Fiber-reactive dyes comprising a halopyrimidine for which a vinylsulfonyl or the like moiety is attached via a bridge member

A reactive dye of the formula ##STR1## in which Fa 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, T is a negative substituent, one X is a detachable substituent and the other X is a group of the formula ##STR2## A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z, Z is a --CH.dbd.CH.sub.2 or CH.sub.2 --Y radical and Y is an inorganic or organic radical which is detachable under alkaline conditions, q, m and n are independently of one another an integral number from 2 to 6, R and R' are independently of one another hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2. The inventive dyes are especially suitable for dyeing and printing cellulose-containing fiber materials by the cold pad-batch method.

The present invention relates to novel reactive dyes, to processes for 
their preparation and to the use thereof for dyeing or printing fibre 
materials. 
The practice of dyeing with reactive dyes has recently led to increased 
demands on the quality of the dyeings and on the economics of the dyeing 
process. There consequently continues to be a demand for new reactive dyes 
which have improved properties, in particular in respect of application. 
The present demand in the dyeing of cotton by the cold pad-batch method is 
for reactive dyes which have adequate substantivity at the low dyeing 
temperature and which also have good wash-off properties in respect of the 
unfixed portions. They should further have a high reactivity, so that only 
short batching times are required, and they should in particularly produce 
dyeings of high degrees of fixation. These demands are met only 
inadequately by known dyes. 
The present invention therefore has for its object to fixed new, improved 
reactive dyes for the cold pad-batch method which have the 
above-characterized qualities to a high degree. The new dyes should be 
distinguished in particular by high degrees of fixation and high fibre-dye 
bond stabilities, and moreover the portions not fixed on the fibre should 
be easy to wash off. They should further produce dyeings having good 
allround fastness properties, for example light and wet fastness 
properties. 
It is has been found that this object is achieved with the novel reactive 
dyes defined hereinafter. 
The invention accordingly provides reactive dyes of the formula 
##STR3## 
in which Fa is the radical of an organic dye of the monoazo, polyazo, 
metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, 
dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, 
nitroraryl, naphthoquinone, pyrenequinone or perylenetetracarbimide 
series, T is a negative substituent, one X is a detachable substituent and 
the other X is a group of the formula 
##STR4## 
A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 
-C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q 
--SO.sub.2 --Z,Z is a --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y 
radical and Y is an inorganic or organic radical which is detachable under 
alkaline conditions, q, m and n are independently of one another an 
integer from 2 to 6, R and R' are independently of one another hydrogen or 
substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2. 
The Fa radical in formula (1) can contain bonded to its skeleton the 
substituents customary with organic dyes. 
Examples of suitable substituents in the Fa radical are: C.sub.1 -C.sub.4 
alkyl, which generally comprises methyl, ethyl, n-propyl, isopropyl, 
n-butyl, sec-butyl and tert-butyl; C.sub.1 -C.sub.4 alkoxy, which is to be 
understood as meaning is general methoxy, ethoxy, n-propoxy, isopropoxy, 
n-butoxy, sec-butoxy and tert-butoxy; C.sub.1 -C.sub.4 alkanoylamino, in 
particular acetylamino and propionylamino; benzoylamino; amino; N-mono- or 
N,N-di-C.sub.1 -C.sub.4 -alkylamino, where the alkyl can be further 
substituted, for example by --OH, --OCOCH.sub.3, --OSO.sub.3 H, --CN or 
halogen, e.g. methylamino, ethylamino, n-propylamino or iso-propylamino, 
n-, sec- or tert-butylamino, N,N-di-.beta.-hydroxyethylamino, 
N,N-di-.beta.-sulfatoethylamino, hydroxypropylamino, 
.beta.-sulfatoethylamino, .beta.-chloroethylamino, 
.beta.-acetyloxyethylamino; phenylamino; mono- or di-sulfobenzylamino; 
C.sub.1 -C.sub.4 alkoxycarbonyl, e.g. methoxycarbonyl or ethoxycarbonyl; 
C.sub.1 -C.sub.4 alkylsulfonyl, e.g. methylsulfonyl or ethylsulfonyl; 
trifluoromethyl; nitro; cyano; halogen, which is to be understood as 
meaning in general fluorine, chlorine and bromine; carbamoyl; N-mono- or 
N,N-di-C.sub.1 -C.sub.4 alkylcarbamoyl; sulfamoyl; N-mono- or 
N,N-di-C.sub.1 -C.sub.4 -alkylsulfamoyl; N-(.beta.-hydroxyethyl)sulfamoyl; 
N,N-di-(.beta.-hydroxyethyl)sulfamoyl; N-phenylsulfamoyl; hydroxyl; 
carboxyl; sulfo; sulfomethyl; ureido. 
Fa is preferably the radical of an organic dye of the monoazo, polyazo, 
metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine 
series which is substituted by one or more of the abovementioned radicals. 
Particularly preferably the Fa radical contains one or more sulfo groups 
and can be further substituted by one or more of the abovementioned 
radicals. 
A monoazo or disazo dye radical Fa is substituted particularly preferably 
by one or more radicals selected from the group consisting of methyl, 
ethyl, methoxy, ethoxy, acetylamino, benzoylamino, amino, chlorine, 
bromine, ureido, hydroxyl, carboxyl, sulfomethyl and sulfo. 
A substituted C.sub.1 -C.sub.4 alkyl radical R and/or R' can be for example 
a halogen-, hydroxyl-, cyano-, carboxyl-, sulfo-, sulfato-, C.sub.1 
-C.sub.4 alkoxycarbonyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.1 
-C.sub.4 alkyl radical. 
Examples of substituted C.sub.1 -C.sub.4 alkyl radicals are: carboxymethyl 
.beta.-carboxyethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 
.beta.-methoxyethyl, .beta.-ethoxyethyl, .beta.-chloroethyl, 
.gamma.-bromopropyl, .beta.-hydroxyethyl, .beta.-hydroxybutyl, 
.beta.-cyanomethyl, sulfomethyl, .beta.-sulfoethyl and 
.beta.-sulfatoethyl. 
R and R' are preferably independently of one another methyl or ethyl and in 
particular hydrogen. 
