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Патент USA US2131866

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Patented Oct, 4, 1938
2,131,866
“UNITED” STATES PATENT OFFICE
r 72,131,866
WATER I'NSOLUBLE AZO DYESTUFFS
7 Werner Zerweck and Karl Schiitz, Frankfort-on
,1 the-Main-Fechenheim, Germany, assignors to
General Aniline Works, Inc., ‘New York, N. Y.,
> a corporation of Delaware
‘
’ 1No>fDrawing.-. Application March 9, 1935, Serial
' - No. 10,326, ' In Germany March 17‘, 1934
4 c1aimS'.-‘ 101. 260-164)
ing bath (a), squeezed off or centrifuged and
dyed in a moist state in the developing bath (1)).
Then the dyed goods is rinsed, soaped with a
boiling soap solution and dried.
Our invention relates to‘water insoluble azo
dyestuffs, more particularly, those of the general
formula:
--
1
Cn
O
egg
‘
Y
‘
i
(a)
Impregnatz'ng bath
7
chloro-2,5-dimethoxybenzene are mixed with 20
ccms. of Turkey red oil of 50% strength and 10
|
fN
ccms. of a caustic soda solution of 34° Bé., 3.5
ccms. of formaldehyde of 30% strength and the 10
I
solution thus obtained is made up with water
OH
R
to 1 liter.
.
I
‘
o ONE-31
15:
I
4 grs. of 1-(2',3’-hydroxynaphth01amin0)-4
-
(1)) Developing bath
1.5 grs. of 1-amino-2,5-dibenzoy1benzene are
wherein Y stands for a member of the group con
diazotized in the usual manner, sodium acetate
and 30 grs. of sodium chloride are added and the
solution thus obtained is‘made up with water to
'sisting of hydrogen, methyl and halogen, and
a
1 liter.
stands for a radical. of the group consisting of the’
‘
r
v
v The dyestuif thus produced on the ?ber of the
20 naphthalene, carbazole and benzo-carbazole se- ‘ ‘
formula:
ries, and ‘R1 stands ‘for a radical of the group con-~
sisting of phenyl, substituted phenyl and naph
v
_ thyl, no water solubilizing group being present
in the whole 'molecule. The new dyestuffs are
'25 obtained by combining in substance ior~ on the" '
‘
?ber diazo derivatives of amines which do- not‘
contain a water solubilizing group andhave the _
general formula: ‘
06113
.
‘
\
15
25
N
>
20.
110
a
I‘ ClQHN-OC
30
OOHa
‘
,l.
ydyes cotton scarlet shades of an excellent fast
' ness to light, chlorine and kier-boiling.
NHa
v
Example 2
35 wherein Y has the aforesaid ,signi?cation'vlwith “"
arylamides of the benzene and naphthalene‘series v 30 parts of 1‘-amino-2,4-‘dibenzoylbenzene are
70f ortho hydroxy carboxyli'c acids‘of the naph-3 tdiazotized and the‘vdiazo solution thus obtained is
35
‘ "1 combined with an aqueous suspension of 29.3
thalene, carbazole and benzo-carbazole series.
Compared. with the analogous "dyestu?s obi 7 parts _ 0f 1 (2' ,3’-hydroxynaphthoylamino) - 2 tained by starting from‘ ‘diazo- compounds con—; methoxybenzene prepared by dissolving the
taining only-one aroyl group vthe present dyestu?s
40
' aforesaid quantity of the arylamide in an alco
are distinguished by better fastness particularly ‘ holic caustic soda solution, diluting with water
and adding acetic acid until it has a slightly alka
to light, boiling caustic soda ‘solution, andiron
ing.
»
1
‘
’
line reaction. The dyestuff thus obtained of the
'
The above bases are obtained for instance by , formula:
45
condensing according to Friedel-Cr‘afts" reaction
nitro-aryl-dicarboxylic acid chlorides with aro- ‘ ».
>
matic hydrocarbons which may contain further I
00-6
substituents but no group‘ rendering the product
water-soluble, and reducing, the condensation .i
product formed;
I
‘V
e
50
V
In order to further illustrate our invention‘ the
following examples are given; but we wish it,
however,-to be understood that our invention is
I‘ not limited to the‘ particular products or reaction ‘
conditions stated therein,
Example-1 f
, 50 gig. ‘5f ‘wen boiledxlic‘otton yarn- is handled‘ ; ‘is
for about half an hour‘in'l‘liter of an‘impregnat-_'
55
' nN_oc
when dry a scarlet powder which may be used
2
2, 131,866
for the production of valuable scarlet color lakes.
In the following teble a number of further dye
stu?s obtainable according to the present inven
tion are described:
Dyestu?, obtained bfy the diazo compound
1-emino-2,S-dibenzoylbenzene. ____ _-V_.;.____
l (2’,3'-hydroxynaphthoylamino) 2-methoxyben~ Yellowish scarlet.
zene.
10
Shade of the dyestu?
when produced on
the?ben~
Combining with
0 __
.
l (2’,3’-hydroxynaphthoylamino)2, 5-dimeth0xy
10
Scarlet.
benzene.
