DE579325C - Process for the preparation of acylamino compounds from polynuclear compounds capable of forming cuepen - Google Patents

Description

Process for the production of acylamino compounds from polynuclear, compounds capable of vat formation It has been found that new, very valuable Acylamino compounds obtained when one amino compounds of anthraquinones or other polynuclear compounds capable of forming a vat with such polynuclear compounds Carboxylic acids condensed, which are also substituted by the carboxyl group isocyclic ring and at least one further, nitrogen-containing six-membered ring .contained, or by using halogen derivatives of anthraquinones or other polynuclear, compounds capable of vat formation with the amides of the above. marked Reacts carboxylic acids. The following may be mentioned as carboxylic acids of the type indicated: quinoline carboxylic acids with the carboxyl group in the 5-, 6-, 7- or 8-position and their substitution products, z. B. their halogen, alkyl, aryl derivatives, such as. Quinaldincarboxylic acids, chloroquinolinecarboxylic acids, also pyridinonaphthoic acids, pyridinoanthraquinone carboxylic acids, pyridinodiphenyl carboxylic acids, Coeramidon.incarbonsäuren or through carboxyl groups in the isocyclic ring substituted quinoxalines. Polynuclear ones suitable for the reaction, for vat formation Capable amino or halogen compounds are z. B. amino or halogen derivatives of benzanthraquinones, anthraquinone acridones, pyranthrones, anthanthrones, dibenzpyrenquinones, Dibenzanthrons, etc.

In the implementation of the aminoanthraquinones or the amino compounds one can also use polynuclear compounds capable of forming vats Derivatives of the carboxylic acids mentioned that change in the carboxyl group are e.g. B. acid halides, anhydrides, esters.

The reaction is expedient in the presence of diluents, z. B. nitrobenzene, dichlorobenzene, trichlorobenzene or naphthalene executed. as well acid-binding agents can be added; in the implementation of the halogen compounds mentioned with the above-mentioned acid amides, copper or its compounds are often added advantageous.

The reaction products are mostly in approximately theoretical yield and obtained in crystalline form. If necessary, you can use the usual methods, z. B. by crystallization or by treatment with hypochlorite solution, purified will. They color the vegetable fiber in a wide variety of shades. `oh the customary methods are used to obtain their leuco derivatives, e.g. B. the leucoesters. example 9 parts of quinoline-6-carboxylic acid are obtained by heating with excess thionyl chloride converted into the quinoline-6-carboxylic acid chloride. After the excess thionyl chloride Has been removed in vacuo, suspended, the acid chloride in 25o to 3oo Parts of nitrobenzene and 16 parts of i-amino-5-benzoylaminoanthraquinone are added. The mixture is heated to the boil for some time while stirring. As soon as the hydrogen chloride evolution has stopped, it is filtered hot. After cooling down, you can suck it up in an excellent way Yield crystallized reaction product and washes it with alcohol. It puts represents an orange-yellow crystal powder that turns yellow-red in color in sulfuric acid dissolves and from purple vat cotton in very strong, clear reddish yellow Dyes shades of very good fastness. 'The reaction product obtainable in an analogous manner from i-aminoanthraquinone turns green-yellow, that from i-amino-4.-benzoylaminoanthraquinone scarlet red, that of q.-aminoanthraquinone-2, i-benzacridone violet, that of diaminoanthanthrone, which one made of anthanthrone by nitrating with nitric acid in an organic agent and reduce can produce red.

Instead of quinoline-6-carboxylic acid, you can use other quinoline-Bz-carboxylic acids, z. B. quinoline-5- or -7-carboxylic acid, condense with viable amino compounds and then receives reaction products of similar properties.

If i-chloro-5-benzoylaminoanthraquinone is condensed with quinoline-6-carboxamide, in this way a reaction product is obtained whose properties are similar to those of the first above The product described above.

EXAMPLES The finely powdered quinoline-6-carboxylic acid chloride obtained from 18 parts of quinoline-6-carboxylic acid according to Example i is suspended in 250 to 300 parts of nitrobenzene. -2 parts of 1,5-diaminoanthraquinone are added and the mixture is heated to boiling, with stirring and under reflux, until the evolution of hydrogen chloride has ceased. The "still hot" reaction product is filtered off with suction and the remaining yellow reaction product is washed thoroughly with hot nitrobenzene and then with alcohol. It dissolves in orange in sulfuric acid and dyes cotton in very strong, reddish-yellow shades with very good fastness properties from a violet vat If necessary, clean yourself by crystallizing from quinoline or similar high-boiling solvents or by treating with sodium hypochlorite solution.

