Water-soluble disazo compounds, which can be used as fiber reactive dyestuffs and correspond to the general formula ##STR1## in which Y is vinyl or --CH.sub.2 --CH.sub.2 --Z, Z being sulfato, phosphato, halogen or hydroxy; PA1 D is phenylene or phenylene substituted by 1 or 2 radicals selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, chlorine, bromine, fluorine, carboxy, nitro and sulfo, or PA1 D is naphthylene or naphthylene substituted by 1 or 2 radicals selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, chlorine, bromine, fluorine, carboxy and sulfo; PA1 E is 1,4-phenylene or 1,4-naphthylene, or 1,4-phenylene or 1,4-naphthylene substituted by 1 or 2 radicals selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, ureido, lower alkanoylamino, chlorine, bromine, carboxy and sulfo; PA1 A is ethylene of the formula --CH.sub.2 --CH.sub.2--, or ethyleneoxy of the formula--CH.sub.2 --CH.sub.2 --O--, or propylene of the formula --CH.sub.2 --CH.sub.2 --CH.sub.2 --, or is of the formula ##STR2## wherein X is hydroxy, lower alkanoylamino, halogen, sulfato or phosphato, or is ##STR3## M is hydrogen, a metal or the equivalent of a metal; R.sup.1 is hydrogen, lower alkyl, lower alkenyl or lower alkyl substituted by hydroxy or phenyl or by both, or is alkyl of from 2 to 4 carbon atoms substituted by acetoxy, propionyloxy or phenylsulfonyloxy, or is cyanoalkyl of from 2 to 4 carbon atoms in the alkyl, or is carboxyalkylene, carbonamidoalkylene or carbalkoxyalkylene, the alkyl or aklylene moiety being in each case of from 1 to 4 carbon atoms, or is halogenoethyl or a group of the formula --A--SO.sub.3 M, A and M being as defined above; PA1 R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halogen, lower alkanoylamino, ureido or trifluoromethyl; and PA1 R.sup.3 is hydrogen, lower alkyl, lower alkoxy or halogen. These disazo compounds can be prepared in a manner which is in itself known by reacting the diazo and coupling components which are evident from the formula (1). They serve as dyestuffs for dyeing and printing fibers which contain hydroxyl and/or cabonamide groups, such as cellulose fibers, wool or synthetic polyamide fibers, or leathers.

The present invention is in the industrial field of the water-soluble 
disazo dyestuffs which have fiber-reactive properties. It relates to new 
water-soluble disazo compounds of the general formula (1) 
##STR4## 
in which Y is the vinyl group or a group of the formula --CH.sub.2 
--CH.sub.2 --Z, in which Z denotes an organic or inorganic radical which 
can be eliminated under alkaline conditions, or the hydroxy group, n 
represents the number zero, 1 or 2, D is a phenylene unsubstituted or 
substituted by 1 or 2 substituents selected from a group consisting of 
lower alkyl, lower alkoxy, hydroxy, lower alkanoylamino, benzoylamino, 
chlorine, bromine, fluorine and carboxy, and/or by one nitro group and/or 
by one sulfo group, or D is a naphthylene unsubstituted or substituted by 
1 or 2 substituents selected from a group consisting of lower alkyl, lower 
alkoxy, hydroxy, lower alkanoylamino, benzoylamino, chlorine, bromine, 
fluorine, carboxy and sulfo, and/or by one nitro group, or D is the 
benzthiazol-2-yl radical which contains the indicated group of the formula 
Y--SO.sub.2 --(CH.sub.2).sub.n -- bonded in the carbocyclic ring and which 
can be further substituted in this benzene nucleus by a substituent from 
the group comprising lower alkyl, lower alkoxy, hydroxy, lower 
alkanoylamino, benzoylamino, nitro, chlorine, bromine and sulfo, E is the 
1,4-phenylene radical or the 1,4-naphthylene radical, both of which can be 
monosubstituted or disubstituted by substituents from the group comprising 
lower alkyl, lower alkoxy, hydroxy, ureido, lower alkanoylamino, 
benzoylamino, benzenesulfonylamino, benzoylamino which is substituted by 
lower alkyl, lower alkoxy, chlorine and/or sulfo, benzenesulfonylamino 
which is substituted by lower alkyl, lower alkoxy, chlorine and/or sulfo, 
chlorine, bromine, carboxy and sulfo, A is the ethylene radical of the 
formula --CH.sub.2 --CH.sub.2 -- or the ethyleneoxy radical of the formula 
--CH.sub.2 --CH.sub.2 --O-- or a propylene radical of the formula 
--CH.sub.2 --CH.sub.2 --CH.sub.2 --, 
##STR5## 
wherein X represents the hydroxy group or an acyloxy group of a lower 
alkanecarboxylic acid, for example the acetoxy group or propionyloxy 
group, or a halogen atom, preferably a chlorine atom or bromine atom, or 
the sulfato group or the phosphato group, or is a radical of the formula 
##STR6## 
M is a hydrogen atom or the equivalent of a metal, preferably of an alkali 
metal or of an alkaline earth metal, such as in particular of sodium, 
potassium or calcium, R.sup.1 is a hydrogen atom, a lower alkyl group, a 
lower alkenyl group or a lower alkyl group which is substituted by phenyl 
and/or hydroxy, it being possible for the phenyl radical to be substituted 
by methyl, methoxy and/or chlorine, such as in particular the benzyl group 
or phenethyl group, and a hydroxyalkyl group having 2 to 4 C atoms, or is 
an acid-esterified hydroxyalkyl group having 2 to 4 C atoms in this alkyl 
radical, such as, for example, an acetoxyalkyl, propionyloxyalkyl or 
phenylsulfonyloxyalkyl, or is a cyanoalkyl group having 2 to 4 C atoms in 
the alkyl radical, a carboxy-, carbonamido- or carbalkoxyalkylene group 
having in each case 1 to 4 C atoms in the alkyl or alkylene radical, a 
halogenoalkyl group having 2 or 3 C atoms, preferably a chloroalkyl group, 
or a lower halogenoalkenyl group in which the halogen is preferably 
chlorine or bromine, or is a group of the formula --A--SO.sub.3 M defined 
above, R.sup.2 is a hydrogen, lower alkyl, of which methyl is preferred, 
or lower alkoxy unsubstituted or substituted by hydroxy, acetoxy, carboxy, 
carbonamide, cyano or halogen, such as chlorine and bromine, or is 
halogen, such as chlorine, bromine or fluorine, lower alkanoylamino, such 
as acetylamino, or benzoylamino or an ureido or a trifluoromethyl group, 
and R.sup.3 is a hydrogen atom, a lower alkyl group, of which a methyl 
group is preferred, or a lower alkoxy group, which can be substituted by 
hydroxy, acetoxy, carboxy, carbonamide, cyano or halogen, such as chlorine 
or bromine, or is a halogen atom, such as a chlorine atom, bromine atom or 
fluorine atom. 
