Fibre-reactive dyes containing halopyrimidine radicals to which a vinylsulfonyl or the like group is attached by means of a bridge member

Reactive dyes of the formula ##STR1## in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, X is a substituent which is detatchable in the form of an anion, A is arylene or C.sub.2-6 -alkylene, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z radical, Z is an inorganic or organic radical which is detachable under alkaline conditions, B is hydrogen or the radical of a substituted or unsubstituted hydrocarbon, T is a negative substituent, and n is 1 or 2, are suitable for dyeing or printing cellulose-containing and nitrogen-containing materials and produce, in high colouristic yields, dyeings and prints having good fastness properties.

The present invention relates to novel reactive dyes, to a process for 
their preparation, and to their use for dyeings or printing fibre 
materials. 
The practice of dyeing with reactive dyes has in recent years led to 
increased demands on the quality of the dyeing and the economics of the 
dyeing process. There consequently continues to be a demand for new 
reactive dyes with improved properties, in particular application 
properties. 
The demand these days in the dyeing of cotton by the cold pad-batch method 
is for reactive dyes which are sufficiently substantive at the low dyeing 
temperature and which also have good wash-off properties. They should also 
be highly reactive, so that only short pad-batching times are required, 
and they should in particular produce dyeings having high degrees of 
fixation. Existing dyes meet these requirements only to an insufficient 
degree. 
It is therefore the object of the present invention to provide new, 
improved reactive dyes for the cold pad-batch method which have the 
qualities characterised above to a high degree. The new dyes should be 
distinguished especially by high degrees of fixation and high fibre-dye 
bond stabilities, and the unfixed portions on the fibre should moreover be 
readily washed off. They should also produce dyeings having good all-round 
fastness properties, for example light and wet fastness properties. 
This object is achieved with the novel fibre-reactive dyes defined 
hereinafter. 
The invention accordingly provides reactive dyes of the formula 
##STR2## 
in which D is the radical of a dye of the monoazo, polyazo, metal complex 
azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, 
phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, 
naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is 
hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, X is a 
substituent which is detachable in the form of an anion, A is arylene or 
C.sub.2-6 -alkylene, Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z 
radical, Z is an inorganic or organic radical which is detachable under 
alkaline conditions, B is hydrogen or the radical of a substituted or 
unsubstituted hydrocarbon, T is a negative substituent, and n is 1 or 2. 
The radical D in the formula (1) can contain, bonded to its basic 
structure, the substituents customary with organic dyes. 
Example of further substituents on the radical D are alkyl groups having 1 
to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl or butyl, 
alkoxy groups having 1 to 4 carbon atoms, such as methoxy, ethoxy, 
propoxy, isopropoxy or butoxy, acylamino groups having 1 to 8 carbon 
atoms, such as acetylamino, propionylamino or benzoylamino, amino, 
alkylamino having 1 to 4 carbon atoms, such as methylamino, ethylamino, 
propylamino, isopropylamino or butylamino, phenylamino, 
N,N-.beta.-hydroxyethylamino, N,N-di-.beta.-sulfatoethylamino, 
sulfobenzylamino, N,N-disulfobenzylamino, alkoxycarbonyl having 1 to 4 
carbon atoms in the alkoxy radical, such as methoxycarbonyl or 
ethoxycarbonyl, alkylsulfonyl having 1 to 4 carbon atoms, such as 
methylsulfonyl or ethylsulfonyl, trifluoromethyl, nitro, cyano, halogen, 
such as fluorine, chlorine or bromine, carbamoyl, N-alkylcarbamoyl having 
1 to 4 carbon atoms in the alkyl radical, such as N-methylcarbamoyl or 
N-ethylcarbamoyl, sulfamoyl, N-alkylsulfamoyl having 1 to 4 carbon atoms, 
such as N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, 
N-isopropylsulfamoyl or N-butylsulfamoyl, 
N-(.beta.-hydroxyethyl)-sulfamoyl, N,N-di-(.beta.-hydroxyethyl)-sulfamoyl, 
N-phenylsulfamoyl, ureido, hydroxyl, carboxyl, sulfomethyl and sulfo. The 
radical D preferably contains one or more sulfonic acid groups. Reactive 
dyes of the formula (1) in which D is the radical of an azo dye contain as 
substituents especially methyl, ethyl, methoxy, ethoxy, acetylamino, 
benzoylamino, amino, chlorine, bromine, ureido, hydroxyl, carboxyl, 
sulfomethyl or sulfo. 
An alkyl radical R is straight-chain or branched; it can be further 
substituted, for example by halogen, hydroxyl, cyano, C.sub.1-4 -alkoxyl, 
carboxyl or sulfo. Examples for R are the radicals methyl, ethyl, propyl, 
isopropyl, butyl, isobutyl, sec.-butyl, tert.-butyl, carboxymethyl, 
.beta.-carboxyethyl, .beta.-carboxypropyl, methoxycarbonylmethyl, 
ethoxycarbonylmethyl, .beta.-methoxyethyl, .beta.-ethoxyethyl, 
.beta.-methoxypropyl, .beta.-chloroethyl, .beta.-bromopropyl, 
.beta.-hydroxyethyl, .beta.-hydroxybutyl, .beta.-cyanoethyl, sulfomethyl, 
.beta.-sulfoethyl, aminosulfonylmethyl and .beta.-sulfatoethyl. R is 
preferably hydrogen, methyl or ethyl. 
Substituent X, which is detachable in the form of an anion, is for example 
a halogen atom, such as fluorine, chlorine or bromine, a low molecular 
weight alkylsulfonyl group, such as methylsulfonyl or ethylsulfonyl, a 
phenylsulfonyl radical, a sulfonic acid or phosphonic acid group or a 
quaternised group. X is preferably fluorine or chlorine. 
An arylene bride member A is for example phenylene, naphthylene or the 
radical of biphenyl, stilbene, diphenylmethane or diphenyl ether. These 
radicals can contain further substituents, for example methyl, ethyl, 
methoxy, ethoxy, fluorine, chlorine, bromine, nitro, cyano, acetylamino, 
hydroxyl, carboxyl or sulfo. An arylene A is preferably phenylene or 
naphthylene. A C.sub.2-6 -alkylene radical A in formula (1) can be 
straight-chain or branched alkylene radical, for example ethylene, 
n-propylene, isopropylene, n-butylene, n-pentylene or n-hexylene. This 
radical can likewise be further substituted, for example by chlorine, 
cyano or hydroxyl. Preference is given to C.sub.2-4 -alkylene which 
contains no further substituents, in particular to ethylene. 
An inorganic or organic radical Z which is detachable under alkaline 
conditions can be for example one of the following anionically detachable 
groups: 
##STR3## 
Z is preferably a --OSO.sub.3 H, --SSO.sub.3 H, --OCOCH.sub.3, --OPO.sub.3 
H.sub.2 or --Cl radical. 
A radical of a substituted or unsubstituted hydrocarbon, B is for example 
an alkyl radical which is straight-chain or branched, which preferably has 
1 to 6 carbon atoms, and which can be further substituted, for example by 
halogen, hydroxyl, cyano, alkoxy, carboxyl or sulfo, or an unsubstituted 
alkyl radical having 7 to 20 carbon atoms, a cyclohexyl radical, or a 
phenyl radical which can be substituted, for example by methyl, ethyl, 
methoxy, ethoxy, chlorine, bromine, carboxyl, sulfo or sulfomethyl. 
Examples of B are the following substituents: methyl, ethyl, propyl, 
isopropyl, butyl, isobutyl, sec.-butyl, tert.-butyl, pentyl, hexyl, nonyl, 
dodecyl, hexadecyl, pentadecyl, carboxymethyl, .beta.-carboxyethyl, 
.beta.-carboxypropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 
.beta.-methoxyethyl, .beta.-ethoxyethyl, .beta.methoxypropyl, 
.beta.-chloroethyl, .beta.-chloropropyl, .beta.-bromopropyl, sulfomethyl, 
.beta.-sulfoethyl, aminosulfonylmethyl, .beta.-sulfatoethyl, cyclohexyl, 
phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, p-ethylphenyl, 
p-methoxyphenyl, o-, m- or p-sulfophenyl, p-carboxyphenyl and 
p-sulfomethylphenyl. Unsubstituted alkyl radicals having 1 to 4 carbon 
atoms are preferred. 
B is in particular hydrogen or a radical of the formula 
EQU --A--SO.sub.2 --Y (2), 
in which A and Y are as defined under the formula (1). If B is a radical of 
the formula (2), then there are two radicals of the formula (2) bonded to 
the nitrogen atom of the external radical in the formula (1); the two 
radicals of the formula (2) can be identical or different. They are 
preferably identical. 
The radical T is to be understood as meaning a negative substituent in the 
conventional sense. It is a key atom, for example chlorine, which, owing 
to its high core charge, attracts the bonding electrons more strongly than 
does the pyrimidine ring carbon atom to which T is bonded, and therefore 
induces a positive charge on the carbon; or it is a group of atoms, for 
example nitro, in which the positive charge on the atom bonded to the 
carbon has the same electron-attracting effect as the higher core charge 
on chlorine had and likewise gets the predominant share of the pair of 
bonding electrons and as a result causes the carbon to acquire a positive 
charge. Examples of possible negative substituents T are nitro, 
alkoxysulfonyl, alkylsulfonyl, alkylsulfinyl, cyano, alkoxycarbonyl, 
carboxyl, alkanoyl, chlorine and hydroxyl. 
