DE261047C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

- M 261047 CLASS 22 a. GROUP

in Basel

Process for the preparation of azo dyes. Patented in the German Empire on February 2, 1912.

Many azo dyes, which contain phenol as a component, are so sensitive to alkali, that their usefulness in dyeing is impossible. To remedy this evil, one has previously alkylated such dyes.

It has now been found that the alkali sensitivity of such dyes can also be eliminated can if you put the hydrogen in

ίο the phenolic hydroxyl groups of the same replaced an aryl sulfo moiety. Assuming this is based on products that have the character have acidic wool dyes, the entry of the aryl sulfo group gives rise to this character not changed and only with a corresponding shift in the original nuance perfect alkali fastness achieved. On the other hand, if the starting materials are direct Cotton dyes, as opposed to alkylation, are used in most cases the entry of the aryl sulfo groups greatly weakened the affinity of the new dyes for cotton. On the other hand, they are ideally suited for dyeing wool and silk and show up against the corresponding alkylated ones Products have increased flexing and water fastness. In some cases, for example when introducing an aryl sulfo group into the nitrosostilbene disulfonic acid azophenol (arnica yellow, see Schultz, Julius, Farbstofftabellen, 4th ed., p. 52, no. 144) you get one Dye which has no decrease in affinity for the alkylated Cotton shows.

The introduction of the arylsulfo group is best done in the W ^T else that one gradually Arylsulfochlorid enters into the soda or weakly natronalkalische solution or suspension of the starting dyes with good stirring until a sample no longer exhibits alkali sensitivity. The dyes to be treated can also be reacted with the aryl sulfochloride immediately after their preparation, without being isolated beforehand.

Examples:

1. The azo dye prepared from 18.4 kg of benzidine by coupling with 30.3 kg of 2-naphthylamine-3 · 6-disulfonic acid and 9.4 kg of phenol is mixed in water with 30 kg of soda and then at 30 to 35 ° C. 24 kg of benzenesulphonyl chloride gradually added with thorough stirring. The dye, which is partly in solution, takes on a more yellow color and finally separates out as a shiny red-orange colored precipitate, which is filtered, pressed and dried. The new dyestuff dyes WOI ¹ e and silk in the acid bath alkali-orange, and the dyeings are fulling and water-fast.

2. The azo dye (arnica yellow), which occurs during the condensation of p-nitrotoluenesulfonic acid, is dissolved is obtained with p-aminophenol and sodium hydroxide solution, in hot water, makes, weakly alkaline soda and sets now with thorough stirring at 70 to 75 ° C. gradually p-Toluolsulfochlo rid to, whereby one Care is taken to ensure that the alkaline reaction is always maintained. Shows a

Azo dyes
which as starting material
was used ■ Applied
Aryl sulfochloride Shade on wool
and silk p-aminodiphenylamine sulfonic acid azophenol p-toluenesulfo-
chloride greenish yellow / Amino-R acid
Benzidine <,
^ Phenol Chlorobenzenesulfo-
chloride orange / Sulfophenylmethylpyrazolone
Benzidine monosulfonic acid <;
^x phenol p-toluenesulfo-
chloride reddish yellow . . / Sulfophenylmethylpyrazolone
m-Tohdin <
NPhenol p-toluenesulfo-
chloride greenish yellow / Naphthol disulfonic acid G
Benzidine <
NPhenol Naphthalene-ß-sulfo-
chloride yellow Red / Naphthol disulfonic acid G
'Benzidmi,
^ Phenol Nitrobenzenesulfo-
chloride yellow Red . / Naphthol disulphonic acid ι · 3 · 6
Benzidine <,,
^ Phenol p-toluenesulfo-
chloride bluish red . . , Naphthol disulfonic acid 1 x 3 x 6
m-tolidine / ^FJ -
^ Phenol p-toluenesulfo-
chloride yellowish red /Phenol
Diamidostilbene disulfonic acid i
^ Phenol p-toluenesulfo-
chloride yellow / Amino-R acid
Benzidini
^X o-cresol p-toluenesulfo-
chloride orange / Naphthol disulfonic acid G
Benzidm <
^X m-cresol p-toluenesulfo-
chloride yellowish red / Amino-R- acid
Benzidine <
^X p-cresol p-toluenesulfo-
chloride orange Sulphanilic acid azo-m-oxydiphenylamine p-toluenesulfo-
chloride yellow-brown . . /Phenol
p-phenylenediamine ^. . ,,.
\ Amidonaphthol disulfonic acid H p-toluenesulfo-
chloride blue-violet p-phenylenediamine-phenol, acid-coupled with amido-
naphthol disulfonic acid H, and further combined alkaline
with diazobenzene chloride p-toluenesulfo-
chloride blue black

Claims (1)

If the sample taken out is no longer sensitive to alkali, it is allowed to cool down a little and filtered the separated out as a yellow precipitate Dye off. It dyes cotton yellow directly, alkali-proof and acid-proof. Another number of the azo dyes obtained by the present process are in compiled in the adjacent table. Pa τ ε ν τ - A ν s ρ r υ c ti:
A process for the preparation of azo dyes, which consists in introducing an aryl sulfo radical into each phenol hydroxyl group of azo dyes which have phenol or a substitution product thereof once or twice as a component.