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Патент USA US2110694

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Patented Mar. 8, 1938
2,110,694
UNITED STATES
PATENT OFFICE
2,110,694
WATER-INSOLUBLE AZO DYESTUFFS
Fritz Ballauf, Cologne-Holweide, and Otto Bayer,
Leverkusen I. G.-Werk, Germany, assignors to
General Aniline Works, Inc., New York, N. Y.,
a corporation of Delaware
No Drawing. Application August 31, 1936, Serial
No. 98,736. In Germany September 7, 1935
10 Claims.
The present invention relates to water-insoluble
azodyestuffs and to ?bers vdyed therewith, more
particularly it relates to Water-insoluble azo
dyestuffs which may be represented by the fol
5 lowing general formula:
SO2—N—R
id
(0'1. 260-89)
The invention is illustrated by the following ex
amples:
Example
I
1
50 grams of cotton yarn are grounded for half
an hour in 1000 cos. of an aqueous solution alka
line with soda prepared in the usual manner from
5 grams of 2’.3’-hydroxynaphthoylamino-2
methyl-4-methoxybenzene. The yarn is then
centrifuged, and the dyeing is developed in 1000 10
'
cos. of a diazo bath at 40° C. prepared in the
N=N—-Rf
15
usual manner by diazotizing 2.4 grams of the
amine of the formula:
In: the said formula R stands for the radical
of a hydrocarbon which may bear substituents,
such as alkyl, hydroxy-alkyl, phenyl, chloro
v‘phenyl', methyl-phenyl, methoXy-phenyl and the
like, and R’ stands for the radical of an aryl
20 amide of an aromatic ortho-hydroxycarboxylic
acid.
Our new dyestuifs are obtainable by diazotiz
ing an amine of the general formula:
20
NH?
and neutralizing with sodium acetate; thereupon
the ‘yarn is rinsed, soaped andv dried. A‘ deep
blue of good fastness to light, to boiling and to 2
chlorinev is thus‘ obtained.
,
Y
‘
The dyestuff corresponds to the following
formula:
SOr-N-OH:
30
NH':
in which R means the same as stated above and
coupling in} substance or on substratum, especial
1y on vegetable ?bers, with an aryl amide of an
aromatic ortho-hydroxycarboxylic acid,ther'eby '
the components being selected in such a manner
that no watersolubilizing group, as, for example,
40 the sulfonic acid- or the‘ carboxylic acid group,
is present.
.
The dyestuffs prepared on the ?ber in general
yield deep shades of fairly good fastness to
light.
The amines of the above constitution are ob
tained, for example, by converting by the action
of‘ agents splitting‘ off water l-naphthylamine-ii
sul'fonic acid substituted in the amino group
into’ the corresponding substituted naphtho
sultams and by nitrating and reducing the same,
$11 doNHOoord
I
.
CH3
Example 2
40
24 grams of 4-amino-N-methylnaphthosultam
are diazotized in the known manner. The diazo
solution is then introduced into an alkaline solu
tion prepared from 31 grams of 2’.3’-hydroxy
naphthoylamino- 2 - methyl- 4 -methoxybenzene.
The reaction mixture is then rendered acid with
acetic acid, and the dyestuif separated is ?ltered
off. A reddish blue powder is thus obtained.
50
2,110,694
2
The dyestuff corresponds to the following for—
mula:
By combination oi—
With—
2’.3’-hydroxynaphthoylamino~
4 - amino - N - ethyl-
a-naphthalene.
2’.3’-hydroxynaphthoylamino-
benzene.
A
dark
nephthosultam.
4 - amino - N - n - butyl-
ue
A
0 or-
naphthosultam.
inth.
2’.3“hydroxynaphthoylamino- _____do_,____ ___________ .. A bhllsh
2.4 - dimethoxy - 5 - chloro-
corlnth
benzene.
2’.3’-hydroxynaphthoylamino
2-methyl-4-chlorobenzene.
