the heterocyclic ring bonded and may contain further carbocyclic rings fused, and m ″ for a number from 0.5-4. The phthalocyanine residue Pc can of course have further substituents, in particular sulfonic acid and sulfonamide groups, such as —SO 2 NH 2, —SO 2 NH-alkyl, SO 2 N (alkyl) 2 and SO 2 NH (aryl) groups. . Water-soluble phthalocyanine of the formula V, -the are preferred for application to cellulose-containing materials, are in particular those which carry Where appropriate in the rest Pc and, in addition as a substituent Z sulfonic acid groups. The above compilation of a selection of suitable azo, anthraquinone and azaporphirifare and heterocyclic ring systems A represents a restriction of the general formulas, neither with regard to the preparative possibilities for the preparation of such Parbstoffe'in the context of general formula I, nor with regard to the valuable ones application properties of these products. The new dyes can also have any substituents customary in dyes, such as sulfonic acid, carboxylic acid, alkylamino, aralkylamino, arylamino, acylamino, nitro, cyano, halogen, H, hydroxy, alkoxy, Thioether, azo moieties and the like. The dyes can also contain other fixable groups, such as -mono- or dihalpgentriazinylamino-, mono-, di- or trihalopyrimidinylamino-, 2,3-dihaloquinoxaline-6-carbonyl- or -6-sulfonylamino-, 1,4-dihalophthalazine- 6-carbonyl or -6-sulfonylamino, 2-halobenzothiazole-5-earbonyl or -5-sulfonylamino, esterified sulfonic acid oxalkylamide and oxalkylsulfone groups, sulfofluoride, haloalkylamino, acryloylamino, haloacylamino groups and the like. The new dyes of the formula I are obtained by introducing at least one -XA group, in which X is a group, into dyes or paraffin precursors by processes known per se -S07, -arylene-, -alkylene- or -N = N- which is linked directly to the radical A and either directly or via a further bridge member to the radical F, where R is hydrogen or a substituent, "arylene "represents an arylene radical and" alkylene "represents a lower alkylene radical; A represents the remainder of a 6-membered heterocyclic ring; which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the heterocyclic ring and which may have fused aromatic rings ;. in the case of the use of Parb®toft preliminary products. these are converted into the desired final dyes . The introduction of the -XA group in dyes or paraffin precursors can be achieved by various preparative methods . For example, dyes containing amino or amide groups or parabellum precursors which have a reactive hydrogen atom on the amine or amide nitrogen can be mixed with compounds of the general formula A -Y (YI), wherein A represents a 6-membered heterocyclic ring, the at least one reactive sulfonyl substituent on one Contains carbon atom bonded to the heterocyclic ring and which have fused aromatic ranks, can, and Y represents an anionically detachable radical, implement and in the case of the use of paraffin precursors these in a suitable manner into the desired final dyes walk. Among the reactive radicals that can be split off as anionic radicals capable substituents Y have Cl, 8r and sulfonyl substituents preferred interest. Further suitable, anionically cleavable groups are, for example, F, SO 3M (M = H or metal cation), quaternary ammonium groups, alkyl merc # Lpto-, nitrile, alkoxy or aryloxy groups. Suitable heterocyclic compounds of the formula VI for the reaction are, for example, 2-carboxymethylsulfonyl-4-chloropyrimidine, 2-methylsulfonyl-6-methyl-4-chloropyrimidine, 2,4-bismethlysulfonyl-6-methylpyrimidine, 2,6-bis-phenylsulfonyl-4 methyl-5-chloropyrimidine, 2,4,6-tris-methylsulfonyl-pyrimidine, 2,4-bis-methylsulfonyl-pyrimidine-5-sulfonic acid chloride, 3,6-bisphenylsulfonyl-pyridazine, 3-methylsulfonyl-6-chloropyridazine , 3,6-bis-methylsulfonyl-4-methyl-pyridazine, 2,5,6-tris-methylsulfonyl-pyrazine, 1,3-bis-methylsulfonyl-2,4,6-triazine, 1,3-bis-methylsulfonyl -5- (3 ° -sulfophenylamino) -2,4,6-triazine, 193; biä-methyisulfonyl-5-phenoxytria: zin, 1,3-bis-methylsulfonyl-5-trichloroethoxy-triazine and numerous others in the 5-position substituted 1,3-bis-methylsulfonyl-2,4,6-triazines, 2,4-bismethylsulfonylquinazoline, 2,4-bis-phenylsulfonyl-quinoline, 2'-methylsulfonyl-4-chloropyrimidine, 2-chloromethylsulfonyl-4-chloropyrimidine, 2-phenylsulfonyl-4-chloropyrimidine, 2,6-bismethylsulfonyl-4-methyl-5-chloro pyrimidine, 2-methylsulfonyl-4-methyl-5,6-dichloropyrimidine, 2,6-bis-methylsulfonyl-4-methyl- = 5-bromo-pyrimidine, 2-methylsulfonyl-4-chloromethyl-5,6-dichloropyrimidine, 2 -Methylsulfonyl-4-methyl-6-chloropyrimidine-5-sulfonic acid chloride, 4,6-bis-methylsulfonyl-5-chloropyridazine and the bromine derivatives of the chlorine compounds mentioned. The reaction of dyes containing amino or amide groups or dye precursors with heterocyclic compounds of the formula VI is carried out, depending on the type of starting compounds used, in an organic, organic-aqueous or aqueous medium at temperatures from -10 ° C. to 800 ° C., preferably in the presence of alkaline condensing agents such as pyridine, aqueous alkali carbonate - or alkali hydroxide solutions. When paraffin intermediates are used, the condensation products obtained are converted into the desired end dyes in a manner customary per se. This process is of preferred interest for the preparation of azo carbates by initially using, for example, a diazo and / or coupling component which has a reactive amino or amide group. the reactive component VI is condensed and the intermediate product obtained is then converted into an azo dye by diazotization and / or coupling and / or condensation. In this, further conversion reactions can be carried out afterwards, as are customary in azo dyes, for example acylation, condensation, reduction and metallization reactions. Also in the preparation of other dyes, in particular such of the phthalocyanine and anthraquinone series, the condensation of a reactive component VI can first ER followed with an intermediate, for example with m-phenylenediamine or m-phenylenediaminesulfonic acid, the reaction product obtained thereafter with, for example bromaminic acid (1 -Amino-4-bromo-anthraquinone-2-eulfonic acid) are further condensed to a reactive anthraquinone dye or with copper or nickel phthalocyanine sulfonic acid halide to form a reactive phthalocyanine dye. A further variant for the preparation of the new dyes of the formula I is that one dyes containing amino or amide groups or, in particular, dye intermediates which än the amino @ or. Amide group have an exchangeable hydrogen atom, with compounds of the general formula A '(Z) t (VII), in which A' represents a 6-membered heterocyclic ring, which may contain further aromatic rings condensed, Z is an artionically cleavable radical, except represents a sulfonyl radical, and t is the number 2 or a number greater than 2, converts one of the radicals Z which can be split off by substitution, then converts the remaining Z radical (s) in a manner known per se into sulfonyl substituents and, if paraffin precursors are used, these into the transferred desired end dyes. The exchange of one or more substituents Z,. for example halogen atoms, against sulfonyl substituents can be achieved, for example, by reacting the compounds with alkyl or aryl sulfinates or, if X is, for example, an alkyl mercapto or aryl mercapto group that can be split off by artion, this with the aid of suitable oxidizing agents such as hydrogen peroxide, hypohalites or Permanganates, into the corresponding sulfonyl radicals. The dyes obtained by the various processes described can, as already mentioned for some cases, be subjected to further reactions customary for dyes, for example by using metallizable dyes with metal-releasing agents, in particular with chromium. Cobalt, copper or nickel salts, treated, dyes that have reducible groups, especially nitro groups, reduced, dyes that have acylatable groups, especially acylatable amino groups, acylated, or by subsequently treating dyes with sulfonating agents, such as chlorosulfonic acid , Thionyl chloride, oleum or SO3 in chlorinated hydrocarbons to introduce further sulfonic acid groups into the products. The last-mentioned process is sometimes of particular importance in the series of anthraquinone and phthalocyanine dyes. Depending on the number of reactive, preferably -HNR groups in the dye residue or in the paraffin precursors which are suitable for the conversion reaction, one or more groupings of the general formula -JC-A can be incorporated into the dyes. In the majority of cases, the number m 4 is not exceeded, but dyes, in particular those with a higher molecular weight structure, with more than 4, for example up to 8, groupings of the formula Z h can also be synthesized. If the dyes presented in accordance with the process contain metal- complex-forming groups, these can be influenced by metal-releasing agents, for example, of copper, nickel, chromium or Old cobalt transferred to their metal complex will. Deegames . you can: closer to the usual iendl. actions are subjected, such as diazotization, coupling, acylation and condensation reactions. For the reaction of dyes containing amino groups with reactive components A -Y of the formula (VI), for example, and in many cases preferred, iminoazo dyes of the formula in which B, D, Ri and m 'have the meanings already given, or aminoanthraquinone dyes of the formula in which Z, Ri and p have the meaning given, or phthalocvanine dyes of the formula containing amino groups where Pc, D, R1, q, r and m "have the meaning already given. The condensation products obtained correspond to the general formula (I) for the new dyes. They can be subjected to further ümwancüzngsreaktionen, in particular subsequent sulfation in the series of anthraquinone and phthalocyanine dyes is often of interest. Instead of using the pre-formed amino group-containing dyes of the formulas (VIII), (IX), (X) themselves, amino group-containing precursors can also be used for the preparation of such dyes, these first condense with the reactive component A. Y and then in a conventional manner further process the final dyes. Such a process via the paraffine intermediates is of outstanding interest in the preparation of azo dyes and of anthraquinone and phthalocyanine dyes. In the case of azo dyes, this is done by condensing a diazo component or a coupling component which has a reactive amino group with the reactive component of the formula (VI) and then building up the desired azo dye by coupling. This can then be re-metallized or diazotized and converted to a disaza or polyazo dye. In the case of anthraquinone dyes, for example, a diaminoaryl compound whose one amino group, for example acylamino compound, is protected on the second amino group with a reactive component (Y1) can be condensed, then the first protected amino group can be converted into the free amino group, for example by saponification, and the compound obtained with, for example Condense 1-amino-4-bromoanthraquinone-2-sulfonic acid to form a valuable anthraquinone dye type. For the preparation of phthalocyanine dyes, similarly to what has been stated for anthraquinone dyes, a diaminoaryl compound monocondensed with the reactive component A - Y can first be produced and this then condensed with, for example, copper or nickel phthalocyanine sulfonic acid halides, with other amino compounds such as ammonia, aliphatic at the same time or subsequently Amino compounds and / or aromatic amino compounds can also be used. Phthalocyaninesulfonamide dyes are obtained on this Wep-e which contain a certain proportion of sulfonarylamide groups which carry the reactive groups and, in addition, a certain proportion of non-reactive sulfonamide groups and / or free sulfonic acid groups. A Beenser's preferred group of reactive dyes within the scope of the compounds of the formula I has the composition In this formula, F is the residue of an organic dye, e is an amino group, A is the residue of a pyrimidine ring which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the heterocyclic ring, and m is a number from 0.5 to B. In the dyes the According to general formula (XI), the radical Al is linked to the dye test F via an amino group (X1). The amino group can carry further substituents, such as lower alkyl (preferably Ci to C5), aralkyl, cycloglkyl or asyl groups, but is preferably not in the further substituted Fons -NH-. The amino groups are in turn directly to an aromatic ring carbon atom of the dye bound. -Als come as reactive sulfonyl substituents in the pyrimidine ring lower alkylaulfonyl radicals with preferably 1 to 5 carbon atoms, such as Methylaultonyl, ethylaulfonyl or propylsulfonyl radicals, Arylaulfonyl radicals, such as phenylaulfonyl, p-toluenesulfonyl, p- Chlorophenylsulfonyl create, aralkylaulfonyl radicals, such as benzyl sultonyl and p-toluylmethylsulfonyl radicals, and also hetero- aultonyl radicals, such as 2-benzothiazolesulfonyl, in question. Ala suitable pyriaidin rings AI, the at least one reactive Have sulronyl substituents, for example: 2-carboxymethylsulfonyl-4-pyrimidinyl, 2-methylsultonyl-4- methyl-6-pyrimidinyl, 2-phenylsultonyl-4-methyl-6-pyrimidinyl, 2-phenylaulfonyl-4-methyl-5-chloro-6-pyrimidinyl, 2,4-bia- methylaulfonyl-6-pyrimidinyl, 2-methylsulfonyl-4-methyl-5- nitro-6-pyrimidinyl, 2-methylsulronyl-5-cyano-4-pyrimidinyl, 2-methylaultonyl-4-carboxy-6-pyrimidinyl or 2-ethylaultonyl- 5-aulfo-4-pyrimidinyl, as well as others already on page 4 called connections. The one or more present in the core Al reactive sulfonyl Substitutes can be ionogenic or non- ionogenic Groups weiteraubatitulert äein, z. B. by carboxy (both apielaweiae in the FORM of dsrboky »thyl-), hydroxy-, mitro-, Halogen (C1, Br), sulfonic acid or sultone radicals, or further ber-itä on. Groups mentioned on page 5. The new dyes of the formula (XI) can belong to a wide variety of classes, e.g. B. the series of metal-free or metal-containing mono- or polyazo dyes, metal-free or metal-containing azaporphin dyes, such as copper or nickel phthalocyanine dyes, the anthraquinone, oxazine, dioxazine, triphenyl methane, nitro, azamethine, benzanthrone and dibenzanthrone dyes and the polycyclic Condensation compounds of anthraquinone, benzanthrone and dibenzanthrone compounds. In the context of these dye substance classes, among other dyes of the following a11-common compositions are particularly valuable: 1. Azo dyes wherein B and D represent aromatic, carbocyclic or heterocyclic radicals, for example H the radical of an earbocyclic diazo component of the * Benaal or naphthalene series, and D the radical of an enolic or phenolic coupling component, e.g. B. a 5-pyrazolone, an acetoacetic acid arylamide , a ®xynaphthalins or an aminonaphthalene, etc .; B and D can also have any substituents customary in azo dyes , including further azo groups; R1 represents a substituent or preferably a hydrogen atom, m 'represents an integer , preferably the number 1 or 2; Al stands for the ester of a pyrimidine ring which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the ring. Particularly valuable dyes of this series are those which are water-soluble, and in particular those which have sulfonic acid and / or carboxylic acid groups. The azo dyes can be both metal-free and metal-containing, with the copper, chromium and cobalt complexes being of preferred interest among the metal complexes. Important azo dyes are, for example, those of the benzene-azo-naphthalene series, the benzene-azo-l-ptienyl-5-pyrazolone series, the naphthalene-azo-naphthalene series, the naphthalene-azo-1-phenylpyrazalone-5 series and the stilbenazo-benzene series, The dyes containing sulfonic acid groups are also preferred here. In the case of metal complex azo dyes, the metal complex-bonded groups are preferably in the o-positions to the azo group, e.g. B. in the form of o, o'-dihydroxy, o-hydroxy-o'-carboxy, o-carboxy-o'-amino and o-hydroxy-o'-aminoazo groups. 2. Anthraquinone dyes Here L denotes hydrogen or substituents, among these in particular the sulfonic acid group, p denotes the number 1, 2 or 3, R1 denotes a substituent or, preferably, hydrogen and aline pyrimidine ring which has at least one reactive sulfonyl substituent bonded to a carbon atom of the ring. Even. In the field of these dyestuffs, the water-soluble products are preferred because of their excellent suitability for dyeing and printing aellulose-containing fibers, the dyestuffs substituted by sulfonic acid groups proving to be particularly suitable. 3. Azaporphine dyes In this formula, Pc stands for the remainder of a phthalocyanine, e.g. B. a copper or nickel phthalocyanine or a tetraphenyl copper or nickel phthalocyanine, L for hydrogen or a substituent, the preferred substituent being the sulfonic acid group, r for the number 1 or 2, q for the number 0, 1 or 2, R1 for a substituent or, preferably, hydrogen, for a pyrimidine ring which has at least one reactive sulfonyl substituent bonded to a carbon atom of the ring and m ″ for a number from 0.5 to 4.

The phthalocyanine residue Pc can of course have further substituents, in particular sulfonic acid and sulfonide groups. Water-soluble phthalocyanine dyes of the formula (IV), which are preferred for application to cellulose-containing materials, are in particular those which have sulfonic acid groups in the Pc radical and, if appropriate, additionally as substituent L. The previous ones. Composition of a selection more suitable Aso-, anthranhinone and azaporphine dyes - as well as heterofLisaher- d Ringspsteee Al does not represent a restriction of the general porosity, and neither with regard to the preparative possibilities Representation of such dyes in the context of the general formula (Il still hinatahtli @ h the valuable application technology properties of these products. Particularly valuable dyes from the point of view of application technology are those of the general formulas (XII), (XIII) and (XIV), in to which the radical -N-Al corresponds to the following specified formula: R @, wherein R'1 represents one containing 1 to 3 carbon atoms lower alkyl radical or hydrogen, one of the Residues R3 or R4 for the group -302b! stands in which M denotes an alkyl, aralkyl or aryl radical which other of the radicals R3 or R4 also represent a group -S02M or hydrogen, A-alkyl, aralkyl ,, Ary1, -SOSH, -CO0R, -COÖ-Alkylj -Cl, -8r or -CM and R5 is hydrogen or a substituent, such as Alkyl, aralkyl, aryl, -SO-COOHp -C00-Alkrl, -C1, -8r, -CN, Nitro., Carbonuid or Sulfonamid. Those dyes of the formulas (XII), (XIII) and (XIV) in which the remainder s is a 2-methylsulfonyl-5-chloro-6-methylpyrimidinyl-4 radical. This residue is introduced by reacting the dyes containing amino groups with, for example, 2-methylsulfonyl-4,5-dichloro-6-methylpyrimidine. Incidentally, the new dyes (XI) can also contain any in RaRb m toffen Customary substituents, such as sulfonic acid, Carboxylic acid, alkylamino, aralkylamino, arylamino, acylamino, Hitro, cyano, halogen, hydroxy, alkoxy, thioether, azo groupings and the like. The dyes can otherwise other fixable groupings, such as mono- or dihalogen- triazinylaeino-, Kono-, D1- or trihalopyrimidinylamino-, 2,3-Dihaloquinoxaline-6-carbonyl- or -6-sulto n ylamino-,, 1 ', 4- Dihalophthalazine-6-carbonyl- or -6-sulfonylamino-, 2-halogen- bornzthiazole-5-carbonyl- or -5-sultonylamino-, esterified sulfone säureoxa L ky1awid- and Oxalkyl®ulfongruppen, Sulrofluorid-, halogen a M y1asino, acryloylamino, haloacylamino groups and the like exhibit. The new dyes of the formula (XI) are obtained by introducing at least one pyrimidinylamino group into dyes or dye precursors by processes known per se, which contains at least one reactive Sul.fonyl substituent bonded to a carbon atom of the pyrimidine ring and which is bonded to the nitrogen atom of the amino group is attached to a ring carbon atom of an aryl nucleus of the dye or dye precursor, and in case of using converts dye precursors into the desired final dyes .. the at least one reactive Sulfonylsubatituenten containing Pyrimidinylaminorest can sicrr in the dyes or Farbatoffvorprodukte for example, by introducing in that aminogruppenha.ltige Dyes or dye precursors which have a reactive hydrogen atom on the amine nitrogen , with compounds of the general formula Al- Y (XYI) in which Aleinen represents a pyrimidine ring which has at least one reactive sulphone contains yl substituents bound to a carbon atom of the heterocyclic ring, and Y denotes an anionically cleavable radical . Among the reactive substituents Y which can be cleaved as anionic radicals , Cl, Br and sulfonyl substituents have preferred itereases. Further suitable anionically cleavable radicals are, for example, F, So 3M (M = H or metal cation), quaternary ammonium groups, alkyl mercapto, nitrile, alkoxy or aryloxy groups. A very particularly preferred reactive component of the formula Aj-Y is 2-methylsulfonyl-4,5-dichloro-6-methylpyrimidine, on its condensation with dyes or dye precursors containing amino groups the surprisingly 4-position chlorine substituent against the remainder is exchanged .

Heterocyclic compounds of the formula (XVI) suitable for the reaction are, for example, 2-carboxymethylsulphonyl-4- chloropyrimidine, 2-methylsulphonyl-6-methyl-4-chloro-pyrimidine, 2,4-bismeth; ylsulphonyl-6-methyl-pyrimidine, 2 , 6-bis-phenylsulfonyl-4-methyl-5-chloro-pyrimidine, 2,4,6-tris-methylsulfonyl-pyrimidine, 2,4,5,6 -: 'etramethylsulfonyl-pyrimidine, 2-t'-ethylsulfonyl-4-methyl -5-nitro-6-chloro-pyrimidine, 2-methylsulphonyl-4,5-dimethyl-6-chloro-pyrimidine, 2-ethylsulphonyl-4-methyl-5,6 = dichloro-pyrimidine, 2-methylsulphonyl-4,6 dichloropyrimidine, 2,4,6-trismethylsulphonyl-5-chloro-pyrimidine, 2-methylsulphonyl-4-carboxy-6-chloro-pyrimidine, 2-methylsulphonyl-4-chloro-pyrimidine-5-sulphonic acid or 4,6 -Bis-methylsulfonyl-pyrimidine and other compounds, some of which are already mentioned on page 11. The reaction of dyes containing amino groups or dye precursors with heterocyclic compounds of the formula (XVI) is carried out, depending on the type of starting compounds used, in an organic, organic-aqueous or aqueous medium at temperatures from -100 ° C. to 80 ° C., preferably in the presence of alkaline condensing agents such as pyridine, aqueous alkali carbonate or alkali hydroxide solutions, when using paraffin intermediate products, the condensation products obtained are converted into the desired end dyes in a conventional manner. This process is of preferred interest for the preparation of azo dyes by, for example, first condensing a diazo and / or coupling component which has a reactive amino group with the active component (XVI) and then condensing the intermediate product obtained by diazotization and / or coupling and / or Condensation converts it into an azo color # 3toff. This subsequently further conversion reactions can be carried out, as are customary in azo dyes, eg. B. acylation, condensation, reduction and metallization reactions. Also in the representation of other dyes, in particular those of the phthalocyanine and anthraquinone series, the condensation of a reactive component (XVI) can initially take place with an intermediate product, e.g. B. with m-phenylenediamine or a m-phenylenediaminesulfonic acid, and the reaction product obtained then with z. B. bromamic acid (1-amino-4-bromo-anthraquinone-2-aulfonic acid) can be further condensed to a reactive anthraquinone dye or with copper or nickel phthalocyanine sulfonic acid halide to form a reactive phthalocyanine dye. A further variant for the preparation of the new dyes of the formula (XI) is that dyes containing amino groups or, in particular, paraffin intermediates which have an exchangeable hydrogen atom on the amino group , with compounds of the general formula A1 (Z) t (XVII) wherein A 'is a Represents a pyrimidine ring, Z is an anionically split off radical, with the exception of a sulfonyl radical, and t stands for the number 2 or a number greater than 2, replacing one of the anionically split off radicals Z, then converts the remaining Z radical (s) in a manner known per se converts into sulfonyl substituents and, when using paraffin precursors, converts them into the desired final dyes: The replacement of one or more anionically removable substituents Z, e.g. B. of halogen atoms against sulfonyl can be, for. This can be accomplished, for example, by reacting the compounds with alkyl or aryl sulfinates or, if X represents, for example, an anionically cleavable alkyl mercapto or aryl mercapto group, converting these into the corresponding sulfonyl radicals with the help of suitable oxidizing agents, such as hydrogen peroxide, hypohalites or permanganates. The dyes (X1) obtainable by the various processes outlined can, as already mentioned for a few cases, be subjected to further reactions customary for dyes, for example by using metallizable dyes with metal donating agents, in particular with chromium, cobalt, copper or Nickel salts, treated, dyes which have reducible groups, in particular nitro groups, reduced, dyes which have acylable groups, in particular acylable amino groups, acylated, or by treating dyes subsequently with sulfonating agents, such as with chlorosulfonic acid, thionyl chloride, oleum or SO3 in chlorinated hydrocarbons to introduce more sulfonic acid groups into the products. The last-mentioned process is sometimes of particular importance in the series of anthraquinone and phthalocyanine dyes. Depending on the number of reactive -HNI? F groups (R, 4 = hydrogen or substituent, such as a lower alkyl radical) in the paraffin residue or in the paraffin precursors, one or more groupings of the general formula -YAK can be incorporated into the dyes . In the majority of cases, the number m 4 is not exceeded, but dyes, especially those with a higher molecular weight structure, with more than 4, z. B. up to 8 groupings of the formula to synthesize. If the dyes (XI) represented according to the method contain metal complexing groups, these can be removed by the action of metal-releasing agents, e.g. B. of copper, nickel, chromium or cobalt salts are converted into their metal complex compounds. Likewise, they can be subjected to other conventional conversion reactions such as diazotization, coupling, acylation and condensation reactions. For the reaction of dyes containing amino groups with reactive components A; - Y of the formula (XVI), for example, and in many cases preferred, aminoazo dyes of the formula are used in which B, D, Ri and m 'have the meanings already given, or aminoanthraquinone dyes of the formula in which h, R1 and p have the meanings given, or phthalocyanine dyes containing amino groups of the formula where Pc, Z, R ,, q, r and m "are those already given Have meaning a. The condensate products obtained correspond to the general formulas I + XII for the new dyes. 'You can be subjected to further conversion reactions, in particular special successor = end of silencing in the first row of the anthracite quinone and phthalocyanine dyes often of interest is. Instead of the pre-formed amino @; riip; @enha 'leagues' work- substances of the formulas (VIII), (IX), (X) to be used yourself: ", Scan nan also amino: pre-products containing groups for th e Preparation of such dyes "use them, first condense them with the reactive component Ar -Y and then further process them in a conventional manner to give the i; nd dyes. In the case of azo dyes, the procedure for this is that a diazo component or a coupling component which has a reactive amino group is condensed with the reactive component of the formula (XVI) and the desired azo dye is then built up by coupling and modified to a disazo or polyazo dye convert the first protected amino group into the free amino group, for example by saponification, and condense the compound obtained with, for example, 1-amino-4-bromoanthraquinone-2-sulfonic acid to form a valuable anthraquinone dye type. For the preparation of phthalocyanine dyes, similarly to what has been stated for anthraquinone dyes, first a diaminoaryl compound monocondensed with the reactive component Ar-Y can be produced and this then condensed with, for example, copper or nickel phthalocyanine sulfonic acid halides, with @ simultaneously or subsequently other amino compounds such as ammonia, aliphatic amino compounds and / or aromatic amino compounds can also be used. In this way, phthalocyaninesulfonamide dyes are obtained which contain a certain proportion of sulfonarylamide groups which carry the reactive groups and, in addition, a certain proportion of non-reactive sulfonamide groups and / or free sulfonic acid groups. A particularly valuable type of reactive dyes in the context of the new dyes of the formula I corresponds the formula g1 Z (XVIII) -Sa2R _ m In this formula, F is the radical of an organic dye, X1 is an amino group, Z is a halogen atom, Y is hydrogen or an optionally substituted alkyl substituent, R is an aliphatic, carbocyclic or heterocyclic substituent and m is a number from 0.5 to B. In the dyes the According to general formula XVIII, the pyrimidine radical is linked to the parbo radical F via an amino group. The amino group can carry further substituents, such as lower alkyl (preferably 0 1 to 0 5), aralkyl, cycloalkyl or aryl groups, but is preferably in the non-substituted -NH- form. The amino group in turn is directly attached to an aromatic ring carbon atom attached to the dye or to an alkylene group. All reactive Sulfonylaub®tituenten -SO 2R. in 2-position the Lower alkylsulfonyl radicals are preferred with pyrimidine riages 1 to 5 carbon atoms, such as methylaulfonyl, ethylaulfonyl or propyl aulfonTlrente, Aryleulfor y lreste ,. such as phenylaulfonyl, p-toluene aulfonyl-, p-chlorophenylaulfonyl create; Aralkyleultonylreete, like Benzylsulfonyl and p-Toluylmethyleulfonylreste, and also hetero- .aulfonylreate, such as 2-benzothiazolaulfonyl, in question. The reactive Sulphonylaubatituenten can by ionogenic or be further substituted non-ionic groups, e.g. B. by Carbozy, nitro, halogen (C1, Br), sulfonic acid or sulfone residues. As halogen atoms Z-, chlorine and bromine have preferred interease, als.Substituenten Y in addition to hydrogen preferably lower alkyl radicals, such as methyl, ethyl, and substituted lower alkyl radicals, such as halomethyl, z. B. monochloromethyl, bromomethyl, dichloromethyl and trichloromethyl, caboxymethyl, carboalkoxymethyl, such as carbomethoxymethyl and carboethoxymethyl, and cyanomethyl groups. Suitable pyrimidine components which have a reactive sulfonyl substituent in the 2-position include, for example: -rethylsulfonyl-5-chloro-4-pyrimidinyl, 2-methylaulfonyl-5-bromo-4-pyrimidinyl, 2-methylsulfonyl-5-chloro- 6-methyl-4-pyrimidinyl, 2-methylsulfonyl-5-bromo-6-methyl-4-pyrimidinyl, 2-methylsulfonyl-5-chloro-6-chloromethyl-4-pyrimidinyl, 2-benzenesulfonyl-5-chloro-4- pyrimidinll, 2-benzenesulfonyl-5-chloro-6-methyl-4-pyrimidinyl, 2-bensolsulfonyl-5-bromo-6-methyl-4 # pyrimidinyl, 2-methyleulfonyl-5-chloro-6-oarboxymethyl-4-pyrimidinyl or 2-Carbozymethylsulfonyl-5-chloro-6-methyl-4-pyrimidinyl. And some other compounds already mentioned on page 4. The Parbatoffe of the formula (XVIII) can belong to the most varied of classes a listen to, for example, the range of metal-free or metal-containing mono or Polyaso dyes, metal-free or metal-containing asaporphine dyes, such as copper or nickel phthalocyanine dyes, the Anthraquinone # , oxasine, dioxazine, triphenyl methane, nitro, asome thin, bensanthrone and dibensanthrone dyes as well as the polycyclic see condensation compounds of antraquinone, Benssnthron and Dibensanthrone compounds. In the context of these paraffin classes are among other dyes of the following general additives particularly valuable: 1. Asof @ toffe B- #: V - D (% IZ) A2 R1 where B and D aromtisohe, oarbootolisohe or represent hetero-orolisohe Beate, for example B the remainder of an oarbooyoli-like slide component represents the benzene or naphthalene series, and D the remainder an enoloid or phonolusic coupling component, s. B. a 5-Pyrasolons, @ a Acetesaigsäurearylamide, .an ostnaphthalene or an aminonaphthalene, etc .; Otherwise, B and D can be any in azo dyes Have Ubliohe substituents, including others Aso groups; R1 stands for a substituent or preferably for a hydrogen atom, a 'denotes a whole number, preferably the number 1 or 2; A2 stands for the rest . (In) T- O 8 2 where R, Z and Z have the meaning given for formula (x9III.) to have. Preferred radicals (Ia) are, for example, 2-Hethylsulfonrl- 5-chloro-6-methylpyrimidine (1,3) -r1-4 and 2-methylsulfonrl- 5-monohydric pyrimidine (1-, 3) -r1-4, bsw. the corresponding Bromine compounds. Particularly valuable dyes in this series are those s that are water-soluble, and especially those that contain sulfone have acid and / or carboxylic acid groups. The azo color substances can be both metal-free and metal-containing, whereby among the metal complexes the copper., chromium and Robaltko m plexes have preferred interests. Important azo dyes are, for example, those of Benzene- azo-naphthalene series, the benzene-azo-l-phenyl-5- pyrazolone series, the naphthalene-azo-naphthalene series, the Naphthalln-azo-1-phenylpyrazolone-5 series and the stilbene azo-bensol series, with the aulfonic acid group containing dyes are preferred. I® trap of metal coreplastic azo dyes are the iaetallkosplex-bound ' Groups preferably in the o-positions to the azo group, z. H. in the form of o, o'-dihydroxy-, o-hydroxy-o'-carboxy-, o-carboxy-o'-amino and o-hydroxy-o'-aminoazo-β groupings. 2. Anthraquinone dyes here L denote hydrogen or sub-substituents, among these in particular the sulfonic acid group, p is the number 1, 2 'or 3, R1 is a substituent or preferably hydrogen and A2 a radical before R, Z and Y the meaning given for formula (XYIII) to have. Preferred radicals (Ia) are, for. B. 2-methylsulfonyl- 5-chloro-6-methylpyrimidine (1,3) -y1-4 and 2-methylsulfonyl- 5-monaahlorpyrimidin (1,3) -y1-49 or the corresponding Bromine compounds. In the area of these dyes, too, the water- soluble products because of their excellent suitability for dyeing and printing cellulosic fibers preferred, whereby the sulfonic acid group-substituted dyes are particularly suitable prove. 3 # azaporphin dyes # In this formula, Pc stands for the remainder of a phthalo- cyaniris, e.g. B. a copper or nickel phthaloeyaains or a tetraphenyl copper or nickel phthaloeyanine, L stands for hydrogen or a substituent, where as Substituent the sulphonic acid group is preferred, r for the number 1 or 2, q for the number 0, 1 or 2, R1 for a substituent or, preferably, hydrogen, A2 is a rest wherein R, Z and Y have the meaning given for formula I. habea. Pc can of course have further substituents have, in particular sulfonic acid and sulfonamide groups pen. Preferred radicals (Ia) are, for. H. 2-methylsulfonyl- 5-chloro-6-methylpyrimidine (1,3) -y1-4 and 2-methylsul- fonyl-5-monochloropyrimidine (1,3) -y1-4, or the speaking bromine compounds. Water-soluble phthalocyanine dyes of the formula (XXI), those for application on cellulosic materials are particularly preferred are those in the Radical Pe and optionally also as a substituent Z Carry sulfonic acid groups. . The above compilation of a selection of suitable aso, anthraquinone and azaporphin colorants and also the pyrimidine systems does not represent any restriction of the general formulas , namely neither with regard to the preparative possibilities for the preparation of such. Dyes under dbr general formula (XVIII), nor with regard to the valuable application-technical properties shadow -this products: The dyes (XVIII) can aufweinen otherwise in any conventional dyes substituents as Sulfonaäure-, Carbonaäure- optionally 1f -substituted sulfonamide or carbonanide groups, diaulfimide groups, N-sulfonyl- N-carbonylimide group = v alkglaulfone, arylaulfone, alkylamino, arylamino, arylcylamino, nitro, cyano, halogen, hydrocyan, substituted Hydrozy groups, Alloy, thioether, alkyl, aryl, aralkyl, trifluoroalkyl, acylamino, azo groups and the like. The dyes can also contain other fixable groups, such as mono- or dihalotriazinylamino, mono-, D1-, or trihalopyrimidinylamino, 2,3-dihaloquinoxaline-6-carbonyl or -6-aulfonylamino, 1,4-dihalogen phthalazin-6-carbonyl or -6-sulfonylamino, 2-halo-benzothiazole-5-carbonyl or -5-sulfonylamino, esterified Sulfona3ureozalkylamid and Oxalkyleulfongruppen, Sulfofluoriö-, Halogenalkylamino-, acrylo ylamino, and the like have Halogenacylaminogruppen . The new dyes of the formula (XVIII) are obtained by building them up by processes known per se, in particular by condensation and / or metallization and / or diazotization and coupling. For this purpose , an erimidinylamino group of the formula can be added to dyes or parabaturates containing amino groups wherein Y, Z and R have the meanings already given to have via the nitrogen atom of the amino group attached to a ring carbon atom of an aryl nucleus of the dye or paraffin pre-product is bound, import, and in the case of supply use of Parbetoffvorprodukte these in the desired Convert final dyes. To introduce a group (Ib), Dyes containing amino groups are condensed or Dye precursors, which have a reactive hydrogen atom on the Ami nsticks.toff, with compounds of the general formula in which Q is a radical which can be split off and R, Y and Z have the meanings given above. Among the reactive substituents Q that can be split off as aasionic radicals, C1, Br and sulfonyl substituents are of preferred interest. Further suitable radicals which can be split off by means of aasession are, for example, F -, - SO 3M (M = H or metal cation), quaternary ammonium groups, alkylmereapto, alkes = or aryloxy groups. Suitable pyrimidine derivatives of the formula (XXII) for the reaction are, for example, 2-methylaulfonyl-4,5-dichloropyrimidine , 2-methylsulfonyl-4-chloro-5-bromopyrimidine, 2-motiylaulfor @ yl-4-chloro-5-bromine 6-methylpyrimidine, 2,4-Eie-methyl aulfonyl-5-chloropyrimidine, 2,4-Bie-methylaulfonyl-5-chloro-6-methyl. pyrimidine, 2,4-Hie-.benzenesulfonyl-5-chloro-6-methylpyrimidine-, 2-methylaulfonyl-4,5-dichloro-6-chloromethylpyrimidine, 2-methylaulfonyl-4,5-dichloro-6-carbozymethylpyrimidine, or 2 -Carbo = ymethyl-sulfonyl-4,5-dichloro-6-methylpyrimidine. and some other connections already mentioned on page 11. The reaction of dyes or paraffin precursors containing amino groups with heterocyclic compounds of the formula (XXII) is carried out, depending on the nature of the starting compounds used, in an organic, organic-aqueous or aqueous medium at temperatures from -100 ° C. to 80 ° C., preferably in the presence of alkaline condensing agents , such as pyridine, aqueous alkali carbonate or alkali hydroxide solutions, performed. When using Parbatoff toe products, the obtained condensation products in a conventional manner - converted into the desired final dyes. This method has a preferred interest in the representation of azo dyes, by, for example, a diazo and / or coupling compo- component, which has a reactive amino group, initially with of the reactive component 7 = i: condensed and the intermediate pro- duct then by diazotization and / or coupling and / or Condensation converts it into an azoate substance, in which can further conversion reactions are carried out afterwards, as are customary in azo dyes, e.g. B. acylation, con Densation, reduction and metallization reactions. Also at the representation of other dyes, especially those of the Phthaloeyanin- and Anthraquinone series, can condense a Reactive component X? = to be done first with an intermediate product, z. B. with m-phenylenediamine or a m-phenylenediaminesulfonic acid, and then the reaction product obtained with z. B. Broms: minic acid (1-amino -, - bridal anthraquinone-2-sulfonic acid) to a re active anthraquinone dyes or with copper or nickel phthalate cyaninsulfonsäutehalogenid to a reactive phthalocyanine dye Further condensation of the substance. Another variant for the representation of the new dyes of the Formula eVIII is based on the fact that dyes containing amino groups or: in particular Parbntoffzwi®chenprodukte, which at the amino group have exchangeable hydrogen atom, with compounds the general formula H (XXIII) where Y, Z and Q have the meanings already given and. T is an anionically cleavable radical, with the exception of one Sulfonyl radical, means with replacement of the residues Q which can be split off axially, then send the remainder T in a known manner in a sulfonyl converts substituted-SO @ R and @ when using dye these are converted into the desired final dyes in advance. The exchange of a subatituent T z. B. a halogen atom, against sulfonyl substituents can be, for. B. accomplish by the fact that the compounds with alkyl or Arylsulfinaten converts or, if T, for example, an aasionisch represents cleavable alkyl mercapto or aryl mercapto group, these with the help of suitable oxidizing agents, such as hydrogen peroxide, Hypohalites or permanganates, into the corresponding Bnlfonyl- reste -SQ2R modified. The dyes obtainable by the various processes described can, as already mentioned for some cases. ' be subjected to further reactions customary for dyes, for example by treating metallizable dyes with metal-releasing agents, in particular with chromium, cobalt, copper or nickel salts, reducing dyes that have reducible groups, in particular nitro groups, dyes, which have acylable groups, in particular acylable amino groups, acylated, or by subsequently treating parbatoffees with sulfonating agents, such as with chlororeulfonic acid, thiohyl chloride; Oleum or SO3 in chlorinated hydrocarbons to introduce more sulfonic acid groups into the products. The last-mentioned process is sometimes of particular importance in the series of anthraquinone and phthalocyanine dyes. Depending on the number of com- for the conversion reaction into consideration Menden reactive @ -HI1R2 moieties (R2 - hydrogen or Subetituent as lower alkyl) toffvorprodukten in the dye radical or in the Parb, can be one or more groups of the general formula (Ib) in incorporate the dyes. In the majority of Pällen the number m not exceed 4, but are also dyes, especially those of higher molecular weight structure, with more than 4, z. B. to synthesize 8 groupings of the formula (Ib).

