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Патент USA US2113151

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Patented Apr. 5, 1938
I‘ 2,113,151
UNITED STATES PATENT OFFICE
2,113,151
I
> ,MONOAZO-DYESTUFFS
Richard Fleischhauer, Frankfort-on-the-Main
Fechenheim, Germany, assignor to General
Aniline Works, Inc._, New York, N. Y., a cor
poration of Delaware
No Drawing. Application December-‘1, 1936, Se
rial No. 113,611. In Germany'December 2,
1935
4 Claims.
(Cl. 260-92)‘
My present invention relates to monoazo dye
stuffs, more particularly to those of the general
formula
has been ?nished‘l'it is isolated and dried. The
new dyestu? of the formula
.
l
l
‘
OH 'rlniooonl '
0H NHOOCHa
10
v15
15
wherein R stands for a member of the group con
sisting of hydrogen and an alkyl group contain
ing at the most 3 carbon atoms and one X means
hydrogen and the other a sulfonicacid group.
The new dyestuffs are obtained by combining
diazo compounds of aromatic amines of the for
mula
CHsCO
.
\
/ C
' N
p
NE:
is a dark red water soluble powder and dyes wool
bright bluish red shades and exhibits an excellent
levelling power.
»
»
.
Example 2
When using’ as a diazo component the diazo
compound of 20.6 parts of 1%acety1-isobutylam
ino) -4-aminobenzene and carrying out the reac~
tion otherwise as described in Example 1 the
formed dyestuff of the formula
(l)H NHCO CH:
wherein R has the aforesaid signi?cation, with
1-acetylamino-8-naphthol-3,6- or -4,6-disulfonic
acid.
30
The new dyestu?s dye the animal ?bres bluish
HOaS/
\SOaH
red shades of an unusual fastness to sea-‘water
and are distinguished in comparison with anal
ogous dyestuffs by an excellent levelling power.
In order to further illustrate my invention the
following examples are given, the parts being by
weight and all temperatures in degress centi
grade. However, I wish it to be understood that
my invention is not limited to the particular
products nor reaction conditions mentioned
therein.
Example 1
17.8 parts of l-(acetyl-ethyl-amino) ~4-amino
benzene are diazotized in the usual manner in an
aqueous medium. The diazo solution thus ob
tained is added while cooling to a solution con
taining an excess of sodium carbonate and 37
parts of 1 -acetylamino- 8 -naphthol-3,6-disul
ionic acid. When the formation of the dyestuff
CH3
is when dry a bluish red water soluble powder and 40
dyes wool bright bluish red shades and exhibits
an excellent levelling power.
Similar dyestuffs are obtained when starting
from the diazo compound of l-[acetyl-n-propyl
45
(and n-butyl) -amino] -4=-amino-benzene.
' Example 3
16.4 parts of 1-(acetyl-methyl-amino) -4-am
ino-benzene are diazotized in the usual manner in 50
2
2,113,151
an aqueous medium. The diazo solution thus ob
tained is added while cooling to a solution con
2. The monoazo dyestuff of the formula
taining an excess of sodium carbonate and 37
OH ITIHOOCH:
parts of 1-acety1-amino-8-naphthol-4,6-disul
fonic acid. When the formation of the dyestu?
has been ?nished it is isolated and dried. The
new dyestu?z' of the formula
$1
0H NHCOCH:
10
1O
which dyestuif is a dark red water soluble powder
and dyes wool bright bluish red shades and ex
hibits an excellent levelling power.
3. The monoazo dyestu? of the formula
OH NHOOCHa
is a red water soluble powder and dyes wool
bright red shades and exhibits an excellent lev
elling power.
Similar dyestuffs are obtained when starting
from the other diazo compounds, aslmentioned in
the foregoing examples.
I claim:
1. Monoazo dyestuffs of the general formula
30
OH NHCOCH:
>
CH3
30
CH3
which dyestuff is when dry 1-). bluish red water
soluble powder and dyes wool bright bluish red
shades and exhibits an excellent levelling power.
4. The monoazo dyestuff of the formula
OH NHCOOH:
40
wherein R stands for a member of the group con
sisting of hydrogen and an alkyl group contain
ing at the most 3 carbon atoms and one X means
hydrogen and the other a sulfonic acid group,
which dyestuffs dye the animal fibres bluish red
shades of an unusual .fastness to sea-water and
are distinguished in comparison with analogous
dyestuffs by an excellent levelling power.
which dyestu? is when dry a red water soluble
powder and dyes wool bright red shades and ex
hibits an excellent levelling power.
RICHARD FLEISCHHAUER.
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