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Патент USA US2133439

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Patented Oct. 18, 1938
’ 2,133,439
PATENT OFFICE
MONOAZO DYESYTUFFS
Richard Fleischhauer, Frankfort-on-the-Mainr
Fechenheim, Germany, assignor to General
_ Aniline Works, Inc., New York, N. Y., a cor
poration of Delaware
' No Drawing}, Applicationseptember so, 1936,
Serial No. 103,363. In Germany October 2,
1 " y " 1935 7'
r
' lolaims.
This invention relates to valuable new monoazo
(o1. 260'—163)
The new dyestuffs are particularly useful for
dyestuffs, more particularly to those of the gen
dyeing animal ?bers.
eral formula:
from the analogous dyestuffs notcontaining the
.
following
Y-om
acyl
and benzene series, Z stands fora member se-.
lected from the group consisting of hydrogen and
—-SO3H, ‘andR meansthe radicle of a coupling
,.
_
_
_
Thenew dye'stuifs are obtained bycombi'ning
the diazo compounds of aromatic amines of the
general formula:
..
acyl
wherein X and ,Y stand for members selected from
the group consisting’ of ‘hydrogen and vmethyl
acyl stands for an acyl radical and the aliphatic
component.
group:
1
2
151
'-'X~—OH,
’ NHz
‘
'
.
7'
.
'
v
.
in their ‘diazo-component partly by clear more
yellowish shades and partly by an increased level 10.
ling power.
v
Example 1
19.2 parts of 1-(N-acetyl-isopropylamino)-4
aminobenzene are diazotized in the usual manner
and the diazo solution obtained is allowed to run
into a solution of 32- parts-V of '2-.naphthol-6;8-
disulfonic acid containing an excess of'sodium
The dyestuff thus obtained of the‘
20
H30
‘ I’
|
Z
,
carbonate.
formula:
'
ore-N
acyl
Y-CH:
They are distinguished
_
\
H30
.
,
‘OH-N‘
/'
I
N=N
1
00
1
(wherein X, Y and Z have the above signification)v
son;
|
HO
CH3
with a coupling: component. ‘
The diazo components employed for the inanu?’
facture ofgthef dyestuffs of this inventionp'have,
not hitherto been‘ described. They maybeqbj
tained for example , by , acting 1 with ‘ ;1f-chloro:"l-v
30"
nitrobenzene 'or 1-chloro-4-nitrobenzenef27sul
fonic acid on' the corresponding aliphatic‘ amines, _
is isolated and dried.
It forms a bright orange
colored powder, soluble in water, dyeing wool and
silk bright yellowish orange shades of good fast
ness to washing and light and of good levelling
power.
_
so?
'
if necessary splitting ‘off the sulfonic group, acylat¢
By employing instead of the 2-naphthol-6.8
ing the amino group and reducing th'ejf’nitro“ disulfonic acid other naphthol-mono-or-disulfonic
group. Thus, for example, i- (N-acetyl-isopropyl
acids such as per example 1-naphth0l-4-sulfonic
35-1 amino) ~4-aminobenzene may be‘ prepared ‘by
acid, 1-naphthol-3-sulfonic acid, 2-naphthol-6
heating 1-chloro-4-nitrobenzene—2-sulfonic acid‘
with an excess of isopropylamine in the presence
of an aqueous solution of sodium carbonate in an
autoclave to about 130° C. for about 30 hours.
40 The resulting 1-isopropylamin0—4—nitr0benzene
2‘-sulfonic acid is then treated with dilute'sul
'furic acid in an autoclave at'about 1359C. for‘
about" 20 hours so 'as to split 011’ the sulfuric acid
group. ‘The yield thereof, which is about 85%
45 of‘ the theoretical} is subsequently iacylated' by
heating with’ acetic anhydri'de in the presence of
sulfonic acid, -1-naphthol-3.?edisulfonic acid or’
1,-naphthol-3.8-disulfonic acid dyestuifs are ob-v
tamed-which yield similar orange to yellowish red‘
shades of likewise good levelling power.
