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Патент USA US2128537

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2,128,537
Patented Aug. 30, 1938
UNITED STATES
PATENT OFFICE
2,128,537
DISAZO DYESTUFFS
Jose Stephen Petrus-Blumberger, Delft, Nether
lands, assignor to General Aniline Works, Inc.,
New York, N. Y., a corporation of Delaware
No Drawing. Application April 22, 1936, Serial
'No. 75,884. In Germany May 2, 1935
v4 Claims‘. (Cl. 260-475)
The present invention relates to new azo dye
stuffs, more particularly it relates to dyestu?s
which may be represented by the general formula:
The dyestu?, having in the free state the follow
ing formula:
'
'
OH
0H
,
I
wherein B stands for a radical of the benzene
series'bearing the azo-group in'meta-position to
' v
' HOzS/
_ the NH group, such as a benzene nucleus which.
NH:
“ may bear substituents, e. g. methyl, a halogen
atom, or a carboxylic acid-group.
.7
‘
"
7;.
R stands for the radical of 1-amino-5-naph
thol-7-sulfonic acid or of 2~amino-8-naphthol-6
sulfonic acid and R1 stands for a radical of 1
20 amino-5-naphthol-7-sulfonic "acid, 2-amino-8
naphthol-G-sulfonic acid, or 2-amino-5-naph
thol-7-sulfonic acid, the 2 coupling components
being coupled to the hydroxy side.
25
I
15
is ?ltered o? in the: cold, squeezed and dried. It
yields on cotton Bordeaux shades,‘ which, after
tetrazotizing and developing with ?-naphthol re
main Bordeaux, with toluylene-diamine yield a
reddish brown.
In an analogous manner have been prepared the
dyestuffs of the following formula:
'
My new dyestuffs are obtainable by coupling
25
tetrazotized 3,3’-diaminodiphenyl urea or a homo
logue thereof ?rst with 1-amino-5-naphthol-7
sulfonic acid or 2-amino-8-naphth01-6-sulfonic
acid and then with one of the said components
0 or 2-amino-5-naphthol-7-sulfonic acid.
3
The dyestu?s thus obtainable can be tetrazo
tized on the ?ber and developed with the usual
developers such as B-naphthol or toluylene di
amine.
35
In this manner are obtained in general Bor
deaux to brown shades of good fastness to wash
ing and good dischargeability, both, with a neu
tral and with an alkaline discharge paste.
The invention is illustrated by the following
40 examples, but it is not restricted thereto.
35
40
Examples
45
121 parts of m,m’-diaminodiphenyl urea are
tetrazotized with 69 parts of sodium nitrite and
v 300 parts of concentrated hydrochloric acid and
then the ?nished tetrazo solution is poured into ,
a solution alkaline with sodium carbonate of
50 239 parts of 1-amino-5-naphthol-7-sulfonic acid.
45
Both dyestuffs yield on cotton corinth shades,
which, when tetrazotized and developed with
2
2,128,537
toluylene-diamine, are turned to deep brown.
When using B-naphthol as developer, the shade
of the ?rst dyestuff remains unchanged while
that of the second dyestu?‘ is turned to a bluish
corinth.
I claim:
yielding on cotton Bordeaux shades, which, after
tetrazotizing and developing with e-naphthol re
main Bordeaux, with toluylene-diamine yield a
reddish brown.
3. The dyestuff having in its free state the fol
lowing formula:
1. A20 dyestuffs of the general formula:
OH
NH——B—N=N—-R
N=N
0o
IIIEPG
1
0
3
s
;
::\NH2
1511
/
IlIH~B—N=N—R1
wherein B stands for a radical of the benzene
series bearing the azo-group in meta-position to
the NH group, R stands for the radical of an
10
CO
Q
15 amino naphthol sulfonic acid of the group coh
OH
\N=N
sisting of l-amino-5-naphthol-'7—sulfonic acid and
of 2-amino-8-naphthol—?-sulfonic acid and R1
stands for a radical of an amino naphthol sulfonic
NH:
15
HOsS
acid of the group consisting of 1-amino-5-naph
yielding on cotton corinth shades, which, after 20
fonic acid, and 2-amino-5-naphthol-'7—sulfonic ‘ tetrazotizing and developing with toluylene
acid, the 2 coupling components being coupled diamine are turned to deep brown.
4. The dyestuff having in its free state the fol
to the hydroxy side, yielding, when tetrazotized
on the ?ber and developed in general Bordeaux lowing formula:
OH
to brown shades of good fastness to washing and
25
thol-7-sulfonic acid, Z-amino-8-naphtho1-6-sul
good dischargeability.
V
_
I
2. The dyestuff having in its free state the fol
lowing formula:
N:
/
NR0
(\10
3O
Hols
I'm-c}
NH,
OH
30
*NH:
35
35
11038
yielding on cotton corinth shades, which, after
tetrazotizing and developing with toluylene
diamine are turned to deep brown.
HOaS
JOSE’! STEPHEN PETRUS-BLUMBERGER.
NH:
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