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Патент USA US2134728

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Patented Nov. 1, 1938
' 2,134,728
UNITED STATES
PATENT OFFICE
2,134,728
AZO nms'rurrs
Heinrich Morschel, Cologne-Deutz, and Otto Goll,
Leverknsen I. G.-Werk, Germany, assignors to
General Aniline Works, Inc., New York, N. Y., a
corporation ,of Delaware
'
No Drawing. Application July 28, isssgseriai
No. 93,117. In Germany August 16, 1935
6 Claims. (C1. 8-46)
The present invention relates to water insoluble sulfonic acid. Development is effected with 1
azo-dyestuffs and to a process of preparing same,
liter of a diazo ‘solution produced in the known
more particularly it relates to water insoluble azo
dyestuffs which may be represented by the fol- - manner from 1.75 gs.‘ of 2-nitro-4-anisidine.
After the dyeing has been soaped at the boil, an
lowing general formula:
olive grey issobtained.
'
The dyestuff corresponds to the following for
mula:
'
.
NO:
10
HIN N=N®OCH1
OH
In the said formula X stands for a ‘member
‘selected from the group consisting‘ of hydrogen,
alkyl and aryl, R’ and R',’ stand for radicals of
N=’N
OClIs
diazotization components free from solubilizing
20
groups, and n stands for one of the numbers 1 r
and (2.
I
Our new dyestuffs are obtainable by coupling
suitable diazo compounds with 4-arylazo-1-am
Example 2
Cotton is printed with a paste produced as 20
follows:
ino-‘l-hydroxynaphthalene or their N-alkyl or N- E
25 aryl substitution products.
4
Amixture of
In as much as in the
aryl nucleus of the 4'-arylazo group a further
4-(2'- chloro) - benzene-azo-1-amino-7-hy
suitable coupling position is present, by employ
ing a correspondingly larger, quantity of diazo
The'diazoamino compound from diazotized
4-chloro-2-anisidine and sarcosine___gs_.. 3
droxynaphthalene ________________ __gs__
compound trisazo dyestuffs and ‘so on can be
30
1.0
'
manufactured.
I
-
l
4.5
An aqueous solution of caustic soda of 38°
'
Bé _____________________________ __ccs.._
The new dyestuffs can be manufactured with
3
Glycolmonomethyl ether ___________ __ccs.._ I 5
particular success on the ?ber according to the
method of producing ice colors as the compounds
Neutral starch tragacanth paste _____ __gs_- 50
of the type ofv ll-arylazo-1-amlno-7-hyiiroxy
is made up with water to 100 gs. After an inter
35 naphthalene possess a good affinity for the ?ber.
The new dyestuffs yield in general powerful
dark brown to black shades.
25
mediate drying, development is effected with acid‘
steam, and then the dyeing is soaped ‘at the boil. 35
. A black shade is obtained.
The following examples illustrate the invention:
Example 1
40
.Cotton ?ber is slop-padded with the following
grounding solution: 3 parts by weight of 4(2'
The dyestuff corresponds to the following for- ‘
mula :
0 OH:
40
inethoxy)-benzeneazo¢1-amino- 7 -hydroxynaph
thalene are stirred into a mixture of 3 parts by
weight of water, 6 parts by weight of alcohol and '
1.5 parts by weight of an aqueoussolution of caus
tic soda of 38° Bé., and the whole is made up to 1
- 'liter with a solution containing per liter 10 cos. of
an aqueous solution of caustic soda of 38° Bé., .10
50 cos. of vpuri?ed sul?te cellulose ‘waste liquor and
1 g. of the sodium salt of polyisobutylnaphthalene
45
2,184,728
2.
Example 3
When in the printing paste of Example 2 there
is used the diazoamino compound from diazotized
4-chloro-2-toluldlne and sarcosine, a saturated
dark brown is obtained.
l'ghe dyestuff has the probable following for
'
"fl‘he dyestuff corresponds to the following for
m
100 gs. Cotton is printed vwith this paste. After
drying the print is steamed for 5 minutes with
steam-containing acetic acid. Then the mate
rial is rinsed, soaped at the boil, again rinsed
and dried. A deep black shade is obtained.
m
a:
a:
.10
OH
1
15
E .
