Disperse azo dyes containing N-phenoxyalkyleneanilines as coupling components

The present invention relates to disperse dyes, to a process for their 
preparation and to their use for dyeing synthetic organic material. 
The dyes according to the invention have the formula 
##STR2## 
in which D is the radical of a substituted or unsubstituted, homocyclic or 
heterocyclic diazo component belonging to the series comprising thienyl, 
thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 
benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl or phenyl, 
X is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, 
acylamino, halogen or a group of the formula --NH--CO--NHQ in which Q is 
hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl, 
Y is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, 
C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 
-alkoxy-C.sub.1 -C.sub.4 -alkoxy, 
R is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl or 
phenyl, or Y and R, together with the nitrogen atom and the two C atoms 
linking them, form a 5-membered ring or 6-membered ring, 
B is a linear or branched C.sub.2 -C.sub.6 -alkylene radical, 
W is halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, 
Z is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or nitro 
and m and n are each 0, 1, 2 or 3. 
D forms the radical of a homocyclic or heterocyclic diazo component 
belonging to the series comprising thienyl, thiazolyl, isothiazolyl, 
1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, benzothiazolyl, benzoisothiazolyl, 
pyrazolyl, imidazolyl or phenyl. Each of these systems can carry further 
substituents, such as alkyl, alkoxy or alkylthio having in each case 1 to 
4 carbon atoms, phenyl, electronegative groups, such as halogen, 
especially chlorine or bromine, trifluoromethyl, cyano, nitro, acyl, 
benzoyl, carboalkoxy, especially carbomethoxy or carboethoxy, 
alkylsulfonyl having 1 to 4 carbon atoms, phenylsulfonyl, phenoxysulfonyl, 
sulfonamide or arylazo, especially phenylazo. Any 2 adjacent substituents 
of the ring systems mentioned can together also form further fused rings, 
for example phenyl rings or cyclic imides. 
D is preferably a benzothiazolyl or phenyl radical which is unsubstituted 
or is monosubstituted or disubstituted by one of the abovementioned 
radicals. 
As a benzothiazolyl radical, D is, in particular, an unsubstituted 
benzothiazolyl radical or a benzothiazolyl radical which is 
monosubstituted or polysubstituted by methyl, methoxy, chlorine, 
methylsulfonyl or nitro. 
The preferred meaning of D is phenyl which is substituted by not more than 
4 substituents, which may be different, from the enumeration mentioned 
above. Of the substituents enumerated, electronegative substituents are 
preferred. These can be, in particular, cyano, methylsulfonyl, 
ethylsulfonyl, nitro, chlorine, bromine, formyl, acetyl, benzoyl, 
carbomethoxy, carboethoxy, methoxy, ethoxy or phenylazo. 
In this application, alkyl groups are to be understood generally as linear 
or branched alkyl groups. They are, for example, methyl, ethyl, propyl, 
i-propyl, butyl, i-butyl, tert.-butyl, amyl, tert.-amyl 
(1,1-dimethylpropyl), 1,1,3,3-tetramethylbutyl, hexyl, 1-methylpentyl, 
neopentyl, 1-, 2- or 3-methylhexyl, heptyl, n-octyl, tert.-octyl, 
2-ethylhexyl, n-nonyl, isononyl, decyl, dodecyl, cyclopentyl, cyclohexyl 
or methylcyclohexyl and the relevant isomers. 
These alkyl radicals can be substituted, for example by hydroxyl, alkoxy 
having 1 to 4 carbon atoms, especially methoxy, cyano or phenyl. Other 
suitable substituents are halogen, such as fluorine, chlorine or bromine, 
or --CO--U or --O--CO--U in which U is alkyl having 1 to 6 carbon atoms or 
phenyl. 
Suitable alkenyl radicals are those derived from the alkyl radicals listed 
above by the replacement of at least one single bond by a double bond. 
Examples of suitable radicals are ethenyl or propenyl. 
Examples of suitable alkoxy radicals are methoxy, ethoxy, propoxy, 
isopropoxy, n-butoxy, i-butoxy or tert.-butoxy. 
The following are examples of suitable substituted alkyl radicals: 
methoxymethyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, n-propoxymethyl, 
isopropoxymethyl, butoxymethyl, butoxyethyl, butoxypropyl, ethoxypentyl, 
methoxybutyl, ethoxypentyl, 2-hydroxyethoxypentyl, cyanoethyl, 
hydroxyethyl or acetoxyethyl. 