Example 2
25.4 parts of 1-(N-benzoyl-isopropylamino)-4
aminobenzene are diazotized in- the usual manner
and the diazo solution obtained is allowed to run
into a solution of 37 parts of 1-acetylamino-8 45
naphthol-3.6-disulfonic acid containing an excess
When the combinationis
a small amount of concentratedsulfuric acid,v of sodium carbonate.
whereby 1-_(N-acetyl-isopropyl-amino)-4-nitro
benzene is formed with a very goodyield. Finally
50 the nitro group of this compound is reduced in ~
the usual manner by ‘means ofv iron: and "acetic
acid and‘ v1-(N-acetyl-isopropyl-amino) —4-amino~
benzene is obtained with a yield of about 75%.
It crystallizes from benzine' in colorless crystals
55 ,‘of 117° C. melting point.
In an analogous manner, l-(N-acetylisec-butyL
amino) ~4-aminobenzene, 1- (N-benzoyl-isopropyl
amino) —4-aminobenzene, 1- (N-benzoyl-s'ec-butyl
amino) -4-nitrobenzene, and the like, may also be
.jprepared.
'
,
complete the'dyestuifformed of the formula:
en rlm- o o 0 H3,
Ha C
/
50"
I
55
is-separated and dried. ~ ‘It is adark' red powder, ,
soluble in water, . dyeingwwool and silkpbright bluish. 60
2
2,133,439
red shades of good levelling power and good fast
ness to fulling, light, seawater and perspiration.
Dyestu?s of similar shades and fastn'ess proper
ties are obtained by replacing the said diazo com
ponent by the corresponding amounts of l-(N
acetyl-isopropylamino) -4-aminobenzene, - l-(N
acetyl-isopropylamino) -3-aminobenzene, ' 1'-(N<
methoxyacetyl~isopropyl-amino) <- 4L a min 0 ben -
ll)
20
The dyestu?! formed by employing 2-benzoyl
amino-5-naphthol-7-sulfonic acid as coupling
component represents a yellowish red powder,
soluble in water, dyeing wool and silk bright
I orange shades of similar fastness properties.
Example 6
' 26.8 parts ‘of ~1- (N-benzoyl-sec-butylamino) -4
zene, l- (N-acetyl-isopropylamino) -4-aminoben - aminobenzene are diazotized in the usual manner
zene-2-sulfonic acid or of analogous amines which and the “diazo ‘solution obtained is allowed to run 10
at’ about 10-15“ C. into a solution of 29 parts of
may contain any other acyl radicle.
2-acetylamino-8-naphthol-6-sulfonic acid con
By combining 1-(N-acetyl-isopropylamino) -4
aminobenzene-2-sulfonic acid with 2-amino'-8 ‘ taining an excess of sodium acetate or sodium bi
naphthol-G-sulfonic acid in a medium containing carbonate. When the combination is complete
a mineral acid a dyestuif is obtained which dyes - ‘the dyestu? formed of the formula:
15
OH
wool bright red shades of good levelling power
and excellent fastness to light.
1110.052
1
Example 3
19.2 parts of 1-(N-acetyl-isopropylamino) -4
/o H-lTI-C>—N=N
H10
-NH—C o 0' H1
CO
aminobenzene are diazotized in the usual manner
and the diazo solution obtained is combined with
37 parts of l-acetylamino-8-naphthol-4.6-disul
fonio acid. The dyestuff formed of the formula:
25
‘CHa
on ‘lrlH-COCHa
\
/CH—III
CH:
N=N'
CO
30
ing, light and perspiration.
>
HOSS
|
SOsH
It is a dark 'red'powder,
soluble in water, dyeing wool and silk brightred
shades of good levelling power and fast to light.
