DE1073131B - Process for the production of dyes - Google Patents

Description

Process for the preparation of dyes It has been found that valuable new blue dyes are obtained if further substitutions are made, if necessary 3-Imino-4,7-diamino-5,6-phthaloyl-isoindolenine, which are reactive in the 1-position Groups are substituted, reacted with aliphatic or cycloaliphatic amines.

Interchangeable groups that are in the 1-position of the isoindolenines, can e.g. B. be alkoxy or mercapto groups. Furthermore, these compounds still z. B. by halogen atoms, acylamino, hydroxy or other amino groups or further alkoxy groups may be substituted.

The preparation of the compounds used as starting material can be done using a wide variety of methods. Those substituted by alkoxy groups Connections can e.g. B. obtained in such a way that you 1,4-diamino-anthraquinone-2,3-dinitrile with an alkali alcoholate solution, e.g. B. a dissolution of sodium in methanol, Ethanol, propanol, butanol, amyl alcohol. The corresponding Merkapto connections z. B. from the 1,4-diamino-2,3-dicyano-anthraquinones in alcohol with anhydrous Obtained sodium sulfide. They can then be alkylated, or one sets in the implementation of the dicyan, instead of sodium sulfide, alkali cappans are used. The 1,3-diimino-4,7-diamino-5,6-phthaloyl-isoindolenine can e.g. B. from the 1-methoxy-3-imino compound can be obtained by reaction in methanol with ammonia.

Aliphatic or cycloaliphatic ones suitable for the process according to the invention Amines are e.g. B. ethanolamine, 1-amino-3-dimethylaminopropane, 1-amino-3-alkoxypropane, 1-amino-3-methylaminobutane, allylamine, 3-aminobutanol- (1), hexahydroaniline.

The reaction of the two reaction components is expediently carried out in an inert solvent, e.g. B. methanol or in excess amine, advantageously at a slightly elevated temperature.

The new dyes obtained according to the invention are particular for dyeing synthetic textiles such as those made of polyamide, polyester or Acrylonitrile fibers are suitable. The 3-imino-4,7-diamino-5,6-phthaloyl-isoindolenine used as starting material, which are substituted in the 1-position by reactive groups also pull on synthetic fibers.

Compared to US Patents 2,628,963 and 2,770,625 known dyes draw the dyes obtained according to the invention significantly better on the fiber materials to be dyed, such as polyester or polyamide fibers, on.

Example 1 3.2 parts of 1-methoxy-4,7-diamino-5,6-phthaloyl-isoindolenine are suspended in 35 parts of methanol. After adding 35 parts of ethanolamine the suspension is heated to boiling for several hours. One lets it cool down, sucks and the residue was washed with methanol until it was almost colorless. It will blue needles are obtained, which are in sulfuric acid with red, but in hydrochloric acid dissolve with purple paint. The vat is purple.

Analysis of the dye in one of its tautomeric forms by the formula Cis His 0s N5 Calculated ... C 61.9, H 4.3, O 13.8, N 20.00 / 0; found .... C 62.3, H 4.3, O 13.9, N 19.3 0/0.

The dye is applied in finely divided form to polyester and polyamide fibers in greenish blue, very real shades. The coloration can be known In a dye liquor containing 0.1 part of the dye, 400 parts are carried out as follows Contains water and 8 parts of benzoic acid at 25 to 30 ° C with 10 parts of polyester fiber entered and the temperature increased to 100 ° C within 20 minutes. These The temperature is kept for 1 hour, the fiber material is removed and treated afterwards rinsing for 20 minutes at 70 ° C with a mixture of 5 parts of sodium hydroxide solution (38 ° B6) in 1000 parts of water. After acidification it is rinsed again. the Production of 1-methoxy-4,7-diamino-5,6-phtha = loyl-isoindolenine can be carried out as follows This is done in the following manner: 2.8 parts of sodium are dissolved in 280 parts of methanol; then wears 28.8 parts of 1, -I-diamino-anthraquinone-2,3-dinitrur are introduced and the suspension is stirred several hours at 60 to 70 ° C. The cooled melt is suctioned off with methanol Washed and dried until colorless. The residue consists of dark blue Needles. The solution color in sulfuric acid is greenish blue, very quickly after turning brown, but red in hydrochloric acid. Vat: blue-violet.

The compound obtained pulls according to the dyeing process given above already on polyester fibers in a blue shade.

Example 2 3.2 parts of 1-methoxy-3 imino-4,7-diamino-5,6-phthaloylisoindolenine are in a mixture of 35 parts of methanol and 9 parts of 1-methoxy-3-aminopropane heated to the boil for several hours. The suspension is filtered off with suction while cold and with methanol washed until the drain is almost colorless. The compound crystallizes in bluish black Prisms with metallic luster. It dissolves violet in hydrochloric acid. The vat is blue-violet. Solution color in sulfuric acid: bluish red. Polyester fibers are made in very real stained blue tones.

Example 3 3.2 parts of 1-methoxy-4,7-diamino-5,6-phthaloyl-isoindolenine are in a mixture of 32 parts of methanol and 10 parts of 1-amino-3-dimethylaminopropane entered and heated to the boil for several hours. Let it cool down, wash with it Methanol until the drain is almost colorless, and gets the dye in blue Needles in almost quantitative yield. It dissolves in concentrated hydrochloric acid with purple color. The vat is purple. The dye dyes polyacrylonitrile fiber from acetic acid bath in very real blue tones.

Claims (1)

PATENT CLAIM: Process for the production of dyes, thereby characterized in that optionally further substituted 3-imino-4,7-diamino-5,6-phthaloyl isoindolenine, which is substituted in the 1-position by reactive groups are reacted with aliphatic or cycloaliphatic amines. Considered References: U.S. Patent Nos. 2,628,963, 2,770,625. At the notice 1 staining table with explanations has been laid out in the application.