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Патент USA US2134038

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Patented Oct. 25, 1938
‘ ‘UNITED=STATES PATENT.
ICE 5 ‘
MoNoAz0 DYESTUFFS » '
Richard 'Fleischhauer, F‘rankfort~on-the4Main; Fechenheim, Germany, assig'nor' to General > w
v Aniline iWo'rks, Inc.,'_New York,; N. Y., aucoré "
_' g’ poration _ of ; Delaware
narrating‘. ‘Application October 16, 1936,, se
rial No. 105,931. In Germany October 7:22,
1935
.
.
3 Claims.
This invention relates to valuable new mono
azodyestu?‘s, more particularly to those of the
general formula:
i0
wherein X stands for a member selectedfrom
the group consisting of hydrogen, alkyl, alkoxy».
cyclohexyl and phenyl‘ andR stands for a mono
cyclic radicle of the benzene series. .,
,7 I _‘
Y
.
The new dyestuifs are obtained by combining
:15
the diazo compounds of aromatic amines of the
generalformula;
'
‘
'
(01." 266L921. ‘ '
When the combination is performed in ‘the pres
ence of another acid-binding agent such as for
example sodium bicarbonate dyestuifs are ob
tained which yield somewhat more reddish brown
shades of similar properties.
Instead of the above diazo component there may
be used in an analogous manner other similar
compounds such as for example:
N- (4-aminophenyl) -N-methoxyacety1-aminoa
cetic acid,‘ N-(é-amiriophenyl) - N - carbethoxy
it
aminoacetic. acid; N-(4-aminopheny1) -N-chloro
acetyl-aminoacetic acid; N-(4-aminophenyl) éNphenoxyacetylearninoacetic acid; " N-(-4-amino
phenyl) -N-benzoyl-aminoacetic acid, N-(4-ami
nophenyl) -N-hexahydrobenzoyl—aminoac'etic ac
' id, N-(‘l-aminophenyl) -N-propionyl-aminoacetic
acid, N- (4-amino-2-methylphenyl) -N-acetyl-am
inoacetic acid or substituted derivatives thereof. .
|
COX
(wherein X has the above signi?cation) with 2
By employing the corresponding amounts of these
diazoilcomponents.instea'diof the above said N
(4 >— aminophenyl) - N .- acetyl - aminoacetic ‘ acid
aryl-amino-8-naphthol-6-sulfonic acids.’
,
brown dyestuffs areobtained of quite analogous
' The diazo components employed for themanu
facture of the dyestuffs of this invention may be‘ properties and partly distinguished by an'vin
prepared for example in an analogous manner to creased fastness to light or by deeper brown
the methods described in German Patents No. shades. Thus the dyestu? prepared by starting 25
152,012 and No. 154,556. Or they may be pre " from N- (é-aminophenyl) :N-benzoyl-aminoacetic
pared by starting from nitro-aryl-glycines which I acid yields deeper brown shadesthan the dyestuff
are acylated and reduced.
.
The new dyestuffs yield on animal ?bers brown
shades of good fastness properties. They are dis
tinguished from similar brown dyestuffs by a very
good solubility and partly by a much better fast
9
prepared by starting from N-(4-aminophenyD
N-acetyl-aminoacetic acid.
Example 2
20.8 parts of N-(‘i-aminophenyl) -N-acetylami
ness to ironing.
The following examples illustrate, but do not
noacetic acid are diazotized in the usual manner
limit the invention, the parts being by weight.
35 parts of 2- (4'-vmethoxy-phenylamino) ~8-naph
Example 1
and the diazo solution obtained is combined with
35
thol-?-sulfonic acid in the presence of an excess
of sodium acetate. The dyestu?" formed is iso
lated
and dried. It forms a dark powder, easily
inc-acetic acid are diazotized in the usual manner '
4D and the diazo solution obtained is combined with soluble in water, dyeing wool deep violet-tinged
brown shades of quite similar properties as the
35 parts of 2-(4’-methoxyphenylamino) -8-naph
20.8 parts of N-(4-aminophenyl) -N-acetyl-am
thol-6-sulfonic acid in the presence of an excess
of sodium carbonate. The dyestu? formed of the
45 formula:
dyestuif obtained according to Example 1, but of
a somewhat increased fastness to light.
The diiference between the new product and
the dyestu? obtained according to Example 1
45
50
COCHa
HOaS/
is isolated by the addition of an acid and of sodi
um chloride. It forms when dry a dark powder,
very easily soluble in water, dyeing wool deep full
brown shades of good fastness to ironing and
5 01 light and of good levelling power.
50
seems to be caused by the fact that a little amount
of another dyestu? is produced beside the dye
stu? the formula of which is given in Example 1,
whereby the combination probably takes place in
the 1-position of the coupling component. When 55
2,184,038
the amount of the sodium acetate employed is
varied, more or less of the byproduct is formed
and the properties of the dyestu? obtained may
be altered thereby.
Instead of the above coupling component there
may also be employed in the foregoing examples
2-arylamino-8-naphthol-6-sulionic acids which
dium chloride. It is when dry a dark powder.
soluble in water, dyeing wool and silk very deep
brown shades of good Iastness to ironing and of
good levelling power.
I claim:
1. The monoazo dyestu?s consisting substan
tially .0! products of the general formula:
OH
may contain further substituents in their aryl
radicle.
Such coupling components are for ex-v ‘ ‘ ~
'
10
ample:
'
NH-B.
(LO-X
Z-phenylamino 8-naphthol-6-sulfonic acid,_ 2
(2'- methyl-phenylamino) -8-naphtho1-6-sulfonic
acid, 2- (2’-methoxy-phenylamino) -8-- naphthol
H018
wherein X standsfor a member selected from the
6-sulfonic acid, 2-(2',4’-dimethoxy-phenylami-r group consistingof hydrogen, alkyl, alkoxy, cyclo
15
no) -8-naphthol-6-sulfonic acid, 2-(2’,5’—dime
thoxy-phenylamino)-8-naphthol-6<sulfonic acid,
2-(chloro-phenylamino) -8-naphthol # 6 -' sulfonic
20
acids, 2- (sulfo-phenylamino) -8-naphtho1-6-syul
fonic acids, z-(carboxy-phenylamino)é8-naph
thol-?-sulfonic acids.
'
15
hexyl and phenyl and R. stands for armonocyelic
‘radicle‘ of. the benzene series, which dyestuffs are
easily soluble in water and yield on animal ?bers
brown shades of good iastness properties.
2. A monoazo dyestu? consisting substantially 20
of a product of the formula:
'
H
NHOO on:
25
25
.HOIS
which dyestu? represents a dark powder, soluble
Ezamplevb‘ '
30
10
3000-011,
_
'in water, dyeing wool and silk very deep brown
> 19.4 parts of N-(4-aminophenyl) -N-.formy1-am— , shades of good fastness to ironing and of good lev
elling power.
30
I
inoacetic acid are diazotized in the usual manner ,'
3. A monoazo dyestu?.’ consisting substantially
and the diazo solution obtained is allowed to run
of
a product of the formula:
into a solution of 35 parts of 2- (4’—methoxy-phen
35
as
NHOO cm
COCH;
which dyestu? represents a dark powder, very
:10 ylamino)e8enaphthol-?-sulfonic acid containing easily soluble in water, dyeing wool deep full
an excess of sodium bicarbonate. When the com
bination is complete the dyestu? formed substan
tially consisting of a product of the formula:
brown shades of good fastness to light and iron
ing and of good levelling power.
45
OH
:15
so
is isolated by the addition of an acid and of so
40
RICHARD FLEISCHVHAUER.
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