DE181929C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

CLASS 12 q. GROUP

Patented in the German Empire on April 27, 1905.

It has been found that it is easy to get to those hitherto unknown ι - Arylamino - 8 - naphtolsulfosäuren gets when you get the i-amino-8-naphtholsulfonic acids 5 or their salts with aromatic amines heated in the presence of water.

This result is surprising, as it has not yet been possible to produce this valuable To obtain products, and in particular in the known method of heating with amines and hydrochloric acid amines only got resinous smear.

Of the class 22 method of patent 101286, this is the present in principle different. While according to that method for the preparation of nitroarylaminonaphthol sulfonic acids from aminonaphthol sulfonic acids and nitrated haloaryl derivatives, such as. B. Dinitrochlorobenzene, which by the entry of negative groups easily replaceable chlorine atom of the nitroaryl derivative / which itself does not contain an amino group, with a hydrogen atom of the amino group of the Aminonaphtholsulfonic acid is split off, the amino group reacts in the present case of the aromatic amine used with the amino group of aminonaphthol sulfonic acid, with cleavage of ammonia and formation of hitherto unknown i-arylamino-8-naphthol sulfonic acids. If you use z. B. dichloroaniline according to the present process, the two chlorine atoms remain, which are not here easily replaceable by the entry of negative groups, intact and one gets through Action of the two amino groups on one another with elimination of ammonia dichlorophenylaminonaphthol sulfoic acids.

The arylated aminonaphthol sulfonic acids obtained in this way are valuable intermediates for the production of dyes.

Example 1.

341 parts of i-amino-8-naphtol-3 · 6-disulfosaures sodium are heated with 200 parts of aniline and 1000 parts of water for 48 hours under pressure at 120 ^0th The excess aniline is then distilled off from the reaction mass, which is supersaturated with soda, and, after the solution has been neutralized, the new acid is precipitated with common salt and filtered off. The product thus obtained dissolves easily in warm water and rather difficultly in cold water. The acidic sodium salt is separated from the aqueous solutions of the neutral sodium salt by means of acids. Valuable dyes are obtained by coupling with diazo compounds.

The process proceeds in an analogous manner when using other i-8-aminonaphthol sulfonic acids respectively from other amines or substituted amines.

As the following example shows, the reaction can also be carried out in the presence of salts of amines or of condensing agents.

'Example 2.

239 parts of 1x8-aminonaphthol-4-sulfonic acid are mixed with 200 parts of p-toluidine, 150 parts

hydrochloric acid p-toluidine and 100 parts of water heated ^{to 120 0 for 48 hours under pressure.} The excess p-toluidine is then removed from the alkalized reaction mass by distillation with steam and, after the solution has been neutralized, the new product is precipitated with the aid of common salt, filtered off and, if necessary, purified by dissolving.

The arylaminonaphthol sulfonic acids thus obtained differ from the respective ones unsubstituted aminonaphthol sulfonic acids themselves by a considerably greater solubility their acidic alkali salts and the free morphosulfonic acids as well as their poorer solubility the neutral alkali salts. The arylated products are easily soluble Nitroso compounds, which do not turn violet with alkali.

Claims (1)

Patent-An saying: Process for the preparation of i-arylamino - 8 - naphthol sulfonic acids, consisting in that 1 · 8 - aminonaphthol sulfonic acids or their salts with aromatic amines, their substitution products or salts in the presence of Water heated. Neutral
Crystal shape and
colour Na-SaIz
solubility Sour iVa.-salt
(or free acid) easily soluble too
in cold water;
poorly soluble
in alcohol Shade α
fabric <
at the K
with diaz
p-nitra-
nilin it color
jr hold
[uppeln
listed
ct-naph-
tylamine Nitrosoverbin
characteristic manure
Nuance of
Dye
received at
Domes with
diaz. p-nitra-
nilin ι -phenylamino-
8-naphtol-
3 x 6-disulfonic acid white, too spherical
ligen aggregates
united needles easily soluble in
hot water,
heavier in cold;
easy to salt out;
poorly soluble
in alcohol white matted
Needles easily soluble
in water black blue
black brown-red crystal
powder; in water
very light with yellow
soluble in red color yellow Red ι -p-tolylamino-
8-naphtol-
3 x 6-disulfonic acid white needles a little harder
soluble like that
Phenyl acid white matted
Needles easily soluble black blue
black red crystal powder;
very easily soluble
with yellow color yellow Red ι -p-anisylamino-
8-naphtol-
3 x 6-disulfonic acid white, to balls
united needles easily soluble, yes
easy to salt out white needles in
Rosettes united easily soluble in
hot, heavy in
cold water black black
blue very easy in water
with yellow color
soluble dirty
brown purple ι -p-chlorophenyl-
amino-8-naphtol-
3 x 6-disulfonic acid white needles in cold water
pretty hard
soluble indistinct
Needles very difficult to dissolve
in cold water violet
black blue-
black yellow, in cold water
pretty hard
soluble crystals Red i-ß-naphthylamino-
8-naphtol-
3 x 6-disulfonic acid white needles in cold water
poorly soluble fine white needles easily soluble blue
black blue red heavy
Crystal powder;
easily soluble Red i-phenylamino
8-naphtol-
4 x 6-disulfonic acid white needles easily soluble Needles easily soluble violet
black dark
violet very light with yellow
soluble in red color yellow Red ip-tolylamino-
8-naphtol-
4 x 6-disulfonic acid white, conc
trisch grouped
Needles easily soluble Needles even in cold
Water pretty
soluble violet
black violet
blue light brown crystal
porridge; poorly soluble
in cold water Red ι -phenylamino-
8-naphtol-
4-sulfonic acid to leaflets
united needles in cold water
pretty hard
soluble white matted
Needles like phenyl
link Brown
black blue
black very easy in water,
almost colorlessly soluble hardly engages. ι -p -Tolylamino-
8-naphtol-
4-sulfonic acid Needles in cold water
poorly soluble white matted
Needles pretty easy
soluble in cold
water black blue ip-tolylamino-
8-naphtol-
3 x 5-disulfonic acid white needles pretty easy
soluble white needles blue-
black blue