Compounds of the formula ##STR1## salts thereof, and mixtures of such compounds and salts, wherein D.sub.1 is ##STR2## wherein R.sub.1 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --SO.sub.3 H or --COOH, PA2 R.sub.2 is --COOH, --CONR.sub.6 R.sub.7, --SO.sub.2 NR.sub.6 R.sub.7 or --SO.sub.2 --X, wherein each of R.sub.6 and R.sub.7 is independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 -hydroxyalkyl or C.sub.2-4 sulfatoalkyl, or PA3 --NR.sub.6 R.sub.7 is a saturated 5- or 6-membered heterocyclic ring containing no hetero atom in addition to the nitrogen atom to which R.sub.6 and R.sub.7 are attached or containing one hetero atom selected from nitrogen and oxygen in addition to said nitrogen atom, which ring is unsubstituted or substituted by 1 to 3 C.sub.1-4 alkyl groups, and PA2 m is 0, 1 or 2, and PA1 D.sub.2 is ##STR3## wherein R.sub.3 is hydrogen, --SO.sub.3 H or --COOH, PA2 R.sub.4 is hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, halo, cyano, --SO.sub.3 H, --OSO.sub.3 H or --COOH, PA2 n is 0 or 1, and PA2 p is 1 or 2, wherein PA1 X is --CH.dbd.CH.sub.2 or --W--Y, wherein PA1 W is linear or branched C.sub.2-4 alkylene, and PA1 Y is hydroxy or a group which can be split off under alkaline conditions, with the provisos that (i) R.sub.1 may be --COOH only when R.sub.2 is --SO.sub.2 --X, (ii) D.sub.2 must be a group of Formula (d) when D.sub.1 is a group of Formula (a) wherein R.sub.1 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --SO.sub.3 H, and R.sub.2 is --COOH, --CONR.sub.6 R.sub.7 or --SO.sub.2 NR.sub.6 R.sub.7 or a group of Formula (b), and (iii) D.sub.2 must be a group of Formula (e) when D.sub.1 is a group of Formula (a) wherein R.sub.1 is --COOH, and R.sub.2 is --SO.sub.2 --X, useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, for example leather and fiber material comprising natural or synthetic polyamides or natural or regenerated cellulose, especially textile material comprising cotton. The obtained dyeings and printings show good general fastness properties such as good light fastness, wet fastnesses and resistance towards oxidative influences.

This invention relates to fibre-reactive disazo compounds and a process for 
their preparation. These compounds are suitable for use as fibre-reactive 
dyestuffs in any conventional dyeing or printing processes. 
More particularly, the invention provides compounds of formula I 
##STR4## 
and salts thereof, in which 
D.sub.1 is 
##STR5## 
and D.sub.2 is 
##STR6## 
or D.sub.1 is 
##STR7## 
and D.sub.2 is 
##STR8## 
in which R.sub.1 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy 
or --SO.sub.3 H, 
R.sub.2 is --COOH, --CONR.sub.6 R.sub.7, --SO.sub.2 NR.sub.6 R.sub.7 or 
--SO.sub.2 --X, 
wherein each of R.sub.6 and R.sub.7 is independently hydrogen, C.sub.1-4 
alkyl, C.sub.2-4 hydroxyalkyl or C.sub.2-4 sulphatoalkyl, or 
--NR.sub.6 R.sub.7 is a saturated 5- or 6-membered heterocyclic ring which 
may contain one further hetero atom N or O and which is further 
unsubstituted or substituted by 1 to 3 C.sub.1-4 alkyl groups, and 
X is --CH.dbd.CH.sub.2 or --C.sub.2-4 alkylene--Y, 
wherein Y is hydroxy or a radical which can be split off under alkaline 
conditions, e.g., --OSO.sub.3 H, Cl, Br, --OPO.sub.3 H.sub.2, --SSO.sub.3 
H, --OCOCH.sub.3, --OCOC.sub.6 H.sub.5 or --OSO.sub.2 CH.sub.3 ; 
R.sub.3 is hydrogen, --SO.sub.3 H or --COOH, 
R.sub.4 is hydrogen, unsubstituted C.sub.1-4 alkyl or C;.sub.1-4 alkyl 
monosubstituted by hydroxy, halogen, cyano, --SO.sub.3 H, --OSO.sub.3 H or 
--COOH, 
R.sub.5 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --SO.sub.3 
H or --COOH, 
m is 0, 1 or 2, 
n is 0 or 1, 
p is 1 or 2, and 
Z is 
##STR9## 
and mixtures of compounds of formula I. 