Example 3 65 parts of quinoline-5, 8-dicarboxylic acid chloride by treating the quinoline-5, 8-dicarboxylic acid with thionyl chloride "are with Zoo share i-Amino-5-benzoylaminoanthraquinone in 5000 parts dichlorobenzene for as long heated to boiling until no more unchanged starting material can be detected. The still hot reaction mixture is then filtered off. Separates from the filtrate the resulting dye is removed in the form of yellow needles that form a wine-red vat deliver, from which the vegetable fiber in strong, very clear yellow tones is dyed with good fastness properties. Example q.

10 parts of i-amino-5-methoxyanthraquinone, 10 parts of quinoline-6-carboxylic acid chloride and 25o parts of dichlorobenzene are heated to boiling under reflux cooling for so long until no more unchanged starting material can be detected. Then it is filtered the reaction mixture in the heat, the resulting dye from the The filtrate is deposited in the form of yellow crystals. The reaction product dissolves in concentrated Sulfuric acid with a yellow-brown color, provides an orange-red vat from which the vegetable Fiber is dyed in greenish yellow tones of good fastness.

The table below describes some other dyes obtainable by the present process. Acquisition of Amino compound carboxylic acid reaction product on cotton 1 # 5 diamino anthraquinone. . . . . . . . . . . . . Bromquinoline-6-carboxylic acid reddish yellow 1-Amino-5-benzoylaminoanthraquinone ... bromoquinoline-6-carboxylic acid golden yellow 1-Amino-5-benzoylaminoanthraquinone ... quinoline-5-carboxylic acid greenish yellow 1-Amino-5-benzoylaminoanthraquinone ... quinoline-8-carboxylic acid greenish yellow 1 aminoanthraquinone. . . . . . . . . . . . . . . . . Quinoline-5 # 8-dicarboxylic acid greenish yellow Coloring of the Amino compound carboxylic acid reaction product on cotton i-aminoanthraquinone. . . . . . . . . . . . . . . . . Quinoline-5 # 7-dicarboxylic acid I greenish yellow 2-Aminoanthraquinone .............: ... quinoline-6-carboxylic acid greenish yellow i-Amino-5-p-chlorobenzoylaminoanthra-quinoline-6-carboxylic acid yellow chinone i-Amino-5-dichlorobenzoylaminoanthra-quinoline-6-carboxylic acid yellow chinone 2-amino-3-cyananthraquinone. . . . . . . . . . . Quinoline-6-carboxylic acid greenish yellow i # 4-Di (m-methoxybenzoyl) amino-quinoline-6-carboxylic acid bluish-tinted red 5-amino-5-aminoanthraquinone 5-amino-5'-benzoylamino-i. i'-anthrimide-quinoline-6-carboxylic acid golden orange carbazole 4-Amino-5-benzoylamino-8-methoxy-quinoline-6-carboxylic acid red-brown anthrimide carbazole 5-5'-diamino-i. i'-oxamidoanthraquinone quinoline-6-carboxylic acid golden orange Monoaminoanthanthrone. . . . . . . . . . . . . . . Quinoline-6-carboxylic acid bluish-tinted red Monoamino-allo-ms-naphthodianthron. . . Quinoline-6-cai-bonic acid red 4-Amino-i # 2-o-chlorophenylanthraquinone-quinoline-6-carboxylic acid orange imidazole 5-aminoanthrasulfone ................. quinoline-6-carboxylic acid yellow i # 5-Diamino-4 # 8-dioxyanthraquinone ... quinoline-6-carboxylic acid violet

Claims (1)

PATFNTANSPRIJCFI. ' Process for the preparation of acylamino compounds made of multi-core compounds capable of forming vats, characterized in that that one amino compounds of anthraquinones or other polynuclear, for vat formation capable compounds with such polynuclear carboxylic acids or reactive Carboxyl derivatives condensed which, in addition to that substituted by the carboxyl group isocyclic ring and at least one further, nitrogen-containing six-membered ring contain, or that halogen derivatives of anthraquinones or other polynuclear, compounds capable of forming vats with the amides of those identified above Reacts carboxylic acids.