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Патент USA US2055074

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2,055,074a
Patented ‘Sept. 22, 1936
i‘ unirnolasm'resi
. MoNoAzo DYESTI-IEFS
“ _' :Richard
‘ F‘echenhei“m,~
Fleischhauer,
Germany,
Frankfort-on-the-Maine
,assignor .to General _ _. '
Aniline Works, Inc., New
ration of Delaware
No Drawing. ‘Original application October ‘1,. f ‘
__l_§33',"serial No; 692,700.. Divided. and this‘. ap
plication April 30, 1935, Serial No.g19,,118.. In
Germany October 13, 1932;
“
‘ ' ‘
V‘ .7
4 Claims. (01. 260-92)
7 ‘The presentapplication' is“ a division- of ‘my?’ at:
phenyl-ether or‘ 2 - amino - 4' - methyl-diphenyl
plicat-ion‘Serial No; 692,790‘; ?led ()ctober '7', 1933,
ether or 2-amino-4-chlorordiphenyl-ether,"dye
and relating to monoazodyestu?s.
stu?s of similar properties are obtained.
f ‘
stuffs more particularly to those corresponding to
the general formula:
I
'
..
By replacing; theidiazo-cornponent by the equi
My present invention relates‘ to‘ monoazodye
r
valent amount of. 4‘-amino-diphenyl-ether-2-sul
ionic acidyared' dyestuff is obtained dyeing wool
equal shades of a very good fastness to light, full
ing and ‘perspiration;
‘
-
in i‘- —N
v
‘
'
7
z .
r11
'>
‘
naphthol'-6-_-sulfoni'c: acidi on-‘th'e: ‘urethane: of; the 10
2#amino-8-naphthoF6-sulfdnic acid may be used
10
o-phenyl
Y‘
In the same manner e..» g._ 2:-benzoyl-aminoi-8
7
as’ combining‘components.‘
S033‘
. it
‘
"
y
wherein Y means; hydrogen, alkyl. orrphenyl; R.
means acetyl or benzoyl or the urethane radicle
and wherein the, phenyl nucleicontain a‘member
of the group consisting-ofhydrogen, halogen, and
sulfonic
These acid.
dyestuffs;. are obtained
’
.. by combining
'
..
a
diazo compound of an aminodiphenylether with a
Examplev
.
H
‘
By using in Example 1, paragraph 3; instead
of 2-acetyl-amino-8#-naphthol1-6-sulfonic: acid the
same quantity of 2-acetyl-amino'-5'~naphtho1;-€I;
sulfonic acid, a brickL-red water-soluble dyestu? is
obtained. which corresponds to the following for
mula:
,
'1
on"
2- or 3- or‘i- acylamino-8-hydroxy-naphtha1ene
20
'
?-sulfonicacid: oithe formula;
on-
H
.25
B
8.0311
—-—N
\
30
Y
sén
wherein R and Y have the aforesaid signi?cation.
In order to further illustrate my invention the
following examples are given; but I wish it, how
ever, to be understood-that my invention is not
limited to the particular products or reaction
condition stated therein.
Example 1
18.5 parts of Z-amino-diphenylether are diazo
40 tized in the usual manner. The obtained diazo
solution is allowed to run while cooling into a
solution of 28.5 parts of 2-acetylamino-8-naph
thol-G-sulfonic acid containing an excess of sodi
um bicarbonate.
When developing is ?nished,
the dyestuff is isolated and dried. It forms a red
brown water-soluble powder corresponding to the
formula:
and dyes wool from an acid bath bright orange
shades of a very good fastness to light.
30
Still more yellowish dyestuffs of a similar
brightness may be obtained by using as diazo
components 4-amino-diphenyl-ether, 4-amino
diphenyl-ether - 2 - sulfonic acid, 4 - amino - di—
phenyl-ether-B-sulfonic acid, 2 -amino-diphenyl
ether-4-sulfonic acid and so on.
35
A dyestuff of similar properties is formed by
developing diazotized 4-amino-diphenyl-ether-2
sulfonic acid with 2-(2’, 5'-dichloro-benzoyl)
methyl-amino-5-naphthol-7-sulfonic acid.
40
Example 3
18.5 parts of 4-amino-diphenyl-ether are diazo
tized in the usual manner. The diazo-solution is
then allowed to run into a solution of 30 parts
of Z-(acetyl - methyl - amino) -8-naphtho1-6-sul
fonic acid containing the necessary amount of
sodium bicarbonate. When developing is ?n
ished the dyestuff is isolated. It forms a red
water-soluble powder which corresponds to the 50
50
following formula:
OH
/
N
CH3
.
80:11
55
55
SaH
and dyeing the animal ?ber bright equal red
shades.
60
'
‘
When using as diam-component 4-am1no-di
dyeing wool very equal bright red shades which
are fast to light.
2,055,074
By using as combining- components 2- (benz‘oyle member -' of the group {consistingg-ofzapetyl and
methyl-amino) --8-naphtho1-6-sulfonic acid 1 or 2
(acetyl-phenyl - amino) - 8 - naphthol-G-sulfonic.
benzoyl and wherein the phenyl nuclei contain a
_member of the group consisting of hydrogen,
acid or 2- (acetyl-cyclohexyl-amino) -8-naphthol-" ’ halogen, and sulfonic acid, which dyestuffs dye
6-sulfonic acid similar dyestuffs are obtainable. animal?bers orange to red shades of a- good
Example 4
- leveling power and frastness' to light.
2. The monoazodyestu? of the formula:
18.5 parts of 4-amino-diphenyl-ether ar‘e,di—' ' V
azotized as described in Example 1 and developed '
10 with a solution of 29 parts oil-acetyl-amino
5-naphthol-7-sulfonic acid inthe- presence of
sodium bicarbonate. The dyestuif .thus obtained
represents after isolating and'drying a brown
NHOOCH:
red water-soluble powder and corresponds to the 7
15 following formula:
'
which dyestu? forms a brick-red water-soluble
15
powder and dyes'wool from an acid. bath bright
orange shades of a very good fastness to light. v
3. The monoazodyestu? of- the formula:
‘20
5
on
I
'It dyes theanimal ?ber equalbright red shades.
' Verygood leveling bright red dyestuffs of very
-
20
-
7
CH:
OOON=N
I
.
‘
-N/
\
COCH:
25 good fastness qualities are. obtained by developing
the diazo-compound- of 2-amino-4-chloro-di
‘phenyl-ether 'or of 4-amino-diphenyl-ether-21
sulfonic acid respectively with Z-(acetyl-methyl
amino) -8-naphthol'-6-'sulfonic acid.
30.
SOIH
which dyestu? forms a red powder and dyes wool
very equal bright red shades fast to light.
4. The mono-azodyestu? of the formulaf
30
1.' The, mono-azodyestu?s corresponding to
the general formula:
'
'
25
~
.7 011711
35
35
which dyestuffs forms a brown-red powder and
dyes the animal ?ber equal bright red shades.
wherein Y means a member of the-group consist
ing of hydrogen, alkyl and phenyl, R means a
RICHARD FLEISCHHAUER.
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