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Патент USA US2120754

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2,120,754
Patented June 14, 1938
UNITED STATES
PATENT OFFICE
2,120,754
D‘ISAZO- DYESTUFFS ANDl PRO OES S FOR
THEIR PREPARATION
‘Adolf Krebser, Riehen, near Basel, Switzerland,
assignor to the ?rm J. R. Geigy A. G., Basel,
Switzerland
No Drawing. Application April 20, 1937, Serial
No. 138,066. In Germany April 29, 1936
8 Claims. (Cl. 260-83)
In British speci?cation No. 24,527 of 1897 there
is described the manufacture of black disazo-dye
stu?s by combining a diazotized para-aminodi
phenylamine sulphonic acid or a homologue
5 thereof with a-naphthylamine and then re-diazo
tizing the aminoazo-compound thus produced and
coupling it with a naphthol or a sulphonic acid
thereof. These dyestuffs are known under the
name of “Nerol” (C01. Ind. No. 304).
According to the present invention, disazo-dye
stuffs with unexpected and completely new qual
ities are obtained when the aforesaid manufac
ture is modi?ed by using 2-naphthol-4-sulphonic
acid as the ?nal azo-component instead of those
15
commonly used, namely 2-naphthol-6-sulphonic
acid and 1-naphtho1-4- and -5-sulphonio acids.
The new disazo-dyestuffs are suited for dye
ing wool and silk; the dyeings do not bronze,
even in deep shades, a property which is of great
importance to the dyer. In this respect they dif
fer from the known dyestuffs containing iso
meric naphthol-sulphonic acids as ?nal compo
nents. This di?erence is very unexpected and
surprising.
25
In addition to the new property above described,
the disazo-dyestuffs of the present invention have
a better af?nity for wool in a neutral dye bath and
are remarkably fast towards 802. They have a
pronounced greenish shade which is greatly ap
preciated for deep black dyeings.
The following example illustrates the inven
tion:
28.6 kilos of the sodium salt of para-aminodi
phenylamine—ortho-sulphonic acid are diazotized
at 0° C. By means of 7 kilos of sodium nitrite
and 32 kilos of hydrochloric acid of 30 per cent.
strength. The diazonium compound which has
partially separated is then added to an aqueous
suspension of 18 kilos of a-naphthylamine hydro
40 chloride containing 14.3 kilos of u-naphthylamine
and the mineral acid is slowly neutralized by ad
dition of '75 kilos of a sodium acetate solution of
20 per cent. strength. The formation of the
monoazo-dyestuff is completed by addition of 8
45 kilos of anhydrous sodium carbonate in 30 litres
of water. The product which has separated is
?ltered and converted into the sodium salt with
line throughout with 25 kilos of anhydrous so
dium carbonate. Stirring is continued for sev
eral hours and the dyestu? is then salted out with
common salt, ?ltered, pressed and dried. It is
a black powder which is soluble in water to a
greenish-blue solution and in concentrated sul
phuric acid to a greenish-grey solution.
If in the above example the para-aminodiphen
ylamine-ortho-sulphonic acid is replaced by an
isomeric or homologous compound or by a sub
stitution product such as para-aminophenyl
para’-tolylamine-ortho-sulphonic
acid,’ para
amino-para’ - ethoxy-diphenylamine-ortho - sul
phonic acid and so on, there are obtained black
disazo-dyestuffs with similar properties.
What I claim is:
1. A process of producing disazo-dyestu?s
which comprises combining one mol. of a diazo
tized
p-aminodiphenyl - amine - monosulphonic
acid with 1 mol. of a-naphthylamine, diazotizing 20
the thus produced compound and combining
same with 1 mol. of Z-naphthol-‘l-sulphonic acid.
2. A process of producing disazo-dyestuffs
which comprises combining 1 mol. of diazotized
p-aminodiphenyl - amine-ortho - sulphonic
acid 25
with. 1 mol. of a-naphthylamine, diazotizing the
thus produced compound and combining same
with 1 mol. of 2-naphthol-4-sulphonic acid.
3. A process of producing disazo-dyestuffs
which comprises combining 1 mol. of diazotized 30
p — aminophenyl-p' - tolylamine-ortho - sulphonic
acid with 1 mol. of u-naphthylamine, diazotizing
the thus produced compound and combining same
with 1 mol. of 2-naphthol-4-sulphonic acid.
35
4. A process of producing disazo-dyestuffs
Which comprises combining 1 mol. of diazotized
p-amino-p’ - ethoxy - diphenylamine - ortho-sul
phonic acid with 1 mol. of a-naphthylamine, di
azotizing the thus produced compound and com
bining same with 1 mol. of 2-naphthol-4-sul
phonic
acid.
'
40
,
5. Disazodyestuffs of the formula of the dye
stuff acids
45
(‘)H
the requisite quantity of caustic soda lye. After
addition of a solution of 6.9 kilos of sodium ni
50 trite, the whole is allowed to run slowly at 0-5° C.
50
into '70 kilos of hydrochloric acid of 30 per cent.
strength diluted. with ice and water. The sparing
wherein A represents the radical of a p-aminodi
ly soluble blue-black diazonium compound thus
black powders, soluble in water to a greenish-blue
formed is then added to a solution of 22.4 kilos
55 of 2-naphthol-4-sulphonic acid maintained alka
phenylamine-sulphonic acid, said dyestu?'s being
solution and dyeing wool and silk black shades’
which do not bronze even in deep shades.
‘
2
2,120,754
6. The disazodyestu? of the formula of the dye
stu? acid
10 said dyestuff being a black powder soluble in water
to a greenish-blue solution and in concentrated
wool and silk black shades which do not bronze
even in deep shades.
8. The disazodyestuff of the formula of the dye
stuff acid
10
on
‘
15
HnCHOONHQN=N~
S 0:11
N=
803E
sulphuric acid to a greenish-grey solution, dye-
said dyestuff beingablack powder solubleinwater
ing wool and silk black shades which do not
bronze even in deep shades.
'7. The disazodyestu? of the formula of the dye
stu? acid
to a greenish-blue solution and in concentrated
15
sulphuric acid to a greenish-grey solution, dye- *
ing Wool and silk black shades which do not bronze
even in deep shades.
OH
25
30
l
25
said dyestu? being a black powder soluble in water
to a greenish-blue solution and in concentrated
sulphuric acid to a greenish-grey solution, dyeing
ADOLF KREBSER.
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