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Патент USA US2123748

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Patented July 12, 1938
2,123,748‘
UNITED STATES PATEN‘r‘i'o‘TFFicE
METALLIFEROUS NITRO-AZO-DYESTUFFS
Hans Schindhelm, Frankfort-on-the-Main-Fech
enheim, Germany, assignor to General Aniline
Works, Inc., New York, N. Y., a corporation of
Delaware
No Drawing. Application November 2, 1935, Se
rial No. 48,057. In Germany November 6,
1934
1 Claim.
(Cl. 260—12)
This invention relates to new metalliferous
Example‘ 1
13.8 parts‘ of p-nitraniline are diazotized in the
nitro-azo-dyestu?s, more particularly to copper
compounds of dyestuffs corresponding to the gen
eral formula:
ususal manner with 35 parts of hydrochloric acid
(d=1.15) and 6.9 parts of sodium nitrite. The
diazo solution is then allowed to flow at 0° into
a solution of 28.9 parts ofv the sodium salt of
‘ l-amino--2-ethoxynaphthalene - 6 - sulfonic
mixed with a solution of sodium acetate.
acid
Then
the mass is heated to' 70° and rendered alkaline 1
by the addition of sodium carbonate.
The pre
cipitated dyestuff is- isolated by ?ltration and
freed from the adhering mother lye by washing
wherein R means the radical of a diazotization
15a component of one of the groups consisting of
compounds of the benzene and naphthalene series,
X-stands for one of the groups consisting of hy
drogen and a sulfonic acid group and ‘Y stands
for one of the group consisting of an acyl radical
20‘; and a radical of the benzene series.
These dyestuffs are obtainable by diazotizing
a nitro-diazo compound, combining- it with a
l-amino - 2 - naphthol — ether, diazotizing again,
combining with an N-derivative of 2-amino-5
25 hydroxy-naphthalene-7-sulfonic acid and ?nally
it with salt water. Then the paste is dissolved
in 2000 liters of water and again diazotized by
means of 7 parts of sodium nitrite and 35 parts
of hydrochloric acid (d=1.15). When the diaz
otation is ?nished the mass is combined in the
usual manner, while stirring, with a solution of
41 parts of the sodium salt of 2-benzoylamino-5
naphthol-‘I-sulfonic acid. When the formation of
the nitro-azodyestuff is ?nished, the mass is
heated, the dyestu?’ is precipitated by the addi
tion of common salt, and isolated by ?ltration and
Washed.
It corresponds to the formula: '
\
S 0311
V
0-02115
so;
om-O-n:
'
I
NH~CO®
N=N
'
,
on
SOaH
’
'
>
35 treating‘ the dyestu? with agents delivering cop- .
The paste is then dissolved in Water and the
solution is heated to boiling, while stirring, for
As ?rst components may be used for instance:_ some hours with 35, parts of crystallized copper
nitranilines, nitrotoluidines, nitro - anisidines, sulfate in presence of acetic acid. Thereafter
nitro-chloroanilines, nitr'aniline-sulfonic acid, the product is isolated by ?ltration, washed with
40 nitro - naphthylamine-sulfonic-acids, nitrophen
water, then made to a paste with sodium car
yl-azo-amino-naphthalene sulfonic acids.
‘bonate and water and again isolated therefrom.‘
As middle components may be used: the alkyl
The new dyestuff represents when dry a dark
ethers of 1-amino~2-hydroxy-naphthalene or powder soluble in water with a greenish-grey, and
their sulfonic acids.
in concentrated sulfuric acid with a green color,
45
As third component may be used for instance: and dyes cotton greenish-grey shades of an ex
45
2-acetylamino-, 2-benzoylamino-, 2-phenylami
cellent fastness to light.
per.
_
.
-
no-, 1,2 - imidazolyl - 5 - hydroxy-naphthalene-7
sulfonic acids.
The new metalliferous nitro-azo-dyestu?s dye.
50 the ?bers, especially vegetable ?bers, grey shades
Example 2
A diazo compound prepared in the same man
ner from 13.8 parts of m-nitraniline is allowed
to run into a solution of 28.9 parts of the sodium 50
of a good fastness. They exhibit a pecular fast
ness to light and surpass thereby the analogous 'salt of l-amino-2-ethoxynaphthalene-6-sulfonic
dyestuffs hitherto known, but containing no nitro acid, mixed with a solution of sodium acetate.
group.
The combination to the amino-azo-dyestu?' is in
55
In order to further illustrate my invention the stantly ?nished. The mass is ?ltered and the
following examples are given, the parts being by ?ltrate is washed with a little quantity of water.
weight and all temperatures in centigrade degrees,
but it is to be understood, that my invention is
not limitedto the particular products nor re
60 acting conditions mentioned therein.
The paste is then mixedi'with .ice and trans
formed into- the diazo-‘azo-compound by means
of 35 parts of hydrochloric acid and 6.9 parts of
sodium nitrite. The reaction product is poured
n ..