The radical T is to be understood as meaning a substituent having an (--I) 
and/or (--M) effect. 
Examples of suitable negative substituents T are: nitro, cyano, C.sub.1 
-C.sub.4 -alkylsulfonyl, in particular methylsulfonyl or ethylsulfonyl, 
carboxyl, chlorine, C.sub.1 -C.sub.4 alkoxysulfonyl, C.sub.1 -C.sub.4 
alkoxysulfinyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl, C.sub.1 -C.sub.4 
alkanoyl, in particular formyl. 
Preferably, T is cyano, methylsulfonyl, ethylsulfonyl, chlorine, formyl or 
nitro and particularly preferably cyano, methylsulfonyl or formyl. 
The detachable substituent X is for example a halogen atom such as 
fluorine, chlorine or bromine, a C.sub.1 -C.sub.4 alkylsulfonyl group such 
as methylsulfonyl or ethylsulfonyl, a phenylsulfonyl radical, a sulfonic 
acid or phosphoric acid group or a quaternized ammonium group. 
Preferably, the detachable substituent X is fluorine or chlorine. 
In a group X of the aforementioned formula (2), arylene A is for example 
the bivalent radical of a benzene, or a naphthalene, of a biphenyl, of a 
stilbene, of a diphenylmethane or of a diphenyl ether. 
The arylene can be unsubstituted or substituted, for example by C.sub.1 
-C.sub.4 -alkyl, in particular methyl or ethyl, C.sub.1 -C.sub.4 alkoxy, 
in particular methoxy or ethoxy, halogen such as fluorine, chlorine or 
bromine, nitro, cyano, ureido, acetylamino, hydroxyl, carboxyl and/or 
sulfo. 
Preferably, A is an unsubstituted or for example, sulfo-, ureido-, methyl-, 
ethyl-, methoxy-, ethoxy-, chlorine-, hydroxyl- or carboxyl-substituted 
1,3-, or 1,4-phenylene radical. 
q, m and n are preferably independently of one another an integer from 2 to 
4, particularly preferably 2. 
An inorganic or organic radical Y which is detachable under alkaline 
conditions is for example one of the following detachable groups: 
##STR5## 
Preferably, Y is an --SSO.sub.3 H, --SSO.sub.3 H, --OPO.sub.3 H.sub.2, 
--Cl or --O--CO--C.sub.6 H.sub.5 group, and particularly preferably 
--OSO.sub.3 H. 
In a preferred embodiment of the reaction dyes of the formula (1) according 
to the invention, Z is a --CH.dbd.CH.sub.2 radical. 
A substituted C.sub.1 -C.sub.4 alkyl radical V can be for example have the 
meanings mentioned above for R and R'. 
A radical C of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z can differ 
from, or preferably conform to, the second --(CH.sub.2).sub.q --SO.sub.2 
--Z radical present in the group of the formula (2). 
V is preferably hydrogen, methyl, ethyl or a --(CH.sub.2).sub.q --SO.sub.2 
--Z group; V is particularly preferably hydrogen. 
Preferably, the radical X which is detachable as an anion is arranged in 
the 2-position and the group of the formula (2) or (3) in the 4-position 
in the pyrimidine radical. 
Preference is given in particular to reactive dyes of the formula (I) in 
which one X is a detachable substituent and the other X is a group of the 
formula 
##STR6## 
in which R"' and V' are independently of one another hydrogen or C.sub.1 
-C.sub.4 alkyl, R.sub.1 is hydrogen, sulfo, ureido, chlorine, methyl, 
ethyl, methoxy, ethoxy, hydroxyl or carboxyl, Z' is a --CH.dbd.CH.sub.2 or 
--CH.sub.2 --CH.sub.2 --Y' group, and Y' is --OSO.sub.3 H, --SSO.sub.3 H, 
--OCOOH.sub.3, --OPO.sub.3 H.sub.2, --Cl or --OCO--C.sub.6 H.sub.5. 
Consideration has also to be given to reactive dyes of the formula 
##STR7## 
in which Fa, T, R, R' and X are each as defined under the formula (1), R" 
independently has the meaning of N, E is a substituted or unsubstituted 
aliphatic or aromatic bridge member, and Q is a halogen atom, a 
substituted or unsubstituted amino group, hydroxyl, a C.sub.1 -C.sub.4 
alkoxy, phenyloxy, C.sub.1 -C.sub.4 alkylthio or phenylthio group. The 
bridge member E is preferably an alkylene or arylene radical. For 
instance, E can be a long (comprising for example 10 more more carbon 
atoms) or shorter, straight-chain or branched alkylene radical; in 
particular, an alkylene radical having 2 to 6 carbon atoms comes into 
consideration, for example ethylene, propylene, butylene, hexylene or 
cyclohexylene. An arylene radical E is for example a naphthalene radical, 
the radical of a biphenyl or stilbene or in particular a phenylene 
radical. The radical E can contain further substituents, for example 
halogen atoms, such as fluorine, chlorine and bromine, alkyl groups having 
1 to 4 carbon atoms, such as methyl, ethyl and propyl, alkoxy groups 
having 1 to 4 carbon atoms, such as methoxy, ethoxy, propyloxy and 
isopropyloxy, carboxyl or sulfo. 
The part of the formula (1) which is enclosed in square brackets is a 
reactive radical which can be present once or twice in the molecule; if r 
is 2, the two reactive radicals can be identical or different; preferably, 
the two radicals are identical. 
Particular preference is given to reactive dyes of the formula (1) in which 
r is 1. 
The compounds of the formula (1) are fibre-reactive. The term 
fibre-reactive compounds as used herein is to be understood as meaning 
those which are capable of reacting with the hydroxyl groups of cellulose, 
with the amino, carboxyl, hydroxyl and thiol groups in the case of wool 
and silk or with the amino and possibly carboxyl groups of synthetic 
polyamides to form covalent chemical bonds. 
