DE1248191B - Process for the preparation of water-soluble trihalopyrimidyl dyes - Google Patents

Description

Process for the preparation of water-soluble trihalopyrimidyl dyes The invention relates to a process for the preparation of water-soluble trihalopyrimidyl dyes according to Patent 1228 013, in which organic dyes which have at least one exchangeable hydrogen atom are reacted with 2,4,5,6-tetrahalopyrimidine, the production is excluded from reactive azo dyes according to patent 1 109 807, and is characterized in that the organic dye is at most 1 mol of an anthraquinone dye of the formula is used per mole of tetrahalopyrimidine.

As 2,4,5,6-tetrahalopyrimidine, for. B. 2,4,5,6-tetrabromopyrimidine, 5-bromo-2,4,6-trichloropyrimidine and preferably the 2,4,5,6-tetrachloropyrimidine into consideration.

The reaction is carried out in an aqueous or aqueous organic medium. The tetrahalopyrimidine can be used as such in concentrated form or else be brought to use dissolved in an organic solvent. As a solvent acetone, dioxane, benzene, toluene and chlorobenzene are suitable.

The reaction temperature is the implementation ability of the individual 2,4,5,6-tetrahalopyrimidines adjust and varies between 40 and 100 - C, preferably between 80 and 95 - C. With regard to steam volatility of the halopyrimidines it is indicated in equipped with a reflux condenser to work in closed vessels.

The reaction is advantageous in weakly acidic, neutral or weakly alkaline agent, e.g. B. within the pH range of 3 to 9, preferably between 4 and 7. To neutralize the resulting hydrogen halide either initially acid-binding agents, such as sodium acetate, in the reaction solution or ammonium acetate, is added, or small portions are added during the reaction Sodium or potassium carbonate or bicarbonate in solid, powdered form or as concentrated aqueous solutions. Suitable neutralizing agents are but also aqueous solutions of sodium or potassium hydroxide. The addition of minor Amounts of a nonionic or anionic wetting or emulsifying agent for the reaction mixture can accelerate implementation.

When reacting the 2,4,5,6-tetrahalopyrimidines with the - NH2 group only one halogen atom reacts with an exchangeable hydrogen atom.

After the end of the condensation, the finished dye is made from his optionally previously neutralized solution or suspension with sodium or potassium chloride salted out, then suctioned off, washed with a sodium or potassium chloride solution and dried.

The pyrimidine dyes which can be prepared according to the invention are used for dyeing of leather, for dyeing, padding and printing on fibers of vegetable and animal origin Origin, of regenerated cellulose fibers, of casein fibers, of animalized ones Cellulose fibers, synthetic polyamide fibers and mixtures of these fibers with simultaneous or subsequent treatment of the colored material with alkaline reacting agents in the heat to the dye on the fiber fix. In particular, they are suitable because of their noun property, which by The addition of salt is reinforced for the dyeing of cellulose fibers using the exhaust process.

Since the new dyes are readily soluble in water, he cannot Any fixed part can easily be removed from the fiber by rinsing and / or soaping. The dyeings on cellulose fibers have very good light, water, sea water, Wash (also in multiple boil wash), sweat, soda boil, peroxide wash, chlorine wash, Rubbing and dry cleaning fastnesses. They are also well suited for the crease-proof finish.

Another important area of application for the new dyes is the dyeing of natural and synthetic polyamide fibers, especially level dyeing of synthetic polyamide fibers with different dye affinity (so-called streaky colored polyamide fibers). The colorations on natural and synthetic Polyamide fibers are very good light, water, wash, sweat, knuckle, rub and dry cleaning fast.

Compared to the reactive dyes known from US Pat. No. 2,773,871 the reactive dyes of the anthraquinone series which can be prepared according to the invention are distinguished by the much better acid vapor fastness of their dyeings on cotton.

In the following example, parts mean parts by weight and percentages Percentages by weight and temperatures are given in degrees Celsius.

EXAMPLE 107 parts of 1-amino-4- (4'-amino) -phenylaminoanthraquinone-2,3'-disulfonic acid are dissolved in 1000 parts of water at 85 ° to 90 ° Sodium and add 45 parts of 2,4,5,6-tetrachloropyrimidine. Stir at the indicated Temperature and maintains the pH of the mixture by adding dropwise dilute sodium hydroxide solution to around 5. When the condensation has ended - which is determined by chromatography can be - the reaction mixture is made with a little sodium hydroxide solution to pH 7 and enters 60 parts of sodium chloride. The failed dye is filtered hot. The filter material is washed with 500 parts of 10% sodium chloride solution, squeeze it well and dry it. A dark blue powder is obtained, which is in Water with a blue color dissolves.

If the 45 parts of 2,4,5,6-tetrachloropyrimidine are replaced in the above example by 55 parts of 5-bromo-2,4,6-trichloropyrimidine or by 82 parts of 2,4,5,6-tetrabromopyrimidine, this gives dyes with similar properties.

One can proceed as follows when dyeing: One prepares oneself Dyebath from 4 parts of the dye prepared according to paragraph 1 of this example in 2000 parts of water at 40 ° and 40 parts of calcined sodium sulfate. One goes now with 100 parts of cotton sateen, there are 20 parts of calcined sodium carbonate and heated to 90 ° in the course of 20 minutes. When the temperature is 65 and 90 ° has reached 40 parts of calcined sodium sulfate are added. The substantive Dye is now drawn onto the fiber, where it can be treated for 1 hour is fixed at 90 °. After the usual rinsing, the fabric is dried. You get a beautiful blue dye that is fast to soda and very lightfast.

100 parts of a striped fabric made from a mixed polycondensation product from hexamethylenediamine, adipic acid and w - aminocaproic acid are in 4000 parts colored a dye liquor containing the following additives: 0.2 parts of the according to paragraph 1 of this example prepared dye, 2 parts of acetic acid (80%), 0.5 Parts of sodium dinaphthylmethanedisulphonic acid.

The dyed material is introduced into the liquor and heated within from 30 minutes to 98 ° and stains for one hour at this temperature. Man gets a real blue coloration, which is not streaked.

Claims (3)

Claims: 1. Process for the preparation of water-soluble trihalopyrimidyl dyes according to patent 1228 013, in which organic dyes which have at least one exchangeable hydrogen atom are reacted with 2,4,5,6-tetrahalopyrimidine, the preparation of reactive azo dyes according to patent 1 109 807 is excluded, characterized in that the organic dye is at most 1 mol of an anthraquinone dye of the formula is used per mole of tetrahalopyrimidine. 2. The method according to claim 1, characterized characterized in that the reaction is carried out at temperatures of 40 to 100 °. 3. The method according to claim 1, characterized in that the reaction is carried out in weakly acidic, neutral or weakly alkaline medium. Into consideration pulled documents Austrian patent specifications 214545, 214 546; U.S. Patent No. 2,773,871; Angewandte Chemie, Vol. 73, 1961, pp. 128/129. At the notice A coloring table provided with explanations has been laid out in the application.