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Патент USA US2122127

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2,122,127
Patented June 28, 1938
PATENT orgies
UNITED ' STATES
2,122,127
ORTHO-HYDROXYAZO DYES AND‘ rnoonss
FOR MANUFACTURING THE SAME‘.
Germany,
Walther Benade, Dessau in Anhalt,
Aniline
Works,
Inc., New
assignor to General
York, N. Y., a corporation of Delaware
No Drawing. Application December 31, 1936,
Serial No. 118,572. In Germany January 17,.
1936
I
,
6 Claims.’
'
(Cl. 260—-94)
tints of good fastness to washing and iulling and
My present invention relates to new ortho
hydroxyazo dyes and to a process for manufac
turing the same.
More particularly it relates to dyes which are
6' suitable for dyeing wool, the dyeing being chr0
mated either by the application of the single
bath-chrome process or by a subsequent treat
ment with compounds forming the chromium
complex compound.
It is based on the observation that valuable
azo dyes are obtained by- coupling the diazo com
pound of an amine corresponding to the general
10
formula
'
very good fastness to light.
,
The 2 — hydroxynaphthalene - 6 - sulfonic acid
anilide-2’-carboxylic acid is obtainable by esteri
fying 2-hydroxynaphthalene-6-sulfonic acid with
benzene sulfochloride, treating the product ob
tained with a phosphorous chloride to form the
corresponding sulfochloride, condensing the latter
with anthranilic acid and splitting oil the ben
1o
zene sulfonic acid-by heating with an alkali lye.
The same dye is obtainable when using as azo
component thev condensation product made from
anthranilic acid and 2-hydroxynaphthalene-l
carboxylic acid ?-sulfochloride. 'In this case the
COOH-group in 1-position is split’ off -when 15-1
coupling with the diazo compound,
16
wherein X is a radicle of the group consisting of
--OI-I and -COOH, X being in ortho-position .to
the -NH2-gr0up and R is a radicle of the group
20
-
Example 2.-Into a solution of 35 parts of
1-hydroxynaphthalene-5-sulfonic acid anilide
2'-carboxylic acid and 25 parts of calcined sodium
consisting of a benzene-, chlorobenzene-, nitro
carbonate in about 1000 parts of water there is 20
benzene-, alkylbenzene-, chloronitrobenzene
radicle and the alkyl derivatives thereof, with a
hydroxynaphthalene sulfonic acid anilide which
runthe diazo-mixture obtained from 199 parts
of
contains a carboxyl group as a substituent in the
water. The dye which is worked up in the usual 25?
manner is, when dry, a dark powder soluble in
water to a red-violet solution and dyeing wool by
anilide radicle and corresponds to the general
4,6-dinitro-2-amino-l-hydroxybenzene,
6.9
parts of sodium nitrite and 25 parts of hydro
chloric acid of 12° Be. in about 500 parts of
the single bath-chrome process a greenish black
of good properties of fastness.
The preparation of the l-hydroxynaphthalene 3,0":
5-su1fonic acid ani1ide-2’-carboxy1ic acid is car
ried out in an analogous manner as pointed out
in Example 1 when starting from the benzene
sulfonic acid ester of 1-hydroxynaphthalene-5
sulfonic acid.
The dyes are characterized by a good dyeing
capacity by the single bath-chrome process and
yield on wool dyeings which have good fastness
to washing and fulling as well as good fastness to
40‘ light.
The following examples illustrate the inven
tion, the parts being by weight:
Example 1.-18.9 parts of 4-nitro-6-chloro
Z-amino-l-hydroxybenzene are suspended in 200
4152 parts of water and after addition of 25 parts of
hydrochloric acid of 12° Bé. are diazotized by
means :of 6.9 parts of sodium nitrite. The diazo
mixture is run into a solution mixed with ice of
35 parts of. 2-hydroxynaphthalene-6-sulfonic
_
Example 3.-17.8 parts 'of 4.6-dich1oro-2-ami
no-l-hydroxybenzene are diazotized in 400 parts
of water by addition of 25 parts of hydrochloric
acid of 12° Bé. and 6.9 parts of sodium nitrite.
The diazo compound is allowed to run into a
solution of 35 parts of l-hydroxynaphthalene-4
sulfonic acid anilide-2’-carboxy1ic acid. When
coupling is complete the dye is separated and
dried. It dyes wool by the single bath-chrome
process violet tints of good fastness.
The
1 - hydroxynaphthalene - 4-su1fonic
acid
anilide-2’-carboxylic acid is prepared by the se
quence of reactions indicated in Example 1 when
starting from 1-hydroXynaphthalene-4=—sulfonic
acid anilide-2'v-carboxylic acid and 25 parts of
calcined sodium carbonate in about 1000 parts of
acid.
