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Патент USA US2109182

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2,109,182
Patented Feb. 22, 1938
V UNHTED
STATES
PATENT OFFICE
2,109,182
MONOAZO COMPOUNDS AND‘ THEIR PRO
DUCTION
Heinrich OhIendorf and Erich Baumann, D‘essau
in Anhalt, and Karl Holzach, Ludwigshafen
on-the-Rhine, Germany, assignors to Gen
eral Aniline Works, Inc., New York, N. Y., a cor
pcration of Delaware
N0 Drawing. Application March 31, 1934, Serial
No. 718,512. In Germany April 15, 1933
10 Claims. (Cl. 260—96)
This invention relates to the manufacture of
new unsulfonated azo dyes which are applicable
advantageously for dyeing cellulose esters, par
ticularly acetate arti?cial silk, by coupling a
5 diazotized amino compound of the general for
mula
'
X
for acetate arti?cial silk and dyes it a bluish
,
ring, at 25-30° 0., 20.7 parts of 2,6-dichloro-1
amino-4-nitr0benzene into nitrosyl sulfuric acid,
I
in which X is hydrogen, a nitro group or halo
gen and Y is hydrogen or halogen, with a ben
15 zene derivative capable of being coupled and of
the general formula
wherein B. may be an alkyl or hydroxyethyl
group and R’ a ?q-dihydroxypropyl group or a
'y-alkoxy-c-hydroxypropyl group and in the lat
ter case B may be hydrogen, inthis formula the
benzene nucleus may contain other substituents,
such as alkyl, alkoxy or halogen.
The new dyes have the same good capacity for
White discharge, fastness to light and other prop
erties as characterize the dyes described in U. S.
Patents No. 1,673,301 and No. 1,805,919, but sur
pass those dyes in the greater clearness of the
dyeings obtained with them as well as by their
CO bi greater capacity for being suspended and the
thoroughness with which they can be exhausted
from the bath.
In dyeing they are applied in aqueous suspen
[0 LI
sion with or without the addition of a colloid or
solvent.
10
made by adding 7 parts of sodium nitrite
‘to 130 parts of concentrated sulfuric acid,
and the mass is then strongly diluted by pour
ing it on ice. The ?ltered sulfuric acid solution
of the diazo compound is run into a cold solu
15,
tion of 22.5 parts of hydroxyethylwemethoxy-p
hydroxypropyl-aminobenzene in 800 parts of
water and 13 parts of hydrochloric acid of 23°
Bé. The acid is neutralized with caustic soda
solution until the coupling is completed. The 2O
dye dyes acetate arti?cial silk clear yellow brown
tints of very good fastness to light.
R,
7
The following examples illustrate the inven
tion, the parts being by weight:—
Example 1.—The diazo solution made in the
usual manner from 13.8 parts of 4-nitro-1
aminobenzene is run into a cold solution of 24.6
of
pling is complete. The dye has very good affinity
Earample 3.--A diazo solution is made by stir;
Y
parts
Bé. and 600 parts of Water, and the whole is
neutralized with sodium acetate until the cou
wine-red.
|
10
methyl-3 - (butyl ~16, 'y - dihydroxypropyl) ’ - amino
benzene in 20 parts of hydrochloric acid of 23°
3-chloro-1-(hydroxyethyl-p,'y-dihy
droxypropyD-aminobenzene in 18 parts of hy
drochloric acid of 23° Bé. and 600 parts of Water.
The acid is neutralized with sodium acetate up
50 to the end of the coupling. The dye obtained
dyes acetate arti?cial silk a ?ery yellowish red
of good fastness.
Example 2.—A diazo solution made in the
usual manner from 17.3 parts of 4-nitro-2'r
55 chloro-l-aminobenzene and 23.’? parts of 1
Example 4.-—A,diazo compound is prepared by
stirring ,19 parts of 2,4-dinitro-l-aminobenzene
into a nitrosyl sulfuric acid, made by introduc
ing 7 parts of sodium nitrite into 120 .parts of
sulfuric acid, and the mass is then’ diluted by
pouring it upon ice; the whole is now run into a
cold solution of 26.7 .parts of l-methyl-ll-meth
oXy - 3 » (butyl-cq — dihydroxypropyl) - aminoben
zone.
30
The acid is neutralized with sodium ace
tate until the coupling is complete. The dye
dyes acetate arti?cial silk violet tints.
The dye obtained in an analogous manner
from 22.6 parts of l-methyl-S-(hydroxyethyl
?,'y-dihydroxypropyl) -aminobenzene dyes acetate
arti?cial silk ruby red.