2,123,748
2i
acetic acid. The dyestu? corresponds to the for
into a solution of 40 parts of the sodium salt of
2 - m - carboxyphenylamino - 5 - naphthol - 7 -
mula:
‘
.
S OaH
0~G1H5
S 0:11
.
.
1
,
.
NH—C 0O
.
—N=N
OIN
p
'
N=N
‘
‘
H
w
10
10
SO3H
sulfonic acid mixed with pyridine. The dyestu?
precipitated by the addition of common salt is
isolated by ?ltration and washed. It corresponds
15 to the formula:
After the addition of a solution of 35 parts of
crystallized. copper’ sulfate the reaction product
is boiledvfor some hours, while stirring under a
re?ux ‘condenser. Then the dyestuff is isolated 15
o-ozm sonar
QN:
——~N=N
OOH-
'
by ?ltration, washed, made to a paste with so
20
dium carbonate and dried. The dark powder
thus obtained dissolves in waterwith a greenish
grey, in concentrated sulfuric acid with a green
S 0311
Thereafter the dyestu? paste is dissolved in water color and dyes cotton greenish-grey shades of an
excellent fastness to light.
25. and transformed into the cupriferous compound‘
‘by heating it for some hours to‘ boiling. under a
Emample 4
011
re?ux condenser, while stirring in anacetic acid
medium with 35. parts of crystallized copper
16.8 parts of 5-nitro-2-amino-anisole are mixed
with 36 parts of hydrochloric acid (d=1.15) ,luntil
sulfate. The mass is ?ltered, the ?ltrate washed ' the whole base is transformed-into the chloro-~
30 with cold water and thereby freed from the ad
hydrate, and the pasteris 'diazotized with 6.9.
'4 hering excess of copper sulfate. Then the paste
parts of sodium nitrite. Thdudiazo-solution is
is mixed with a diluted soda lye and dried.
The dyestuif represents a black powder, which coupled ‘as described‘in Example 1 with the so
dium salt of 1—amino-2-ethoxy-naphthalene-6
dissolves in Water with a greenish-grey, in con
sulfonic
acid, and the intermediate compound? is
35 centrated sulfuric acid with a green color and isolated. The dyestu?' is further diazotized with
“dyes cotton greenish-grey shades of an‘extraor
dinary fastness to light.’
Example 3'
H
29 parts; of the sodium salt of 6.-nitroe2-amino-'_
40
,‘iq. naphthalene-B-sulfonic acid are diazotized with
35 partsof hydrochloric acid and 6.9 parts of the
35 parts of concentratedv hydrochloric acid and
7 parts‘of sodium nitrite‘ and coupled witlra
solution of the sodium salt of Z-‘(m-carboxy
phenylamino) -5-naph'thol-7-sulfonic ' acid" con
taining pyridine. The dyestu?, corresponding to
the formula:
SOaH
.
. OCH»
...\
>
'
Hols
NHQ
N=N
COOH
is isolated inthe usual manner and mixed with. 505
After the addition of‘aceti'cv acid‘and‘a'
solution of 35.parts of. crystallized copper sulfate‘
in a little quantity'of ‘Water, thejmixture is .boiled
thalene-?esulfonic acid. After some minutes the forsome hours while stirring und’erv a re?ux‘com
denser. Then the dyestu? is isolated by' filtrae
55 copulation, is ?nished and the. formed dyestu? is. tion, washed and dried: The .black‘powder" di‘s-.
__ isolated by ?ltration.
v
_ .
Then the aminoazo-dyestu?is diazotized with solves in water to a blue,'in concentratedsulfuric'
acid to a greyish-bluesolution and dyes cotton
6.9 parts of sodium nitrite and 35 parts of hydro
50 sodium salt of nitrous acid.
This‘ diazo com
pound‘is combined in- the usual manner, while
stirring, with an aqueous solution of 28 parts
of the sodium salt of l-amino-2-ethoxy-naph
water.
grey shades of an excellent fastness to light.
'
chloric acid (d=1.15).. The. excess of hydro
I claim:
‘
60 chloric acid isneutralized by the addition of sodi
The copper compound of the dyestu? ' corre
_ ‘um acetate and the diazo. compound is coupled
with a solution of 36 parts of ‘the sodium salt‘ of '
sponding to the formula:.
SOaH
\
65
"
\\
70
-
con
/
\Cu/
which compound represents a, blacks-powder SO19";
When the copulationhis, ?nished-,.the dyestu?lisu uble-in. water to arblue, in‘ ‘concentrated sulfuric,v
precipitated by the addition-‘of common-salt. acid to a-greyish blue'solution, dyeing cotton grey"
‘ 2ebenzoylamino-5-naphthol-Y7-s u 1 Toni 0 acid.
The massis ?lteredand-the ?ltrate->is--washed,.
dissolved in >water and acidi?ed by meanszof
shades‘ of an excellentfastness to light“ -,- "
Y.
, HANS SCHINDI-IEIM;
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