The alkylene radicals B can also be linear or branched or substituted. 
Examples of suitable radicals are ethylene, 1,3-propylene, 1,5-pentylene, 
1,2-propylene, 1,2-butylene, 1,6-hexylene, 2-hydroxy-1,3-propylene or 
2-chloro-1,3-propylene. 
If X is an acylamino group, it is, for example, a group of the formula 
EQU --NH--V--R.sup.1 
in which V is --CO-- or --SO.sub.2 -- and R.sup.1 is alkyl or phenyl each 
of which is substituted or unsubstituted. 
Examples of the acyl radical are the acetyl, propionyl-, 
2-chloroethylcarbonyl-, 2-bromoethylcarbonyl-, phenylcarbonyl-, 
2-methoxycarbonylethylcarbonyl-, 2-ethoxycarbonylethylcarbonyl-, 
methoxycarbonyl-, ethoxycarbonyl-, phenoxycarbonyl, methoxyethylcarbonyl-, 
hydroxyethylcarbonyl-, methylsulfonyl- or ethylsulfonyl radical. 
If X is a group of the formula --NH--CO--NHQ, it is, for example, the 
ureido, methylureido, ethylureido or phenylureido group. 
In this application, phenyl radicals are to be understood, in general, as 
meaning unsubstituted or substituted phenyl radicals. Examples of suitable 
substituents are C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, bromo, 
chloro, nitro or C.sub.1 -C.sub.4 -alkylcarbonylamino. 
In this application generally, halogen is fluorine, bromine or, in 
particular, chlorine. 
R and Y, together with the nitrogen atom and the two C atoms linking them, 
can form a 5-membered or 6-membered ring which can, if desired, contain an 
oxygen atom as a further heteroatom. Examples of suitable substituents for 
these rings are hydroxy, methyl, methoxy, chlorine or phenyl. Preferably, 
R and Y, together with the nitrogen atom and the two C atoms linking them, 
form a 6-membered ring which is unsubstituted or carries 1 to 4 methyl 
groups. These are, therefore, in particular dihydroquinoline or 
tetrahydroquinoline compounds having 0 to 4 methyl groups. 
In particularly preferred disperse dyestuffs D is a benzothiazolyl radical 
which is unsubstituted or is monosubstituted or disubstituted by chlorine 
or is a phenyl radical which is monosubstituted or disubstituted by nitro, 
chlorine, cyano, methylsulfonyl, ethylsulfonyl or phenylazo. 
The preferred meanings of X are hydrogen, methyl, methoxy, chlorine, 
bromine, acetylamino or ureido, hydrogen, methyl, chlorine and acetylamino 
being particularly preferred. Y is preferably chlorine, methyl, methoxy, 
methoxyethyl or methoxyethoxy or, in particular, hydrogen. The preferred 
meaning of R is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or 
substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy or phenyl. In 
particularly preferred compounds of the formula (1) R is methyl, ethyl or 
benzyl. 
B is preferably a linear or branched alkylene radical which has 2 to 4 
carbon atoms and which is unsubstituted or substituted by hydroxyl. The 
disperse dyestuffs of the formula (1) in which B is ethylene are 
particularly preferred. 
The preferred meanings of W are chlorine, methyl or methoxy, but compounds 
in which n is nought are particularly preferred. 
Z is preferably chlorine, methyl, methoxy or nitro, but compounds in which 
m is nought are particularly preferred. 
The phenylazo radical carrying the substituent Z is preferably located in 
the p-position relative to the oxygen. 
Dyes of the formula (1) which are of interest because of their good 
tinctorial properties are, in particular, those in which 
D is a benzothiazolyl radical which is unsubstituted or is monosubstituted 
or disubstituted by chlorine or is a phenyl radical which is 
monosubstituted or disubstituted by nitro, chlorine, cyano, 
methylsulfonyl, ethylsulfonyl or phenylazo, 
X is hydrogen, methyl, methoxy, chlorine, bromine, acetylamino or ureido, 
Y is chlorine, methyl, methoxy, methoxyethyl, methoxyethoxy or hydrogen and 
R is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or is substituted by 
hydroxyl, cyano, C.sub.1 -C.sub.4 -alkoxy or phenyl, 
B is a C.sub.2 -C.sub.4 -alkylene radical which is unsubstituted or 
substituted by hydroxyl, 
W is chlorine, methoxy or methyl, 
Z is chlorine, methyl, methoxy or nitro and m and n are each 0 or 1. 