That part of the formula (1) which is enclosed in square brackets is a 
reactive radical which can occur once or twice at the molecule; the two 
possibilities are of equal importance. If n is 2, two reactive radicals 
can be identical or different; they are preferably identical. The reactive 
radical contains two substituents, namely X and Y, which can react in a 
manner of a nucleophilic substitution and in the manner of a nucleophilic 
addition. 
Fibre-reactive compounds are to be understood as meaning compounds which 
are capable of reacting with the hydroxyl groups of cellulose, the amino, 
carboxyl, hydroxyl and thiol groups in wool and silk, or the amino and 
possibly carboxyl groups of synthetic polyamides and form covalent 
chemical bonds. 
Preferred embodiments of the reactive dyes of the formula (1) are: 
(a) reactive dyes of the formula (1) in which X is fluorine or chlorine; 
(b) reactive dyes of the formula (1) in which T is methylsulfonyl; 
(c) reactive dyes of the formula (1) in which B is hydrogen or C.sub.1-4 
-alkyl and A is substituted or unsubstituted phenylene or naphthylene or 
C.sub.2-6 -alkylene; 
(d) reactive dyes of the formula (1) in which B is a radical of the formula 
EQU --A--SO.sub.2 --Y (2) 
in which A and Y are as defined under the formula (1); and 
(e) reactive dyes of the formula (1) in which A is ethylene. 
The symbols of the formula (1) which were not mentioned under (a) to (e) 
are as defined under the formula (1). Also suitable are in particular 
combinations of features given under (a) to (e). Also preferred are: 
(f) reactive dyes as per (c), of the formula 
##STR4## 
in which D, R, Y and n are as defined under the formula (1) and the 
benzene or naphthalene radical can contain further substituents in 
addition to --SO.sub.2 --Y; 
(g) reactive dyes as per (c), of the formula 
##STR5## 
in which D, R, Y and n are as defined under the formula (1) and A is 
C.sub.2-4 -alkylene; 
(h) reactive dyes as per (g) in which A is ethylene; 
(i) reactive dyes as per (d), of the formula 
##STR6## 
in which D, R, Y and n are as defined under the formula (1) and A is 
C.sub.2-4 -alkylene; 
(j) reactive dyes as per (i) in which A is ethylene; 
(k) reactive dyes of the formula (1) or as per (a) to (j) in which Y is 
vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, 
.beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl; 
(1) reactive dyes of the formula (1) or as per (a) to (k) in which D is the 
radical of a monoazo or disazo dye; 
(m) reactive dyes of the formula (1) or as per (a) to (k) in which D is the 
radical of a metal complex azo or formazan dye; 
(n) reactive dyes of the formula (1) or as per (a) to (k) in which D is the 
radical of an anthraquinone dye; and 
(o) reactive dyes as per (m) in which D is the radical of a 1:1 copper 
complex azo dye of the benzene or naphthalene series and the copper atom 
is bonded on either side to a metallisable group in ortho-position 
relative to the azo bridge. 
Particular preference is given to: 
(p) reactive dyes as per (1), of the formula 
##STR7## 
in which D.sub.1 is the radical of a diazo component of the benzene or 
naphthalene series, K is the radical of a coupling component of the 
benzene or naphthalene series or of the heterocyclic series, R is 
hydrogen, methyl or ethyl, n is 1 or 2, and the reactive radical is bonded 
to the diazo component or to the coupling component, or a reactive radical 
each is bonded to the diazo component and to the coupling component; 
(q) reactive dyes as per (1), of the formula 
##STR8## 
in which D.sub.1 and D.sub.2 are each a radical of a diazo component of 
the benzene or naphthalene series, K is the radical of a coupling 
component of the benzene or naphthalene series or of the heterocyclic 
series, R is hydrogen, methyl or ethyl, n is 1 or 2, and the reactive 
radical is bonded to diazo component D.sub.1 or to coupling component K, 
or a reactive radical each is bonded to D.sub.1 and K; 
(r) reactive dyes as per (1), of the formula 
##STR9## 
in which D.sub.1 and D.sub.2 are each a radical of a diazo component of 
the benzene or naphthalene series, K is the radical of a coupling 
component of the aminonaphtholsulfonic acid series, R is hydrogen, methyl 
or ethyl, n is 1 or 2, and the reactive radical is bonded to diazo 
component D.sub.1 or to diazo component D.sub.2, or a reactive radical 
each is bonded to D.sub.1 and D.sub.2 ; and 
(s) 1:1 copper complexes of reactive dyes as per (p) to (r). 
The process for preparing the reactive dyes of the formula (1) comprises 
condensing, in any order, organic dyes of the formula 
##STR10## 
or dye precursors, at least one equivalent of a pyrimidine of the formula 
##STR11## 
and at least one equivalent of an amine of the formula 
##STR12## 
to give a reactive dye of the formula (1), D, R, n, X, T, A, Y and B in 
the formulae (9) to (11) being as defined under the formula (1), and if 
dye precursors are used converting these into the desired end dyes. 
The process according to the invention can, if desired, be followed by a 
further conversion reaction. If the end dyes are prepared from precursors 
these conversion reactions are chiefly couplings leading to azo dyes. 
As the individual steps of the process given above can be carried out in 
different orders, there are various possible process variants. In general, 
the reaction is carried out in successive steps, the order of the 
elementary reactions between the individual reactants advantageously being 
arranged in accordance with the particular conditions. As hydrolysis of 
the halogenopyrimidine radical can occur under certain conditions, any 
intermediate which contains acetylamino groups has to be hydrolysed (to 
split off the acetyl groups) before it is condensed with a 
halogenopyrimidine. Which reaction involved in preparing a secondary 
condensation product from an amine of the formula (11), the pyrimidine of 
the formula (10) and the organic dye of the formula (9) or a precursor is 
best carried out first, viz. that of the pyrimidine with the amine or that 
with the organic dye or a precursor thereof, varies from case to case and 
is arranged in particular in accordance with the solubility of the amino 
compounds involved and the basicity of the amino groups to be acylated. 
Another possible conversion reaction is a subsequent reaction at the 
radical X. If desired, detachable radicals X can be replaced by other 
detachable radicals after the condensation of the pyrimidine of the 
formula (1) with a dye of the formula (9) or with a dye precursor. For 
instance, a halogen atom can be replaced by a different halogen, using a 
halogenating agent. Reaction of tertiary bases, such as trimethylamine, 
pyridine or 1,4-diazabicyclo[2.2.2]octane, produces the corresponding 
amino compounds, and the quaternisation with hydrazines, such as 
N,N-dimethylhydrazine, the corresponding hydrazinium compounds. Sulfites, 
for example sodium sulfite, and sulfinates can be used to replace halogen 
by, respectively sulfo and sulfonyl, for example a 
3'-carboxyphenylsulfonyl group or the like. The reaction with cyanides, 
for example potassium cyanide, and thiocyanates, for example potassium 
thiocyanate, can be used to replace chlorine by, respectively, nitrile and 
thiocyanate groups, which are likewise reactive. Furthermore, halogen 
atoms or other reactive groups can also be replaced, by their 
corresponding radicals, through the action of sodium azide or compounds 
which contain reactive methylene groups, for example cyanoacetates, 
malonates or acetyl acetone. A detachable substituent X can in many cases 
be replaced by other detachable substituents even before the pyrimidine of 
the formula (10) is condensed with a dye of the formula (9) or with a 
precursor thereof. 
Furthermore, the synthesis can be followed by elimination reactions. It is 
possible, for example, to treat reactive dyes of the formula (1) which 
contain sulfatoethylsulfonyl radicals with agents, such as sodium 
hydroxide, which split off hydrogen halide so as to convert the 
sulfatoethylsulfonyl radicals into vinylsulfonyl radicals. 
A modified form of the process comprises first of all preparing a dye which 
contains a precursor of the reactive radical and then to convert this 
precursor of the reactive radical and then converting this precursor 
stage, for example by an esterification or addition reaction, into the 
final stage. For instance, it is possible to prepare a dye in which Y is a 
HO--CH.sub.2 CH.sub.2 -- radical and to react the intermediate with 
sulfuric acid before or after the acylation, so that the hydroxyl group is 
converted into the sulfato group; or to use an analogous dye in which Y is 
the H.sub.2 C.dbd.CH-- vinyl group and to add thiosulfuric acid onto the 
intermediate, forming an HO.sub.3 SS--CH.sub.2 CH.sub.2 -- radical. The 
hydroxyl group in a dye of the formula (1) or in a suitable precursor 
thereof is sulfated, for example, through reaction with concentrated 
sulfuric acid at 0.degree. C. to moderately elevated temperatures. The 
sulfation can also be effected by reacting the hydroxy compound at 
10.degree. to 80.degree. C. in a polar organic solvent, for example 
N-methylpyrrolidone, with two equivalents of chlorosulfonic acid per 
hydroxyl group. The sulfation is preferably effected by adding the 
compound in question at temperatures between 5.degree. and 15.degree. C. 
to sulfuric acid monohydrate. If Z is a radical which is detachable under 
alkaline conditions other than a sulfato group, for example if it is a 
thiosulfato group, it is introduced into a compound of the formula (1) or 
into an intermediate in conventional manner per se. The synthesis route 
via an intermediate of the reactive radical in many cases has a single 
product and goes to completion. 
The process variant where the starting materials are dye precursors is 
suitable for preparing reactive dyes of the formula (1) in which D is the 
radical of a dye composed of two or more components. Examples of dyes of 
this type, composed of two or more components, are: monoazo, disazo, 
trisazo, metal complex azo, formazan and azomethine dyes. In principle, 
the reactive dyes of the formula (1) of all classes of dye can be prepared 
in a manner known per se or analogously to known procedures by starting 
from precursors or intermediates of dyes containing fibre-reactive 
radicals as shown in the formula (1), or introducing these fibre-reactive 
radicals into suitable intermediates having the characteristics of dyes. 