The formula moieties R.sup.2 and R.sup.3 can have identical or different 
meanings. 
The terms "lower" denote here, as below, that the alkyl, alkylene or 
alkenyl radical contained in the group has 1 to 6 or 2 to 6 C atoms, 
preferably 1 to 4 or 2 to 4 C atoms. 
Examples of the groups Z which can be eliminated under alkaline conditions 
are halogen atoms, such as a chlorine atom, bromine atom or fluorine atom, 
ester groups of organic carboxylic and sulfonic acids, such as a lower 
alkanoyloxy radical, for example the acetoxy radical, or an acyloxy 
radical of an aromatic carboxylic or sulfonic acid, such as the 
benzoyloxy, sulfobenzoyloxy, benzenesulfonyloxy or toluenesulfonyloxy 
radical, and also the lower alkylsulfonylamino and arylsulfonylamino 
groups, the phenoxy group, dialkylamino groups having alkyl groups of 1 to 
4 C atoms each, such as the dimethylamino or diethylamino group, and also 
monoester groups, for example of thiosulfuric acid, of phosphoric acid and 
in particular of sulfuric acid. 
The new disazo compounds can be present in the acid form as well as in the 
form of their salts. They are preferably in the form of salts, in 
particular salts of alkali metals and alkaline earth metals, and, amongst 
these, in particular, as sodium salts, potassium salts and also calcium 
salts. They can be used, preferably in the form of these salts, as 
dyestuffs for dyeing and printing fibers which contain hydroxy and/or 
carbonamide groups, or leathers. 
The present invention also relates to a process for the preparation of the 
abovementioned and defined disazo compounds of the general formula (1). 
This process comprises diazotizing a compound of the general formula (2) 
EQU Y--SO.sub.2 --(CH.sub.2).sub.n --D--N.dbd.N--E--NH.sub.2 ( 2) 
in which D, E, Y and n have the abovementioned meanings, in a manner which 
is in itself known and coupling the reaction product with a coupling 
component of the general formula (3) 
##STR7## 
in which M, A, R.sup.1, R.sup.2 and R.sup.3 have the abovementioned 
meanings, to give a disazo compound of the general formula (1) and, if Y 
represents the .beta.-hydroxyethyl group, converting this disazo compound 
having the .beta.-hydroxyethyl group with the aid of a sulfating agent 
into the corresponding disazo compound of the general formula (1), in 
which Y represents the .beta.-sulfatoethyl group, or with the aid of a 
phosphating agent into the corresponding compound of the general formula 
(1), in which Y represents the .beta.-phosphatoethyl group. 
Examples of suitable sulfating agents are 90 to 100% strength sulfuric 
acid, chlorosulfonic acid, amidosulfonic acid or other compounds which 
release sulfur trioxide. Examples of suitable phosphating agents are 
concentrated phosphoric acid, pyrophosphoric acid, metaphosphoric acid or 
polyphosphoric acid, and also polyphosphoric acid alkyl esters, phosphorus 
oxychloride or mixtures of phosphoric acid and phosphorus(V) oxide. 
Aminoazo compounds of the general formula (2) can be prepared in a way 
which is in itself known by coupling a diazotized amine of the general 
formula (4) 
EQU Y--SO.sub.2 --(CH.sub.2).sub.n --D--NH.sub.2 ( 4) 
in which D, Y and n have the abovementioned meanings, with a compound 
capable of coupling of the general formula (5) 
EQU H--E--NH.sub.2 ( 5) 
in which E has the abovementioned meaning. The further reaction according 
to the invention (diazotizing and coupling) of this aminoazo compound of 
the general formula (2) to give a disazo compound of the general formula 
(1) can be carried out without an intermediate isolating stage after the 
preparation of the former; for example, this further reaction can be 
carried out in accordance with the invention in the same reaction batch. 