If the dyes represented according to the method contain metal complex-forming groups, they can be removed by the action of metal-releasing agents, e.g. B. @ of copper, nickel, Qhrom or Kobaltealzen be converted into their Metallkomplezverbindungen. Likewise , they can be subjected to other conventional conversion reactions such as diazotization, coupling, acylation and condensation reactions.

The new dyes are extremely valuable products that are suitable for a wide variety of uses. As water-soluble compounds, they are of particular interest for dyeing textile materials containing hydroxyl groups , in particular textile materials made from native and regenerated cellulose, as well as from wool, silk, synthetic polyamide and polyrethane fibers. Thanks to the reactive sulfonyl substituent (s) in the pyrimidine ring , the products are particularly suitable as reactive dyes for dyeing cellulose materials using the techniques that have recently become known for this purpose. The fastness properties obtained, in particular wet fastness properties, are excellent. For the dyeing of cellulose, the dyes are preferably in a aqueous solution used, which reacts with alkaline substances, such as alkali hydroxide or alkali carbonate, or with in alkaline rea- Compounds passing over by substances, such as alkali carbonate, can be moved. Further aids can be added to the solution. which, however, are not undesirable with the dyes Should react wisely. Such additives are, for example, surface-active substances, such as alkyl sulfates or the migration of the Dye prevented substances or dyeing auxiliaries, such as Urea (to improve the solubility and fixation of the Dyes), or indifferent thickeners, such as oil-water Emulsions, tragacanth, starch, alginate or methyl cellulose. The solutions or pastes produced in this way are used towards this coloring material, for example by padding in the poulard (rurse plot) or applied by printing and then some time at elevated temperature, preferably 40 to 150 ° C, 'erhitzi The heating can be used as back in any order auagefühiiz in the hot flue, in the steamer, on heated rolls or by placing it in heated concentrated salt baths when used alone today. Hei use of a dye liquor without padding or alkali is a passage of the dry goods-through is added to an alkaline solution of common salt or Glauber's salt, is connected. The addition of salt reduces the migration of the dye from the fiber. The drawing-dyeing material can also be pretreated with one of the aforementioned acid -inhibiting agents, then treated with the solution or paste of the dye and finally, as indicated, fixed at an elevated temperature. For coloring. long liquor goes into an aqueous solution of the dye (liquor ratio 1: 5 to 1:40) -at room temperature and dyed 40 to 90 minutes, optionally increasing the temperature to 85 ° C, with partial addition of salt, z . B. sodium sulfate, and then alkali, such as sodium phosphates, sodium carbonate, NaOh or KOH. This is where the chemical reaction between the dye and the fiber occurs. After the chemical fixation has taken place , the dyed material is rinsed with hot water and then soaped, removing the rusts of the dyestuff that have not been fixed. Excellent real ones are obtained , especially those which are wet and lightfast. Colorations. In the so-called cold pad-batch method, a Any subsequent heating of the padded fabric can save characterized in that s is the tissue for some time, eg. B. 20 to - 40 hours, at room temperature. rature stores. In this process , a stronger alkali is used than in the above-mentioned dyeing process from a long liquor. For printing on materials containing hydroxyl groups, a printing paste made from parbate solution, a thickening agent such as sodium alginate and a compound which reacts alkaline or which splits off alkali when heated, aria sodium carbonate, sodium phosphate, potassium carbonate, potassium acetate or sodium and potassium carbonate, and that printed material rinsed and sieved, #. Enthaltest -the dyes metal complex-forming groups, the dyeings and prints can often by Nachbehandelag with metal-yielding agents, such as copper salts z. B. copper sulfate, chromium, cobalt and nickel salts, such as chromium acetate, cobalt sulfate or nickel sulfate, can be improved in their fastness properties. Amide group-containing textile materials such as wool, silk, synthetic polyamide and Polyurathaafasern be dyed generally in accordance with the dyeing methods customary for this purpose in acidic to neutral region, where occasionally a final increase in the pH Wertee the Färbebandes, z. B. to pH 5.5 to pH 8.5 is advantageous. The dyes are applied, for example, to synthetic polyamide fabric as solutions or, preferably, in dispersed form and then post-treated , optionally together with (preferably smaller amounts) acid-binding agents such as sodium carbonate. Particularly favorable results are achieved with those dyes which are insoluble or only sparingly soluble in water. These are processed into a dye dispersion using conventional techniques and with the addition of the known auxiliaries and used as such in dyeing and / or padding tape or in a printing paste. The appropriate for this application aid are compounds, among others connects that prevent the dye migration on the fiber, such as cellulose ethers, alkali metal chlorides and -eulfate, wetting agents such as condensation products of ethylene oxide and fatty alcohols or phenols, sulphonated fatty alcohols, Zösungdmittel as thiodi, glycol, also thickening agents such as starch, tragacanth, alginate @ thickening, gum arabic , etc. The aftertreatment of the dyeings, impregnation and prints obtained on polyamide fiber fabrics is preferably carried out at a temperature of 50 to 1100C and for a duration of 5 to 60 minutes. Here, too , the colorations in the event that the dyes used contain metal complexing groups with metal-donating agents, such as copper salts, e.g. B. copper sulfate or chromium, cobalt. and nickel compounds, such as chromium acetate, cobalt sulfate or nickel sulfate, can sometimes be improved in their fastness properties . The ones with the. The dyeings available for new dyes generally have good to very good fastness properties, in particular excellent wet fastness properties . In the following examples, parts stand for parts by weight, unless otherwise stated. EXAMPLE 1 To a solution of 34.7 parts of sodium 2-aminonaphthalene-4,8-disulphonic acid and 7 parts of sodium nitrite in 300 parts of water, 28 parts by volume of concentrated hydrochloric acid are added while cooling with ice, and the mixture is stirred at 0-100 ° C. for 1/2 hour. After excess nitrous acid has been removed, 10.7 parts of 3-aminotoluene, dissolved in 10 parts by volume of concentrated hydrochloric acid and 150 parts of water, are added and the coupling is completed by blunting the mixture to PR 3-5. The resulting aminoazo dye is salted out, filtered off with suction, washed and then redissolved in 700 parts of water with the addition of sodium hydroxide solution at pH 7. The aqueous solution is then mixed with 21 parts of 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine and stirred vigorously. The temperature of the reaction mixture is kept at about 650C by heating; it blunts the released is the hydrochloric acid from sodium carbonate solution, until the reaction is completed. The resulting dye of the likely formula is salted out with 80 parts of sodium chloride, pressed off, washed and dried at approx. 50 ° C. in a vacuum. It is a yellow powder that is soluble in water with a yellow color. . When printing cellulosic fabric for a printing paste that in kilograms. 3.5 grams of the dye, 100 g Barnstott, 300 n1 Water, 540 g alginate thickener (60 g sodium alginate per kg thickening), containing 2 g of sodium hydroxide and 10 g of soda and those with Water made up to 1 kg, dry for 8 minutes 105 ° C, rinse with hot water and soapy at the boil, so that if you keep a strong, rotstish yellow print of good washing and lightfastness. example 0.1 Get the copper mark: connection of the formula Na @t 5 @ I, d @ 00 NM = Nmbf ®, @ - 0 S03Na (ierpetellt..maetvd «lmgahen the German patent step 1117235) daseh = Uppsla vsac diasetierte 1-lmiae-8 (bease @ ss @ tehr @ osF) - sarhtha @ is @ # üsi @ temsäiss ## (3,6) in solo alkaline medium with the ätwgvaleatem amount of 2- # cetylsnino-S-hydrozynaphthalindisultom- säsre- (t, 8), ümvandluag the M®neasoverbinduag in the Kapterkemplez by esydative copper and hydrolysis of the # cet'1- and the Bemsol- siltemylgrappe) be 2500 Volunteilen water of 60 - 6.5 dissolved and mixed at this temperature with 0.12 M01 2,4-bis-methylsulfonyl-6-methyl-pyrimidin - 650C at PH. 6 During the condensation , sodium carbonate solution is added a PR of 1 # - 19, j complied with. After the reaction has ended, the Sawn out and insulated until stiff. The dye represents dried A duaUes powder that dissolves in water with a blue color. 100 parts by weight of a full Bawrvebes has been used for space , temperature with a savory solution containing 2% of the dye, Contains 15 C / 1 sodium hydroxide carbemate and 150 g / 1 urea, fouladed, dried on avi, heated to 140 ° C for 10 minutes, do rinsed and soaped at the boil. The fabric becomes very clear dyed true to size in blue tones. -Example 3 46 parts of the analogous to the information in Example 1 by coupling from dia: etated 2-dminenaphthaiin-4,8-disulfonic acid to 3-methyl- amine-toluene obtained Nenea: of dye are in 400 parts Water from 60 - EboC at pB 7 - S dissolved and in the presence of excess safe sodium acetate or caloius carbonate proportion with ina- total of 2, parts of Z, [-gis-methylsulfonyl-6-methyl-pyrimidine added and Stirred at this temperature until a sample at the -Anaiiuaxa no longer shows a color change. The resulting dye the probable formula ph y @ t 0 t CIh N = N @ N iH3 CHI @osNa , is auageaalsen, vacuumed, washed and dried. You impregnate cotton fabric with a solution of 20 - 250 C, the per liter liquor 20 g of the above dye and 0.5 g of one non-ionic Netsmittela (see a polyo: ethylated oleyl alkehola) as well as 150 g urea and 15 g sodium biearbenate. The tissue is then placed between two gumaiaalsem on one Moisture content of approx. $ 100 squeezed off. After the interim drying at -50 - 600C is heated to 140 ° C for 10 minutes and the se obtained staining rinsed thoroughly with hot water and 20 minutes treated at the boil with a solution containing 5 g of Naraeiller per liter Contains soap and 2 g of soda after rinsing and drying a strong, red-tinged yellow color of good Na9-, rubbing- and lightfastness. The following table shows the diasoconents, Coupling components and those which can be xerknüpfbaren with the amino group Reactive components listed, from which analogously to the information in the Example 1 - 3 dyes can be built up, the color of which tones - obtained after the application process described - Likewise. are listed in the table . Abbreviations for 1 m 2-kethylsulfonyl- ¢ -chlor-6-methyl- the reactive components: pyrimidine B - 2g [-Bis-methylsulfonyl-6-methyl- pyrimidine Example slide component, coupling component, reactive color No component 2-aminonaphthalene-4,8-1-amino-2-nethozy-5-A . yellow disulfonic acid methylbene sol MB p 6 1-lminonaphthalene-3-, 6- disulfonic acid 1-amino-3-methylbenzol A " 7 wx B- 8 2-aminonaphthalene-5,7- disulionic 1-A = ino-3-ethylbene sol A 9 B 10 2-aminesaphthalene-6,8- disulionic acid 1-amino-3-methylbene sol A 11 " " B " 12 4-aminoasobensol-3,4'- disulfonic acid 1-amino-3-methylbenzol A brown-yellow Example Diasokoaponente coupling component reactive color No. - kompeaeate 13 1-aainobenzene-4-sulfone acid - ° -> 1minonaphthalene- 6-sulfonic acid 1-amino-3-methylbenzol B brown-yellow 14 2- (3'-sulfo-4'-asrinophenyl) - 6-methyl-bensthiasol-'7-sul- fonsäure "1 _ yellow 15 2-aminonaphthalene-4,8-di- 1-methylaaino-3- sulfonic acid ethozybensol B `" 16 "1-aaino-3-acetylaaino- bensel A " 17 "Aniline A" Example 18 In the solution of 36.5 parts of the sodium salt of the 1 amino 8- hydroxymaphthalia-3,6-disulfonic acid in 100 parts of water with good Mhrem- bei5® -6 (10 25 parts of 2,4-bis-methyl sulfoayl-6-meth'1- pyrisidine protruding and constantly blunting the free dewdeazalic acid to pH 6 - 7 for as long! stirred until none free leino; raps ssha is detectable. This is obtained as a par- Stoffsvisctrenprodnkt is after dilution with 600 parts of water and Addition of 12 parts of soda at 5-10 ° C. with 17.5 parts of diasetated 2-Aainobensolsulionäure, dissolved in 200 parts of water, coupled. The dye of the formula which is formed at an Ead pH of approx. 7 . «= Ottw ' SOaNw H0 N N = N Ne @. ' @yNs __._ vi = Imät 100 parts of sodium chloride are salsed out, filtered off with suction, washed and dried at 30 - 40 ° C in vacuum. The dye forms metallic shiny red needles that can easily be put into water red paint. Is made from cotton or regenerated collulose one of the methods described in Examples 1-3 colored or printed with this dye, you get clear blue- pungent red coloration and pressure * of good Nafl-, rubbing and light- authenticity@ The following procedure gives equally good results: 50 Gr @ Haoavollstrang work in 1 liter of a dye liquor, containing 1.5 g of the above dye, colored by the Temperature increases from 200C to approx. 800C within 30 minutes, add a total of 50 g high salt in several portions, then add 20 g of soda and 60 minutes at this temperature treated. After rinsing, soapsing at the boiling point and drying w a bluish red color with good wet, rub and light authenticity. The following table shows the shades of other colors substances are listed, which are derived from the also listed Diasokompo- nenten, coupling components and with the amino group in the the latter linkable reactive components analogous to the information in Example 18 - or also by conversion of the corresponding Aminoaso- dyes with the active components - built up verden and after one of the processes described above on cellulose materials colored or printed: Abbreviations for the reactive components as in the table for example 3 For diazo component, coupling component, reactive color game component No. 19 1-aminobenzene-2- 1-amino-8-hydrozy- B red sulionic acid _ naphthalene-3,6- disulionic acid 20 aminobenzene 1- (3'-aminobensoyl- A " aaino) -8-hydroxy- naphthalene-3,6-disulfone- acid 21 "" B " 22 1-amino-2-carbocyte-1-amino-8-hydrozynaph- A " bensol-4-sulfonic acid, thalin-3,6-diaulfona acid 23 1-amino-4-methylben- sol-2-sulfonic acid "A 24 1-amino-3-acetylanino benzene-6-sulfonic acid "B. 25 1-Amino-3- (2'- Z4- 't- "A» aulfophenylamine >-4'- chlortriaain-1 ', 3', 5'-yl- 6 ') - aminobenzene-6-aulfone- acid 26 1-aminobensol-2-sulfone- 2-amino-5-hydrocyan- A orange acid naphthalene-7-aulfen- acid With- Diasukesfeaente coupling component reactive color game co-component No ,. 26a 1-A = ino-3- (2'- 2-aaino-5-hydrozy- A orange f- "-suliophenyl- naphthalene-7-aulion- astinoJ-4 # -nethyl acid aain®-triasin-1 ', 3 ', 5'-yl-6 # ) -aaino- bensol-6-sulion- - acid 27 1-hinobensol-2-methyl-ino-5-hy-A . orange, 2-sulionic acid drozy-naphthslin-7- sulionic acid 2R 1-Amino-! 1-acetyl- "A Sharlaeh assino-6-sulioic acid 29 "2-Astino-5-hydrozy- A » naphthalene-7-sul- Tonic acid Example 30 In the solution of 21 parts of the Nstriumalses the 1,3- Diaminobenzzl-6-sulfonsänre in 100 parts of water are under good Stir 2.5.0 parts! -Yethylsulfonyl-4-chloro-5-methyl # pyrimidine and stored at 60-650C under constant digem blunting the ireirerdenden hydrochloric acid to pH - ® as long agitated, there is a sample when diazotizing and coupling on 1-hydrocyclic naphthalene-4-sulfonic acid a clear, yellowish red color gives. The resulting Parbetoffsvischenprodukt is after addition of ice poured directly with 7 parts of sodium nitrite and 28 parts- trated hydrochloric acid and then decayed with one.: ` th solution of 47 parts of the sodium salt of 1-BensoylamimrB- # hydrocyanaphthalene-3,6-disulfonic acid and 12 parts of soda iai 2 »parts Water combined, coupling to the dye of Formeb NO Nu_oc - NaN GRASS @@ H n r @ wo @ soaw @ takes place, the carrion salted, sucked off, washed and at 30 = 400C 'is dried in a vacuum. The dye dissolves in water light with red color and delivers after one of the obembesee- surrounded procedures klare.blanstichig red coloring and printing * together Cellulosic materials. In the table below are the color tones and the pH value of the coupling medium of dyes listed analogously to the Information in Example 30 from a Dinzo component, which is a contains further, preferably acylatable amino group, from one Coupling component and from one with the diazo component KnÜpfbasen reactive component are produced. For dyeing ben and printing of cellulose materials with the dyes of The above-mentioned procedures can be used in the table. Abbreviations for the reactive components as in the table for game 3 With- diazo component coupling component reactive- pH of the color- play compo- coupling Nente lunas- mediums 31. 1,3-diaminoben-2-aminonaphthalene-A 4-5 orange zol-4-sulfonic acid 5,7-disulfonic acid 32 "2-aminonaphthalene- A 4-5" 3,6-disulfonic acid 33 ". 2-aminonaphthalene- B 4-5" 6-sulfonic acid 3b "2-N-methylamino-8- A 4-5" hydrocynaphthalene 6-sulfonic acid Bapl. Diazo component Coupling component Beaktir- pH of the color No. Component coupling nediums 35 1,3-dianinobenzene-1- (3 ', 5'-dichloro-1', L 7-8 red 4-sulfonic acid 21-thiazole-4'-carbon amido) -8-hydroxynaphtha- lin-3,6-disulionic acid 36 "1- (2 ', 4'-dihydroxy- B 7-8" triazin-1 ', 3', 5 ', - yl- 6'-amino) -8-hydroxynaphtha-- lin-3,6-dieulfona acid 37 "1- (3 ' , 51 -Dichlor-1', A 7-8" 2'-thiazole-4'-carbon anido) -8-hydroxynaphtha- lin-3,6-disulfonic acid 38 "2-hydroxynaphthalene-3,6-A 8 scarlet di®ulfonic acid 39 1-acetylamino-8-hydroxy-B 7-8 red naphthalene-3,6-disulfone- acid 40 "1- (3'-sulfophenyl) -3-nethyl- pyrazolon-5 A 6 gel; 41 "1- (2 ', 5'-dichloro-4'- A 6 yellow sultophenyl) -3-methyl- pyrazolone-5 42 "1- (5 ', 7'-disulfonaphthyl-2'-) -3-methyl-pyrazolone-5 A 6 yellow 43 "1- (3'-sulfophenyl) -3- B 6" methyl-5-aminopyrazole 44 1,4-dianinobenzene- 2-amino-8-hydroxynaphthalene- 3-sulionic acid 6-sulphonic acid A 4-4.5 red E.g. Slide component coupling component reactive- pli of the hue ' No: component clutch. mediums 45 _ 1,4-Diasinobensol-12-Acetylamino-5-hydrozy- A 6-7 scarlet 3-sulfonic acid inaphthalene-7-sulfionic acid 46- "1-acetylamino-5-hydrozy- B 6-7 red naphthalene-7-sulfonic acid Example 47 51.6 parts of the diasotization of 1-Iiydrozy-2-smino-bensol-4 sulfonic acid and coupling on 2-amino-5-hydrozynaphthalene-7-sulfonic acid in water / P, ridin in the presence of soda and subsequent treatment dyes of the formula obtained with a copper-donating agent o-cu-- o Ni @ ®35 @ NH: so3N @ 1500 parts of water are dissolved at pH 7. While stirring well one carries at E0 -650C 25.0 parts of 2 -% U ethylsulfony1-4-chloro-6-methyl- pyriaidin and blunt the released hydrochloric acid with soda - löauns continuously to a pH of 7-B. If no free amino group is more detectable, the reactive dye formed is of the formula o cLt0 M @ HOt CHF _ NsOsS \ \ NH @ 503Ns GH3 , salted out, pressed @, washed and vacuumed at 30 - 40 ° C dries, fabrics made from cellulose materials can be atoff according to one of the above methods in na9, rubbing and lightfast ruby tones can be dyed or printed. The heavy metal complexes are broadly listed in the following table. rer Aminoazofarbatoffe and linked to the amino group Re- active components, as well as the color tones of these dyes on cellu- laser materials listed. The production of Aminoasotarbatoff e, their metal complexes and their conversion with the Reaktivhompoaentea can be carried out analogously to the information in Example 47. Abbreviations for the reactive components as shown in the table Example 3 ' Example Aminoazofarbatoff Complex Reaktiv- larb- No bound component Heavy metals te 48 1-Hydroxy-2-aminobensol-Cu A. Ruby . 4,6-disulfonic acid r - + 2-amino- ' S-hydroaynaghthalene-Z-sulfonic acid Example Aaiseaso Dye Complex Reactive Color No bound conpon- tone Heavy metal te 49 1-Hydroxy-2-aainobensol- Cu A ruby 4-sulfona acid - -> 2-Ethylaaino- 5-hydrocynaphthalene-7- sulfonic acid 50 1-aaeino-2-hydroxy-6-nitro-Co A ruby naphthalene-4-sulfonic acid - * 2-amino-5-hydroxynaphthalene 7-sulfonic acid 51 "Cr A greenish tint Gray 52 1-atino-2-hydroxy-6-nitronaphtha- lin-4-sulfonic acid - + 1: Mino- Co B reddish 8-hydroxynaphthalene-4-sulfone black acid 53 1 Iaine-2-hydroxy-5-ethylaul-Cu A violet fonyl-bensol ---; 1-amino-8-hydroxy naphthalene-3,6-diaulfonic acid 54 # Co A gray 55 - "Cr A greenish tint " black 56 ' 1-Anino-2-ethylbenzene-4-aul- Cu B Blue fonsäsre - + 1-Anino-2-hydro: y- 5.-s <ethylbene - @ 1-aaino-8- hydroxynaphthalene-4,6-disulfone acid 57 "Co B gray 58 "Cr A green tinted black Kepl. lminoaso dye complex reactive] hue No bound koapo- Sister ernetall component 59 (1-Amino-2-chlorobensol-4-aulfon- Cu A Marine- acid -1 + 1-Hydroiy-2-acetylaminobenzene), blue saponified, -; 1-amino-8-hydroxy naphthalene-3,6-disulfonic acid 60 "Co A gray 61 1-Amino-8-hydroxynaphthalene-4-aul-Co A Black tonic acid + --- 1-hydroxy-2,6-diaainobenzene- -4-sulfonic acid> 1,3-hydroxybene sol 62 1-Amino-8-hydroxynaphthalene-3,6-di o A " sulfonic acid % '- 1-hydroxy-2,6-diami- nobenzene-4-sulfonic acid - 4 * 2-Hydroxy- naphthalene 63 1-Amino-8-hydrozynaphthalene-4- Co A " sulfonic acid # (- 1-hydroxy-2,6-dia- minobenzene-4-sulfonic acid ---> 3-methyl- pyrazolone- (5) Example 64 96 parts (based on 100% Vare) in the usual way due to the action of chlorosulfonic acid and thionyl chloride Nupterphthalocyanine freshly made copper phthalocyanine , @ Qtrasulfochlorids or dec iammo? En, from 1-sulto-bensol-3,4- icarboxylic acid via the en ° 6- ^ " speaking copper phthalocyanine tetra- Cixyonic acid built up Nupfer phthalocyanine tetraauifochloride .-79rden in Porm des -7eiicht, well washed suction cake in 500 `share water and 500 parts ice, the solution is clay 50 '! Rush dos Natriesssalses of 1,3-Diamiaobensol-4-anlioaaänre added in 500! hurry Viennese and the pli with. $ oda to 8.5 set. The suspension is stirred for 24 hours at Rauatespo- ratnr and keeps the pH always uni by continuously adding soda 8.5. The resulting condensation product is at pH 1-2 by Adding Kochaals precipitates, sucks off, washed and then again dissolved neutrally in 1000 parts of water. In the blue% ösnns with intensive stirring 71 parts are added 2,4-His-methylsulfonyl-6-methyl-pyrimidine and under constant blunting with Sodalüsung to pH 7 - 8 is stirred at 60 -650C, until free amino groups can be detected. The reactive dye of the formula thus obtained w @ äo @ t @, NII @ . i8 @ N @ w cm - Phfnlo K yy o nin G93 ) 4.irt is aase.alsen, washed and dried at 38-400C in vacuum. It otells a dark blue one that is soluble in water with a blue particle Powder-der and dyes cotton and resenerate cellulose after one the above mentioned dyeing or printing processes in clear blue tint v »x good NaE, rubbing and light fastness. Instead of the 96 parts of tupterphthalocyanine tetraanlfochleride kän « - with the same working time as in example 64 - awake 87 parts (based on 100 Xigo goods ) that Eiawirh likes , obtained from chlorosulfonic acid on copper or nickolphthalocystine lichen Kapier- or Nickolphthalodrasin-trisslfochlorids in Fern the moist, well-washed suction cake with ice water is used been; you then get clear blue coloring above, Roaktiv color fabric. Even when you work as indicated in example 64, however starts from 87 parts of copper phthalocyanine trislphochloride and * great of the 30 parts the Natriunsalsos the 1,3-Diaminobonsol-4- oulfonic acid 90 parts of the sodium salso of 4,4 # -Dianime-dipkomyl- 2,21-disulfonic acid or 90 parts of the sodium salso of 4,4 # dianino stiboa-2, p, @ - diss @ fsssäsre sets in, receives some itoactive dyeo, wolobe Collulooonaterialion according to * in the above mentioned - colors in nag-rub and light sahtaa, clear blue tones to dye. goes 0 "from 41 #, 4®ra @ O8 #, 4""- Totrap @ oslrI-Cm-phthsloeyasin ass, it receives erah gslfsehleriormsg loaded U «ats with i, 3-fhearäam- diemia-4-oulfoasiiore snd aeylissnsg with 2,4-bis-mothylsulfonyl-6- “Thyldp, vrimigin . of a 1 active dye, the Collmlesoaateri- old in Uegeawart silnrebiadender means in clear, na / - and borrowed- sabtea wlswltMen colors. . Daissial @ r. @ One loosens 71 ropes dos through, Usesats of 1-Amine-4-brs e- satiraaäfnan-2-sa@i.naänre with excess 4, t # -diamino- diphenyl-2, ß'-disniionic acid obtained aminoanthraquinone dye in? 0ss? rush water, bbi 60 -65 ° C with good stirring 25 Part 2-Methylsulfony1-4-chloro-6-methyl-pyrimidine and hold by continuously adding ton soda solution a p li of 7-7.5- upright. If there is no longer any amnesia group, the one that has arisen Dye of the formula 0 N @ N @: Ot Cl! O NN @ CN glaze, vacuum , wash and vacuum dry at 50 - 40oC. net. It dyes cotton and regenerated cellulose according to one of the above listed procedures in wet, rubbing and lightfast blue tones. If you proceed as indicated in example 63, but represent the 71 parts of the starting dye used there equi- valent, * Keesen- one of the following derivatives of the 1-ßmino-b- (»Inoarylatsinol-anthrachinoa-'2-sulionic acid uses, receives; similar dyes whose blue colorations are similar; `_ @ ` ride like those of the above, have farba-ofis: re, ine-b- @ b @ - @ inophenylamino @ - @ thrachi @@ _ @ - @ fl @: @ - dr @@ i8onz @@ r @: ä Isomfrense @ rtiscaus i-llmino-t- 4'-aminophenylano @ -ranthra @@ d @ to @ - 2,5- and..2,8-disulfonic acid, isomer mixture of 1-amino-444'- amino-2'-sulfophonyl »ino) -anthraquinone..2,5- and. 2,8-disulföa- acid, isomer mixture of 1-amino-4- (3'-aminophenylamino) -anthraquinone-2,5- and. -2,8-disulfonic acid, 1-amino-4- (3'-aminophenylamino) -anthraquinone-2,6-disulfonic acid, 1-amino = 4- (3'-amino-4'-sulfophenylamino) -anthraquinone-2- sulfonic acid. With 1-amino-4; (4 '- @ " -amino-2 " -aulfophenyaaao-phenyl) -anthsachinon-2,6-disulfonic acid gives a bluish gray reactive dye e. Example 66 By proceeding as indicated in Example 47, is but instead of the used there copper-containing Amigomonoanofarbstoff of the equivalent amount of the chromium complex of the diazoterter by coupling 1-amino-2-hydroxy-3-chlorobenzene-5-sulfonsäurs 1 -, r3 '- (3 " -Aminophenyl27-aulfonylimido-sulfonyl-phenyl 3-meth'1-pyrazolone- (5) obtained aminoazo dye, so mam receives a reactive dye, which cellulose materials by one of the above methods in good wet, rub and stained Önen-fading tan T.