A preferred group of reactive dyes according to the invention comprises 
compounds of the aforementioned formula (1) in which Fa is the radical of 
an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, 
phthalocyanine, formazan or dioxazine series which carries one or more 
sulfo groups and can be further substituted by one or more of the 
aforementioned radicals, R is hydrogen or an unsubstituted or for example 
halogen-, hydroxyl-, cyano-, carboxyl-, sulfo-, sulfato-, C.sub.1 -C.sub.4 
alkoxycarbonyl or C.sub.1 -C.sub.4 alkoxy- substituted C.sub.1 -C.sub.4 
alkyl radical, T is cyano, nitro, chlorine, formyl, methylsulfonyl or 
ethylsulfonyl, one X is chlorine or fluorine and the other X is a group of 
the formula 
##STR8## 
where R"' and V' are independently of one another hydrogen or C.sub.1 
-C.sub.4 -alkyl, Z' is a --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 -Y' 
group, Y' is --OSO.sub.3 H, --SSO.sub.3 H, --OCOOH.sub.3, --OPO.sub.3 
H.sub.2, --Cl or --OCO--C.sub.6 H.sub.5, R.sub.1 is hydrogen, sulfo, 
ureido, chlorine, methyl, ethyl, methoxy, ethoxy, hydroxyl or carboxyl, 
and r is 1. 
A particularly preferred embodiment of the present invention relates to 
reactive dyes of the formula 
##STR9## 
in which Fa is subject to the aforementioned definitions and preferences, 
T' is methylsulfonyl, formyl or cyano, X.sub.1 is fluorine or chlorine, 
R.sup.o and V" are independently of one another hydrogen, methyl or ethyl, 
Z" is a --CH.dbd.CH.sub.2, --CH.sub.2 --CH.sub.2 --OSO.sub.3 H, --CH.sub.2 
--CH.sub.2 --Cl or --CH.sub.2 --CH.sub.2 --OCOCH.sub.3 group, and R.sub.1 
is hydrogen, sulfo, ureido or carboxyl. 
A further group of usable reactive dyes according to the invention 
comprises compounds of the formula (1) in which Fa, R, T and n are subject 
to the aforementioned definitions and preferences and one X is chlorine or 
fluorine and the other X is a group of the formula 
##STR10## 
in which R"' and Z' are each defined as under the formula (2a). 
Preference is given here in particular to compounds of the formula 
##STR11## 
in which Fa, R.sup.o, R', X.sub.1 and Z" are each defined as under the 
formula (1b). 
Preferred subgroups of the reactive dyes of the formula (1) are: 
(a) monoazo or disazo dyes of the formula 
##STR12## 
in which R, T and X are each subject to the aforementioned definitions and 
preferences, D and D.sub.1 independently of one another are a diazo 
component of the benzene or naphthalene series, M is a central component 
of the benzene or naphthalene series, K is a coupling component of the 
benzene or naphthalene series or of the heterocyclic series, K.sub.1 is 
the radical of a coupling component of the aminonaphtholsulfonic acid 
series, and p is 0 or 1. 
Suitable subgroups of the reactive dyes of the formula (4) are compounds of 
the formula 
##STR13## 
in which R, T, X, K, D, M and p are each as defined above. 
Consideration must also be given to reactive dyes of the formulae (4), 
(4a), (4b) and (5) which the radical D, D.sub.1 and/or K additionally 
includes a further reactive radical, thus also encompassing tri- and 
tetra-reactive dyes. The additional reactive radicals included in D, 
D.sub.1 or K can be bonded to D, D.sub.1 or K via an amino group or in 
some other way, for example by way of a direct bond. 
Any additional reactive radical included in D, D.sub.1 or K is, or 
contains, in particular a low molecular weight alkanoyl or alkylsulfonyl 
radical which is substituted by a detachable atom or group; a low 
molecular weight alkenoyl or alkenesulfonyl radical which can be 
substituted by a detachable atom or group; a carbocyclic or heterocyclic 
radical which contains 4-, 5- or 6-rings and is bonded via a carbonyl or 
sulfonyl group and substituted by a detachable atom or group; or a 
triazine or pyrimidine radical which is bonded directly via a carbon atom 
and is substituted by a detachable atom or group. Examples of such 
reactive radicals are a six-membered heterocyclic radical which is bonded 
via an amino group and contains halogen atoms, such as a halotriazine or 
halopyrimidine radical, or an aliphatic acyl radical, such as a haloacetyl 
or halopropionyl radical. 
In particular, the additional reactive radical is a vinylsulfonyl, 
.beta.-sulfatoethylsulfonyl, .beta.-thiosulfatoethylsulfonyl, 
.beta.-chloroethylsulfonyl or .beta.-acetoxyethylsulfonyl radical bonded 
directly or via a bridge member. 
The above explanations apply mutatis mutandis also to metal complex azo 
dyes and to other chromophores mentioned in the definition of the dye 
radical D in formula (1). 
The radicals D and D.sub.2 can be derived for example from the following 
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, 
1-aminobiphenyl, 1-aminobenzene-2-, -3- or -4-carboxylic acid, 
2-aminodiphenyl ether, 1-aminobenzene-2-, -3- or -4-sulfonamide, 
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-4-methoxybenzene-2-sulfonic acid, 
1-amino-4-ethoxybenzene-2-sulfonic acid, 
1-amino-3-methylbenzene-6-sulfonic acid 1-amino-6-methylbenzene-3- or 
-4-sulfonic acid, 1-aminoaphthalene, 2-aminonaphthalene, 
1-aminophthalene-2-, -4-, -5-, -6-, -7- or -8-sulfonic acid, 
2-aminonaphthalene-1-, -3-, -4-, -5-, -6-, -7- or -8-sulfonic 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, 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-amino-4-.beta.-sulfatoethylsulfonylbenzene, 
1-amino-4-vinylsulfonylbenzene, 1-amino-3-vinylsulfonylbenzene, 
1-amino-4-.beta.-sulfatoethylsulfonylbenzene-2-sulfonic acid, 
1-amino-4-[.beta.(.beta.'-chloroethysulfonyl)ethylaminocarbonyl]-benzene-2 
-sulfonic acid, 
1-amino-4-.beta.-(vinylsulfonyl)ethylaminocarbonylbenzene-2-sulfonic acid, 
1-amino-3-.gamma.-(vinylsulfonyl)butyrylaminobenzene-6-sulfonic acid, 
1-amino-3-vinylsulfonyl-6-methoxybenzene, 
1-amino-3-.beta.-(vinylsulfonyl)ethylaminocarbonyl-6-methoxybenzene and 
1-amino-3- -(vinylsulfonyl)ethylaminocarbonylbenzene; and also 
diaminobenzenes or diaminonaphthalenes, such as 
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, 
1,4-diaminobenzene-2-carboxylic acid, 1,3-diaminobenzene-4-carboxylic 
acid, 1-amino-3-aminomethylbenzene-5-sulfonic acid, 
1-amino-3-aminomethyl-4-methoxybenzene-2-sulfonic acid, 
2,6-diaminonaphthalene-4,8-disulfonic acid, 
2-amino-5-aminomethylnaphthalene-1-sulfonic acid and 
2-amino-5-aminomethylnaphthalene-1,7-disulfonic acid; instead of a diamine 
it is also possible to use an aminoacetylamino compound from which the 
acetyl group is subsequently eliminated again, e.g. 
