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Патент USA US2117731

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Patented May 17, 1938
2,117,731
UNITED STATES PATENT ‘OFFICE,
2,117,731
AZODYESTUFFS
Theodor Kollmann, Leverkusen, and ‘Eugen
Glietenberg, Leverkusen-I. G.-Werk, Germany,
assignors to General Aniline Works, Inc., New
York, N. Y., a corporation oi’ Delaware
No Drawing. Application November 11, 1936,
Serial No. 110,278. In Germany December 18,
1935
13 Claims.
(C1. 8—-6)
The present invention relates to water insoluble
azo dyestuffs and to printing preparations suitable for the manufacture of the said dyestuffs
by a printing process, more particularly our in-
cyclic bases or cyanamide or cyanamide car
boxylic acid (compare U. S. Patents 1,858,623,
1,874,524, 1,867,088, 1,871,850, 1,879,424, 1,882,560,
1,882,562, 1,979,327, 1,982,681), and by develop
5 vention relates to water insoluble azo dyestuffs
ing the dyestu? in the customary manner, e. g.
which may be represented by the general
by hanging, steaming or treating with dilute acids
formula;
or steam containing an acid (compare U. S. Pat
R-—~N=N——R'-—N==N——R”
10
\X_Me_
'_
ents 1,880,522, 1,882,556, 1,893,991, 2,035,518). In
this manner in general brown shades of good
fastness properties are obtained.
10
In the said formula R stands for an aromatic
According to a further feature of the invention
radical which may bear further azo groups, for for producing the new water insoluble azo dye
example for the radical of the benzene series, of stuffs by a printing process preparations consist
the naphthalene series, of the diphenyl series and mg of the above-named azo dyestuffs and aryl
15 the like, R’ stands for a radical of the benzene nitrosamines or aryldiazoamino- or -imino cornseries, capable of coupling twice. which is sub- pounds, soluble in water or an alkaline medium,
stituted in a position meta to Y by an amino or have proved particularly suited. (Compare U. s.
a hydroxy group, by the hydroxy group, how- Patents 1,882,561, 1,915,734).
ever, only when Y stands for NH, R.” stands for
The metal containing ortho-hydroxyazo dye
20 the radical of a diazotized aromatic amine of the stuffs used as starting materials can also be obkind generally used in the manufacture of ice tained from ortho-halogen amines or ortho
colors, X stands for an oxygen atom or the group alkoxy amines as diazotization components with
CO0, Y stands for an oxygen atom or the group replacement of the halogen or splitting up of the
NH, Me stands for a metallic atom, capable of alkoxy groups.
‘>15 yielding azo dyestu? complex compounds and
The invention is illustrated by the following
wherein the bridge X—-Me-Y is attached to the examples:
nuclei in positions ortho to the azo bridge, it being
Example 1
self understood that groups inducing solubility
A cotton tissue is printed with a printing color,
in water such as the sulfonic acid group and the containing in 1000 grams:
30 carboxylic acid group, are excluded as substitu28 grams of the diazoimino compound from
ents.
The process of an Eacture of the dyestuffs diazotized 4-chloro 2 anisidine and sarcosine,
according to the invention is by coupling ’ espe-
cially on the ?ber, metal complex compounds of
35 the azo dyestuffs from meta-aminophenol, metaphenylenediamine or the substitution products
thereof, capable of coupling twice, and ortho
hydr'oxy- or ortho-carboxydiazo compounds, the
azo dyestuffs containing no further solubilizing
40 groups, with diazo compounds suitable for the
manufacture of ice colors. The process may be
20
25
30
zgildalggdxlil?la'ammophenol coupled in an acetic 35
,
0
glnnllssogfagrigilsniggztiéfloiizggf8
Be"
500 grams ofya neutral Sgamh tljagwanth
thickener the remainder hem water
dri d t ’
f 51m
.g t
’
40
e ’ S gamed or
nutes in s 8am containing
acetic and mid formic acid’ rinsed’ soaped' again
ufacture of ice colors by impregnating the ?ber
lf'msed
dnedt Avery
fun’ deep brown or good
astnessand
properties
is obtained.
with the azo dyestuffs containing metal referred
15
gm‘ 15 ofdyestu?
the Copper
plex co I H d of
the32monoazo
from004-chloro-2-diazophe
effected in the manner generally used in the man-
45 to above and further developing the dyeing with
5
iofmh?lfeszu?o cozresponds to the following 45
.
_
u__
suitable diazo compounds.
A particular method of effecting the process is
by bringing the said coupling component on the
?ber together with an arylnitrosamine suitable
50 for the manufacture of ice colors (compare U. S.
