SU1079656A1 - Process for preparing active vinylsulfonic azodyes - Google Patents

Abstract

A method for producing an active sulfonic acid azo-dye by means of a pattern of 4-vinylsulfo-Sh1L-2-aminoanisole and a combination of a pattern and a coating, which is designed in order to increase the stability of dyes to light and wet treatments. -naphthol-6,8-disulfonic acids or pyrazopone of the general formula. where I is methyl, carboxyl; 1 hydrogen or chlorine; position 3 or 4, with M-acyl-1,8-amino-naphtholdasulfonic acid dbooMv.Tbi i BUT inAe (L ato. $ 0 where Ac is acetyl, benero and L; position 3 or 4, with a ratio of 1: 9-9: 1, respectively) ate about 35

Description

This invention relates to an aniline coloring process, in particular, to a method for producing active vinyl sulfonic azo dyes for coloring materials from natural and synthetic polyides of identical fibers, as well as cellulose 1x materials and silk. Vinyl sulfonos 1e dyes are known, dyeing wool from neutral solutions. Synthesis of vinyl sulfonic azo dyes is carried out by alkaline treatment of a pre-synthesized metal complex (for example, chromium) -sulfoxtilsulfonic azo dye 1 The disadvantage of this method is the limited color gamut of individual dyes, among which scarlet and red dyes have insufficiently high light. color fastness (4 bars). A known method for producing scarlet active vinyl sulfone azo dyes with a wide range of color shades, according to which individual dyes are mixed 2 J. However, this is due to the complication of technology, due to the complexity of the process design, additional energy consumption and significant dye powder production. The closest to that proposed by the technical nature is the method of obtaining active viral sulfonic azo dyes by combining diazotized 4-vinylsulfonyl-2-amino-anisole with 2-naphthol-6,8-disulfonic acid CsJ. The known method allows to obtain the dyes of scarlet and red tones with insufficiently high resistance to soap and wet treatments, sweat and light (4 / 3-4; 4/3; 4/3 and 4 points, respectively). In addition, the range of colors of these dyes is limited. The aim of the invention is to increase the resistance of dyes to wet treatments and light while expanding the range of colors. This aim is achieved in that the process for producing aktivmlh vinilsulsonovyh azokrasite leu combination dia otirovannogo nilsulfoshsh 4-vi-2-lg1Inoanizola with 2-naphthol-6, 8-disulfoiislotoy combination is subjected to a mixture of 2-nafgol-6,8-disulfonic acid or pyrazolone total pho -pt-iypy. HC} (- B HO-c jj-if where R is methyl, carboxyl; RnR is hydrogen or. Chlorine; SPgH is in position 4 or 4, with N-acyl-1,8-a poly-naphthanicylphenyl acid common form Ily BUT TIANA where As acetyl, benzoyl; SOjH-in position 3 or 4, with a ratio of 1: 9-9: 1, respectively. "Example 1. To a cooled to a suspension of 3.58 g of 59.5% paste 4-vinyl sultfoto NILE- 2-namino anisole (0-, 01 g-mol) and 40 ml of water were added 6.3 MP of 4N hydrochloric acid solution and 5.0 ml of 2N sodium nitrite solution was diazoted as the nitrous acid disappeared. excess nitrous acid is removed with sulfamic acid. 0.42 g 86% of the 2-naphthol-6,8-di-sulfonic acid (0.00105 g-mol) is dissolved in 5 ml of water and 0.4 ml of 2N soda solution at pH 7.5-8.0, add 45 MP of N-acetyl-1, U-aminonaphthol-4, 6-disulfocyanolate solution, obtained by acetylation of 3.53 g of 92% 1,8-aminonaphthol-4,6-disulfonic acid (0.0095 g-mol) with acetic acid anhydride in the usual way, mix and add the diazo compound solution to the resulting solution of the azo composition mixture for 1015 minutes, maintaining the pH during the 6+ combination; 0.5 by adding the soda solution. The reaction time is 80 min. The dye solution is dried in the usual way at 40-60 ° C or in a fluidized bed dryer. The dry weight of the dye is 10.4 g. Wool fiber or fabric is modulated with a 1:50 modulus obtained. For this, a sample