Preference is given to reactive dyes of the formula (1) in which D is the 
radical of a monoazo or disazo dye or of a metal complex azo dye. In this 
case the reactive radicals of the formula 
##STR13## 
are bonded to the diazo or coupling component or, if n is 2, to different 
or identical radicals of starting components, i.e. diazo or coupling 
components. Preferably, in the event that n is 2, the two reactive 
radicals are bonded to separate components, one to the diazo component and 
the other to the coupling component. The reactive dyes then have for 
example the formulae 
##STR14## 
in which R.sub.1 and R.sub.2, independently of each other, are defined the 
same way as R in the formula (1), D.sub.1 is the radical of a diazo 
component, K is the radical of a coupling component, and .circle.R is a 
reactive radical of the formula (12). Also suitable are reactive dyes of 
the formulae (13) to (15) in which the radical D.sub.1 and/or K includes a 
further reactive radical, so that trireactive and tetrareactive dyes are 
also coupled. The additional reactive radicals included in D.sub.1 or K 
can be bonded to D.sub.1 and/or K via an amino group, like .circle.R , or 
in some other way, for example through a direct bond. 
An additional reactive radical which can be included in D.sub.1 or K is in 
particular a low molecular weight alkanoyl or alkylsulfonyl radical which 
is substituted by a detachable atom or a detachable group, a low molecular 
weight alkenoyl or alkenesulfonyl radical which is unsubstituted or 
substituted by a detachable atom or a detachable group, a carbonyl or 
sulfonyl group, a radical which contains carbocyclic or heterocyclic 4-, 
5- or 6-membered rings and is substituted by a detachable atom of a 
detachable group, or is, or contains, a triazine or pyrimidine radical 
which is substituted by a detachable atom or a detachable group. Examples 
of reactive radicals of this type are any 6-membered heterocyclic radicals 
bonded via an amino group and containing halogen atoms, such as a 
halogenotriazine or halogenopyrimidine radical, or an aliphatic acyl 
radical, such as a halogenoacetyl or halogenopropionyl radical. 
The additional reactive radical is in particular a vinylsulfonyl, 
.beta.-sulfatoethylsulfonyl, .beta.-thiosulfatoethylsulfonyl, 
.beta.-chloroethylsulfonyl or .beta.-acetoxyethylsulfonyl radical which is 
bonded directly or via a bridge member. Preference should thus also be 
given to dyes of the type depicted by way of illustration in the final 
three Examples. 
The above explanations apply, analogously, also to disazo dyes (see Example 
6) and metal complex azo dyes as well as to other chromophores mentioned 
in the definition of radical D in the formula (1). 
Also suitable are reactive dyes of the formula (1) in which one of the 
reactive radicals, or both, are bonded to the chromophore via a radical of 
the formula 
##STR15## 
In these dyes the radical of the formula (12) is bonded to E via the 
--N(R)-- group; E is a substituted or unsubstituted aliphatic or aromatic 
bridge member. Bridge member E is preferably an alkylene or arylene 
radical. For instance, E can be a long (for example of 10 or more carbon 
atoms) or shorter, straight-chain or branched alkylene radical; suitable 
alkylene radicals have in particular 2 to 6 carbon atoms, examples being 
ethylene, propylene, butylene, hexylene or cyclohexylene. An arylene 
radical E is for example a naphthylene radical, the radical of a diphenyl 
or of stilbene or in particular a phenylene radical. Radical E can contain 
further substituents, for example halogen atoms, such as fluorine, 
chlorine or bromine, alkyl groups having 1 to 4 carbon atoms, such as 
methyl, ethyl or propyl, alkoxy groups having 1 to 4 carbon atoms, such as 
methoxy, ethoxy, propyloxy or isopropyloxy, carboxyl or sulfo. R' and R", 
independently of each other, are each hydrogen or a substituted or 
unsubstituted C.sub.1-4 -alkyl radical; and V is a halogen atom, a 
substituted or unsubstituted amino group, hydroxyl or an alkoxy, aryloxy, 
alkylthio or arylthio group. 
If the starting materials used are dye precursors, reactive dyes of the 
formula (1) are prepared by condensing a --N(R)H-containing component of 
the dye of the formula (9) and a pyrimidine of the formula (10), 
condensing with an amine of the formula (11) beforehand or afterwards and 
reacting with the other component of the dye of the formula (9). In the 
synthesis of the preferred azo dyes the diazo components and the coupling 
components together must contain at least one --N(R)H amino group and can 
contain further amino groups. In this case the diazo components used are 
in particular 1,3-phenylenediamine-4-sulfonic acid, 
1,4-phenylenediamine-2-sulfonic acid, 1,4-phenylenediamine-2,5-disulfonic 
acid or 1,3-phenylenediamine-4,6-disulfonic acid. If desired it is 
possible to use corresponding acetylamino or nitro compounds in which the 
acetylamino and nitro groups are converted into H.sub.2 N groups by 
hydrolysis and reduction respectively before the condensation with the 
2,4,6-trihalogenopyrimidine. 
If groups capable of metal complex formation, such as hydroxyl, carboxyl, 
amino or sulfo, are present in the reactive dyes prepared, the reactive 
dyes can also be subsequently metallised. For example, metal complex azo 
dyes are obtained by treating azo compounds prepared according to the 
invention which contain complexing groups, for example hydroxyl or 
carboxyl groups, in ortho-ortho'-position relative to the azo bridge with 
heavy-metal donors before or, if desired, even after the condensation with 
the 2,4,6-trihalogenopyrimidine of the formula (10). Copper complexes of 
reactive dyes of the formula (1) are of particular interest. Metallisation 
can be effected not only by the method mentioned above but also by 
dealkylating metallisation and, for synthesising copper complexes, 
oxidative coppering. 
The most important process variants are illustrated in the Examples. 
There now follows a list of specific starting materials which can be used 
for preparing the reactive dyes of the formula (1). 
##STR16## 
Preferred metal atoms are Cu (1:1 complex) or Cr and Co (1:2 complex). Cr- 
and Co-complexes can contain one or two molecules of the azo component of 
the formula given above, i.e. these complexes can be symmetrical or 
contain any other ligand and be asymmetrical. 
##STR17## 
In this formula Pc is the Cu or Ni phthalocyanine radical; the total 
number of substituents on the Pc skeleton is 4. 
##STR18## 
In the formulae shown above the radicals R.sub.5 to R.sub.10 and R.sub.17 
to R.sub.20 are each hydrogen or C.sub.1-4 -alkyl, and the radicals 
R.sub.3, R.sub.4 and R.sub.11 to R.sub.16 are each hydrogen, C.sub.1-4 
-alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkyanoylamino, ureido or halogen 
independently of one another where they belong to one and the same 
formula. Preferably the radicals R.sub.5 to R.sub.10 and R.sub.17 to 
R.sub.20 are each hydrogen, methyl or ethyl and the radicals R.sub.3, 
R.sub.4 and R.sub.11 to R.sub.16 are each hydrogen, methyl, methoxy, 
ethoxy, acetylamino, ureido or chlorine. The aromatic rings in the above 
dyes can be further substituted, the benzene rings especially by methyl, 
methoxy, ethoxy, carboxyl, acetylamino or chlorine and the naphthalene 
rings in particular by methoxy, carboxyl, acetylamino, nitro or chlorine; 
the same applies to the anthraquinones, dioxazines and so on. The benzene 
rings are preferably not further substituted. The diazo components used in 
this case are in particular 1,3-phenylenediamine-4-sulfonic acid, 
1,4-phenylenediamine-2-sulfonic acid, 1,4-phenylenediamine-2,5-disulfonic 
acid or 1,3-phenylenediamine-4,6-disulfonic acid. 