P. 1,915,734) or a suitable aryldiazo-amino- or
-imino compound soluble in water or an alkaline
medium, as obtainable by the condensation of
diazo compounds with primary aliphatic or aro55 matic, secondary aliphatic aromatic or hetero-
N=NONHI
-
C1
|
N=N
50
b
1
1
OH‘
Instead of coupling the meta-aminophenol
dyestuff in an acid medium also an alkaline me
dium can be used.
55
2
2,117,731
' Example 2
Example 3
A cotton tissue is printed with a printing color
containing in 1000 grams:
28 grams of the diazoimino compound from
A cotton tissue is printed with a. printing color
containing in 1000 grams:
1
28 grams of the diazoimino compound from
42 grams of the copper complex compound of
31 grams of the copper complex compound of
the
the monoazodyestu? from 4-chlorodiazophen0l
10 and meta-phenylene diamine,
thickener, the remainder being water,
and developed as described in Example 1. A red
‘Y
The dyestu?' corresponds to the following
formula:
500 grams
O_cu_0
N:
’
NH,
1
'_
10
of , a neutral starch tragacanth
N=N
‘
'
4-chloro-2-diazo
thickener, the remainder being water,
and developed as described in Example 1. A deep
brown is obtained.
The dyestu? corresponds to the following 15
formula:
O-Gu-NH
,
from
38 grams of aqueous caustic soda lye 38° Bé.,
50 grams of glycolmonoethylether,
dish brown is thus obtained.
monoazodyestu?’
phenol and 4'-methy1~3-hydroxydiphenylamine,
I
500 grams of a neutral starch tragacanth
'15
5
diazotized 4-chloro-2-anisidine and sarcosine,
diazotized 4-chloro-2-anisidine and sarcosine,
01
NHOCH;
'
1
N=N
c1
N=N
'
CH1
CH:
'
_
In the following table there are given further
combinations prepared in accordance: with the
invention.
' 7 ‘.Oouplingqmiponent ‘
Diazotization component
o_._.cyu'_o -
35
‘I _,
v
Shade
O CH
\
/oH1
'
N,=N~®-N\
‘
30
'
35
NH;
CH:
Full reddish brown
*
l
40
O CH
Gal
l
_ N<
I‘
‘
40
NH1
Full reddish brown
CIHI
I
45
\
4
~
CHI
00
m
N=N—O—N<
'
1
.50
NH,
CHI
OCH
in
C333
N=
N H1
(3:35
0 OH.
CH:
N=N
N=N
65
NH;
CH:
H:
55
“
N<
O——Cu——0
Middle brown
l
0-—Gu-NH
I
50
'
N
1
60
Middle brown
l
O———Cu—-N H
55
45
'-
Middle brown >
l
O CH:
NH:
1
60
'NH:
Middl? bl‘OWI!
on '
O—Cu—0
65
\
N=NQNHQ
\’ u
GHQ-NH:
Middle brown
70
/0-_>—Cu—-\0
75
QN=N
1
.
70'
O ClHl
NH:
O-O O—NH
NH:
C231
Full black brown
75
2,117,781
Coupling component
Diawtiution component
0—0u—-NH
5 ' r
3
Shade
00H;
N=N
0H
NH,
Middle brown
GHQ-NH;
Middle brown
01
5
l
O—Cu-—-NH
\
10
N=N‘<:>-OH
1D
1
O———Cu—NH
15
/
00H
\
i
i
QN=NOOH
'
15
NH;
1
Middle brown
CH:
, ‘
o-ou_-NH
20
-
com.
\
2°
N=N~C>—OH
Q0 O—NH
NH,
1
25
C113:
o-cu_NH
00m
Q =N
,
Black brown
NH;
25
NH,‘
1
Middle brown
CH:
/
\
c
Q =NONH:
.3‘
CHiONH:
Middle brown
1
40
_
i
'
-
We claim:
7
1. Water insoluble azo dyestu?s of the general
formula:
R<—N=N——R’——-N=N—R”
45
X-Mo-Y
40
ever, by the hydroxy group only when Y stands
for NH, R" stands for the radical of a diazotized
aromatic amine generally used in the manufac—
ture of ice colors R, R’ and R" being free from
water solubilizing groups, X stands
for a mem,
wherein R stands for an aromatic radical’ R,
ber selected from the group consisting of an
stands for a radical of the benzene series capable
of coupling twice, which is substituted in a po_
oxygen atom and the group C00’ Y sitapds for a
member selected from the group consisting of an
sition meta to Y by a member of the group con-
50 Sisting of an amino and hydroxy group, however,
oxygen atom and the group NH’ melding when
by the hydroxy group only when Y stands for
gogd astnes.s propertles"
f
‘ “(alter Insoluble azo dyestuffs of the general
ormu 8"
0° water solubilizing groups, X stands for a mem-
‘
R
ber selected from the group consisting of an
oxygen atom and the group COO, Y stands for
a member selected from the group consisting of
an oxygen atom and the group NH Me stands
i
produfced on the ?ber ‘in general brown shades of 50
NH, R” stands for the radical of a diazotized
aromatic amine generally used in the manufacfr ture of ice colors,.R, R’ and R" being free from
,
4.)
