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Патент USA US2136757

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Patented Nov. 15, 1938
2,136,757 I
UNITED STATES’ PATENT oI-jFlcE
AFTER-TREATMENT 0F DYEINGS ON CEL
-
LULOSIO FIBERS
Hans Boos, LeverkuseniL 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. 25,182. In Germany June 29, 1934
16 Claims. (Cl. 8-46)
This invention relates to a process for the im
provement of the fastness to washing of dyeings
on cellulosic ?bers with substantive dyestuffs and
to the improved dyeings obtained by this process.
In accordance with the present invention the
3-carboxylic acid, saiddyestu? correspondingin its free state to the following formula:—
‘
‘
coon
SOaH
v
lhN
,
fastness to washing of dyeings on cellulosic ?bers
with substantive dyestuffs containing at least once
the grouping
'
0
COOH
10
10
wherein R‘ and R’ stand for aromatic radicals, is
improved by aftertreating the same in the‘man
ner known per so with diazo compounds of the
NH:
10 grams of the dyed cotton are introduced for '
about half an hour into a bath containing 0.3 '
aromatic series. For the purpose of the present , gram of diazotized para-nitraniline, said bath be
2” invention there come into consideration quite
generally those bases as‘ are used in the manu
facture of ice colors, 1. e. bases containing no sub
stltuents inducing solubility in water, especially
of the benzene series, such as anisidine, para
25 nitro-ortho-anisidine and, ?rst of all, nitrani
lines. The process is carried out by introducing
the ?ber dyed with a dyestu? of the kind above
identi?ed into a diazo solution prepared in the
,usual manner and in which the mineral acid has
been neutralized, for example, by adding sodium
ing prepared by diazotizing in the usual manner
para-‘nitraniline with hydrochloric acid ; and
sodium nitrite and neutralizing the mineral acid
by theaddition of sodium acetate. By this after
treatment a reddish-yellow shade is obtained of
very good fastness to light and dischargeability in a
the neutral and alkaline processes.
I
Example 2
'
1
Cotton is dyed from a Glauber’s salt-soda both
with the dyestu? obtainable by coupling diazo- '
tized para-nitrobenzoyl-para-phenylenediamlne
acetate, for about half an hour at room tempera
, ture, rinsing the ?ber, soaping the samepin a
with i-phenyl-5-pyrazolone-3-carboxyl1c acid, re
boiling bath, again rinsing and drying. By this
aftertreatment the i'astness to washing is consid
35 erably improved; further, the dyeings possess a
better fastness to light than dyeings with analo
gously constituteddyestu?s produced by other
tizing, coupling with 1-(meta-nitrop'henyD-5
pyrazolone-3-carboxylic acid and reducing the
40
ducing the nitro group to the amino group, diazo-~ '
nitro group, said dyestuii corresponding to the
following formula:--
,
_
methods, and, moreover,‘ they may have a very
goodrdischargeability with a neutral or alkaline
reacting discharge paste.
.
,
coon
v
The following examplesmill illustrate the in
vention without, however, restricting it thereto?
45
Example 1
Cotton is dyed from a Glauber’s salt-soda-bath
with the reduced dyestu? from one molecular
proportion of para-laminoben'zoyl-para-amino- =
phenylurea-disuli'onic acid and 2 molecular pro
w'portions oi’ 1-‘-(meta-nitrophenyl) -5-pyrazolcne
E
,
coon
(gr-N
was 1
I
'
,LQ
.éa.
‘NB
_
2
2,186,757
The orange dyeing thus obtained is aftertreated
with para-nitraniline and yields a clear yellow
orange shade exhibiting properties‘ similar to
those of the aftertreated dyeing of Example 1.
nitro group,_which dyestuif corresponds to the
following formula:--
Example 3
Cotton is dyed from a Glauber’s salt-soda-bath o
with a dyestu? obtainable by diazotizing acetyl
10 para-phenylene diamine, coupling with salicylic
acid, saponifying the acetylamino group, condens
ing with para-nitro-benzoylchloride, reducing
the nitro group to the amino group, diazotizlng
and coupling with 1-(meta-aminophenyD-5
15 pyramlone-S-carboxylic acid, which dyestu? cor
responds to the following formula:
The yellowishorange dyeing is aftertreated with
diazotized para-nitraniline.
coon
20
N:
Thus an orange
dyeing is obtained exhibiting properties similar
to those of the aftertreated dyeing of Example 2.
011'
20
' Example 5
Cotton is dyed in the usual manner from a
_
25
NH-C
Glauber's salt-soda-bath with the dyestuif ob
coon
/ C:
N=N-—-Ol\1
tained by diazotizing ortho-amino-benzoic acid
and coupling with para-aminobenzoy1-2-amino- 25
5-naphthol-7-sulfonic acid, diazotizing and
coupling with l-(meta-aminodiphenyl) -5-pyraz
.
o1one-3-carboxylic acid, which dyestu?? corre
sponds to the following formula:
NH,
30
H0:
~
‘
coon
The yellow dyeing thus obtained is attertreated
40 with diazotized para-nitraniline. It is of a
somewhat more greenish shade than that of Ex
ample 1, exhibits a better fastness to light and
has otherwise similar properties.