NO:
20
Cl
'20
In the following table there are given further
Example 4
2.5 gs. of the diazoamino compound, which
combinations prepared in accordance with the
present process and their shades on cotton:
25
25
Coupling component
Diazo component
Shade on cotton
4(1-methyl-5’ chlotophenylezo)-l-amino-7-hydroxynaph- .2-nitro-4-chlorauiiine ............................ _. Olive-brown.
no
30.
'
'
D0
'4’—nitro-4-nmino-2,5-dimethoxyazobenzene........ .-
____ _. -
3-chloraniline ............................ __
Blackish brown.
..
30
Greyish brown.
‘(T-mthoxy-iV-chlorophenylaw)-1-amino-7-hydroxynapb- 2,6-dichloroaniiine ............................... .. Brown-olive.
Dn
.
__
2-chloro-a-methoxy-4-ben1.oylamino-i-aminoben-
'
35
Blackish brown.
zene.
4(2'-methoxy-5’-chloro-l-emino-7-hydroxy-uaphthslene..__ 4-nitro~2-amino-l-methylbenzene ................. __ Olive-brown.
‘(T-nitrophenylnao)-l-amino-7-hydroxy-naphthalene.. . ___ kchloro-2‘amino-1-methoxybenzene.
Brownian black,
Do
._ b-nitro-2-emino-l-methoxybenzene...
Dc
‘
______ __
_
Greenish black.
4-chloro-3-amino-1-triiiuoromethylbe
Reddish hlack brown.
4(2'-chlorophenyluo)-1-am1no-7-hydroxynaphthalene....-- 3-chioreniline .............. .._---.Do
- i-chloro-z-amino-l-methoxybenzen
Do
I
_.
.... ._
Greenisb black brown.
Bluish dark brown.
l-amino’nnthraquinone ....... _-
Dark brown.
4(2'-methoxyphenylar.o)-l-emino-7-hydroxynaphthalene_ _ . 2’ ,3-dirnethyl-4-aminoazoben1-en
Brownish olive.
. 2.5-dichloraniline_..__
Do.
40 4(?itro-?-methyipbenylazo~1-amino-7-hydroxynephtha- Itchlorauiline ______ ._
40
Dark brown.
e.
.
4(7-methoxyphenylazo)~1amin0-7-hydr0xynaphthalene
.. B-amino-l-chiom-l-tri?uormethylbenzene
......... _. Bleckish brown.
“?itro-f-methylphenylaw-l-amino-7-hydroxynephths- 5-cliloro-2-nmino‘l-methylbenzcne _______________ __
e.
D0
4(1-nitm-4'-metboxyphenylaz0)-1-emino-7-hydroxynsph- 4-chloro-2-amino-1-metl1ylbenzene ............... __'
.45
2(2’-nitn>4'-methoxypbenylam)~1-amino-7-hydroxynaph
4(1-nino-4'-methoxyphenyluo)-1-amino-7-hydmxynaph
timiene.
Y
thalene.
.
.
4(7'-hydxoxynaphthyl-(l’) ~ezo) - l -emlno- 7 -hydroxynaph
thabne.
__
50
D0
..... __
4(2' - nltmphenylazo) - 1 - methylamino - 7 - hydroxynapli
thulene.
J
Do
Do.
Greenish black brown;
5-chloro-2-amino-1-metl1ylbenzeue..; ............ ._
Blackish brown.
5-nitro-2-emino-1-methylbenzene ................. _ .
Olive dark brown.
4-chloro-2-amino-1-methoxybenzen
_ _ _
hy?oxynaphthalene.
henylsso)-1-etbylamino-Whydroxynaphthaleue.
4(1-nitrop
euyluo)-l-etbylamino-7-hgdmgnnphthalene.