In the specification, any alkyl or alkylene group present is linear or 
branched unless indicated otherwise. 
In any hydroxy- or sulphato-substituted alkyl or alkylene group which is 
attached to a nitrogen atom, the hydroxy or sulphato group is preferably 
bound to a carbon atom which is not directly attached to this nitrogen 
atom. 
Any halogen is preferably fluorine, chlorine or bromine; more preferably, 
it is chlorine or bromine and especially chlorine. 
R.sub.1 is preferably R.sub.1a, where R.sub.1a is hydrogen, chlorine, 
methyl, methoxy or sulpho; more preferably, R.sub.1 is R.sub.1b, where 
R.sub.1b is hydrogen or sulpho. Most preferably R.sub.1 is hydrogen. 
R.sub.6 is preferably R.sub.6a, where R.sub.6a is hydrogen, methyl, ethyl, 
C.sub.2-4 hydroxyalkyl or C.sub.2-4 sulphatoalkyl; and R.sub.7 is 
preferably R.sub.7a, where R.sub.7a is hydrogen, C.sub.2-4 hydroxyalkyl or 
C.sub.2-4 sulphatoalkyl; or --NR.sub.6a R.sub.7a is a piperidine, 
piperazine, N-methylpiperazine or morpholine ring. 
More preferably, R.sub.6 is R.sub.6b, where R.sub.6b is hydrogen, methyl, 
ethyl, 2-hydroxyethyl or 2-sulphatoethyl; and R.sub.7 is R.sub.7b, where 
R.sub.7b is hydrogen, 2-hydroxyethyl or 2-sulphatoethyl; or --NR.sub.6b 
R.sub.7b is a morpholine ring. 
Most preferably, R.sub.6 is R.sub.6c, where R.sub.6c is hydrogen, 
2-hydroxyethyl or 2-sulphatoethyl; and R.sub.7 is R.sub.7c, where y.sub.7c 
is hydrogen or 2-hydroxyethyl; or --NR.sub.6c R.sub.7c is a morpholine 
ring. 
X is preferably X.sub.a, where X.sub.a is --CH.dbd.CH.sub.2, --C.sub.2-3 
alkylene--OH or --C.sub.2-3 alkylene--OSO.sub.3 H; more preferably, X is 
X.sub.b, where X.sub.b is --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.2 OH or 
--CH.sub.2 CH.sub.2 OSO.sub.3 H; most preferably it is X.sub.c, where 
X.sub.c is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 OSO.sub.3 H, 
especially --CH.sub.2 CH.sub.2 OSO.sub.3 H. 
R.sub.2 is preferably R.sub.2a, where R.sub.2a is --COOH, --SO.sub.2 
NR.sub.6a R.sub.7a or --SO.sub.2 --X.sub.a ; more preferably it is 
R.sub.2b, where R.sub.2b is --COOH, --SO.sub.2 NR.sub.6b R.sub.7b or 
--SO.sub.2 --X.sub.b. Even more preferably R.sub.2 is R.sub.2c, where 
R.sub.2c is --SO.sub.2 NR.sub.6c R.sub.7c or --SO.sub.2 --X.sub.c. Most 
preferably R.sub.2 is --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H. 
