Phthalocyanine reactive dyestuffs of the formula ##STR1## wherein Pc, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, B, R.sub.6, R.sub.7, R.sub.8, a, b and c have the meaning indicated in the description, and their use for dyeing textile materials containing hydroxyl groups and textile materials containing nitrogen, in particular textile materials made of natural and regenerated cellulose and furthermore made of wool, silk and synthetic polyamide fibers and polyurethane fibers. The resulting dyeings are distinguished by excellent fastness to wet processing.

The invention relates to new water-soluble phthalocyanine dyestuffs which, 
in the form of their free acids, correspond to the formula 
##STR2## 
wherein Pc=the radical of a copper phthalocyanine or nickel 
phthalocyanine, 
R.sub.1 and R.sub.2 =H or optionally substituted alkyl, 
R.sub.3, R.sub.4 and R.sub.5 =H or optionally substituted alkyl, 
R.sub.6, R.sub.7 and R.sub.8 =H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 
-alkoxy, SO.sub.3 H or COOH, with the proviso that at least one of the 
radicals=SO.sub.3 H or COOH, 
B=a bridge member, 
a=1 to 3; 
b=0 to 2; 
c=1 or 2 and 
a+b+c.ltoreq.4. 
and their mixtures as well as processes for their preparation and use. 
Each sulphonic acid or sulphonamide group in the dye-stuffs of the formula 
(I) is bonded to a different benzene ring of the phthalocyanine, in the 
3-position or 4-position. 
The radicals R.sub.1 and R.sub.2 ; R.sub.3 -R.sub.5 and R.sub.6 -R.sub.8 
can be identical or different. 
Examples which may be mentioned of optionally substituted alkyl radicals 
R.sub.1 and R.sub.2 are: C.sub.1 -C.sub.5 -alkyl radicals, such as methyl, 
ethyl, propyl, butyl and amyl, .beta.-hydroxyethyl and 
.gamma.-hydroxypropyl, .beta.-carboxyethyl and .beta.-sulphoethyl. 
Examples of optionally substituted alkyl radicals R.sub.3, R.sub.4 and 
R.sub.5 are, besides hydrogen, C.sub.1 -C.sub.5 -alkyl radicals, such as 
methyl, ethyl and propyl radicals, .beta.-hydroxyethyl and 
.gamma.-hydroxypropyl. 
The bridge members B can be of an aromatic, aliphatic or araliphatic 
nature. They can be optionally substituted, for example by C.sub.1 
-C.sub.4 -alkyl groups, C.sub.1 -C.sub.4 -alkoxy groups, halogen atoms, 
sulpho groups or carboxyl groups, or interrupted by keto groups, sulphone 
groups, carboxamido groups, urea groups, sulphonamide groups, amino 
groups, imino groups or oxygen atoms. 
Examples which may be mentioned of aromatic bridge members are: 
1,2-phenylene, 1,3-phenylene-, 1,4-phenylene, 1,4-naphthylene, 
1,5-naphthylene, 4-methyl-1,4-phenylene, 2-methyl-1,4-phenylene, 
2-methyl-5-chloro-1,4-phenylene, 4-methoxy-1,3-phenylene, 
3-methoxy-1,4-phenylene, 4-chloro-1,3-phenylene, 2-chloro-1,4-phenylene, 
5-carboxamido-1,3-phenylene, 2-carboxy-1,4-phenylene, 
2-carboxy-1,5-phenylene, 3-carboxy-1,5-phenylene, 4-sulpho-1,3-phenylene, 
3-sulpho-1,4-phenylene and 2-methyl-5-sulpho-1,3-phenylene. 
Examples which may be mentioned of aliphatic bridge members are: 
##STR3## 
Further examples of bridge members which may be mentioned are: 
##STR4## 
Those dyestuffs of the general formula (I) wherein 
Pc=the radical of a copper phthalocyanine or nickel phthalocyanine, 
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 =hydrogen, methyl or ethyl, 
R.sub.5 =hydrogen, 
B=1,2-phenylene, 1,3-phenylene, 1,4-phenylene or C.sub.2 -C.sub.6 -alkylene 
(straight-chain or branched), optionally substituted by C.sub.1 -C.sub.4 
-alkyl groups, C.sub.1 -C.sub.4 -alkoxy groups or halogen atoms, 
R.sub.6, R.sub.7 and R.sub.8 =hydrogen, methyl, ethyl, methoxy, SO.sub.3 H 
or COOH, at least one of these radicals being SO.sub.3 H or COOH. 
a=1-3; 
b=0-2; 
c=1; and 
a+b+c=2-4, 
form a preferred group within the dyestuffs according to the invention. 