Amongst these dyes which are of very particular interest are those in which 
X is methyl, acetylamino, chlorine or hydrogen, Y is hydrogen, R is 
methyl, ethyl or benzyl, B is ethylene and m and n are each nought. 
The compounds of the formula (1) are prepared in a manner known per se, for 
example by coupling a diazotized amine of the formula 
EQU D--NH.sub.2 ( 2) 
with a compound of the formula 
##STR3## 
in which D, X, Y, R, B, W, Z, m and n are as defined under the formula 
(1). 
The compounds of the formula (2) are known or can be prepared analogously 
to the preparation of similar compounds. 
The compounds of the formula (3) are novel and form a further subject of 
the present invention. They are prepared, for example, by reacting a 
hydroxyazobenzene of the formula 
##STR4## 
with a dihalogeno compound 
EQU Hal--B--Hal (5) 
to give a compound of the formula 
##STR5## 
and then reacting the latter with an aniline derivative of the formula 
##STR6## 
to give a compound of the formula (3). 
In the formulae (4) to (7), W, Z, B, X, Y, R, n and m are as defined under 
the formula (1) and Hal is chlorine or bromine, it being possible for the 
two halogen atoms to be identical or different. 
The compounds of the formula (4) and (5) are known or can be prepared in a 
known manner. The reaction of the compound (4) with the compound (5) is 
preferably carried out in an inert organic solvent and in the presence of 
a base. Examples of suitable inert organic solvents are compounds having a 
boiling point above 100.degree. C., such as alcohols, ethers, esters, 
nitrobenzene, a halogenobenzene, toluene, xylenes etc. Particularly 
suitable solvents are higher-boiling alcohols, such as tert.-butanol, and 
ethers of polyhydric alcohols, for example diethylene glycol monoethyl 
ether or monomethyl ether and also the corresponding diethers. 
The components (4) and (5) can be employed in a stoichiometric ratio, but 
an excess of one of the components, preferably the compound (5), often 
proves more advantageous. 
The reaction temperature is between about 80 and 150.degree. C., preferably 
between 100.degree. and 130.degree. C., and the reaction time is about 1 
to 20 hours, depending on the temperature and the reactants. When the 
reaction is complete, the excess of the component (5) which may have been 
employed is removed and the resulting compound of the formula (6) is then 
reacted with an aniline derivative of the formula (7). This reaction is 
also preferably carried out in one of the abovementioned solvents. The 
temperature is normally above 100.degree. C., in particular between 
120.degree. and 200.degree. C. and especially between 140.degree. and 
180.degree. C. The components (6) and (7) can be employed in a 
stoichiometric ratio, but normally the more readily accessible component, 
in most cases the aniline derivative (7), is employed in an excess, for 
example in a 10% excess. When the reaction is complete, the product is 
worked up in a customary manner, for example by removing the excess of the 
component (7) and the solvent and, if necessary, purifying the residue, 
for example by recrystallization. Both the reaction of the compounds (4) 
and (5) and the reaction of compounds (6) and (7) are carried out in the 
presence of a base, suitable bases being either organic or inorganic 
bases, for example pyridine, piperidine, triethylamine, sodium carbonate 
or bicarbonate or potassium carbonate or bicarbonate. This base is 
generally employed in a slight excess, for example in a 10% excess. 
The entire preparation of the compound (3) can also be carried out as a 
so-called one-pot reaction, by employing the same solvent for the two 
reaction stages and not isolating the compound (6). 
The diazotization of the compounds of the formula (2) and the coupling with 
the compounds of the formula (3) are carried out by the usual methods. 
The compounds, according to the invention, of the formula (1) can be used 
as dyes for dyeing and printing semi-synthetic and, in particular, 
synthetic, hydrophobic fibre materials, in particular textile materialss. 
Textile materials composed of mixed fabrics containing semi-synthetic or 
synthetic, hydrophobic textile materials of this type can also be dyed or 
printed by means of the compounds according to the invention. 
Suitable semi-synthetic textile materials are, in particular, cellulose 
21/2-acetate and cellulose triacetate. 