A radical (a) is preferably of formula (a.sub.1) 
##STR10## 
more preferably of formula (a.sub.2), 
##STR11## 
in which R.sub.2b is in the 4- or 5-position; most preferably of formula 
(a.sub.3), 
##STR12## 
in which R.sub.2c is especially --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H. 
m is preferably 0 or 1. 
A radical (b) is preferably (b.sub.1), where (b.sub.1) is one of the 
radicals of the formulae 
##STR13## 
more preferably it is (b.sub.2), where (b.sub.2) is one of the radicals of 
the formulae (b.sub.11), (b.sub.12) and (b.sub.13). 
R.sub.3 is preferably R.sub.3a, where R.sub.3a is --COOH or --SO.sub.3 H. 
Most preferably R.sub.3 is --SO.sub.3 H. 
R.sub.4 is preferably R.sub.4a, where R.sub.4a is hydrogen, methyl, ethyl, 
2-hydroxyethyl, --(CH.sub.2).sub.q --SO.sub.3 H, --(CH.sub.2).sub.q --COOH 
or --(CH.sub.2).sub.q --OSO.sub.3 H, in which q is 1, 2 or 3. 
More preferably R.sub.4 is R.sub.4b, where R.sub.4b is hydrogen or methyl. 
Most preferably R.sub.4 is hydrogen. 
A radical (d) is preferably of formula (d.sub.1) 
##STR14## 
more preferably of formula (d.sub.2), 
##STR15## 
in which --NR.sub.4b --Z is in the 4- or 5-position; most preferably of 
formula (d.sub.3) 
##STR16## 
R.sub.5 is preferably R.sub.5a, where R.sub.5a is hydrogen, chlorine, 
methyl, methoxy or sulpho. More preferably R.sub.5 is R.sub.5b, where 
R.sub.5b is hydrogen or sulpho. Most preferably R.sub.5 is hydrogen. 
A radical (c) is preferably of formula (c.sub.1), 
##STR17## 
in which --SO.sub.2 --X.sub.a is preferably in the 4- or 5-position; more 
preferably it is of formula (c.sub.2), 
##STR18## 
in which --SO.sub.2 --X.sub.b is in the 4- or 5-position; most preferably 
it is of formula (c.sub.3), 
##STR19## 
in which --SO.sub.2 --X.sub.c is in the 3- or 4-position. 
A radical (e) is preferably of formula (e.sub.1), 
##STR20## 
in which t is 0 or 1; more preferably of formula (e.sub.2), 
##STR21## 
in which R.sub.4b is most preferably hydrogen. 
Furthermore, in the 1-amino-8-hydroxynaphthalene radical of compounds of 
formula I the floating sulpho substituent is preferably in the 3-position. 
Preferred compounds of formula I correspond to formula Ia 
##STR22## 
and salts thereof, in which 
D.sub.1 ' is a radical (a.sub.1) or (b.sub.1) and 
D.sub.2 ' is a radical (d.sub.1); or 
D.sub.1 ' is a radical (c.sub.1) and 
D.sub.2 ' is a radical (e.sub.1), as defined above. 
More preferred are compounds of formula Ia in which D.sub.1 ' is D.sub.1 " 
and D.sub.2 ' is D.sub.2 ", where D.sub.1 " is a radical (a.sub.2) or 
(b.sub.2) and D.sub.2 " is a radical (d.sub.2); or D.sub.1 " is a radical 
(c.sub.3) and D.sub.2 " is a radical (e.sub.2), as defined above. 
Most preferred are compounds of formula Ia in which D.sub.1 ' is D.sub.1 "' 
and D.sub.2 ' is D.sub.2 "', where D.sub.1 "' is a radical (a.sub.3) and 
D.sub.2 "' is a radical (d.sub.3), as defined above. 