Specific diazo and coupling components are: 
Diazo components: 
Aminobenzene, 1-amino-2-, -3- or -4-methylbenzene, 1-amino-2-, -3- or 
-4-methoxybenzene, 1-amino-2-, -3- or -4-chlorobenzene, 
1-amino-2,5-dichlorobenzene, 1-amino-2,5-dimethylbenzene, 
1-amino-3-methyl-6-methoxybenzene, 1-amino-2-methoxy-4-nitrobenzene, 
4-aminobiphenyl, 1-aminobenzene-2-, -3- or -4-carboxylic acid, 
2-aminodiphenylether, 1-aminobenzene-2-, -3- or -4-sulfonic acid, 
-N-methylamide, -N-ethylamide, -N,N-dimethylamide or -N,N-diethylamide, 
dehydrothio-p-toluidine-sulfonic acid, 
1-amino-3-trifluoromethyl-6-sulfonic acid, 1-amino-3- or -4-nitrobenzene, 
1-amino-3- or -4-acetylaminobenzene, 1-aminobenzene-2-, -3- or -4-sulfonic 
acid, 1-aminobenzene-2,4- and -2,5-disulfonic acid, 
1-amino-4-methylbenzene-2-sulfonic acid, 
1-amino-3-methylbenzene-6-sulfonic acid, 1-amino-6-methylbenzene-3- or 
-4-sulfonic acid, 1-amino-2-carboxybenzene-4-sulfonic acid, 
1-amino-4-carboxybenzene-2-sulfonic acid, 1-amino-4- or 
-5-chlorobenzene-2-sulfonic acid, 1-amino-6-chlorobenzene-3- or 
-4-sulfonic acid, 1-amino-3,4-dichlorobenzene-6-sulfonic acid, 
1-amino-2,5-dichlorobenzene-6-sulfonic acid, 
1-amino-2,5-dichlorobenzene-4-sulfonic acid, 
1-amino-4-methyl-5-chlorobenzene-2-sulfonic acid, 
1-amino-5-methyl-4-chlorobenzene-2-sulfonic acid, 1-amino-4- or 
-5-methoxybenzene-2-sulfonic acid, 1-amino-6-methoxybenzene-3- or 
-4-sulfonic acid, 1-amino-6-ethoxybenzene-3- or -4-sulfonic acid, 
1-amino-2,4-dimethoxybenzene-6-sulfonic acid, 
1-amino-2,5-dimethoxybenzene-4-sulfonic acid, 
1-amino-3-acetylaminobenzene-6-sulfonic acid, 
1-amino-4-acetylaminobenzene-2-sulfonic acid, 
1-amino-3-acetylamino-4-methylbenzene-6-sulfonic acid, 
2-amino-1-methylbenzene-3,5-disulfonic acid, 
1-amino-4-methoxybenzene-2,5-disulfonic acid, 1-amino-3- or 
-4-nitrobenzene-6-sulfonic acid, 1-aminonaphthalene, 2-aminonaphthalene, 
1-aminonaphthalene-2-, -4-, -5-, -6-, -7- or -8-sulfonic acid, 
2-aminonaphthalene-1-, -3-, -4-, -5-, -6-m, -7- or -8-sulfonic acid, 
2-aminonaphthalene-3,6- or -5,7-disulfonic acid, 1-aminonaphthalene-3,6- 
or -5,7-disulfonic acid, 2-aminonaphthalene-1,5-, -1,7-, -3,6-, -5,7-, 
-4,8- or -6,8-disulfonic acid, 1-aminonaphthalene-2,5,7-trisulfonic acid, 
2-aminonaphthalene-1,5,7-, -3,6,8- or -4,6,8-trisulfonic acid, 
1-hydroxyl-2-aminobenzene-4-sulfonic acid, 
1-hydroxyl-2-aminobenzene-5-sulfonic acid, 
1-hydroxy-2-aminobenzene-4,6-disulfonic acid, 
1-hydroxy-2-amino-4-acetylaminobenzene-6-sulfonic acid, 
1-hydroxy-2-amino-6-acetylaminobenzene-4-sulfonic acid, 
1-hydroxy-2-amino-4-chlorobenzene-5-sulfonic acid, 
1-hydroxy-2-amino-4-methylsulfonylbenzene, 1-amino- 
2-hydroxy-6-nitronaphthalene-6-sulfonic acid, 
2-amino-1-hydroxynaphthalene-4,8-disulfonic acid, 
4-aminoazobenzene-3,4'-disulfonic acid, 
3-methoxy-4-amino-6-methylazobenzene-2',4'-disulfonic acid, 
3-methoxy-4-amino-6-methylazobenzene-2',5'-disulfonic acid, 
1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-diamino-4-chlorobenzene, 
1,3-diamino-4-methylbenzene, 1,3-diamino-4-ethylbenzene, 
1,3-diamino-4-methoxybenzene, 1,3-diamino-4-ethoxybenzene, 
1,4-diamino-2-methylbenzene, 1,4-diamino-2-methoxybenzene, 
1,4-diamino-2-ethoxybenzene, 1,4-diamino-2-chlorobenzene, 
1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2,5-diethylbenzene, 
1,4-diamino-2-methyl-5-methoxybenzene, 1,4-diamino-2,5-dimethoxybenzene, 
1,4-diamino-2,5-diethoxybenzene, 2,6-diaminonaphthalene, 
1,3-diamino-2,4,6-trimethylbenzene, 
1,4-diamino-2,3,5,6-tetramethylbenzene, 1,3-diamino-4-nitrobenzene, 
4,4'-diaminostilbene, 4,4'-diaminodiphenylmethane, 
4,4'-diaminobiphenyl(benzidine), 3,3'-dimethylbenzidine, 
3,3'-dimethoxybenzidine, 3,3'-dichlorobenzidine, 3,3'-dicarboxybenzidine, 
3,3'-dicarboxymethoxybenzidine, 2,2'-dimethylbenzidine, 
4,2'-diaminodiphenyl(diphenyline), 2,6-diaminonaphthalene-4,8-disulfonic 
acid, 1,4-diaminobenzene-2-sulfonic acid, 
1,4-diaminobenzene-2,5-disulfonic acid, 1,4-diaminobenzene-2,6-disulfonic 
acid, 1,3-diaminobenzene-4-sulfonic acid, 
1,3-diaminobenzene-4,6-disulfonic acid, 
1,4-diamino-2-chlorobenzene-5-sulfonic acid, 
1,4-diamino-2-methylbenzene-5-sulfonic acid, 
1,5-diamino-6-methylbenzene-3-sulfonic acid, 
1,3-diamino-6-methylbenzene-4-sulfonic acid, 3-(3'- or 
4'-aminobenzoylamino)-1-aminobenzene-6-sulfonic acid, 
1-(4'-aminobenzoylamino)-4-aminobenzene-2,5-disulfonic acid, 
1,4-diaminobenzene-2-carboxylic acid, 1,3-diaminobenzene-4-carboxylic 
acid, 1,2-diaminobenzene-4-carboxylic acid, 
1,3-diaminobenzene-5-carboxylic acid, 1,4-diamino-2-methylbenzene, 
4,4'-diaminodiphenyl oxide, 4,4'-diaminodiphenylurea-2,2'-disulfonic acid, 
4,4'-diaminodiphenyloxyethane-2,2'-disulfonic acid, 
4,4'-diaminostilbene-2,2'-disulfonic acid, 
4,4'-diaminodiphenylethane-2,2'-disulfonic acid, 
2-amino-5-aminomethylnaphthalene-1-sulfonic acid, 
2-amino-5-aminomethylnaphthalene-1,7-disulfonic acid and 
1-amino-4-methoxy-5-aminomethylbenzene-6-sulfonic acid. 
If the diazo component to be used is not a diamine but is an 
aminoacetylamino compound from which the acetyl group is subsequently to 
be reeliminated by hydrolysis, as mentioned above in the description of 
the process, the monoacetyl compounds of the abovementioned diazo 
components are possible, examples being 
1-acetylamino-3-aminobenzene-4-sulfonic acid and 
1-acetylamino-4-aminobenzene-3-sulfonic acid. 
Examples of aromatic amines which can serve as diazo components in 
preparing the monoazo or polyazo dyes and which contain a vinylsulfonyl 
group or an equivalent reactive radical are: 
1-Amino-4-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-4-.beta.-thiosulfatoethylsulfonylbenzene, 
1-amino-4-vinylsulfonylbenzene, 
1-amino-4-.beta.-chloroethylsulfonylbenzene, 
1-amino-3-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-3-vinylsulfonylbenzene, 
1-amino-2-methoxy-5-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-2-methoxy-5-.beta.-thiosulfatoethylsulfonylbenzene, 
1-amino-2-methoxy-5-vinylsulfonylbenzene, 
1-amino-4-methoxy-3-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-4-methoxy-3-.beta.-vinylsulfonylbenzene, 
1-amino-2,5-dimethoxy-4-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-2,5-dimethoxy-4-vinylsulfonylbenzene, 
1-amino-2-methoxy-4-.beta.-sulfatoethylsulfonyl-5-methylbenzene, 
1-amino-2-methoxy-4-vinylsulfonyl-5-methylbenzene, 
1-amino-3-.beta.-sulfatoethylsulfonyl-6-carboxybenzene, 
1-amino-3-vinylsulfonyl-6-carboxybenzene, 
1-amino-4-.beta.-sulfatoethylsulfonylbenzene-2-sulfonic acid, 
1-amino-4-vinylsulfonylbenzene-2-sulfonic acid, 
1-amino-5-vinylsulfonylbenzene-2,4-disulfonic acid, 
1-amino-2-hydroxy-5-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-2-hydroxy-4-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-2-hydroxy-5-.beta.-sulfatoethylsulfonylbenzene-3-sulfonic acid, 
1-amino-2-bromo-4-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-2,6-dichloro-4-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-2,4-di-(.beta.-sulfatoethylsulfonyl)-benzene, 
1-amino-2,4-di-(.beta.-sulfatoethylsulfonyl)-5-chlorobenzene, 
1-amino-2,4-di-(.beta.-thiosulfatoethylsulfonyl)-5-chlorobenzene, 
1-amino-2,4-di-(vinylsulfonyl)benzene, 
1-amino-2,4-di-(vinylsulfonyl)-5-chlorobenzene, 
1-amino-2,4-di-(.beta.-acetoxyethylsulfonyl)-benzene, 
1-amino-2,4-di-(.beta.-acetoxyethysulfonyl)-5-chlorobenzene, 
2-amino-8-.beta.-sulfatoethylsulfonylnaphthalene, 
2-amino-6-.beta.-sulfatoethylsulfonylnaphthalene, 
2-amino-6-.beta.-sulfatoethylsulfonylnaphthalene-1-sulfonic acid, 
2-amino-8-.beta.-sulfatoethylsulfonylnaphthalene-6-sulfonic acid and 
2-amino-6,8-di-(.beta.-sulfatoethylsulfonyl)-naphthalene. 