Synthetic, hydrophobic textile materials consist, in particular, of linear, 
aromatic polyesters, for example polyesters formed from terephthalic acid 
and glycols, especially ethylene glycol, or condensation products formed 
from terephthalic acid and 1,4-bis-(hydroxymethyl)-cyclohexane; polyesters 
composed of polycarbonates, for example those formed from 
.alpha.,.alpha.-dimethyl-4,4'-dihydroxydiphenylmethane and phosgene, and 
polyesters composed of fibres based on polyvinyl chloride or polyamides. 
The application of the compounds according to the invention to the textile 
materials is carried out by known dyeing processes. For example, polyester 
fibre materials are dyed by the exhaustion process from an aqueous 
dispersion in the presence of customary anionic or nonionic dispersing 
agents and, if desired, customary swelling agents (carriers) at 
temperatures between 80.degree. and 140.degree. C. Cellulose 21/2-acetate 
is preferably dyed between about 65.degree. and 85.degree. C. and 
cellulose triacetate is preferably dyed at temperatures up to 115.degree. 
C. 
The novel dyes dye wool and cotton present in the dyebath at the same time 
only slightly or not at all (very good reserve), so that they can also be 
used satisfactorily for dyeing polyester/wool and polyester/cellulose 
fibre mixed fabrics. 
The dyes according to the invention are also suitable for dyeing by the 
thermosol process. 
The textile material mentioned can be present in these processes in a very 
wide variety of processing forms, for example as fibres, threads or 
nonwovens or as woven or knitted fabrics. 
It is advantageous to convert the dyes according to the invention, before 
use, into a dyeing preparation. This is effected by grinding the dye so 
that its average particle size is between 0.01 and 10 microns. The 
grinding can be carried out in the presence of dispersing agents. For 
example, the dried dye is ground with a dispersing agent or is kneaded in 
the form of paste with a dispersing agent and is then dried in vacuo or by 
atomizing. The preparations thus obtained can be used for dyeing and 
printing after the addition of water. 
In printing, the customary thickeners will be used, for example modified or 
unmodified natural products, for example alginates, British gum, gum 
arabic, crystal gum, locust bean flour, tragacanth, 
carboxymethylcellulose, hydroxyethyl-cellulose or starch, or synthetic 
products, for example polyacrylamides, polyacrylic acid or copolymers 
thereof or polyvinyl alcohols. 
The dyes according to the invention are virtually insensitive to carriers 
and impart to the materials mentioned, in particular to polyester 
material, level yellow to violet colour shades of very good fastness 
properties in use, such as, in particular, good fastness to light, 
thermofixing, pleating, chlorine and wet processing, such as fastness to 
water, perspiration and washing; the dyeings are also characterized by 
good pH stability and very good fastness to rubbing. Additionally, very 
deep dyeings are achieved. The good fastness to sublimation and the good 
fastness to thermo-fixing of the resulting dyeings should be singled out 
particularly. 
The dyes according to the invention can also be used satisfactorily 
together with other dyes for the production of mixed shades. It is also 
possible, of course, to use mixtures of the dyes according to the 
invention with one another or mixtures of the dyes according to the 
invention with other disperse dyes. 
The abovementioned use of the azo compounds, according to the invention, of 
the formula (1) also forms a subject of the present invention, as does a 
process for dyeing or printing semi-synthetic or synthetic, hydrophobic 
fibre material, in particular textile material, which consists in applying 
one or more compounds of the formula (1) to the material mentioned or 
incorporating them into this material. The hydrophobic fibre material 
mentioned is preferably textile polyester material. Further substrates 
which can be treated by the process according to the invention and 
preferred process conditions can be found above in the more detailed 
explanation of the use of the compounds according to the invention. 
The invention also relates to the hydrophobic fibre material, preferably 
polyester textile material, which has been dyed or printed by the process 
mentioned.

The following examples illustrate the invention further, without limiting 
it thereto. Parts and percentages are by weight, unless stated otherwise. 
EXAMPLE 1 
1.73 g of 2-chloro-4-nitroaniline are suspended in 12.5 ml of water 
together with 4.4 ml of concentrated hydrochloric acid and approx. 0.05 g 
of a nonionic dispersing agent. The suspension is cooled to 0.degree. to 
5.degree. C. and 2.6 ml of 4N sodium nitrite solution are added dropwise. 