Water. When combination is complete the dye is
carboxylic acid and 25 parts of sodium carbonate
worked up in the usual manner. On drying it forms
a dark powder of. good solubility which dyes wool
55 by the single bath-chrome process violet-brown
.
Example 4.-—A solution of 35 parts of 2-hy
droxynaphthalene - 4 - sulfonic
acid anilide-2'
in about 800 parts of water is united with the
diazo compound prepared from 15.4 parts of 4 55
2
2,122,127
nitro-2-amino-l-hydroxybenzene, 6.9 parts of
icles, and coupling the diazo compound with 2'
sodium nitrite and 25 parts of hydrochloric acid
of 12° Bé. in about 400 parts of water. The dye
formed is separated by addition of common salt
and dried. It dyes wool in the presence of a
hydroxynaphthalene-6-sulfonic acid anilide-2'
carboxylic acid of the formula
/OH
chromium mordant black tints.
Dyes of similar properties are obtainable when
/
ONHols/
using instead of 4—nitro-2-amino-1—hydroxyben
zene the substitution products thereof as, for in
10
stance, 6—chloro-4-nitro-2-amino-l-hydroxyben- 1
zene or 6-methyl-4-nitro-2-amino-l-hydroxy
benzene.
In the foregoing examples 2-amino-1-hydroxy
benzenes are used as diazo components.
COOH
3. The process which comprises diazotizing an
thranilic acid and coupling the diazo compound 1O
»with 2—hydroxynaphthalene—6-sulfonic acid ani
lide—2'~carboxylic acid of the formula
How
/OH
15 ever,_ in an analogous manner 2-aminobenzene—1-'
carboxylic acid and its nitro-, halogeno- or alkyl
/
substitution products may be diazotized and cou
pled with the hydroxynaphthalene sulfonic acid
anilides bearing a —COOH-group in the anilide
20 radicle. This modi?cation is illustrated by the‘
following example without being limited to the
speci?c details given therein.
Example‘ 5.—-13.7 parts of 2-aminobenzene—1
OOOH
15
QNHOZS
4. The ortho-hydroxyazo dyes which yield on
wool with a chromium mordant tints of good 20
fastness to light, to washing, and to fulling and
which correspond to the general formula
carboxylic acid are diazotized in the usual man
25. ner. The diazo compound is allowed to run into
OH
Rzlnmslm
an iced solution of 25 parts of 2-hydroxynaph
thalene-?-sulfonic acid anilide-2’-carboxylic acid
in 100 parts of water containing 30 parts of cal
cined sodium carbonate. The dye formed is
worked up in the usual manner. After drying, it
forms a red powder of good solubility. The chr0
25
30.
mated dyeings on wool are red of good fastness
to washing, fulling and light.
35
What I claim is:
1. The process which comprises diazotizing an
amine of the general formula
in which X is a member of the group consisting
of —OH and —COOH, X being in ortho-position
to the azo-bridge and R is a member of the group 35
consisting of the benzene-, chlorobenzene-, nitro~
benzene-,
radicles.
wherein X is a member of the group consisting
of —OH and —COOH, X being in ortho-position
to the NHz-group and R is a member of the group
45:
alkylbenzene-,
5. The ortho-hydroxyazo dyes which yield on
wool with a chromium mordant tints of good
fastness to light, to’washing, and to fulling and
which correspond to the general formula
consisting of the benzene-, chlorobenzene-, nitro
benzene-, a1kylbenzene-, chloronitrobenzene-rad
45
icles, and coupling the diazo compound with a
hydroxynaphthalene sulfonic acid anilide of the
general formula
60'
chloronitrobenzene
(IJOOH
OH
31,,IIIH
55
—COOH
50
in which X is a member of the group consisting
of —OI-I and —COOH, X being in ortho-position
to the azo~bridge and R is a member of the group
consisting of the benzene-, chlorobenzene-, nitro
benzene-,
radicles.
alkylbenzene-,
chloronitrobenzene
65
>
6. The ortho-hydroxyazo dyewhich dyes wool
2. The process which comprises diazotizing an
60 amine of the general formula
R
65
with a chromium mordant red tints of good fast
ness to washing, fulling'and light, which corre
sponds to the formula
60
/
\NHz
65
wherein X is a member of the group consisting of
-OH and -COOH, X being in ortho-position
to the NHz-group and R is a member of the group
consisting of the benzene-, chlorobenzene-, nitro
70
benzene-, alkylbenzene-, chloronitrobenzene-rad
WALTHER BENADE.
70
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