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Патент USA US2118661

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2,118,531
Patented May 24, 1938
UNITED STATES
PATENT OFFICE
2,118,661
AZO DYES AND‘ PROCESS FOR MANUFAC
TUBING THE SAME.
Erich Baumann, Dessau-Ziebigk, Germany, as
signor to General Aniline Works, Inc., New
York, N. Y., a corporation of Delaware
No Drawing. Application March 12, 1936, Serial
No. 68,451. Renewed October 22, 1937. In
Germany March 13, 1935
5 Claims.
(Cl. 260-96)
My present invention relates to the manufac
ture of azo dyes which are applicable for dyeing
tated by means of sodium acetate after complete
coupling, dyes acetate silk fast blue red tints.
cellulose esters, especially acetate silk, by cou
By using 26 parts of 3-bromo-1-di-(hydroxy
pling a diazo compound from an amino compound
ethyD-am‘mobenzene there is obtained a dye
which dyes acetate silk similar tints.
5,. of the general formula
5.
Example 4.—-A diazo solution is prepared by
stirring at 25 to 30° C. 20.7 parts of 2,6-dichloro- 1
1-amino-4 -nitrobenzene into nitrosyl-sulfuric
acid, made by introducing 7 parts of sodium ni
trite into 130 parts of concentrated sulfuric acid, 10
10
in which X and Y represent hydrogen or halo
gen, with a di-(hydroxyalkyl) -aniline which con
tains halogen in the 3-position.
Further objects of my invention are the new
15 dyes obtainable according to this process.
The new dyes have good capacity for white dis“
charge and good fastness to washing and water,
and also very good fastness to light.
The following examples illustrate the inven
20
tion, the parts being by weight:-—
Example 1.—-A diazo solution prepared in the
usual manner from 13.8 parts of 4~nitro-1-ami
nobenzene is caused to flow into a cold solution
of 21.6 parts of 3-chloro-l-di-(hydroxy-ethyl)
25 aminobenzene in 25 parts of hydrochloric acid of
23° Bé. and 800 parts of water. The reaction is
buffered by means of sodium acetate until the
end of the coupling. The dye thus obtained yields
on acetate silk a fiery, clear scarlet of very good
30 fastness to light.
If, instead of the 3-chloro-1-di-(hydroxy
ethyl) -aminobenzene
the
3 - bromo-l-di - (hy—
droXy-ethyD-aminobenzene is used, there is ob
tained a dye which also dyes acetate silk clear
35 fast scarlet tints.
Example 2.-A diazo solution from 17.3 parts
of 4-nitro-2-chloro-l-aminobenezene, obtained
in the usual manner, is caused to flow into a cold
solution of 21.6 parts of 3-chloro-1-di-(hydroxy—
40 ethyl) -aminobenzene in 25 parts of hydrochloric
acid of 23° Bé. and 800 parts of water, and the
reaction is buffered with sodium acetate until
coupling is complete. The precipitated dye yields
on acetate silk bluish-red tints of good general
45 fastness and excellent fastness to light.
By using 3-bromo-1-di-(hydroxy-ethyl)-ami
nobenzene instead of the 3-chloro-1-di- (hydroxy
ethyl) -aminobenzene there is obtained a dye
which also dyes acetate silk fast red tints.
Example! 3.-A diazo solution made in the usual
50
manner from 21.7 parts of 4-nitro-2~bromo—1
aminobenzene is introduced into a cold solution
of 21.6 parts of S-chloro-l-di-(hydroxy-ethyl)~
aminobenzene in 25 parts of hydrochloric acid of
55 23° Bé. and 800 parts of water. The dye precipi~
and the mass is then diluted by pouring it upon
ice. The ?ltered solution of the diazo compound
in sulfuric acid is run into a cold solution of 21.6
parts of 3-chloro~1-di-(hydroxy-ethyl) -amino
benzene in 25 parts of hydrochloric acid of 23° 15
Bé. and 1000 parts of water.
The mixture is
thereupon buffered with sufficient sodium hy
droxide until the coupling is at an end. The dye
dyes acetate silk full yellow-brown tints fast to
light.
If
3-bromo-l-di-(hydroxy-ethyl) -aminoben
20
zene be substituted for the 3-chloro-1-di-(hy
droXy-ethyl) -amino benzene a dye is obtained
which dyes acetate silk similar but somewhat
more yellow tints.
25
Example 5.—A diazo solution prepared by in
troducing 29.6 parts of 2,6-dibromo-1-amino-4
nitro-benzene into 130 parts of concentrated sul
furic acid and '7 parts of sodium nitrite at 25 to
30° C. and pouring the mass upon ice is intro
duced into a solution of 21.6 parts of 3-chloro-1
di-(hydroxy-ethyl) -aminobenzene in 25 parts of
hydrochloric acid of 23° Bé. and 1000 parts of
water and, at the end of the coupling, the mix
ture is buffered with sodium hydroxide. The dye 35
dyes acetate silk fast yellow-brown tints.
By using 26 parts of 3—bromo—1-di(hydroxy
ethyDaminobenzene there is obtained a dye
which dyes acetate silk similar tints.
What I claim is:—
40
1. The dyes which correspond to the general
formula
X
CH2.CH2.0H
/
45
CH2.CH2.0H
Y
Z
wherein X and Y is an element selected from the
group consisting of hydrogen and halogen, and Z
is a halogen of the group consisting of chlorine
and bromine, said dyes dyeing acetate silk clear
red to yellow-brown tints of good fastness to
washing and water and of a very good fastness
to light, the dyeings having a good capacity for
White discharge.
55
2
2,118,661
2. The dyes which correspond to the formula
CHz.OHz_.OH
5
vwhere Z is a halogen of the group consisting of
chlorine and bromine, said dyes dyeing acetate
silk a ?ery, clear scarlet of very good fastness
wherein Z is a halogen selected from the group
consisting of chlorine and bromine, said dyes
dyeing acetate silk full yellow-brown tints fast
to light.
5. The process which comprises diazotizing an
amine of the general formula
X
/
OzNQNH:
10 to light.
3. The dyes which correspond to the formula
C1
/
CHLCHLOH
/
15
Z
wherein X and Y stand for an element selected
G H1. C H1. 0 H
wherein Z means a halogen of the group consist
from the group consisting of hydrogen and halo
gen, and coupling the diazo compound with an 15
amine of the general formula
ing of chlorine and bromine, said dyes dyeing
acetate silk bluish-red tints of good general fast
20 ness and excellent fastness to light.
4. The dyes which correspond to the general
formula
C]
OaN
/
N
\
N:
01
10
Y
Z
GHI-GHZ-OH
CHI-CHLOE
Z
\
omomon
wherein Z is a halongen selected from the group
consisting of chlorine and bromine.
ERICH BAUMANN.
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