Example 67 ! D, 1 mole of the copper complex compound of the formula are in 3000 parts by volume -Water dissolved at pH -6 and stirring. at a temperature of about 600C combined with 27 parts by weight (0.1 mol) of 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine . That Mixture is stirred until the condensation has ended, the F, A- substance separated by adding a little sodium chloride and in *! .est The residue is waxed with acetone and at Aaiustenpiratur dried under reduced pressure. A dark powder is obtained which dissolves in water with green color and cotton after the Verahrenaweiaea indicated in Examples 1 - 3 in green Tones colors. You impregnate building roll fabric with a solution: from 20 - 25o C, the per liter liquor 25 g of the above dye and 0.5 g of one, non-ionic wetting agent (e.g. a polyethylated oil alcohol), 150 g urea and 20 g sodium carbonate. At'- the fabric is then placed between two Guani rollers on one Moisture content of about 100 X squeezed off. After the interim drying at 50 - 60 ° C is heated to 14000 for 10 minutes and the the dye obtained in this way is rinsed thoroughly with hot water and 20 Minutes of boiling treated with a solution that per liter so-called Contains Marsedler soap and 2 g of soda. After rinsing and drying - receives a green color of good Ns8, friction and Lightfastness. - Even after one of the others, in Examples 1 to 3, 18 and 30 used lPtlwbe or printing processes are available on Cellulose materials are clear from good containers. Example 68 0.1 get the fast of the amino azo link of the formula by coupling the diasoniua compound from ö-Acetaaino-2-amino- naphthalene-4,8-disulionic acid with 2-Oz "aphthalia-3,6-diaulphonic acid `Verseiturig and- and converting the received Monoasoverbindnag in the copper complex are dissolved in 2000 parts by volume of water at pH 6.5 and with 25 parts by weight of 2,4-bia-metlsulfone, F1.®6-methyl- pyraaidin united. Dr, s reaction mixture is Stirred 65 ° C until the condensation has ended, the pH of the Reaction solution is kept at 7-7'5 by adding Seda. When the reaction has ended, the dye is collected and isolated and dried in vacuum, .The dried dye is a dmcles powder that is Dissolves in water with purple color and Barolle in the presence. from Alkali stains bluish violet? Ömem. Example 69 The aqueous solution of 0.1'Nol of the plucking complex .Formula manufactured according to the specifications of the German patent step i 061 460 bzwo 1 ß85: 9 $ 89 is reacted in the usual way with 22 parts by weight of 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine. By addition of sodium hydroxide maintaining the pH at 7 to 7.5 send isolates the dye after the end of the reaction by salting it out, In the dry state it presents a dark powder which is Dissolves in water with a purple color. Cotton fabric is made in light and dyed wet-fast purple tones. -Leg goal ? 0 2795 parts of 2-methylamino-5-hydroxy-naphthalene-7-sulfone acidic sodium are dissolved in 150 parts of water, with 25 parts @ .a 2,4-His-methylsulf'onyl-6-methyl-pyrimidine added and at 50 - 55oC. With constant blunting of the methanesulfinic acid formed with a total of 34 parts by volume of 16% soda solution at .pH 6 - 7 touched. After a short time, the acylation is complete, the pH is 6 and no longer changes. lgan then adds 30 parts of sodium bicarbonate and leaves at 20 ° C within 1 minutes the slide suspension from 34 fsile di- sodium salt of 2-aminonaphthalene-1,7-disulfonic acid in 200 parts Drop water. The immediately resulting orange reactive color Substance of the formula after stirring for one hour by adding 80 parts of cooking salt completely separated, filtered off, with diluted common salt Washed solution and dried at 35 ° C. in vacuo. He colors Cellulose materials according to the above-mentioned processes in red pungent shades of orange with very good wet fastness properties and good chlorine resistance. If you use in this example instead of 25 weight share 2,4-bis-methylsulfonyl-6-methyl-pyrimidine equivalent men gene of 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine, so obtained an orange reactive dye, its dyeing Behavior of the reaction product of the bis-methylsulfonyl derivative is equivalent to. In an analogous manner, acylation of the column 3 Aminonaphtholsulßonsäuren listed in the table below with 2,4-bis-methylsulfonyl-6-methyl-pyrimidine and coupling of the acylamino-naphtholsulfonic acids formed with the in column 2 Se- called slide components orange to red beactive dyes. Bei- Diaso & omponente Aainonaphthol.sulfonsäure hue on play cotton No. 71 2-Auinonaphthalin- 2-Ethylamino-5-hydroxy- urangf 1,7-diaulionic acid naphthalene-7-sulfonic acid - 72 2- (B-hydroxyethylamino) - - 5-hydrozynaphthalene-7- . sulfonic acid .73 "2-Amino-5-hydroxynaphtha- lin-7-sulfonic acid 'j4 "2-Amino-5-hydroxynaphtha-" 1in-1,7-diaulfonaic acid 75 "2-amino- $ - hydrocynaphtha- scarlet fever lin-6-sulfonic acid 76 "2-amino-8-hydroxynaphtha- lin-3,6-disulfonic acid 77 2-axinonaphthalene-2-methylamino-5-hydroxy-orange 1,5-disullona acid naphthalene-7-sulfonic acid 78 ° 2-ethyleaino-5-hydroxp- naphthalene-7-sulfonic acid 79 "2- (B-Hydroxgäthyiamino -) - 5-hydroxynaphthalene-7- sulfonic acid 8Q a . 2-amino-5-hydroxynaphtha- w lin-7-sulfonic acid 8.1 2-Amin®-5-hydroxynaphiha- lin-1,7-dioulfonic acid 82 2-aminonaphthalene-2-amino-8-hydroxynaphtha-8cherlach 1,5-aiaulphonic acid lin-6-aulphonic acid 83 ° ' 2-Amino-8-hydroxynaphtha- " lin-3,6-disulfonic acid 84 2-Amimonaphthalene-12-Amino-5-hydroxynaphtha-Orange . 1,5,7-trisulfonic acid @ lin-7-aulfonic acid 85 "2-methylemino-5-hydroxy" naphthalene-7-sulfonic acid 86 "2-amino-8-hydroxynaphtha-scarlet fever lin-6-sulfonic acid 87 2-aminobensol-2-diethylamino-5-hydroxy-. orange sulfonic acid naphthalene-7-sulfonic acid 88 "2- (D-l-hydroxyethylamino) -" 5-hydroxynaphthalene-7- . sulfonic acid 89 "2-amino-8-hydroxynaphtha-scarlet fever 1 in-6sulfonic acid 90 - 2-amino-8-hydroxynaphtha- @ ' " I.in-3,6-disulfonic acid 91 "2-amino-5-hydroxynaphths orange l in-1, 7-disulfonic acid 92. 2-aminonaphthalene-1-asino-B-hydroxynaphtha- bluish tinge 1-sulfonic acid @lii: -3,6-disulfonic acid red 93 p 1-amino-8-hydroxynaphtha p .lin-4,6-disulfonic acid 94 '2-Aminonmphthalin-1-Amino-8-hydroxynaphtha- °° 1,5-daulfonic acid lin-3,6-disulfonic acid . 95 1-amino-e-hydroxynaphtha- lin - 4,6-diaulionic acid 96 2-Aninonaphthalin- 1-0aino-8-Hydroaynaphtha- bluish tinge 1,5-dioulionic acid lin-6-aullona acid bot " 97 2-Arinonaphthalin- 1-Ariao-8-hydrozynaphtha- 1,? - disalphonic acid lin-3,6-disulfonic acid c 1-aemino-8-hydrozynaphtha p lin-4,6-disionic acid 99 "1-Auino-B-hydrozynaphtha- lin-b-sulfonic acid 100 2-aminonaphthalene-11-amino-8-hydr®zynaphtha- ° 1,5,7-trisulfonic acid lin-6-sulionic acid 101 . 1-Aniao-4-chlorbene 1 Aaino-8-hydrozynaphtha- " sol-2-sulfonic acid lin-3,, b-disulfonic acid 102 1-Aniao-2-nethozy- -Amino-8-hydrozynaphtha- " bensol®5-sulfona acid lin-3,6-disulfonic acid: 103 1- Amine -bensol-2- 1-Asiao-8-hydrozynaphtha- " carboxylic acid-4-sullin-3, G-disul®nsäure fon.acid - 104 1-lnino-4-acetyl-. violet a'inobensel-2-saiioa acid 105 ° ' 1 Aaino-8-hydrosynaphtha- bluish tinge lin-4,5-disonic acid red Example 106 56.5 parts of the 1-amino-3- by coupling of dia: doped acetylaminobenzene-δ-sulfonic acid on 2-aminonaphthataline-5,7-disulfone acid in acetic acid medium and subsequent alkaline or acid hydrolysis of the acetylamino group obtained diaminoazofe, rb- Substance are dissolved in .PH 7 in 450 parts of water. Awake encore of 25.0 parts of 2,4-bis-methylsulfonyl-6-methyl-pyrimidine becomes with constant dulling of the released sulfinic acid with Brine solution to pH 7-7.5 stirred for about one hour at 60 ° C. After loading when the acylation has ended, the reactive dye formed is of the formula salted out, inherited by filtration, again in 4000 parts of water at 300C dissolved, filtered and de 'filtrate by adding 400 parts High salt deposited in a completely pure form. The dye will like Usually vacuum-dried at 35 ° C. It colors cellulose materials after one of the above-mentioned processes in real yellowish tones Shades of orange. Example 107 For a neutral solution of 60 parts of the trisodium salt of by coupling of diazotiester 2-aminonaphthalene-3,6,8-tr- sulfonic acid with 3-acetylaaino-aniline in an acetic acid medium Halteu asinoazo dye in 500 parts of water is added 22 Split 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine and stir one Hour at 650C, with constant addition of sodium hydroxide solution a pH of 7-7.5 is maintained. The partially The acylation product that has fallen is removed at pH 7 by adding 100 Parts of table salt separated completely and filtered off. For cleaning the reactive dye obtained in this way can subsequently be used in 2500 parts Water at 300C dissolved, clarified and treated with the casting salts of the The filtrate is separated off again with 350 parts of table salt. Of the Dye has the formula and after filtering off , drying at 35UC and Bahlea stops yellow powder that easily dissolves in water with a yellow color and cellulose fiber by any of the above dyeing methods in the presence of acid-binding agents in-very real reddish yellow Tones colors. Real yellow also appear on wool and polyamide fibers Stains received. One arrives at similar V2botoffen, -if L-am as above- drives, but instead of the 60 'feile ° @ ain® @ .'- acetlamiaeo-phenylm 1 ') - corresponding to azo-nphheln @@ 3, n, @ triaulfonic acid sodium Quantities of the Asänoserbindungen indicated in column 2 ignite those indicated in column 3 in usual! quietly by diazotization and coupling in acetic acid medium Aminoazo dyes used and with 2-methylsulfony1-4.-chloro-6- methyl-pyrimidine acylated. In the case of diazo component, coupling component, color shade game Gauawo 11e _ No: 108 2-aainonaphthalene- .1-amino-3-methy1-6-srth®zy- strong red- 1,5-disulfona acid benzene stichiges yellow 109 1-Ammino-3-mmethYlbemmsol Yellow 110 " 1-Ami-nonaphthalim-6-retstichigeu sulphonic acid yellow 111 " 1-Ataino-3-acetYlacino- °" benzene 112 "- @ 3-aninephenylurea " 113 "1-amino-3-hydroxyacetyl amminobenzene 114 - 2-Amminonaphthalin- 1-Aaino-3 = ethyl-6-aethosf- strongly rotsti- 5,7-disulfonic acid benzene-like yellow 115 `@ 1-Aminonsphthalin-7-aaifen- 'retstichiges _ acid yellow 5.16 1 # Asino-3sacetyiaincbea: ol 117 w _. 3.A "nopbeuylhgreenstoff 318 ° 'i- & mina-3.hydroayacetyl- 119 1-Amiaonaphthalin- 1 ysiao-3- = ethyl-6-aeth- strongly rotsti- 3,7-disulfonic acid ozybenzol chiges yellow 11 120 " 1- amines -3-sethylbenzene red-stained yellow 121 1-Amiaonaphthalin- 1-Aminoaaphthalin-6-snlfon- reddish-tinged - 3,7-disalfzasäare acid yellow 122 2-asinonaphthalene-1-amino-3-methylbenzol " 3, b-diaalionic acid: 123, @ 1 amino-3-methyl-6aethozy- strong red- benaol stichiges yellow 124 "1-Asaino-3-acetylanino-rotetichige® bensol yellow 125 @ ° 3-amnophenyl urea 126 @ # 1-asino-3-hydrocyacetyl- amiaobeszol 127 . '1: Iainonaphthslia-6-®ulton- acid e 128 2_Aa'onaphihalin- 1-Amino-3-acetylas, inobensol " 6-, 8-disalt®sisäuro 129 "1- amines -2-methozyaapbthalin-- strongly rotten- 6-suläona acid-like yellow 130 @ ° 1-Asiaonaphthalin-6-sul- redstichiges acid yellow 131 2-minonapbthalene-1-aminonapfithalin-6-aulfon yellow k, 0-diaulfonic acid 132 - °° 1-aminonaphthalene-7-sulfonic acid " 133 2-aminonaphthalene- 1-amino-2-'ethoaynaphthalene- strongly roteti- 4,8-disulfonic acid 6-aulionic acid yellow 134 "1-methylamino-3-methylbenzene yellow 135 2-aminonaphthalene- * 1-ethylamino-3-methylbenzene yellow 4,8-disulfonic acid 136 " N-methylaniline _ " 137 "N-Ethylaniline" 138 " N- (β-13-hydroxyethyl ) aniline" 139 N-butylaniline " 140 2-aminonaphthalene-aniline slippery 3,6,8-trisulfonic acid yellow 141, "1-Amino-3-methylbenzene " 142 3-aminophenylurea " 143 ° 1-amino-3-hydrocyacetyl- " aminobenzene 144 1-Amino-3-acetylamino-6- yellow-tinged methozybenzene to orange 145 " 1-Amino-3-acetylamino-6- - rotatichigen methylbenzene yellow 146 " 1-Amino-3- methane -aulfonyl-" aminobenzene 14? "2,5-dimethoxyaniline gelatichi- gen orange 148 3-M.ethyl-6-methoxyaniline " 149r- - N-methylaniline. rotatic-higea yellow 150 2-aminonaphthalene-N-ethylane in reddish tones 3,6,8-trisulfonic acid yellow 151 "N-butylaniline " -152 ". N- (p-Hydrocythyl) -anilia 153 "3- (N-Ethylamino) -toluene " 154 M 2-aminotoluene " 155 " 1-amino-2,5-dimethylbeasol very red: yellow 156 "1-Amino-2-methosybenzene strongly rotten chigea yellow 157 "1-Amino-3-methozybenzene rotstichises yellow 158 " 1-ethylamino-3-methozybenzene " 159 , "1-aminonaphthalene-6-sulionic acid 160 "1-aminonaphthalene-7-aulionic acid" 161 2-Aainonaphthalin-1-Amino-3-methylbenzene " 4,6,8-trirullonic acid 162 "1-Amino-3-acetylaminobensol" 163 1-Aminonaphthalene-1-Aaino-3-methylbene-sol yellow -2, b, 7-trisulionic acid! ; i64 "1-aminonaphthalene-6-sulfonic acid" 165 4-Nitro-4'-aminostil- -amino-3-acetylaminobenzene rotatichiges ben-2,2'-disulfonic acid yellow 166 "'3-aminophenyl resin" 167 "1-Amino-3-hydrocyacetylamino-" bsn: ol _ 168 4-nitro-4'-amino-N-methylaniline rotatichiges stilbene-2,2'-disul-yellow Tonic acid 169 "N-Ethylaniline" 170 "N-butylanilaniline" 171 " N- (D-Hydrocythyl) -aniline " 172 1- (N-ethyl ino) -3-methylbenzol " 173 aniline-2,5-diaul- 1-aminonaphthalene-6-aulion- " tonic acid 174 "1-aminonaphthalene-7-sulfonic acid" 175 "1-Amino-3-methylbenzene yellow 176 "1-Amino-3-acetylaminobenzene" 177 1-Anino-2-methozy-5-methyl-rotatichises - benzene yellow 178 "1-amino-2,5-dimethocybene sol" 179 aniline-2,4-disulfone-1-amino-2-metho: y-5-methyl- " acid benzene Example '180 65 parts of the dye of FQxmel (made by coupling dianotated 1-hydroxy-2-amino- benzene-4,6-disulfonic acid on 2-amino-8-hydroaynaphthaln-6-aul-:, acidic acid and coppering of the obtained azo dye) are in 700 parts of water dissolved neutrally: 22 parts of 2-methylsulfonyl-Q- chloro-6-methyl-r, yrimidine is added and the mixture is stirred at 60-650C with constant dulling of the acid released with soda solution to pH 7-7.5, until no more free amino groups can be detected is. The resulting reactive dye of the formula erird * unsalted, abfltriert, washed and dried at 30 - 40 ° C overall dries. He stains according to one of the methods given above Gslluloseeaterialien in very real ruby tones. Dyes with similar properties are obtained analogously to working method described above from the copper complexes from the Diazo and azo components listed in the table below azo dyes provided No diazo component, coupling unit, color shade on Hide wool 181 1-Hydroxy-2-amino-2-methylanino-5-hydrozy ruby benzene-4-sulphonic acid naphthalene-7-eulphonic acid 182 - "2-ethyl-amino-5-hydrozy-" naphthalene-7-sulfonic acid 183 "2- (B-Hydroz'äthylaaino) - " 5-hydrocynaphthalene-7-sulfone acid 184 "2-Amino-8_hydrozynaphthalin- " 3,6-diaulfonaic acid 185 1-Hydrozy-2-amino-2-Amino-5-hydrozynaphthalene- " benzene-4,6-diaulfonic-1,7-di-sulfonic acid acid 186 2-amino-8-hydroxynaphthalene- " 3,6-disulfonic acid 187 "2-methylamino-5-hydrozy- " naphthalen-7-sulfonic acid 188 "2-ethylamino-5-hydrozy-" anphthalin = 7-aulfona acid 189 "2- (ß-Hydroxyäthylamino) -5-hy-" - drozynaphthalene-7-aulphonic acid 190 1-Hydroxy-2-amino-1 = amino-8-hydroxynaphthalene violet benzene-4,6-disulfonic-3,6-disulfonic acid acid 191 "1-Amino-8-hydroaynaphthalene-" 4,6-dinulfonic acid 192 1-Hydroxy-2-amino-1-anino-8-hydrazynaphthalene violet bensol-5-sulfonic acid 3,6-diaulfonic acid 193 "1-Amino-8-hy.drozynaphthalin-" 4,6_disulfoneaure 194 1-hydroxy-2-amino-4- 1-amino-8-hydrozynaphthalene blueet, acetylaminobenzene-6- 3,6-disulfonic acid violet sulfonic acid ` 195 1-Hydroxy-2-amino-4- 1-ethoxy-8-hydroxynaphthalene " acetylaminobenzene-6- 3,6-diaulionic acid sulfonic acid (4th acetylamino group then saponified) 196 "1-Amino-8-hydroxynaphthalene. Blue 2,4-diaulfonic acid 197 "1-Amino-8-hydroxynaphthalene-" 2,4,6-triaulfonic acid 198 1-Hydroay-2-amino-1-amino-8-hydroxynaphthalene blue 6-acetylaainobenzene; - 2,4_digulfonic acid 4-sulfona acid (6-atom acotylasino group saponified) 199 1-Amno-2-hydroxy-6- ". nitronaphthalene-4- sulfonic acid (6-atom nitro group subsequently reduced to -NH2) 200: 1-Amina-2-hydroxy-6- 1-Amino-8-hydroxynaphthalene- " nitronaphthala-4, 4, 6-trisulfonic acid. sulfonic acid (6-valent nitro group subsequently reduced to -NN 2) 201 1_gydrozy-2-nrino-6- "M acotylarinobenzene-4_ aulfonaäuro (6- position acotylamino group saponified) Example 202 One proceeds as specified in Example 30, but coupling the diazotized that reactive group-containing intermediate in sodaalkalischem medium instead of 47 parts of the sodium salt of 1-benzoylamino-8-hydrozynaphthalin-3,6-disulionsäure with 40 parts of the sodium salt of 1- Acetylamino-8-hydrozynaphthalene-3,6-disulfonic acid and isolates the resulting dye of the formula in the manner indicated in Example 30. The water-soluble dye dyes cellulose materials according to the Klotz-Damping or. Klotz-Thermofizier method (at 14,000 in white-etchable, wet, rubbing and lightfast bluish-tinged red tones. Example 203 The solution of 19.5 parts of the sodium salt of 1-aminobenzene -4-sulfonic acid and 6.9 parts of sodium nitrite in 200 parts of water is added to a mixture of 100 parts of ice and 28 parts by volume of concentrated hydrochloric acid allowed to shrink, and then half an hour is carried out at 0 - stirred 100C, and then excess nitrous acid is removed to the resulting Dia.:. osuspsnsion are added at 0 ' - 10 ° C the cooled and thus partially cooled crystallized solution of 26.2 parts of the potassium eel of 1- Amino-naphthalene-8-sultonic acid in 250 parts of hot water and and dulls the strongly acidic coupling mixture at 10-200C careful addition of sodium hydroxide solution to pH 4. The clutch is ended quickly; the aminoazo dye formed is 100 parts Table salt is completely removed, vacuumed off, washed and again dissolved in 500 parts of water at 10 ° C and pH 6-7. The watery one Solution is mixed with 25.0 parts of 2,4-bis-methylsulfonyl --- 6-methyl-pyrimidine was added and the blunt the released acid with soda solution to pH 7-7.5 Stirred at 55-60 ° C for one hour. If there is no more aminoazo is detectable, the partially precipitated reactive dye is the formula Salted out with 40 parts of table salt , filtered off and used for cleaning nochaaja dissolved in 800 parts of warm water. After clarifying the solution is made from the filtrate by adding 80 to 100 parts of cooking salt the deposited. After filtering, Drying at 35 ° C. and grinding gives a yellow powder that is in wiener easily dissolves with yellow color and the cellulose fibers according to one of the above dyeing processes in the presence of acidic binding agent in very good wet, light and chlorine-fast yellow tones colors. Also be on wool and polyamide fibers; true yellowing obtain. _ --- s If one proceeds as indicated above, but instead of the 19.5 parts of the sodium salt of 1-aminobenzene-4-sulfonic acid, equivalent amounts of the diazo components listed in the table below are coupled to 1-amino-naphthalen-8-sulfonic acid , one obtains after acylation with 2, Q-bis-methylsulfonyl-6-methyl-pyrimidine also valuable yellow to brown active colorants. Diazo component shade on Cellulose fiber 1-aminobenzene-2,5-disulfonic acid reddish-tinged a yellow 2-amino-naphthalene-4,8-disulfonic acid . strongly rotatichiges yellow 2-amine-p-naphthalene-5,7-disulfonic acid " 2-amino-naphthalene-6,8-disulfonic acid " 2-amino-naphthalene-3,6,8-trisulfonic acid 2-amino-naphthalene-4,6,8-trisulfonic acid " 4-amino-azobenzene-3,41-disulfonic acid yellowish brown 4-Amino-2-acetylamino-azobenzene-2 ', 5'-disulfonic acid orange brown so, @ ta N = N NH ,, rotatichiges So @ Na \ Braun SO @ Well (1-aminobenzene-2,5-disulfonic acid acidic to 1-amino-naphthalene-6-sulfonic acid coupled) Diasocoaponente hue on Cellulose fiber rotatichiges brown SOSNa \ / NUN / 1 P4 H. 503Na so3N @. (b.7) (1-Aminobsozol-2,5-diaulfonic acid acidic the technical mixture of 1-aminonaphtha- lin-6- and -7-sulfonic acid coupled) - SO; Well m = N -? 7 purple-tinged brown AOi 5 A --a 503Na So3Na (1-Amino-naphthalene-2,5,7-triaulfonic acid acidic to 1-amino-naphthalene-6-aulphone acid coupled) 50SNa OCHS N = N MHz rotational brown Na035 CHs 503 Well (1-Aaino-naphthalene-2,5,7-trisulfonic acid acidic to 1-amino-2-methozy-5-methyl- benzal coupled) Example 204 When cellulose fabric printed with a printing paste in kilograms 30 of the dyes described in Example 18, 100 g urea, 300 g water, 500 g alginate g (60 g sodium alginate per kilogram of thickening), 10 g of sodium carbonate and 10 g of sodium - contains salt of 3-Ni $ uben2ol-sulfonic acid and which was made up to 1 kg with water, then dried and then steamed in a suitable steamer for 30 seconds at 103 to 115 ° C , so you get a strong after rinsing and boiling soaps bluish red print with good wet, rub and light fastness.