Coupling components: 
Phenol, 1-hydroxy-3- or -4-methylbenzene, 1-hydroxybenzene-4-sulfonic acid, 
1-hydroxynaphthalene, 2-hydroxynaphthalene, 2-hydroxynaphthalene-6- or 
-7-sulfonic acid, 2-hydroxynaphthalene-3,6- or -6,8-disulfonic acid, 
1-hydroxynaphthalene-4-sulfonic acid, 1-hydroxynaphthalene-4,6- or 
-4,7-disulfonic acid, 1-amino-3-methylbenzene, 
1-amino-2-methoxy-5-methylbenzene, 1-amino-2,5-dimethylbenzene, 
3-aminophenylurea, 1-amino-3-acetylaminobenzene, 
1-amino-3-hydroxyacetylaminobenzene, 1,3-diaminobenzene-4-sulfonic acid, 
1-aminonaphthalene-6- or -8-sulfonic acid, 
1-amino-2-methoxynaphthalene-6-sulfonic acid, 
2-aminonaphthalene-5,7-disulfonic acid, 
1-amino-8-hydroxynaphthalene-4-sulfonic acid, 
1-amino-8-hydroxynaphthalene-6-sulfonic acid, 
1-amino-8-hydroxynaphthalene-2,4-disulfonic acid, 
2-hydroxy-3-aminonaphthalene-5,7-disulfonic acid, 
1-amino-8-hydroxynaphthalene-2,4,6-trisulfonic acid, 
1-hydroxy-8-acetylaminonaphthalene-3-sulfonic acid, 
1-benzoylamino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 
2-benzoylamino-5-hydroxynaphthalene-7-sulfonic acid, 
2-amino-5-hydroxynaphthalene-7-sulfonic acid, 2-methyl- or 
2-ethylamino-5-hydroxynaphthalene-7-sulfonic acid, 
2-(N-acetyl-N-methylamino)-5-hydroxynaphthalene-7-sulfonic acid, 
2-acetylamino-5-hydroxynaphthalene-7-sulfonic acid, 
2-amino-5-hydroxynaphthalene-1,7-disulfonic acid, 
2-amino-8-hydroxynaphthalene-6-sulfonic acid, 2-methyl- or 
-ethylamino-8-hydroxynaphthalene-6-sulfonic acid, 
2-(N-acetyl-N-methylamino)-8-hydroxynaphthalene-6-sulfonic acid, 
2-acetylamino-8-hydroxynaphthalene-6-sulfonic acid, 
2-amino-8-hydroxynaphthalene-3,6-disulfonic acid, 
2-acetylamino-8-hydroxynaphthalene-3,6-disulfonic acid, 
1-amino-5-hydroxynaphthalene-7-sulfonic acid, 
1-amino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 
1-acetylamino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 
1-(4'-aminobenzoylamino)-8-hydroxynaphthalene-3,6- or -4,6-disulfonic 
acid, 1-(4'-nitrobenzoylamino)-8-hydroxynaphthalene-3,6- or 
-4,6-disulfonic acid, 1-(3'-aminobenzoylamino)- 8-hydroxynaphthalene-3,6- 
or -4,6-disulfonic acid, 
1-(3'-nitrobenzoylamino)-8-hydroxynaphthalene-3,6- or 4,6-disulfonic acid, 
2-(4'-amino-3'-sulfophenylamino)-5-hydroxynaphthalene-7-sulfonic acid, 
3-methylpyrazol-5-one, 1-phenyl-3-methyl-5-pyrazolone, 
1-(4'-sulfophenyl)-3-methyl-5-pyrazolone, 
1-(4'-sulfophenyl)-pyrazol-5-one-3-carboxylic acid, 
1-(3'-aminophenyl)-3-methyl-5-pyrazolone, 
1-(2',5'-disulfophenyl)-3-methyl-5-pyrazolone, 
1-(2'-methyl-4'-sulfophenyl)-5-pyrazolone-3-carboxylic acid, 
1-(4',8'-disulfonaphth-2'-yl)-3-methyl-5-pyrazolone, 
1-(5',7'-disulfonaphth-2-yl)-3-methyl-5-pyrazolone, 
1-(2',5'-dichloro-4'-sulfophenyl)-3-methyl-5-pyrazolone, 
3-aminocarbonyl-4-methyl-6-hydroxypyrid-2-one, 1-ethyl-3-cyano- or 
-3-chloro-4-methyl-6-hydroxypyrid-2-one, 
1-ethyl-3,3-sulfomethyl-4-methyl-6-hydroxypyrid-2-one, 
2,4,6-triamino-3-cyanopyridine, 
2-(3'-sulfophenylamino)-4,6-diamino-3-cyanopyridine, 2-( 
2'-hydroxyethylamino)-3-cyano-4-methyl-6-aminopyridine, 
2,6-bis-(2'-hydroxyethylamino)-3-cyano-4-methylpyridine, 
1-ethyl-3-carbamoyl-4-methyl-6-hydroxypyrid-2-one, 
1-ethyl-3-sulfomethyl-4-methyl-5-carbamoyl-6-hydroxypyrid-2-one, 
N-acetoacetylaminobenzene, 
1-(N-acetoacetylamino)-2-methoxybenzene-5-sulfonic acid, 
4-hydroxyquinol-2-one, 
1-amino-8-hydroxy-2-(phenylazo)naphthalene-3,6-disulfonic acid, 
1-amino-8-hydroxy-2-(4'-sulfophenylazo)-naphthalene-3,6-disulfonic acid, 
1-amino-8hydroxy-2-(2',5'-disulfophenylazo)-naphthalene-3,6-disulfonic 
acid, 1-.beta.-aminoethyl-3-cyano-4-methyl-6-hydroxypyrid-2-one, 
1-.gamma.-aminopropyl-3-sulfomethyl-4-methyl-6-hydroxyprid-2-one, 
1,3-diaminobenzene, 1-amino-3-N,N-di-.beta.-hydroxyethylaminobenzene, 
1-amino-3-N,N-di-.beta.-sulfatoethylaminobenzene, 
1-amino-3-N,N-di-.beta.-hydroxyethylamino-4-methoxybenzene, 
1-amino-3-N,N-di-.beta.-sulfatoethylamino-4-methoxybenzene, 
1-amino-3-sulfobenzylaminobenzene, 
1-amino-3-sulfobenzylamino-4-chlorobenzene and 
1-amino-3-N,N-disulfobenzylaminobenzene. 
Pyrimidines of the formula (10) 
2,4,5,6-tetrachloropyrimidine, 2,4,5,6-tetrafluoropyrimidine, 
2,4,5,6-tetrabromopyrimidine, 2,4,6-trichloro-5-methylsulfinylpyrimidine, 
2,4,6-trifluoro-5-methylsulfinylpyrimidine, 
2,4,6-tribromo-5-methylsulfinylpyrimidine, 
2,4,6-trichloro-5-ethylsulfinylpyrimidine, 
2,4,6-trichloro-5-n-propylsulfinylpyrimidine, 
2,4,6-trichloro-5-n-butylsulfinylpyrimidine, 
2,4,6-trichloro-5-isopropylsulfinylpyrimidine, 
2,4,6-trichloro-5-tert.-butylsulfinylpyrimidine, 
2,4,6-trichloro-5-methylsulfonylpyrimidine, 
2,4,6-tribromo-5-methylsulfonylpyrimidine, 
2,4,6-trifluoro-5-methylsulfonylpyrimidine, 
2,4,6-trichloro-5-ethylsulfonylpyrimidine, 
2,4,6-trichloro-5-isopropylsulfonylpyrimidine, 
2,4,6-trichloro-5-n-butylsulfonylpyrimidine, 
2,4,6-trichloro-5-chloromethylsulfonylpyrimidine, 
2,4,6-trichloro-5-.beta.-chloroethylsulfonylpyrimidine, 
2,4,6-trichloro-5-trifluoromethylsulfonylpyrimidine, 
2,4,6-trichloro-5-perfluorobutylsulfonylpyrimidine, 
2,4,6-trichloro-5-ethoxymethylsulfonylpyrimidine, 
2,4,6-trifluoro-5-ethoxyethylsulfonylpyrimidine, 
2,4,6-tribromo-5-isopropoxymethylsulfonylpyrimidine, 
2,4,6-trichloro-5-benzylsulfonylpyrimidine, 
2,4,6-tribromo-5-benzylsulfonylpyrimidine, 
2,4,6-trifluoro-5-benzylsulfonylpyrimidine, 
2,4,6-trichloro-5-phenethylsulfonylpyrimidine, 
2,4-dichloro-6-bromo-5-methylsulfonylpyrimidine, 
2,4-dichloro-6-fluoro-5-methylsulfonylpyrimidine, 
2,4-dichloro-6-fluoro-5-methylsulfonylpyrimidine, 
2-chloro-4,6-difluoro-5-methylsulfonylpyrimidine, 
2-chloro-4,6-dibromo-5-methylsulfonylpyrimidine, 
2-bromo-4,6-difluoro-5-methylsulfonylpyrimidine, 
2-chloro-4,6-difluoro-5-ethylsulfonylpyrimidine, 
2,4,6-trichloro-5-carboxypyrimidine, 2,4,6-trifluoro-5-carboxypyrimidine 
and 2,4,6-trichloro-5-cyanopyrimidine. 
2,4,6-Trifluoro-5-methylsulfonylpyrimidine is preferred. 