.
The dyes have a very good capacity for being
suspended and a good allinity in dyeing.
Example 5.--29 parts of G-bromo-ZA-dinitro
40
l-aminobenzene are stirred at 50-60° C. into ni
rosyl sulfuric acid prepared by introducing 7
parts of sodium nitrite into 120 parts of concen
trated sulfuric acid, and the mass is then strongly
diluted by pouring it upon ice. The sulfuric acid 45
solution of the diazo compound, if necessary
after ?ltration, is run into a cold solution of
252 parts of 1-methyl-3-(butyl-v-methoxy-?-hy
droxypropyl)~aminobenzene. The dye thus ob
tained dyes acetate arti?cial silk very clear red
dish blue of very good fastness.
If in this example there is used for the cou
pling a solution of 26.9 parts of 1-methyl-4- meth
oxy-3- (hydroxyethyl-v - methoxy - 5 - hydroxypro
pyl) -aminobenzene there is obtained a dye which 55
2,109,182
6. The dyes which correspond to the general
dyes acetate arti?cial silk a greener blue than
that yielded by the preceding dye.
formula
Example 6.—The diazo solution made from 29
parts of 6~bromo-2,4~dinitro-l-aminobenzene is
I
coupled with a solution of 22 parts of 3-_chloro-1
' /R
('y - methoxy - 5 -hydroxypropyl) -laminobenzene.
H2- CHOH- 01110 R’
The ?nished dye dyes acetate arti?cial silk red.
What we claim is:
1. The process which comprises diazotizing an
amine of the general formula
'
I.“
15
i
Y
in which Y is a member of the group consisting
of hydrogen and halogen, and coupling the diazo
compound with an amine of the benzene series 7
in which y is a member of the group consisting of
hydrogen and halogen, R. is a radicle of the group
consisting of alkyl and hydroxyethyl, R’is a.
member of the group consisting of hydrogen and.
alkyl and in which V and W are members of the
group consisting of hydrogen, alkyl, alkoxy and
halogen, said dyes being insoluble but emulsi? 15
able in water, and dyeing acetate silk clear fast
tints from yellow to blue.
7. The dyes which correspond to the general
formula
v
corresponding to the general formula
~
0H3
>
I
R
V
Br
JV
CHz-OHOIELCHzOR’
wherein'R is a radicle of the group consisting of
alkyl and‘hydroxyethyl, R’ is a member of the
group consisting of hydrogen and alkyl and in
which V and‘W are members of the group con
sisting of hydrogen, alkyl, alkoxy and halogen.
2. The process which comprises diazotizing 6
bromo-2,4-dinitraniline and coupling the diazo
10
in which w ‘is a member of the group consisting 25
of hydrogen, alkyl, alkoxy and halogen and R is a
member of the group consisting of alkyl and hy
droxyethyl, said dyes being insoluble but emul
si?able in water and dyeing acetate silk clear
,30
reddish blue to blue tints of good fastness.
8. The dye of the formula
Cl
compound with an amine of the benzene series
/CH2- CHr OH
of the general formula
\
(IJHa
R
VIV
CHz-GHOH-GHzOH
said dye dyeing acetate arti?cial silk a ?ery yel
lowish red of good properties of fastness.
9. The dye of the formula
CH2'CHOH'CH2OCH3
40
wherein W is a member of the group consisting
of hydrogen, alkyl, alkoxy and halogen and R is
CH2-CHOH-CH2-O OH;
a member of the group consisting of alkyl and
hydroxyethyl.
3. The process which comprises diazotizing 4
nitro-l-aminobenzene and coupling the diazo
compound with 3-chloro-1-(hydroxyethyl) 43W
50
‘ said dye dyeing acetate arti?cial silk a very clear
45
reddish blue of very good properties of fastness.
10. The dye of the formula
'
dihydroxypropyl) ~aminobenzene.
50
4. The process which comprises diazotizing 6
bromo-2,4-dinitro-l-aminobenzene and coupling
the diazo compound with 1-methyl-3-(butyl-y
methoxy-B-hydroxypropyl) -aminobenzene.
U! Si
5. The process which comprises diazotizing 6
bromo-ZA-dinitro-l-aminobenzene and coupling
the diazo compound with l-methyl-(l-methoxy-3
(hydroxyethyl-v-methoxy-p-hydroxypropyl) -am
inobenzene.
said dye dyeing‘ acetate arti?cial silk a very clear
55
blue of very good properties of iastness.
HEINRICH OHLENDORF.
'ERICH BAUMANN.
KARL HOLZACH.
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