Example 205 A mixture of the solutions of 65.5 parts each of the chromium 2: 1 complex and the cobalt 2: 1 complex of the dye of the formula in 400 parts of water each is stirred with 50 '"rush of finely powdered 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine for about 2 hours at 60 ° -70 ° C. while maintaining pu 7 - $. If no aminoazo dye ( Co complex: blue; Cr complex blue-green) is more detectable, the resulting mixture of the two reactive dyes is salted out with potassium chloride, filtered off and dried. The dye delivers on cellulosic materials according to the Pad dyeing process or under pressure in the presence of acid-binding agents s Medium strong, very good black tones that are fast to water and lightfast. If you proceed accordingly, however, the mixture of chromium 2 : 1 - and cobalt 2 : 1 complexes of the following aminoazo dyes are used, you also get valuable black dyes: Diazokoaponente coupling component coupling pH 1-Hydrozy-2-anino-4- 1-Hydrozy-8-amino-naphthalene-9 nitrobenzene 3,6-disulfonic acid 1-Hydrozy-2-anino-4- 9 nitronaphthalene-7-sul- fonic acid Example 206 To the neutral solution of 53.15 parts of the Dinatriu'- salting by coupling of diazotized 1-amino-4-nitrobenzene-2- sulfonic acid with 1- (2'-chloro-5'-eulfophenyl) -3-methyl-pyrazolone- (5) followed by reduction of the nitro group with sodium sulfide obtained Aainoazo dye in 300 parts of water 25.0 parts of 2,4-bis methylsulfonyl-6-methyl-pyrimidine and stir the mixture Hour at 55 - 60 ° C, whereby the released acid - continually blunted with soda solution to a pH value of 6.5-7 . The deposited dye of the formula is filtered off, in 3000 parts of water at pii 6 - 7 dissolved hot and re-precipitated from the filtered solution by the addition of sodium chloride. After filtering off, drying and powdering, a yellow, readily water-soluble powder is obtained which dyes cellulose materials from a long liquor at 60 ° C. or, using the cold padding process with soda as an acid-binding agent, in clear, washable, rub- fast and lightfast yellow shades. If one proceeds as indicated above , but instead of the aminoazo dye used there, equivalent amounts of the aminoazo dyes made up of the components listed in the table below are used, valuable new reactive dyes are likewise obtained. In the table, the expression "saponified" means that an acylamino group contained in the aminoazo dye has been subsequently saponified, while the expression "reduced" means that a nitro group contained in the diazo component is reduced to the amino group after coupling, whereby the desired aminoazo color forms. In the case of diaso component, azo component, pH of the hue game coupling cellulose No , nediums 207 1-Arino-4-nitro-i- (4'-sulfophenyl @ 5-6 yellow benzene-2-sulfonic acid 3-methyl-pyrazolone- (5) (4-, permanent nitro group then reduced) 208- - 1- (4'-suliophenyl) - ' 5-6 rotatiched 3-carbocy-pyrazo lon- (5) 209 "1- (3'-sulfophenyl) - 6-7 yellow 3-methyl-5-amino pyrazole 210 1-Amino-3-acetyl- 6 - ? " amino-benzene-6- sulfonic acid (3-position acetylasino group then saponified) 211 "1- (ß-IIydrocyäthyl) -15 - 6 " 3-methyl-pyrazolone- _ (5) 212 2 Hol 1-amino-3- 1 mole bis-pyrazolone 15-6 " acetyl-amino-benzene- from 4,4'-bis-hydrazino- 6-sulfonic acid (dibenzyl-2,2'-disulfone- soaps) "acid and acetoacetic ethyl ester 213 1 Hol 1-amino-3- 1- (4'-sulfophenyl) -j5 - 6 " _ acetyl-amino-benzene- 3-carbocy-pyrazolone- 6-sulfonic acid (ver (5) soaps) In the case of diazo component, azo component pll of the hue play clutch on cell No mediums loose 214 1-Amino-5-acetyl- 1- (4'-sulfophenyl) - 5 - 6 rotst. amino-naphthalene-3,7-3-carboxy-pyrazolone gel diaulfonic acid (ver (5) soaps) 215 1-Amino-2-methyl-2-acetylasino-5- 7-8 Orange benzene-4,6-diaulfone- naphthol-7-sulfone- acid acid (saponified) 216 " 2-Acetylaaino-8- 7-8 red naphthol-6-sulfone- acid (saponified) 217 1-Amino-2-methyl-1-chloro-2-acetyl-7-8 orange benzene-4,6-disulfone- amino-5-naphthol- acid 7-sulfonic acid (ver soaps) 218 1-aminobenzene-2- 1-acetylamino-8-hydroxy- sulfonic acid naphthalene-4,6-disul- 7 - 8 red Tonic acid (saponified) 219 2-Arinonaphthalin- 7-8 bleust. 3,6-disulfonic acid red 220 2-aminonaphthalene- 7-8 bleust. 3,7-disulfonic acid red 221 2-aminonaphthalene - 7-8 bleust. 4,8-disulfonic acid red 222 2-Aminonaphthalene-3,6-1-acetylamino- 8-7-8 bleust. disulfonic acid hydrozynaphthalene red 3,6-disulfonic acid (saponified) Hei- Diaso component Azoko = component pH the color tone play clutch on Cellu-- No. mediuma loose 223 2-Aainonaphthalin- 1-Acetylamino-8- 7-8 bluish. 4,8-diaulfonaic acid hydroxynaphthalene red 3,6-disulfonic acid (saponified) 224 1-Aaino-4-ethoxy-2- (N-acetyl-N-methyl-7-8 gelat. benzene-2-sulfonic acid anino) -5-hydroxy- red naphthalene-7-sulfone- acid (saponified) 225 2- (N-acetyl-N-methyl- 7-8 red amino) -8-hydroxy- .naphthalene-6-sulfone- acid (saponified) 226 1-asinobenzene-2- 7-8 " .sulfonic acid 227 1-aninobenzene-3- "7 - 8" sulfonic acid 228 1-asinobenzene-4- 7-8 " sulfonic acid 229 1-Amino-4-sethyl- " 7-8 bensol-2-sulfonic acid 230 1-Arino-2,4-dimethyl- 2- (N-acetyl-N-methyl-7-8 red benzene-6-aulfona acid amino) -8-hydroxynaphtha- lin-6-sulfonic acid (ver soaps) 231 "2-acetylamino-8-7 - 8" hydroxynaphthalene - 6-sulfonic acid (ver soaps) At- diazo component A.zokomponente pH of the hue play coupling on cellu- No mediums loose 232 1-amino-2,4-dimethyl- 2-acetylamino-S-? - S red benzene-6-sulfonic acid, e hydroxynaphthalene 3,6-disulfonic acid (saponified) 233 4-Aminoazobenzene- 1-Amino-3-aacetyl- 5 - 6 yellow- 3,4'-dieulfonic acid aminobenzene brown 234 1-amino-3-hydroay- 5-6 acetylaminobenzene 235 1-amino-naphtha.lin- 5-6 6-sulfonic acid 236 "1-amino-naphthalene- 5-6" 7-sul f on® acid 237 ° 1-Amixao®2- (41-amino- 8 black ", 2 ° -sulrophenyl- (1 °) - azo) -8-hydroxynaph & Ih "a-" lin-3,6-disulf®aoic acid Example 235 52.4 file of the sodium salt of 4- (L ° '-Aminophenyi aamino) - 2'®mitro-dipäaenylamirn-3,4 ° -disulf®nsäure e-ierden in 1000 hurry Dissolved water and with 25.0 parts of 2944mBis-methylsulfonyl-6-methyl- pyrimidine stirred for one hour at 5.5 - 65oC. The free satire buying with Sode to a p11 value of 6,5 - ', 5bluntfto The formed rehtive Nitrofarb®toff der formula @ ~ - .. Agate salts, filtered off, washed and dried. He colors Cel_ 3se fibers from long liquor or according to one of the usual Klotz method in the presence of soda as an acid-binding agent in wet and rub-fast, deep violet brown tones. Example 239 The neutral solution: of 54.7 parts of the disodium salt 1-Amino-4- (2 # -methyl-3 ° -a: innpheny l) -amino-anthrac hinon-2, 5Ld i- sulfonic acid in 1000 parts of water is mixed with 22.0 parts - 2-bidhylsulfonyl- 4-chloro-6-methyl-pyrimidine for one hour at 65 ° C stirs. The hydrochloric acid released is - with solo solution - continuously blunted to a p11 value of 6.5 -7s5. After finished Implementation is the resulting effective dye of the formula cream salts, filtered off, gewaeci = k -; and dried at 30-40 ° C: He fabtella @@ Se :: atsri.Flic@x AL is very good wet, rub and light real little blue tones. Blue dyes of similar properties are obtained by proceeding as above, but instead of the water-soluble aminoantlirachinonderivates mentioned there, equivalent amounts of the A, minoanthraquinone sulfonic acid derivatives with 2-diethylsulfonyl-4-chloro-6-rrieihyl-Pyrl: ni " ir, aeylated: Water-soluble Amino®anthraquinone derivative game - . No. 240 1-Amino-4- (3'-aminophenyl) -amino-anthraquinone-2,5'-di- sulphonic acid 241 1-Amino-4- (2'-chloro-3'-aminophenyl) -amino-anthraquinone- 2 5'-disulionic acid 242 1-Asnino-4- (2'-methyl-3'-methylaminophenyl) -amino-anthra- chinuu-2.5 ° -disul $ 'onsdure 243 1-Amino-4- (4ti-aminol) henyl) -amino-anthraquinone-2,6,3'-tri- sul a onic acid 244 1-Amino-4- (3'-aminoplienyl) -amino-anthraquinone-2, 6,4'-tri- sul f onic acid 245 1-A.-nino-4- (4 f_aminoplienyl) -amino-anthraquinone-2, 5.3 ° -tri- sulfonic acid 246 1-Amino-4- (3`-amiiiophenyl) -amino-anthraquinone-2,5,4 ° -tri- sulfonic acid - 247 mixture of 1-amino-4- (3'-aminophenyl) -amino-anthraehinone- 2,4 ', 5- and 2,4', 8-trisulfonic acid furthermore - the derivatives post-sulfated with 5% oil at 20-300G: 248 1-ammino-4-, r4 '- (4e'-aminobenzyl) -phenylj-amino-anthrachinoa-_ 2- ulionic acid - : 249 1-Amino_4- (4 ° -a = tylaminophenyl) -aaino-anthrechinon-2- sulfonic acid 250 1-Amino-4- (3'-methylaminophenyl) -amino-ani = hrachinon-2- sulfona acid 251 1-Ämino-4- (2 ° -methylamin®phenyl) -amino-antisrachinon-2- sulfonic acid 252 1-Amino-4- (7 ° -amino-naphthyl-Z2 # 7) -amino-anthraquinone- 2-aulfona acid 253 Condensation product of 1 hol of cyanuric chloride with 1 mol 1,4-diamine-anthraquin®n-2-sulfonic acid, 1 mol aniline-2,5- diuullona acid and 1 Pto1 ethylenediamine (one side), after acylation with 294-Bie-methylsulfonyl- 6-methyl-pyrimidine has a purple reactive color. Example 254 A solution of 107 g of a mixture of gleierbea molar fractions Hupferphthalocyaain-trisulf®nsäu: re (3,3 ', 3m) -mono- m-amino®p- aulfophenylj-amide and. Hupferphthaloeyanine trisulfonic acid (3.3 ° .3 " - di- (a-smino-p-aulgophenyl) -emid winds up to 1.3 liters and pH `ei.mge represents; at 150 -550C, 40 parts of 2,4-Bi9-nethylsulfonyl-6ämethyl- pyrimidii registered. With stirring, the temperature is per Hour increased by 50C and finally several hours at 65 --70 ° C left. At the same time, the dropwise addition of 3N NaOH results in a pR of about 6.5 - 7.5 held until an average of every dye kül is provided with at least one pyrimidine residue, which: on the one hand on the consumption of the sodium hydroxide solution and on the other hand through an Amin® groups Determination can be easily determined. For work-up the dyestuff solution can be warmed up a little at the specified pli , without the reactivity of the dyestuff with the cellulose being significantly reduced. The waste separation of unreacted 2,4-Dis-methylsulfonyl-6-methyl-pyrimidine and the hydrolysis products resulting therefrom is carried out by filtration or in the separator. The reaction product is precipitated by adding 150 g of table salt per liter of dye solution. It is sucked off and. dried in vacuo or at normal pressure at about 300C. This gives 195-200 g of crude dye, which contains about 30% -Kochsalz. Most of the common salt can be removed by stirring the raw dye with 250 ml of water and suctioning it off again. The dye dyes cellulose materials according to the Klota-Theaofizierverfahren at 1400C and according to the KlG'4.z-Dä3-ipf-process in naD-, rubbing- and lightfast Tärkietöheno All of the starting material used can be used in accordance with methods known per se can be obtained, e.g. D. by being one aqueous suspension of aulfonic acid group of copper phthalate cyanine trisulfonic acid chloride at 0 - 200C 3 mol 2V4-diainobensol- sulfonic acid at a pll of about 6.5 and at the same time with 3 Hol Pyzidimm the saponification catalycierto fiebeä dno above mixture the Pc®Sulfonamide is created. A similar product is obtained if you use the starting material a mixture is used that contains the named components in the rerrat 4 : i contains. This mixture is made up of the same , Copper phthalocyanine trisulfonic acid chloride and 2 moles of 2,4-diamino benzenesulfonic acid obtained by the same procedure. Instead of the starting materials mentioned, it is also possible to use such which contain nickel instead of copper as the central atom or from copper phthalocyanine trisulfonic acid chloride (4,4 ', 4-e) or. - @. Phthalocyanine-tetrasulfonic acid-e-chlorides- (3,49,4``, 4 # 't) or -f` "48,409,41 # 1) or using other arylenediamine sulfonic acids, such as toluene-diamine- (2,4) -sulfonic acid- (5) ', 4,4r- Diamino-dibenzyl-disulfonic acid- (2.2 '), naphthylenediamine- (1.5) - disulfonic acid- (3.7). Such products and theirs Manufacture are described many times in the patent literature. Your urposition with 2,4-bis-methylsulfonyl-6-methyl-pyrimidine or 3,6-bis = methylsulfonyl-pyridazine can always be made in the same pasture . This also applies to the conversion of 2-methylsulfonyl-4-chloro-6-methyl- pyriaidins with the leading to green hesitant dyes Copper and nickel-phthal.ocyanine intermediates such as those used, for. $. by polysulfochlorination of tetra- (3,3 ', 3' °, 3 '") - (p - tolyl- sercapto) copper phthalocyanine since chlorosulfonic acid, condensation from 1 to 2 sulfochloride groups per molecule with 1,3-phenylene dias <in "4-sulfonic acid or 1,4-PtaerLylenediamine-3-aulfona acid and s: ifung the remaining sulfochloride groups are available; even contain the uniform or mixed amine and sulfo groups Arylation and Alkylieruagsprodukt e of Tri- and Tetraaercapto- copper (or nickel) phthalocyanine: can pass through in an analogous manner Acylation of its amino group ni, 2,4aBis-methylsulfonyl-S-methyl-pyrimidine be converted into valuable green reactive dyes. Example 255 By proceeding according to the information to Example 18, however, the dye intermediate production obtained: @ not with the diazo-compound from 17.5 parts of 2-Aminobenzolaulfonaäure but with the Diazoverbindunfi from 20u 8 parts of 3-chloroaniline-6-aulfonsäure in the presence of 12 parts of soda with a final pH of 7 coupled no one obtains a Renktivfarbenatofff the formula with the cellulose materials now long liquor at 400C or after one of the padding or printing compounds customary for reactive dyes drive with Soda r-lo acid-binding agent in wet-fast, brilliant Red tones can be colored or printed. In an analogous manner, one obtains from the table below listed coupling components by acylation of their amino group with 2-methylsulfonylm4s chlorine -6-methyl-pyrimidine and Coupling of the resulting dye toe products with the connected given diazo components valuable reactive dyes, with . which Celluloae®aterialien in the listed tones - vorsu`e- wisely in the presence of soda - can be colored or printed: In the case of diazo component, coupling component, coupling color game PH No. 256 1_Ainz-4-methoxy- 1> Aino-8-hydroxy- 7-8 violet beuz®l-6-sulfona acid naphthalene-3,6-di- e ulfonic acid 25? e 1-amino-8-hvdroxy- 7 - 8 rotatichi- nspäathalirn-4,6-di- - ges violet sulfonic acid 258 M 2-aiaao-5-hydroxy-7 scarlet naphthalene-1,7-di- aulaeonic acid. 259 1-Amino-5-chloro-ben- - 3 '7 orange perm-2-sulph®ic acid. 260 J-inobenzene_ 9o 7 3-sulfonaic acid. 261. 1-aminobenzoi-, 7 n 4_sulfonaic acid 262 _ 2- amines -8-hydroxy- 7 8 scarlet fever naphthalene-306-di- ouläon® acid 263, 4®Aminoben-zƒe- imAmine-B-hydroxy- 7 -`S Red acid- (0- ®ulfonaphtbalin-3,6-di- ethyl) -amid eulfonic acid 264 1-aaino-4-sulfo- 7-8 violet acetylamino-ben- zol-6-sulfonic acid 265 1-Aeino-3-®ul fo- 2-ino-5-hydroxy- 7 Orange ' acetylino-benzene-naphthognaline-1,7-di® 6-®ulfonaäure sulfonaäure 266 1-Amino-4-aulfo-2-amino-5-hydrozy- 7 scarlet fever acetylamino-benzene naphthalene-1,7-di- sulfonic acid 267 1-aminobenzene-2,4-1- (21-methyl-3 ° -6 yellow disulfonic acid amino-5B-aulfoPhenyl @ 3-methyl-pyrazolone - (5) 268 2-Amino-naplithalin- "6 yellow 4,8-disulfonic acid Example 269 If one proceeds according to the instructions in Example 30, but that from 1, j-diaminobenzene-6-sulfonic acid and 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine. intermediate dye product obtained after diazotization at 100 ° C. and pH 7.5 to 6.5 with the solution of 40.5 parts of the vinodium salt of 2-sulfoacetylamino-5-hydroxy-naplithalin-7-sulfonic acid, zinen reactive dye of the formula is obtained the Cellul®sematerialaen according to the usual Altplileationsverfahren with soda as an acid-binding agent in -fast 4lranget® colors. Heisspiel 27 (i If anan proceeds as indicated in lead example 206, but instead of the aminoazo dye used there 53.15 parts of the Dinatri- nnsalrea des by coupling of diazotized 1-amino-4-nitrobenzene- 2-sulfonic acid with 1- (2'-chloro-5'-sulfophenyl) -3-methyl-pyrazolone- (5) and subsequent reduction of the nitro group with sodium sta .. - obtained aminoazo dye with the 2P4-bis-methylsüliony - 6- methyl-pyrimidine acylated as follows: is also obtained a valuable reactive dye with which cellulosic materials according to the usual dyeing and printing processes in real yellow tones can be printed. Similar reactive dyes are obtained if instead of the above gnawed amino zo dye one of the in the following Table listed components built Aminoszofarbstoffe acylated with 2-methylphenyl-4-chloro-6-methyldpyrimidine Bei- Diazo component Azo component _ color tone apiel No. 271 1-Amino-4-nitro-1- (21-methyl-4r-aulfo yellow benzene-2-eulfon-phenyl) -3-methyl-pyra- acid (reduced) zolon- (5) 2'72 @ '1- (2e, 5'-disulfophenyf yellow 3-methyl-pyrazlon- (5) `273" 1- (2 # -Methyl-4'-sulfo yellow 6'-chlorophonyl) -3-metbyl- 274 1-Amino-4-nitro-1- (2 ', 5'-dichloro-4'-yellow benzene-2-uullon-sulfopbenyl) -3-methyl- acid (reduced) pyrazolone- (5) 275 1-Amino-3-acetylamino-1- (21®Mbthyl-41-aulpho- greenish benzene-6-sulfonic acid p4enyl) -3-methyl-pyrazo-yellow (saponified) lon- (5) 276 "1- (4'-sulfophenyl) -3- greenish tint, es methyl-pyrazolone- (5) yellow 277 1- (2'-methyl-4'-aulfo-. @ phenyl) -3-earbozy-pyr, gzo- 1®n- (5) 278 " 1- (2'-chloro-4'®eulfo- phenyl) -3-caarbozypyrazo- lon- (5) Example 279 58 parts of the, dye of the formula (produced by coupling diazotized 1-hydrogy-2-amano-4- chlorobenzene-5-eulf®naic acid on 2-methylaminers-8-hydroxy-naphthalene- 6-Asulfonic acid wall copper unions of the obtained azo dyes) Dissolved neutral in 700 parts of water. You give 22j parts finely powdered 2-methysulfonyl-4-chloro-6-methyl-pyrimidine was added and stirs at 6p .650C with constant blunting of the exposed denden hydrochloric acid with Sodaläaung on PR 7 -7.5 with no free Amino group is more detectable. The reactive dye formed the formula - was salted :, filtered, genraschen and at 3.0 - 400C overall dries. Discolored by one of the methods given above Cellulose materials in very real violet tones. Dyes with similar properties are obtained analogously the working method described above from the - by simple, dehydrating or oxidizing copper plating obtained - copper complex of the diazo- and azo components produced mono- and disazo dyes: Hei- diazo component azo component coupling color shade game - pgi No. 280 i-Hydroxy-2-amano-? - Amano-8-hydroxy- 10 rotet. 4mchiorbenzene-5- nephthalene-3, b- violet sulfonic acid däeulfonic acid 281 " 1-amino-8-hydroxy-10 bluust. naphthmlin-3,6- violet diaulfonic acid 282 2-Amino-naphthalene-2-hydroxy-6-ace-8-9 rotet. 4,6,8-trisulfonic acid ylamino-naphtba blue (oxidizing copper-plated) lin-4-sulfonic acid (saponified) 283 1-.imino-2-hydroxy-1-hydroxy-8-ether-10 blue 6-nitronaphthalene-oxy-naphthalene- 4-sulfonic acid (re-3,6-disulfonic acid dued) 284 1-hydroxy-2-amino-2-hydroxy-3-amino-10 red benzene-4,6-disulfon- naphthalene-5,7- acid disulfonic acid 285 2-amino-naphthalene- "8-9 blue 4,8-disulfonic acid (oxidizing copper-plated) 286 2-aminonaphthallmm- 2-hydroxy-3-amino-8-9 blue 4,6,8-trisulfonic acid naphthalene-7-sulfone (oxidizing coppery) acid 287 3-methoxy-4-amino-6- 2 = methylamino-5- g marine methyl-azobenzene-2 !, hydroxynaphthalene blue 4 ° -disulfonic acid (ent- 7-aulfonic acid methylating coppered> 288 2®amino-8-hydroxy- 10 " uaphthalene-3,6-di-. sulfonic acid 289 2-9ino-5mhydr®uy- 10 °° naphthalene-1,7mä- sulf ommgic acid 290 3-Methoxyokioamammo- 2-Mothyl, - Iminom5® 10 Marimme- 6-motMy1-nz®benzel® hydrozynephthalin- blue 2 ° 95 ° ®dns @ nläonäinr @ 7®nulgƒn® acid (overall entmethylierend copper-plated) 291: 3-methoxy-4-asino-2-amino-8-hydrozy-10 navy blue 6-ethyl-azqbenzene- naphthalene-3,6-di- 2 '°, 5'-disulfonagure eulfona acid (demethylating ge. head ert 292 N 2- A nna-5-hydroxy-10 naphthalene-1,7-di- sulfonic acid 1- -i e 29 If one proceeds according to the information in Example 239, however, sets instead of the 547 parts of the disodium salts mentioned there 1-amino-k- «2'-ethyl-3'-aminophenyl) -amino) -anthraquinone-2,5-di- aulfonaäure'63.5 parts of the trisodium salt of 1-amino-4 - ((3 ° - Aninophenyl) -amino) -anthraquinone-2; 4 ', 6' - (or; 2.2 ', 6 °) -triaul- , fonaäure a reactive dye is obtained, the cello - loaefibres after a c @ er usual dyeing process in very good wet, clear, reddish shades of blue. When using equivalent amounts of 1-amino-4 (3 '- »inophenyl- Asino) anthraquinone m2,5,8-trigulfopaic acid is also obtained a valuable reactive dye; the cotton in real gray atichig blue tones. Example 294 30.4 parts of 2-amino-B-ozyaptathalin-3,6-disulfonic acid are used dissolved neutrally in 300: rapid water, warmed to 60-65 ° C and 20 parts of 2'4-bis-methylsulfonyl-6-methyl-pyrimidine were added. Over the course of an hour, 40 parts of 15% soda solution are used added so that the pH is between 61-e7.5. The Acy lation product partially fails . A freshly prepared Diazoniuasalslötung from 13.6 parts p-Aminobenaylsulfonic acid is at 0 - 50C in the with 12.5 parts . Soda Suspended suspension of the l3.0tiliejiimg $ product dripped. After stirring for five hours at ice bath temperature, the mixture is salt out ". sucked off, with diluted saline solution. washed and dried be9 -30®C in a vacuum drying cabinet. The dye obtained corresponds to the formula If one proceeds as indicated above, but instead of 30.4 parts of 2-amino-8-oxyeiaphthalene-3,6-disulfonic acid 30.4 parts 2-Amino-5-oxynaphthalene-1,7-disulfonic acid with 2-methylsulfonyl-4-chloro 6-methyl-fyrimidine acylated and the reactive groups containing coupling component with diazotized p-aminobe: izylsulfon- acid, one obtains a readily soluble reactive dye, the fabric containing cellulose fibers in brilliant red embroideries Orange tones. Cotton or cellular tissue is impregnated onto one Foulard at 20-25'C with an L®-aung that contains 30 g per liter of liquor of the dye described in this example, paragraph 1, 100 g Contains flarnea and 20 g of soda, squeezes on a moisture- Retain from approx. 100% and roll up the damp tissue again. After standing for 24 hours at room temperature, the fabric is rinsed, Soaped at the boil in the usual way and dried. You get one brilliant scarlet colored dyeing of good wet and light fastness. Cotton or Zeelwool fabric is impregnated on a padder at 20 - 250C with a solution containing 30 g of the in serve example, paragraph 1, described dyes, 100 g urea and 20 g soda: contains, squeezes to a moisture content of approx. 100% and steams for 30 seconds at 1030C. After rinsing, boiling . Soaking and drying you also get a brilliant scarlet colored dyeing with good wet and light fastness. Boom wool fabric is impregnated with a solution of 20 - 250C eiert, which contains 20 g of the dye obtainable according to this example, 1, and 0.5 g of a non-ionic wetting agent (e.g. a polyoxyethylated oleyl alcohol) and 150 g of ammonia and 15 g of hatrium bicarbonate per liter of liquor. The fabric is then squeezed between two rubber rollers to a moisture content of approx. 100.6. After intermediate drying at 50 - 600C 10 minutes is 1400C-heated and purged so ER- maintained coloring thoroughly with hot water and boiling for 10 minutes with a solution containing per liter 5 g Mars Edler soap and 2 g sodium carbonate. After rinsing and drying, a strong scarlet coloration with good wet and light fastness is obtained. If cellulose fabric is printed with a printing paste that is 30 g in the kilogram of the one described in this example, paragraph 1 f4.--t8=@affs, 100 g urea, 300 g water, 500 g alginate thickening (60 g ° v . Trium algnate per kilogram of thickening); 10 g of soda and Contains 10 g de @ sodium salt of 3-nitrobenzene sulfonic acid, and which was filled with water to 1 kg, then between drying for 30 seconds at 103 and in a suitable damper - attenuates 1150C, so after rinsing and soaping at the boil to obtain a strong scarlet staining with good fastness properties. 100 parts of wool are introduced into a bath at 40 ° C. which contains, in 5000 parts of water, 1.5 parts of the dye described in this example, paragraph 1, as well as 6 parts of 30 % acetic acid and 0.5 part of a polyoxyethylene hydroxyl-containing stearylamine derivative . The dye bath is brought to a boil in 30 minutes. brought, then an hour is dyed boiling. After rinsing and dryness you get a brilliant,: easy to wash, tumble and lightfast scarlet coloration: Example 295 Man .dianotiert 28.9 parts of 2-amino-1-methylbenzene-3,5-disulfone acid (Mononatriuaaal $) and couples the Diazoaerb-dung with 13.7 t: 1-Amimmo-2-methozy-5-methylbenzene in weakly acidic medium. Of the Kanoazoi obtained is isolated and then or else Immediately diazotized in solution without Isolieruni and with 25.3 parts 2-Methyluisno-5-hydrozynaphtbalin-7-sulfonic acid coupled with alkaline . The disazo dye obtained is made by adding sodium chloride lined up, sucked off and the isolated . Product : with approx. 50 parts crystallized copper sulfate, -40 parts disthanolanine, 50 parts Aaaonia (D: 0.88) metallasized for 5 hours at 95-100 ° C. From the coppering solution, the dye is obtained by adding salt and: careful acidification isolated. The iekuleferte amino-disazo dye is nu ÜR in aqueous Solution at PH 7 - ö .at a temperature of 6o -65 ° C with 22.0 parts 2-methylsulfonyl-4-chloro-6-methyl-pyrimidine acylated, - whereby the pH-Vert is kept in the specified range by Sodasusats. After acylation is complete, the dye is treated with sodium chloride isolated and dried at 350C. The dye corresponds to in Fora of the free Sullona acid of the formula: he dyes cellulose fabric according to the knew processes in wet and lightfast navy blue tones. In a similar way, further inventions can be made Produce dyes if you use the above-mentioned monoaso color atoff from 2-amino-1-methylbenzol-3,5-disulfonic acid and 1-amino- 2-methozy-5-ethylbenzol with the values given in the following table led aminonaphthol sulfonic acids and 2-ethylsulfonyl-4-chloro 6-methyl-pyrimidine according to the instructions given above combined. Coupling component 2TAmino-5-hydrozynaphthalene- 1,? - diaulfona acid 2-amino-8-hydroxynaphthalene, 3,6-diaulfonic acid The dyes obtained are blue in color Example 296 0.1 Hol 4-ureido-2-amino-1-hydroxybenzene-5-sulfonic acid dianotized and soda-alkaline with 0.1 Hol 1-Amino-S-hydroxy- naphthalene-2,4-diaulfonaic acid coupled. The coupling solution is adjusted to a content of 2 Hol / liter with ÄtZuatron provides and then 3 hours under reflux to saponify the Boiled ureido group. After cooling down, hydrochloric acid is used neutralized. By adding 25 parts of copper sulfate and 100 parts of 2N sodium hydroxide solution is the dye at 450C and one pH value of 4 - 6 metallized and after 30 minutes hot pü T - 795 and temperatures of 60 - 70'C with 0e1 mol of 2-methylsulfonyl-4-chloro 6-methyl-pyrimidine acylated. The dye obtained the formula is gummed up. A blue dye is obtained on cotton. Example 297 A neutral paste of copper phthalocyanine-3,3 ', 3 "- made from 600 g of technical grade 96% isem copper phthalocyanine t2io # = 1fonsäurechlorid is mixed with a little water, to 4 l eing4_ Pllt and at a pH of 3.5-6.0 with 216 g of N-methyl-N- (4'-amini-2'-aulfobenzyl) -amine at the beginning of 0-30C, finally 20-350C, with the addition of 300 ml (= 295 g) of pyridine and then the pyridine is reacted at pH 9.0 with steam the resulting solution of copper phthalocyanine-diaulfonic acid-monosulfonic acid- (3'-sulfo-4'-methyl-aminomethyl-anilide) is distilled off. In the solution, brought to 600C are partly 3'j0 g of finely powdered 2,4-bis-methylsulfonyl-6-methyl-pyrimidine in the course of 1 to 2 hours and interspersed by addition of dilute sodium hydroxide solution, a pH from 7.5 to 8, 5 maintained. At the same time, if necessary, the reaction chemical is diluted with water to such an extent that the dye always remains dissolved. 10 l of dye solution are obtained, which are removed from excess Aeflierunssaittel separated off by adding acetic acid to pH 7.0 represents and by stirring in 2.3 1 concentrated Kocheals-. solution falls. After cleaning off and drying at 30.degree. C. , a clear one is obtained turquoise-blue dye, which is produced from a soda-alkaline solution at 4- 60 ° C with, very good sweat and wash fastness on @ Bauawolle is fixed. If the NiPc-3,3 ', 3 "-trisulfona acid chloride is used as an sanssnaterial, you get a turquoise blue that is only a little greener with equally valuable properties. Example 29 $: 0.1 riol of the aminoazo dye of the formula - prepared as in the German patent 1,115,865 - (application F 27466 IV b / 22 a) by coupling the diazonium compound of 2-aminonaphthalene-4,8-disulfonsüure with 1-Aminonaphtbalin-6-sullonsäure. Further diazotization of the aminoazo dye obtained, coupling with the equivalent amount of 2,5-diaminonaphthalene-4,8-disulfonic acid and conversion into the aminotriazole - are dissolved in 1000 parts by volume of water at pH 6 and, with stirring, at a temperature of 60-659b with 21 Parts of 2-methylsulfonyl-4-chloro-6-methsl-pyrimidine are added. The slowly released hydrochloric acid is blunted with soda solution until the reaction has ended. The dye is then deposited by adding sodium chloride, isolated and dried at approx. 50% in vacuo.