Amines of the formula (11) 
1-Aminophenyl-2-, -3- or -4-.beta.-sulfatoethyl sulfone, 
1-aminophenyl-3-.beta.-phosphatoethyl sulfone, 
1-amino-4-methylphenyl-3-.beta.-sulfatoethyl sulfone, 
1-aminophenyl-3-.beta.-chloroethyl sulfone, 
1-amino-4-methoxyphenyl-3-.beta.-sulfatoethyl sulfone, 
1-amino-2-sulfophenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2-sulfophenyl-5-.beta.-sulfatoethyl sulfone, 
1-amino-2,4-disulfophenyl-5-.beta.-sulfatoethyl sulfone, 
1-aminonaphthalene-4-.beta.-sulfatoethyl sulfone, 
1-amino-2,5-dimethoxyphenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2-carboxylphenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2-carboxylphenyl-5-.beta.-sulfatoethyl sulfone, 
1-amino-2-methoxyphenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2-chorophenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2-methoxyphenyl-5-.beta.-sulfatoethyl sulfone, 
2-aminonaphthyl-8-.beta.-sulfatoethyl sulfone, 
2-amino-6-sulfonaphthyl-8-.beta.-sulfatoethyl sulfone, 
1-amino-2,5-dimethoxyphenyl-4-vinyl sulfone, 
1-amino-2-methoxy-5-methylphenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2,5-diethoxyphenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2-bromophenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-2-bromophenyl-4-vinyl sulfone, 1-amino-2,4 -disulfophenyl-5-vinyl 
sulfone, 1-amino-2,4-disulfophenyl-5-.beta.-phosphatoethyl sulfone, 
1-amino-2,4-disulfophenyl-5-.beta.-chloroethyl sulfone, 
2-amino-6-sulfonaphthyl-8-.beta.-phosphatoethyl sulfone, 
2-amino-6-sulfonaphthyl-8-vinyl sulfone, 
1-amino-2-methoxy-5-methylphenyl-4-.beta.-chloroethyl sulfone, 
2-aminophenol-4-.beta.-sulfatoethyl sulfone, 1-aminophenyl-3- or -4-vinyl 
sulfone, 1-amino-2-hydroxyphenyl-4-.beta.-sulfatoethyl sulfone, 
1-amino-5-vinyl sulfone-2-sulfonic acid 
3-(N-methyl-.beta.-sulfatoethylsulfonyl-amino)-1-aminobenzene, 
3-(N-ethyl-.beta.-sulfatoethylsulfonyl-amino)-1-aminobenzene and 
3-.beta.-sulfatoethylsulfonylamino-1-aminobenzene. 
1-Aminobenzene-3-.beta.-sulfatoethyl sulfone is preferred. 
.beta.-(.beta.-Chloroethylsulfonyl)-ethylamine, 
.beta.-(.beta.-bromoethylsulfonyl)-ethylamine, 
.beta.-vinylsulfonylethylamino), 
.gamma.-(.beta.-chloroethylsulfonyl)-propylamine, 
.alpha.-(.beta.-chloroethylsulfonyl)-isopropylamine, 
.delta.-(.beta.-chloroethylsulfonyl)-butylamine, 
.beta.-(.beta.-chloroethylsulfonyl)-isobutylamine, 
.epsilon.-(.beta.-chloroethylsulfonyl)-pentylamine, 
.beta.-(.beta.-chloroethylsulfonyl)-hexylamine, 
N-methyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-ethyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-propyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-butyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-pentyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-hexyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-nonyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-dodecyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-hexadecyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-octadecyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-carboxymethyl-N-.beta.-(.beta.-bromoethylsulfonyl)-ethylamine, 
N-sulfatomethyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-.beta.-carboxyethyl-N-.gamma.-(.beta.-chloroethylsulfonyl)-propylamine, 
N-.beta.-sulfatoethyl-N-.delta.-(.beta.-chloroethylsulfonyl)-propylamine, 
N-.beta.-sulfatoethyl-N-.delta.-(.beta.-chloroethylsulfonyl)-butylamine, 
N-.beta.-ethoxyethyl-N-.delta.-(.beta.-chloroethylsulfonyl)-butylamine, 
N-.gamma.-chloropropyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-phenyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-p-chlorophenyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-o-methylphenyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-p-methoxyphenyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-m-sulfophenyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
N-p-sulfophenyl-N-.beta.-(.beta.-chloroethylsulfonyl)-ethylamine, 
bis-[(.beta.-(.beta.-chloroethylsulfonyl)ethyl]-amine, 
bis-[.beta.-(.beta.-bromoethylsulfonyl)-ethyl]-amine, 
bis-[.gamma.-(.beta.-chloroethylsulfonyl)-propyl]-amine, 
bis-[.delta.-(.beta.-chloroethylsulfonyl)-butyl] -amine and 
bis-(.beta.-vinylsulfonylethyl)-amine. 
Preference is given to amines of low molecular weight, such as 
.beta.-(.beta.-chloroethylsulfonyl)-ethylamine and its N-methyl 
derivative. bis-[.beta.-(.beta.-Chloroethylsulfonyl)-ethyl]-amine is also 
preferred. 
.beta.-(.beta.-Hydroxyethylsulfonyl)-ethylamine (2-taurylethanol), 
.gamma.-(.beta.-hydroxyethylsulfonyl)-propylamine, 
.alpha.-(.beta.-hydroxyethylsulfonyl)-isopropylamine, 
.delta.-(.beta.-hydroxyethylsulfonyl)-butylamine, 
.beta.-(.beta.-hydroxyethylsulfonyl)-isobutylamine, 
.epsilon.-(.beta.-hydroxyethylsulfonyl)-pentylamine, 
.beta.-(.beta.-hydroxyethylsulfonyl)-hexylamine, 
N-methyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-ethyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-propyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-butyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-pentyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-hexyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-nonyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-dodecyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-hexadecyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-octadecyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-carboxymethyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-sulfatomethyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-.beta.-carboxymethyl-N-.gamma.-(.beta.-hydroxyethylsulfonyl)-propylamine 
, N-.beta.-sulfatoethyl-N-.gamma.-(.beta.-hydroxyethylsulfonyl)-propylamine 
, N-.beta.-sulfatoethyl-N-.delta.-(.beta.-hydroxyethylsulfonyl)-butylamine, 
N-.beta.-ethoxyethyl-N-.delta.-(.beta.-hydroxyethylsulfonyl)-butylamine, 
N-.gamma.-chloropropyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-phenyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-p-chlorophenyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-o-methylphenyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-p-methoxyphenyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-m-sulfophenyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
N-p-sulfophenyl-N-.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine, 
bis-[.beta.-(.beta.-hydroxyethylsulfonyl)-ethyl]-amine, 
bis-[.gamma.-(.beta.-hydroxyethylsulfonyl)-propyl]-amine, 
bis[.delta.-(.beta.-hydroxyethylsulfonyl)-butyl]-amine, and the 
corresponding sulfated compounds. 
Reference is given to amines of low molecular weight, such as 
.beta.-(.beta.-hydroxyethylsulfonyl)-ethylamine and its N-methyl 
derivative. bis-[.beta.-(.beta.-Hydroxyethylsulfonyl)-ethyl]-amine and the 
corresponding sulfated compounds are also preferred. 
Diazo components or the intermediates containing a diazotisable amino group 
are generally diazotised at low temperatures in aqueous mineral acid 
solutions through the action of nitrous acid. The coupling onto the 
coupling component takes place at strongly acid, neutral or weakly 
alkaline pH. 
The pyrimidines of the formula (10) are preferably condensed with the diazo 
components and the coupling components and with the amines or with 
acylatable monoazo or disazo intermediates or with the amino-containing 
dyes at low temperatures and at weakly acid, neutral or weakly alkaline pH 
in aqueous solutions or suspensions. The hydrogen halide liberated in the 
course of the condensation is advantageously continuously neutralised by 
adding aqueous alkali metal hydroxides, carbonates or bicarbonates. 
The reactive dyes of the formula (1) are suitable for dyeing and printing a 
very wide variety of different materials, such as silk, leather, wool, 
nylon fibres and polyurethanes, and in particular cellulose-containing 
fibre materials of any kind. Examples of such fibre materials are the 
natural cellulose fibres, such as cotton, linen and hemp, as well as pulp 
and regenerated cellulose. The reactive dyes of the formula (1) are also 
suitable for dyeing or printing hydroxy-containing fibres contained in 
blend fabrics, for example blends of cotton with polyester fibres or nylon 
fibres. 
The dyes according to the invention can be applied to the fibre material 
and fixed on the fibre in various ways, in particular in the form of 
aqueous dye solutions and print pastes. They are suitable not only for the 
exhaust method of dyeing but also for dyeing by the pad-dyeing method 
whereby the cloth is impregnated with aqueous dye solutions which can, if 
desired, also contain salt, and the dyes are fixed, if desired under heat, 
after a treatment with alkali or in the presence of alkali. They are 
particularly suitable for the so-called cold pad-batch method whereby the 
dye is applied on a pad-mangle together with the alkali and is then fixed 
through several hours' storage at room temperature. After the fixing the 
dyeings or prints are thoroughly rinsed with cold and hot water which can, 
if desired, also contain an agent acting like a dispersant and promoting 
the diffusion of the unfixed portions. 
The reactive dyes of the formula (1) are distinguished by high reactivity 
and good fixing properties. They can therefore be used in exhaust dyeing 
at low dye temperatures and require only short steaming times in the 
pad-steam process. The degrees of fixation are high, and the unfixed 
portions are readily washed off, the difference between the degree of 
exhaustion and the degree of fixation being remarkably small, i.e. the 
hydrolysis loss being very low. The reactive dyes of the formula (1) are 
also suitable for printing, especially on cotton, but also for printing 
nitrogen-containing fibres, for example wool, silk or wool-containing 
blend fabrics. 
The dyeings and prints prepared with the dyes according to the invention 
are distinguished in that the dyeings and prints on cellulose fibre 
materials are of high tinctorial strength and have a high fibredye bond 
stability not only in the acid but also in the alkaline range, and also 
good lightfastness and very good wet-fastness properties, such as wash, 
water, sea water, cross-dyeing and perspiration fastness properties, as 
well as a good fastness to pleating, hot-press fastness and rub fastness.

