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Патент USA US3086016

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United
: res
tent
*
1
3,086,006
Patented Apr. 16., 1963
2
kylbenzene-S-sulfonic acid amides, 1-amino-2-alkoxyben
3,086,006
zene-5~carboxylic acid amides or l-amino-Z-alkoxybem,
zene-S-sulfonic said amides.
WATER-INSOLUBLE MONOAZO-D‘YESTUFFS AND
PROCESS FOR THEIR MANUFACTURE
Konrad Lt'ihe and Joachim Ribka, Offenbach am Main,
Germany, assignors to Farbwerke Hoechst Aktieu
gesellschaft vormals Meister Lucius 8; Briining, Frank
furt am Main, Germany, a corporation of Germany
No Drawing. Filed Jan. 23, 1961, Ser. No. 83,945
The l-(2’,3'-l1ydroxynaphthoylamino)-4-benzoylamino~
benzenes of the indicated formula which are used as cou—
pling components in the process of the present invention
are easily accessible ‘by known methods, for example by
reacting 2,3-hydroxynaphthoic acid with the correspond
Claims priority, application Germany July 2, 1960
6 Claims. (Cl. 260-204)
The present invention relates to new water-insoluble
monoazo-dyestuffs and to a process for their manufac
ture; more particularly it relates to Water-insoluble mono
ing 1-amino-4abenzoylaminobenzenes in a suitable solvent
10 such, for example, as xylene, chlorobenzene, toluene or
pyridine, in the presence of a condensation agent such,
for example, as phosphorus trichloride.
The dyestuffs can be prepared by known methods, for
azo-dyestu?’s of the following formula
example by coupling the diazonium compounds with the
15 ,coupling components in an aqueous medium in the pres
ence of a wetting or dispersing agent.
‘
The dyestuffs obtained by the present processare water
insolu-ble pigments which are distinguished by a good
fastness to. solvents. They are. suitable for the preparation
of colored lacquers or lake formers, for coloring solu
tions or products of acetylcellulose, nitrocellulose, nat
Xi?
ural resins or synthetic resins such as polymerisation or
-on
condensation resins, for example, aminoplasts, pheno
plasts, and of polystyrene, polyole?ns, for example, poly
25, ethylene or polypropylene, polyacrycl compounds, poly
R1
vinyl compounds, for example polyvinyl chloride or poly
0 o-nnOavn-o o-onr5
1'1.
vinyl acetate, rubber, casein or silicone resins. They are
further suitable for pigment printing on a substratum,
especially on a textile ?ber, and also on two dimensional
structures such as paper.
‘
'
‘
l
The new dyestuffs can also be used for other purposes,
wherein X, R1 and R2 represent a hydrogen atom, a halo
for example, in ?nely divided form vfor coloring rayon
gen atom, an alkyl or alkoxy group, and Y stands for the
of viscose or cellulose ethers and cellulose esters, poly
carbonyl or sulfonyl group.
amides or polyurethanes in‘ the spinning solution or for
We have found that valuable, water-insoluble monozo 35 the coloration of paper.
dyestuffs are obtained by coupling the diazonium com
In comparison with the water-insoluble monoazo-dye
pounds of amines of the general formula
stuffs of similar compositions which are known from Ger
man Patent 673,082, the dyestuffs obtained by the present
‘ process are distinguished by a better fastness to solvents.
in
40
The following example serves to illustrate the invention
but it is not intended to limit it thereto, the parts being
by weight unless otherwise stated, and the relationship of
parts by weight to parts by volume being the same as
45
Y-NH:
that of the kilogram to the liter.
.
Eatample
wherein X represents hydrogen, a halogen atom, an alkyl
17.1 parts of 1~amino-2-chlorobenzene-S-carboxylic
or alkoxy group and Y stands for a CO or S02 group,
acid amide are dissolved in the hot with 50 parts by vol
ume of 5, N hydrochloric acid and 175 parts by volume
of water and, after the addition of ice, the solution is
diazotized at 5° C. with 20 parts by volume of a 5 N solu
tion of sodium nitrite. The diazo solution is clari?ed
and united at 50° C. with an aqueous suspension of 21.7
with coupling components of the general formula
40H
I'll
55
parts of 1-(2',3'—hydroxynaphthoylamino)~2-methyl -4#
benzoylaminobenzene which is prepared by dissolving this
compound in dilute sodium hydroxide solution and pre
cipitation with glacial acetic acid in the presence of a re
action product from about 20 mols of ethylene oxide and
wherein R1 and R2 represent hydrogen, a halogen atom, 60 1 mol 'of octadecyl alcohol. The dyestu? separated after
I
R2
an alkyl or alkoxy group.
completion of the coupling is filtered with suction, Washed
As diazo components there are preferably used in the
process of the present invention meta- and para-amino
benzene-sulfonic acid amides or meta- and para-amino
and dried. It is an orange-red powder.
benzene-carboxylic acid amides, for example l-aminoben
zene-3-carboxy1ic acid amide or 1-aminobenzene-4-car
boxylic acid amide, or 1-aminobenzene-3-sulfonic acid
_
The nitrocellulose lacquers produced with this dyestuff
yield a yellowish-red lacquer ?nish possessing a good fast
By incorporating the dyestuft in
65 ness to overspraying.
polyvinyl chloride, a yellowish-red coloration possessing
a very good fastness to bleeding is obtained.
In the following table further components are listed
which can be used in the process of the invention, and the
70
no-2-halogenbenzene-S-sulfonic acid amides, l-amino-Z
tints produced by forming the monoazo-dyestu?s from
alkylbenzene-S-carboxylic acid amides or l-amino-Z-al
these components in substance.
amide or l-aminobeneZene-4-sulfonic acid amide, l-ami
no-2-halogenbenzene-S-carboxylic acid amides or l-ami
3,086,006
6
4. The water-insoluble monoazo-dyestu? having the
formula
6. The water-insoluble monoazo-dyestu? having the
formula
-0 0-NHr
5
—CO-—NH2
CHaO
I
CHaO
N
1111
N
‘
10
II
N
OH
1
-OH
_o O--NHQ~NH—OOO
H]
5. The water-insoluble m-onoazo-dyestuff having the
formula
-G0—NH;
—0 O-NH-
15
01
@ NH-O 00
References Cited in the ?le of this patent
20
01
UNITED STATES PATENTS
2,025,582
2,111,890
Fischer ______ _-_ ______ __ Dec. 24, 1935
I Fischer ______________ __ Mar. 22, 1938
N
2,186,226
Zerweck et a1 ___________ __ I an. 9, 1940
ll,
2,262,464
Marriott et a1 _________ __ Nov. 11, 1941
25
2,742,459
2,899,421
Fischer ______________ __ Apr. 17, 1956
Fischer ______________ __ Aug. 11, 1959
'30
818,675
France ________________ __ Oct.1,1937
_OO_NH©_NH_OOC>
é
H
FOREIGN PATENTS
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