Those dyestuffs of the general formula (I) wherein 
Pc=the radical of a copper phthalocyanine or nickel phthalocyanine, 
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 =hydrogen, methyl or ethyl, 
R.sub.5 =hydrogen, 
B=1,2-phenylene, 1,3-phenylene, 1,4-phenylene or C.sub.2 -C.sub.6 -alkylene 
(straight-chain or branched), optionally substituted by C.sub.1 -C.sub.4 
-alkyl groups, C.sub.1 -C.sub.4 -alkoxy groups or halogen atoms, 
R.sub.6, R.sub.7 and R.sub.8 =hydrogen, methyl, ethyl, methoxy, SO.sub.3 H 
or COOH, at least one of these radicals being SO.sub.3 H or COOH. 
1&lt;a&lt;3, 
b&lt;0, 
c=1; and 
a+b+c=3 or 4, 
form a particularly preferred group within the dyestuffs according to the 
invention 
Those dyestuffs of the general formula (I) wherein 
Pc=the radical of a copper phthalocyanine or nickel phthalocyanine, 
R.sub.3 and R.sub.4 =hydrogen, methyl or ethyl, 
R.sub.5 =hydrogen, 
B=1,2-phenylene, 1,3-phenylene, 1,4-phenylene or C.sub.2 -C.sub.6 -alkylene 
(straight-chain or branched), optionally substituted by C.sub.1 -C.sub.4 
-alkyl groups, C.sub.1 -C.sub.4 -alkoxy groups or halogen atoms, 
R.sub.6, R.sub.7 and R.sub.8 =hydrogen, methyl, ethyl, methoxy, SO.sub.3 H 
or COOH, at least one of these radicals being SO.sub.3 H or COOH. 
a=1 or 2, 
b=0, 
c=1 and 
a+c=2 or 3 
also form a particularly preferred group within the dyestuffs according to 
the invention. 
The new dyestuffs of the formula (I) are prepared by condensation of 
suitable starting components. The most advantageous process consists in 
reacting dyestuffs which, in the form of their free acids, correspond to 
the formula 
##STR5## 
with compounds of the general formula 
##STR6## 
wherein Pc, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, 
R.sub.8, B, a, b and c have the meaning indicated above. 
However, it is also possible first to react the dye-stuffs of the formula 
(II) with trifluorotriazine and to react the resulting intermediate 
product with a compound of the formula 
##STR7## 
wherein R.sub.5, R.sub.6, R.sub.7 and R.sub.8 have the meaning indicated 
above. 
These reactions are acylation reactions and can be carried out in an 
aqueous, aqueous-organic or organic, preferably weakly acid to weakly 
alkaline, medium at temperatures from -10.degree. C. to +80.degree. C., 
preferably -5.degree. C. to +10.degree. C. 
The phthalocyanine compounds of the formula (II) used in the process 
according to the invention can be prepared by reacting a 
phthalocyaninesulphonic acid chloride, preferably in the form of an 
aqueous suspension, of the formula 
##STR8## 
wherein Pc has the meaning indicated above, 
m designates the numbers 0, 1 or 2 and 
n designates the numbers 2, 3 or 4, the sum of m and n being not greater 
than 4, 
with diamines or, preferably, monoacylated diamines of the formula 
##STR9## 
and optionally with a compound of the formula 
##STR10## 
wherein 
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the meaning indicated above, 
and, if monoacylated diamines of the formula (VIb) are used, subjecting 
the terminal acylamino group of the resulting phthalocyanine compounds to 
acid or alkaline saponification. Unreacted sulphonic acid chloride groups 
are converted into sulphonic acid groups in this reaction. 
Phthalocyaninesulphonyl chlorides and phthalocyaninesulphonyl 
chloride-sulphonic acids of the formula (V) can be obtained by treating 
the corresponding phthalocyanine or the phthalocyaninesulphonic acid with 
chlorosulphonic acid and, if appropriate, an acid halide, such as thionyl 
chloride, phosphorus pentachloride, phosphorus oxychloride or phosphorus 
trichloride, as described in British Pat. Nos. 708,543, 784,834 and 
785,629 and in U.S. Pat. No. 2,219,330. 