Fr represents a yellow, soluble in water with a yellow color powderrepresent. Hehapiel 299 38.9 parts of the soda-alkaline coupling from 6-nitro-2- diazo-1-hydrozybenzene-4-sulfonic acid and 2-Ilydrozynaphthalin Holding dye are in 200 parts of water at pH 8 at a temperature of 70 - 800C. In this suspension one carries 67.9 parts of 1 chromium atom for 1 molecule of dye containing Chronkomplezverbindungen of azo color from 4-chloro 2-diazo-i-hydrozybenzene-6-sulfonic acid and 1-amino-8-hydroxy- naphthaiin-3,6-disulfonic acid, the pH being adjusted by adding dropwise Soda solution is kept between 7 and 9. After 20 minutes at 70 - 800C a dark blue solution has formed. The paper- chromatoaranni shows that a uniform mixed complex is standing. The mixed complex becomes within an hour at 650C and pH 7 - with 25.0 parts of 2-diethylsulfonyl-4-chloro-6-methyl- pyrimidine acylated, the pII by adding dropwise soda solution is kept in the specified range. The acylated color The substance is salted out with 20% potassium chloride, filtered through and with 30 ° C dried. A dark powder is obtained that dissolves in water dissolves with a blue-gray color. The dyestuff corresponds to the formula as a pentanatrium salt It dyes cotton according to that given in Examples 1-3 Process in gray to black tones. From the starting components specified in the following table Valuable dyes can also be annoyed in the in in this example. For the preparation of these dyes was always the azo dye, which was mixed in 2: 1 complex carries the reactive group, used as a 1: 1 chromium complex. 62) 0 parts of trisodium salt from the soda-alkaline coupling dianotated 4-chloro-2-amino-1-hydroxybenzene-6-sulfonic acid and 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid obtained color stoffc are in 300 parts of water at? 0 - 800C and a pH of 8 - 9 with 54.2 parts of the 1: 1 chromium complexes of the dye from 6-nitro-l-diazo-2-hydroxynaphthalene-4-sulfonic acid and 2-liy- added droxynaphthalene. After 10 minutes, a deep blue solution formed. The mixed complex will be at in about an hour 60 @ - 650Cand one pH from 6.5 -7.5 with 25thShare 2-methylsulfonyl-4-chloro-6-methyl- Acylated dyrisidine. The pfI value is hereby added dropwise kept constant by soda solution. The acylated dye will separated with 20% sodium chloride, sucked off and at 300C On tree full one obtains according to the procedure given in example 3 drive a blue-black print of excellent light and Washfastness. Example 3'25 6-s I -. @ Turao-4 - (@@ - aminophenylasino @) @ anthrachnoa-2,5,8-tri- sulfoic acid are dissolved as Na salt in 180 n1 water at 40 ° C, the solution adjusted to pH 8 and at 65-700C 2, 5 4; 2-methyleulfonyl- 4: -chlor-6-methyl-pyrimidine in small portions registered. Dilute sodium hydroxide solution is left on the same side add dropwise, so that a pH of 7.5 - 8.5 is reached during the reaction. will hold. The mixture is stirred at 65 - 70 ° C until everything Outgoing material has disappeared, sucks up excess Pyrimidine derivative and salt at lpoC with so much solid Sodium chloride, so that B about a 10% sodium chloride solution is present. You wash off, wash with a little saline and dry the obtained dye of the formula below 400C in a vacuum. About 8.5 g of the dye are obtained in the form of blue-green needles. The dye re-dyes cotton for reactive dyes usual procedures in strong blue-green tones of good NaD- and lightfastness. The 1-amino-4- (41-asino- phenylaaiao) -anthraehinone-2,5,8-trisulfonic acid was made as follows obtained: 31.2 g of p-phenylenediamine are placed under nitrogen in a Solution of 62 g of 1-amino-4-brow-anthraquinone-2,3,8-trisulfonsanres Sodium and 12 g of soda entered and with the addition of CuCl paste Stirred at 40 ° C until no disulfated bromic acid is more detectable. Now the solution is mixed with dilute salt acid, the precipitating dye is sucked off, with washed with dilute hydrochloric acid, in 300 ml of water with as much mixed with a thin sodium hydroxide solution so that the solution enters and the dye is precipitated in the heat as the Na salt; the "pro- The product is then washed and dried. In the aforementioned examples, the reactive components used can be the same or similar reaction conditions are exchanged with one another. Likewise the same or a similar result can be found on page 11, paragraph 2, specified reactive components in the reactions according to the preceding Use examples instead of the reactive components specified there. Ex iel 26: 79.9 parts of the Belgian patent specification No. 599581 manufactured Amine mazo compound four formula are dissolved in 500 parts of water at GO - 05 ° C and at this temperature below 21 parts of 2-diethylsulfonyl-4-ceilor-G-netliylpyrimidine are added to the mixture. here slowly released hydrochloric acid is blunted with soda solution, whereby a p11 value is held between 5 and 6.After finished condensationthe dye is made by adding 150 Parts of potassium chloride salted out, 'isolated and stored at about 50oCim Vacuum dried. A dark powder is obtained which turns blue in water Color dissolves and cotton in reddish blue tones of excellent light and Fastness colors. The following examples show parts unless otherwise stated, for parts by weight.Example 327 To the Solution of 34.7 parts of 2-aminonaphthalene-4,8-disulfonic acid sodium and 7 parts Sodium nitrite in 300 partswater give 28 parts by volume while cooling with ice concentratedhydrochloric acid and stir the mixture for 1/2 hour at 0-100C. After this excessnitrous acid has been removed. to give 10.7 parts of 3-aminotoluene dissolved in 10 parts by volumeconcentrated hydrochloric acid and 150 parts of water, added and leads the coupling by blunting the mixture PH3 -5 over. The resulting Aminoazo dye is salted out,sucked off, washed and then again in 700 parts Water underadditive fromCaustic soda PH7 solved. the aqueous Solution will on thiswith 24 Share 2-Methyl®ulfonyl-4,5-dichloro-6-methyl-pyrimidine added and stirred vigorously. The temperature of the reaction mixture is through Heating at approx. 650Cheld; the free- becoming Hydrochloric acid with soda solution until the reactioncompleted is. The resulting Dye of the likely formula is salted out with 80 parts of table salt, pressed, wash and dry at approx. 500C in a vacuum. He's hiring yellow powder soluble in water with a yellow color. . one can print cellulose fabric with a Druokpaate that in the kilogram 15 grams of the dye, 100 g urea, 300 ml Water, 500 g alginate thickener (60 g sodium alginate per kg thickening), containing 2 g of sodium hydroxide and 10 g of soda and those with Water was made up to 1 kilogram, dries, ß minutes at 1050C steams, rinses with hot water and boils, aeitt, so if you keep a strong, reddish yellow print of good washing and lightfastness. Example 328 0.1 mole of the copper complex compound of the formula '' pes soawa OH NHs N = N W & 095 O - CU - 0 S®; Ns (Produced based on the information in the German patent script 1117235) by coupling diasotized 1-amino-S (bensolsullonylozy) - napit "lis-diaslfemsäure- (3,6) in aodaalkalisehem medium since the equivalent amount of 2- # eetylamiao-5-hydrozynaphthalindisulfon- säsrh- (b, 8), ths transformation of the nonoaso compound into the tupter complex by ezydative plucking and hydrolysis of the laetyl- and the Dessol- nlies @ lgrsppe) been in 2500 Volumetric waterfrom 60 - 650C at pH6th -6.5 dissolved and at this temperature with 0.12 Col 2-methylaulionyl-4,5-dichloro-6-methyl-pyriaidinoffset. The condensation is ensured by adding sodium carbonate solution ice p «from - ; j, 5 oin4ohalton. After the reaction has ended, the Dye aussosalsoa and isolated. The dye represents dried A dark powder that dissolves in water with a blue color. 100 parts by weight of a cotton fabric have been toaperatar with a water solution containing 2% of the dye, Contains 15 g / 1 ai trihydrogen carbonate and 150: / l urea, foaladiort, zviseheasotrocknot, heated to 140 ° C for 10 minutes, nao # rinsed and soaped at the boil. The fabric becomes very clear blaaon Tinoa na # ochtly colored. Example, 329 46 Partly dos analogous to the information in Example 327 by coupling of dianotated Z-aminoaaphthalene-4,8-disulfonic acid on 3-MothYl- miao-toluel moaoasi dye are obtained in 400 parts waterfrom 60 to bj0Cat pH 'j-8solved and in presencefrom excess sodium acetateor Calcium carbonate partly with a total of 29 parts 2,4-bis-methylsulfonyl-5-chloro-6-methyl-pyrimidine offsetand stirred at this temperature until a Sample at Acidification does not change colorshows more. The resulting fax Dye the probable formula is salted out, filtered off with suction, washed and dried. Baumb.ollgevebe is impregnated with a solution at 20 - 250 C, the per liter of liquor 2 0 g of the above dye and 0.5 S one non-ionic wetting agent ( see e.g. a polyethylated oleyl alcohol and 150 g N, azn®toff and 15 g sodium carbonate. The tissue is then placed between two gumnival: s on one Moisture content of about 100 j1 squeezed off. After the interim dry at 30 - 60 °! C is heated to 140 ° C for 10 minutes and the like obtained staining rinsed thoroughly with bite water and 20 minutes treated at the boil with a solution containing 5 g of Marseilles per liter Contains soap and 2 g of soda. Receives after rinsing and drying a strong, rotatic yellow coloration of good Na®-, friction- and lightfastness. The following table shows the slide components tnpplungskonpomenten and which can be linked since the Aaino group Reactive components listed, from which analogously to the information in the Examples 327-32_9 Rarbgtoffe auff; eb = iw @ will "t -, @ inside,; ieren tune - obtained after one of the application procedures described - are also listed in the table, A - 2-ethylsulfonyl-4,5-dichloro-6- Abbreviations for methyl-pyrimidine the reactive components: B - 2,4-bis-methylsulfonyl-5-chloro-6- ethyl pyrimidine Example slide component coupling component reactive color ljr, component 330 Z-Aninonaphthalin-4,8-1-Amino-2-methozy-5-A yellow disulfonic acid tsethylbenzene 331 D -U 1-aninenaphthalene-3,6- disnlioic acid 1-amino-3-nethrlbene sol A " H 3 2 7 ., -, 334 2-ynynaphthalene-5,7- dio @ e @ ions @ tare 1-Amino-3-methylbene sol A 335 H r 336 g-VinonaPhtbalin-6.8- disulionic acid 1-amino-3-methylbenzene A 317 33a i-lsüaoasoben: ot-3, t @ - diaalic acid 1-asino-3-ethylbene sol A brown-yellow Example slide component äupplamgskoa, component reactive shade No component 339, 1-aainobensol = 4-sulion- acid -4 1-aminonaphthalene- 6-sulfona acid 1-amino-3- methylbenzol B brown-yellow 340 2- (3'-sulfo-4'-aminophenyl) - 6-methyl-benzothiazole-7-au- fonaäure " A yellow 341 2-aminonaphthalene-4,8-di- 1 --M ethylamäna-3- eul f onic acid = ethoxybenzene B " 342 "1-Awino-3-acetYlamino- benzene A 343 aniline A " Example 344 In the solution of 36.5 parts of the sodium aalsoa of the 1-aaino 8-hydroxynaphthalene-3,6-disulfoneäu.re in 100 parts of water with good stirring at 50 - 60 ° C 29 parts 2,4-bis-methylaulfonyl-5-chloro 6-nothyl-pyrinidine entered and with constant blunting of the hydrochloric acid released on p11 6 - 7 stirred until none free amino group is more machinable. That so Parabola Atoffswiachenprodukt is after dilution with 600 parts of water and Addition of 12 parts of soda at 5-100C with 17.5 parts of diasotized 2-Amiaobeasolaulfonaäure, gel @ ött in 200 parts of water, coupled. The one at a final FH of it. 7 was created, »* dye of the formula @; pj gilb hl 1 a i is suagesalsem with 100 parts of Kochaals, suctioned off, aewaschea and dried at 30 - 40o0 in vacuo. The dye forms metallic shiny red needleclea that is sick in Vaaser Leicht.sit red paint. Is made from house wool or rosemary cellulose using any of the procedures described in Examples 327-329 dyed or printed with this dye, it receives a clear blue strong red coloring and prints of good dimensional, rubbing and light- unconsciousness. Gleist good results are obtained according to the Felsemdm process: 50 grains, Hsoav @ ollstrang are in the 1 liter of a Pirboilotte, containing 1.5 g of the above dye, colored by using the Temperature within 30 misuton from the toilet to it. 800C increases, thereby inagoaaat 50 g Xocheals in aebror «-lateiles amsibt, aa- Then add 20 g of eda and 60 meows at this temperature beraaiolt. After the rinse, the boiling soap ml gets dry you get a bluish red color with good nai, rub and light Work. In the nashpolgendon table are the #arbtbe of other Parb- atoffo "led". those from the slide compo- nenten, äzppl »gahompoaentea and with the rines black horse in the letstorim verksüpfbarea Reakti.koapomente ': aala the information in s, iapiel344 - or sales of the corresponding viaoase- dyes with the rsaktirkomponentea - to be built up and asoi ' one of the processes described above on Collalosmaterialiea colored or printed verder v # can; Abbreviations for the reactor components as in the table for Example 329 In case of slide component, coupling component, reactive color play sponsor No. 345 1-aminobensol-2- 1-amino-8-hydrozy- B red sulfonic acid aaphthalene-3,6- disalfonic acid 346 1 - (; # - Aminobensoyl- A 1-arinobensol- 2-sulfonic acid imino) -8-hydrocy- Naphthalene-3,6-disulfone acid 347 aainobensol B w 348 1-Amino-2-carbos, - 1 # mino-8-hydrozynaph- A " bensol-t-sulfonaänre @ thalin-3,6-disulfonswure 349 1-Aino-4-methylbea- sol-2-sulphonic acid "A '° 35, 1-amino-3-acet'lmine- bensol-6-sultonaäare 351 1-lmino-3- (2-- , C4 --- A sulfophenylamine J-b'- chlorotriazine-1 ', 3f, 5' 71- 6 ') - aminobensol-6-snlfon- acid 352 1-aminobenzene-2-srlfea-2-amino-5-hydrezy-orange acid aaPhthalia-7-salfer- sü @ re Sei- Diasekoapeaente coupling component reactive color sriel kosponente Dr. 352 a 1-amino-3- (2 ° - 2-astino-5-hydro: y- A orange "-eulfophenyl- naphthalene-7-sulfone- asino, -4'-ethyl acid aaino-triasin-1 ', 3 ', 5'-yl-6') - aaino- beasol-6-sulfone- acid 353 1-Aainebensol- 2-Nothylanino-5-hy-A orange Z-sulfonic acid drozy-naphthalene-7- sulfonic acid 354 1-Aaino-k-acetyl- ° A scarlet fever saino-6-sulfonic acid 355 "2-aaino-5-hydrozy- A naphthalene-7-sul- fonic acid example 356 In the solution of 21 parts of the Natriuaeales_der 1,3- Diasinobenzene-6-sulfonic acid in 100 parts of water are under good Stirring 24.0 parts of Z-methyleulfanyl-4,5-dichloro-6 = methyl- pyrimidine registered and at 60 -650G under constant digem blunting the released hydrochloric acid to pH 7 - ö as long stirred until a sample is diazotized and coupled to 1-Hrdrozy- naphthalene-4-sulfonic acid has a clear, yellowish red color. gives. The resulting intermediate dye product becomes after addition of ice directly with 7 parts of sodium nitrite and 28 parts of conc trated hydrochloric acid and then diazotized with a th solution of 47 parts of the ratriuasalzea of 1-Benzoylaaino-8- hydrocyanaphthalene-3,6-disulfonic acid and 12 parts of soda in 200 parts Water combined, coupling to the dye of the formula takes place, the bus salted, vacuumed, washed and at 30 - 400C is dried in vacuum. The dye dissolves in water light with red color and delivers after one of the above described .benen processes on clear bluish red dyeings and prints -Cellulose materials. In the table below are the shades and the p8 advantage of the Kupplraseaedirmo led by Farbsteffen, the anales dem In Example 356, specifying from a slide coaponent which a contains additional binoculars that can be activated beforehand, from one Coupling component and on one with the Diasokomponeate vsr- kaiipfbarea Reaktivkeaponente be produced. For dyeing bem rag printing of wrap-around materials with the dyes of The above-mentioned procedures have been used in the table below. AY kiss roses for the reactive corponents as shown in the table for game 329 Bei- diase component Rupplunse component reactive pil des parb-- play compo- coupling K :. nent image 357 '1,3-Disminoben- 2-laiaonapbthalin- L 4-5 grams * sol-b-srlfomsär: e 3,? - dieulionic acid 358 # 2-lminonaphthalene- # 4-s " 3,6-disulfonic acid 359 # 2-Aminomapbtbalin- ä 4-S ' 6-sulfonic acid 360 2-H-MetbTlsmiao-8- A 4-5 ` hydro: ynaphthalene 6-sulfonic acids Bepl. Diasokoaponente hupplunaakoaponente Reactive pH of the color dead No coaponente Kupplaa. iedi1111 361 1,3-diaainabenzene-1- (3 ', 5'-dichloro-1', A 7-8 red 4-aalfona acid 21-thiazole-4'-carbon- asaido) -8-hydroxynaphtha- lin-3,6-dinulfona acid 362 R 1- (2 ', 4'-dihydroxy- B 7-8 triazin-1 ', 3', 51.-yl- 6'-amino) -8-hydroxynaphtha- lin-3,6-diaulfonic acid 363 1- (3 ', 5'-dichloro-1', A 7-e " ß'-thiasol-4'-carbon- aaido) -8-hydroxynaphtha- l in; , 6-di aul f onic acid 364 "2-Hydrozynaphthalin-3,6-A 8 seharlach diaulfonic acid 365 # 1-acetylasino-8-hydroxy-B 7-8 red naphthalene-3,6-disulfen- acid 366 R 1- (31-sulfophenyl) -3-ethyl- pyrasolon-5 A 6 gel 367 1- (2 ', 5'-dichloro-4'- A 6 yellow snltophenyl) -3-aathyl- pyrasolon-5 368 '1- (5'.7'-Diaulfonaphthyl-Q0-) -3-ethyl-pyrazolone-5 A 6 yellow 369 R 1- (3'-sulfophenYl) -3- B 6 methyl-5-aainopyrazole 370 1,4-diminobenzene- R-aaino-8-hydroxynaphthalite- 3-aulfanaic acid A 4-4, 6-aulfonic acid A 4-4, 'j red Depl. Diase component, coupling component, reactive pH of the color 11s. component coupling medium 371 1,4-Diaainoben: ol @ -Acetylamino-5-hydrozy-A 6-7 acharlacb 3-eolionaic acid @ naphthalene-7-sulfonic acid 372 "1-acetylamino-5-hydroa'- B 6-7 red naphthalene-7-sulfonic acid Example 373 51.6? Hurry the diasotization of 1-Hydrozy-2- »ino-bensol-4 eaalfensäare and domes on 2-amino-5-hydroaynaphthalene-7-sulfonic acid im Vaaser / Pyridine in the presence of Svda and subsequent treatment dyes of the formula obtained with a copper-donating agent OC 4A O WELL N & 035 NHa fr03Nm been dissolved in 15.00 liters of water at pH 7. While stirring well one wears at 60 -. 650C 24.0 parts of 2-riethylaulfonyl-4,5-dichloro-6-methyl pprimidin found blunt the released hydrochloric acid with soda w Löeamg continuously depends on a PH of ? -® . If no free amino group is more machinable, the reactive dye formed is of the formula sausage, preated, washed and stored in Vokw at 30 - 400C dries. Fabrics made of cellulose materials can be used with these color fabric according to one of the above-mentioned processes in wet, rubbing and lightfast ruby tones can be dyed or printed. In the following table the Schveraetallkoapleze are broad- rer Aninoaso dyes and linked to the amino group active components, as well as the color tones of these dyes on cellular " loose materials listed. The production of the aminoasofarbotoffe, their metal complexes and their conversion with the reactive components can be carried out analogously to the information in Example 373 . Abbreviations for the reactive components as shown in the table Example 329 Example aminoazo dye complex reactive color Mr. bound coapon clay Heavy metal to 374 i-Hydro = ya-aainobenaol- Cu A sabia . 4,6-disulfonic acid --i Z-Aniao- S-hydro: naphthalene-7-sulfonic acid Example Aaiaeaso dye complex reactive scar 11r. bound iompenenton Heavy metal to 375 1-Hydrozy-2-aainobensol- Ca A Ruby 4-sulfonic acid - + 2-Äthyla.ino- 5-hydrocynaphthalene-7- sul f onic acid 3'j6 1-Aäino-2-hydrozy-6-nitro-Ca .A Rubin napä * halin-4-sulfonic acid --i 2-amino-5-hydrozynaph.thalene- 7-sulfonic acid 377 "Cr A; rünatichi8 ;rough 378 1-Aaisw-2-hydro: yb-nitronaphtha- lin-4 @ -aslionaäise -i1-Aaino- Co 8 rotstichi8 8-hydros w asuhthslia-4-a m 1fon- . black Sweet 379 1-A '° e-2-hydroxy 5-sthylss1- Cis A violet tonyl-b »swl -b 1-Aeiwo-8-lrydros'- napWlhal; i: n: 3, @di ssl f oasüise 38p - # Co A gray 381 "Cr A 8rünstichi8 black 382 1-.stao-2 -amt hylbensol-4-sul- Cu H blue fonsäsre --6 1-Asino-2-hydrö: y- 5-methylbenzol - # 1-amino-8- hydrocynaphthalene-4,6-disulfone sweet 383 # Co B gray 384 p Cr A jrünatiehi8 3ehvasz- E.g. Aminaasofarbstofi complex reactive Parkton No bound . compo- Schvermetall nente 385 (1-Amino-2-chlorobenzene-4-sulfone- Cu A Marine- acid - + 1-hydroxy-2-aeetylaminobensol), blue saponified, -; i-amino-8-hydroxy naphthalene = 3,6-disulfonic acid 386 Co A gray 387 1-Amino-8-hydroxynaphthalene-4-sul- Co. A black fonsäure 4-1-Hydrozy-2,6-diaminobenzene- -4-sulfonic acid-e > 1,3-dihydroxybenzene 388 1-Amino-8-hydroxynaphthalene-3,6-di o A sulfonic acid% - 1-ilyd roxy-2, 6-diaai- nobenzene-4-sulfonic acid --a 2-hydroxy- naphthal in 389 1-Amino-8-hydrozynaphthalene-4-Co A " sulfonic acid 4-- 1-llydroxy-2,6-dia- minobenzene-4-sulfonic acid --b 3-methyl- pyrazolone- (5) Example 390 96 'file (based on 100% goods) in the usual way durc.h exposure to chlorosulfonic acid and thionyl chloride Copper phthalocyanine freshly made copper phthalocyanine tetrasulfochlorids or the isomer, from 1-sulfobensol-3,4- dicarboxylic acid via the corresponding copper phthalocyanine tetra- sulfonic acid built up copper phthalocyanine tetraauliochlorids previously in the form of the moist, well-washed suction cake in 500 Parts of water and 500 parts of ice suspended, the solution of 50 Sodium sodium of 1,3-diasinobensol-4-sulfoic acid is available for sale i® S00 parts wet addea and the pH with soda to 8.5 set. When the suspension is stirred for 24 hours at room temperature ratsr «d keeps the pH constant by continuously adding soda 8.5. The resulting condensation product is at pH 1-2 by Addition of sodium chloride precipitated, filtered off with suction, washed and then again dissolved neutrally in 1000 parts of water. In the blue solution 80 parts of 2,4-Bi®-methylsulfone, Yl-5- chlor-6-asthri-pyriaidin entered and under constant blunting with 8oda solution to pH 7-8 at 60 - 65 ° C until no free lminogroups are more detectable. The so obtained Reakti®- farbitoff the Po «el m @ lOt cg @ . @ SG @ N @ w Cm - Phfaiorrrl @ nrn tM3 (SOV ) 1N _ 301d11 @ -n the carrion is salted, washed and dried in vacuo at 30 - t0oC. 3r represents a dark blue color soluble in water with a blue color talwer and stains barolle and Mgeneratcellulose one by one of the dyeing or printing processes just mentioned in clear blue time wen good precision, rub and lightfastness. Instead of 96 parts of Zupferphthalocyaninetrasulfechlorid hiatea - with the same working method as in example 390 - also 87 parts (based on 100% goods ) of the dureb Biaffektn4 ton of chloro sulfonic acid on copper or nickel phosphate baltepaain common copper or nickel phthalocyanine trisulfechlorids in per of the moist Sauakuchenn well washed with Eiswaaoer will; you then also get clear blue reactive color fabrics. Even if one works as indicated in Example 390, however starting from 87 parts of copper phthalocyanine trisulfoehlorid and represents the 50 parts of the sodium salsa of the 1,3-Dia ei » obensol-4- sulfonic acid 90? hasten the Natriursalses of 4,4'-Dianipe-diphenpl- 2,21-diaulionic acid or 90 parts of the sodium salt of 4,4'-diamiae stilbene-2,2 '= diaulfonic acid is used, one obtains reactive dye stiffness, which cellulose materials according to one of the above drive in wet. rubbing and lightfast, clear blue tones to dye. If one goes from, 41.4 # 0.4 "', 4""- tetraphenyl-Cu-phthalocyanine to, according to Sulfochlorieruag and Usaats with 1,3-phenyl diaain-4-aulfanic acid and acylation with 2,4-Hie-methylsulfonyl-6- methyl-pyrimidine a reactive agent, the Cellslooeuateri- alien in the presence of acid-binding agents in clear "na9- and lent- true green tones. Example _1 "291 Maa dissolves 71 parts of the 1-imino-4-6rom- thr @ etbiwes-2-sr, fensäus: with overlapping .4,4'-diamiao- iddesyrl-2, t'®disrlons.ure obtained aeinoaathrathinone dyes in 700 parts of water, wrestles at 60-650C with thorough stirring 25 Part 2-ilethylsulfonyl-.4, 5-dioh'.or-6-sethyl-pyrisidine and hold by continuously adding Sedalöeang a PH ton 7-7.5 upright. if no more aminodrixppe is detectable, the result will be * Dye of the formula O 900wa 404 give N 4ce * - 1 atusesswtses, abatoau $ t, washed and dried at 50 - 400C in a vacuum net. He colors Daamnnslle and Regeaerstaellalose according to one of the above Aasetiürtes process in dimensional, rubbing and lightfast Blout nozzles. resw aas proceed as indicated in example 391, but Molle der 71? Hurries the Aasdasgsfarbenotoffe used there equi- valent neudes one of the following derivatives of the 1-anine-4- (risearyleaiae) -aathraquinone-2-oulfonsärre uses aas ähälieho dyes whose blue colorations are also similar to fast unit like that of the dye obtained above: 1-Aaiao- 4- (4 # -saise-2 # -oulfophesylaaiso) -aathraquinone-Q-sulfoasärse, 1- 1 @ ise-4- (4 # -aaia®phtsylsaise) -asthsachisos-E, 6-disulfossärre, Ieeierssa @ issY asa 1 @ iao-4 - (@ r ° -aaiaolhtsllaaiaej-asthsathises- '1,3- and. 2,8-diaulfonic acid, lsonereng®zisch zwo 1 @ rß®o-4 $ 4'- essino-2 ° -tc @ ultophenyla @ sin @ o) -srt @ sraei @ inon-2,5 @ - and . 'ä> disu @ ton- acid, fsowereageaiseh aua 1-aaino-4- (3'-aaopy @ arßno) - amthraehinon-2,5- and -2,8-disu @ fonsär @ e,: - @ Pno-4- (3'-arino- pheaxlaaino) -aatlaraehisoas-.2,6-dßsulfonshä :::. @ e a 4'-sulfopwest @ lamiao) -anthrari @ inon-2-sulfoic acid. With 1-aaino-4- _. , _iao-2 "-eulfo pieny arino-phenyl) -antirse hi aon-2, 6-di - oultona acid contains ran blar6 & tishig grae coloring reactive dyes. Example 392 Yertübrt as specified in Example373, but goes instead of the copper-containing Arinoronoaso dye used there from the equivalent amount of the Chronkorple: it des by coupling of Diäaotierter 1-Aniao-2-hydro zr -3-cilorbensol-5-aulfonic acid with . 1 -, r3 '- (3 ' -Arinopheayl 17- saltos.liaido-sultoayl-phenyl 3-reth'1- pyrasoloa- (3) obtained Aainoasotarbatottes from, so ran a gsaktivtarhstoff, which cellulose materials after a the above-mentioned methods in good dimensional, rubbing and lightfast yellow braanea 'föneip colors. Example 393 0.1 mole of the copper compound of the formula HO sf 30840, \ ® N s N - ## @ # a NM: b4 C-N3 - G - O Soawa been in 3000 parts by volume Vasaer dissolved at pE 6 and stirred at a temperature of approx. 60 ° G with 24 parts by weight (0.111o1) 2-llothylsulfonyl- 4,5-dichloro-6-®®thyl-pyriaidin combined. That isth is stirred until the condensation has ended, the Parb- Stiffly deposited and isolated by adding some sodium chloride. The residue is washed with acetone and at room temperature dried under reduced pressure. A dark powder is obtained daa dissolves in water with green color and cotton after the Procedures given in Examples 327-329 in green Tones colors. Cotton fabric is impregnated with a solution at 20 - 25 ° C, the per liter of liquor 25 g of the above Parbstofls and 0.5; one `: chenoge @ en Netamittels (see e.g. a polyethylated oleyl Contains 15 urea and 20 g sodium carbonate. At- the fabric: wipe two gumiwalson on one ] Fozeitigh :: ehalt of approx. 100% squeezed off. After the interim drying at 50 - 600C is heated to 1400C for 10 minutes and the The dye obtained in this way is rinsed thoroughly with hot water and 20 Minutes of boiling treated with a solution containing 5 g per liter Contains Narseiller soap and 2 g of soda. After rinsing and drying receives a green] coloration of good Na®, friction and Luminosity. Also in one of the others, in Examples 327-329, 344 and 356 hesehriebonon '] dyeing or printing processes are obtained on Cellulose materials clear green from good Bchabeiten. of example 394 0.1 Get the paste of the aainoaso compound of the formula SDSH. see p HsN / N_ N t / Ho, s 0_ cU._ ö H by coupling the Diasoniuaverbiadung from 6-Aeetaaine-2-amino- naphthalene-t, 8-disulfonic acid with 2-ozynaphthalene-3,6-disulfoic acid "Saponification and and conversion of the mono-absorber bond into the Zupterkomplez is dissolved in 2000 parts by volume of water at pH 6.5 and with 29 parts by weight of 2,4-bis-oethylsulfonyl-5-chloro-6-ethyl pyrimidine combined. The keaktionageaiseh will be atö0 - Stirred 650C until the condensation has ended, the pH.der The reaction solution is kept at 7-7.5 by adding soda. After the reaction has ended, the dye is salsed out, aaoliert and dried in vacuum. The dried dye is a dark powder that turns dissolves in water with purple color and cotton in the presence of Alkali stains in bluish violet tones. Example 395 The väßrise solution of 0.1 mol of the Küpferkompäezes formula HOsS 0 Gu o HsN S®, @ 1 30jH bergestelYt according to the German patent specification 1 ß61 t60 bsw. 1 085 988, is used in the usual way with 24 parts by weight 2-iethylsulfon, Trl-495-dichloro-6-ethyl-pyrimidine for the reaction brought. Mm keeps the pE at 7 - 7.5 by adding soda and after the reaction has ended, the dye is isolated by AurESalsen. When dry, it is a dark powder that is dissolves in water with a violet color. lanrvollgevebe viril in light Colored as a blue shade of violet. Example 396 2795 parts of 2-sethylamino-5-hwdroay-naphthalene-7-sulfone- acidic sodium is dissolved in 150 parts of water, with 29 parts 2,4-bis-methylsulfone W l-5-ehlor-6-metbyl-pjrrimidie added and at 50 - 550C with daily blunting of the nethanesulfinsiusi formed with a total of 34 oolus parts of 16% goda solution to pH 6 - 7 touched. After a short time the Aojrliernag is over 6 and no longer changes. 