Examples of aromatic amines of the general formula (4), which serve as 
diazo components in the preparation of the compounds according to the 
invention, are in particular the following: 
4-.beta.-sulfatoethylsulfonylaniline, 
4-.beta.-chloroethylsulfonyl-aniline, 4-.beta.-phosphatoethylsulfonyl-anil 
ine, 4-vinylsulfonyl-aniline, 4-.beta.-thiosulfatoethylsulfonyl-aniline, 
2-sulfo-4-.beta.-sulfatoethylsulfonyl-aniline, 
2-bromo-4-.beta.-sulfatoethylsulfonyl-aniline, 
2-chloro-4-.beta.-sulfatoethylsulfonyl-aniline, 
2-chloro-5-.beta.-chloroethylsulfonyl-aniline, 
3-.beta.-sulfatoethylsulfonyl-aniline, 
2-bromo-5-.beta.-sulfatoethylsulfonyl-aniline, 
2,6-dichloro-4-.beta.-sulfatoethylsulfonyl-aniline, 
2,6-dibromo-4-.beta.-sulfatoethylsulfonyl-aniline, 
2,5-dichloro-4-.beta.-sulfatoethylsulfonyl-aniline, 
2-methyl-5-.beta.-sulfatoethylsulfonyl-aniline, 
2-methoxy-5-.beta.-sulfatoethylsulfonyl-aniline, 
2-methoxy-4-.beta.-sulfatoethylsulfonyl-aniline, 
2-methyl-6-chloro-4-.beta.-sulfatoethylsulfonyl-aniline, 
2,6-dimethyl-4-.beta.-sulfatoethylsulfonyl-aniline, 
2,6-dimethyl-3-.beta.-sulfatoethylsulfonyl-aniline, 
2,5-dimethoxy-4-.beta.-sulfatoethylsulfonyl-aniline, 
2-methoxy-5-methyl-4-.beta.-sulfatoethylsulfonyl-aniline, 
2-nitro-4-.beta.-sulfatoethylsulfonyl-aniline, 
4-nitro-2-.beta.-sulfatoethylsulfonyl-aniline, 
6-.beta.-sulfatoethylsulfonyl-2-naphthyl-amine, 
1-sulfo-6-.beta.-sulfatoethylsulfonyl-2-naphthylamine, 
8-.beta.-sulfatoethylsulfonyl-2-naphthylamine, 
6-sulfo-8-.beta.-sulfatoethylsulfonyl-2-naphthylamine, 
6-vinylsulfonyl-2-aminobenzthiazole, 
6-.beta.-sulfatoethylsulfonyl-2-aminobenzthiazole, 
4-.omega.-(.beta.-sulfatoethylsulfonyl)-tolylamine, 
3-.omega.-(.beta.-sulfatoethylsulfonyl)-tolylamine, 
6-methoxy-3-.omega.-(.beta.-sulfatoethylsulfonyl)-tolylamine, 
4-methoxy-3-.omega.-(.beta.-sulfatoethylsulfonyl)-tolylamine, 
4-.omega.-(.beta.-sulfatoethylsulfonyl)-ethyl-aniline, 
3-.omega.-(.beta.-sulfatoethylsulfonyl)-ethyl-aniline, 
5-(.beta.-sulfatoethylsulfonyl-methyl)-1-naphthylamine and their 
.beta.-hydroxyethylsulfonyl derivatives. 
Compounds of the formula (4) are known and can be prepared by methods which 
have been extensively described in the literature. For example, the 
preferred compounds of the formula (4) having a 
.beta.-sulfatoethylsulfonyl group are obtained from the corresponding 
.beta.-hydroxyethylsulfonyl compounds by esterification, for example by 
means of aqueous or concentrated sulfuric acid or by means of 
amidosulfonic acid, such as, for example, by adding the corresponding 
.beta.-hydroxethylsulfonyl-anilines and 
.beta.-hydroxyethylsulfonyl-naphthylamines to an equimolar amount of 60% 
strength sulfuric acid and subsequent heating in a manner analogous to the 
process described in German Patent Specification No. 1,150,163, or, for 
example by dissolving .beta.-hydroxyethylsulfonylanilines or 
.beta.-hydroxyethylsulfonylnaphthylamines in excess concentrated sulfuric 
acid or 100% strength sulfuric acid (monohydrate) at room temperature or 
by reacting them with amidosulfonic acid in the presence of pyridine or a 
pyridine base in a manner analogous to the esterification process 
described in German Patent Specification No. 1,443,877. 
.beta.-Sulfatoethylsulfonyl-anilines and 
.beta.-sulfatoethylsulfonyl-naphthylamines thus prepared can also be used 
in the process according to the invention in an unisolated form in the 
form of the reaction mixture obtained from the esterification. 
Aromatic amines of the general formula (5), which serve as coupling 
components in the preparation of the aminoazo compounds of the general 
formula (2), are also generally known. Amongst these the following are to 
be mentioned as preferable: aniline, o-toluidine, m-toluidine, 
o-anisidine, m-anisidine, anthranilic acid, cresidine, 2,5-xylidine, 
2,5-dimethoxy-aniline, 3-aminoacetanilide, 
3-amino-acetanilide-4-carboxylic acid, 3-amino-acetanilide-4-sulfonic 
acid, 3-aminophenylurea, 3-aminophenylurea-4-sulfonic acid, 
1-naphthylamine-6-sulfonic acid, 1-naphthylamine-7-sulfonic acid and 
2-ethoxy-1-naphthylamine-6-sulfonic acid. The formula member R.sup.1 is 
preferably hydrogen or alkyl of 2 to 4 C-atoms unsubstituted or 
substituted by phenyl, hydroxy, acetyloxy, propionyloxy, cyano, carbamoyl 
or chlorine, or is a group of the formula --A--SO.sub.3 M defined above. 
When R.sup.1 is chloroalkyl, the alkyl group is especially preferred one 
of 2 or 3 C-atoms.-The formula member R.sup.2 is preferably hydrogen, 
methyl, ethyl, methoxy, ethoxy, or methoxy or ethoxy substituted by 
hydroxy, acetyloxy, carboxy, carbamoyl, cyano or chlorine, or is chlorine 
or bromine. If R.sup.2 is a halogen, chlorine is the preferred one.-The 
formula member R.sup.3 is preferably hydrogen, methyl, ethyl, methoxy, 
ethoxy, or methoxy or ethoxy substituted by hydroxy, acetyloxy, carboxy, 
carbamoyl, cyano or chlorine, or is bromine or chlorine. If R.sup.3 is a 
halogen, chlorine is the preferred one. 
Those compounds according to the invention of the general formula (1) are 
preferred for which the formula moiety D denotes the 1,4-phenylene radical 
or the 1,4-naphthylene radical, both of which can be monosubstituted or 
disubstituted by substituents from the group comprising methyl, methoxy, 
hydroxy, chlorine, bromine, carboxy and sulfo. 
Those compounds according to the invention of the general formula (1) are 
also preferred in which E denotes the 1,4-phenylene radical, which can be 
substituted by 1 or 2 lower alkyl groups, such as in particular methyl or 
ethyl, or by one or two lower alkoxy groups, such as in particular methoxy 
and ethoxy, or by one carboxy group or by a lower alkanoylamino group, 
such as the acetylamino or propionylamino group, or by a ureido group or 
by a lower alkanoylamino group and a sulfo group or by a ureido group and 
a sulfo group, or in which E denotes the 1,4-naphthylene radical, which is 
substituted by a sulfo group or by a lower alkoxy group, such as, for 
example, the methoxy group and in particular the ethoxy group, and a sulfo 
group. 