Further preferred compounds of formula I are those of formula Ib 
##STR23## 
and salts thereof, wherein 
R.sub.2x is --COOH, --SO.sub.2 --C.sub.2-4 alkylene--OH, --SO.sub.2 
--C.sub.2-4 alkylene--OSO.sub.3 H, --CONR.sub.6 R.sub.7 or --SO.sub.2 
NR.sub.6 R.sub.7 
R.sub.3x is --COOH or --SO.sub.3 H, and 
R.sub.4x is hydrogen or C.sub.1-4 alkyl, 
wherein R.sub.6, R.sub.7 and Z are as defined above. 
When a compound of formula I is in salt form, the cations associated with 
the sulpho groups and any carboxy group are not critical and may be any of 
those non-chromophoric cations conventional in the field of fibre-reactive 
dyes provided that the corresponding salts are water-soluble. Examples of 
such cations are alkali metal cations and unsubstituted and substituted 
ammonium cations, e.g., lithium, sodium, potassium, ammonium, mono-, di-, 
tri- and tetra-methylammonium, triethylammonium and mono-, di- and 
tri-ethanolammonium. 
The preferred cations are the alkali metal cations and ammonium, with 
sodium being the most preferred. 
In a compound of formula I the cations of the sulpho and any carboxy groups 
can be the same or different, e.g., they can also be a mixture of the 
above mentioned cations meaning that the compound of formula I can be in a 
mixed salt form. 
The invention further provides a process for the preparation of compounds 
of formula I, and mixtures thereof, by the reaction under neutral to 
weakly basic conditions of a diazonium salt of an amine of formula II 
EQU D.sub.2 --NH.sub.2 II 
or a mixture of such amines, wherein D.sub.2 is as hereinabove defined, 
with a compound of formula III 
##STR24## 
or a mixture of such compounds, wherein D.sub.1 is as hereinabove defined. 
The compounds of formula I may be isolated in accordance with known 
methods, for example, by conventional salting out with alkali metal salt, 
filtering and drying, optionally in vacuo and at slightly elevated 
temperatures. 
Depending on the reaction and isolation conditions a compound of formula I 
is obtained in free acid or preferably salt form or even mixed salt form 
containing, for example, one or more of the above mentioned cations. It 
may be converted from free acid form to a salt form or mixture of salt 
forms or vice versa or from one salt form to another by conventional 
means. 
The starting compounds of formulae II and III are either known or may be 
readily made from known materials using known methods. 
Amines according to formula II may be obtained by the condensation reaction 
of compounds of formula IV or formula V 
##STR25## 
wherein R.sub.3, R.sub.4, n and p are as hereinabove defined, with 
5-cyano-2,4,6-trichloropyrimidine, this reaction being carried out at a 
temperature of 0.degree.-40.degree. C. (preferably 0.degree.-20.degree. 
C.) and at a pH of from 6-9. 
Compounds of formula III may be prepared by the reaction under acidic 
conditions of the diazonium salt of amines according to one of the 
formulae VI, VII and VIII, 
##STR26## 
in which R.sub.1, R.sub.2, R.sub.5, X and m are as hereinabove defined, 
with 1-amino-8-hydroxynaphthalene-3,6- or -4,6-disulphonic acid. 
The compounds of formula I and mixtures thereof are useful as 
fibre-reactive dyestuffs for dyeing or printing hydroxy group- or 
nitrogen-containing organic substrates. Preferred substrates are leather 
and fibre material comprising natural or synthetic polyamides and, 
particularly, natural or regenerated cellulose such as cotton, viscose and 
spun rayon. The most preferred substrate is textile material comprising 
cotton. 
Dyeing or printing is effected in accordance with known methods 
conventional in the fibre-reactive dyestuff field. Preferably, for the 
compounds of formula I the exhaust dyeing method is used at temperatures 
within the range of 30.degree. to 60.degree. C. 
The compounds of this invention have good compatibility with known 
fibre-reactive dyes; they may be applied alone or in combination with 
appropriate fibre-reactive dyestuffs of the same class having analogous 
dyeing properties such as common fastness properties and the extent of 
ability to exhaust from the dyebath onto the fibre. The dyeings obtained 
with such combination mixtures have good fastness properties and are 
comparable to those obtained with a single dyestuff. 