1-acetylamino-3-aminobenzene-4-sulfonic acid or 
1-acetylamino-4-aminobenzene-3-sulfonic acid. 
The radical M can be derived for example from the following central 
components: 
aniline, m-toluidine, 2,5-dimethyl- or -dimethoxy-aniline, m-aminoanisole, 
m-acetylamino-, m-propionylamino-, m-butyrylamino- or 
m-benzoylamino-aniline, m-aminophenylurea, 4-acetamino-2-amino-toluene or 
-anisole, 2-amino-4-methylanisole, 1-aminonaphthalene-6- or -7-sulfonic 
acid, 2-amino-4-acetylaminobenzenesulfonic acid, 
2-amino-5-naphthol-7-sulfonic acid, 2-amino-8-naphthol-6-sulfonic acid, 
2-(4-aminobenzoylamino)-5-naphthol-7-sulfonic acid, 
acetoacet-3-sulfo-4-aminoanilide. 
From the large number of possible coupling components K and K.sub.1 the 
following may be mentioned by way of example: 
phenol, 1-hydroxy-3- or -4-methylbenzene, 1-hydroxybenzene-4-sulfonic acid, 
1-hydroxynaphthalene, 2-hydroxynaphthalene, 2-hydroxynaphthalene-6- or 
-7-sulfonic acid, 2-hydroxynaphthalene-3,6- or -6,8-disulfonic acid, 
1-hydroxynaphthalene-4-sulfonic acid, 1-hydroxynaphthalene-4,6- or 
-4,7-disulfonic acid, 1-amino-3-methylbenzene, 
1-amino-2-methoxy-5-methylbenzene, 1-amino-2,5-dimethylbenzene, 
3-aminophenylurea, 1-amino-3-acetylaminobenzene, 
1-amino-3-hydroxyacetylaminobenzene, 1,3-diaminobenzene-4-sulfonic acid, 
1-aminoaphthalene-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-di-sulfonic 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-methyl-5-pyrazolone, 1-phenyl-3-methyl-5-pyrazoline, 
1-(4'-sulfophenyl)-3-methyl-5-pyrazolone, 
1-(4'-sulfophenyl)-5-pyrazolone-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'-disulfo-2'-naphthyl)-3-methyl-5-pyrazolone, 1-(5',7'-disulfo-2' 
-naphthyl)-3-methyl-5-pyrazolone, 
1-(2',5'-dichloro-4-sulophenyl)-3-methyl-5-pyrazolone, 
3-aminocarbonyl-4-methyl-6-hydroxy-2-pyridone, 1-ethyl-3-cyano- or 
-3-chloro-4-methyl-6-hydroxy-2-pyridone, 
1-ethyl-3-sulfomethyl-4-methyl-6-hydroxy-2-pyridone, 
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-hydroxy-2-pyridone, 
1-ethyl-3-sulfomethyl-4-methyl-5-carbamoyl-6-hydroxy-2-pyridone, 
N-acetoacetylaminobenzene, 
1-(N-acetoacetylamino)-2-methoxybenzene-5-sulfonic acid, 
4-hydroxy-2-quinolone, 
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-8-hydroxy-2-(2',5'-disulfophenylazo)-naphthalene-3,6-disulfonic 
acid, 1-.beta.-aminoethyl-3-cyano-4-methyl-6-hydroxy-2-pyridone, 
1-.gamma.-aminopropyl-3-sulfomethyl-4-methyl-6-hydroxy-2-pyridone, 
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, 
1-amino-3-N,N-disulfobenzylaminobenzene, 
N,N-di-(.beta.-sulfatoethyl)-aniline, 
3-acetylamino-N,N-di-(.beta.-sulfatoethyl)-aniline, 
3-methyl-N,N-di-(.beta.-sulfatoethyl)aniline, 
N-ethyl-N-(.beta.-hydroxyethyl)-aniline, 
N-ethyl-N-(.beta.-acetoxyethyl)-aniline, 
3-acetylamino-N,N-di(.beta.-hydroxyethyl)-aniline, 
3-methyl-N,N-di-(.beta.-acetoxyethyl)-aniline, 
2-methoxy-5-acetylamino-N-(.beta.-acetoxyethyl)-N-benzylaniline, 2 
-chloro-5-acetylamino-N-(.gamma.-phenoxy-.beta.-hydroxy-n-propyl)-aniline, 
3-ureidoaniline, N-ethyl-N-(3'-sulfobenzyl)-aniline, 
3-methyl-N-ethyl-N-(.beta.-sulfatoethyl)-aniline, 
3-methyl-N,N-di-(.beta.-hydroxyethyl)-aniline, 
3-methyl-6-methoxy-N,N-di-(.beta.-hydroxyethyl)-aniline. 
In reactive dyes of the formula (4) or (5) according to the invention , 
where Fa in formula (1) is accordingly the radical of a monoazo or disazo 
compound, this radical can be derived for example from the following 
organic monoazo or disazo dyes: 
##STR14## 
In the formulae shown above, R.sub.2, R.sub.3, R.sub.5 and R.sub.6 are 
independently of one another for example hydrogen, C.sub.1 -C.sub.4 alkyl, 
C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkanoylamino, ureido or 
halogen, and R.sub.4 is for example hydrogen or C.sub.1 -C.sub.4 alkyl. 
