SU1100292A1 - Acid diazo dyes based on 1-(n-(2,5-dichloroaniline-4-sulfonyl)-amino-)8-naphthol-3,6-disulfonate for polyamide fibers - Google Patents

Abstract

Acid disazo-dyes or disodium salt base

Description

to

with

Isd

This invention relates to an aniline polymerization, in particular to novel acidic disazo-dyes based on disodium salt of T-N - (2,5-dichloroaniline-4-sulfonyl) -amino-8-naphthol-3,6-disulfonic acid, suitable for dyeing polyamide fibers

in red tones.

The closest in chemical structure to the proposed dyes is an acid disazo dye based on a K-acid derivative of the general formula

BUT NH Og

, -K K- / Ls1nz (1) (acidic 1 red 158, C. 3. - 20530 The method for preparing this dye by diazotizing an aniline mixture with P-toluidine and then combining with (2-hydroxinaftapine-6-sulfonyl) -amino7- 8-naphthol-4,6-disulfonic acid (A) 1 J. However, this dye is not sufficiently characterized by high resistance to light, distilled water and sweat. Furthermore, the method of obtaining a known dye is technologically difficult due to the difficult accessibility of the A-component A, its technology and source intermediates IfOjgf where R is hydrogen or methyl R is the residue a current of 2-phenylindole or N, N-DI- (jb -oxyethyl) -m-toluidine. The method for producing dyes of the formula (It) is based on the diazotization of aniline or p-toluidine and after the next combination with (2,5-dichloro aniline -4-sulfonyl) -amino -8-naphthol -3; 6-disulfonic acid in alkaline cp .. The resulting monoazo dye is newly diazotized and combined with 2-phenylindole, H, L-di- (| b-hydroxyetht) -m-toluidine or another azo-component that does not contain groups that promote dissolution in water. Pollenized disazo dyes are isolated in a known manner, for example, to obtain 2-hydroxy naphthoic acid and K-acid (1-amino-8-naphthol-4, 6-dis-acid). The purpose of the invention is the preparation of new acid disazo dyes based on disodium salt 1 N- (2,5-dichloroaniline-4-sulfonyl) -a-8-naphthol-3, 6-disulfonic acid for polyamide fibers according to a simpler technology with enhanced resistance to light , distilled water and sweat. This goal is achieved by a new structure of acid disazocolines, expressed by the general formula K-N-R, by acidification or salting out the cooks. The dyes are used for dyeing as such or in the form of outlet forms containing sodium sulfate, dextrin, dispersants and other fillers. The original (2,5-dichloroaniline-4-sulfonyl) -amino-8-naphthol-3,6-disulfonic acid is obtained in good yield by condensation of 1-amino-8-naphthol-3,6-disulfonic acid (ASH-acid) with 2, 5-dichloroaniline-4-sulfonyl chloride in a weakly alkaline medium. Example 1. 10.7 g of p-toluidine are dissolved in 30 ml of hot water and 25 MP of concentrated hydrochloric acid, cooled with ice addition to 0 ° C and 7 g of sodium nitrate are diazotized in 35 MP of water. 54.25 g of disodium salt of (2,5-dichloroannlin-4-sulfonyl) aminoJ-8-naphthol-3,6-dicylic acid and 15 g of soda dissolved in 250 ml at 0-10 ° C, poured a solution of diazotized h - toluidine, stirred for 3.0 minutes, salted out with 10% sodium chloride by volume of the reaction mass, and 50.2 g of monoazoxy dye was filtered off. 33 g of monoazo dye is dissolved in 1000 mil of water, 55 ml of concentrated hydrochloric acid are poured, cooled to, 3.5 g of sodium nitrate are diazotized in 50 ml of water and stirred for 30 minutes, a solution of 10-g 2-feiylindole is poured into the dissolved diazo monosorbent 900 w of acetic acid, stirred for 2 hours, diluted with 1500 ml of water, heated to, salted out with 10% sodium chloride by volume of the reaction mass. and filter A.3 g disazokrasitel, coloring nylon in yellow-red color with light resistance of 5 points. Found,%: C 48.57; H 2.97; se 8.00; , 8.26-, N 8.91, 8.86;, S 9.57 991. Calculated,%: C 48.80; H 2.64 C 7.80-, N 9.25-, S 10.25. Example 2. Similarly, p-toluidine is diazotized and combined with d sodium salt, 5-dichloranium lin-4-sul фон phonyl) -amino-8-naphthol-3, -disulfonic acid, and then the resulting monoazoxygene is diazotized as described in Example 1. К 10 g of N, N-di (| 5-hydroxyethyl), m-trluidin are poured into 100 m of acetic acid in a solution of a diazotized monoazohydrate, -mixed 1 hour, 200 g of salt are salted out, and 41 g of disapaborous red color is added to filter out; with light resistance 5 points. Found,%: C 43.83 H 3.77; Cr 7.93-, 7.86-, N 8.68-, 8.54; S 10.7 10.58. C34 "3oC NfeNa20iiS3-H20 Calculated,%: C 43.92; H 3.47; CC 7.63-, N 9.04; S 10.34. Similarly to the above examples, by diazotization of aniline with 1-CN disodium salt (2,4-dichloroaniline-4-sulfonyl) -amino-3-8-naphthol-3, 6-disulfonic acid, followed by 2 diazotization of the resulting monoazoxygene and combining with different azomatizing components, the resulting output materials were used as the final result. Examples of P3-azo-compound 2phenylindol, color of color on nylon is yellowish-red, resistance to light is 5 points. Found,%: C, 48.11; H 2.21, C 8.64; N 9.85, S 11.17. Sb 2-iC «p t 2 S3 Calculated,%: C 48,32; H 2.48; Ce 8.41; N 9.95; S 11.37. EXAMPLE 4, A-Composite M, N-di- (p-oxystil) -m-toluidine, the color of the nylon is red, resistance to light. 4-5 points. Found,%: C 52.30; H 3.21; All 9.65; N 10.90; S 12,17, SzzN2, Se.2M, Na20,, 8h Calculated,%: C 52.45; H 3.57; All 9.40; N 11.12, S 12.31. Example 5. A sample of knitted fabric made of textured polyamide (elastic) is treated for 20 minutes with a bath containing 4% equalizer (a mixture of anionic alizarin oil and non-ionic preparation OP-10 in the ratio 5: 1) and 4% ammonium sulphate to pH 6 (here and further percentages are based on the weight of the material being painted). Bath module 1:50. Thereafter, 1% of the dye obtained in Example 1 is added in the form of a 1% solution, heated to boiling and dyed for 1 hour per boil. The painted sample is removed from the bath, washed with warm and cold water and dried. A red-colored sample with a yellowish tinge is obtained. The resistance of color to physicochemical effects is characterized by the following indicators according to GOST 9733-61; without hardening - after hardening To light K distilled4 / 4-5 / 5 / 4-5 4/5/5/5 bath water To a solution of soap at W ° C 4/5/5/5 4/5/5/4- 5 4 / 4-5 / 5/4 4/4/5/4 K sweat. Acid red 2-acid acid bright red-anthraquinone C 8 C are used as base dyes for capron dye. Compared to these base dyes (see table), the proposed dyes have a much more intense color (due to the presence of two chromophore systems in one molecule), greater resistance to light (1 point) and higher resistance to distilled water and sweat.