The sulfoalkylanilines of the general formula (3) which are used as 
coupling components in the synthesis of the compounds of the general 
formula (1) can be prepared by a known method, thus, for example, by the 
procedures disclosed in German Offenlegungsschriften Nos. 1,481,831 and 
1,493,636 and also by the methods described in R. B. Wagner and H. D. 
Zock, Synthetic Organic Chemistry, John Wiley and Sons, Inc., New York, 
1953, pages 812-819, and also by reacting .alpha.,.alpha.'-dichlorohydrin 
with sodium sulfite in accordance with German Patent Specification No. 
258,473 and condensing this reaction product with an aromatic amine, such 
as, for example, according to the reaction equation 
##STR8## 
or by reacting propanesultone with aromatic amines. 
.beta.-Sulfoethylaniline derivatives can be prepared by reacting 
.beta.-chloroethanesulfonic acid or its salts with aromatic amines, for 
example by the method described by J. W. James in Journ. prakt. chem. 
[2]31, 413 (1885). It can also be prepared in a very high degree of 
purity, for example by the addition of vinylsulfonylfluoride to aniline 
derivatives and subsequent alkaline hydrolysis of the sulfofluoride group. 
The coupling components of the formula (3), which contain a 
.beta.-sulfatoethylamino group, can, for example, be prepared by the 
methods described by K. H. Saunders, J. Chem. Soc. (London) 121, 2667-2675 
(1922). They can also be prepared by esterifying their 
.beta.-hydroxyethyl-aniline derivatives, for example by reacting them with 
sulfuric acid, either in 100% strength sulfuric acid in the presence of 
chlorosulfonic acid or in oleum (i.e. sulfuric acid containing sulfur 
trioxide). Coupling components of the formula (3) this esterified can also 
be used in the process according to the invention in an unisolated form, 
i.e. in the form of the reaction mixture resulting from the 
esterification. 
Examples of compounds of the general formula (3), which serve as coupling 
components in the preparation of compounds according to the invention are: 
N-.beta.-sulfoethylaniline, N-.beta.-sulfoethyl-2-chloroaniline, 
N-.beta.-sulfoethyl-3-chloroaniline, N-.beta.-sulfoethyl-2-methylaniline, 
N-.beta.-sulfoethyl-2-methoxyaniline, 
N-.beta.-sulfoethyl-2-methyl-5-chloroaniline, 
N-.beta.-sulfoethyl-2-methoxy-5-chloroaniline, 
N-.beta.-sulfoethyl-2-chloro-5-methoxyaniline, 
N-.beta.-sulfoethyl-2,5-dichloroaniline, 
N-.beta.-sulfoethyl-N-methyl-aniline, N-.beta.-sulfoethyl-N-ethyl-aniline, 
N-.beta.-sulfoethyl-N-ethyl-3-methyl-aniline, 
N-.beta.-sulfoethyl-N-ethyl-3-chloroaniline, 
N-.beta.-sulfoethyl-N-allyl-aniline, N-.beta.-sulfoethyl-N-benzylaniline, 
N-.beta.-sulfoethyl-N-phenethyl-aniline, 
N-.beta.-sulfoethyl-N-.beta.-carbonamidoethyl-aniline, 
N-.beta.-sulfoethyl-N-.beta.-carboxyethyl-aniline, 
N-.beta.-sulfoethyl-N-.beta.-cyanoethyl-aniline, 
N-.beta.-sulfoethyl-N-.beta.-acetoxyethyl-aniline, 
N-.beta.-sulfoethyl-N-.beta.-hydroxyethyl-aniline, 
N-.beta.-sulfoethyl-N-ethyl-2-methoxy-5-chloro-aniline, 
N-.beta.-sulfoethyl-N-.beta.-hydroxyethyl-2-methoxy-5-chloro-aniline, 
N-.beta.-sulfoethyl-N-.beta.-hydroxyethyl-3-chloroaniline, 
N-.beta.-sulfoethyl-N-.beta.-carboxyethyl-3-chloroaniline, 
N,N-bis-(.beta.-sulfoethyl)-aniline, 
N,N-bis-(.beta.-sulfoethyl)-3-methyl-aniline, 
N,N-bis-(.beta.-sulfoethyl)-3-chloroaniline, 
N-.gamma.-sulfopropyl-aniline, N-.gamma.-sulfopropyl-3-chloraniline, 
N-.gamma.-sulfopropyl-2-methyl-5-chloroaniline, 
N-(.gamma.-sulfo-.beta.-hydroxypropyl)-2-methoxy-5-chloroaniline, 
N-(.gamma.-sulfo-.beta.-hydroxypropyl)-2-chloroaniline, 
N-(.gamma.-sulfo-.beta.-hydroxypropyl)-2,5-dichloroaniline, 
N-(.gamma.-sulfo-.beta.-hydroxypropyl)-N-ethylaniline, 
N-(.gamma.-sulfo-.beta.-sulfatopropyl)-N-ethyl-3-methylaniline, 
N-(.gamma.-sulfo-.beta.-sulfatopropyl)-N-.beta.-sulfatoethyl-aniline, 
N-(.gamma.-sulfo-.beta.-hydroxypropyl)-N-phenethyl-aniline, 
N-(.gamma.-sulfo-.beta.-hydroxpropyl)-N-(.beta.-hydroxyethyl)-2-methoxy-5- 
chloroaniline, N-(.gamma.-sulfo-.beta.-hydroxypropyl)-aniline, 
N-(.gamma.-sulfo-.beta.-hydroxypropyl)-2-chloro-3-methyl-aniline, 
N-(.gamma.-sulfopropyl)-N-ethyl-3-methylaniline, 
N-(.gamma.-sulfo-.beta.-hydroxypropyl)-N-.beta.-carboxyethyl-3-chloroanili 
ne, N-(.beta.-sulfo-.alpha.-methyl-ethyl)-aniline, 
N-(.beta.-sulfo-.alpha.-methyl-ethyl)-2-methoxy-5-chloroaniline, 
N,N-bis-(.gamma.-sulfo-.beta.-hydroxypropyl)-3-chloroaniline, 
N-(.gamma.-sulfopropyl)-2,5-dichloroaniline, 
N-.beta.-sulfatoethyl-aniline, N-.beta.-sulfatoethyl-N-ethyl-aniline, 
N-.beta.-sulfatoethyl-N-methyl-aniline, 
N-.beta.-sulfatoethyl-N-n-butyl-aniline, 
N-.beta.-sulfatoethyl-N-ethyl-3-methyl-aniline, 
N-.beta.-sulfatoethyl-N-ethyl-3-chloro-aniline, 
N-.beta.-sulfatoethyl-N-.beta.-hydroxyethyl-3-chloroaniline, 
N,N-di-.beta.-sulfatoethyl-aniline, 
N,N-di-.beta.-sulfatoethyl-3-chloro-aniline, 
N-.beta.-sulfatoethyl-N-2-bromoallyl-aniline, 
N-.beta.-sulfatoethyl-N-2-chloroallyl-aniline, 
N-.beta.-sulfatoethyl-N-benzyl-aniline, 
N-.beta.-sulfatoethyl-N-.beta.-carbonamidoethyl-aniline, 
N-.beta.-sulfatoethyl-N-.beta.-carboxyethyl-aniline, 
N-(4'-sulfophenethyl)-aniline, 
N-(.beta.-cyanoethyl)-N-(4'-sulfophenethyl)-aniline, 
N-.beta.-sulfatoethyl-N-.beta.-carbethoxyethyl-aniline, 
N-.beta.-sulfatoethyl-N-.beta.-cyanoethyl-aniline, 
N-.beta.-sulfatoethyl-N-.beta.-acetoxyethyl-aniline, 
N-.beta.-sulfatoethyl-N-.beta.-cyanoethyl-3-methyl-aniline and 
N-.beta.-sulfatoethyl-N-.beta.-hydroxyethyl-aniline. 