(b) Metal complexes of monoazo or disazo dyes of the aforementioned 
formulae (4) or (5) which have groups capable of metal complex formation, 
for example hydroxyl, carboxyl, amino or sulfo: 
where Fa in the formula (1) is the radical of a metal complex azo dye, this 
Fa can be derived for example from a metal complex of the following dyes: 
##STR15## 
where R.sub.4 is in each case as defined above. 
Preferred metal atoms are Cu (1:1 complex) or Cr and Co (1:2 complex). Cr- 
and Co-complexes can contain the azo compound of the abovementioned 
formula once or twice, i.e. they can have a symmetrical structure or 
incorporate any other desired ligands and have an asymmetrical structure. 
Examples of suitable copper complex dyes from which the radical Fa in the 
formula (1) can be derived are: 
##STR16## 
(c) anthraquinone dyes of the formula 
##STR17## 
in which R, T and X are each as defined above. 
(d) Formazan dyes of the formula 
##STR18## 
in which R, T and X are each as defined above. 
(e) Phthalocyanine dyes of the formula 
##STR19## 
in which R, T and X are each as defined above, Pc is the radical of a Cu- 
or Ni-phthalocyanine, R.sub.4, R.sub.7 and R.sub.8 are independently of 
one other C.sub.1 -C.sub.4 alkyl and in particular hydrogen and a and b 
are integral or fractional numbers from 1 to 3, a and b together being 
3.0. 
(f) Reactive dyes of the formula (1) in which Fa is for example a radical 
of a dioxazine dye of the formula 
##STR20## 
in which R is as defined above. 
A particularly preferred embodiment of the present invention relates to 
reactive dyes of the aforementioned formula (1b) in which Fa is a radical 
of the formula 
EQU [D--N.dbd.N--(M-N.dbd.N--).sub.p K-- (4') 
or 
EQU D--N.dbd.N--K.sub.1 --N.dbd.N--D.sub.1 -- (5') 
and 
D, D.sub.1, M, K, K.sub.1 and p are each as defined under the formula (4) 
or (5). 
Preference is given here in particular on the one hand to dyes of the 
formula (1b) in which Fa is a radical of the formula (4'), p is O, D is a 
radical of the formula 
##STR21## 
in which R.sub.9 is 1 to 3 identical or different radicals selected from 
the group consisting of sulfo, aminomethyl, .beta.-sulfatoethylsulfonyl 
and vinylsulfonyl, and K is the radical of 
1-amino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, of 
2-amino-5-hydroxynaphthalene-7-sulfonic acid or the radical of an 
unsubstituted or sulfo- or ureido-substituted aniline. 
Particular preference is further given to those dyes of the formula (1b) in 
which Fa is a radical of the formula (5'), D is the radical of a sulfo-, 
.beta.-sulfatoethylsulfonyl- and/or vinylsulfonyl-substituted 
aminobenzene, D.sub.1 is an unsubstituted or sulfo-substituted radical of 
a diaminobenzene and K.sub.1 is the radical of 1-amino-8-hydroxy-3,6- or 
-4,6-disulfonic acid. 
In a further group of particularly useful reactive dyes of the formula 
(1b), Fa is a radical of the formula 
##STR22## 
where Pc, R.sub.4, R.sub.7, R.sub.8, a and b are each as defined above 
under the formula (9). 
The reactive dyes according to the invention can be prepared for example by 
condensing organic dyes of the formula 
##STR23## 
or dye precursors with at least one equivalent of a pyrimidine of the 
formula 
##STR24## 
and at least one equivalent of an amine of the formula 
##STR25## 
or of the formula 
##STR26## 
in any desired order to give a reactive dye of the formula (1), Fa, R, R', 
T, A, V, Z, m, n, q and r each having as defined above and X' being 
defined in each case as a detachable substituent X, and, if dye precursors 
have been used, converting them into the desired final dyes. 
Optionally, the process according to the invention is followed by a further 
conversion reaction. Where the final dyes are prepared from precursors the 
further conversion reaction comprises in particular couplings which lead 
to azo dyes. Since the individual process steps mentioned above can be 
carried out in various orders, different process variants are possible. In 
general, the reaction is carried out in successive steps, the order of the 
elementary reactions between the individual reaction components 
advantageously depending on the particular conditions. Since under certain 
conditions a halopyrimidine radical will become hydrolyzed, it is 
necessary to hydrolyze an acetylamino-containing intermediate, to remove 
the acetyl groups, before condensation with a halopyrimidine. Which 
reaction is advanageously carried out first in the preparation of a 
secondary condensation product of an amine of the formula (2b) or (3b), of 
the pyrimidine of the formula (11) and the organic dye of the formula (10) 
or a precursor, that of the pyrimidine with the amine or that with the 
organic dye or with a precursor thereof, will vary from case to case and 
will depend in particular on the solubility of the amino compounds 
involved and on the basicity of the amino groups to be acylated. A 
possible further 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 (11) with a dye of the formula (10) or a dye precursor. For 
instance, a halogen atom can be replaced by another halogen atom through 
the action of a halogenating agent. The action of tertiary bases, such as 
trimethylamine, pyridine or 1,4-diazabicyclo[2.2.2]octane, gives 
corresponding ammonium compounds, and quaternization with hydrazines, such 
as N,N-dimethylhydrazine, gives corresponding hydrazinium compounds. By 
means of sulfites, for example sodium sulfite, and sulfinates it is 
possible to bring about a replacement of halogen by sulfo groups or a 
sulfonyl group, for example a 3'-carboxyphenylsulfonyl group and the like. 
By reaction with cyanides, for example potassium cyanide, and 
thiocyanates, for example potassium thiocyanate, it is possible to bring 
about a replacement of chlorine by a nitrile or thiocyanate group, which 
are likewise reactive. It is also possible to replace halogen atoms or 
other reactive groups through the action of sodium azide or compounds 
containing reactive methylene groups, for example cyanoacetic esters, 
malonic esters and acetylacetone, by the corresponding radicals. The 
replacement of a detachable substituent X' by another detachable 
substituent can in many cases also be carried out before the condensation 
of the pyrimidine of the formula (11) with a dye of the formula (10) or a 
dye precursor. 