Uniform phthalocyanine dyestuffs can be used according to the invention, 
that is to say those in which the letters a, b and c characterise the 
numbers 0, 1, 2 or 3. In addition, however, mixtures of these dyestuffs 
can also be used. Mixtures of this type sometimes show particular 
advantages with respect to solubility and substantivity. In such mixtures, 
the averaged value of the numbers varies. 
Mixtures of this type according to the invention are prepared, for example, 
from two or more, in each case uniform, end dyestuffs of the formula (I), 
or particularly advantageously by using a mixture of starting components. 
The latter is frequently automatically formed, since the 
phthalocyaninesulphinic acid chloride-sulphonic acids (V) are frequently 
obtained industrially in the form of mixtures with respect to the degree 
of sulphonation and their proportion of sulphonic acid chloride groups and 
sulphonic acid groups. 
Examples which may be mentioned of suitable monoacylated diamines of the 
formula (VIb) and suitable diamines of the formula (VIa) are: 
2-amino-acetanilide, 3-aminoformanilide, 3-aminoacetanilide, 
4-aminoformanilide, 4-aminoacetanilide, 1-amino-4-acetylaminonaphthalene, 
1-amino-5-acetylaminonaphthalene, 3-aminophenyloxymic acid, 
4-methyl-3-aminoacetanilide, 4-methyl-3-amino-phenyloxamic acid, 
5-chloro-4-amino-2-methyl-acetanilide, 4-methoxy-3-amino-acetanilide, 
4-amino-3-methoxy-acetanilide, 4-amino-2,5-dichloro-acetanilide, 
N-methyl-N-4-aminophenyl-acetamide, 4-amino-2-chloro-acetanilide, 
4-acetylamino-2-amino-benzoic acid, 5-acetylamino-2-amino-benzoic acid, 
1,4-diaminobenzene-2-sulphonic acid, 1,3-diaminobenzene-3-sulphonic acid, 
5-acetylamino-3-aminobenzoic acid, monoacetyl-ethylenediamine, 
monoacetyl-propylene-1,3-diamine, monoacetylbutylene-1,4-diamine, 
N-methyl-N-3-aminopropyl-acetamide, 
N-methyl-N-.beta.-methylaminoethylacetamide and 
B-(.beta.-aminoethyl)-N'-(3-aminophenyl)-urea. 
The new dyestuffs are extremely valuable products which are suitable for 
the most diverse application purposes. As water-soluble compounds, they 
are of interest for dyeing textile materials containing hydroxyl groups 
and textile materials containing nitrogen, in particular textile materials 
made of natural and regenerated cellulose, and furthermore made of wool, 
silk and synthetic polyamide fibres and polyurethane fibres. They are 
particularly suitable for use as reactive dyestuffs for dyeing cellulose 
materials by techniques which have recently been disclosed for this. The 
resulting fastness properties, in particular fastness to wet processing, 
are excellent. 
For dyeing cellulose, the dyestuffs are preferably employed in an aqueous 
solution, to which substances having an alkaline reaction, such as alkali 
metal hydroxide or alkali metal carbonate, or compounds which are 
converted into substances having an alkaline reaction, such as alkali 
metal bicarbonate or Cl.sub.3 C--COONa, can be added. Further auxiliaries 
can be added to the solution, but they should not react with the dyestuffs 
in an undesired manner. Examples of such additives are surface-active 
substances, such as alkylsulphates, or substances which prevent migration 
of the dyestuff or dyeing auxiliaries, such as urea, or inert thickeners, 
such as oil-in-water emulsions, tragacanth, starch, alginate or 
methylcellulose. 
The solutions or pastes thus prepared are applied, for example by padding 
on a padder (short liquor) or by printing, onto the material to be dyed 
and are then heated to an elevated temperature, preferably 40.degree. to 
150.degree. C., for some time. The heating can be carried out in a hot 
flue, in a steam apparatus, on heated rollers or by introducing the 
material into heated concentrated salt baths, either a single process or 
any desired sequence of successive processes being carried out. 