Diazotizing amines of the general formulae (2) or (4) can be effected by 
generally known methods, for example by reaction with an alkali metal 
nitrite and an inorganic acid, such as hydrochloric aid, sulfuric acid or 
phosphoric acid, or by reaction with nitrosylsulfuric acid. 
The coupling reaction with the coupling components of the general formulae 
(3) or (5) can also be carried out in a way which is in itself known in a 
neutral to acid medium, preferably in a pH range between 1 and 7 and at a 
temperature between -5.degree. C. and +25.degree. C., if appropriate in 
the presence of sodium acetate or the like, of buffer substances which 
influence the coupling rate or of catalysts, such as, for example, 
dimethylformamide or pyridine. 
Compounds of the formula (1), prepared according to the invention, can be 
separated from the reaction solution by salting out by means of 
electrolytes, for example sodium chloride or potassium chloride, 
advantageously after adjusting the pH of the reaction mixture to 3.5 to 
7.0; after filtration they are dried. The compounds according to the 
invention can also be isolated from their synthesis batches by evaporating 
or spray-drying. In cases, in which relatively large quantities of sulfate 
ions are present in the reaction solution obtained, it is advisable to 
precipitate the sulfate ions in the form of sparingly soluble salts, for 
example as calcium sulfate, prior to the spray-drying. It is also possible 
to use the solutions of the compound of the formula (1), which are 
obtained after the synthesis, directly as a liquid formulation as used in 
dyeing, if appropriate after a buffer substance has been added. 
The new compounds of the formula (1) are suitable as dyestuffs, in 
particular as fiber-reactive dyestuffs; they are preferably applied and 
fast-fixed, by the application processes known for reactive dyestuffs, to 
the substrates mentioned below. 
The present invention therefore also relates to the use of compounds of the 
formula (1) as dyestuffs, in particular for dyeing and printing cellulose 
fibers and natural or synthetic polyamide fibers or leathers, and to a 
process for dyeing and printing cellulose fiber materials or natural or 
synthetic polyamide fiber materials or leather, using compounds of the 
formula (1). Cotton and regenerated cellulose, such as viscose rayon, and 
also linen, hemp and jute are preferred as the cellulose fiber materials. 
In particular wool and other animal fibers and also silk, and in 
particular polyamide 6,6, polyamide 6, polyamide 11 or polyamide 4, of the 
synthetic polyamides, are suitable polyamide fiber materials. 
For example, dyeings having a very good color yield are obtained when the 
disazo compounds according to the invention are applied to cellulose 
fibers by the exhaust method, from dyebaths at long liquor ratio and using 
the most diverse additions of alkali. Likewise, excellent color yields are 
obtained on cellulose when using the known padding methods, it being 
possible to fix the compound of the formula (1) by means of alkali by 
leaving the dyeings to stand at room temperature, by steaming, or by using 
dry heat. In printing, the customary one-step methods may be used, such as 
employing an acid-binding agent or alkali-donating agent, such as, for 
example, sodium bicarbonate sodium carbonate or sodium trichloroacetate, 
in the printing paste with subsequent fixing by steaming, for example at 
100.degree.-103.degree. C., or the two-step methods in neutral or slightly 
acid printing pastes are used and the printed fiber material is either 
passed through a hot alkaline bath containing an electrolyte, or 
overpadded with an alkaline padding liquor containing an electrolyte and 
thereafter treated with steam or dry heat, for fixation of the compound of 
the formula (1). These processes produce intense prints having 
well-delineated contours and a clear white ground. The quality of the 
prints depends only to a small extent on differing conditions of fixing, 
and the prints thus have a satisfactory shade reproducibility. 
The fastness properties, on cellulose fiber material, of the dyeings or 
prints which can be obtained with the compounds of the formula (1) are 
impressive; of these particular mention should be made of the most 
important manufacturing and end-use fastness properties, such as 
light-fastness, wash-fastness, for example at 60.degree. C. or 95.degree. 
C., fastness to acid and alkaline milling, water-fastness, 
seawater-fastness, fastness to acid cross-dyeing, fastness to alkaline and 
acid perspiration and also fastness to pleating, ironing and rubbing. 