Furthermore, the synthesis can be followed by elimination reactions. For 
example, reactive dyes of the formula (1) which contain 
sulfatoethylsulfonyl radicals can be treated with hydrogen halide 
eliminators, such as sodium hydroxide, to convert the sulfatoethylsulfonyl 
radicals into vinylsulfonyl radicals. 
A modified embodiment of the process comprises first preparing a dye which 
contains a preliminary stage of the reactive radical and subsequently 
converting this preliminary stage into the final stage, for example by 
esterification or an addition reaction. For example, a dye in which Z is 
an HO--CH.sub.2 CH.sub.2 -- radical can be prepared and be reacted, before 
or after the acylation, with sulfuric acid, so that the hydroxyl group is 
converted into a sulfato group; or an analogous dye is used in which Z is 
an H.sub.2 C.dbd.CH-- vinyl group, onto which thiosulfuric acid is added 
to form an HO.sub.3 SS--CH.sub.2 CH.sub.2 -- radical. The sulfation of the 
hydroxyl group in a dye of the formula (1) or a suitable precursor is 
effected for example by reaction with concentrated sulfuric acid at 
0.degree. C. to moderately elevated temperature. The sulfation can also be 
effected by reaction of the hydroxy compound with two equivalents of 
chlorosulfonic acid per hydroxyl group in a polar organic solvent, for 
example N-methylpyrrolidone, at 10.degree. to 80.degree. C. Preferably, 
the sulfation is effected by introducing the compound in question into 
sulfuric acid monohydrate at temperatures between 5.degree. and 15.degree. 
C. The introduction of another radical Y which is detachable under 
alkaline conditions in a compound of the formula (1) or an intermediate in 
place of the sulfato group, for example a thiosulfato group, is effected 
in a manner known per se. The preparation by way of an intermediate stage 
of the reactive radical proceeds in many cases uniformly and to 
completion. 
The process variant where the starting materials are dye precursors is 
suitable for preparing reactive dyes of the formula (1) in which Fa is the 
radical of a dye composed of two or more than two components. Examples of 
such dyes composed of two or more than two components are: monoazo, 
disazo, trisazo, metal complex azo, formazan and azomethine dyes. 
Generally, the reactive dyes of the formula (1) of all dye classes can be 
prepared in a manner known per se or analogously to known methods by 
starting from precursors of or intermediates for dyes which contain 
fibre-reactive radicals of formula (1) or by introducing these 
fibre-reactive radicals into intermediates of dye character which are 
suitable for this purpose. 
If the starting materials are dye precursors, if the reaction dyes of the 
formula (1) are obtained for example by condensing a component of the dye 
of formula (10) containing an --N(R)H group and a pyrimidine of the 
formula (11), condensing beforehand or afterwards with an amine of the 
formula (2b) or (3b), and reacting with the other component of the dye of 
the formula (10). In the preparation of the preferred azo dyes, the diazo 
components and the coupling components together need to contain at least 
one amino group --N(R)H and in addition the diazo components need to 
contain an amino group --NH.sub.2. 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 or nitro group is converted into the H.sub.2 N group, by 
hydrolysis and reduction respectively, before the condensation with the 
2,4,6-trihalopyrimidine. 
If groups capable of metal complex formation are present in the reactive 
dyes prepared, such as hydroxyl, carboxyl, amino or sulfo, the reactive 
dyes can subsequently also be metallized. For example, metal complex azo 
dyes are obtained by treating azo compounds which have been obtained 
according to the invention and which contain complexing groups, for 
example hydroxyl or carboxyl groups, in the ortho-ortho'-position relative 
to the azo bridge, with heavy metal donor agents before or if desired even 
after the condensation with the 2,4,6-trihalopyrimidine of the formula 
(10). Of particular interest are copper complexes of reactive dyes of the 
formula (1). In addition to the method of metallization mentioned above, 
other suitable methods are dealkylating metallization and, for the 
preparation of copper complexes, oxidative coppering. 
The most important process variants as illustrated in the working examples. 
The compounds of the formula (10) are known or can be prepared in a manner 
known per se. A selection of usable compounds of the formula (10) can be 
found in the discussion of the preferred subgroups of the reactive dyes 
according to the invention. 
Similarly, the pyrimidine compounds of the formula (11) are known for 
example from EP-A-141,776 or DE-A-2,310,334. 
Examples of suitable pyrimidine compounds of the formula (11) are: 
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-phenetylsulfonylpyrimidine, 
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, 
2,4,6-trichloro-5-cyanopyrimidine, 2,4,6-trichloro-5-formylpyrimidine. 
The compounds of the formula (2b) are known for exaple from EP-A-214,093 or 
can be prepared analogously thereto. Examples of suitable compounds of the 
formula (2b) are: 
3-amino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
4-chloro-3amino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
4-methyl-3-amino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
4-methoxy-3-amino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
3-amino-N'-.beta.-[.beta."-chloroethylsulfonyl)ethyloxy]ethyl-benzamide, 
3-amino-N'-.gamma.-(.beta.'-chloroethylsulfonyl)propyl-benzamide, 
3-amino-N'-bis[.beta.-(.beta.'-chloroethylsulfonyl)ethyl]-benzamide, 
3-amino-N'-bis[.gamma.-(.beta.'-chloroethylsulfonyl)propyl]-benzamide, 
3-N-ethylamino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
3-N-isopropylamino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
3-N-isopropylamino-N'-.gamma.-(.beta.'-chloroethylsulfonyl)propyl-benzamide 
4-amino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
4-amino-N'-.beta.-[.beta.'-(.beta."-chloroethylsulfonyl)ethyloxy]ethyl-benz 
amide, 
4-amino-N'-.gamma.-(.beta.'-chloroethylsulfonyl)propyl-benzamide, 
4-amino-N'-bis[.beta.-(.beta.'-chloroethylsulfonyl)ethyl]-benzamide, 
4-amino-N'-bis[.gamma.-.beta.'-chloroethylsulfonyl)propyl]-benzamide, 
4-N-ethylamino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
4-N-isopropylamino-N'-.gamma.-(.beta.'-chloroethylsulfonyl)propyl-benzamide 
4-amino-N'-.beta.-(vinylsulfonyl)ethyl-benzamide, 
4-amino-N'-bis[.beta.-(vinylsulfonyl)ethyl]-benzamide, 
4-amino-N'-.delta.-(.beta.'-chloroethylsulfonyl)butyl-benzamide, 
4-chloro-3-amino-N'-bis[.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide 
4-methyl-3-amino-N'-bis[.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide 
4-methoxy-3-amino-N'-bis[.gamma.-(.beta.'-chloroethylsulfonyl)propyl]-benza 
mide, 
3-amino-N'-.delta.-(.beta.'-chloroethylsulfonyl)butyl-benzamide, 
3-amino-N'-.beta.-[.beta.'-(.beta."-chloroethylsulfonyl)ethyloxy]ethyl-benz 
amide, 
4-hydroxy-3-amino-N'-.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamide, 
4-hydroxy-3-amino-N'-bis[.beta.-(.beta.'-chloroethylsulfonyl)ethyl]-benzami 
de, 
4-methoxy-3-amino-N'-bis[.beta.-(.beta.'-chloroethylsulfonyl)ethyl-benzamid 
e. 