The mixture is stirred for a further hour at 0.degree. to 5.degree. C. and 
is filtered and excess nitrite is destroyed by means of sulfamic acid. The 
diazonium salt solution thus obtained is added dropwise, in the course of 
1 hour and at 0.degree. to 5.degree. C., to a solution of 3.45 g of 
N-ethyl-N-2(4-phenylazophenoxy)-ethylaniline in 200 ml of glacial acetic 
acid. The mixture is then stirred for a further 2 hours at 0.degree. to 
5.degree. C., 200 ml of icewater are added dropwise and 20 g of sodium 
acetate are added, whereupon the dye of the formula 
##STR7## 
is precipitated. 
The mixture is stirred for a further half hour at room temperature and is 
filtered and the residue is washed with water and a little methanol and is 
dried at 50.degree. C. in vacuo. 
The yield is approx. 83% of theory. The resulting dye dyes polyester fabric 
in red shades having very good fastness properties, in particular very 
good fastness to sublimation and thermal migration. 
EXAMPLE 2 
2.1 g of dichloro-2-aminobenzothiazol are dissolved at room temperature in 
a mixture of 20 ml of glacial acetic acid and 10 ml of propionic acid. 3.5 
g of 40% nitrosylsulfuric acid are added dropwise at 0.degree. to 
5.degree. C. and the mixture is stirred for a further hour. The diazonium 
salt solution thus obtained is added dropwise, in the course of 1 hour and 
at 0.degree. to 5.degree. C., to a solution of 3.45 g of 
N-ethyl-N-2-(4-phenylazophenoxy)-ethylaniline in 100 ml of 
dimethyl-formamide. The mixture is then stirred for a further 2 hours at 
0.degree. to 5.degree. C., 75 ml of water are added dropwise and the 
mixture is stirred at room temperature for half an hour. The resulting dye 
of the formula 
##STR8## 
is filtered off with suction, washed with water and a little methanol and 
dried at 50.degree. C. in vacuo. The yield is approx. 78% of theory. The 
resulting dye dyes polyester fabric in red shades having very good 
fastness properties, in particular very good fastness to sublimation and 
thermal migration. 
EXAMPLES 3-106 
The following dyes are prepared analogously to the procedure of Examples 1 
and 2. They dye polyester fabric in the shades indicated and with good 
fastness properties. 
3 
Example Dye Shade on polyester 
3 
##STR9## 
red 
4 
##STR10## 
red 
5 
##STR11## 
scarlet-red 
6 
##STR12## 
bordeaux 
7 
##STR13## 
red 
8 
##STR14## 
orange 
9 
##STR15## 
red 
10 
##STR16## 
red 
11 
##STR17## 
red 
12 
##STR18## 
orange 
13 
##STR19## 
scarlet 
14 
##STR20## 
red 
15 
##STR21## 
red 
16 
##STR22## 
red 
17 
##STR23## 
ruby 
18 
##STR24## 
red 
19 
##STR25## 
red 
20 
##STR26## 
red 
21 
##STR27## 
red 
22 
##STR28## 
scarlet 
23 
##STR29## 
scarlet 
24 
##STR30## 
red 
25 
##STR31## 
rub 
26 
##STR32## 
red 
27 
##STR33## 
scarlet 
28 
##STR34## 
violet 
29 
##STR35## 
rub 
30 
##STR36## 
violet 
31 
##STR37## 
blue 
32 
##STR38## 
ruby 
33 
##STR39## 
violet 
34 
##STR40## 
brown 
35 
##STR41## 
violet 
36 
##STR42## 
orange 
37 
##STR43## 
violet 
38 
##STR44## 
orange 
39 
##STR45## 
orange 
40 
##STR46## 
orange 
41 
##STR47## 
red 
42 
##STR48## 
yellow 
43 
##STR49## 
orange 
44 
##STR50## 
red 
45 
##STR51## 
red 
46 
##STR52## 
violet 
47 
##STR53## 
ruby 
48 
##STR54## 
red 
49 
##STR55## 
ruby 
50 
##STR56## 
red 
51 
##STR57## 
orange 
52 
##STR58## 
ruby 
53 
##STR59## 
ruby 
54 
##STR60## 
yellow 
55 
##STR61## 
orange 
56 
##STR62## 
golden-yellow 
57 
##STR63## 
ruby 
58 
##STR64## 
yellow 
59 
##STR65## 
red 
60 
##STR66## 
yellow 
61 
##STR67## 
red 
62 
##STR68## 
golden-yellow 
63 
##STR69## 
ruby 
64 
##STR70## 
yellow 
65 
##STR71## 
scarlet 
66 
##STR72## 
golden-yellow 
67 
##STR73## 
ruby 
68 
##STR74## 