The main precursors for the proposed disazo dyes (aniline, and -toluidine, Al-acid, 2,5-dichloroaniline, 2-phen lindol, and N, N-di (p-hydroxyethyl) -m-toluidine) are produced by industry in industrial scale. and at an inexpensive price.

Taking into account the simplicity and mastering of the technology of the processes used (sulfochlorination, diazotization, azo coupling, etc.) and good yields in individual stages, it can be expected that the cost of the resulting dyes will fit into the usual cost of acid dyes used to dye wool. (an average of about 4,500 rubles per ton of dye) and half the cost of disperse dyes (about 9 thousand rubles per ton), and at the same time improving the stability of the obtained colors.

Comparative data on the durability of paints offered by dyes and similar in color to dyes on textured polyamide are given in the table.

As follows from the presented data on the color properties of the proposed and well-known dyes, the proposed dyes have increased resistance to light, distilled water and sweat.

In addition, their technology is much simpler due to the readiness of the starting intermediates for their preparation.

0.7

Red with a yellowish tinge

Red with a bluish tinge

0.8

Red with a yellow tint

Red

0.8 with a bluish tint

Acid

Red red with yellow

158 (2Ж) 1J 2.0 tinted GOST 9733-61)

5 4 / 4-5 / 5 / А-5 4/5/5 / 4-5 4/4/5/4 5 4/5/5/5 4/5/5/5 4 / 4-5 / 5 /four

5 4 / 3-4 / 4/4 4/3/4/4 4/3/3/3 5 4/4/4/4 4/5/5/5 4/4/4/4

4/4/5/5/5

A / 4/5/5/5

4/5/5/5 4/5/5/5 4/5/5/5 4/5/5/5

3/4/5/5/53/4/4/5

4/4/4/5/5

3/4/5/5/54/4/5/5 4/4/5/5/5 4/4/3/4

4/5/5/53/2/2/2 4/4/4/4

4 /, 5/5/54/2/3/4 Note. Top line - without hardening; bottom line - after processing by the fixer by the pre-reserved NPA.

Claims (1)

<claim-text> <table border = "1"> <tbody> <tr> <td> Acid </ td> <td> 3.5 </ td> <td> Red </ td> <td> 4 </ td> <td> .4 / 2/3/4/4 </ td> <td> 4/5/5/5 </ td> <td> 4/2/3/3/4/4/5 </ td> </ tr> <tr> <td> bright red anthraquinone </ td> <td> </ td> <td> with blue tinged </ td> <td> 4 </ td> <td> 4/4/4/5 </ td> <td> 4/5/5/5 </ td> <td> 4/4/5/5 </ td> </ tr> <tr> <td> H8C (GOST 1085064) </ td> <td> 4 </ td> <td> </ td> <td> </ td> <td> </ td> <td> </ td> <td> </ td> </ tr> </ tbody> </ table> <claim-text> Note. Top line - without hardening; the bottom line - after processing by the fixer by the pre-reserved NLA. </ claim-text>