The compounds of the formula (3b) are known for example from EP-A-144,766 
or can be prepared analogously thereto. 
The reactive dyes of the formula (1) according to the invention are 
suitable for dyeing and printing a very wide range of materials, such as 
silk, leather, wool, polyamide fibres, and in particular 
cellulose-containing fibre materials of any kind. Such fibre materials are 
for example the natural cellulose fibres, such as cotton, linen and hemp, 
and also cellulose pulp and regenerated cellulose. The reactive dyes 
according to the invention are also suitable for dyeing or printing 
hydroxyl-containing fibres which are present in blend fabrics, for example 
mixtures of cotton with polyester fibres or polaymide fibres. 
The dyes of the formula (1) 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 exhaustion 
method of dyeing but also for dyeing by the padding method, whereby the 
material is impregnated with aqueous, optionally salt-containing, dye 
solutions and the dyes are fixed after an alkali treatment or in the 
presence of alkali, optionally by heating. They are likewise suitable for 
the cold pad-batch process, whereby the dye is applied together with the 
alkali on a pad-mangle and is then fixed by storing for several hours at 
room temperature. After fixing, the dyeings or prints are thoroughly 
rinsed with cold and hot water, in the presence or absence of an agent 
which has a dispersing action and promotes the diffusion of the unfixed 
portions. 
The reactive dyes of the formula (1) are distinguished by high reactivity 
and good fixing properties and very good build-up. They can therefore be 
used for exhaustive dyeing at low dyeing temperatures and require only 
short steaming times in the pad-steam process. The degrees of fixation are 
high, and the unfixed portions can easily be washed off, the difference 
between the degree of exhaustion and the degree of fixation being 
remarkably small, i.e. the soaping loss being very small. The reactive 
dyes according to the invention are also suitable for printing, in 
particular on cotton, but also for printing on nitrogen-containing fibres, 
for example wool, silk or wool- or silk-containing blend fabrics. 
The dyeings and prints prepared with the dyes of the formula (1) according 
to the invention on cellulose fibre materials have a high tinctorial 
strength and high fibre-dye bond stability, not only in the acid but also 
in the alkaline range, and also a good light fastness and very good wet 
fastness properties, such as wash, water, seawater, cross-dyeing and 
perspiration fastness properties, and also a good pleating fastness, hot 
press fastness and rub fastness.

The Examples which follow serve to illustrate the invention. The 
temperatures are given in degrees Celsius, and parts and percentages are 
by weight, unless otherwise stated. Parts by weight relate to parts by 
volume as the kilogram relates to the liter. 
EXAMPLE 1 
A neutral solution of 25.3 parts of the amino azo dye of the formula 
##STR27## 
in 500 parts of water is admixed at room temperature with thorough 
stirring with 10.5 parts of 2,4,6-trichloro-5-methylsulfonylpyrimidine 
dissolved in 40 parts of acetone, and stirring is continued at that 
temperature for about 16 to 20 hours. The reaction solution is then 
brought to pH 7 with 1N sodium hydroxide solution and clarified by 
filtration. The dye of the formula 
##STR28## 
is then salted out and filtered off. The dye paste thus obtained is 
dissolved in 500 parts of water and gradually admixed with a solution of 
13.1 parts of the hydrochloride of 
1-amino-3-[.beta.-(.beta.'-chloroethylsulfonyl)ethylaminocarbonyl]benzene 
in 60 parts of water, the pH of the solution being maintained at about 7.0 
with 1N sodium hydroxide solution. 
The solution of the resulting dye of the formula 
##STR29## 
is then brought to pH 11 with 1N sodium hydroxide solution and 
subsequently maintained at room temperature for about 40 minutes, during 
which the dye is converted into the vinyl form. The pH is brought back to 
7 with hydrochloric acid, and the dye of the formula 
##STR30## 
is isolated with potassium chloride and dried in vacuo. 
The dye obtained, on application to cotton by the dyeing methods customary 
for vinyl sulfone dyes, produces bluish red dyeings having good all-round 
fastness properties: .lambda..sub.max =530 nm. 
EXAMPLES 2-13 
Example 1 is repeated, except that the dye of the formula (12) is replaced 
by the dyes mentioned in Table 1, affording analogous dyes which dye 
cotton in the hues given in the table. 