If a padding or dye liquor without alkali is used, the dry goods are 
subsequently passed through a solution having an alkaline reaction, to 
which sodium chloride or sodium sulphate decahydrate is added. The salt 
addition in this case decreases the migration of the dyestuff from the 
fibre. 
The material to be dyed can also be pretreated with one of the 
abovementioned acid-binding agents and then treated with the solution or 
paste of the dyestuff and finally, as indicated, the dyestuff is fixed at 
elevated temperature. 
For dyeing from a long liquor, the material is introduced into an aqueous 
solution of the dyestuff (liquor ratio 1:5 to 1:40) at room temperature 
and dyeing is carried out for 40 to 90 minutes, if appropriate increasing 
the temperature up to 95.degree. C. and if appropriate adding, in 
portions, a salt, for example sodium sulphate, and then alkali, for 
example sodium phosphates, sodium carbonate, NaOH or KOH. 
The chemical reaction between dyestuff and fibre occurs here. After the 
chemical fixing has ended, the dyed material is rinsed hot and then 
soaped, non-fixed residues of the dyestuff being removed. Dyeings which 
are outstandingly fast, in particular fast to wet processing and light, 
are obtained. 
In the so-called pad-cold batch process, subsequent heating of the padded 
fabric can be spared by storing the fabric at room temperature for some 
time, for example 2 to 20 hours. In this process, a stronger alkali is 
used than in the dyeing process, described above, from a long liquor. 
For printing materials containing hydroxyl groups, a printing paste 
consisting of the dyestuff solution, a thickener, such as sodium alginate, 
and a compound which has an alkaline reaction or which splits off an 
alkali on heating, such as sodium carbonate, sodium phosphate, potassium 
carbonate, potassium acetate or sodium bicarbonate and potassium 
bicarbonate, is used and the printed material is rinsed and soaped. 
Textile materials containing amine groups, such as wool, silk and synthetic 
polyamide fibres and polyurethane fibres, are in general dyed, in an acid 
to neutral region, by dyeing methods which are customary for these 
materials. 
The dyeings obtainable with the new dyestuffs are in general distinguished 
by good to very good fastness properties, in particular by excellent 
fastness to wet processing.

EXAMPLE 1 
3.46 g of 3-aminobenzene-sulphonic acid are dissolved in 150 ml of water at 
pH 3.5, a little sodium hydroxide solution being added. 2.9 g of 
2,4,6-trifluorotriazine are added dropwise to this solution at 
0.degree.-5.degree. in the course of 5 minutes, whilst maintaining a pH 
value of 3.2-3.6 with the aid of 1 N NaHCO.sub.3 solution, and the mixture 
is subsequently stirred at 0.degree.-5.degree. C. for a further 5 minutes, 
whilst maintaining the pH value indicated. 
19.68 g of the dyestuff of the formula 
##STR11## 
(obtained by reacting Cu-Pc-(3)-(SO.sub.2 Cl/SO.sub.3 H).sub.4 with 
3-aminoformanilide and ammonia and then saponifying the formylamino group) 
are dissolved in 400 parts of water at pH 6 with the aid of sodium 
hydroxide solution. After cooling the solution, the 
difluorotriazinylaminobenzenesulphonic acid solution obtained according to 
paragraph 1 is allowed to run in at 0.degree.-5.degree. C. in the course 
of 5 minutes, whilst maintaining a pH value of 6.0-6.5. After the 
condensation reaction has ended, the dyestuff is salted out with KCl, 
filtered off, rinsed with dilute KCl solution and dried at 
50.degree.-60.degree. C. The dyestuff which, in the form of its K salt, 
corresponds to the formula 
##STR12## 
is obtained in virtually quantitative yield. It dyes cotton in turquoise 
blue shades. 
If the procedure followed is as described in paragraph 1 and 2 but the 
3-aminobenzenesulphonic acid used in paragraph 1 is replaced by the same 
amount of 4-aminobenzenesulphonic acid, the dyestuff which, in the form of 
its K salt, corresponds to the formula 
##STR13## 
and which dyes cotton in turquoise blue shades is obtained, also in 
virtually quantitative yield. 