The compounds of formula I give good exhaust and fixation yields when used 
as dyestuffs. Moreover, any unfixed compound is easily washed off the 
substrate. The dyeings and prints derived from the compounds of formula I 
exhibit good dry and wet light fastness and good wet fastness properties 
such as wash, water, sea water and sweat fastness. They also exhibit good 
resistance to oxidation agents such as chlorinated water, hypochlorite 
bleach, peroxide bleach and perborate-containing washing detergents. 
Furthermore, the dyeings and prints obtained with the compounds of formula 
I show notably high stability to acid hydrolysis, for example, a dyeing 
contacted with dilute acetic acid shows only slight staining of the undyed 
accompanying fabric. 
The invention is further illustrated with reference to the following 
non-limiting examples, in which all parts are expressed by weight unless 
otherwise stated and all temperatures are in degrees Centigrade.

EXAMPLE 1 
29.5 Parts of 4-aminophenyl-(2'-sulphatoethyl)sulphone are suspended in 
43.0 parts of concentrated hydrochloric acid and stirred for an hour. 125 
Parts of ice are added, followed by 26.2 parts of a 4N sodium nitrite 
solution, this being added dropwise under the surface of the mixture. The 
mixture is stirred for two hours during which time the temperature is 
maintained at 0.degree.-5.degree.. Excessive nitrite is destroyed by the 
addition of sulphamic acid. 
31.9 Parts of 1-amino-8-hydroxynaphthalene-3,6-disulphonic acid are added 
to 150 parts of water and the solution is made neutral by the addition of 
10.5 parts of concentrated sodium hydroxide solution. This solution is 
added dropwise to the cooled solution described in the previous paragraph. 
The mixture is then stirred for 3 hours and the temperature held at 
5.degree.-10.degree. during this time. After this, the mixture is 
neutralised by the addition of 35 parts of concentrated sodium hydroxide 
solution, and filtered, and the residue is washed with 400 parts of water. 
The filtrate is blended with the wash liquid, and a solid is salted out 
with common salt and filtered off. The resultant red filter cake is 
retained for later use. 
21.8 Parts of 2-cyano-2,4,6-trichloropyrimidine are dispersed in a mixture 
of 140 parts of ice and 35 parts of water and stirred for 45 minutes at 
0.degree.-2.degree.. 
8.8 Parts of 2,4-diaminobenzenesulphonic acid are dispersed in 140 parts of 
water and neutralised with 9.5 parts of sodium hydroxide. The resulting 
solution is added dropwise over the period of an hour to the 
5-cyano-2,4,6-trichloropyrimidine dispersion previously described, the 
temperature being maintained at 0.degree.-2.degree.. The suspension thus 
obtained is brought to pH 4 by the addition of sodium carbonate solution 
and is then blended with 26.2 parts of a 4N sodium nitrite solution. This 
blend is added to a mixture consisting of 150 parts of ice, 20 parts of 
water and 44 parts of concentrated hydrochloric acid to give a diazonium 
salt solution. 
The red filter cake whose preparation is described hereinabove is dispersed 
in 300 parts of water, 2 parts of a 20% by weight solution of sodium 
carbonate are added and the dispersion is cooled to 5.degree.. The pH of 
the abovementioned diazonium salt solution is brought to 7.5-8, and it is 
added dropwise to the red filter cake dispersion. The resulting dyestuff 
is salted out, filtered off and dried under vacuum. It has the formula 
##STR27## 
and dyes cotton in deep navy blue tones. These dyeings exhibit good 
properties such as light- and wet-fastnesses and are stable in the 
presence of oxidising agents. 