2’.3’-hydroxynaphthoylamino-
10
.
_
2-methoxy-i-chlorobenzene.
2’.3’-hydroxynaphthoylamino~ ___._d0._._ ,_ ___________ ._
CH3
red
d i s h
corinth
2’.3’-hydr0xynaphthoylamino- ..___do _________________ ..
A
Qmaphthalene.
Example 3
24 grams of 4-amino-N-methylnaphthosultam
15
A
2-methylbenzene.
|
dark
brown
2'-3’-hyd1'0Xynaphthoylamino- _____do_.,___ ___________ ._
A
navy
A
navy
3-n1trobenzene.
7.8’ - b81120 - 2’.3' - hydroxy-
are converted in the known manner; e. g‘. with
sarcosine, into a watersoluble diazoamino com
ue
_____d0 _________________ __
%arbazoylamino-li-methoxyenzene.
2’.3’-hydroxynaphthoylamino-
2-n1etbyl-4‘methoxybenzene.
pound and mixed with 31 grams of 2'.3’-hydroxy
‘19
4 ~ amino ~ N - nhenyl-
naphthosultam.
2’.3’-hydroxynaphthoylamino- ____.do _____ ___ _________ ..
naphthoylamino - 2 -methyl- 4 -methoxybenzene.
A bluish
vlolet
A‘
2~methoxy-5-chlorobenzene.
By adding 380 cos. of water, 20 grams of Turkey
red oil and 30 grams of caustic soda lye 32%
both products are dissolved. Thereupon 500
grams of a starch tragacanth thickener are
stirred in. The cotton printed with this solution
is dried and then treated with an acid in the
form of a vapour or liquid, developed and soaped.
A reddish blue is thus obtained.
2 - hydroxycarbazole - 3 - ear-
A
2’.3"-hydroxynaphth0y1-
_____do _________________ __
A bluish
2’.3’;hydroxynaphthoy1~
____.do _________________ ._
A bluish
_____do _________________ __
A bluish
__,__do _________________ __
A bluish
boxylic aoid-é-chloro-anilide.
am1no-2-naphthalene.
d iSh
brown
violet
immo - 4- ehloro - 2 - methyl enzene.
7’.8’ - benzo - 2'3’ - hydroxy-
red -
Violet
garbazoylaminoA-methoxy
enzene.
7’.8’ - benzo - 2'3’ - hydroxy-
blae
fl-methoxybenzene.
2’.3’-hydroxynaphthoylamino2.5 - dimethoxy - 4 - chloro-
25
blac
carbazoylamino - 2 - methyl-
The dyestuff corresponds to the following for
cor
mill
_____do _________________ __
4-amino-N-(p-anisyh-
A
naphthosultam.
red-
30
d i s h
benzene.
corinth
2’.3’-hydroxynaphthoylamino- _____do _________________ -.
A bluish
2 - methyl - 4 - methoxy - ben-
corintb
zene.
2’.3’-hydroxynaphthoylamino- _____do _________________ __
A
l-naphthalene.
7’.8’ - benzo - 2’.3’ - hydroxy-
garbazoylaminoA-methoxy
re d -
d i s h 35
corinth
_____do _________________ __
Ablack
_____do _________________ -.
A bluish
enzene.
7’.8’ - benzo - 2’.3’ - hydroxy-
oarbazoylamino - 2 - methyl-
black
4-methoxybenzene.
0H JJO-NH-O-OCH:
CH3
In an analogous manner there is obtained by
using the method above described:
We claim:
1. Water-insoluble azodyestu?s of the general
formula:
45
By combination oi-
With
2’.3’-hydroxynaphthoylamino-
2-methylbenzene.
_
4 - amino - N - methyl -
A blue
naphthosultaml
2’.3’-hydroxynaphthoylammo- .____do _________________ __
A red
2’.3’-hydroxynaphthoylamino- _____do _________________ __
A blue
2-methyl-ii-methoxybenzene.
gli s h
50
ue
2-methyl-5-chlorobenzene.