Further valuable reactive dyestuffs are obtained in an analogous manner if 
the aminobenzenesulphonic acids mentioned in column 3 of Table 1 which 
follows are acylated with 2,4,6-trifluoro-1,3,5-triazine and the resulting 
difluorotriazinylaminophenylsulphonic acid is subjected to a condensation 
reaction with the aminophthalocyanine derivatives formulated in column 2. 
TABLE 1 
__________________________________________________________________________ 
Aminophthalocyanine Colour shade 
No. 
derivative Aminobenzenesulphonic acid 
on cellulose 
__________________________________________________________________________ 
(1) 
##STR14## 3-aminobenzenesulphonic acid 
turquoise blue 
(2) 
##STR15## 3-aminobenzenesulphonic acid 
turquoise blue 
(3) 
##STR16## 3-aminobenzenesulphonic acid 
turquoise blue 
(4) 
##STR17## 4-aminobenzenesulphonic acid 
turquoise blue 
(5) 
##STR18## 3-aminobenzenesulphonic acid 
turquoise blue 
(6) 
##STR19## 3-aminobenzenesulphonic acid 
turquoise blue 
(7) 
##STR20## 3-aminobenzenesulphonic acid 
bluish-tinged green 
(8) 
##STR21## 3-aminobenzenesulphonic acid 
bluish-tinged green 
(9) 
##STR22## 1-aminobenzene-3,4-disulphonic 
turquoise blue 
(10) 
##STR23## 3-aminobenzenesulphonic acid 
turquoise blue 
(11) 
##STR24## 3-amino-4-methyl-benzenesulphonic acid 
turquoise blue 
(12) 
##STR25## 4-amino-2-methyl-benzenesulphonic acid 
turquoise blue 
(13) 
##STR26## 5-amino-2-methyl-benzenesulphonic acid 
turquoise blue 
__________________________________________________________________________ 
EXAMPLE 2 
3.5 g of 3-aminobenzoic acid are dissolved in 150 ml of water, 17 ml of 1 N 
hydrochloric acid being added. 3.5 g of 2,4,6-trifluoro-1,3,5-triazine are 
added dropwise at 0.degree.-3.degree. C. in the course of 15 minutes, the 
pH value of the suspension formed being kept at 3.0-4.0 by simultaneously 
adding 1 N NaHCO.sub.3 solution. 
19.68 g of the dyestuff of the formula 
##STR27## 
(obtained by reacting Cu-Pc-(3)-(SO.sub.2 Cl/SO.sub.3 H).sub.4 with 
3-aminoformanilide and ammonia and then saponifying the formylamino group) 
are dissolved in 400 ml of water at pH 6 with the aid of sodium hydroxide 
solution. After cooling the solution, the suspension of 
difluorotriazinylaminobenzoic acid obtained according to paragraph 1 is 
allowed to run in at 0.degree.-5.degree. C. in the course of 15 to 20 
minutes, whilst maintaining a pH value of 6.0-7.0. After the condensation 
reaction has ended, the dyestuff is salted out with NaCl, filtered off, 
rinsed with dilute NaCl solution and dried at 50.degree.-60.degree. C. The 
dyestuff which, in the form of its Na salt, corresponds to the formula 
##STR28## 
is obtained in virtually quantitative yield. It dyes cotton in turquoise 
blue shades. 
If the procedure followed is as described in paragraph 1 and 2 but 25 ml of 
1 N hydrochloric acid and 3.5 g of 4-aminobezoic acid are used in the 
acylation of the triazine (paragraph 1), the dyestuff of the formula 
##STR29## 
is obtained, also in virtually quantitative yield. The dyestuff dyes 
cotton in turquoise blue shades. 
Further valuable reactive dyestuffs are obtained in an analogous manner if 
the aminobenzoic acid given in column 3 of Table 2 which follows are 
acylated with 2,4,6-trifluoro-1,3,5-triazine and the resulting 
difluorotriazinylaminobenzoic acids are subjected to a condensation 
reaction with the aminophthalocyanine derivatives given in column 2. 
TABLE 2 
__________________________________________________________________________ 
No. 