?il-lnitrophenylam)-1-phenylamino- -lzy roxynaphtlma
>
hydmxymphtlnlene.
60
D0
, D0“
Greeuisli black.
ine ____________________ .-
‘
- .___
_.
Greenisb black.
'
4-nitmniline__._-‘_ _______________________________ __
Olive.
6-11itm-i-amino'l-methoxybenzene _____________ __‘._
Greenish blackish brown.
_
2,5-dichloraniline__ ___________ __. ________________ __
4-nitrsniline
-..
'
is obtainable from diaz'otized 4,4'-dia.mino-3,3'
dimethcxydiphenyl and sarcosine (=1/200 mol) ,
and 3.1 gs. or 4(2'-nitrophenylazo)~1-amino-7
hydroxynaphthalene (=1/200 mol) are stirred
into a paste with the aid of a small quantity of
water and dissolved by adding 3.0 com. of caustic
soda solution of 38'’ B6. and 5.0 ccm. of glycol
The so
lution is added to a neutral starch tragacanth
paste while stirring and ?lled up with waterto
70 monoethylether while slowly heating.
Brown.
Dark olive brown.
2,5-dichlor'aniline_ ........................ ., ____ _- Olive brown.
.
4(4' - nitropheuylaso) - 1 - (4" - methoxyphenylamino) - 7 -
50
. Blackish brown.
5-chloro-2_-amino-l-methylbenzene ............... __
0.
Do
Black.
l-chlom-2-amino-l-methoxybenzene
4(3'
55
Do.
Yellowish dark brown.
4-nitzo~l-amino-benzene __________________ ._
5-chl0ro-2'emino-i-methylbenzone__
'
'
4(2' - methoxy - 5 - chlorophenylew) - 1 - methylemino - 7 -
Do.
5-nitm-2-emino-l-methoxybenwne ............... __
2-aminodiphenyl-sulione _______ __
.
Do.
4-chl0ro-2-amino-1-metl1oxybcnzene .............. __
We claim:
\
'
.
Blackish brown.
Ycllowlsh dark brown.
,
1. Water insoluble azodyestu?s of the general
formula:
65
H
x
l
I
70
2,134,728
wherein X stands for a member selected from
the group consisting of hydrogen, alkyl and aryl,
R’ and R" stand for di?erent radicals of di
3
amines and amino azo compounds with a com
pound of the general formula:
azotization components free from solubilizing
H
\N
groups, and n stands for one of the numbers 1
.
x/
and 2, yielding when produced on the vegetable
?ber in general brown to dark shades.
2. A water insoluble azodyestuif of the for
mula ;
on
R'-—-N=N
NH, N02
|
the group consisting of hydrogen, alkyl and aryl,
R’ stands for the radical of a diazotization com-'
—OH OCH:
15
]
wherein X stands for a member selected from
ponent free from solubilizing agroups, yielding
when produced on the ?ber in general brown to
dark brown to black shades.
6. The process for the manufacture of water
‘insoluble azodyestu?’s which comprises combin
.20
ing on the ?ber a diazo compound free from
- solubilizing groups derived from an amine select
ed from the group consisting oi.’ monamines, di
amines and amino azo compounds with a com
pound of the general formula:
25
-
H
\N
x/
yielding when produced on the vegetable ?ber
30
OH
‘ deep black shades.
3. Fibers dyed with a dyestu? as claimed in
Claim 1,
al ;
I
4. Fibers dyed“ with a dyestu? as claimed in
claim 2.
R’—N=‘N
‘ i
5. The process,‘ for themanufacture of water
35 insoluble azodyestuifs which comprises combin
ing on the ?ber a diazo compound free from
solubilizing groups derived from an amine select
ed from the group consisting of monamines, di'
wherein‘ X stands for a member selected from
the group consisting of hydrogen, alkyl and "aryl,
R’ stands for a radical of the benzene series free
from solubilizing groups, yielding when produced
on the ?ber in general brown to dark brown to
black shades.
HEINRICH MORSCHEI...
O'I'I'O GOLL.
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