Not only the natural but also the synthetic polyamide fiber materials are 
dyed with the new compounds of the formula (1), preferably from an acid 
aqueous dyebath or acid aqueous dye liquor. The desired pH value of the 
dyebath or the dye liquor is preferably adjusted with acetic acid or 
acetic acid and ammonium acetate or sodium acetate. In order to achieve an 
acceptable levelness of the dyeings, or to improve their levelness, it is 
advantageous also to use, in the dyebath or dye liquor, customary leveling 
agents, for example compounds based on a product from the reaction of a 
fatty amine, such as, for example, stearylamine, with an alkylene oxide, 
such as ethylene oxide, and/or a product from the reaction of cyanuric 
chloride with an approximately three-fold molar amount of an 
aminobenzenesulfonic acid and/or an aminonaphthalenesulfonic acid. The 
dyeings can usually be carried out at a temperature of 
60.degree.-105.degree. C., preferably in an exhaust process, in particular 
at the boiling point of the dyebath, or in a pressure dyeing apparatus at 
a temperature up to 120.degree. C.

The examples below serve to illustrate the invention. Unless otherwise 
indicated, the parts mentioned therein are parts by weight and the values 
in percent represent percentages by weight. Parts by volume relate to 
parts by weight as the liter relates to the kilogram. 
EXAMPLE 1 
36.1 parts of 4-.beta.-sulfatoethylsulfonyl-aniline-2-sulfonic acid are 
dissolved with stirring in 200 parts of warm water by adding sodium 
bicarbonate; 20 parts by volume of an aqueous 5 N sodium nitrite solution 
are added and the whole batch is poured onto 200 parts of ice. 35 parts of 
31% strength aqueous hydrochloric acid are then allowed to run slowly into 
the mixture, while stirring; stirring is then continued for another 30 
minutes at about 5.degree. C. Excess nitrous acid is destroyed with a 
little amidosulfonic acid. An acid solution of 10.7 parts of 
3-methylaniline in 60 parts of water is added to this diazonium salt 
solution and the coupling reaction is initially carried out in a strongly 
acid range, which is later changed to a pH range of 3 to 3.5 by means of 
the gradual addition of sodium bicarbonate. After coupling is complete, 
the pH value is adjusted to 6.5 by adding sodium bicarbonate, 20 parts by 
volume of an aqueous 5 N sodium nitrite solution are then added and the 
mixture is slowly poured onto a mixture of 300 parts of ice and 35 parts 
of 31% strength hydrochloric acid. After this diazotizing mixture has been 
stirred for 2 to 3 hours at about 5.degree. C., excess nitrous acid is 
destroyed with a little amidosulfonic acid. A solution of 41.9 parts of 
the disodium salt of N,N-bis-(.beta.-sulfatoethyl)-3-chloroaniline in 150 
parts of water is added to the mixture and the coupling reaction is first 
carried out in a strongly acid range, which is then changed to a pH value 
of about 4 to 5 by means of the addition of sodium bicarbonate. After the 
coupling is complete, the pH of the mixture is adjusted to 5.5 to 6 and 
the prepared disazo compound according to the invention is isolated either 
by salting out with sodium chloride or by spray-drying. 
A dark brown powder is obtained which in addition to electrolyte contains 
the sodium salt of the compound of the formula 
##STR9## 
The compound has very good dyestuff properties and produces very intense 
yellowish brown dyeings and prints having a very good resistance towards 
washing treatments on the fiber materials mentioned in the descriptive 
section, such as, for example, cotton and wool, by application and fixing 
methods customary and known for fiber-reactive dyestuffs. 
EXAMPLES 2 TO 13 
In order to prepare a disazo compound according to the invention the 
procedure of Example 1 is followed, but here the disodium salt of 
N,N-bis-(.beta.-sulfatoethyl)-3-chloroaniline, which serves as a coupling 
component, is replaced by an equivalent amount of the coupling components, 
corresponding to the general formula (3), which are indicated in the 
examples in the tables which follow. The disazo compound according to the 
invention which is also indicated and corresponds to the general formula 
(1), is likewise obtained in good yield. These fiber-reactive disazo 
compounds according to the invention likewise have very good dyestuff 
properties with very good application properties; they produce dyeings and 
prints which have good to very good fastness properties and the shade 
given in the particular example in the table, on the fiber materials 
mentioned in the descriptive section, in particular on cellulose fiber 
materials and wool, by the application and fixing methods customary for 
fiber-reactive dyestuffs. 
The formula moiety M in the compounds which have been indicated by means of 
a formula, has the above-mentioned meaning; it preferably represents an 
alkali metal, in particular sodium. The formula radical D.sub.1 indicated 
for the compound according to the invention represents a radical of the 
formula 
##STR10## 
with M having the above-mentioned meaning. 
__________________________________________________________________________ 
Coupling component 
Disazo compound corres- 
Shade 
Ex- corresponding to the 
ponding to the general 
on 
ample 
general formula (3) 
formula (1) cotton 
__________________________________________________________________________ 
2 3-Chloro-N(.beta.-sulfo- ethyl)-aniline 
##STR11## yellowish red 
3 3-Methyl-Nethyl- N(.beta.-sulfoethyl)- aniline 
##STR12## violet 
4 3-Chloro-N,Nbis- (.beta.-sulfoethyl)- aniline 
##STR13## yellowish brown 
5 N,NBis-(.beta.-sulfo- ethyl)-aniline 
##STR14## brown 
6 3-Chloro-6-methoxy- Nethyl-N (.beta.-sulfo- ethyl)-aniline 
##STR15## bluish- tinged bluish red 
7 3-Methyl-Nethyl-N (.beta.-sulfato-.gamma.-sulfo- n-propyl)-aniline 
##STR16## bluish- tinged bluish red 
8 NEthyl-N(3'-sulfo- benzyl)-aniline 
##STR17## bluish- tinged bluish red 
9 3-Chloro-6-methyl-N (.beta.-sulfoethyl)- aniline 
##STR18## brown 
10 3-Methyl-N,Nbis-(.beta.- sulfatoethyl)-aniline 
##STR19## violet 
11 N(.beta.-Cyanoethyl)-N (.beta.-sulfatoethyl)- aniline 
##STR20## reddish brown 
12 N(.beta.-Sulfoethyl)- aniline 
##STR21## yellowish brown 
13 N(.beta.-Hydroxy-.gamma.- sulfo-n-propyl)- aniline 
##STR22## yellowish brown 
__________________________________________________________________________ 
EXAMPLE 14 
36.1 parts of 4-.beta.-sulfatoethylsulfonyl-aniline-2-sulfonic acid are 
diazotized according to the instructions of Example 1. A neutralized 
solution of 22.3 parts of 1-naphthylamine-6-sulfonic acid in 150 parts of 
water is added to this diazonium salt solution and the coupling reaction 
is completed by the gradual addition of sodium bicarbonate at a pH value 
of 4. The pH value is then adjusted to 6.5, 20 parts by volume of an 
aqueous 5 N sodium nitrite solution are added and the resulting solution 
is slowly poured onto a mixture of 400 parts of ice and 35 parts of 31% 
strength hydrochloric acid. Stirring is continued for about 2 hours at 
approx. 5.degree. C., and excess nitrous acid is then destroyed with a 
little amidosulfonic acid. A cooled solution of 25.7 parts of the sodium 
salt of N-(.beta.-sulfoethyl)-3-chloroaniline in 180 parts of water is 
then added and the pH is maintained between 4 and 5 by sprinkling sodium 
acetate onto the mixture. The resulting disazo compound is isolated from 
the coupling batch either by salting out with sodium chloride or by 
spray-drying. A dark brown powder is obtained which in addition to 
electrolyte contains the sodium salt of the compound of the formula 
##STR23## 
This compound is very highly suitable as a dyestuff and produces very 
intense brown dyeings and prints, which have good fastness properties, on 
cotton and wool, by the application and fixing methods customary for 
fiber-reactive dyestuffs. 