Aminophthalocyanine derivative 
Aminobenzoic acid 
Colour shade on 
__________________________________________________________________________ 
cellulose 
(1) 
##STR30## 3-aminobenzoic acid 
turquoise blue 
(2) 
##STR31## 3-aminobenzoic acid 
bluish-tinged green 
(3) 
##STR32## 4-aminobenzoic acid 
turquoise blue 
(4) 
##STR33## 3-aminobenzoic acid 
turquoise blue 
(5) 
##STR34## 4-aminobenzoic acid 
turquoise blue 
(6) 
##STR35## 4-aminobenzoic acid 
turquoise blue 
(7) 
##STR36## 4-aminophthalic acid 
turquoise blue 
(8) 
##STR37## 3-aminobenzoic acid 
bluish-tinged green 
(9) 
##STR38## 3-aminobenzoic acid 
turquoise blue 
(10) 
##STR39## 4-aminobenzoic acid 
turquoise blue 
__________________________________________________________________________ 
EXAMPLE 3 
3.46 g of 3-aminobenzenesulphonic acid are dissolved in 150 ml of water at 
pH 3.5, a little sodium hydroxide solution being added. 2.9 g of 
2,4,6-trifluoro-1,3,5-triazine are added dropwise to this solution at 
0.degree.-5.degree. C. in the course of 5 minutes, a pH value of 3.2-3.6 
being maintained with the aid of 1 N NaHCO.sub.3 solution, and the mixture 
is subsequently stirred at 0.degree.-5.degree. C. for a further 5 minutes, 
whilst maintaining the pH value indicated. 
19.02 g of the dyestuff of the formula 
##STR40## 
(obtained by reacting Cu-Pc-(3)-(SO.sub.2 Cl/SO.sub.3 H).sub.4 with 
monoacetylethylenediamine and ammonia and then saponifying the acetylamino 
group) are dissolved in 300 ml of water at pH 8.5 with the aid of sodium 
hydroxide solution. After cooling the solution, the 
difluorotriazinylaminobenzenesulphonic acid solution obtained according to 
paragraph 1 is allowed to run in at 0.degree.-5.degree. C. in the course 
of 10 minutes, whilst maintaining a pH value of 8.0-8.5. After the 
condensation reaction has ended, the pH value of the solution is adjusted 
to 6 and the dyestuff is salted out with KCl, filtered off, rinsed with 
dilute KCl solution and dried at 50.degree.-60.degree. C. The dyestuff 
which, in the form of its K salt, corresponds to the formula 
##STR41## 
is obtained in very good yield. The dyestuff dyes cotton in turquoise blue 
shades. 
If the procedure followed is as described in paragraph 1 and 2 but the 
3-aminobenzenesulphonic acid used in paragraph 1 is replaced by the same 
amount of 4-aminobenzenesulphonic acid, the dyestuff of the formula 
##STR42## 
is obtained, also in very good yield. It dyes cotton in turquoise blue 
shades. 
If the procedure followed is analogous to that in paragraph 2 but the 
aminophthalocyanine derivative used there is reacted with the suspension 
of difluorotriazinyl-aminobenzoic acid obtained according to Example 2, 
paragraph 1, the dyestuff of the formula 
##STR43## 
which also dyes cotton in turquoise blue shades is obtained. 
Further valuable reactive dyestuffs are obtained in an analogous manner if 
the aminobenzenesulphonic acids or aminobenzoic acids given in column 3 of 
Table 3 which follows are acylated with 2,4,6-trifluoro-1,3,5-triazine and 
the resulting difluorotriazine derivatives are subjected to a condensation 
reaction with the aminophthalocyanine derivatives given in column 2. 
TABLE 3 
__________________________________________________________________________ 
Colour shade on 
No. 
Aminophthalocyanine derivative 
Amino acid cellulose 
__________________________________________________________________________ 
(1) 
##STR44## 3-aminobenzenesulphonic acid 
turquoise blue 
(2) 
##STR45## 3-aminobenzenesulphonic acid 
turquoise blue 
(3) 
##STR46## 4-aminobenzenesulphonic acid 
turquoise blue 
(4) 
##STR47## 3-aminobenzoic acid 
turquoise blue 
(5) 
##STR48## 4-aminobenzenephonic acid 
turquoise blue 
(6) 
##STR49## 4-aminobenzoic acid 
turquoise blue 
(7) 
##STR50## 3-amino-4-methyl-benzene- sulphonic 
turquoise blue 
(8) 
##STR51## 4-amino-3-chlorobenzene- sulphonic 
turquoise blue 
(9) 
##STR52## 5-amino-3-methyl-benzene- sulphonic 
turquoise blue 
(10) 
##STR53## 3-aminobenzenesulphonic acid 
turquoise blue 
__________________________________________________________________________ 
DYEING EXAMPLE 1 
220 ml of water at a temperature of 20.degree.-25.degree. C. are initially 
introduced into a dyeing beaker of 500 ml capacity, which is in a 
waterbath which can be heated. 0.3 g of the dyestuff obtained according to 
Example 1, paragraph 2 is mixed thoroughly into a paste with 2 ml of cold 
water, and 48 ml of hot water (70.degree. C.) are added. The dyestuff 
solution, which has a pH value of 7-8, is added to the water initially 
intoduced, 10 g of cotton yarn being continuously kept in motion in this 
dye liquor. The temperature of the dye liquor is increased to 60.degree. 