EXAMPLES 2-54 
Further analogous compounds may be made by the methods described in Example 
1. These compounds correspond to one of the following formulae 
##STR28## 
and the nature of the substituents for each compound is given in Tables 1 
[compounds corresponding to formula (A)], 2 [compounds corresponding to 
formula (B)] and 3 (compounds corresponding to formula (C)]. In these 
Tables, the entity Z is 
##STR29## 
and X is X.sub.1, X.sub.2 or X.sub.3 where 
X.sub.1 is --CH.sub.2 CH.sub.2 OSO.sub.3 H, 
X.sub.2 is --CH.sub.2 CH.sub.2 OH, and 
X.sub.3 is --CH.dbd.CH.sub.2. 
The compounds of Examples 2-54 may be applied to substrates which comprise 
cellulose fibres, particularly for dyeing in navy blue tones textile 
materials comprising cotton using conventional exhaust dyeing or printing 
processes. The dyeings and printings obtained thereby on cotton exhibit 
good light- and wet-fastness properties and they are resistant to 
oxidising agents. 
TABLE 1 
__________________________________________________________________________ 
Example Position of 
Position of 
No. R.sub.1 
R.sub.2 R.sub.2 
SO.sub.3 H 
R.sub.3 
__________________________________________________________________________ 
2 H SO.sub.2 X.sub.1 
3 3 SO.sub.3 H 
3 H " 4 4 " 
4 H " 4 3 COOH 
5 H " 3 3 " 
6 H SO.sub.2 X.sub.2 
4 3 SO.sub.3 H 
7 H " 3 3 " 
8 H " 4 3 COOH 
9 SO.sub.3 H 
SO.sub.2 X.sub.3 
4 3 " 
10 " " 4 4 " 
11 H SO.sub.2 NH.sub.2 
4 3 SO.sub.3 H 
12 H " 3 3 " 
13 H SO.sub.2 NHCH.sub.2 CH.sub.2 OH 
4 3 " 
14 H " 3 4 " 
15 H " 4 3 COOH 
16 H " 3 3 " 
17 H SO.sub.2 NHCH.sub.2 CH.sub.2 OSO.sub.3 H 
4 3 SO.sub.3 H 
18 H " 3 3 COOH 
19 H SO.sub.2 N(CH.sub.2 CH.sub.2 OH).sub.2 
4 3 " 
20 H " 4 3 SO.sub.3 H 
21 H 
##STR30## 4 3 " 
22 H " 3 3 " 
23 H " 4 4 " 
24 H COOH 4 3 COOH 
25 H " 3 3 " 
26 H " 4 3 SO.sub.3 H 
27 H " 3 3 " 
28 SO.sub.3 H 
SO.sub.2 X.sub.1 
4 3 " 
29 H " 3 4 " 
30 SO.sub.3 H 
SO.sub.2 X.sub.2 
4 3 " 
31 SO.sub.3 H 
SO.sub.2 X.sub.1 
3 4 H 
32 H 
##STR31## 4 3 SO.sub.3 H 
33 SO.sub.3 H 
SO.sub.2 X.sub.3 
4 3 " 
34 " " 5 3 " 
__________________________________________________________________________ 
TABLE 2 
__________________________________________________________________________ 
Example 
Position of 
Position of 
Position of Position of 
No. --SO.sub.2 --X.sub.1 
m (SO.sub.3 H).sub.m 
SO.sub.3 H 
R.sub.3 
R.sub.4 
--NR.sub.4 --Z 
__________________________________________________________________________ 
35 8 1 6 3 --SO.sub.3 H 
H 5 
36 8 1 6 3 " H 4 
37 8 1 6 4 " --CH.sub.3 
5 
38 8 1 6 3 --COOH 
H 5 
39 8 1 6 4 " H 4 
40 6 1 1 3 " H 5 
41 6 1 1 3 " --CH.sub.3 
5 
42 6 1 1 3 --SO.sub.3 H 
H 5 
43 6 1 1 4 " H 5 
44 8 0 -- 3 " H 5 
45 8 0 -- 4 " H 5 
46 8 0 -- 4 " --CH.sub.3 
4 
47 8 0 -- 3 " H 4 
__________________________________________________________________________ 
##STR32## 
By the preparation method described in Example 1 the compounds of Examples 
1-54 are obtained in sodium salt form. By changing the reaction or 
isolation conditions or by using other known methods, it is possible to 
produce the compounds in free acid form or in other salt forms or mixed 
salt forms which contain one or more of the cations mentioned hereinabove. 
