SU428614A3 - METHOD OF OBTAINING WATER-SOLUBLE MONO-ROSE DYES - Google Patents

Description

This invention relates to a method for producing new water-insoluble monoazo dyes for dyeing various materials in V-N 7s-CH-C01CHN f YCO-CHi where Y is OCH3. However, the obtained dyes paint various materials in yellow colors with low color indexes. In order to improve color characteristics and broaden the range of color shades, they offer an approach to the preparation of water-insoluble monoazo dyes of the general formula (- N - SI - CO - CO - CH j where YOCN, -NHR, where: R is hydrogen or alkyl with 1-4 carbon atoms, X hydrogen, halogen, methyl, methoxy or ethoxy yellow with a wide range of hues. A method for preparing water-insoluble monoazo dyes of the general formula VcH, a group is known. The method consists in that the diazo-composition is a compound of the formula CO-Y. Where Y has the above value put on the op Tanya with the coupling component - 5-atsetoatsetilaminobenzimndazolonom general formula SNz- CO- CH2-CO-NH-k -SH wherein X is as defined above, followed by isolation of the desired product known npneMOiM.

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To obtain the diamides of 5-aminosophthalic 1 acid can, for example, as follows. 5-nitroisophthalic acid dichloride is reacted with ammonia or alkylamines with 1-4 carbon atoms, or the 5-nitroisophthalic acid esters are treated with the above compounds at elevated temperature. The 5-nitroisophthalic acid diamides obtained in this way can be catalytically reduced. lene in the bottom of the meads 5-aminonzophthalic acid. To obtain 5-amio-isophthalic acid dimethyl ester, 5-nitroisophthalic acid can be esterified with methanol, followed by reduction. The preparation of the constituents is best carried out by the exchange reaction of the corresponding aminobenzimidazolopes with diketene in water or in an organic solvent, for example, in glacial acetic acid.

The coupling reaction can be carried out in the usual way, preferably in an aqueous medium; It is advisable to carry out the reaction in a non-ionic, anionic or cationic dispersion medium.

In order to provide the most appropriate crystalline structure, it is recommended that the mixture for combination be heated for some time, for example by boiling or Heating above liOO ° C under pressure, eventually in the presence of organic solvents such as dichlorobenzene, dimethylformamide, or rosin soap. Especially clean and durable tones can be obtained with the use of kratels indicated in the application. The dyes (after combination) in the form of wet filter cakes or dried powders are subjected to further processing with organic solvents, for example, pyridine, dimethylformamide, alcohol, glycol, ethylene glycol monomethyl ether, glacial acetic acid, chlorobenzene, dichlorobenzene or nitrobenzene at reflux temperature with reflux resin, chlorobenzene, dichlorobenzene or nitrobenzene at reflux temperature. or at elevated temperature iodine pressure and incubated for some time. It is also possible to grind dyes in the presence of auxiliary substances for this treatment. It is possible to combine dyes in the presence of carriers suitable for the manufacture of farblak.

New pigment dyes are suitable for printing (printed) inks, farblakov, dispersive small paints for dyeing rubber, plastics and natural or synthetic resins. New dyes are also suitable for the pigment printing on substrates, especially on materials made from textile fibers or other nongosity formations, for example paper. Dyes can also be used for other purposes, for example, in finely divided form, they can be used to dye viscose silk, or ethers or esters

428614

cellulose, polyamides, polyurethanes, polyglycolterephthalates - or polyacrylonitrile in a spinning mass, or dl. coloring paper.

Dyes can be well processed in the above environments. Vykraski differ good light resistance, weather resistance, durability against migration. They are resistant to high temperatures and chemicals, especially dyes.

Example .1. 18 wt. including diamide 5-aminoisophthalic acid is stirred for 15 min with 50 vol. including glacial acetic acid. After that, the mixture is diazotized at 20 ° C with an equivalent amount of nitrosylsulfuric acid, stirred for another 30 minutes, poured into 400 vol. water is clarified with infusor earth and a possible excess of nitrous acid is decomposed with amidosulfonic acid. 24 wt. including benzimidazolone 5-amino-acetoacetic acid is dissolved at 20-25 ° C in a mixture of 200 vol. including water and 30 vol. including ten t-normal sodium alkali. The solution is clarified with active charcoal and in the filtrate the azo-component is precipitated by stirring in drops of 18 vol. including glacial acetic acid. Then add another 20 vol. including a 10% aqueous solution of the reaction product, approximately 20 mol of ethylene oxide and 1 mol of stearyl alcohol.