C. in the course of 10 minutes, 15 g of sodium sulphate (anhydrous) are 
added and dyeing is continued for 30 minutes. 2 g of sodium carbonate are 
then added to the dye liquor and dyeing is carried out at 60.degree. C. 
for 60 minutes. The dyed material is then removed from the dye liquor, the 
adhering liquor is removed by wringing out or squeezing off and the 
material is rinsed thoroughly, first with cold water and then with hot 
water, until the rinsing liquor is no longer stained. The dyed material is 
then soaped in 500 ml of a liquor containing 0.5 g of sodium 
alkylsulphonate for 20 minutes at the boiling point, again and dried in a 
drying cabinet at 60.degree.-70.degree. C. The cotton is dyed in a clear 
turquoise blue shade which is fast to wet processing. 
DYEING EXAMPLE 2 
3 g of the dyestuff which is obtained according to Example 1, paragraph 2, 
are stirred with 5 g of urea and 1 g of sodium m-nitrobenzene-sulphonate, 
and the mixture is mixed thoroughly into a paste with 10 ml of water at a 
temperature of 20.degree.-25.degree. C. and dissolved with 80 ml of water, 
at a temperature of 20.degree. C., at pH 7-8, whilst stirring. 20 ml of a 
10% strength sodium carbonate solution are added to this solution. 20 g of 
cotton fabric are padded with the padding liquor thus obtained on a 
laboratory padder, the rollers of which are pressed against one another 
with a pressure such that the liquor pick-up of the cotton fabric is about 
80% of its dry weight. The fabric thus padded is stretched across a 
stenter frame, dried at 60.degree.-70.degree. C. for 15 minutes in a 
drying cabinet and then steamed at 102.degree. C. for 3 minutes. The dyed 
material is then rinsed thoroughly, first with cold water and then with 
hot water, until the rinsing liquor is no longer stained. The dyed 
material is then soaped in 500 ml of a liquor containing 0.5 g of sodium 
alkylsulphonate for 20 minutes at the boiling point, again and dried at 
60.degree.-70.degree. C. in a drying cabinet. 
The dyestuff is absorbed to give a clear turquoise blue shade which is fast 
to wet processing. 
DYEING EXAMPLE 3 
A 20 g hank of wool is introduced, at 40.degree. C., into a dyebath which 
consists of 0.5 g of the dyestuff obtained according to Example 1, 
paragraph 2 (dissolved at pH 7-8) 3.0 g of a polyglycol ether, prepared 
according to DAS (German Published Specification) No. 1,041,003, Example 
9, 5.0 g of sodium sulphate and 1.2 g of 30% strength acetic acid per 
liter, and the bath is warmed to 80.degree. C. in the course of 15 
minutes. The bath is allowed to remain at this temperature for 30 minutes 
and then warmed to the boiling point and this temperature is maintained 
for about one hour. After rinsing the wool with water, a turquoise blue 
dyeing which is fast to potting and milling is obtained. 
PRINTING EXAMPLE 
A piece of cotton is printed with a printing paste consisting of 50 g of 
the dyestuff of Example 1, paragraph 2, 150 g of urea, 20 g of sodium 
bicarbonate, 10 g of sodium m-nitrobenzene-sulphonate, 450 g of a highly 
viscous alginate thickener and 320 g of water and steamed in a steamer, 
for example of the Mather-Platt type, at 103.degree. C. The print is then 
rinsed with cold water, then with hot water and finally again with cold 
water. A turquoise blue print which is fast to wet processing is obtained.