of the material is treated for 10 min at 40 ° C in a solution containing 5–10% of a glacial salt, 1% of a non-ionic extract, 3-5% of acetic acid (pH «5). Then the dissolved dye is injected, staining with 10 NMH at this Speratype, then the sieve is heated for 60 min: the solution is boiling and dyed with 45-60 NMH, cooled to 80 ° C, the ammonia solution is adjusted to pH 8-8, 5, treated with 10–15 shn, heated with warm water and dried. A red color with a hint of cotton is obtained, with good indications of the resistance of colors to wet treatments (5 points) and light (5 points). EXAMPLE 2. A cyaso compound is prepared as described in Example 1. 2.11 g of 86% 2-naphthol-6.8 disulfonic acid (0.0053 g-mol) is dissolved in 25 MP water. and 2.0 ml of soda solution at pH 7.5-8.0, 25 ml of M-acetyl-1,8-am solution of non-naphthol-4-diesulfonic acid, obtained by acetylation with 1.96 g of 92% 1, are added. , 8-aminonaphthol-4,6-disulic acid (0.0053 g-mol) with acetic anhydride in the usual way, mixed with 10 g-in and then combined, and dried as described in Example 1. 10.8 g of dry are obtained. dye. The dye obtained dye natural silk with a module 1:50. Dissolved dye and 10 g / l of glauber salt are introduced into the dye solution. KpapjeHHe starts at 20 ° C, after 30 minutes another 20-30 g / l of Glauber's salt is added and the temperature is gradually raised to 70-80 ° C for 20-30 minutes. The dyeing is continued at this temperature for 15 teiH, then a strong solution is gradually introduced into a solution of soda ash at the rate of 2 g / l and the mixture is continued for another 40 minutes. After that, the fabric is washed with warm water and treated with a solution of oleic acid. at 60 C and the bath module 1:50 for 15. This is followed by flushing and treatment in a solution of acetic acid, (O, 6 MP of glacial acetic acid in 1 liter of solution) for 5 minutes at room temperature dp brightening. Then the fabric is wrung out and dried. A bright red color with a bluish tinge with good indicators of resistance to wet treatments (5 points) and light (5 points) is obtained. Example 3. A diazo compound was prepared as described in Example 1. 3.8 g of 86% 2-naphgol-6,8-dicalt) Oxypots (0.0095 g-mol) were dissolved in 45 MP of water and 3.6 ml 2 n. a solution of soda at pH 7.5-8.0, add 5 ml of a solution of M-acetyl-1,8-amino-naphthol-4, 6-disulfonic acid, obtained by acetylation with 0.39 g of 92% 1.8-amino-naphthol-D, 6 -disulfonic acid (0.00105 g-mol) with acetic anhydride in the usual way, stirred for 10 minutes and then combined and dried as described in example 1. Obtain 10.1 g of dry dye. The obtained dye is used for printing natural silk. A printing ink containing 30 kg of sodium alginate dye (10%), 10 g of ludigol, 15 g of sodium bicarbonate in 1 kg is applied to the fabric of natural silk, dried, treated in a mat of grape saturated steam for 15 minutes at 102–103 ° C, with cold water and then with warm water and treated with solutions of oleic soap (7.5 g / l in terms of 40% product) at 60 ° C and a 1:50 module within 15 min Finally, the tissue is washed and treated in an acid solution (0.6 ml of glacial acetic acid in 1 liter of solution). For 5 at room temperature, wring out and dry. A scarlet color with a yellowish tinge and good indicators of resistance to wet treatments (5 points) and light (5 points) is obtained. Example 4. A diazo compound is prepared as described in Example I. 0.37 g of 72.6% 1- (4-sulfophenyl) -; 3-methyl-5-pyrazolone (0.00105 g-mol) is dissolved in 3 MP of water and 2 ml of 2N. a solution of soda at pH 7.0-7.5, add 45 ml of a solution of N-acetyl i 1,8-aminonaphthol-4,6-disulfonic acid, obtained by acetylation of 3.53 g of 92% 1,8-aminonaphthol-4 , 6-disulfonic acid (0.0095 g-mol) with acetic anhydride in the usual way, stirred for 10 minutes and then combined and dried as described in Example 1. Get 9.4 g of dry dye.