TABLE 1 
__________________________________________________________________________ 
Example .lambda..sub.max 
Hue on 
No. Dye [nm] 
cotton 
__________________________________________________________________________ 
##STR31## 381 yellow 
3 
##STR32## 408 yellow 
4 
##STR33## 420 yellow 
5 
##STR34## 430 yellow 
6 
##STR35## 488 orange 
7 
##STR36## 548 red 
8 
##STR37## 596 navy 
9 
##STR38## 610 navy 
10 
##STR39## 610 navy 
11 
##STR40## 608 blue 
12 
##STR41## 596 blue 
13 
##STR42## 558 blue 
14 
##STR43## 586 blue 
15 
##STR44## 524 red 
16 
##STR45## 608 navy 
17 
##STR46## 608 navy 
__________________________________________________________________________ 
EXAMPLE 18 
16.4 parts of the dye of the formula 
##STR47## 
are dissolved in 300 parts of water, and the solution is cooled down to 
0.degree.-5.degree. C. At that temperature, a solution of 6.4 parts of 
2,4,6-trifluoro-5-methylsulfonylpyrimidine in 50 parts of acetone is added 
with thorough stirring while the pH is maintained at about 7.0 by dropwise 
addition of 1N sodium hydroxide solution. 
After the reaction has ended, the reaction solution is admixed with a 
solution of 9.8 parts of the hydrochloride of 
1-amino-3-[.beta.-(.beta.'-chlorosulfonyl)ethylaminocarbonyl]benzene, the 
pH of the solution being maintained at about 7.0 with 1N sodium hydroxide 
solution. 
The aqueous solution of the dye obtained is then vinylated at room 
temperature and pH 11 for about 40 minutes. The pH is then brought back to 
7.0 with hydrochloric acid, and the dye of the formula 
##STR48## 
is salted out with potassium chloride, filtered off and dried in vacuo. 
The dye obtained, on application to cotton by methods customary for vinyl 
sulfone dyes, produces golden yellow dyeings having good all-round 
fastness properties. .lambda..sub.max =422 nm. 
EXAMPLE 19 
Example 18 is repeated, except that the dye of the formula (13) is replaced 
by 16.6 parts of the dye of the formula 
##STR49## 
affording the dye of the formula 
##STR50## 
which dyes cotton in an orange shade having good fastness properties. 
.lambda..sub.max =488 nm. 
EXAMPLE 20 
A neutral solution of 28.1 parts of a disazo dye of the formula 
##STR51## 
in 600 parts of water is admixed at room temperature with thorough 
stirring with a solution of 8.4 parts of 2,4,6-trichloro-5-cyanopyrimidine 
in 40 parts of acetone, and stirring is continued at that temperature for 
about 16-20 hours. The pH of the solution is then brought back to 7.0 with 
1N sodium hydroxide solution, and the solution is clarified by filtration. 
To the dye solution is then added dropwise a solution of 13.1 parts of the 
hydrochloride of 
1-amino-3-[.beta.-(.beta.'-chloroethylsulfonyl)ethylaminocarbonyl]benzene 
in 50 parts of water, the pH of the reaction mixture being maintained at 
about 7.0 with 1N sodium hydroxide solution. 
The aqueous solution of the dye obtained is vinylated at room temperature 
and pH 11 for about 40 minutes. The pH is then brought back to 7.0 with 
hydrochloric acid, the dye of the formula 
##STR52## 
is precipitated by addition of potassium chloride, filtered off and dried 
in vacuo. The dye thus obtained dyes cotton in a navy shade having good 
allround fastness properties. .lambda..sub.max =596 nm. 
EXAMPLE 21 
13.6 parts of the aminoazo dye of the formula 
##STR53## 
are dissolved in 150 ml of water under neutral conditions and is acylated 
at pH 6-6.5 and at a temperature of 0.degree.-5.degree. C. with a solution 
of 6 g of 2,4,6-trichloro-5-formylpyrimidine in 25 ml of acetone; in the 
course of the acylation the pH is maintained at 6-6.5 by dropwise addition 
of 2N sodium hydroxide solution. The dye solution is then clarified by 
filtration and reacted at pH 5.0-5.5 and at a temperature of 25.degree. C. 
with a solution of 8.6 parts of the hydrochloride of 
1-amino-3-[.beta.-(.beta.'-chloroethylsulfonyl)ethylaminocarbonyl]benzene 
in 150 ml of water. The pH is then adjusted to 10 with 2N sodium hydroxide 
solution, and vinylation is effected for 20 minutes. The dye is salted out 
with potassium chloride, filtered off and dried at 30.degree. C. in vacuo. 
The dye thus obtained has the formula 
##STR54## 
and dyes cotton in golden yellow shades (.lambda..sub.max 424 nm). 
EXAMPLES 22-38 
Example 21 is repeated, except that the aminoazo dye used therein is 
replaced by the dyes mentioned in Table 2, affording analogous dyes which 
dye cotton in the hues given in the table. 
TABLE 2 
__________________________________________________________________________ 
Example .lambda..sub.max 
Hue on 
No. Dye [nm] cotton 
__________________________________________________________________________ 
22 
##STR55## 528 bluish red 
23 
##STR56## 381 yellow 
24 
##STR57## 408 yellow 
25 
##STR58## 430 yellow 
26 
##STR59## 488 orange 
27 
##STR60## 548 red 
28 
##STR61## 596 navy 
29 
##STR62## 610 navy 
30 
##STR63## 597 navy 
31 
##STR64## 608 blue 
32 
##STR65## 596 blue 
33 
##STR66## 588 blue 
(only one amino group is made to react) 
34 
##STR67## 586 blue 
35 
##STR68## 524 red 
36 
##STR69## 604 navy 
37 
##STR70## 610 navy 
__________________________________________________________________________ 
EXAMPLE 38 
Example 21 is repeated, except that 
1-amino-3-[.beta.-(.beta.'-chloroethylsulfonyl)ethylaminocarbonyl]benzene 
is replaced by the equivalent amount of 
1-amino-4-[.beta.-(.beta.'-chloroethylsulfonyl)ethylaminocarbonyl]benzene, 
affording the dye of the formula 
##STR71## 
which likewise dyes cotton in golden yellow shades (.lambda..sub.max 420 
nm). 
DYEING METHOD I 
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 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 5 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 6 are dissolved in 400 
parts of water; to this solution are added 1,400 parts of a solutiou 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 7 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 9 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 onto 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 14 are dissolved in 100 
parts of water with the addition of 0.5 part of sodium 
n-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 12 are sprinkled with 
high-speed stirring into 100 parts of 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 7 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 m-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, 
optionally soaped off at the boil and rinsed once more, and is then dried.