In this c), the azo component spent at a fixed pH value (at a level of about 5.5) is poured at approximately 20 ° C and the diazo solution is intensively moved. The combination ends right there. The mixture is boiled, sucked off hot, washed thoroughly with water and dried at 65 ° C. A half yellow pigment is crushed and heated with 600 vol. including glacial acetic acid for 1.5 hours to 90 ° C. Sucked off, washed with acetic acid with methanol and water and dried the dye. A yellow particulate pigment is obtained, characterized by a pure tone. In polyvinyl chloride, lacquer, printing ink or dispersive paint, it is possible to obtain from this dye yellow tones with high light resistance and very high durability when protected by external varnish, high resistance to migration in polychloride, with excellent heat resistance.

Pr and m er 2. 23.5 wt. including BIC-N, N-ethylene lamp of 5-aminoisophthalic acid is mixed with 60 vol. part of normal hydrochloric acid and 60 vol. hours of water for 1 hour. The mixture is then diluted with 150 vol. hours and diazotized at O-5 ° C, the action of 20 vol. including a tinormal solution of sodium nitrite. Clarified with infusor earth, and an eventual excess of nitrous acid is decomposed with amidosulfonic acid.

This diazo solution at 20 ° C and vigorous stirring is poured into the acetic acid suspension of the azo component, which is obtained as follows: 24 wt. including 5-acetoacetyl amiaobenzimidazolo:; and with it they mix 20–25 ° C with 200 vol. including ash, after which 30 vol. including ten tinormalyugo caustic soda solution. After clarification with active carbon for 30 minutes with good stirring, pour in a solution of 300 vol. including water, 41 vol. including glacial acetic acid and 40 vol. including ten tinormal solution of caustic soda, to which was added 20 vol. including 5% aqueous solution of the reaction product 30 mol of ethylene oxide and 1 mol of oleyl alcohol. The combination ends very quickly. The mixture is heated to boiling, filtered off with suction, washed with water and dried at 65 ° C. The resulting yellow pigment with a red tint gives color of the same high quality as the dye described in example 1. Example 3. The combination is carried out as described in example 2. The dry dye powder is heated with 300 vol. including glacial acetic acid for 75 minutes to 70 ° C. Suction is carried out, acetic acid is displaced by washing with methanol and water and dried. In this way, a pigment is obtained, which gives a yellow color with a green tint with the same strength indicators as indicated in Example 2. Example 4. 26.3 wt. Part 2 of bis-N, N-isopropylamide 5-aminoisophthalic acid was diazotized in Example 2, after which the azo-component was prepared and the combination was carried out as in Example 1. The dye powder was heated for 1.5 hours with 470 vol. including glacial acetic acid to 100 ° C. The mixture is filtered off with suction, washed with methanol and water until glacial acetic acid is displaced and dried. The resulting pigment gives yellow tones with

