DE743674C - Process for the production of Kuepen dyes - Google Patents

Description

Process for the preparation of vat dyes It is known that by treating (i'-anthraquinonyl) -amino-Bz i-benzanthronyl-Py i -pyrazole anthrones, those by amino groups or substituted amino groups or in the 2-position des Anthraquinonyl radicals can be substituted by an aldehyde group, with alkaline ones Contains condensation agents light- and weather-fast vat dyes. These well-known However, dyestuffs have disadvantages, such as unsatisfactory leveling capacity or through-coloring capacity, Soda boiling or ironing fastness sometimes not satisfying all requirements, so that they can be used for some purposes, for example for dyeing reprecipitated cellulose or mixed fabrics or mixed webs made of reprecipitated cellulose and cotton, are not very suitable. It has now been found that dyes of the benzanthrone series can be used receives, which with very good light and weather fastness to the well-known similar dyes superior in the above properties or at least in one of them are, if one 6- (i'-anthraquinonyl) -amino-Bz i-benzanthronyl-Py i-pyrazolanthrone, in which the hydrogen atom of the imino group is in the 6-position of the benzanthrone is replaced by a low molecular weight alkyl radical or or and in which the Anthraquinori or pyrazolanthrone radical or both at least one low molecular weight Alkyl group, oxy, methoxy, ethoxy, mercapto, methyl mercapto, ethyl mercapto, Wear cyano or carboxamide groups and those in the 2-position of the pyrazolanthrone radical none contain substituents which prevent ring closure, with alkaline Treated condensing agents.

The starting materials required for the process are prepared in a known manner, for example by reacting 6-Bz i-dibromobenzanthrone first with 1 mole of a pyrazole anthrone and then, advantageously without separating off the 6-bromobenzanthronyl-Py i -pyrazole anthrone initially formed, with 1 mole of an i-aminoanthraquinone (cf. patents 468 896 and 52 0 395) The parts mentioned in the examples below are parts by weight. EXAMPLE i 100 parts 6- (2'-methyl-i'-anthraquinonyl) -amino-Bzibenzanthronyl-Py i are carried into a melt of about 95 to 97.degree -pyrazolanthrone (obtainable by reacting 6-Bz i-dibromobenzanthrone first with 1 mole of pyrazolanthrone and then with 1 mole of i-amino-2-methylantlirachinone) and stirred for about 5 hours at this temperature. The melt is then poured into water, boiled with the introduction of air until the dye has separated out, filtered off with suction, washed out with water and dried. This gives a dye which dyes cotton from the vat in blue-tinged gray tones. The leveling power, the soda boiling fastness and the ironing fastness of the new dye is better than that of the corresponding known dye made from 6- (i'-anthraquinonyl) -amino-Bz ibenzanthronyl-Py i-pyrazolanthron.

In the same way, 6- (2'Äthyli'-arthraquinonyl) -amino-Bz i-benzanthronyl-Py i-pyrazolanthron a dye of similar properties.

From 6- (8'-cyano-i'-anthraquinonyl) -amino-Bz i-benzanthronyl-Py i-pyrazolanthrone a purple-tinged gray dye of good leveling power is obtained and very good tone stability in the soda cooking test; also from 6- (2'-cyano-i'-anthraquinonyl) -amino-Bz i -benzanthronyl-Py ipyrazolanthron or 6- (2'-methoxy-i'-anthraquinonyl) -amino-Bz i-benzanthronyl-Py ipyrazolanthron or from 6- (i'-anthraquinonyl) -amino-Bz i-benzanthronyl-Py i-pyrazole anthrones, which contain carboxamide groups in the anthraquinonyl radical gray dyes with very good leveling power.

EXAMPLE e 125 parts of a melt obtained by reacting 6-Bz i-dibromohenzanthrone with first 1 mole of pyrazolanthrone and then 1 mole of i-amino-2-oxyanthraquinone are carried with stirring into a hot melt of about 95 to 970 parts of potassium hydroxide and 500 parts of ethanol Compound and the mixture is stirred for about 6 hours at this temperature. After the work-up described in Example i, a dye is obtained which dyes cotton from a dark greenish blue vat in real gray, excellently leveling shades.

If i-amino, 2-oxyanthraquinone is used instead of i-amino-2-mercaptoanthraquinone, a gray vat dye with good fastness properties is also obtained in this way and excellent leveling ability.

Example 3 100 parts of a 6-Bz i-dibromobenzanthrone by reaction with first 1 mole of pyrazolanthrone and then 1 mole of i-methylamino-2-ethoxyanthraquinone (obtainable by reacting i-chloro-2-oxyanthraquinone with methylamine and treating of the i-methylamino-2-oxyanthraquinone obtained with diethyl sulphate) are in a 95 to 97 ° hot melt of q.oo parts of potassium hydroxide and q.oo Stir parts of ethanol. The mixture is then kept at the same for a few hours Temperature held. After the usual work-up, a dye is obtained which Cotton from dark blue vat in real, weak. bluish gray, excellent equalizing tones.

Example q.

Treated by reacting i mole of 6-Bz i-dibromobenzanthrone initially with 1 mole of 4-ethyl mercaptopyrazolanthrone (obtainable from q. - Ch lorpyrazolanthron and ethyl mercaptan) and then one mole of i-methylaminoanthraquinone compound with potassium hydroxide in the manner described in Example e, one obtains a graying vat dye of good fastness properties and excellent Equalizing ability.

A dye with similar properties is obtained by using the with 4.-Methylmercaptopyrazolanthron available compound used.

Claims (1)

PATENT CLAIM: Process for the preparation of vat dyes of the benzanthrone series, characterized in that 6- (i'Anthraquinonyl) -amino-Bz i-benzanthronyl-Py ipyrazolanthrones, in which the hydrogen atom of the imino group is in the 6-position of the benzanthrone by a low molecular weight alkyl radical is replaced or or and in which the anthraquinone or pyrazole anthrone radical or both carry at least one low molecular weight alkyl group, oxy, methoxy, ethoxy, mercapto, methyl mercapto, ethyl mercapto, cyano or carboxamide group and which are in the 2-position of the Pyrazolanthronrestes do not contain the ring closure hindering substituents, treated with alkaline condensation agents. To distinguish the subject of the application from the state of the art, the following publication was considered in the granting procedure: German patent specification ...... No. 52o 395.