1 (2’,3’-hydroxynaphthoylamino) 2,4-dimethoxy
Yellowish red.
?-chlorobenzene.
l-amino-Z, 5-dibenzoylbenzene ____________ __
p-Anisidide of the 7, 8-benzocarbazole-3’-hy
Dark blackish violet.
droxy-2’-cerboxy1ic acid of the formula:
15
15
2b
20
25
25
30
30
CH3
l-amino-Z, 5-di-p-toluylbenzene ___________ __
1 (2', 3’-hydroxynaphthoylamino) 2-ethoxy
Yellowish scarlet.
benzene.
1 (2’, 3’-hydroxynaphthoylamino) 2-methyl
Do .
benzene.
1 (2’, 3’-hydroxynaphthoylamino) 2.4-dimeth
35
vYellowish red.
oxy?-chlorobenzene.
35
1 (2’, 3’-hydroxynaphthoylamino)-naphthalene._ Alizarine like red.
1
(2’- hydroxycarbazole - 3'- carbonylamino) - 4
Chocolate like brown
chlorobenzene oi the formula:
40
45
40
1-amino-2, 5-di-(p-chlorobenzoyl)-benzene.. 1 (2’, 3’-hydroxynaphthoylemino)-2-meth0xy
benzene.
50
'
Scarlet.
‘
Do _____________________ _-___;___.'___.-____
1 (2’, 3’-hydroxynaphthoylamino) 2-methyl-4
chlorobenzene.
2 (2’, 3’-hydroxynaphthoylamino)-naphthalene-_ Yellowish red.
Do ____________________________________ __
1
Do“; _________________________________ _.
V
(2’ - hydroxycarbazole - 3’ - carbonylamino) - 4
I
Do.
Chocolate like brown.
chlorobenzene.
1'amino-3, 5-dibenzoylbenzene ____________ -_ 1 (2’, 3’-hydroxynaphthoylamino)-2-ethoxyben
Yellowish scarlet.
zene.
1 (2’, 3’-hydroxynaphthoylamino)-4-1:netl1oxy
benzene.
1 (2’-hydroxycarbazo1e-3’-carbonylamino)-4-chlo
robenzene.
55
i
Do.
Brown.
,
p-Anisidide 0i 7.8-benzocarbazole-3’-hydroxy-2’
carboxylic acid.
Blackish violet.
Terephthaloyl - bis - acetic - acid - 2 - methoxy
Greenish yellow.
4'chloro-5-methylanilide oi the formula:
0 on.
60
CO-OHPdO-NH
60
01
CH1
CH3
CH!
1-amino-2, 4-dibenzoylbenzenens __________ __
1 (2’, 3’-hydroxynaphthoylamino) Z-methyIbenY-V riscavrlet. 5
zene.
_,
,
'
1
l (2’, 3’-hydroxynaphthoylamino) Zethoxyben
Z8118.
'
V
.
I
Do:
_
1 (2’, 3’-hydroxynaphthoylemino)-Z,_ 4-dimeth Yellowish red.
1 (2’, 3’-hydroxynaphthoylamino)-naphthalene.
oxy-5-chlorobenzene.‘
i
V
,
.Red.
,1 _,
.
V
2,131,866
r
We claim:
I
_
‘
1. Water insolubleazo dyestu?s of the general
formula:
.
o
t
3
the production of valuable brown color lakes and‘
dyes when produced on the ?ber cotton very fast
chololate like brown shades.
' 3. A water insoluble azo dyes‘tu? of the for
1
mula:
4501f -
'
lI
10
10
N
Rw
O
OH
-— C ONH-R1
15 wherein Y stands for a member of the group con;
15
sisting of hydrogen, methyl and halogen, and
OCHa
which is when dry a scarlet powder suitable for
the production of valuable scarlet color lakes and
dyes when produced on the ?ber cotton very fast 20
-a
stands for a radical of the group consisting of the
naphthalene, carbazole and benzo-carbazole se:
ries, and R1 stands for a radical of’ the group con
sisting of phenyl, substituted phenyl and naph
thyl, no water solubilizing group being present in
25
yellowish scarlet shades.
'
4. A water insoluble azo dyestu? of the for
- mula:
the whole molecule, which dyestuffs are suitable
25
for the production of valuable color lakes and dye,
when produced on the ?ber, cotton, valuable
shades of a good fastness.
,
'
2. A water insoluble azo dyestu? of the for
30
mula:
‘
.
t
v
'
,
30
110
N
' .QHN-OC-—
- l
35
‘
HO—-
40
’
'
'
'
CIGHN-O o-
'
.011:
V
>
35
'
‘which is when dry ascarlet powder suitable for
the production of valuable scarlet color lakes and
‘
\N/
V
>
dyes when produced on the ?ber cotton 'very fast
i
scarlet shades. _
.
r
'
t
l
a
'
'
'
which is when dry a brown’ powder suitable for '
WERNER ZERWECK.
KARL SCHUTZ.
40
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