DE706106C - Process for the preparation of o-oxyazo dyes - Google Patents

Description

Process for the preparation of o-oxyazo dyes It has been found that valuable azo "dyes are obtained; if added o-aminophenols, `which contain a nitro group in the nucleus, with a-acylamino-I-oxy-q.-alkylbenzenes clutch.

The coupling is carried out in the presence of the usual acid-binding agents, such as sodium bicarbonate, sodium carbonate, sodium hydroxide, ammonia, milk of lime, magnesium carbonate or pyridine. Optionally, can. also two or more of the mentioned Additives are used together.

The so available. Dyes give full color after chrome-plated wool brown shades with very good fastness properties. Some of the dyes are suitable also for dyeing wool after the incorporation: adchrome process.

- The from - the German patent 351001 known, by domes of diazotized q., 6-dinitro-2-amino-I-oxybenzene with α-acetylamino-I-oxy-q.-methylbenzene The o-oxyazo dye available is superior to the new dyes in terms of lightfastness.

Example I 23.4 parts of 2-amino-I-oxy-4-nitrobenzene-6-sulfonic acid are diazotized with 6.9 parts of sodium nitrite and 22 parts of hydrochloric acid. The diazo compound is treated with 16.5 parts of 2-acetylamino-z-oxy- [methylbenzene] in the presence. an acid binding agent coupled. The separated and dried dye is a dark powder, which dyes wool from an acid bath in yellow-brown tones, which turn into a full brown when chromium-plating.

If one uses instead of the i OXy @; , 2-acetylamino-4-met @ hylbenzols 2-Benza amino-i-oxy-4-methylbenzene as the azo component, this gives a dye which, after chrome-plated on wool, provides a more yellowish, brown coloration.

As azo components, 2-oxalylamino-i-oxy-4-methylbenzene and the phthalamic acid obtainable from 2-amino-i-oxy-4-methylbenzene and phthalic anhydride of the formula - use, similar dyes being obtained.

Example 2 15.4 parts of 2-amino-i-oxy-4-nitrobenzene are mixed with 6.9 parts Sodium nitrite and 25 parts of hydrochloric acid are diazotized. The diazo compound is in the presence of pyridine with 6.5 parts of 2-acetylamino-i-oxy-q.-methyl lbiemzolg! pkupp @ elx. The separated and dried dye is a dark powder, which Wool from an acid bath dyes in brownish tones that are converted into a go full brown. The dye is ideal for dyeing wool according to the single bath chrome process.

If 2-amino-i-oxy-4-nitro-6-chlorobenzene or 2-amino-i-oxy-4-nitro-6-methylbenzene is used as the diazo component, then If you keep dyes with similar properties societies. Dyes with similar properties rden are also obtained if one end-mentioned diazo components with ormylarnino-i-oxy-4-methylbenzene, 2-Ox- , # lamino-i-oxy-4-methylbenzene or with the from 2 .4mino-i-oxy-4-methylbenzene and Phthalic anhydride available phthalic amic acid couples. Example 3 23.4 parts of 2-amino-i-oxy-fi-nitrobenzene-4-sulfonic acid are diazotized with 6.9 parts of sodium nitrite and 22 parts of hydrochloric acid. The Diazov compound is coupled with 22.7 parts of 2-benzoylamino-i-oxy-4-methylbenzene in the presence of an acid-binding agent. The separated and dried dye is a dark powder, which dyes wool from an acid bath in brown-violet tones, which turn into a dark brown when chromium-plating.

Example 4 23.4 parts of 2-amino-i-oxy-4-nitrobenzene-6-sulfonic acid are diazotized with 6; 9 parts of sodium nitrite and 22 parts of hydrochloric acid. The diazo compound is with 28.3 parts of 2-benzoylamino-i-öxy-4-tertiary amylbenzene in the presence of a acid-binding agent coupled. The deposited and dried dye provides a dark powder made of wool. with acid bath in shades of brown, which turn into a yellowish dark brown when chromium plating. The dye is also ideal for dyeing wool using the single-bath chrome process.

The following list shows further dyes obtainable by the present process and the hues of the dyeings obtainable with them. '' Shade of the Diazo component Azo component chromed coloring on wool i. 2-amino-i-oxy-4-nitrobenzene 2-acetylamino-i-oxy-4-tert. amyl-reddish brown benzene 2. 2-Amino-i-oxy-4-nitrobenzene like brown 6-sulfonic acid 3. Likewise 2- (4'-methylphenoxy) acetylarnino- yellowish dark- - i-oxy-4-methylbenzene brown 4. 2-Amino-z-oxy-6-nitrobenzene-like, violet-tinged 4-sulfonic acid dark brown 5. 2-Amino-z-oxy-4-nitrobenzene 2-chloroacetylamino-i-oxy-4-methyl- reddish dark benzene brown . Shade of the . Diazo component Azo component chromed coloring on wool 6. 2 Amino-i-oxy-4-nitro-6-me- 2-chloroacety -z-öxy- ¢ -methyl- reddish dark- thylbenZene benzo1; _ .# Brown 7. 2-Amino-i-oxy-4-nitrobenzene- 2- (2'-chlorobenzoyl) -amino-z-oxy- yellowish dark- 6-sulfonic acid 4 methylbenzöl - brown 8 .. 2-Amino-i-oxy> 6-nitrobenzene-like. _. dark brown 4-sulfonic acid G. 2-Amino-i-oxy-4-nitrobenzene-2-benzoylamino-i-oxy 4-tert. butyl yellowish dark, 6-sulfonic acid benzene brown io: the same. I 2-benzoylamino-i-oxy-4-cyclohexyl-dark brown Benzenes -

Claims (1)

PATENTÄIV.SI'RUCII Process for the production of o-oxy- azo dyes, denoted by. that one dianotated o-aminophenols, which contain a nitro group in the core ° th, with 2-acylamino @ -z-oxy-4-alkylben- zolen couples. .