‘
2’.3’-hydrox,ynaphthoylamino- _____do _________________ __
2.4-d1methoxy5-ehlor0ben-
A bluish
- violet.
zone
‘
22.3’ - hydroxynaphthoylam- \_____do _________________ __ Ablue
in U:
mo-2-ehlorobenzene
_
V
2’.3’-hydroxynaphthoylam1no- _____d0 _________________ __
Ablue
4-methoxybenzene
2’.3’-hydroxynaphthoylamino- __‘__do _______________ _Y__.
A
E-methoxybenzene
red
d i s 11
blue
2’fl-hydlgolxynaphthoylamino- _____do _________________ _. Ablue
-nap
60
a one
7’.8’ - benzo - 2_'.3’ - hydroxy -
_____do _________________ __
$arbazoylam1no-4-methoxyenzene
_
dark
blue
2’.3’-hydroxynaphth0ylamin0- 4-amino-N-hydroxyethA-methoxybenzene
A
A blue
wherein R stands for the radical of a hydrocar~
bon, and R’ stands for a radical selected from the
group consisting of aryl amides of 2.3-hydroxy
naphthoic acid and benzocarbazole-ortho-hy
droxycarboxylic acid, yielding when produced on
the ?ber in general deep shades of good fastness
properties.
2. Water-insoluble azodyestu?s of the general
formula:
yl-naphthosultam
2’i3’-hy%§%xynaphthoylamino_____do _________________ _- Ablnavy
~nap
a ene
ue
7’.8’ - benzo - 2_’.3’ - hydroxy -
65
_____do _________________ ._
carbazoylammo-i-methoxy-
A
navy
65
blue
benzene
2’.3’-hydroxynaphthoylamino%.4 - dnnethoxy - 5 - chloro -
4 - amino - N -n - propylnaphthosultam
A bluish
corinth
enzene.
2’i3?h?vdroéynaphtholyamino_____do _________________ __ Acorm
bluiil?
-e oxy enzene
70
70
2’.3’-hydroxynaphthoylamino- _____do _________________ __ A bluish
2-methy1—4-methoxybenzene.
eorinth
2’.3’-hyd:€§3inaphthoylam1no___._do _________________ _. Ablnavy
a-nap
a one.
no
2’g’—hy%lé%xynaphthoylamino___._do _________________ ._ Abl ue.
dark
-nap
a ene.
7’.8’ - benzo - 2'23’ - hydroxy '
Vgu‘bazoylammoA-methoxyenzene.
75
_____do _________________ _.
A black
ish blue
wherein R’ stands for the radical of a 2.3-hy
droxynaphthoic acid aryl amide, yielding when
produced on the ?ber in general deep shades of
good fastness properties.
-
75
2,110,694
3. Water-insoluble azodyestu?'s of the general
formula:
5. The
formula:
3
water-insoluble azodyestuff
of the
SOB-N-OHZ
6
N=N
0
10
wherein R’ stands for a radical of the benzene
series, yielding when produced on the ?ber in
general deep shades of good fastness properties.
4. The water-insoluble azodyestu?’s of the
formula:
15
yielding when produced on the ?ber blue shades
of good fastness properties.
20
N:
0H comm-Q2:
X
25
wherein one X stands for a methoxy group and
6. Fibers dyed with a dyestu?
claim 1.
7. Fibers dyed with a dyestuff
claim 2.
8. Fibers dyed with a dyestuif
claim 3.
9. Fibers dyed with a dyestuff
claim 4.
10. Fibers dyed with a dyestuif
claim 5.
as claimed in
as claimed in 20
as claimed in
as claimed in
25
as claimed in
the other X stands for hydrogen, yielding when
30
produced on. the ?ber, blue shades of good fast
ness properties.
FRITZ BALLAUF.
OTTO BAYER.
30
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