N
_
,N
.N_N_R,,
_
'
x
55
O_Cu_NH
_
v
‘
,
jivherein R and R" stand for benzene radicals be
60 for a metallic atom capable of yielding azo dyestuff complex compounds, and wherein the bridge
X--Me--Y is attached to the nuclei in positions
ortho to the azo bridge, yielding when produced
mg ?ee from Water Solubilizing groups, x Stands 60
191' _?1 substltuent sjelected from the group con‘
818mg of the ammo 8mm) and the hyqroxy
groupi and wheremfhe bnfig}? O—Cu_'NH 15 at‘
on the ?ber in general brown shades of good {ash
65 mess propertiea
tached to the nuclei in positions ortho to the azo ‘1
bridge, yielding when produced on the ?ber in 65,
2_ Water insoluble azo‘ dyestuffs of the general
formula;
i
R--N=N-—R’-—N=N——R’f
0
70
Y
general brown shades of good fastness properties.
4. The water insoluble azo dyestuif of the for
11111131
' _
O—Cu——~0
' ‘1*
\
wherein R stands for an aromatic radical, R’
stands for a radical of the benzene series capable
of coupling twice, which is substituted in a posi'_
tion meta to Y by a member of the group con
" '75 sisting of an amino and hydroxy group, how-
70
N=N
NH:
Cl
N=
01
CHI
75
4
2,117,731
yielding when produced on the ?ber a reddish
brown.
5. The water insoluble azo dyestui! oi the for
mula:
azo bridge, and a compound selected from the
group consisting of nitrosamines, diazoamino
and diazoimino compounds derived from aro
matic amines generally used in the manufacture
of ice colors.
12. Printing preparations containing as essen
tial ingredients 9. compound of the general for
10
10
, 01
wherein R stands for a radical of the benzene
series which is free from water-solubilizing
N
15
groups, Y stands for a member selected from 15
yielding when produced
brown.
6. Fibers dyed with a
20 claim 1.
7. Fibers ‘dyed with a
claim 2.
8. Fibers dyed with a
claim 3.
9. Fibers dyed with a
26
claim 4.
on the ?ber a deep
the group consisting. oi! an oxygen atom and the
group NH, X stands for a member of the group
dyestu? as claimed in
consisting of the amino group and the hydroxy
group, however, for the hydroxy group only when
Y stands for the group NH, and wherein the
bridge 0-Cu-Y is attached to the nuclei in posi
dyestu? as claimed in
dyestu? as claimed in
dyestu? as claimed in
‘
10. Fibers dyed with a dyestuil' as claimed in
claim 5.
11. Printing preparations containing as essen
tial
ingredients 9. compound of the general for
30
mula:
wherein R stands for an aromatic radical, R.’
stands for a radical of the benzene series capable
of coupling twice which is substituted in a posi
tion meta to Y by a member 01' the group con
sisting of the amino and hydroxy groups, how
ever, by the hydroxy group only when Y stands
40 for NH, R and R’ being free from water-solu
bilizing groups, X stands for a member selected
Irom the group consisting of an oxygen atom
and the group COO, Y stands for a member se
lected from the group consisting of an oxygen
45 atom and the group NH, Me stands for a metallic
atom capable of yielding azo dyestu? complex
compounds, and wherein the bridge X—Me--Y is
attached to the nuclei in positions ortho to the
tions ortho to the azo bridge, and a compound
selected from the group consisting of nitros
amines, diazoamino- and diazoimino compounds
derived from aromatic amines generally used in
the manufacture of ice colors.
13. Printing preparations containing as essen
tial ingredients a compound of the general
formula:
z
30
wherein Z stands for a member selected from
the group consisting of hydrogen, halogen, the
nitro group and an alkyl group, Y stands for a
member 01' the group consisting of an oxygen
atom and the group NH and X stands for a mem
ber of the group consisting of the amino group 40
and the hydroxy group, however, for the hydroxy
group only when Y stands for the groupv NH,
and a compound selected from the group consist
ing of nitrosamines, diazoamino- and diazo
imino compounds derived from an aromatic
amine suitable for the manufacture of ice colors.
'I‘I-IEODOR KOLLMANN.
EUGEN GLIETEN'BERG.
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