EXAMPLES 15 TO 30 
To prepare a disazo compound according to the invention, the procedure of 
Example 14 is followed, but here the sodium salt of 
N-(.beta.-sulfoethyl)-3-chloroaniline, which serves as coupling component, 
is replaced by an equivalent amount of one of the coupling components 
which are indicated in the examples in the following tables and which 
correspond to the general formula (3). The disazo compound according to 
the invention which is also indicated and corresponds to the general 
formula (1) is also obtained in good yield. These fiber-reactive disazo 
compounds according to the invention also have very good dyestuff 
properties with very good application properties; they produce on the 
fiber materials mentioned in the descriptive section, in particular on 
cellulose fiber materials and wool, by the application and fixing methods 
customary for fiber-reactive dyestuffs, dyeings and prints having good to 
very good fastness properties and the shade indicated in the particular 
example in the table. The formula moiety M present in the compounds 
indicated by means of the formula has the abovementioned meaning. It 
preferably represents an alkali metal, in particular sodium. The formula 
radical D.sub.2 indicated for the compound according to the invention 
represents the radical of the formula 
##STR24## 
with M having the above-mentioned meaning. 
__________________________________________________________________________ 
Coupling component 
Disazo compound cor- Shade 
Ex- corresponding to the 
responding to the on 
ample 
general formula (3) 
general formula (1) cotton 
__________________________________________________________________________ 
15 3-Methyl-Nethyl- N(.beta.-sulfoethyl)- aniline 
##STR25## bluish violet 
16 3-Chloro-N,Nbis- (.beta.-sulfatoethyl)- aniline 
##STR26## opaque violet 
17 3-Chloro-6-methyl- N(.beta.-sulfoethyl)-aniline 
##STR27## opaque bluish red 
18 N(.beta.-Cyanoethyl)- N(.beta.-sulfatoethyl)- aniline 
##STR28## bluish red 
19 3-Methyl-Nethyl- N(.beta.-sulfato-.gamma.-sulfo- n-propyl)-aniline 
##STR29## bluish violet 
20 N(.beta.-Sulfato-ethyl)- N(.beta.-sulfato-.gamma.-sulfo- n-propyl)-ani 
line 
##STR30## violet- tinged brown 
21 2,5-Dichloro-N(.beta.-sul- foethyl)-aniline 
##STR31## brownish bluish red 
22 3-Methyl-N,N(.beta.-sul- fatoethyl)-aniline 
##STR32## bluish violet 
23 N,N Bis-(.beta.-sulfo- ethyl)-aniline 
##STR33## bluish red 
24 N(.beta.-Sulfoethyl)- aniline 
##STR34## reddish brown 
25 N(.beta.-Hydroxyethyl)- N(.beta.-sulfoethyl)- aniline 
##STR35## bluish red 
26 2-Chloro-N(.beta.-sulfo- ethyl)-aniline 
##STR36## reddish brown 
27 NMethyl-N(.beta.-hydroxy- .gamma.-sulfo-n-propyl)- aniline 
##STR37## bluish red 
28 3-Chloro-N(.gamma.-sulfo- n-propyl)-aniline 
##STR38## brown 
29 2-Methoxy-N(.beta.-sulfo- ethyl)-aniline 
##STR39## violet 
30 2,3-Dichlor-N(.beta.- sulfoethyl)-aniline 
##STR40## reddish brown 
__________________________________________________________________________ 
EXAMPLE 31 
59.4 parts of the aminoazo compound of the formula 
##STR41## 
are diazotized according to the instructions of Example 14 and thereafter 
coupled with a cooled aqueous solution of 26.5 parts of 
N-(.beta.-sulfoethyl)-N-ethyl-3-methyl-aniline to give a disazo compound. 
After a customary working-up by means of spray-drying or salting-out, an 
alkali metal salt of the compound of the formula 
##STR42## 
which have very good dyestuff properties, is obtained. The dyestuff salt 
produces very intense bluish violet dyeings and prints, which have good 
fastness properties, on cotton and wool, by the application methods 
customary for fiber-reactive dyestuffs. 