Example 4
35
19.2 parts of 1-(N-acetyléisopropylamino) -4
aminobenzene are diazotized in the'usual manner
and the diazo solution obtained is combined with
26 parts of 1‘-(2'echloro-5'-sulfopheny1) ~3-meth
40., y1-5-pyrazolone.
I
Dyestuifs of similar properties are‘ obtained by
‘
CH3
is isolated and dried.
is'isolated ‘and dried. It is a red powder‘, soluble 25
in water, dyeing wool and silk bright red shades
of good levelling power and good fastness to full
The dyestuff ’ formed of the
employing other diazo components such as for‘ ex
ample
aminobenzene or 1-(N-p-toluenesulfo-isopropyl
amino) Aéaminobenzene.
There may be used as coupling ‘components de
rivatives of 2-amino-8-naphthol-6-sulfonic acid,
l-amino-S-naphthol-G-‘sulfonic acid, 1-amino-5
naphthol-‘l-sulfonicacid or 2-ar'nino-5-naphthol
'7-sulfonic acid containing other a‘cyl radicles such
as for example the methoxyacetyl, chloroacetyl,
carbethoxya'cetyl,
benzoyl, ' hexa-hydro-benzoyl.
and phenoxyacetyl radicle and derivativeslthere'of
substituted in the benzene nucleus. Furthermore,
the. acylamino-naphthalene-sulfonic acids "em
ployed as coupling components may contain in
their acyl'ated amine group aliphatic, hydroaro-v
45
80
1 - (N - benzenesulfo - sec - butylamino) "- 4 -
matic or aromatic radicles, by which the shades
40
45
and. properties of the 'dyestu?s'obtained are I
changed.
I'claim:
lfThe monoazo'dyestu?s' of the general form
50
ula:
is when" dry a lemon-yellow" powder,-soluble in
water, dyeing wool and silk bright‘ greenish yellow
x-om
shades of very good levelling power and fastto
Y— CH a
55 washing and light.
Example 5
20.6 parts of 1-(N-acetyl-sec-butylamino) -4
aminobenzene are diazotized in the usual manner
and the diazo solution obtained is allowed to run
60 into a solution of 36 parts of l-benzdylamino-S
naphthol-‘l-sulfonic acid containing an excess of
sodium acetate. When the combination iscom
plete the dyestuff formed of the formula:
65
acyl
l
2
65
wherein ‘X and Y stand for 'members selected
from the groupv consisting of hydrogen and
methyl; acyl stands for‘ an acyl radicle of the-ali
phatic 'and'benzene'seriesi Z stands-for a'member
selected ‘from the group consisting of hydrogen 60
and —SOxH, and R means- the radicle of a cou
pling component,vwhich dyestuffs yield on ?bers,
especially wool‘ and-silk,- clear‘ yellow to yellowish
red shades of good fastness properties'and’ of very
good levelling-power.
-
~2. The-monoazo dyestu? of the formula:
you lTIH-COKJH:
70
is isolated and dried.
It is a brick-red powder,
soluble in water, dyeing wool and silkbright yel
lowish red shades of‘ very good levelling‘ power
= and. good fastness especially .to light.
50
65
3
2,133,439
which dyestu? represents a dark red powder,
soluble in water, dyeing wool and silk bright
bluish red shades of good levelling power and
good fastness to fulling, light, seawater and per
5 spiration.
3. The monoazo dyestu? of the formula:
HIC
10
H10
\
/CH—I?'00
N=N—?-—(|Z|LCH2
110.0
N
\ /
CHI
OH
10
NH-CO
N
01
15
greenish yellow shades of very good levelling
power and fast to washing and light.
v4. The monoazo dyestu? of the formula:
Hogs
which dyestuff represents a lemon-yellow powder,
soluble in water, dyeing wool and silk bright
which dyestu?‘ represents a brick-red powder,
soluble in water, dyeing wool and silk bright yel
lowish red shades of very good levelling power
and good fastness especially to light.
RICHARD FLEISCHHAUER.
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