CONHR red otten.m. For its strength properties, this dye is similar to that obtained in Example 1. Example 5. The combination is carried out as in Example 4. A dry dye is heated for 2 hours to 110 ° C with 280 vol. including o-dichlorobenzene. The dichlorobenzene is sucked off and washed with methanol. At the end, they are washed again with water and dried. The resulting pigment gives a strong tone, with almost the same strength properties as that of the dye in example 4. However, in this case the green tint is much more intense. Example 6. 20.8 wt. Part of 5-aminoisophthalic acid bis-N, N-methylamide is diazotized according to Example 2. The azo-component suspension is obtained in the following way: 25 wt. including 7-methyl-5-acetoacetylaminobenznmidazolone dissolved in a mixture of 200 vol. including water and 60 vol. including ten tinormal solution of caustic soda at 20-25 ° C. After clarification with active carbon, the azo-component is precipitated in the filtrate at 10 ° C with stirring in the presence of 18 vol. including glacial acetic acid. The combination is carried out according to Example 1. A dry dye powder is then heated for 4 hours to 100-110 ° C in the presence of 360 vol. including glacial acetic acid. After suction, washing with methanol and water and drying, a yellow pigment is obtained with the same excellent strength properties inherent in the dye of Example 1. In the attached table there is an even greater number of dyes that can be obtained in a similar way. Also indicated are the shades of these dyes in the textile case. PRI iM e 7. 7. 20.9 weight. including dimethyl ester of 5-a. myioisophthalic acid is stirred with 80 vol. including a tinormal hydrochloric acid for about 1 hour and then diluted with 300 vol. h of water. Diazotize at 10 ° C using 20 vol. including a tinormal solution of sodium nitrite. After clarifying with infusor earth, a possible excess of nitrous acid is eliminated by adding a small amount of amidosulfonic acid. This diazo solution is poured under conditions of good mixing at a temperature of about 20 ° C to the acetic acid suspension of the azo compounds, which is obtained as follows: 24 wt. including 5-acetoacetylaminobenzimidazolone at room temperature is mixed with 200 vol. h of water. After adding 60 vol. 5 parts of caustic soda solution are clarified with active carbon and clarified in approximately 30 minutes with stirring, poured into a solution of 300 vol. including water, 41 vol. including glacial acetic acid and 80 vol. h t tinormal sodium borer at room temperature. The combination is quickly being pumped up. The mixture is boiled, thoroughly washed with water and dried at 60 ° C. The resulting yellow pigment is crushed and heated for 4 hours at 1.30 ° C with 450 vol. including dimethylformamide. Suction off the liquid, dimethylformamide is washed with methanol, and the dye is dried. A yellow pigment is obtained from soft particles of high intensity and pure tone. In polyvinyl chloride, lacquer, printing inks or dispersive paints, this dye gives light resistant colors of yellow color, flawless upper lacquer layers with very high strength against migration in PVC. Instead of dimethylformamide, the same weight of equal parts of pyridine or glacial acetic acid can be used. In this case, heated with reflux for 4 hours. Polyvinyl chloride processing is performed as follows: 16.5 wt. h. m. of a hychitel consisting of equal parts of dioctyl phthalate and dibutyl phthalate is mixed with 0.05 wt. including dye and 0.25 weight. including titanium dioxide, after which 3.3.5 wt. is added. h PVC. The mixture is rolled for 10 minutes on a two-roll mixer under frictional conditions, the resulting skin being cut with a spatula all the time and rolled again. In this case, one shaft is heated to 40 ° C, while the other has a temperature of 140 ° C. The mixture is removed in the form of sandpaper and pressed for 5 minutes at 1 ° C between two polished metal plates. Example 8. The combination is carried out according to Example 7. At the end of the combination, a dilute solution of sodium alkali is added to the mixture to a pH of 6.5-7. The mixture is transferred to a closed vessel where it is heated for 7 hours at. Sucked off, washed and dried. The resulting yellow pigment has almost the same strength properties as the dye of example 7. Example 9. The combination is carried out according to example 7; at the end of its dye is sucked off and washed with water. Next, cool the material, wash it with water and substantial. The resulting yellow pigment has the same strength properties as the dye of example 7. Example 10. 20.9 wt. including dimethyl ester of 5-aminoisophthalic acid is diazotized according to example 7. After that, 24 wt. including 5-acetoacetylaminobenzene and lightened with active carbon. The clarified solution is poured at room temperature into a solution of 300 vol. including water, 1.5 wt. including oleylaminoacetate, 41 about. including glacial acetic acid and 80 vol. Part 5 p. caustic soda solution. The suspension is heated to 60 ° C and introduced into the reaction at this temperature, with diazo-composition. At the end of the combination, an aqueous solution of 5 wt. including rosin soap, heated to boiling, kept at this temperature for 2 hours, sucked off, washed with water and dried at 60 ° C. A yellow pigment is obtained which in polyvinyl chloride gives slightly more transparent hues with a red tint than the dye of Example 7. Example 11. 20.9 wt. including dimethyl ester of 5-aminoisophthalic acid is mixed for about 1 hour with 80 vol. h. 5 n. hydrochloric acid, then diluted with 300 vol. h of water. The diazotization is carried out at 10 ° C with 20 vol. Part 5 of a solution of sodium nitrite solution is clarified with infusoric earth and a possible excess of nitrous acid is decomposed with a small addition of aminosulfonic acid. At 20 ° C, with this good mixing, this diazo solution can be poured into the acetic acid suspension in the acetic acid obtained by the following method: 26.1 wt. including 6-chloro-5-acetoacetylaminobenzimidazolone at room temperature is mixed with 200 vol. including water and dissolved in 60 vol. h. 5 n. sodium alkali. This solution is clarified with active charcoal and the clarified solution is stirred for 30 minutes in a mixture of 300 vol. including water, 41 vol. including glacial acetic acid and 80 vol. Part 5 p. caustic soda solution at room temperature. The combination takes little time. The mixture is boiled, sucked off, washed thoroughly with water and dried at 6: 0 ° C. The resulting yellow pigment is crushed and heated it for 4 hours at 130 ° C with 450 vol. including dimethylformamide. Again sucked off, washed dimethylformamide with methanol and the dye is dried. A yellow pigment of soft particles is obtained, having high strength and a clear shade. In PVC, varnish, printing