The following Examples serve to illustrate the invention. The temperatures 
are given in degrees centigrade. The parts and percentages are by weight, 
unless otherwise stated. Parts by weight relate to parts by volume as the 
kilogram relates to the liter. 
The preparation of monoazo or disazo intermediates has not been described 
in all cases in the following illustrative embodiments, but it is anyhow 
readily apparent from the general description. 
EXAMPLE 1 
5.45 parts of the dye of the formula 
##STR19## 
are dissolved in 100 parts of water under neutral conditions, and 50 parts 
of ice are added, followed with vigorous stirring by a solution of 2.12 
parts of 2,4,6-trifluoro-5-methylsulfonylpyrimidine in 20 parts of 
acetone. The solution is brought back to pH 7 by the dropwise addition of 
about 11 parts of 1N sodium hydroxide solution. After the complete 
acylation of the amino group the solution of the difluoro compound has 
added to it a neutral solution of 2.81 parts of 
1-aminophenyl-3-.beta.-sulfatoethyl sulfone in 50 parts of water, the 
temperature is raised to 30.degree. to 35.degree., and the solution is 
kept at pH 5-6 by the dropwise addition of 1N sodium hydroxide solution. 
As soon as the second condensation has ended, the monofluoropyrimidine dye 
formed is salted out with potassium chloride, is filtered off and is dried 
at 40.degree. to 50.degree. in vacuo. 
The dye thus obtained dyes cotton gold yellow shades. 
EXAMPLE 2 
5.53 parts of the dye of the formula 
##STR20## 
are dissolved in 100 parts of water under neutral conditions, and 50 parts 
of ice are added, followed with vigorous stirring by a solution of 2.12 
parts of 2,4,6-trifluoro-5-methylsulfonylpyrimidine in 20 parts of 
acetone. The solution is brought back to pH 7 by the dropwise addition of 
about 11 parts of 1N sodium hydroxide solution. After the complete 
acylation of the amino group the solution of the difluoropyrimidine dye 
has added to it 2.07 parts of 
.beta.-(.beta.-chloroethylsulfonyl)-ethylamine hydrochloride, the 
temperature is raised to 30.degree. to 35.degree., and the solution is 
held at pH 5-6 by the dropwise addition of about 9 parts of 1N sodium 
hydroxide solution. After the condensation has ended the dye formed is 
salted out by adding 25 parts by volume of sodium chloride, is filtered 
off and is dried at 40.degree. to 50.degree. in vacuo. 
The dye thus obtained dyes cotton in orange shades. 
EXAMPLE 3 
A solution of 2.12 parts of 2,4,6-trifluoro-5-methylsulfonylpyrimidine in 
20 parts of acetone is added with vigorous stirring to a neutral solution 
of 3.61 parts of bis-[.beta.-(.beta.-chloroethylsulfonyl)-ethyl]-amine 
hydrochloride in 100 parts of ice-water, and the solution is brought back 
to pH by the dropwise addition of about 10 parts of 1N sodium hydroxide 
solution. This neutral solution of the primary condensation product then 
has added to it a neutral solution of 4.38 parts of the dye of the formula 
##STR21## 
The reaction mixture is raised to 30.degree. to 35.degree., and the 
solution is held at pH 5-6 by the dropwise addition of about 10 parts of 
1N sodium hydroxide solution. After the acylation has ended the 
monofluoropyrimidine dye formed is salted out with sodium chloride, is 
filtered off and is dried at 40.degree. to 50.degree. C. in vacuo. 
The dye thus obtained dyes cotton in bluish red shades. 
The condensation of 2,4,6-trifluoro-5-methylsulfonylpyrimidine with the 
amino-containing dyes of column I and the amines of column II as described 
in Examples 1 to 3 gives further monofluoropyrimidine dyes which dye 
cotton in the shades indicated in column III. 
__________________________________________________________________________ 
I II III 
__________________________________________________________________________ 
##STR22## 1-aminophenyl- 3-.beta.- 
sulfatoethyl sulfone 
scarlet 
" 1-aminophenyl- 
scarlet 
4-.beta.-sulfatoethyl 
sulfone 
##STR23## 1-aminophenyl- 4-.beta.- 
sulfatoethyl sulfone 
greenish 
yellow 
" .beta.-(.beta.-chloro- 
greenish 
ethylsulfonyl)- 
yellow 
ethylamine 
##STR24## .beta.-(.beta.-chloro- 
thylsulfonyl)- ethylamin 
e greenish 
yellow 
##STR25## 1-aminophenyl- 3-.beta.- 
sulfatoethyl sulfone 
yellow 
" .beta.-(.beta.-chloro- 
yellow 
ethylsulfonyl)- 
ethylamine 
##STR26## .beta.-(.beta.-chloro- 
ethylsulfonyl)- 
propylamine 
yellow 
" bis-[.beta.-(.beta.- 
yellow 
chloroethyl- 
sulfonyl)- 
ethyl]-amine 
##STR27## .beta.-(.beta.-sulfato 
ethylsulfonyl)- 
ethylamine 
scarlet 
##STR28## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e golden yellow 
##STR29## .beta.-vinylsulfonyl- 
ethylamine 
orange 
" .beta.-(.beta.-chloro- 
orange 
ethylsulfonyl)- 
ethylamine 
##STR30## .beta.-(.beta.-chloro- 
ethylsulfonyl)- 
ethylamine 
bluish red 
##STR31## .beta.-(.beta.-chloro- 
ethylsulfonyl)- 
ethylamine 
blue 
##STR32## bis-[.beta.-(.beta.- 
chloroethyl- sulfonyl)- 
thyl]-amine 
brown 
##STR33## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e yellow 
##STR34## Nmethyl- N.beta.-(.beta. 
- chloroethyl- sulfonyl) 
- ethylamine 
bluish red 
##STR35## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e dark blue 
##STR36## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e greenish navy 
##STR37## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e greenish blue 
##STR38## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e violet 
##STR39## .beta.-vinylsulfonyl- 
ethylamine 
blue 
##STR40## 1-aminophenyl- 3-vinyl 
sulfone reddish blue 
##STR41## 1-aminophenyl- 4-vinyl 
sulfone blue 
##STR42## .beta.-(.beta.-chloro- 
ethylsulfonyl)- 
ethylamine 
greenish blue 
##STR43## .beta.-(.beta.-chloro- 
ethylsulfonyl)- 
ethylamine 
Royal blue 
##STR44## .beta.-(.beta.-thiosulfa 
to- ethylsulfonyl)- 
ethylamine 
Royal blue 
" .beta.-(.beta.-acetoxy- 
Royal 
ethylsulfonyl)- 
blue 
ethylamine 
##STR45## .beta.-(.beta.-acetoxy- 
thylsulfonyl)- ethylamin 
e yellow 
##STR46## .beta.-(.beta.-acetoxy- 
thylsulfonyl)- ethylamin 
e bluish red 
##STR47## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e bluish red 
##STR48## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e bluish red 
##STR49## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e turquoise 
##STR50## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e turquoise 
##STR51## .beta.-(.beta.-acetoxy- 
thylsulfonyl)- ethylamin 
e red 
##STR52## .beta.-(.beta.-acetoxy- 
thylsulfonyl)- ethylamin 
e yellow 
##STR53## .beta.-(.beta.-chloro- 
ethylsulfonyl)- 
ethylamine 
yellow 
##STR54## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e blue 
##STR55## .beta.-(.beta.-chloro- 
ethylsulfonyl)- 
ethylamine) 
yellow 
##STR56## 1-aminophenyl- 4-.beta.- 
sulfatoethyl sulfone 
yellow 
##STR57## 1-aminophenyl- 4-.beta.- 
sulfatoethyl sulfone 
blue 
##STR58## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e bluish red 
##STR59## .beta.-(.beta.-sulfato- 
thylsulfonyl)- ethylamin 
e yellow 
__________________________________________________________________________ 
EXAMPLE 4 
A solution of 21 parts of 2,4,6-trichloro-5-methylsulfonylpyrimidine in 80 
parts of acetone is added at room temperature with vigorous stirring to a 
neutral solution of 50.64 parts of the aminoazo dye of the formula 
##STR60## 
in 900 parts of water, and the mixture is left to react overnight. The 
next day the solution is brought to pH 7 with 2N sodium hydroxide solution 
and is clarified by filtering. The dye of the formula 
##STR61## 
is salted out by adding 20% by volume of sodium chloride and is filtered 
off. The dye paste thus obtained is dissolved in 600 parts of water, and 
the solution has gradually added to it a solution of 16.3 parts of 
.beta.-(.beta.-chloroethylsulfonyl)ethylamine hydrochloride in 60 parts of 
water, while the solution is held at pH 7-8 with 1N sodium hydroxide 
solution. 
After the amidation has ended the dye of the formula 
##STR62## 
is salted out with potassium chloride, is filtered off and is dried at 
40.degree. to 50.degree. C. in vacuo. The dye thus obtained dyes cotton in 
the cold pad-batch method in bluish red shades. 
The condensation of 2,4,6-trichloro-5-methylsulfonylpyrimidine with the 
amino groups-containing dyes of column I and the amines of column II as 
described in the above example gives further dyes which dye cotton in the 
shades indicated in column III. 