/
NH-COO-N=N—CE I
‘
When using in the above example instead ‘of
'45 the 1- (meta-aminophenyl) -5-pyrazolone-3-car
n
NH’
An orange dyeing is thus obtained which becomes
somewhat more yellowish after the aitertreat-' 40
ment with diazotized para-nitraniline. It is dis
tinguished by an excellent clarity and fastness
to light combined with a good neutral and alka
line dischargeability.
~
boxylic acid the l-(para-aminophenyl) -5-pyraz
olone-3-carboxylic acid and aftertreating in the
usual manner with diazotized para-nitraniline,
,
brownish-yellow shades are obtained of an espe
50 cially good neutral .or alkaline dischargeability.
When using in the above example for the alter
11018
I110
'
46
Example 6
Cotton is dyed in the usual manner from a
Glauber's salt-soda-bath with the dyestu? from
diazotized meta-aminobenzoyl-dehydro-thiotolui
dine sulfonic acid and 1-(meta-aminophenyl)-5-_ 50
pyrazolone-3-carboxylic acid of the formula:
N\
\ 900mg;
C O OH
(',=N 1
55
NHg
treatment instead of the diazotized para-nitrani
The dyeing obtained is similar to that obtained
line the i-nitro-ortho-anisidine or 5-nitro-ortho
according to Example 3 and possesses similar
properties after the aftertreatment with diazo
tized bases.
‘ anisidine
(OCHJ=1) , somewhat more ‘reddish
shades are obtained.
I claim:--
Example 4_
Viscose silk is dyed from a Glauber’s salt-soda-v
70 bath'with the dyestuil obtained by coupling one
molecular proportion of tetrazotizedpara-amino
. ben'zyl-para-phenylene-diamine, one molecular
proportion of ortho-cresotinic acid and one
molecular proportion of 1- (meta-nitrophenyl) -5
75- pyrazolone-(i-carboxylic acid, and reducing the
'
’
1. The process which comprises aitertreating
cellulosic ?bers which have been dyed with a
substantive dyestui! containing at least once the
grouping
-
‘
-
coon
O=N
60
6 5.
3
2,136,757
wherein R and R’ stand for aromatic radicals,
with a diazo compound of an aromatic amine
free from a group-inducing solubility in water.
2. The process as claimed in claim 1, in which
the ?bers are aftertreated with a diazotized
nitraniline.
and‘ R" stands for an aryl radical free from a
group inducing solubility in water.
"
10. Cellulosic ?bers dyed with a dyestuff con
taining at least once the grouping: .
‘
3. The process as claimed in claim 1, in which
the ?bers are aftertreated with diazotized para
nitraniline.
4. The process which comprises aftertreating
10
cellulosic ?bers which have been dyed with a
substantive dyestuff of the formula:-—
10
|
NO:
wherein R and R’ stand for aromatic radicals.
11. Cellulosic ?bers dyed with a dyestu?z‘ con
taining at least once the grouping:
15
15
20 wherein R and R’ stand for aromatic radicals
and R2 stands for an aromatic radical which may
contain an azo group, with a diazo compound of
an aromatic amine free from a-group inducing
solubility in water.
5. The process as claimed in claim 4, in which
20
wherein R and R’ stand for aromatic radicals.
12. Cellulosic ?bers dyed with a dyestuff of the
formula:
v
I
25
the ?bers are aftertreated with a diazotized
nitraniline.
6. The process as claimed in claim 4, in which
the ?bers are aftertreated with diazotized para- _
30
30 nitraniline.
7. The process which comprises aftertreating '
cellulosic ?bers which have been dyed with the
dyestu? of the formula:—
"
R” stands for an aryl radical free from a group‘
inducing solubility in water, and R'” stands for
35
35
‘NE,
40
40
45
NH:
with diazotized para-nitraniline.
8. The process which comprises aftertreating
5 O cellulosic ?bers which have been dyed with the
dyestuff of the formula:--
'
an aromatic radical which may contain an azo
group.
,
13. Cellulosic ?bers dyed with a dyestu? of the 50
formula:
55
55
1110:
wherein R and R’ stand for aromatic radicals 60'
and R'” stands for an aryl radical which may
60
contain an azo group.
'
14. Cellulosic ?bers dyed with a dyestu? of the
formula:
65
,
with diazotized para-nitraniline.
65
9. Cellulosic ?bers dyed with a dyestu? con
taining at least once the grouping:
70
'
'
coon
70
c=N
/
-Nn—co-R-N=_N—cn
’
c-N-R'~Nn-N=N—R"
0
wherein R and R’ stand for aromatic radicals
wherein R and R'stand for aromatic radicals
and R’” stands for an aryl radical which may
contain an azo group.
'
v 4
2,130,757
15. Cellulosic ?bers dyed with the dyestu? of the formula:
.
80:11
00011
5
No,
E—N
00
$003.’
10
C=N
10
NHQNH~0 o-Qnen-cé ’
S 0111
g _CNE—N=NONO :
15
15
16. Cellulosic ?bers dyed with the dyestu?' 01 the formula:
c0011
20
COOH
25
30
HANS R008.
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