yellow 
69 
##STR75## 
scarlet 
70 
##STR76## 
yellow 
71 
##STR77## 
ruby 
72 
##STR78## 
yellow 
73 
##STR79## 
red 
74 
##STR80## 
orange 
75 
##STR81## 
ruby 
76 
##STR82## 
yellow 
77 
##STR83## 
violet 
78 
##STR84## 
orange 
79 
##STR85## 
violet 
80 
##STR86## 
yellow 
81 
##STR87## 
orange 
82 
##STR88## 
orange 
83 
##STR89## 
red 
84 
##STR90## 
orange 
85 
##STR91## 
ruby 
86 
##STR92## 
red 
87 
##STR93## 
scarlet 
88 
##STR94## 
violet 
89 
##STR95## 
ruby 
90 
##STR96## 
red 
91 
##STR97## 
red 
92 
##STR98## 
red 
93 
##STR99## 
violet 
94 
##STR100## 
violet 
95 
##STR101## 
violet 
96 
##STR102## 
ruby 
97 
##STR103## 
violet 
98 
##STR104## 
red 
99 
##STR105## 
ruby 
100 
##STR106## 
ruby 
101 
##STR107## 
red 
102 
##STR108## 
red 
103 
##STR109## 
red 
104 
##STR110## 
blue 
105 
##STR111## 
red 
106 
##STR112## 
red 
EXAMPLE 107 
19.8 g of 4-hydroxyazobenzene are dissolved in 100 ml of diethylene glycol 
monoethyl ether, and 12.8 g of sodium carbonate and 52.5 ml of 
1,2-dibromoethane are added. The mixture is heated to approx. 116.degree. 
C. and is stirred for 2 hours at this temperature. The excess 
dibromoethane is then removed by steam distillation, and the water is 
subsequently removed by vacuum distillation at approx. 110.degree. C. This 
gives a suspension containing approx. 26 g of an orange-red powder of the 
formula 
##STR113## 
10.8 g of sodium carbonate and 11.3 ml of N-ethylaniline are added to this 
suspension, and the mixture is heated to 120.degree. to 125.degree. C. and 
is stirred for 12 hours at this temperature. The excess of N-ethylaniline 
is then removed by steam distillation. The reaction mixture is cooled to 
room temperature, whereupon a pale brown, viscous oil separates out. The 
water is decanted off, the oil is dissolved in acetone and the slight 
insoluble residue is removed by filtration. Ice and water are then added 
to the filtrate, and the precipitate which is deposited is filtered off 
with suction and washed with water. This gives approx. 23 g of a 
golden-yellow powder of the formula 
##STR114## 
having a melting point of 80.degree.-82.degree. C. 
EXAMPLES 108-113 
The following compounds can be prepared analogously to the method described 
in Example 107. 
##STR115## 
EXAMPLE 114 
5 parts of the dye obtained in Example 1 are mixed with 10 parts of a 
dispersing agent of low salt content (of the dinaphthylmethanesulfonic 
acid type), and the mixture is ground in 85 parts of water in a microsol 
mill using 300 parts of glass spheres of diameter 0.5 mm. 
4 parts of polyester fabric (Diolen) are dyed for one hour at 130.degree. 
in 100 parts of a dye liquor adjusted to pH 4 and containing 0.2 part of 
above dispersion and 0.05 part of a wetting agent (for example fatty acid 
methyl-tauride) and 0.05 part of a dispersing agent (for example an agent 
based on dinaphthylmethanesulfonate). A red dyeing having very good 
fastness to light is obtained. The dyeing is also distinguished by 
excellent fastness to sublimation and thermofixing. 
EXAMPLE 115 
A polyethylene glycol terephthalate fabric is impregnated on a padder at 
40.degree. with a liquor of the following composition: 
20 parts of the dye preparation obtained in Example 114, finely dispersed 
in 
10 parts of sodium alginate, 
20 parts of nonionic wetting agent and 
930 parts of water. 
The fabric is squeezed out to approx. 60%, dried at 100.degree. and then 
fixed for 60 seconds at a temperature of 210.degree.. The dyed goods are 
rinsed with water, soaped or purified by reduction and dried. This gives a 
brilliant, light-fast, red dyeing which is distinguished, in particular, 
by good fastness to thermal migration.