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Патент USA US2052477

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Patented Aug. 25, 1936
2,052,477
UNITED STATES PATENT OFFICE
2,052,477
AZO-DYESTUFFS AND THEIR
MANUFACTURE
Adolf Krebser, Riehen, near Basel, Switzerland,
asslgnor to the ?rm J. It. Geigy A. G., Basel,
Switzerland
No Drawing. Application October 16, 1935, Serial
No. 45,358. In Switzerland November 5, 1934
12 Claims. (Cl. 260-97)
This invention consists in the manufacture of
.3. A process for the manufacture of azo-dye
new valuable monoazo-dyestu?s capable of be
ing chromed by coupling the diazo-compound stuffs, consisting in coupling diazotized @l-nitro
from 4-nitro-2-amino-phenol-G-sulphonic acid
CR with a phenol containing in para-position an
alkyl-group with at least 3 and at most 5 carbon
atoms.
'
_
The new dyestuffs are dark powders and dye
wool in an acid bath yellow-brown tints. When
1 O chromed these tints change to a valuable full
brown with excellent properties of fastness. The
dyestuffs may also be converted into the chro
mium complex before their application in the dye
ing process.
The following examples illustrate the inven
tion:
Example 1
23.4. kilos of 4-nitro-2-aminophenol-6-sul
20 phonic acid are diazotized by the usual method.
The excess of mineral acid is buffered by means
of sodium bicarbonate and the diazonium solu
tion is added, while stirring, to a solution of 16.5
kilos of para-tertiary-amyl-phenol in 6 kilos of
caustic potash lye of 100 per cent strength and
50 litres of water. When coupling is complete
the dyestuff is salted out, ?ltered and dried. The
formation of the dyestuif can be facilitated by
the presence of pyridine.
The dyestu?‘ is a brown powder soluble in water
and in concentrated sulphuric acid to yellow
brown solutions.
If in this example para-tertiary-amyl-ortho
cresol is used as coupling component, a dyestuif
F
with similar properties is obtained.
Ewample 2
For the quantity of para-tertiary-amyl-phenol
used for coupling in Example 1 there is substi
tuted 13.5 kilos of para-iso- or normal-propyl
phenol or 15 kilos of para-tertiary-butyl-phenol,
or para-isobutyl-ortho-cresol, the quantity of the
2-aminophenol-S-sulphonic acid with a mono
cyclic phenol containing as a substituent in para
position an alkyl-group with 3 carbon atoms.
4. A process for the manufacture of azo-dye
stu?s, consisting in coupling diazotized 4-nitr0
Z-aminophenol-G-sulphonic acid with a mono
cyclic phenol containing as a substituent in para
position an alkyl-group with 4 carbon atoms.
5. A process for the manufacture of azo-dye
stuifs, consisting in coupling diazotized ll-nitro
Z-aminophenol-?-sulphonic acid with a mono
cyclic phenol containing as a substituent in para
position an alkyl-group with 5 carbon atoms.
15
6. A process for the manufacture of azo-dye
stuifs, consisting in coupling diazotized 4-nitro
2-aminophenol-6-sulphonic acid in the presence
of pyridine with a monocyclic phenol contain
ing as a substituent in para-position an alkyl- 20
group with 3 carbon atoms.
7. A process for the manufacture of azo-dye
stuifs, consisting in coupling diazotized 4-nitro
Z-aminophenol-G-sulphonic acid in the presence
of pyridine with a monocyclic phenol containing 25
as a substituent in para-position an alkyl-group
with 4 carbon atoms.
8. A process for the manufacture of azo-dye
stu?‘s, consisting in coupling diazotized 4-nitro
Z-aminophenol-S-sulphonic acid in the presence 30
of pyridine with a monocyclic phenol containing
as a substituent in para-position an alkyl-group
with 5 carbon atoms.
q
9. A process for the manufacture of an em
dyestuif, consisting in coupling diazotized 4 35
nitro-2-aminophenol-6-sulphonic acid with para
tertiary-amyl-phenol.
10. A process for the manufacture of an azo
dyestu?, consisting in coupling diazotized 4
nitro-2-aminophenol-G-sulphonic
acid
with
para-isobutyl-o-cresol.
40
,
diazonium solution being the same as prescribed
11. A process for the manufacture of an azo
in Example 1; there are obtained brown chrome
dyestuffs with similar excellent properties of
45 fastness.
dyestuif, consisting in coupling diazotized 4
What I claim is:1. A process for the manufacture of azo-dye
10
nitro-Z-aminophenol-6-sulphonic acid with
gara-isobutyl-o-cresol
in the presence of pyri
me.
45
12. Azo-dyestuifs from diazotized 4-nitro-2
stuffs, consisting in coupling diazotized 4-nitro
aminophenol-G-sulphonic acid and a monocyclic
2-aminophenol-6-sulphonic acid with a mono
cycle phenol containing as a substituent in para
phenol containing as a substituent in para-posi
tion an alkyl-group with at least 3 and at most 50
position an alkyl-group with at least 3 and at
most 5 carbon atoms.
2. A process for the manufacture of azo-dye
5 carbon atoms, said dyestuffs being soluble in
water and in concentrated sulphuric acid to yel
low-brown solutions and dyeing wool in an acid
bath yellow-brown tints which when chromed be
stuffs, consisting in coupling diazotized 4-nitro
Z-aminophenol-?-sulphonic acid in the presence
of pyridine with a monocyclic phenol containing
as a substituent in para-position an alkyl-group
with at least 3 and at most 5 carbon atoms.
come a valuable full brown of excellent properties
of fastness.
ADOLF ICREBSER.
55
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