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Патент USA US2129964

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2,129,964
Patented Sept. 13, 1938
UNITED STATES v"Parr-zen" OFFICE
2,129,964
Azo DYEST‘UFFS'
Hans Boos, Levérkusen-I.‘ G.-Werk, Germany, as
signor to General’ Aniline Works, Inc., New
York, N. Y., a corporation of Delaware
No Drawing. Application June 5, 1935, Serial
No. 25,179. In Germany June 21, 1934
:3 Claims.
D
(Cl. 260-160)
The present invention relates to new substan
tive azo dyestuffs.
I have found that new and valuble cotton dye
stuffs can be obtained by combining l-aminoaryl
5-pyrazolone-3-carboxylic acids which may bear
any substituents in the aryl nucleus, such as halo
gen, alkyl, alkoxy, the sulfonic acid group, the
carboxylic acid group, and the like, with the diazo
benzoyl) -aminophenylurea - 3,3’ - disulfonic acid
compounds obtainable from the aminobenzoyl
amino compounds including the aminobenzoyl~
amino-benzoylamino compounds derived from di
amino diphenylurea sulfonic acids, diamino stil
bene sulfonic acids and dehydrothiotoluidine and
its homologues, such as dehydrothioxylidine.
azolone-3-carboxylic acid containing 56 grams of
are dissolved in 2 litres of water and 11 grams of
sodium carbonate, 13.8 grams of sodium nitrite
are added thereto, and‘ the solution is poured into
a mixture of 56 ccs. of 10-N hydrochloric acid,
some water and ice. The diazotization is soon
complete, and the mixture is introduced into a
solution of 50 grams of 1-m-nitrophenyl-5-pyr
sodium carbonate. The formation of the dye 1O
stu? proceeds quickly, the dyestu? formed is re
duced with sodium sul?de .at '70-80° C. and after
this isolated in the usual manner and dried. In its
free state it corresponds to the following formula:
15
00011
S 0:11
'
I
/o \
NHI
NH-ONMGNe-e r
GHQ'
CO
COOH
NH:
25
TO U!
CO-———N
S 03H
As diazotization components suitable for the
30 purpose of the present invention there are men
tioned by way of example di- (0-, m-, or p-amino
benzoyl) -diaminodiphenylureadisulfonic acid, di
(aminobenzoylaminobenzoyl) - diaminodiphenyl
ureadisulfonic acid.
My new dyestuffs are in form of their alkali
metal salts generally yellow to orange powders
dyeing the vegetable ?ber generally yellow to
orange shades.
The dyeings obtained with my new dyestu?s
40 can be after-treated with formaldehyde in the
usual manner, whereby their fastness to washing
is considerably improved. Further the new dye
it dyes cotton a reddish yellow which can be dis
charged to a pure white both with a neutral and 30
an alkaline reacting discharge paste. When
diazotized and developed with l-phenyl-IS-meth
' yl-5-pyrazolone, a yellow fast to washing, with 18
naphthol an orange fast to washing is obtained.
It may be mentioned that the non-diazotized 3-5
dyeings can be aftertreated with formaldehyde,
whereby the fastness to washing is remarkably
improved without unfavorably influencing the dis
chargeability. -
I claim:
1. Azodyestuffs after the general formula
40
SOaH
stuffs can be diazotized in substance or on the
45
?ber and developed with the usual developers.
Compared with the known dyestu?s which are
distinguished from my new dyestuffs by contain
ing as coupling component l-aminophenyl-3
methyl-5-pyrazolone instead of a 1-aryl-5-pyr
azo1one-3-carboxylic acid the new dyestuffs yield
S 0311
somewhat more reddish shades of an improved
dischargeability both with a neutral and alkaline
wherein Py stands for the radical of a l-meta
discharge paste.
aminophenyl - 5 - pyrazolone - 3 - carboxylic acid,
‘
The invention is illustrated by the following
examples, without being limited thereto:
55
45
Example 1.—64 grams of 4,4’-(di-p-amin0~
dyeing the vegetable ?ber yellow shades which can
be discharged to a pure white both with a neutral
and an alkaline reacting discharge paste.
50
2
'
‘
2,129,964
2. The dyestu? having in the free state the following formula:
s 03H
$005
5
NH
NH—C 0-
/
stands for a radical of an aminobenzoyl compound
of the gI'Oup consisting of aminobenzoyl diamino
/°\
N=N—(|3H III ,
s
NH;
I
5
c 0 -—-N—
00
1
'
1O
10
coon
dyeing cotton reddish yellow shades which, when
diphenylul‘ea ‘sulphonic acids and aminobenzoyl
diazotized on the ?ber and developed with l-
diaminostilbene sulphonic acids, and R’ means 1
phenyl - 3 - methyl - 5 - pyrazolone, yield
meta—amin0pheny1- 5 —pyrazo1one - 3 — carboxylic
shades fast to washing.
20
yellow
_
acid, dyeing the vegetable ?ber generally yellow to
3. Disazodyestu?s of the formula 7
>
orange shades which can be aftertreated with 20
N:N__R,
R\
'
.
N=N—R’
25 wherein
N:
R
formaldehyde or diazotized and developed.
/
\
HANS ROOS.
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