30 parts of sodium bicarbonate are then added and the mixture is charged at 200.degree iamsrbefib if 15 minutes the diasuspenteon from 34 parts of the di- natriumealaes der 2-AÜnoaaphthalin-l., @ - disulf®nanare In 300 parts Dripping water. The orange reactant color that was created immediately Substance of the formula '' NQ 603b4e OH r N = N g @ CW @ r @ la® I 1 @ 1 after stirring for one hour by adding 80 parts of cooking salt completely separated, filtered off, with dilute 1Coc @@ ials- Washed solution and dried at 350C in vacuo. He colors Cellulose maierial ien according to the above , named process in red atichigen ilrangetbiien of very good wet fastness and good chlorine persistence . If you use in this example instead of 29 weight share 2,4-bis-ethylsulfonyl-5-chloro-6-n-ethyl-pyrimidine equivalents Bending of 2-rethylaulfonyl-4,5-dichloro-6-methyl-pyrimidine, so he if you hold an orange-colored active dye, the color of which is exisehes Behavior of the ilmsetauageproduct of bis-methylaulfonyldorirates is equivalent to. In an analogous way, one obtains the in column 3 by aylation the following table listed aminonaphtholsulfonic acids aft 2,4-Bia-methylsulfonyl-5-chloro-6-methyl-pyrimidine or 2-llethyl- aulfonyl-4,5-dichloro-6-methyl-pyrimidine of the kcylarino- naphtolsulfonräuren with the Diaaokoap®nenton mentioned in column 2 orange to red reactive dyes. Shark Diasohoaponente Aainonaphtholaulfonic Acid Hue on apiel cotton He, 397 2-azinonaphthalene-2-ethylamino-5-hydroxy-orange 1,7-diaulfonic acid - naphthalene-7-aulfona acid 398 2- (DI (hydroxyethylasino) - 5-hydrocynaphthalene-7- sulfonic acid 399 2-amino-5-hydroxynaplstha- " lin-7-aulfona acid 400 2-amino-5-hydroxynaphtha- " lin-1,7-disulfona acid 401 "2-Auino-8-hydrozynaphtha = Scharlaeh lin-6-sulfona acid 402 "2-Aaino-8-hydroxynaphtha-" lin-3,6-disulfous acid 403 @ 1, -inonaphthalene-2-methylamino-5-hydroxy-orange 1,0-diaulphonic acid naphthalene-7-aulphonic acid 404 2-ethyl amino-5-hyd rozy- " naphthalene-7-sulfonic acid 405 2- (D- ) hydroxyethylamino) - " 5-hydrocynaphthalene-7- sulfonic acid 406 "2-Asino-5-hydrozynaphtha-" lin-7-sulfonic acid 407 "2-Aaino-5-hydroxynaphtha-" lin-1,7-diaulfonic acid 408 2-aminonaphthaiin- 2- amino-8-hydrosynaphtha- scarlet laugh 1,5 -diaulfonic acid lin-6-sulfonic acid 409 " 2-Amino-8-hydrozynaphthd- " lin-3,6-diaulfonic acid 410 2-aminonaphthalene-L1-amino-5-hydrozynaphtha-orange 1,5,7-trisulfonic acid / lin-7-sulfonic acid 411 2-methyladino-5-hydroxy " naptithalin-7-sulfonic acid 412 2-Amino-8-hydrozynaphtha-scarlet fever lin-6-sulfonic acid 413 2-aminobensul- 2- @ ethylasino-5-hydroxy-orange sulfonic acid naphthalene-7-sulfonic acid 414 2- (B-hydroxyethylamino) - " 5-hydroxynapitthalin-7- sulfonic acid 415 2-Amino-8-hydroxynaphtha-scarlet fever 1in-6-aulfous acid 416 "2-Amino-8-hydroxynaphtha- " lin-3,6-diaulfonic acid 41'j "2-aoino-5-hydrozynaphtha-orange lin-1,7-diaulfonic acid 418 2-Aeninonaphtlialin-1-Amino-8-hydroxynaphtha- bluish tints 1-aulfonic acid 3,6-diaulfoic acid red 419 "1-Amino-8-hydrozynaphtha- " _ lin-4,6-disulfunaic acid 420 2-aeinonaphthalene- 1-amino-8-hydrozynaphtha- " 1,5-diaulfona acid lin-3,6-disulfonic acid 421 1-amino-8-hydrozynaphtha- ' lin-4,6-dinulfona acid 422 2-Vaiaonaphthalin-1-Amine-8-hydrozynaphtba- blanstichiges 1, i-disulfonic acid lin-6-aulfona acid bot . 423 2-Aatineuaphthalin- 1-Asine-8-hydrozynaphtha- " 1,7-diaulfow`acid lin-3,6-diaulfonic acid "1-Aaino-8 = hydrozynaphtha-" lin-4,6-däsalfonic acid 424 1-imino-8-hydrozynaphtha- " lin-6-sulfonic acid 425 2-Aminenaphthalin-ii-Anino-8-hydrozyaaphtba- " 1, S, 7-triaulfenaic acid lin-6-aulphonic acid 426 1- Amine -4-chlorbea 1-Aaino-8-hydrozynaphtha- " sol-2-sulfona acid lin-3,6-d.isulfonic acid 427 1-Viso-2-Mothozy- -Aaeino-8-hydrozynaphtha- " beasol-S-sulfonic acid lin-3,6-disulfonic acid 428 1 latino-bensol-2- 1-amino-8-hydrozynaphtha- " acetic acid-4-sul-lin-3,6-diaulphonaic acid f ensum 429 1- Amines -4-aeotyl- " Violet minehensol-2-sulfe'- acid 430 " 1-amine e-8-hydrozynaphtha blauatiehises lin-4,6-disulfonic acid bot Example 431 56.8 parts of the diasotated im- A oneo-3- t acetylaninobensol-6-sulfonic acid acid in acetic acid modiur and anacäliel@ende.eikalische or acid hydrolysis of the acetylamino group erbeltened'Diaminoasofarb- Substance are dissolved in 450 parts of water at PH 7. After adding -kyn 24.0 parts of 2-ltethylaulf'ony1-4,5-dichloro-6-methyl-pyrimidine is constantly dulling the released hydrochloric acid with Soda solution stirred at pH 7-7.5 at 6t3 ° 0 for about one hour. After loading When the asylum has ended, the resulting formula will be used as a base 3p3Na r1Hs G11 @ 0 @@ N - M. @ K wM T Soss alienated, filtered off, again in 4000 parts of water at 50.degree dissolved, filtered and removed from the filtrate by adding 400 parts High eel deposited in a completely pure form. The dye will like usual dried at 350C in vacuo. It stains cellulose aatrials after one of the above-mentioned processes in real yellowish tones Shades of orange. Example 432 For the neutral solution of 60 parts of the Trinatri m asals den therefor coupling of diasotated 2-amiaonaphtbalin-3,6,8-tri- salfeaeüare with 3-Aeetylaniao-anilia in an acetic acid medium Halt & n.en Aainoaso coloring agent in 500 parts of water is added 24 Part 2-Nethylaul! Onyl-4,5-dichloro-6-methyl-pyrimidine and stir a Hour at 6fjoC, with constant addition of caustic soda a pH of 7-7.5 is maintained. The partially Aeylation product precipitated is at pH 7 by adding 100 Share Kochaals completely separated and filtered off. For cleaning the reactive dye thus obtained can again be divided into 2500 parts Dissolved water at 300C, clarified and then sausing it 350 parts of the filtrate was previously separated out. Of the Color part has the formula @ 0t `w ' a W = N N e N ec , @ a @ ßs so, Ns. N # -cocH, cl and represents. aseh the filter biorea, drying at 350C and grinding yellow powder which easily dissolves in water with a yellow color eel cellulose fibers using one of the above-mentioned dyeing processes. in the presence of acid-binding agents in very real rotatiehig yellow Tones colors. Real yellow also appear on wool and polyamide fibers Stains received. Similar dyes can be obtained if one uses as above drives, but instead of the 60 parts t, -emino-2'-acetylamino-phbayl- Corresponding to sodium (1 ') -aro-aaphthalia- (2) -3,6,8-trisulfoic acid Amounts of the amino compounds given in column 2 and the coupling components specified in column 3 in the usual way: obtained by diasotization and coupling in esoigsaurea medium Aminoasofarbatoffe uses andwith 2-Nethylsilfonyl-4,5-diahlor-6-methyl-pyrimidine acylated. In the case of diazo component, wet coupling component, color shade au! play tree full Mr, 433 2-aminonaphthalene- 1-asino-3-methyl-6-methoay- strong red- 1,5-disulfona acid beasol # stichigss - yellow 434 1-Amiao-3-methylbeasol yellow 435 1- "inonaphthalene-6-rotatiebises sullona acid yellow 436 1-Amino-3-aeetylamino- bensol 437 3-Asiaophenylharastofi '" 438 1-Amino-3-hydrocyacetyl- - - ariaobenzene 439 2-Amiaonaphthalin- 1-Amino-3-methyl-6-methosy- strongly rotati- 5,7-disulfonic acid benzene - like yellow 440 1-Aminonaphthaiin-7-sallon-rotatichigea acid yellow 441 1-Amino-3-acetllaminobensol 442 " 3-aminophenyl urea " 443 1-imi »-3-hydrozyaoetyl- amino-bensol 444 1-lniaoaaphthaläa- 1-laino -; - neth, l-6.-meth- strongly rotati- 3,7-dianltonsäore osrbessol chiges yellow 445 "1-Anino-3-Nothylbensol rotstichisos yellow 446 1-A, inaaapbthalin-1-Aaiaoaaphthalin-6-aulton-rotatichisea 3,7-diaultoasäua acid yellow 447 2-lnino: aphthalia # - 1-asino-3-nothylbonsol " 3,6-lisaltasaäs: as ~ 448 " 1-asino-3-nethyl-6-aetbosr- strong red- bensol stuffy yellow 449 '1-Arino -; - acetyl «inorotatichisea beasol yellow 450 "3-Aninopheaylharastott " 451 "1-Aaino-3-hydro: yacetyl- '" minobensol 452 "! -Lrisoaaphthalia-6-sultoa-" acid 453 Z-lniaoaspkßht, ian- 1 - wino -; - acetylaniaobeasol " 6,8-äisslfosaä @ ass @ 454 "1-Aniao-2-aetbosynaphthalin- strongly rotati- . 6-tone yellow 455 '1-Anäaonaphthalin-6-Sul-rotatichi4ea teaaäeare yellow 456 2-laisonsphthalia- 1-aaiaonaphtbalin-6-aulton- yellow b, 8-aisrt-iteasaic acid "1-Aniaoaaphtbalia-7-anltoanärro " 45 7 @ -45 $ 2-Aainonaphthalin- 1- Amine -ß-metho: Innaphthalia-_ strongly rotsti- t, 8-dianlionic acid 6-aul? onshurt chic yellow 459 "1-methylamino-3-netllbtasol yellow 460 2-isinonaphthalene-1-ethylamine-3-rtthylbeneol yellow t, 8-disulfonic acid _ 461 N-lhthylani l-ia " 462 "N-Ethylaailin" 463 "N- (0-hydrolyithyl) -aailin" 464 N-8utylaniline " 465 Z-aminonaphthalene aniline rotstiohäges 3,6,8-trisullona acid yellow 46s i-Amiap-3-methylbtasel 467 3-aaiaophonyl urea " 46 lbs 3 " 1-amino-3-hydroayacttyl- minobeaso l 469 " 1-amino-3-acetylamiao-6- gtlbatichi- sethozybtnsol ges orange 470 1-Anino-3-acetylmino-6- reddish methylbensol yellow 471 1-A @ sino-3-s, tthan-salfonyi- " aainobensol 472 2,5-Diatthoiyanilin Gelbatichi- full orange 473 3-ethyl-6-netho = yaailin 474 N-methylaniline rototiehiges yellow 475 2-aminonaphthalene-N-ethylanilir rotstichises 3.6,8-trisulfonic acid yellow 476 9 N-butylan oil An " 477 " N- ( D-Myairosyäthyl ) -ani 1 in 4'78 3- (N-Ethylamin® ) -toluene " 479 "2-aminotoluene " 480 "1-Amino-2,5-dimethylbens®1 very rotst.Yellow 481 "1- A siao-2-methozybensol strongly rotsti- chiges yellow 482 ° 1-Amino-3-methylbene sol reddish tinge yellow 483 " 1-ethylamino-3-methocybene sol " 484 1-aminonaphthalene-6-sulfonic acid " 485 ° 1-aminonaphthalene-7-sulfonic acid " 486 a-1sliphthalin- 1-emino-3-methylbenzol " 4 , 6, 8-tri sulphonic acid 487 " 488 1..1mi®eaaphthalin- 1-Amin @ u-3ethylbensl yellow 2, b, 7-triaulfonic acid 489 w 1-AAinon.% Phthail in®6-sulfonic acid '° 490 b-Witrek I®smintsti ®mc @ o®3 @ aylaminc @, @ s @ 1 rütetichi = es ben®2,2e-dieu2foaic acid @ s yellow 49 @ - Ai @@ e @ h @@ ®ff " 492 "1-Amimmo-3®hrozyacetylamino-" bensol 493 4-Nitro-4-aniao- N-Mothylaniline rotatiehiiea atilben-2.2l-disul-yellow ionic acid 494 " N-Ethylaniline " 495 "N-butylanilaniline " 496 N- (ß-Hydrocythyl) aniline ° ' 43'T 1- (N-Ethylasino) -3-rothylbene " 498 aniline-2,5-disul- 1-aminonaphthslin-6-aulion- " fonaäure acid 499 1-aminonaphthalene-7-sulionaane " 500 1-Amino-3-ethylbene sol yellow 501 1-amino-3-acetylaninobensol " 502 1-Anino-2-mothozy- 5- Bothyl-rototichigea bensol yellow 50-5 ' 1-Asrino-2, 5-d ine thszybenmel 504 Ailia, -2, -äiaor. @. is ,, @ - 2-ethogy-5-sethyrl- ® acid br "aaul Example 505 6'j? Eile of the dye of the formula (produced by coupling diasotated 1-Hydroz'-2-amino- beasol-4,6-disaalfonic acid on 2-amino-8-hydro = ynaphthalene-6-sul- fonsäuro and haplerang of the ax dye obtained) are in 700 parts of water dissolved neutrally. 24 parts of 2-methylsulfonyl- 4,5-dichloro-6-methyl-pyricnidine is added and the mixture is stirred at 60-65 ° C under constant "Abet-pfen the released yours with soda Lüeung to PH 7-T.5, until no free amino group is very detectable is. The dntstaandee: s # reactive dye is the formula .xa. @. L. _ @ 0 tas @ c4. @ NH @ s tN; C1 is ansgesslsea, filtered, washed and dried at 30 - 400C overall troehaet. He stains according to one of the methods given above Collnle® materials in very real ruby tones. Dyes with similar properties are obtained analogously to working method described above from the Zapferkomplexa from the Diaso and amok components listed in the table gesterlltea Asotarbeteffe a Nra Diasokoapomente coupling component hue on cotton 50E3 1-Hydr®xy-2-aaino-2-methylaaino-5-hydroxy-ruby bensol-4-sulfonic acid naphthalene-7-sulfonic acid k 2-r @ thyl-aaino-5-hydzoxyv " naphthalene in - 7-sulf cin® acid `@Uf:" 2 - (1; -Hydroxyäthylamiao) - " 5RhYdroxYnaphthalene-7-aulfone- acid `_, üc # K 2-, Aaino-8-hyürüxynaphthal in-" 3.66®dieulfonic® acid 51C: 1-hydroxy-2-asino- 2-amino-j-hydrozynaphthalene- bensol-4,6-disulfonic -1; 7-diaulfonic acid acid 511 "@@ - @. @ A__o°8®hyd.roxy@aphthülaxa- " I # I;: äüR1111n- 7aaul fonsäure naphthalene ° 7-sulfonic acid . @ 1 « 2 - ('ß - Hydroxyäthylaaino) -5-hy- ' ° droxynxphthal in-7-aul fonaäure a 51L 1-Hydroxy-2-amino-i-IiFio-8 = hydrGxynaphthal in violet bensol®4,6-diaulfonic 3, c3 - diaulfonic acid ®äuro 51 @a "1-lueino-8-hydrozynaphthalin- " 4,6-disulfonic acid 517 1-lydsaay-l-miae- 1-Mine-8-hydrozyaapbthalis- Violet iessal-s-sulfosa @ aso 3,6-dia @ tllonsänro 51f; '1-Asino-8-hydrozynaphthalene- " 4,6 = disulfonic acid 51c. 1-Hydrozy-2-saino-4- 1-Arino-8-hydrozynaphthalene bluust. aeotylamineheasol-6- 3,6-diaulfoasäare violet snifeuä: re 52G I- @ i - @ - srine - @ - 1-Äthosy-i-hydrozynapltthalin _, aeoty1miaelonsel-6- 3,6-diaelfeasl e ro snl f onsäare (4-stäadiie lcotylaai »8group then saponified) 521 "1-Arino-8-hydrocynaphthalene Blue 2,4-diaulfonaic acid h22 "1-Arino-8-hydrozynaphthalene- " 2,4,6-triaulfonic acid 1-Hydrozy-2-amino-1-amino-8-hydrozynaphthalene blue 6-acetylaainobensol-2,4-disulfonic acid 4-sulfonic acid (6-part Acetyla = inodruppo saponified) 1-Arino-2-hydrozy-6- nitronaphthalene-4- sulfona acid (6-position nitro group then reduced to -NH2) 525 1-Aainos2-hydrozy-6- 1-Amino-8-hydrozynaphthalene- " nitronaphthalene-4, 2,4,6-triaulfonic acid sulfonic acid (6-position nitro group then reduced to -NH2) 526 1-Hydrozy-2-aaino-6- " acotylaainobensol-4- aulionic acid (6-atändide #cotylminodruppe saponified) example Proceed as indicated in Example 55b, but connect that diasoped intermediate product containing reactant groups in soda caustic medium instead of 47 parts of the NatriRUnealsen of 1- Bensoylamino-8-hydrozynaphthalene-3,6 = disulfonic acid with 40 parts the sodium salt of 1-acetylamino-8-hydrozynaphthalene-3,6-di- eulfonic acid and isolates the dye formed - the formal in the manner indicated in Example 30. Soluble in water Dyestuff colors cellulose materials according to the Klotz-Damp- bsw. Klotz -Thermofizier-process (at 140 ° C) in whitenable, naB-, rubbing and lightfast bluish red tones. Example 92 '. The solution of 19.5 parts of the sodium as the 1-amino benzene-4-sulfonic acid and 6.9 parts of sodium nitrite in 200 parts Water is in a mixture of 100 parts of ice and 28 parts by volume conc. Let in hydrochloric acid; then half an hour stirred at 0-100C, and then excess nitrous Acid removed. Add to the slide suspension thus obtained 0 - 10C the cooled down wnd thereby partially crystallized solution of 26.2 parts of potassium as the 1- in 250 parts hot water and and the starfit acidic coupling mixture flows through at 10 - 200C careful addition from sodium lag, ge on pR b. The clutch is ended quickly; the dmtuoazofarbstotf formed is with 1110 parts Lochaals completely alienated, vacuumed, washed and again aelögt in 500 parts of water at 100C and pH 6-7. The wä8ripe Lusuna will sit 29.0 parts of 2,4-3is # methylsulfonyl-5-chlax 6-methyl-pyriuidin added and with a loud always: the free wordeadm acid with seda solution to pH 7-7.5 a Hour at 55 - 60 ° C. When there is no more aminoaso dye Weiniat is, the partially precipitated reactive dye is dzr persrs3 @tOt Cis Haoss -0- = N NH 93 `G s ° r"' c 1 Feeled with # 0 parts of Kochaals, filtered off and cleaned for cleaning aotbmtla dissolved in 800 parts of warm water. After clarifying the solution wist from the filtrate by adding 80 to 100 parts of cooking enls the pure dye deposited. After filtering, Trocimsa at 35 ° C and Nahleu you get a yellow powder that is Easily dissolves in water with yellow color and the cellulose fibers after one of the above dyeing processes in the presence of sätire- biadesder agent in very good yellow tones, lightfast and chlorine-fast colors. #ieh with Volle and aolysmidfasers become real yellow colorations, obtain. Before aaa as stated above oii # Urt, jade # 1 aa position 40 19.5 Share the sodium alse, the 1-asiobansal-b..eulfonic acid equivalent s Amounts of the Diasokompeaantea listed in the following table Coupled to the 1-amino-naphthalene-8-sulfonic acid is obtained after acylation with 1-methylsulfonrl-4,5-dichlpr-6-methyl-prrimidine also valuable yellow to brown, reactive dyes. Slide component # t t shade ai! Cellulose fiber 1-Aainobensol-2,5-Diaulfoaaäure red needle yellow 2-Asino-naph $ halin-4,8-diaalfonaäura strongly rotatichigen yellow 2-amine-p-naphthalene-5,7-disulfonic acid 2-amino-naphthalene - (, H-disulfonic acid " 2-amino-naphthalene-3, f>, 8-triavlfoneriure " 2-aaino-naphthalene-4,6,8-trisulfonic acid 4-Asino-asobensol-3,4'-disulfonic acid yellowatichigee brown 4-Amino-2-acetylnmicro-arobensol-2 ', 5'-diaulfonic acid orange brown @o, @. ta # D- NH, rotatichigen Brown So, no , @ @ SO @ Well (1-Aminottenzol-2,5-diaulfonic acid acidic to 1-AKino-naphthalene-6-aulfona acid a coupled) Slide component hue on Cellulose fiber rotatichiges brown SO @ NA N = N @ NH: SO @ Well SO'Na Ca. ') (1-Aninoben: ol-2,5-disulfonic acid acidic the technical mixture of 1-aminonaphtha- lin-6- and -7-sulfonic acid coupled) SOiwla violet brown Nn® SOswie @ S (1-Amino-naphthalene-2,5,7-trisulfonic acid acidic to 1-amino-naphthalene-6-sulfone acid coupled) ä0bwo OCHS N = N @ Nm = reddish brown Well cm, 50; N & (1- Amine- naphthalene-2,5,7-trisulfonic acid acidic to 1-amino-Z-nothozy-5-nethyl- bearel coupled) Example 5 When you print cellulose fabric with a printing paste that per kilogram, 30 g of the dye described in Example 18, 100 g Urnatoff, 300 g water, 500 g alginate thickener (60 g sodium alginate per kilogram of thickening), 10 g of soda and 10 g of the sodium contains aalzes of 3-Nibvbenzul-aulfonsüure and which with water 1 kilogram was filled up, then partially dried and- then in a suitable steamer for 30 seconds at 103 to 1150C steams, so you get one after rinsing and boiling soaps strong bluish red print of good NaD, rubbing and light authenticity. example A mixture of the solutions of 65.5 parts each of the chromium 2: 1- Complexes and the cobalt 2: 1 complexes of the dye of the formula in each 400 parts of water, 60 parts of finely powdered 2-methyl- aulfonyl-4,5-dichloro-6-methyl-pyrimidine approx. 2 hours at 60 - stirred while maintaining pH 7 - g. run chrora- tographically no amino acid dye (Co-complex: blue;, Cr-complex blue-green) is more detectable, the resulting mixture becomes the Both reactive dyes are removed with sodium chloride and filtered off and dried. The Parbetoff. Delivers on cellulose materials according to the tlets dyeing process or under pressure in the presence of acid-binding agents Medium strong, very good shade and lightfast Schvar: tones. If one proceeds accordingly, however, the mixture contains chromium 2 1 and cobalt 2 : 1 complexes of the following Aminoasofarbatoff e used, valuable black dyes are also obtained: Diaso component coupling component coupling pH 1-Bydrozy-Z-amino-4- 1-8ydrosy-8-aminö-naphthalin- nitrobensol .3,6-disultonic acid i-Hydsosy-2- @ rmiaa-t @ - 9 nitrenaphtrslia # 7-enl- fonaäure Heyapiel 531 To the central solution of 53.15 parts of the disodium aalsec leswduseh-tuppala of diasotized 1-amino-t-nitrobensol-2- etaltemeünre with 1- (21-chloro-5'-aulfophenyl) -3-methyl-pyrasolon- and subsequent reduction of the nitro group with sodium sulfide received Aminoazofarbatoffs-in 300 parts of water 25.0 parts of 2-Methylaul'fonyl-4,5-aichlor-6-methyl-pyrimidine and stirs the roofingone Hour at 55 - 60oC, whereby the acidic continuously with soda solution to a p11 value . blunts of 45 t. The deposited dye of the formula is filtered off, warm & dissolved in 3000 parts of water at pH 6-7 and from the filtered solution again by adding common salt failed. After filtering off, drying and powders are obtained a yellow, easily water-soluble powder, the Cellulo®enaterialien from a long liquor at 60 ° C or after the Xlotz cold hold process, drive with soda as an acid-binding agent in clear, washing, rubbing and lightfast yellow tones. ' If you proceed as indicated above, but instead of there Amine @ oazo dye used "equivalent amounts of the in the components listed in the following table amino- azo dyes are used, valuable new Iis- actis dyes In the table, the expression "stiffened" means that $ is a the acylamino group contained in the, minoazofarb®toff subsequently has been soapy, while the term "reduced" gnaws that one in the Dfazokorponente contained nitro group after the coupling to Amino group is reduced, whereby the desired wainoasofarb- Fabric trains. At- -Diasokommponente Asokommponente pH the color tone play Kupplun`s- Collu.lose Nr_ mmediumms 532 1-Amino-t-nitro-1- (4'-sulfophenyl @ 5-6 yellow bemmsol-2-sulfommic acid 3-mmethyl-pyrasolone- (4-hour nitro group then reduced) - 533 ". 1- (4'-sulfophenyl) - @ 5 - 6 rotrticb.i`te 3-carboay-pyrazo- . lon- (5) 534 1- (3 ° -sulfophonyl) - 6 - ' yellow 3-ethyl-5-amino pyrasol - 535 i- amines -3-asotyl-. -. 6th ammimal-6- suliomms @ srr (3-et ä- & i4s Asttylminogruppe then saponified) 536 " 1- (8-Hydrozyäthyl) -E5-6 w 3-nothyl-pyrasolone- (5) 537 Z xo1 1- @ ino-3- 1 Hol Üis-PysasolomL5 - 6 acstyl: -asiimmo-bensol- from 4, t1 = bis-hydrasimmo- 6-sslfomm "nre (vor- dibensyl - 2,2'-dsulton- ssitt) acid and Asttessi`- ethyl ester) 538 1 Col 1-Aeino-3-% - (41-sulfophemmyl) -15 6 aestyl-ammiao-bensol- 3-carbocyte-pyrasolon- 6-snltommaäurs (before- (5) asitt) In the case of diazo component, azo component pil of the hue play coupling- on CR1ln- No mediuia loose 539 1-Amino-5-acetyl-1- (4'-sulfopheäyl) - 5 - 6 spits. amino-naphthalene-3,7-3-carboxy-pyrasolon yellow diaulfonic acid (ver (5) soaps) 540 1-Amino-2-methyl-2-acetylamino-5- 7-8 Urenge benzene-4,6-diaulfone- naphthol-7-sulfone- acid acid (saponified) 541 2-Acetylamino-8-7-8 Plot naphthol-6-aulfone- acid (saponified) 542 1-Amino-2-methyl-i-chloro-2-acetyl-7 - B Orange bsnzoi-4,6-dsulfon-amino-5-naphthol- acid 7-aultonic acid (pre- soaps) 543 1-aminobenzene-2- 1-acetylamino-8-hydrozy = sulfonic acid naphthalene-4,6-diaul- 7 - 8 red fonsäure (distributed) 544 2-A, inonaphthalene- 7 - 8 bluish. 3,6-disulfonic acid red 545 2-aminonaphthalene- " 7 - 8 builds. 3,7-diaulfonic acid council 546 2-Amiaonaphthalene- 7-8 blsust. t, 8-dieultonaure red 54`l 2-Aminonaplith®lin-3.6- 9aAcetylamino-B- 7 ® 8 is boiling. dieultonaäure ihydroxynaphthalim- red 3, 6-diaultonaäare (verealtt) Bei- Dia = ekoaepenente Asohosponeate PH of the hue play clutch on cellu- No, hediuass loose 548 2-Aminonaphtbalin- 1-Acetylaaino-8- 7-8 Mous. 4,8-di-sulfonic acid hydrozynaphthalene red. 3,6-disulfonic acid (®ers e if t ) 549 1-Asino-b-nethozy- 2- (N-Acstyl-N-®ethyl- 7-8 self. bensol-2-sulfonic acid asino) -5-hydrozy- Not asPhthalin-7-sulf®n-- acid (saponified) . 550 " 2- (N-Acatyl-N-BethYl- 7-8 Bot aai no) -8-hyd ro zy- naphthalene-6-aulfone- acid (saponified) 51 1-IVrinebensol-2- 7 - 8 sulfic acid 55? i.e. Amineieaaol-3- "' ? - 8 sulf * NaäupQ 553 g @@ ine @ e @@ ® @ 7 ._ gw ® @ lferesä @@ c 54 1-amine "-" ethyl [ ° 7-8 iseaaal®2®ßaslfens @ nre 555 2- (N-Aeetyl-N-Bothyl- 7-8 Bot hs®aa @ la6ƒ @ mlfanehuae arsino) -8 = bxdrar @ elasphths- ' liu-6-aulfon-lice (eer- sdi @ ft 556 2-acetyl »ino-8 7 - 8 bydresynaphthal in- 6-sulfonic acid (ver aeift) At- Diazoic®mposente #aoicomponente PH of the shade s: piz-i - coupling * - on Celln- Bre medaume loose 557 1-amino-2,4-dimetbyl- 2-xcstylamino-8- 7 - 8 Red benaol-6-sulfonic acid hydrosynaghthalene- 3.'6-disulfonic acid (saponified 558 4-Aminoa: abenzml- 1-Amiao-3-acrtyl- 5 - 6 Gellb- 3,4'-disulfonic acid aminobensol brown 55 ° ". L-Amno-3-hydroay- 5 - 6" acetylaminobensol 550 "1-amino-aaphtbalin- 5 - 6-aultonic acid 561 g-amino-naphthalene 5-6 " '-eulfonic acid f52 8 furrows: 2: _sulfophenyl- (1 ') - aso) -8-hydroxynalshtha- a lin_3,6-disulfonic acid Example 563 52.4 part: the disatrine melee der- t- 04 '' -Amiaophenyl-amino) - 2 "-nitro-d.iplenylamn-3,4'-disulfonic acid-verden in 1000 files Wasaer gelÖat and with 30.0 parts of 2,4- $ ia-methylsulfonyl-5-chloro-6-methyl- pyrimidine for one hour at 55-650C. The Dissolving acid - running with soda to a p11 value of 6.5% reduction. : The reactive nitro dye formed the formula is salted out, filtered off, washed and dried. He colors Collulose fibers from a long liquor or according to one of the usual Klotz method in the presence of soda as an acid-binding agent in deep violet brown tones, which are fast to the skin and rubbed. Hei, 564 The neutral solution- of -54.7 parts of the disodium salsa 1-Amino-t- (2'-sethyl-3'-aminophenyl) -amino-anthraquinone-2, SLdi- sulfonic acid in 1000 parts of water is mixed with 24.0 parts of 2-methylaulfonyl 4,5-dichloro-6-methyl-pyrimidin overall one hour at 65 ° C stirs. The hydrochloric acid released is mixed with soda solution continuously on a® pH-Vert. from 6.5 -7.5 blunted: After finished Implementation is the resulting reactive! dye of the formula Q NN = / @ $ Q1 @ slL o MM / '@ : OtCw' hIH - -IN Cl _ Assgesalsen, herbal-filtered, waxed and dried at 30 - 400C. It dyes cellulose materials a very good ns8, rubbing and light eektea clear blue tones. - _ Blue dyes with similar properties are obtained if you proceed as above; but instead of the one mentioned there water-soluble aminoanthraquinone derivative equivalents. amounts of the aminoanthraquinone sulfonic acid derivatives listed below wate with 2-methylsul; 'anvl-4,5-dichloro-6-methyl-pyrimicfin acyliext: At- water-soluble amino-anthraquinone derivative game No. 565 1-Amino-4- (3t_aminophenyl) -amino-anthraquinone-2,5'-di- sulfonic acid 566 1-Amino-4- (2'-cblor-3'-aminophrenyl) -amino-anthraquinone- l.5`-diaulfonaic acid 567 1-Amina-4- (2'-methy1-3'-methylaminophenyl) -smino-anthra- quinone-2,5'-disulfonic acid 56 £ 3 1-Amän®-4- (4'-aminophenyl) -amino-antbrachinon-2e6.3'-trf- sulfona acid 5-61 1-Amino-4- (3'-aminoplaenyl) -amino-anthraquinone-2,6,4'-tri- sulionic acid 570 1-Amino-4- (4`-aminop ) senyl) -amino-anthraquinop-2,5,3'-tri- eulfonic acid . 571 1 # -Amino-4 -_ (3'-amivophenyl) -aaino-anthraquinone-2,5,4'-tri- sulfonic acid 572. Mixture sue -Ami @ no - & -. (3 °, .., aaenophenyb) -a @ rinn-amthratela®ea- 2,41,5- and 2,41,8-trisulteugic acid distant ##,. # e mx R #; E, 't ..: x # e'2' N 5C50: @ sc # ät »r's; äx 573 1-3min-% a @ ISr @ .A` @ 2 @ 1x? £ @ ''# t @: `@@ J'0 2-amllo®sisure , __ _ _ 574 1-A @ aino-4 - (@ S -re thy l dninoplrfnyl) -anino-aathraquinone-2- aulionic acid 575 1-Amino-4- (3'-rethylaninophenyl) -amino-anthraquinone-2- anlfonic acid 576 1-Arino-4- (2 ° -metlsylaminophenyl) -amino-aathraquinone-2- sulfonic acid 577 1-Arino-4- (7`-amino-naphthyl 12j) -amino-anthraquinone- 2-sulionic acid 578 Äondenaationsprodulet of 1 hol of cyanuric chloride with 1 hol 1,4-diarino-anthraquinone-2-aulfona acid, 1 pint of aniline-2,5- diaulionic acid and 1 pint of ethylene diasin (one side), after acylation with 2,4-His-methylsulfonyl-5-chloro 6-methyl-pyrimidine is a violet reactive dye. Example 579 A Läomg ®on 107 g of a cliché made up of equal solar components tn @ 3as @ lrthsalc @ c @@ i @@@@ i @ c @ 1 @? @ tt @ 'a' @@@ a @ (3,3 ° . @ °) -aano- (r-awino-p = emlfa »t W l) marid and Zupferphlzhaloe'anine-trisulionic acid- (3,3e, 3") - di- ( z -ss i ne-p-anliopbonyl) - "id becomes 1.3 liters and plt-7 a;: - represents; at 50 - 55cC 50 parts of 2,4-8ie-metbvlsulfonyl-5-chloro- 6-aethal-pyriaidin entered. With stirring, the temperature is per Hour increased by 5 ° C and finally several hours: at 65 - 7000C 1e1. At the same time , instillation of iroa 3a-N & OD results in a pH of ltva @, `6 @@: Celteabie duol @ eehnittic each rerbetoi '» le. kUi with mind athe ebnem p, # erimdinre-st verseen -is "what a®ite an, consumption de, r @.? tzr tri # ä on the other hand by an amino group fengestelat weei, 'n ._ = _. Utarxt the dye solution can also do something with the specified pH be heated without affecting the 'reactivity of the: color substance is considerably reduced with the Cel7 @ .lo-, e. The Ab- separation before. unreacted 2,4-bis-methylsulf'onyl-5-chloro-6-methyl- pyrimidine and the resulting saponification products by filtering or im_Separator.- By entering 150 g Table salt per liter of dye solution is used as the falls. It is sucked off and in vacuum or at Neruaandruc & bei dried about 300C. This gives 195-200 g Rohfarbstoff-, the still contains about 3.0; G Kochaals. By stirring the Roäfarbatoffa with 250 a1 of water and again. The table salt can going to be removed. The dye dyes cellulose materials according to the padding Thera, ofi-ornamental process. at 1400C and after the, Klotz -Diirpf-Veriahren in 'n08, rubbing and lightfast turquoise tones: The Farbatofigenisch used as starting material can naeb per se known * procedures are obtained, a.