It should be noted that the group Z 
##STR33## 
can occur in two isomeric forms, with the floating chlorine substituent in 
either the 2- or the 6-position. The naturally-occuring ratio of 
2-position to 6-position is about 2:1. In general, it is preferred to use 
this mixture as is without resorting to the isolation of a single isomer, 
but should this be desired it can be readily achieved by conventional 
methods. 
In the following examples, the application of compounds of this invention 
is illustrated. 
Application Example A 
0.3 Part of the dyestuff of Example 1 is dissolved in 300 parts of 
demineralised water and 15 parts of Glauber's salt (calcined) are added. 
The dyebath is heated to 40.degree., then 10 parts of cotton fabric 
(bleached) are added. After 30 minutes at 40.degree., 6 parts of sodium 
carbonate (calcined) are added to the bath portionwise every 10 minutes 
applying quantities of 0.2, 0.6, 1.2 and finally 4.0 parts thereof. During 
the addition of sodium carbonate the temperature is kept at 40.degree.. 
Subsequently, dyeing is effected for a further one hour at 40.degree.. 
The dyed fabric is then rinsed with running cold water for 3 minutes and 
afterwards with running hot water for a further 3 minutes. The dyeing is 
washed at the boil for 15 minutes in 500 parts of demineralised water in 
the presence of 0.25 part of Marseille soap. After being rinsed with 
running hot water (for 3 minutes) and centrifuged, the dyeing is dried in 
a cabinet dryer at about 70.degree.. A navy blue cotton dyeing is obtained 
showing good light- and wet-fastness properties which is stable towards 
oxidative influences. 
Application Example B 
To a dyebath containing in 300 parts of demineralised water 10 parts of 
Glauber's salt (calcined), 10 parts of cotton fabric (bleached) are added. 
The bath is heated to 40.degree. within 10 minutes, and 0.5 part of the 
dyestuff of Example 1 is added. After a further 30 minutes at 40.degree. 3 
parts of sodium carbonate (calcined) are added and dyeing is continued at 
40.degree. for a further 45 minutes. 
The dyed fabric is rinsed with running cold and then hot water and washed 
at the boil according to the method given in Application Example A. After 
rinsing and drying a navy blue cotton dyeing is obtained which has the 
same good fastness properties as indicated in Application Example A. 
Similarly, the dyestuffs of Examples 2-54 or mixtures of the exemplified 
dyestuffs may be employed to dye cotton in accordance with the method 
described in Application Example A or B. The cotton dyeings thus obtained 
are navy blue and show good fastness properties. 
Application Example C 
A printing paste consisting of 
______________________________________ 
40 parts of the dyestuff of Example 1 
100 parts of urea 
350 parts of water 
500 parts of a 4% sodium alginate thickener and 
10 parts of sodium bicarbonate 
1000 parts in all 
______________________________________ 
is applied to cotton fabric in accordance with conventional printing 
methods. 
The printed fabric is dried and fixed in steam at 102.degree.-104.degree. 
for 4-8 minutes. It is rinsed in cold and then hot water, washed at the 
boil (according to the method described in Application Example A) and 
dried. A navy blue print is obtained which has good general fastness 
properties. 
Similarly, the dyestuffs of Examples 2 to 54 or mixtures of the exemplified 
dyestuffs may be employed to print cotton in accordance with the method 
given in Application Example C. All prints obtained are navy blue and show 
good fastness properties.