The resulting dye is dyed cotton fabric. The fabric is impregnated with a solution containing 1 l, g: dye 15; Urea 100, wetting agent NB-1, soda ash 20. Then press on the press until the fabric mass increases by 80% compared to the air dry weight, dried at 70 C. After drying, the dyed fabric is steamed with a saturated steam in a mattress at 101-103 C for 3 minutes, in cold running water to colorless industrial waters, in boiling disilphirated water with a 1:30 bath module for 15 minutes, are boiled for 15 minutes with a solution of non-ionic wet preparation (2 g / l) or oleic Nbma ( solution of 7.5 g in terms of 40% product) at m muzzle bath 1:30 prom.1vayut in warm and cold tap water, drained and dried. The dye paints cotton fabric in red with a blue tint with a good 1 and the indicator in the stability of A wet treatments (5 points) and light (3 points)

EXAMPLE 5: 1/1 compound is obtained as described in Example 1. 1.85 g of 72.6% 1- {4-sulfophenyl) 3-methyl-5-pyrazolone (0.0053 g-mol) dissolved in 15 ml of water and 10 ml of 2N. a solution of soda at pH 7.0-7.5, added kgg 25 ml of a solution of N-acetyl1, 8-aminonaphthol-4,6-disulfonic acid, obtained by acetylation of 1.96 g of 92% 1.8-amino-naphthol-4.6 disulfonic acid (0.0053 g-mol) with acetic anhydride in the usual way, stirred for 10 minutes and then combined and dried as described in Example 1. 9.8 g of a dry dye are obtained. Dyeing is carried out as described in Example 1. A scarlet color is obtained with a good indicator of resistance to wet treatments (5 points) and light (5 points).

Example 6. Diazocompound coupled as described in example 1.

3.33 g of 72.6% 1- (A-sulfophenyl) -3-metkl-5-pyrazolone (o, 0095 g-mol) is dissolved in 27 MP of water and 18 MP 2 n soda solution at pH, 5, add 5 ml of N-acetyl-1,8-aminoneFtol4, 6-disulfonic acid solution, obtained by acetylation of 0.39 g of 92% 1,8-aminonaphthol-D, 6-disulfonic acid (0.00105 g-mol) acetic anhydride in the usual way, mix fO min and then combined and dried, as described in example 1. Get 9.9 g of dry dye. Dyeing is carried out as described in Example 1. Obtaining a golden yellow color with good resistance to wet treatments (5 points) and light (5 points). I

Under similar conditions, obtained

dyestuffs with other materials have been added (i (see table).

Table continuation

7

eight

9

ten

eleven

12

As follows from the examples, the proposed method allows to obtain dyes that dye natural fibers in scarlet and red colors of various shades, with a high resistance of colors to the action of light (by 1. point) and wet treatments (by 1-1.5 points ).

In addition, the pre-burned method makes it possible to obtain scarlet and red dyes in a wide range of hues, while there is no need to use intermediate

products. The proposed method also makes it possible to obtain syozoic dyes directly on the plants that are supplying active colors. Tailors, without substantial costs for additional equipment and energy consumption, when mixing powders of individual dyes, vary the shades of dyes by combining with two or more AZ components and reduce the costs of labor protection measures associated with sawing dye powders when they are mixed. .

Claims (1)

METHOD FOR PRODUCING ACTIVE VINYL SULPHONIC AZO-DYES by combining diazotized 4-vinylsulfonyl-2-aminoanisole with 2-naphthol-6,8disulfonic acid, characterized in that, in order to increase the resistance of dyes to light and wet treatments when expanding the color spectrum, 2 -6,8-disulfonic acid or pyraz of an elephant of the general formula _ nS - ci- ¹ over where I am ⁴ -. methyl carboxyl; H ² and hydrogen or chlorine; SOjH - at position 3 or 4, with N-acyl-1,8-amino-naphtholdi sulfoalki with a common Foomchly no keel slot * where Ac is acetyl, benzoyl; SO ^ H-b position 3 or 4, with a ratio of 1: 9-9: 1, respectively.