__________________________________________________________________________ 
I II III 
__________________________________________________________________________ 
##STR63## .beta.-(.beta.-chloroethyl- 
sulfonyl)-ethylamine 
bluish red 
##STR64## .beta.-(.beta.-chloroethyl- 
sulfonyl)-ethylamine 
golden yellow 
##STR65## .beta.-(.beta.-chloroethyl- 
sulfonyl)-ethylamine 
navy 
##STR66## .beta.-(.beta.-chloroethyl- 
sulfonyl)-ethylamine 
navy 
##STR67## .beta.-(.beta.-chloroethyl- 
sulfonyl)-ethylamine 
navy 
##STR68## bis-[.beta.-(.beta.-chloroethyl- 
sulfonyl)ethyl]-amine 
bluish red 
" 1-aminophenyl-3-.beta.- 
bluish 
sulfatoethyl sulfone 
red 
##STR69## 1-aminophenyl-3-.beta.- sulfatoeth 
yl sulfone navy 
__________________________________________________________________________ 
EXAMPLE 5 
12.76 parts of 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid are 
suspended at room temperature in 500 parts of water, and the suspension is 
brought to pH 6 with sodium hydroxide solution. The resulting solution has 
added to it a solution of 10.5 parts of 
2,4,6-trichloro-5-methylsulfonylpyrimidine in 40 parts of acetone, and the 
mixture is vigorously stirred overnight. The next day the coupling 
component of the formula 
##STR70## 
is clarified by filtering and is gradually added to a suspension of the 
diazonium salt prepared in conventional manner from 11.24 parts of 
1-aminophenyl-4-.beta.-sulfatoethyl sulfone, 20 parts of 2N sodium nitrate 
solution and 12 parts of 10N hydrochloric acid. The coupling mixture is 
slowly brought to pH 5 by the dropwise addition of 1N sodium hydroxide 
solution. After the coupling has ended the compound of the formula 
##STR71## 
is salted out with 25% by volume of sodium chloride and is filtered off. 
The dye paste obtained is then dissolved in 300 parts of water, and the 
solution has gradually added to it a solution of 8.32 parts of 
.beta.-(.beta.-chloroethylsulfonyl)-ethylamine hydrochloride in 30 parts 
of water, while pH 7-8 is maintained by the dropwise addition of 1N sodium 
hydroxide solution. After the amidation has ended the dye of the formula 
##STR72## 
is evaporated to dryness at 40.degree. C. 
The dye thus obtained dyes cotton in the cold pad-batch method in bluish 
red shades. 
EXAMPLE 6 
28.91 parts of the amine of the formula 
##STR73## 
are diazotised in a conventional manner with nitrite and hydrochloric acid 
and are coupled at pH 3 onto 22.33 parts of 
1-amino-8-hydroxynaphthalene-3,6-disulfonic acid. The red monoazo dye of 
the formula 
##STR74## 
is isolated by adding 10% by volume of sodium chloride. 
The dye paste obtained is suspended in 500 parts of water, and the 
suspension is gradually added to a suspension of a diazonium salt prepared 
in a conventional manner from 19.67 parts of 
1-aminophenyl-4-.beta.-sulfatoethyl sulfone, 35 parts of 2N sodium 
nitrite solution and 18 parts of 10N hydrochloric acid. The coupling 
mixture is gradually brought to pH 7 by the dropwise addition of 1N sodium 
hydroxide solution. The disazo dye of the formula 
##STR75## 
is salted out by sprinkling in 15% by volume of sodium chloride and is 
filtered off. 
Amidation of this product with 14.56 parts of 
.beta.-(.beta.-chloroethylsulfonyl)-ethylamine hydrochloride finally leads 
to a dye of the formula 
##STR76## 
The dye thus obtained dyes cotton in the cold pad-batch method in navy 
shades. 
EXAMPLE 7 
A diazonium salt prepared in conventional manner from 15.38 parts of the 
amine of the formula 
##STR77## 
using 20 parts of 2N sodium nitrite solution and 12 parts of 10N 
hydrochloric acid is added to a solution of 21.76 parts of the coupling 
component of the formula 
##STR78## 
whose preparation is described in Example 5. The coupling mixture is 
gradually brought the pH 5 by the dropwise addition of 2N sodium hydroxide 
solution. After the coupling has ended the dye of the formula 
##STR79## 
is salted out with 15% by volumes of sodium chloride and is filtered off. 
The dye paste, in 500 parts of water, is then neutralised with sodium 
hydroxide solution and is amidated with 8.32 parts of 
.beta.-(.beta.-chloroethylsulfonyl)-ethylamine hydrochloride. 
The dye thus obtained has the formula 
##STR80## 
is evaporated to dryness and dyes cotton in the cold pad-batch method red 
shades. 
Dyeing method I 
2 parts of the dye obtained in Example 1 are dissolved in 400 parts of 
water; to this solution are added 1,500 parts of a solution which contains 
per liter 53 g of sodium chloride. 100 parts of a cotton fabric are 
introduced at 40.degree. C. into this dyebath. After 45 minutes 100 parts 
of a solution which contains per liter 16 g of sodium hydroxide and 20 g 
of calcined sodium carbonate are added. The temperature of the dyebath is 
held at 40.degree. C. for a further 45 minutes. The dyed fabric is then 
rinsed, is soaped off at the boil with a nonionic detergent for a quarter 
of an hour, is rinsed once more and is dried. 
Dyeing method II 
2 parts of the reactive dye obtained in Example 1 are dissolved in 400 
parts of water; to this solution are added 1,500 parts of a solution which 
contains per liter 53 g of sodium chloride. 100 parts of a cotton fabric 
are introduced at 35.degree. C. into this dyebath. After 20 minutes 100 
parts of a solution which contains per liter 16 g of sodium hydroxide and 
20 g of calcined sodium carbonate are added. The temperature of the 
dyebath is held at 35.degree. C. for a further 15 minutes. The temperature 
is then raised to 60.degree. C. in the course of 20 minutes. The 
temperature is held at 60.degree. C. for a further 35 minutes. The fabric 
is then rinsed, is soaped off at the boil with a nonionic detergent for a 
quarter of an hour, is rinsed once more and is dried. 
Dyeing method III 
8 parts of the reactive dye obtained in Example 1 are dissolved in 400 
parts of water; to this solution are added 1,400 parts of a solution which 
contains per liter 100 g of sodium sulfate. 100 parts of a cotton fabric 
are introduced at 25.degree. C. into this dyebath. After 10 minutes 200 
parts of a solution which contains per liter 150 g of trisodium phosphate 
are added. The temperature of the dyebath is then raised to 60.degree. C. 
in the course of 10 minutes. The temperature is held at 60.degree. C. for 
a further 90 minutes. The fabric is then rinsed, is soaped off at the boil 
with a nonionic detergent for a quarter of an hour, is rinsed once more 
and is dried. 
Dyeing method IV 
4 parts of the reactive dye obtained in Example 1 are dissolved in 50 parts 
of water; to this solution are added 50 parts of a solution which contains 
per liter 5 g of sodium hydroxide and 20 g of calcined sodium carbonate. 
The resulting solution is applied to a cotton fabric on a pad-mangle in 
such a way that its weight increases by 70%, and the fabric is then wound 
onto a beam. In this state the cotton fabric is left to stand at room 
temperature for 3 hours. The dyed fabric is then rinsed, is soaped off at 
the boil with a nonionic detergent for a quarter of an hour, is rinsed 
once more and is dried. 
Dyeing method V 
6 parts of the reactive dye obtained in Example 1 are dissolved in 50 parts 
of water; to this solution are added 50 parts of a solution which contains 
per liter 16 g of sodium hydroxide and 0.04 liter of 38.degree. Be sodium 
silicate. The resulting solution is applied to a cotton fabric on a 
pad-mangle in such a way that its weight increases by 70%, and the fabric 
is then wound on to a beam. In this state the cotton fabric is left at 
room temperature for 10 hours. The dyed fabric is then rinsed, is soaped 
off at the boil with a nonionic detergent for a quarter of an hour, is 
rinsed once more and is dried. 
Dyeing method VI 
2 parts of the reactive dye obtained in Example 1 are dissolved in 100 
parts of water in the presence of 0.5 part of sodium 
m-nitrobenzenesulfonate. The resulting solution is used to impregnate a 
cotton fabric in such a way that its weight increases by 75%, and the 
fabric is then dried. The fabric is then impregnated with a warm solution 
at 20.degree. C. which contains per liter 4 g of sodium hydroxide and 300 
g of sodium chloride, and is squeezed to a 75% weight increase and the 
dyeing is steamed at 100.degree. to 102.degree. C. for 30 seconds, is 
rinsed, is soaped off at the boil with a 0.3% strength solution of a 
nonionic detergent for a quarter of an hour, is rinsed and is dried. 
Printing method I 
3 parts of the reactive dye obtained in Example 1 are sprinkled with 
high-speed stirring into 100 parts of a stock thickening containing 50 
parts of 5% strength sodium alginate thickening, 27.8 parts of water, 20 
parts of urea, 1 part of sodium m-nitrobenzenesulfonate and 1.2 parts of 
sodium hydrogencarbonate. The print paste thus obtained is used to print a 
cotton fabric, which is then dried, and the resulting printed fabric is 
steamed at 102.degree. C. in saturated steam for 2 minutes. The printed 
fabric is then rinsed, if desired soaped off at the boil and rinsed once 
more, and is then dried. 
Printing method II 
5 parts of the reactive dye obtained in Example 1 are sprinkled with 
high-speed stirring into 100 parts of a stock thickening containing 50 
parts of 5% strength sodium alginate thickening, 36.5 parts of water, 10 
parts of urea, 1 part of sodium n-nitrobenzenesulfonate and 2.5 parts of 
sodium hydrogencarbonate. The print paste thus obtained, whose stability 
meets industrial requirements, is used to print a cotton fabric, which is 
then dried, and the resulting printed fabric is steamed at 102.degree. C. 
in saturated steam for 8 minutes. The printed fabric is then rinsed, if 
desired soaped off at the boil and rinsed once more, and is then dried.