EXAMPLE 32 
49.3 parts of 
4-(.beta.-sulfatoethylsulfonyl)-3',6'-dimethyl-4'-aminoazobenzene-2-sulfon 
ic acid are adjusted in 300 parts of water to a pH value of 6 by means of 
sodium bicarbonate, and 20 parts by volume of aqueous 5 N sodium nitrite 
solution is added to the solution. This mixture is slowly added to a 
mixture of 200 parts of ice and 35 parts of 31% strength aqueous 
hydrochloric acid; the resulting diazotizing reaction is completed by 
stirring for 3 hours at a temperature of 5.degree.-10.degree. C. Excess 
nitrous acid is destroyed with a little amidosulfonic acid. For the 
coupling reaction, a cooled aqueous solution of 25.1 parts of the sodium 
salt of N-ethyl-N-(.beta.-sulfoethyl)-aniline is then added and the pH 
value is adjusted to 5.5 to 6 by sprinkling in sodium bicarbonate. After 
the coupling is complete, the sodium salt of the compound of the formula 
##STR43## 
is isolated in a customary manner by spray-drying. The compound has very 
good dyestuff properties and produces dyeings and prints in the shades of 
bluish-tinged bluish red, which have good fastness properties, on cotton 
and wool, by the application and fixing methods customary for 
fiber-reactive dyestuffs. 
EXAMPLES 33 TO 49 
More disazo compounds according to the invention are listed in the form of 
the free acid in the examples in the following tables. They can be 
prepared in a method according to the invention from their diazo and 
coupling components which are evident from the formulae, for example 
analogously to one of the exemplary embodiments indicated above. They are 
isolated from the reaction batches preferably in the form of their sodium 
salts. They likewise are very good dyestuffs which have fiber-reactive 
properties and they have very good technological properties; they produce, 
on the fiber materials mentioned in the descriptive section, in particular 
on cellulose fiber materials and wool, by the application and fixing 
methods customary for fiber-reactive dyestuffs, dyeings and prints having 
good to very good fastness properties and the shades indicated. 
__________________________________________________________________________ 
Shade 
Ex- on 
ample 
Disazo compound of the formula (1) cotton 
__________________________________________________________________________ 
33 
##STR44## violet 
34 
##STR45## violet 
35 
##STR46## reddish blue 
36 
##STR47## violet- tinged brown 
37 
##STR48## reddish brown 
38 
##STR49## brown 
39 
##STR50## bluish violet 
40 
##STR51## violet- tinged brown 
41 
##STR52## brown 
42 
##STR53## bluish violet 
43 
##STR54## yellowish red brown 
44 
##STR55## bluish- tinged bluish red 
45 
##STR56## violet- tinged brown 
46 
##STR57## brownish violet 
47 
##STR58## brown 
48 
##STR59## bluish red 
49 
##STR60## bluish red 
__________________________________________________________________________ 
EXAMPLES 50 TO 57 
To prepare a disazo compound according to the invention the procedure of 
Example 31 is followed, but here 
N-(.beta.-sulfoethyl)-N-ethyl-3-methyl-aniline, which serves as a coupling 
component, is replaced by an equivalent amount of one of the coupling 
components indicated in the examples in the tables below and which 
correspond to the general formula (3). The disazo compound according to 
the invention, also indicated and corresponding to the general formula 
(1), is obtained in likewise good yield. These fiber-reactive disazo 
compounds according to the invention also have very good dyestuff 
properties with very good application properties; they produce, on the 
fiber materials mentioned in the descriptive section, in particular on 
cellulose fiber materials and cotton, by the application and fixing 
methods customary for fiber reactive dyestuffs, dyeings and prints which 
have good to very good fastness properties and the shade indicated in the 
particular example in the table. The formula moiety M present in the 
compound indicated by means of the formula has the abovementioned meaning; 
it preferably represents an alkali metal, in particular sodium. The 
formula radical D.sub.3 indicated for the compound according to the 
invention represents a radical of the formula 
##STR61## 
with M having the abovementioned meaning. 
__________________________________________________________________________ 
Coupling component 
Disazo compound 
Ex- corresponding to the 
corresponding to the 
ample 
general formula (3) 
general formula (1) Shade 
__________________________________________________________________________ 
50 N(4'-Sulfophenethyl)- aniline 
##STR62## reddish brown 
51 N(.beta.-Cyanoethyl)-N(4'- sulfophenethyl)- aniline 
##STR63## reddish brown 
52 N(.beta.-Cyanoethyl)-N (.beta.-sulfatoethyl)- aniline 
##STR64## reddish brown 
53 3-Chloro-N,N bis-(.beta.- sulfatoethyl)- aniline 
##STR65## violet- tinged brown 
54 2,5-Dichloro-N (.beta.- sulfoethyl)-aniline 
##STR66## brown 
55 3-Methyl-N ethyl-N (.beta.-sulfato-.gamma.-sulfo- n-propyl)-aniline 
##STR67## bluish- tinged bluish red 
56 3-Methyl-N ethyl- (3'-sulfobenzyl)- aniline 
##STR68## bluish- tinged bluish red 
57 3-Chlor-N (.beta.-carb- oxyethyl)-N(.beta.- sulfoethyl)-aniline 
##STR69## reddish brown 
__________________________________________________________________________ 
EXAMPLES 58 TO 71 
Further disazo compounds according to the invention are listed in the form 
of the free acid in the examples in the following tables. They can be 
prepared by a method according to the invention from their diazo and 
coupling components which are evident from the formulae, for example 
analogously to one of the exemplary embodiments mentioned above. They are 
isolated from the reaction batches preferably in the form of their sodium 
salts. They are also very good dyestuffs which have fiber-reactive 
properties and have very good application properties; they produce, on the 
fiber materials mentioned in the descriptive section, in particular on 
cellulose fiber materials and wool, by the application and fixing methods 
customary for fiber-reactive dyestuffs, dyeings and prints which have good 
to very good fastness properties and the shades indicated. 
__________________________________________________________________________ 
Shade 
Ex- on 
ample 
Disazo compound of the formula (1) cotton 
__________________________________________________________________________ 
58 
##STR70## brownish- tinged bluish red 
59 
##STR71## bluish- tinged bluish red 
60 
##STR72## brownish violet 
61 
##STR73## violet 
62 
##STR74## red brown 
63 
##STR75## brown violet 
64 
##STR76## dark brown 
65 
##STR77## bluish brown 
66 
##STR78## violet 
67 
##STR79## bluish- tinged bluish red 
68 
##STR80## bluish- tinged bluish red 
69 
##STR81## violet- tinged brown 
70 
##STR82## violet- tinged brown 
71 
##STR83## brown 
72 
##STR84## brownish violet 
__________________________________________________________________________