- H. by one aqueous suspension of sulfonic acid group-free copper phthalo- cyanine triaulphonic acid chloride at 0 - 20®C 3 M01 2,4-diaminobensol- aulloneiure at a pHI of about 6.5 and at the same time with 3 Mul Pyridine the oxygenation the above mixture 'the PC sulfonamides are created. A similar product is obtained; if you are a starting point ice mixture used, the components mentioned in ) i01-, 1 ' contains a ratio of 4 : 1 . This mixture will be the same äupferphthalocyanin-trisulfonsäure-chloride and 2 moles of 2,4-diamino-. benzenesulfonic acid obtained by the same procedure. Instead of the starting materials mentioned, it is also possible to use such which contain nickel instead of copper as the central atom or from copper phthaloeyanine triaulfonic acid chloride (4,4 ', 4 ".) or to Phthalocyaain-tetrasulfonsäure-Chloriden- (3,4 ', 4 "94801) or - (4,4 ', 4 ", 4"') or using other arylenediamine sulfonic acids, Brie toluene-diamine- (2,4) -sulfonic acid = (5); 4,4'- Diamino-dibeazyl-disulfonic acid- (2.2 #), naphthylenediamia- (1; 5) - disultonic acid - (»3.7) were produced -. Such products and theirs Manufacture are described many times in the patent literature. Your implementation with 2,4-bis-methylsulfony1-5_-chloro-6-methyl-pyrimidine or 2-methylsulfonyl-4,5-dichloro-6-methyl - pyrim-idin can always be used in the n. done in the same way. This also applies to the sales of: s-2-Metriylsulf * onyl-4,5-dichloro-6- methyl-pyrimidines with the reactive dyes leading to green Zupfer- and nickel-phthalocyanine intermediate products as z. B, by pelysulfochlorination of tetra- (3,3 ', 3 ", 3"' -) - (p-tolyl- mercapto) copper phthalocyanine with chlorosulfonic acid, condensation from 1 to 2 sulfochloride groups per molecule with 1,3-phenylene- diamine-4-sulfonic acid or 1,4-plsenylenediamine-3-sulfonic acid and soaping of the remaining sulfocrlaride groups are available; even those containing single or mixed aaiao and sulfo groups > rylation and alkylation products of tri- and tetramereapto- copper (or nickel.) phthaloeyanin "can be carried out in an analogous manner Acylation of their amino group with _2,4-bis-methylsulfony1-5-chloro-6- methyl-pyrimidine - in valuable green reactive dyesbe transferred. example 580If, according to the information provided by the B.eiapielr344verffahren,: however the received Ink pot intermediatenot with the Diazo * er bond the end 17.5 parts of 2-, iminobenzenesulfonic acidbut with the Diazo connection from 20.8 parts 3 = chloroaniline-6-sulfona acidin Presence of 12 parts of soda in one Ead-pHfrom 7 clutch,so you get one Reactive dyethe formula with the cellulose materials from a long liquor at 400C or after one of the padding or printing compressions customary for reactive dyes drive with soda as an acid-binding agent-in wet-fast, brilliant Red tones can be colored or printed. In an analogous manner, one obtains from the table below listed coupling components by acylation of their Awino- group with 2-Methylsulf'.ony1-4,5-dichloro-6-methyl-pyrimidine and Coupling of the resulting intermediate dye products with the other given diazo components valuable reactive dye, with which cellulose minerals in the listed shades - before: ugs- weis® in the presence of soda - be colored or printed know: Hei- Diasokomponente coupling component coupling®- color tone ' epial PH No. 581 1- A mino-4-methosy- 1-Arino-8-hydroay- 7-8 violet bensol-6-aulionic acid naphthalene-3,6-di- as' L, sulfona acid 582 "1-Asino-8-hydrosy = 7 = 8 red-tinged naphthalene-4,6-diene violet sulfonic acid 583 2-amino-5-hydrozy- - 7 scarlet fever naphtha-1,7-di- aulionic acid 584 1-Asiao-5-chloro-ben- 7 Orange sol-2-ealtonic acid 585 1-Aain®bensol- '° 7 3-aullonic acid 586 1-aminobensol- `@ 7 4-mm @ l @ oa @ s @ äu @ e 5.87 2-amine-8-hydroacy- 7-e scarlet naphthalene-3,6-di- - - sulfona acid 588 4-Ameinobentoe- 1-Aamino-8-hydrö-zy- 7-8 Bot acid- (B-aultonaphthalene-3,6-di- ethyl) -aaid sulfonic acid. 589 ' 1- * ino-4-aulfo-- 7 - 8 ' violet acetyleaino-ben- sol-6-sulfonic acid 590 1-Aeino-3-aulto- 2-Aaino-5-hydro: y- 7 Orange - aeet'luino-bensol- naphthalene-1,7-di- 6-aultonic acid -. sulfonic acid 591 1-Amino-4-sulffo-2-amino-5-hydrcay- 7-scarlet acetylemiuo-benzene naphthalene-1,7-disulphonic acid 592 1-Asinobenzal-2 "4- 1- (2'-Hetliyl-j'- 6 yellow diaulfonic acid amino-5'-sulfoPhenyl) -3-methyl-pyrazolon- (5) 59'3 2-amines-naphthalene- 6thyellow 4th , $ - di $ u1 fons: äur.e example 594 If one proceeds according to the instructions in the example j56, however, q that from: 1,5-diaminobenznT-b-alalfonic acid and 2-methylsulforty1-4,5-dich? or- 6-methyl-pyrimidine equivalent to Ltehe @ arbstof-f intermediate product after sliding at 100C and pH 7.5 to 6.5 with the solution of 40.5 parts of Diiiatriumsalses the 2-sulfoacetylsaino-5- Coupling hydroxy-aaphthal-in-7-sulfonic acid, a reaction is obtained dye of the formula - of the cell reading materials according to the usual application procedures with. Soda as an acid-binding agent colors in real uranium tones. . example 595 If span proceeds as indicated in Example 531, but instead of of the Aainoazo dye used there 5;, 15 parts of the Dinatri- nnsals®s of the coupling of diazotized 1-amino-4-nitrobenzene 2-sulfonic acidwith 1- (2'-Chl.or-5'-eulfophenyl) -3-methyl-pyrazolone- (5) and subsequentReduction of Nitro groupwith sodium eulfide obtained aminoezo dye with the 2,4-bis-methylsulfonyl-5-chloro-6-ethyl-py acylated rimidine,so one also obtains a valuable reactive dye, with which cellulose materials according to the usual dyeing and printing processes in real yellow tones can be printed: Similar reactive dyes are obtained if instead of the above The named A®inoaso dye is one of the following - Aminoazofarbatoffe built up components listed in the table with 2-Nsthylaulfonyl-4,5-dichloro-6-methyl-pyrimidine acylated Hei .. Diaao component Azo component hue game No s 596 1-Amino-4-nitro-1- (2'-ethyl-41-su.lfo-yellow bensol-2-sulfon-phenyl) -3-soethyl-pyra- acid (reduced) zolon- (5) 597 1- (21.5 ° -Dieulfophenyli- yellow 3-saethyl-pyrazolone- (5) 598 1- (2 # -Methyl-4'-aulfo yellow 61-chlorophthalyl) -3_sethyl- . pyrasolon- (5) 599 1-Amino-4_nitro- 1- (21 @ 5a-dichloro-4 # - yellow benzene-2-sul on-suliophenyl ) -3-'ethyl- acid (reduced) pyrßsolon- (5) 600 1-Amino-3-ecetylaarino-1- (2'-methyl-4'-sulio-green-tichiges benzene-6-sulfonic acid phenyl) -3-methyl-pyraso-yellow (saponified) ion- (5) .601 1- (4 # -9ulfophenyl ) -3-; greenish tinge methyl_pyrasolone- (5) yellow 602 M 1- (2R-methyl-4R-sullo- , * phenyl) -3-earbozy-pyrazd- lon- (5) 603 1 .. ( 2 #. @ Gh l cr-4 -eul! O- phenyl) -3-carbozypyraso- on- (5) example 58 parts of the Dyes theformula (produced by coupling diazoterter B-hydroxy-2- »ino-4- chlorobenzene-5-sulionic acid on 2-methyl « ino-B-hydroxy-naphthalene- 6 = sulphurous acid and coppering of the obtained azofsrbeto fe) dissolved neutrally in 7U0 file water. You give 2490 parts fine powdered 2-methylnulfonyl-4,5-dichloro-6-methyl-pyrimidine was added and stirs at 60 -50G down- ctIindägen dulling the lrcWer- dendea Salsaure with Sodalbeung äf PH '@ -, 5 to no free Antaegssppe ® is very detectable. The educated "Rsahtiwiarbatoii the formula a - CU - = Hs @ d @ stws d = .1J 1 @ M @cN Nil® '' @ C 1 3, G is «unsalted, filtered off, washed and at: 3ƒ .- 400C kick k » t. He stains, using one of the methods given above Cellale materials have eight violet tones. Dyes with similar properties receive .a » analogously the * am described working method aas den - through simple, en hplating or oxidizing lipid obtained - then use the dibzos listed in the following table and prepared mono and deaso arbors: Sei- Diasoko®penente AsokoMponente coupling color play PR 605 1-S'droar-p®amiaao- 2-Amano-8-hydrosy- 10 - red. b..ohlerbensol-5- "naphthalene-3,6- violet sulgemsänre dlaullonsüure 606 1-Amino-S-hydrozy- 1 0 embarrassing. naphtbalin- $ 3 .-- Violet disulgoaassure 607 2-Amino-uaphthalene-2-Hydroay-6-aat- 8 - 9 'rotst. 4,6,8-trisulionic acid ylaaimm®-®aphtha- blue (oxidizing; ekupf * rt), 1in-4-sultoasbure ( vlrteift) 608 1-Aaino-2-hydroiy- 1-ltydrozy = B-eth- _ 10 blue 6-nitronaphthalene-oxy-naphtbalin- 4-sulfonic acid (re 3,6-disultona acid showered ) 609 1-Hydroay-2-amino-2-itydrozy '= 3- «ino-10 red a: ol-i, 6-disulton- naphthalene-3,7- acid dsulfona acid 610 2-tmtno-aaphthaln- B - 9 blue k, 8-di®ulonic acid (oxidizing ao-copper j 611 B- i aonapäthalin- 2-ai'droay-3-aano- 8-9 blue -4,6,8-triaulionic acid naphthaiin-7-auIfon- (oscillating coppered) akurt ` 612 3-Hetho: yt-saiao-6- 2-Hethylaaino-5- 10 marine nothyl-agobenfol-2 ', hydrozynaphthalene blue 4'-dieulfonic acid (ent-7-aulonic acid ethylating copper) 613 w , 2-asino-8-hydrozy- 10 " uaphthalene-3,6-di- sulfonic acid 614 M 2-Asiaio-5-hydrozy- 10 p - nephthslin-1,7-di_ aulffonic acid 615 3-üethosy-4-aaino- 2-Methylaain®-3- 10 marine 6. # a4thyl-aaobensol- hydrozynaphthalene- blue 2 ', 3'-diaulonic acid 7-aulphonic acid (satgothyli rend g * - tups `@_ -. _ 616 3-metho = F-4- »ino-2-amino-8-hydroxy- 10 navy blue 6-neth'1-asobensol- naphthalene-3,6-di- 2 ', 5'-disulfonic acid sulfonic acid (demethylating copper) . 617- "2-amino-5-hydroxy-1.0" naphthalene-1,7-di- - sulfonic acid of example 61e3 If you proceed according to the information in Example 564, however, instead of the 54.7 parts of disodium mentioned there 1-Ilaine-4 - ((2'-weth, l-3'-aainophenyl) -a "ino) -anthraquinone-2,5-di- aalfonic acid 63.5 Divides the trisodium salt of 1-amino-k - ((3'- lainephen'1) -aaino) -anthraquinone-2,4 °, 6 '- (or 2,2', 6 ') - trisul- fensäure, one gets a reactive dye, - the cellu- reading fibers according to one of the usual dyeing processes in very good colors like, clear, red-tinged blue tones. When using equivalent amounts of i-amino-4 (3'-aainoPhonyl- asiino) anthraquinone-2,5,8-triaulfonaic acid is also obtained a valuable Iieaktivfarb® fabric, the cotton in real gray deep blue tones. Betspiel 611; 30.4 parts of 2-amino-8-ozynsphtbalin-3, G-diaulfonic acid neutral dissolved in 300 parts of water, heated auf6Q -65oC and 25 parts of 2,4-bis-methylsulfonyl-5-chloro-6-methyl-pyrimidine-added. In the course of one hour , 4 4 parts 15,961 g of soda solution are added added that the pü value is between -6 -7s5. That, 'Acy- lation product partially fails, An Irish-made Diasoniussa-lslö®uag an®.13.6 parts. p-Asinobensylaulfonaäure is at 0 - 5 ° C in the with 12.5 parts Soda-added suspension was added dropwise to the acylation product. After stirring for five hours at egg bath temperature, nalz auageaalzea, sucked off, with diluted kitchen solution after- washed and dried at 300C in a vacuum drying cabinet. The dye obtained corresponds to the formula If one proceeds as indicated above, but instead of 30.4 parts of 2-amino-8-o: yuaphthalene-3,6-disulfonic acid 30.4 parts 2-imino-5-oxynaphthalene-1,7-disulfonic acid with 2-methylsulfonyl-4,5-dichloro 6-ethyl-pyrimidine acylated and the reactive groups containing coupling component with dianotated p-aminobenzylsultone acidic, a readily soluble reactive dye is obtained, the fabric containing cellulose fibers in brilliant reddish tones Orange tones colors. One impregnates cotton or cellular tissue on one Foalard at 20 - 250C with a solution containing 30 g per liter of liquor the dye described in this example, paragraph 1; 100 g Contains urea and 20 g of soda, squeezes onto a moisture content of approx. 100% and rolls up the moist tissue again. After standing for 24 hours at room temperature, the fabric is rinsed, Soaped and dried in usual wines at the boil. You get one brilliant scarlet coloration of good nali and light fastness. One impregnates full building fabric or full cellular fabric on a padder at 20-250C with a solution containing 30 g of the in diee «example, paragraph 1, described dyes, 100 g urea contains around d 20 g of soda, squeezes to a moisture content of approx. 100 X and steams for 30 seconds at 1030C. After rinsing, boiling Rope and drying one also gets ice brilliant acharlach- iarbese staining with good Na8 bond strength. Basmwllgevebe is impregnated with a Lisung from 20 - 250C eiert, which per liter of liquor 20 g of the according to this example, paragraph 1, available dyes and 0.5 g of a non-ionic network means (z. B. a polyoethylated oleyl alcohol) and S. Contains 150 g of oxygen and 15 g of ratr: umbicarbonate . Afterward the fabric is placed between two rubber rollers on a moist 100% squeezed off. After intermediate drying at 50 - 600C it is heated to 1400C for 10 minutes and the Holding staining rinsed thoroughly with hot water and 10 minutes treated at the boil with a solution containing 5 g of Marseilles per liter Contains soap and 2 g of soda. Receives after rinsing and drying you get a strong scarlet color of good wet and dry Lightfastness. If you print on cellulose fabric with, a printing paste that in the kilogram 30 g of the one described in this example, paragraph 1 Dye, 100 g llariistoff, 300 g water, 500 g alginatvecdickuag (60 g sodium alginate per kilogram of thickening), 10 g soda and 10 g of the hatriumaalzea containing 3-nitrobenzenesulfonic acid and which was made up to 1 kilogram with water, then Intermediate drying and then in a suitable steamer for 30 seconds steaming at 103 - 1150C, so you get after the coils and boiling Seifeq has a strong scarlet color with good fastness properties. 100 parts of wool are placed in a bath at 400C which in 5000 parts of water 1.5 parts of the in this example, paragraph 1, described dyes and 6 parts of 30% acetic acid and 0.5 Share a polyethylated: n hydrocyclic stearylamine Contains derivatives. The dye bath is brought to a boil in 30 minutes. brought, then an hour is dyed boiling. After rinsing After drying, it is brilliant, easy to wash, tumble and lightfast scarlet coloration. Example 620 28.9 parts of 2-amino-i-methylbene: ol-3,5-disulfon- acid (monosodium aln) and couples the diaso compound with 13.7 g 1-Aaiho-2-ethoxy-5-methylben: ol in weakly acidic medium. Of the obtained Konoa: ofarbatoff is isolated and subsequently or also immediately diasotized in solution without isolation and containing 25.3 parts 2-methylamino-5-hydro: ynaphthalene-7-sulfonic acid coupled with alkaline. The disazo dye obtained is made by adding sodium chloride Ausieaalsen, vacuumed and the isolated product with about 50 parts crystallized copper sulfate, 40 parts diethanoluin, 50 parts Ammonia (D: 0.88) metallized in 5 hours at 95 - 100 ° C. The dye is made from the fighting solution by adding salt and versichtiigea acidification isolated. The sacrificed amino-disazo dye is now aqueous Solution at pH 7 - 8 at a temperature of 60 to 65 ° C with 24.0 parts 2-Yethylsulfonyl-4,5-dichloro-6-methyl-pyrimidine acylated, whereby the pH-aert is kept in the specified range by soda liquor. After the acylation has ended, the dye is treated with sodium chloride Imeliert and dried at 35 ° C. The dye corresponds to in Fese of the free sulfonic acid of the formula: he dyes cellulose fabric according to the iteaktis dyes known processes in wet and lightfast navy blue tones. In a similar way, other inventive greetings can be found Produce dyes if one uses the above-mentioned monoasolarb- Substance of 2-amino-l-methylbene-3,5-disulfonic acid and 1-amiao- 2-retboay-5-methylbenzol with the values given in the following table led amnonaptitol sulfonic acids and 2-llethy-lsulfonyl-4,5-dichloro 6-methyl-pyrimadine according to the instructions given above combined. Kul! J! Lunjrkomj2onente . 2-amino-5-hydroaynaphtlealin- 1.? -Disulfonic acid 2-amine-8-hydrozynaphthalene- 3.6-disulfe @ aa @ ure The dyes obtained are blue in color. Example 621 0.1 Hol 4-ureido-2-amino-1-hydrozybene-sol-5-sulfonic acid Diasetiert and soda-alkaline with 0.1 Hol i-Amino-8-hydrezy- aa-Lahthalin-2,4-diaulfonic acid coupled. the viril with caustic soda to a content of 2 mol% liter. put uad in there; Hours under reflux to saponify the Boiled ureide group. After getting viril with hydrochloric acid neutralized. By adding 25 parts of copper sulfate and 100? Rush 2N sodium hydroxide solution viril the dye at 45 ° C and one pg-vor from 4 - 6 wetallized and after 30 minutes at Pf T- ass and Temperaturesfrom 60 -70 ° C with 091 Y®1 2-ethylsulfonyl-4,5-dichloro-6-methyl-pyrimidine acylated.The received Dye of @ gormel will be panned out. A blue color is obtained on full trees. Example 622 One made from 600 g of technical 96% isem copper phthalocyanine manufactured neutral paste of KnpterphthaloeYanin-3,3 ', 3 "- trisulfonic acid chloride is mixed with a little water, to 4 l adjusted and at a pH of 3.5-6.0 with 216 t N-methyl-N- (4'-amino-2'-aulfobensyl) -amine at initially 0 - 30C, at last 20 - 350C, with the addition of 300 ml (= 295 s) of pyridine reacted and after the pyridine bbi pii 9.0 with water vapor from the resulting Löaunt of copper phthalocyanine-disulfonic acid-monosulfanoic acid- (3'-aulfo-b'-ethyl-uinomethyl-anilide) distilled off. In the The solution brought to 60 ° C. is partially 330 g fine powdered 2-methylsulfonyl-4,5-dichloro-6-methyl-pyrimidinein the course of 1 to 2 hours interspersed and byAddition of diluted Caustic soda a pHfrom 7.5 -Sustained 8.5. At the same time will if necessary, the reaction mixture is diluted with water to such an extent that the Dye always remains dissolved. Ilea receives 10 l of dye solution, which can be removed from excess Ae'lierugaittel separated off by adding acetic acid to pH 7.0 represents and darsh stirring in 2.5 1 concentrated xochea-lsm- Lisaag falls. Hash suction and drying at 30 ° C gives ran a clear turquoise bubble dye, which is obtained from a soda-alkaline solution at d, 60 ° C with, very good yield and wash fastness on cotton is fixed. If the NPc-3,3 ', 3'-trisalphonic acid chloride is used as an gaagamaterial, you get just a little greener, turquoise-blue with equal wrtvellen Eigamaehaften. Example,.- 0.1 moles of the aminoazofarbetoffee of the formula - manufactured according to the information in German patent specification 1,115,865 (Registration F 27466 IV b22 a ) by coupling the Diazoniu® connection 2 iminenaphthalene-4,8-disulfonic acid with i-aminonaphthalene-6-sulfonic acid, Further diazotization @ desreceived Aminoazofarbatoifes, Domes with the equivalent amount 2,5-Lliaminonaphthalin-4,8-disulfonic acid and conversionin the aminotriazole -will be in 10 () () parts by volumeec2.Wasger at pli6th dissolved and stirred at a temperature of 60 - 65oC with 24 parts of 2-methylsulfonyl-4,5-dichloro-6-methyl-pyrimidineoffset. You dull them slowly released hydrochloric acid with @odalowuug until the reaction ends is. Afterwardthe dye is through To-rabeof sodium chloride secluded,isolated andat approx. 5 ()%dried in vacuum.

It is a yellow powder that is soluble in water with a yellow color. Example 624 38.9 parts deg by soda-alkaline coupling from 6-nitro-2- diaso-l-hydr®zybensol-4-sulfonic acid and 2-hydroxynaphthalene hold dyes in 200 parts of water at pH 8 at a temperature of 70 - 800C. In this suapenaion one adds 67.9 parts of 1 chromium atom to 1 molecule of dye containing chromium complex compound of the azo dye from 4-chloro 2-diaso-l-hydrozybensol-6-aulfonic acid and 1-amino-8-hydrocyclic naphtbalin-3,6-disulfonic acid, the pH being adjusted by adding dropwise ' Sodaläsaa4 is held between 7 and 9. After 20 minutes at 70 - 800C a dark blue solution has formed. The paper- ahromatograma shows that a uniform mixed complex stand « is. The mixed complex is within one hour at 65p c and pH 7 - 8 with 2690 parts of 2-liethylaulfonyi-4,5-dichloro = 6-methyl- pyrisidine acylated, the pH being adjusted by the dropwise addition of a soda solved in the specified area is held. The acylated color Substance is washed out with 20 X Yalius <chloride, filtered off and added 50 ° C dried :. A dark powder is obtained that dissolves in water with blaFarbe solves. As pentasodium, the paraffin corresponds to the formula He colors trees full of trees according to the examples 3 @ 7 - @% y marked Process in gray to black tones. From the initial cooperation given in the following table Valuable dyes can also be found in the in None given in this example received. For making of these dyes was always the azo dye, which was mixed in 2: 1 complex carries the reactant group, used as a 1: 1 chromium complex. 62.0 parts of trisodium as the one by soda-alkaline rbppluna ans dianotated 4-chloro-2-auino-1-hydrocybene-sol-6-sulphonic acid and 1- amines -8-hyärozyaapbthalin-3; 6-disulfonic acid obtained parb- Substances previously in 300 parts of water at 70 - 800C and a pH from 8 - 9 with 54.2 parts the 1: 1 Chronkomplezea "of the dye from 6-nitro-l -dienes -2-hydrozynaphthalene-4-sulfonic acid and 2-üy- drozynaphtbalin displaced. After 10 minutes, a deep blue solution formed. The Miach complex takes about an hour at 60 - 65 ° C and one pH 6.5 - 7.5 with 26: rapid 2-diethylsulfonyl-4,5-dichloro-6-methyl- pyrisidine aaylated. In the case of eggs, the pn value is determined by dropping them held by the Soialiamy Kometamt. The acylated dye will deposited with 20x sodium chloride, suctioned off and at 30 ° C 6e ":, recknot, Obtained on äamvalle after in Example? V c = @ - drive a rlamschvar: en pressure of excellent light and Vase work. Y-- n Example 6 6-i 1-Amine-4- (4 ° -aminophenylamino) -anthraquinone-2, S, 8-tri- Salfenic acid are dissolved as Na salt in 180 n1 water at 400C, the solution adjusted to pH 8 and at 65 - 70 ° C 3.0 g of 2-yethyleulfonyl- -4,5-dichloro-6-rethyl-pyrinidine in small portions registered. Equilateral allowed to diluted caustic soda such * Ensure that a pH of 7.5 - 8.5 is maintained during unsetting. will hold. Stir at 65-700C until all lasgamis material has disappeared, sucks off excess ? tTimidine derivative and salted at 100C with so much solid Matriamiakierid so that about a 10% sodium chloride solution ve r runs. You sing, wash with a little saline solution and dry the esksltemen dye of the formula ast «badb 400C in vacuum. About 8.5 g of the dye are obtained in let of blue-green needles. The dye dyes cotton according to iür @ Reaktiviarbatoffe iiblialten process in strong blue-green tones of good NaH- aad Lierteebtreit. The i-amino-4- (4 ° -amine- phenylamino) anthraquinone-2,5,8-trisulionic acid became as follows obtained: 31.2 gp-phenylenedismine are under nitrogen in a Solution of 62 g of 1-amino-4-bromo-anthraquinone-2,5,8-trieulfonic acid Sodium and 12 g of soda were added and CuCl paste was added Stirred at 400C until no disulphated bronamic acid is more detectable. Now the solution is mixed with dilute salt acid, the precipitating dye is sucked off, mixed with washed with dilute hydrochloric acid, in 300 ml of water with as much dilute sodium hydroxide solution is added so that the solution enters at the top and the dye in the heat is precipitated as the Na salt; the "pro- The product is then washed and dried. In the aforementioned examples, the reactive components @ used can be exchanged for one another under the same or similar reaction conditions. Likewise, the reactive components indicated on page 11, paragraph 2, can be used in the reactions according to the preceding examples instead of the reactive components indicated there with equally good or similar results. - example- 651 79.9 parts of the Belgian patent no. 599 581 represented lainoaso compound of the formula are dissolved in 500 parts of water at 60 - 65C and dissolved at that temperature-temperature while stirring with 24 parts of 2-liethylsulfonyl-4,5-dichloro-6-methpl- pyriaidin added. The slowly released hydrochloric acid is mixed with soda Solution blunted, keeping a pH between 5 and 6 . After the condensation has ended, the dye is made by adding 150 Parts of potassium chloride salted out, isolated and vacuumed at approx. 50oC dried. A dark powder is obtained, which dissolves in water with blue paint dissolves and cotton in reddish blue tones from auage- colors that are fast to light and washing. In addition to the dye, as is evident from the introductory description and is known from practice, the colorants according to the invention also contain salts, some of which originate from the manufacture of the dyes and / or can also be added as an adjusting agent * and, as required, other adjusting agents and Aids. Example 652 12.5 parts of 3-amino-4-sulfobenzyl-N-methylamine are dissolved in 150 parts by volume of concentrated hydrochloric acid. 4 parts of sodium nitrite in 20 parts by volume of water are added dropwise to the solution. The resulting clear diazonium salt solution is added dropwise at 30 ° -350 ° C. to an aqueous solution of an equimolar amount of 1-N-benzoyl-amino-8-oxynaphthalene-4,6-disulfonic acid and 16 parts of sodium bicarbonate in 200 parts by volume of water. The dye partially precipitates and is brought back into solution by adding 2000 parts by volume of water. Then 20 parts of 2, -4-His, .methylsulfonyl-6-methyl-pyrimidine are added to Hei 55-600C. By adding a soda bob, the pH value is between? and 8 held. When the acylation is complete, as can be seen from the consumption of soda, the dye is separated off with 10 percent table salt, then suctioned and pressed. and dries in a vacuum oven at 300C. The ER-preserved bluish red dyestuff in the form of so 311_ free acid of the formula t N - N 3 3; E NH_OCC6H5 so 3 H C 302 C HO -CH _ CH3 Example 653: To an ice-cold aqueous-methanolic suspension of 50.1 parts by weight of 2,4,6-trisphenylsulfonyltriazine- (1,3,5), which contains 2 parts by weight of the condensation product of oleyl alcohol with 20 mol of ethylene oxide, is added dropwise with constant blunting acid liberated to pH 5 to 6 at about 00C 1500 parts by volume of an aqueous solution of 56.8 parts of the trisodium salt of an aminoazo compound, which was obtained by coupling diazotized 1-aminobenzene-2-sulfonic acid with 1-acetylamino-8-hydroxynaphthalene- 3,6-disulfonic acid in the presence of sodium carbonate and cleavage of the apetyl group by heating in an aqueous solution containing about 4% caustic soda to 80 to 850C. The solution is stirred for a few minutes at 0 ° to 50 ° C. and pH 5 to 6, then adjusted to about pN 6.5 with 100 parts by volume of a solution of 185 parts of KH2PO4 and 262 parts of Na2HPO4 # 12 H20 in 1000 parts of water. The resulting dye of the formula is salted out with 200 parts by weight of sodium chloride, filtered off with suction and washed with acetone. The dark powder is then mixed with 10 parts by weight of a mixture of 42 parts of Na2HPO4 and 75 parts of KH2PO4 and dried at 20 to 300C in a vacuum. It dissolves in water with a red color. The same dye is obtained when 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid, acylated with trisphenylsultonyltriazine, is coupled with diazotized 2-aminobenzenesulfonic acid at pH 5 to 6 and a temperature of 0 to 50.degree. When printing cellulose fabric with soda as the acid-binding agent , the dye obtained according to one of the instructions given gives a strong blue-tinged red print with good wet and light fastness properties. The same dyeings on cotton fabric are obtained from a long liquor by the thermosetting process or by the cold padding process. Example 654: To an ice-cold aqueous-methanolic suspension of 18.5 parts by weight of 2,4,6-tris-phenylsulfonyl-triazine- (1,3,5), which contains 1 part by weight of the condensation product of oleyl alcohol and 20 mol of ethylene oxide, is added dropwise with constant blunting of the acid released to pH 5 to 6, the solution, neutralized with soda, of 19.2 parts by weight of the dye of the formula in 1000 parts of water. The mixture is stirred for a few minutes at 0 ° to 50 ° C. and pH 5 to 6, then adjusted to about pH 6.5 with 50 parts by volume of a solution of 185 parts of KH2PO4 and 262 parts of Na2HPO4 # 12 H20 in 1000 parts of water. The resulting dye of the formula is salted out with 50 parts by weight of sodium chloride, pressed out, mixed with 5 g of the phosphate mixture mentioned in Example 653 and dried at 20 to 30 ° C. in vacuo. It is a dark powder, which dissolves in water with a blue color, gives a blue color on cellulose fibers when it is made from a soda-alkaline solution at room temperature or from an aqueous solution by padding and post-treatment of the padding material, if necessary after drying, with a sodium hydroxide solution and Aqueous solution containing sodium chloride, or by pressure in a printing paste containing urea and soda. The dyeings are characterized by high wash and lightfastness. The reaction of 2,4,6-Tdsphenylsulfonyl-triazin- (1,3,5) with other amino group-containing anthraquinone dyes also gives valuable reactive dyes which correspond to the following formulas: These also dye cellulose fibers blue. Example 655: 54.4 parts by weight of 2,4,6-tris- (o-methylphenyl) -sulfonyl-triazine- (1,3,5) are substituted analogously to the instructions in Beiqiel 653 with 49.7 parts of the disodium salt of the deacetylated aminoazo compound from diazotised 4-Aminoanisolsulfonsäure- (3) and 2-Aoetylamino-5-oxynaphthalene-7-sulfonic acid in a way to give the dye of the formula It is a red-brown powder that is soluble in water with a red color, which dyes cellulose materials in real scarlet shades. Substituting analogous to that of Example 653-2,4,6-tris-phenylsulfonyl-triazine (1,3,5) with aminoazo compounds other in a way to give the dyes shown in the following table, the Celluiosematerialien in reasonable Coloring led shades: Further red or orange-colored dyes are obtained if those dyes are used which arise from the components listed in Examples 19 to 29 and are not mentioned here. Example 656: In Example 653, instead of the aminoazo dye mentioned, 0.1 mol of the coupling product of diazotized 2-aminonaphthalene-4,8-disulfonic acid and 3-aminotoluene is used and the procedure is otherwise as indicated there, the result is the part of the formula It is a yellow powder, soluble in water with a yellow color, which dyes pellulose materials in real yellow tones. Yellow colorations on cellulose materials are also obtained with the dyes of the formulas, which are accessible in an analogous manner: Further yellow dyes of this type can be obtained with appropriate use of the dyes from Examples 4 to 17 on condensation with 2,4,6-tris-phenylsulfonyl-triazine- (1,3,5). Example 657: 45.4 parts by weight of 2,4,6-tri $ (p-methylphenyl) -sultonyltriazine- (1,3,5) are added to 48.3 parts by weight of the deacetylated aminoazo compound from diazotized 4 in accordance with the instructions in Example 653 - (H-Acetylamino) -2-aminobenzoZ-sulfonic acid and 1- (4'-3ulfophenyl) -pyrazolone-5-carboxylic acid- (3) um, the dye of the formula is formed It is a yellow powder which is soluble in water with a yellow color , with which cotton can be dyed in greenish yellow shades with good fastness properties.

