SU55969A1 - The method of obtaining vat dyes - Google Patents

Description

The invention relates to the field of the production of vat dyes. It is known that when heated in various organic solvents 1, 4, 5, 8-naphthalene-tetracarboxylic acid with an excess of aromatic o-diamine, its diaryl diimidazole derivatives are formed, which possess valuable dyeing properties and are used by industry as strong vat dyes.

Similar diimidisole dyes with unequal aryl residues are obtained by condensing acenaphthene-5,6-dicarboxylic acid: or naphthinedandione-dicarboxylic acid derivatives with o-diamines, followed by oxidation of the condensation products to naphthoylene-4,5-aryl azole-1, 8-di carboxylic acids and, finally, with the final interaction of the latter with other o-diamines.

It is also known that the same dyes, with unequal aryl residues, can also be obtained from naphthalene-tetracarboxylic acid by successive condensation of it with two unequal o-diamines.

In this case, the naphthalene-tetracarboxylic acid disodium salt is used and the reaction is carried out in an aqueous solution to form naphthoylenaryl-imidazole peridicarboxylic acid. Then, after it is separated from the reaction by-product (diamido-diarylimide, naphthalene-tetracarboxylic acid), it is condensed, as indicated above, with another o-diamine molecule in organic solvents or in an aqueous medium.

It will be understood that, if a second o-diamine identical to the first is taken into reaction, diimidazole derivatives will be the reaction products (Naft | alin-tetracarboxylic acid.

Thus, the method of obtaining these dyes can be carried out in the absence of organic solvents by two-step condensation: 1) by condensation of o-diamine in an aqueous medium with disodium salt 1, 4i, 5, 8-naphthalene-tetracarboxylic acid in naphthoylen-4, 5-aryl-imidazole 1, 8-dicarboxylic acid, with the release of the last of its salt, and 2) by condensation of naphthoylen-aryl-imidazole-pericarboxylic acid with the same

o-diamine to the corresponding naphthoylen-diaryl-diimidazole.

It is established that dyes of the general formula

/ NГ / Р

 nh

can be obtained in the absence of organic solvents in one time with quantitative yield by heating

1 mol 1, 4, 5, 8-naphthalene-tetracarboxylic acid (or its dianhydride) with

2 mol of o-diamine (or its salts) in an aqueous medium at a temperature above 100 °.

It has also been established that when 1, 4, 5,3-naphthalene-tetracarboxylic acid is replaced by 3, 4, 9, 10-perylenetetracarboxylic acid, the corresponding diaryldiimidazole dyes are formed.

Example 1. 304 weight. hours, 4, 5, 8 naphthalene-tetracarboxylic acid or 268 weight.h. its dianhydride (1 mol) and 216 wt. hours of o-phenylene diamine (2 mol) is heated for 5 hours to 140 ° in an autoclave with 2500 hours of water. The resulting dye is filtered and dried.

Output 387 wt. h. (94 / o theoretical). The dye is dissolved in concentrated sulfuric acid with a yellow-red color. From the brownish-green hydrosulfite cube it paints the blac in a bright and strong scarlet color. The dye is a mixture of two isomers and can be divided into orange (identical to the indanthrene or orange-orange GH) and bluish-red dyes by known methods.

P p "m: e p 2. 304 weight. hours 1,4, 5, 8-naphthalene-tetracarboxylic acid, 205 weight. including 4-chloro-o-phenylenediamine and 2500 water heated in an autoclave at 160-165 ° for 4 hours. The condensation product is filtered and dried.

Output 446 wt. including dye (.) theoretical), dyeing from hydrosulfite cube in brown-red color.

Example 3. 268 wt. including dianhydride 1,4, 5, 8-naphthalene tetracarboxylic acid, 304 weight. including 4-ethoxy-o-phenylenediamine (2 mol) and 2500 parts of water are heated at 140-150 ° for 5 hours in an autoclave.

A dye is obtained with a quantitative yield, which dye the cotton brown.

Example 4. When 1 mole of naphthalene-tetracarboxylic acid with 2 moles of 1,2 naphthylenediamine is heated in an autoclave in an aqueous medium up to 160 °, dark violet powder dissolves in a quantitative yield. in concentrated sulfuric acid with a red-violet color.

The dye dyes from hydrosulfite cube in brownish-purple color.

Example 5. 268 wt. including dianhydride 1, 4, 5, 8-paftalin-tetracarboxylic acid, 290 weight. including acetic acid-toluylenediamine and 2500 hours of water is heated in an autoclave to 150-160 ° for 5 hours. After filtering and drying, a red powder, soluble in concentrated sulfuric acid with a bluish-red color and dyeing cotton from a hydrosulfite cube in a brown-red color, is obtained with almost quantitative yield.

Example 6. 520 wt. .four. di-o-phenylenediamine salt of 1, 4, 5, 8-naphthalene-tetracarboxylic acid in 3000 parts of water is heated in an autoclave to 140 ° for 5 hours. A dye identical to that described in Example 1 is obtained in almost quantitative yield.

Example 7. 428 wt. Part 3, 4, 8, 10-perylene-tetracarbonyl. Acids

(1 mol) or 392 weight. including its dianhydride, 216 wt. including o-phenylenediamine and 3000h. Water is heated in an autoclave to 160-165 ° for 8-10 hours. The product of the reaction is dark blue with a greenish sheen. The crystals are filtered and dried.

Output 540 weight. dye dye (96 / o theoretical), which is dissolved in concentrated sulfuric KHCviOTe with

pure blue and from a purple hydrosulfite cube colors cotton in a reddish blue color.

Example 8. Using the equivalent amount of 4-chlorophenylenediamine instead of o-phenylenediamine in the conditions of example 7, a blue-violet vat dye is obtained with an almost quantitative yield.

The subject matter of the invention.

Claims (2)

1. A method for producing vat dyes by the interaction of aromatic polycarboxylic acids containing carboxyl groups in the peri-position, with aromatic ortho-diamines when heated, in an aqueous medium under pressure, characterized in that 1, 4, 5, 8-naphthalene-tetracarboxylic acid is used as polycarboxylic acids, or 3, 4, 9, 10-perylenetetracarboxylic acid. 2. Acceptance of the method according to claim 1, characterized in that instead of the mechanical mixture of the components, salts of the indicated acids with different ortho-diamines of the aromatic series are used.