Analogue produced dyes with a similar shade on cotton are: Example 658: 0.1 mol of the copper complex compound of the formula is dissolved in 1500 parts of water at pH 6 and with vigorous stirring at 0 to 50C while blunting with soda solution with a methanolic-aqueous suspension of 0.1 mol of 2,4,6-tris-phenylsulfonyl-triazine- (1,3,5 ), which contains 2 parts by weight of an emulsifier , condenses. The reactive dyestuff thus obtained dyes cellulose materials in wet, rub.- and lightfast ruby tones. The metal complex compounds given in Examples 48 to 63 can be converted to reactive dyes of the sulfonyltriazine series under analogous conditions. Very brilliant blue dyeings on cotton are made with the dye of the formula which is built up in a corresponding manner obtain. Example 659: In the solution of 21 parts of the sodium salt of the 1,3-Diaaino- bensel-6-salfonsäare in 100 parts of water are stirred well 50.1 parts by weight of 2,4,6-tris-phonylsalfonyl-triasin- (1.3 "5) in given aqueous-nothanelischer solution and at 0 - 50C under constant Blunt the released acid to pH 5 - 6 stirred for so long. until a test at Diasotierea and Rappeln for 1-Hydrozynaphthalin- b-sulfonic acid gives a clear, yellowish red color. The Stand up dye wipe product is directly with the addition of ice 7 parts of sodium nitrite and 28 parts of concentrated hydrochloric acid diast- and then with a submitted solution of 47 parts the Natriuasalses of 1-Hensoylaaino-8-hydro: ynaphthalene-3,6-di- Snlfenic acid and 12 parts of soda combined in 200 parts of water, with Coupling to the dye of the formula occurs, the ausgesalsen, suction filtered, washed and dried at 20 - 300C is dried in vacuum. The dye can be found in water red color and provides clear, bluish tint on cellulose materials red dyeings and prints with high fastness properties. In an analogous manner, dyes of the specified shades can be obtained from the combinations specified in Examples 31 to 46. Through condensation of the inapiel "64 described inapiel Products of copper phthalocyanine sulfochlorides and 1,3-diaminobensel 4-aulfona acid with 2,4,6-tris-phenylaulfonyl-triasin- (1,3,5) at 5 - 100G and a pH value of 6 - 7, dyes are obtained, house wool and Begeneratcellulose after one of the above-mentioned coloring or Printing process in clear tones with good NaB, rubbing and light dyeing authenticity. A particularly valuable type of Parbatoff is obtained when the condensation aation product of Rupferphthalocyaninetrasulfochlorid and 1,3-Diasine- bensol-4-aulfona acid is reacted with a #b noniushydrozydlösung in such a way that that a connection of the following annotation is obtained: where a: 2.7-2 and b: 0.3-1. The condensations with the reactive components, for example 2-methyl- sulfonyl-4,5-dichloro-6-ethylpyriaidin, 2-methylaulfonyl-4-chloro-6-ethyl- pyriaidin, 2,4,6-tria-phenylsulfonyl-triozine- (1,3,5), 2-methylsulfonyl- 4-chloro-5-broa-6-aethylpyriaidin, 2-methylaulfonyl-4-chloro-5-cyanopyri- midin etc: are carried out under the usual conditions Heissiel 661: Will the oil groups described in Examples 65-326 containing-harbatoffs or dye precursors, as in the two play 653 - 660 stated, with 2,4,6-tria-phenylsnlfenyl-triasin- (1,3,5) condensed and, if necessary, further appropriations, Hisier color stains are obtained, the stains excellent Resulting in fastness. $ Example 662: Are the dyes described in Examples 653-661 with two phenylsulfonyl groups per triazine ring in a molar ratio of 1: 1 at 20-700C while the acid released is blunted with colorless ones Amino, hydroxy or mercapto derivatives implemented, for example N- Methyl aniline, aminobenzene-3-sulfonic acid, aminobenzene-4-sulfonic acid, Aminobenzene-3-carboxylic acid, ethylamine, B-Hydrozyäthylamin, 0, B'-dihydroxy diethylasiin, N, N-Dinethylhydrazim, methyl alcohol, ethyl alcohol, trichloro ethyl alcohol, phenol, phenol sulfonic acid, methylnercaptan, thiophenol or thiourea, so that only one phenylsulfonyl group per triazine ring remains, reactive dyes are also obtained which Dyeings with excellent NaB and acid fastness properties. The äls »reactive component used 2,4,6-tris-phenylsulfonyl-triazine- (1,3,5) is by oxidation of 2,4,6-tris-pheaylmercapto-triazine- (1,3,5), bei.apielweise by chlorine in aqueous-methanolic solution at -10 am + 100C, s * gäaglich. Example 663: If in Examples 327-651 the 2-methylsulfonyl-4,5-diehler- 6-methylpyriaidin or 2,4-bis-methylsulfonyl-5-chloro-6-methylpyrisidine by the 2-methylsulfonyl-4-chloro-5-broa-6-Bethylpyriaidin or the 2,4-bis-wethylaulfonyl-5-bromo-6-methylpyriaidin replaced, so color obtain substances with similarly good properties. Example 664: If in Examples 1 -, 326 the 2-MethyXsnlfonyl-4-chloro-6- methylpyriaidin or the 2,4-bis-nethylaulfonyl-6-methylpyrimid.in through d in 2-methylaulfonyl-4-chloro-6-phenylpyrinidine or the 2,4-bis-sethylacl- fonyl-6-phenylpyrinidine replaced, so-Farbk-@o-.ffe with similar = goodQ- Properties preserved. $ Example 665: Is 32 in the examples? - 651 the 2-methylsulfonyl-4,5-dichloro 6-methylpyriaidin or the 2,4-bis-methyleulfonyl-5-chloro-6-methylpyrimi- s _ din by the 2-Kethylsulfonyl-4,5-diehlorpyrimidin or the 2,4-Bie- , methyleulfonyl-5-chloropyrimidine is substituted, so paraffin kits are similar good properties. Example 666: If in Examples 1 - 326 the 2-Methllsulfonyl-4-chloro-6- methylpyrimidine by the 2-carbozymethylsulfonyl-4-chloro-6-methylpyrimi- replaced by din, similar dyes with better u ility- properties preserved. Example 667: 40.9 g of 1-amino-4 - (3`-amino-anilino-) nathraquinone-2-sulfonaLturo are dissolved neutrally in 300 ml of water. You put 26t5 g 2-methyleulfonyl-4,5-dichloro-6-methylpyrinidine. to, `warmed to 5000 and neutralizes the released balsic acid at p8 6 with 20% soda solution: After the reaction has ended, it is suctioned off and dried in vacuo at 5000. The finely powdered Intermediate product is carried Qingo in 220 ml of 15% oleum, whereby the internal temperature is kept below 3000 with external cooling, laugh finished sulfonation, the chromatographych . tracked is decomposed on -500 g of ice and. Dye from: - It is dissolved in 200 ml of water; with soda lye neutralized, heated to 75o0 and mixed with 10 ¢ cooking gal $ When cold stirring, the dye separates from the probable .Formula the end; it is suctioned off and dried at 50a0 in a vacuum. Of the farbotoff dyes cotton fabrics and regenerated cellulose fibers blue and has excellent barrel fastness o If one uses instead of the 1.-amino-4 - (. 3'-amino-anilino-) anthra- quinone-2-sulfonic acid the 1-amino-4- (3'-amino-anilino) -anthrachi- non-2,6-diaulphonic acid, one comes to a greenish blue of. comparable authenticity properties. : 3exs; irl C M 5 parts 1-, L-iiäl- Z.-4- (2 '. 6 1 -d? Methyl-3 -aminomethy l) -anilino-anthraquinone- 2.4'Adisulfonsäui@o are stirred in 80 parts of water and 0.4 parts 5o percent atroaäizge added, creating a neutral solution stands. At 550C one gives 2a7 parts 4-3, ethyl-5.6-dichloro-2-methylsulfonyl- pyrimiä.in and keeps at the specified temperature by dropping In soda solution, the pH value between 5 and 5.5. After 2-3 hours it is Reaction almost stalled. V: an gives another 0.5 parts of the Fyriridine derivative added and proceed as indicated until the reaction is finished. Residues are filtered off and added to the filtrate at 50.degree Add 1o parts of a 25 percent liaC1 solution and suck in the flakes crystallized dye at 250C. After 'rapid with 5 percent Na0l solution and drying gives 6.5 parts of a dark blue powder, which is very light and on cellulosic materials. wet-fast, clear red sticky blue reactive printing supplies. r Of the. Dye has the formula:, - Example 63 @ 2o. Parts 1-Amino-4- (4'-methylamnomethyl) -anilino-anthraquinone-2.6.2! - Sodium trisulfonic acid is zoo parts water at 600G with 12 parts 4-Uethyl-5.6-dichloro-2-methylsulfonyl-pyrimidine acylated, whereby the pH - # * lert the solution by adding dropwise 1N solo solution to 5 - 5.5, The reaction has ended after 5-6 hours. After filtering off gray Rüc: cstäncen is the dye at 2o00 by adding 50 parts of a saturated NaCl solution deposited 'filtered off, with 1o percent NaCl solution washed and tumbled. On cotton you get clear, greenish blue reactive prints with very good light and wet fastness properties. The dye corresponds to the formula: _ Example 6702 2o parts of 1-dmino-4- [28.6i-dimethyl-3 # - (3'8-aminobenzyl). "Aminomethylj- anilino-anthraquinone-2.6.4'f-trisulfonic acid iiatrium are divided into 160 parts wetter at 550G with 1.1 parts of 4-diethyl-5.6-dichloro-2-methylsulfonyl- pyrimidine acylated. The pH value is maintained by adding In Soca solution at 5 - 5.5. The reaction has ended after about 2 hours. 1S = on filtered from bright spots and salt out the dye with a little idaCl, fil- rubs off and dries. The product replenishes on cellulosic materials the above procedure, very clear blue prints, the particularly quickly reach their full depth and excellently a .ass; friction and light are real . The dye has the formula: O NH @ S03HQ. . .- -S N3 N S02GH3 HIC $ @ u0. 3 Example @@@ '. - _. . .. .-. 1o parts 1-umino-4- (2'.6 = dimethyl-3 = methylamino: le th "rl) -anilino-anthraquinone- 2.6-disulfonic acid is produced in 100 parts of water at 700C with 4 parts. 5o percent sodium hydroxide solution neutralized and dissolved. One gives 5.5 parts. 3h: add ethyl-4,5-dichloro-2-methyl-sulfonyl-pyriridine and drop at 7000 7n Sodalosun.- so that a pH-lert of 5 - 5.5 is maintained. After 6 hours, 2.6 parts of the pyrimylic derivative are added and left the reaction continued for another 6 hours. Then dilute it with loo parts of water, sucks off gray residues and adds 15 at 7000 Allocate a saturated NaOl solution, whereby the dye 'in small Crystals precipitates. After: lash with 1o percent NaCl solution and Drying gives a dark blue powder, which according to the described Process dyes cellulose fibers in clear blue tones. -. The dye has the prefix:

Claims (7)

Claims: 1. Process for the preparation of reactive dyes of the general formula where F is the remainder of an organic paraffin X indicates a grouping -1 =, _SO.-. - @ '# rylen-, R. -Alkylene- or -N = N- which directly J. @ it the remainder A and either directly or via a. -y @ eken-. member is linked to the remainder P, where R stands for Hydrogen or a substituent, "Av;flen" Zür an arylene radical and "alkylene" for a lower one Alkylene group, A is the remainder of a 6-g? iedaigen heterocyclic ring, the least-na a reactive sulfony, substituents av a carbon atom of the heterocyclic ring gobunder holds and the condensed aro "auhe LU." @ can have and m is a number of. 0.5 to 8 represented l! -x characterized in that one. in Parbsto @ ''. » odor Parba - @@ ofj, - precursors according to processes known per se at least introduce a group -XA, in which X and A have the meaning given, and that in the case of using paraffin precursors. converts these into the desired final dyes. 2. A process for the preparation of reactive dyes, characterized in that dyes containing amino or amide groups or dye precursors which have a reactive hydrogen atom on the amine or amide nitrogen, -with compounds of the general formula A -Y wherein A is a 6-membered heterocyclic ring represents, the at least one reactive sulfonyl substituents on a carbon atom of the heterocyc- contains the bounded lischen ring and the aromatic May contain fused rings, and Y an anionic 'represents splittable residue and, in the case of using dye veTpyveL "ttv), converts these in a suitable manner into the desired F.nd. colorants. 3. The method according to claim 2, characterized in that the compounds of the formula AY, -2-carboxymethylsulfonyl-4-chloropyrimidine, 2-methylsulfonyl-6-methyl-4-chloropyrimidine, 2,4-bis-methylsulfonyl-6-methylpyrimidine , 2,6-bis-phenylsulfonyl-4-methyl-5-chloropyrimidine, 2,4,6-tris-methylsulfonyl-pyrimidine, 2,4-bis-methylsulfonyl-pyrimidine-5-sulfonic acid chloride, 3,6-bisphenylsulfonyl-pyridazine , 3-P-Zethylsulfonyl-6-chloropyridazine, 3,6-bis-methylsulfonyl-4-methyl-pyridazine, 2,5,6-tris-methylsulfonyl-pyraziny, 1,3-bis-methylsulfonyl-2,4, 6-triazine, 1,3-bismethylsulfonyl-5- (3 # -sulfophenylamino) -2,4,6-triazine, 1,3-bismethylsulfonyl-5-phenoxytriazine, 1,3-bismethylsulfonyl-5-trichloroethoxy-triazine and numerous further 1,3 His-methylsulfonyl-2,4,6-triazines, 2,4-bis-methylsulfonylquinazoline, 2,4-bis-phenylsulfonyl-quinoline, 2-methylsulfonyl-4-chloropyrimidine, 2-chloromethylsulfonyl substituted in the 5-position -4-chloropyrimidine, 2-phenylsulfonyl-4-chloropyrimidine, 2,6-bis-methylsulfonyl-4-methyl- 5-chloropyrimidine, 2-methylsulfonyl-4-methyl-5,6-dichloropyrimidine, 2,6-bis-ynethylsulfonyl-4-methyl-5-bromopyrimidine, 2-methylsulfonyl-4-chloromethyl-5,6-dichloropyrimidine, 2-Methyl @ sulfonyl-4-methyl-6-chloro-pyrimidine-5-sulfonic acid chloride or 4,6-bis-methylsulfonyl-5-chloro-pyridazine are used. 4. Procedure according to Claims 1 and 2, characterized in that, after the condensation, the obtained Subjects dyes to the usual conversion reactions, especially metallization. Acylation, reduction and / or sulfation reactions. 5. The method according to claim 2, characterized in that one aminoazo dyes of the formula where B and D are aromatic carbocyclic or heterocyclic radicals, B in particular a radical of a carbocyclic diazo component of the benzene or naphthalene series and D in particular the radical of an enol or phenolic coupling component, B and D can otherwise have any further substituents, including such azo groups, R is a substituent or preferably hydrogen and m 'is an integer, preferably the number 1 or 2, condensed with compounds of the formula AY in which A and Y have the meaning given in claim 2. 6. The method according to claim 2, characterized in that one is aminoanthraquinone dyes of the formula wherein Z is hydrogen or a substituent, among these in particular a sulphonic acid type, means " p the number 1, 2 or 3 and R 'a SubseAuent or preferably denote hydrogen, with compounds of the formula A -Y in which A and Y have the meaning given in claim 2, reacts and, if appropriate, sulfates the dyes obtained in this way. 7. The method according to claim 2, characterized in that azaporphine dyes of the formula where Pc is the radical of a phthalocyanine, in particular a copper or nickel phthalocyanine or a tetraphenyl copper or nickel phthalocyanine, Z is hydrogen or a substituent, among these in particular a sulfonic acid group, r is the number 1 or 2, q the number 0, 1 or 2 and R is a substituent or preferably hydrogen and m "is a number from 0.5 to 4, with compounds of the formula AY in which A and Y have the meaning given in claim 2, condensed and optionally, the dyes thus obtained sulfonated. B. the method of claim 2, characterized in that a diazo or coupling component, comprising a reaction-capable amino or amide group, with a compound of the formula a y wherein a and Y in the have the meaning given Änaprueh 2, condenses and converts the intermediate products thus obtained by diazotizing and / or coupling in azo dyes. 9. variation of the method, according to claim 2, dad urch overall indicates that a compound -A-NH2 wherein A is as defined in claim 2, diazotized and with a coupling component f1, which also Asograpgan may have united. 10. The method according to claims 1 to 9, characterized net that one builds up such dyes or. AusaafkoQ- Discarded components that contain one or more sulfonic acid groups exhibit. 11. The method according to claims 1 to 10 characterized egichnet ,, that the reactive sulfonyl substituents in the Starting or end products are methyl sulfonyl groups. ..12. Reactive dyes of the formula where F is the remainder of an organic dye, X is a group -S02-, A.rylen-, A lkylen- or -N = N-. Represents, which is linked directly to the radical A and either directly or via a bridge member to the radical F, where R is hydrogen or a substituent, " Arylene "stands for an arylene radical and" alkylene "stands for a lower alkylene radical, A represents the radical of a 6-membered heterocyclic ring which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the heterocyclic ring and which can have fused aromatic rings, and m represents a number from 0.5 to. 13. Reactive dyes of the formula of claim 12, wherein F has one or more sulfonic acid groups. 14. Reactive dyes of the formula F1 (N = NA) k in which F1 represents the remaining constituent of an azo dye, A has the meaning given in claim 12 and k stands for the number 1 or 2. 15.: Reactive azo dyes of the formula wherein B and D aromatic or carbonyelische heterocyelische radicals, B is preferably the radical of a earboeyclischen Diazokompöriente the benzene or naphthalene group, and D is preferably the radical of an enolic or phenolic coupling component, B and D in the rest of any other substituents, including other Azo groups, R is a substituent or preferably hydrogen, Q is a direct bond or a group -So Zäh-1 m 'is an integer, preferably the number 1 or 2 and A is the remainder of a 6-membered heterocyclic Rigges which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the heterocyclic ring and which may have fused earbocyclic rings. 16. Reactive anthraquinone dye oven of the formula where Z is hydrogen or a substituent, among these is in particular a sulfonic acid group, p denotes the number 1, 2 or 3, R denotes a subatituent or preferably represents hydrogen, Q is a * direct Bond or a group -SO -, and A represents a 6-membered heterocyclic ring, the at least one reactive sulfonyl substituent to a carbon atom of the heterocyclic ring contains bonds and the condensed earbocyclic May have rings. 17. Reactive azaporphine dyes of the formula where Pc is the radical of a phthalocyanine, preferably a copper or nickel phthalocyanine or a tetraphenyl copper or nickel phthalocyanine, Z is hydrogen or a substituent, among these in particular a sulfonic acid group, r is the number 1 or 2 and q is the number 0.1 or 2, R is a substituent or preferably hydrogen, Q is a direct bond or an -SO grouping, A is the radical of a 6-membered heterocyclic ring which has at least one reactive sulfonyl substituent on a carbon atom of the heterocyclic ring contains bonded and the further carbocyclic rings may contain condensed, and m ″ stands for a number from 0.5 to 4. 18. Dyes of claim 15, wherein B and / or D have one or more sulfonic acid groups. 19. Dyestuffs of claim 16 which have one or more sulfonic acid groups. 20. Dyestuffs of claim 17 which have one or more sulfonic acid groups. 21. Process for the preparation of reactive dyes of the general formula wherein F is the residue of an organic dye , X is an amino group, A is a pyrimidine ring dAratellt which contains at least one leactive sulfanyl substituent bonded to a carbon atom of the heterocyclic ring, and -m is a number from 0.5 to 8, .. characterized that one introduces at least one pyrimidinylamino group bonded to a ring carbon atom of an aromatic ring into dyes or dye precursors by processes known per se, which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the pyrimidine ring, and in the case of the use of dye precursors, these into the desired final dyes converts. 22. A process for the preparation of reactive dyes, characterized in that amino group-containing dyes or paraffin precursors which have a reactive hydrogen atom on the amine nitrogen, with compounds of the general formula A i --- Y wherein A represents a pyrimidine ring which has at least one active sulfonyl substituent Contains carbon atom of the heterocyclic ring bonded and Y represents a residue which can be removed by aasession, and, in the case of the use of dye precursors, converts them in a suitable manner into the desired final dyes. 23. The method according to claim 22, characterized in that the compounds of the formula A16Y are 2-Carbozymethylaulfonyl-4-chloropyrimidine, 2-methylsulfonyl-6-methyl-4-chloropyrimidine, 2,4-His-methylaulfonyl-6-methyl-pyrimidine , 2,6-ice-phenylaulfonyl-4-methyl-5-chloropyrimidine, 2,4,6-trismethylaulfonylpyrimidine, 2,4,5,6-tetramethylsulfonyl-pyrimidine, 2-methylsulfony 1-4-methyl-5-nitro- 6-chloropyrimidine, 2-methylsulfonyl-4,5-dimethyl-6-chloropyrimidine, 2-ethylsulfonyl-4-methyl-5,6-dichloro-pyrimidine, 2-methylsulfonyl-4,6-dichloro-pyrimidine, 2,4, 6-Trismethylsulphonyl-5-chloro-pyrimidine, 2-methylsulphonyl-4-carboxy-6-chloro-pyrimidine, 2-methylsulphonyl-4-chloro-pyrimidine-5-sulphonic acid or 4,6-bis-methylsulphonyl-pyrimidine are used. 24. The method according to claims 21 to 23, characterized in that there is used as the reactive component 2-methylsulfonyl-4,5-dichloro-6-methylpyridine. 25. The method according to claims 21 and 22, characterized in that, after the condensation, the dye obtained is subjected to customary conversion reactions, in particular metallization, acylation, reduction and / or sulfation reactions. 26. The method according to claims 21 to 24, characterized in that one aminoazo dyes of the formula where B and D represent aromatic carbocyclic or heterocyclic radicals, B in particular a radical of a carbocyclic diazo component of the benzene or naphthalene series and D in particular the radical of an enolic or phenolic coupling component, B and D otherwise have any further substituents, including azo groups can, Ri is a substituent or preferably hydrogen and m 'is an integer, preferably the number 1 or 2, with compounds of the formula A1 Y in which A1 and Y have the meaning given in claim 22, condensed. 27. The method according to claims 21 to 24, characterized thereby marked, that one Aminoanthrachinonfarbstoffe of formula where Z denotes hydrogen or a substituent, among these in particular a sulfonic acid group, p denotes the number 1, 2 or 3 and R1 denotes a substituent or preferably hydrogen, with compounds of the formula AY. wherein A1 and Y have the meaning given in claim 22, _ -reacted and optionally sulfated the ao obtained dyes. 28. The method according to claims 21 to 24, characterized in that one azaporphine dyes of the formula where Pc is the radical of a phthalocyanine, in particular a copper or nickel phthalocyanine or a tetraphenyl copper or nickel phthalocyanine, Z is hydrogen or a substituent, among these in particular a sulfonic acid group, r is the number 1 or 2, q the number 0.1 or 2 and R is a substituent or preferably hydrogen and m '' is a number from 0.5 to 4, with compounds of the formula A1 ` Y in which. A1 and Y have the meaning given in claim 22, condensed and, if appropriate, sulfated the dyes obtained in this way. 29. Process according to claims 21 to 24, characterized in that a diazo or coupling component which has a reactive amino group is condensed with a compound of the formula A1 --- Y wherein A1 and Y have the meaning given in claim 22 and converting the intermediate products thus obtained into azo dyes by diazotization and / or coupling. 30. The method according to claim 21, characterized in that a compound A 1 @ NH2 in which A1 has the meaning given in claim 21, dianotized and combined with a coupling component F1, which can also have azo groups. 31. Process according to Claims 26 to 29, characterized in that the reactive component used is 2-methylsulfonyl-4,5-dichloro-6-methylpyridiriver. 32. The method according to claims 21 to 31, characterized in that such dyes are built up or starting components are used which have one or more sulfonic acid groups. 33. reactive dyes of the formula wherein F is the radical of an organic dye, x represents an amino group, A dirstellt a pyrimidine ring, containing at least one bound eaktiven sulfonyl substituent to a carbon atom of the heterocyclic ring, and m represents a number from 0.5 to eighth 34. Reactive dyes of the formula of claim 33, wherein F has one or more sulfonic acid groups. 35. Reactive dyes of the formula F lY k in which F represents the remaining constituent of an azo dye, A has the meaning given in claim 33 and k represents a number 1 or 2. 36. Reactive azo dyes of the formula where B and D represent aromatic carbocyclic or heterocyclic radicals, B preferably represents the radical of a carbocyclic diazo component of the benzene or naphthalene series and D preferably represents the radical of an enolic or phenolic coupling component, B and D otherwise any further substituents, including others Azo groups, R1 represents a substituent or preferably hydrogen, m 'represents an integer, preferably the number 1 or 2, and A1 represents a pyrimidine ring which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the heterocyclic ring. 37. Reactive anthraquinone dyes of the formula where L - is hydrogen or a substituent, among these in particular a sulfonic acid group, p is the number 1, 2 or 3, R is a substituent or preferably hydrogen and Al is a pyrimidine ring which has at least one reactive. Contains sulfonyl substituents bonded to a carbon atom of the heterocyclic ring. 38. Azaporphine reactive dyes of the formula where Pc stands for the remainder of a phthalocyanine, preferably a copper or nickel phthalocyanine or a tetraphenyl copper or nickel phthalocyanine, Z denotes hydrogen or a substituent, among these in particular a sulfonic acid group, r denotes the number 1 or 2 and q denotes the number 0, 1 or 2, R1 is a substituent or preferably hydrogen, A is a pyrimidine ring which contains at least one reactive sulfonyl substituent bonded to a carbon atom of the hydrocyclic ring, and m ″ is a number from 0.5 to 4 stands. 39. Dyestuffs of claim 36, wherein H and / or D have one or more sulfonic acid groups. 40. Dyestuffs of claim 37 which have one or more sulfonic acid groups. 41. Dyestuffs of claim 38 which have one or more sulfonic acid groups. 42. Dyestuffs of claim 33, wherein Al represents the 2-methylaulfonyl-5-chloro-6-methylpyrimidinyl-4 radical. 43. Dyestuffs of claim 36, wherein A stands for the 2-methyl-1-sulfonyl-5-chloro-6-methylpyrimidinyl-4 radical. 44. Dyestuffs of claim 37, wherein A1 stands for the 2-methylsulfonyl-5-chloro-6-methylpyrimidinyl-4-13 radical. 45. Dyestuffs of claim 38, wherein A1 stands for the 2-methylsulfonyl-5-chloro-6-methylpyrimidinyl-4 radical. 46. Dyestuffs of claim 35, wherein A1 stands for the 2-methylsulfonyl-5-chloro-6-methylpyrimidinyl-4 radical. 47. A process for dyeing and printing hydroxyl-containing materials, in particular textile materials made from native or regenerated cellulose, characterized in that one or more dyes of claim 12 are applied to these materials in any order and, if appropriate, the material treated in this way is subjected to the action of elevated temperature. 48. A method for dyeing N-containing materials, preferably wool, silk, synthetic superpolyamide and -polt'-urethane fibers, characterized in that these materials are dyed with one or more dyes of claim 12 from acidic to neutral liquor and optionally then the pli range of the dyebath is increased, preferably to pH 6.5 to 85. 49. According to the method of claim: 47 colored or printed materials containing hydroxyl groups. 50. After the experience of painting 48 colored or di U crR11e N -haltge 1 '@ t Ottalieni 51;). Colorants containing a reactive dye of the formula where F is the radical of an organic dye, X4 is an amino group, Z is a halogen atom, Y is hydrogen or an optionally substituted alkyl substituent, R is an aliphatic, carbocyclic or heterocyclic substituent and m is a number from 0.5 to 8. 52) Colorants containing a reactive dye of the formula where F is the remainder of an azo, anthraquinone or phthalocyanine dye containing sulfonic acid groups, Z 'stands for Cl or Br and Y' stands for H or CH 3 and never means. their number, preferably a number from 1-2. 53) process for the preparation of reactive dyes, characterized in that dyes of the formula wherein F is the radical of an organic dye, 34 is an amino group, Z is a halogen atom, Y is hydrogen or an optionally substituted alkyl substituent, R is an aliphatic, carbocyclic or heterocyclic substituent and m is a number from 0.5 to 8, according to processes known per se condensation and / or Metallinierung and / or Dianotierung coupling and produces "54) method for the preparation of Reaktivfarbotoffen according to claim characterized in that one amino group-containing dyes or Parbetoffvorprodukte having a reactive hydrogen atom a® Aminetiekstoff, with compounds of the general - formula Y ... @ ° -SO R 1 @ 2 where Z denotes a halogen atom, Y denotes hydrogen or an optionally substituted alkyl group, Q denotes an anionically cleavable radical and R denotes an aliphatic, carbocyclic or heterocyclic substituent and, in the case of use of paraffin precursors, converts it into the desired end dyes in a suitable manner. 55) The method of claim 54, @ characterized in that as reactive components 2-methylsulfonyl-4,5-dichloropyrimidine, 2-Methyleulfonyl-4-chloro-5-bromopyrimidine, 2-methylsulfonyl-4,5-dichloro-6-methylpyrimidine , 2-methylsulfonyl-4-chloro-5-bromo-6-methylpyrimidine, 2,4-bis-methylsulfonyl-5-chloropyrimidine, 2,4-Hie-methylsulfonyl-5-chloro-6-methylpyrimidine, 2,4-bis -methyl- 8ulfonyl-5-bromo-6-methylpyrimidine, 2-benzenesulfonyl-4,5-dichloro-pyrimidine, 2-benzenesulfonyl-4,5-diehlor-6-methyl-pyrimidine or 2-Carbozymethylsulfonyl-4,5-dichloro-6 -methylpyrimidine used. 56) Process according to claims 53-55 », characterized in that , after the condensation, the dyes obtained are subjected to customary conversion reactions, in particular metallization, acylation, reduction and / or sulfonation reactions. 57). Process according to claim 6, characterized in that one uses aminoazo dyes of the formula wherein B and D aromatic carbocyclic or heterocycliache radicals, B may have in particular the radical of an enolic or phenoliechen coupling component, B, and D in the rest of any other Subetituenten, including azo groups, in particular a residue of a carbocycliechen diazo component of the benzene or Naphtalinreihe and D, R stands for a substituent or preferably hydrogen and m 'stands for an integer , preferably the number 1 or 2, with a compound of the formula where Q, Y, Z and R have the meaning given in Anepruch54, condensed. 58) Method according to Anepruch &, characterized in that one Aminoanthraquinone dyes of the formula wherein L is idasseratoft or a substituent, among serve in particular a sulphonic acid group, means p the number 1, 2 -or 3 and R a $ ubetituk --d ä @ ten or preferably water often means,. __. "le # connection of the horsmi wherein Q, Y, Z and R have the meaning given in claim 54, -reacted and, if appropriate, sulfated the dyes obtained in this way. 59) The method according to Anapruch54, characterized in that azaporphin dyestuffs of the formula _ vorin'Pc for the remainder of a phthalooymine, in particular a copper or W: L ckelphthaiooyaniar or your tetra- phenyl = kupter- or -niokel-phthalooyas., L stands for Hydrogen or a subatite, among these ins- special stands for a sultonic acid group, r is the number 1 or 2 , q is the number 0, 1 or 2 and R is a subititu- ducks or preferably hydrogen bedsulet and n "tnr is a number from 0.5 to 6, with connections of the Fo Aw el where Q, Y, Z and R are the values given in Anapruch54 have given meaning, _ condensed and optionally-the dyes thus obtained sulted. 60) method according to claim 53, characterized geke -.mz eichnet that one a slide or coupling component; the one group of the formula where R, Z and Y have the @ .nrsp-u: @ = rz -re: Yb @ rne meaning habon® by Iliamoting and / or converting domes to azo dyes. 61) Method according to claims 53 to 40, characterized in that that one builds up such axofarbatoffees or starting components used which have one or more sulfonic acid groups. 62) Reactive dyes of the formula wherein F is the remainder of an organic dye, 1-one Amino group, Z is a halogen atom, Y is hydrogen or a optionally substituted alkyl substituents, R is an aliphatic, carbocyclic or heterocyclic clic substituents and m is a number from 0.5 to 8 mean. 63) reactive dyes of the formula of claim 62, wherein f ' has one or more sulfonic acid groups. 64) Reactive azo dyes of the formula where B and D are aromatic carbocyclic or heterocyclic represent cal residues, B -preferably the remainder of a carbo- cyclic diazo component of the benzene or naphthalene series and D preferably denotes the remainder of an enolic or phenolic coupling component, B and D im remaining any further substituents, including others Azo groups, may have R1 for a substituent or preferably represents hydrogen, m 'is an integer, preferably represents the number 1 or 2, Z is a halogen atom, Y is hydrogen or an optionally substituted one Alkyl substituents and R is an aliphatic, carbo- mean cyclic or heterocyclic substituents. 65) Reactive anthraquinone dyes of the formula wherein Z is hydrogen or a substituent, among these are in particular a sulfonic acid group, p the Number 1, 2 or 3 denotes, R1 denotes a substituent or preferably represents hydrogen, s' is an integer, preferably represents the number 1 or 2, Z is a halogen atom, Z hydrogen or an optionally substituted one Alkyl substitutes and R is an aliphatic, carbo- cyclic or heterocyclic substituents mean. 66). Reactive azaporphin dyes of the formula where Pc is preferred for the remainder of a phthalocyanine a copper or nickel phthalocyanine or one ? etraphenrl-copper- or -nickel-phthaloeyanins stands, L «is hydrogen or a substituent among them in particular means a sulfonic acid group, r for Number 1 or 2 and q stand for the number 0, 1 or 2, R1 stands for a subatituent or, preferably, hydrogen Z is a halogen atom, Y is hydrogen or a ne- optionally substituted alkyl substituents and R an aliphatic, carbocycliachen or heteroeyoli- acnen mean substituents and m '' for a number of 0.5 to 4 stands. 4?) Dyestuffs of claim 64, _ wherein H and / or D is one or have several sulfonic acid groups. 68) Parbattoffe of claim 65, which one or more sulfone have acid groups. 69) Parbatoffe of claim 66, which one or more sulfonic acid Have soups. Beaktivfarbenatoffe of the formula Ys .._ & B, - $ 02CH3 where T 'contains the remainder of a sulfonic acid group containing Aso-, Represents anthraquinone or phthalocyanine dye, Z 'is C1 or Br, Y is hydrogen or CH 3 represents and a 'stands for a number ton 1-2 . 71. Process for dyeing and printing hydroxyl groups containing materials, in particular textile materials native or regenerated cellulose, characterized in that that one can access these materials in any order or more dyes of claim 33 applies and ge if necessary, the material treated in this way is subject to high temperature. 72. A process for dyeing nitrogen-containing materials, preferably of wool, silk, synthetic Superpolyamid- and -polt'-urethane fibers, characterized in that one da3 these materials with one or more dyes of claim 33 from acidic to neutral colors and fleet if necessary , the pH range of the dyebath is then increased, preferably to pH 6.5 to 8.5. 73. Materials containing hydroxyl groups colored or printed according to the method of claim 71. 74. According to the method of claim 72 colored or printed N-containing materials. 75. Process for printing and printing hydroxyl-containing groups Materials, especially textile materials made from native or regenerated C # llulose, characterized in that one on Serve materials in any @eihA - 'lge one or more Proof of claim 62 and, if applicable, that 1d treated "^ material of the action of elevated temperature - subject. 76. A process for dyeing nitrogen-containing materials forthcoming, Trains t of wool, silk, synthetic Superpolyamid- and -polyurethanfasern, characterized in that these materials entitlement with one or more dyes of the check 62 from acid dyes and to a neutral fleet gege - In addition, the pH range of the dyebath is then increased, preferably to pH 6.5 to 8.5. 77. Bxw colored according to the method of claims 76 and 77. printed materials.