DE376815C - Process for the production of sulphurous Kuepen dyes of the anthraquinone series - Google Patents

Description

Process for the production of sulfur-containing vat dyes of the anthraquinone series. It has been found that the azomethine compounds of anthraquinone-2-aldehyde or its core substitution products when heated with sulfur in vat dyes be transferred, which have very good fastness properties. The sulphurization is made either by heating with sulfur to higher temperatures, alone or in a suitable inert solvent made. The addition of catalysts like iodine, it facilitates dye formation. The hue of the after this procedure available dyes is very diverse and ranges from yellow to red and purple to black blue.

The production of the azomethine compounds used as starting materials takes place in the usual way either by melting the components together or by heating in a suitable solvent such as glacial acetic acid, nitrobenzene, naphthalene.

The main properties of the in the following examples as Azomethine compounds not previously described are used as starting materials can be seen from the table below.

Example i.

A mixture of 10 kg of the azomethine compound obtained by the condensation of anthraquinone-2-aldehyde and p-toluidine of the formula: and .40 kg of sulfur is heated to 230-260 ° (outside temperature) for 5 hours. The melt, which is powdered after cooling, is treated with hot sodium sulphide solution to remove the excess sulfur. The solution of the dye in concentrated sulfuric acid is brown in color. With hydrosulfite and lye, the dye provides a brown vat from which cotton is dyed orange.

Example e.

10 kg of the azomethine compound obtained by condensation of anthraquinone-2-aldehyde and o-toluidine of the formula: are heated with 80 kg of naphthalene and 20 kg of sulfur with the addition of 0.3 kg of iodine for 7 hours to 210-220 ° (outside temperature). When the melt is diluted with naphtha, the dye separates out when it cools, which is treated with carbon disulfide to remove any sulfur that has precipitated out. The dye, which has been purified by dissolving from nitrobenzene, dissolves in sulfuric acid in a finite violet-red color. The vat is colored red-brown and produces yellow tones on cotton. solution knzen-staining Azomethine compound in o Appearance made of: after adding Küpe cotton from 'sulfur to 1'araform- aldehvd acid - Anthraquinone 2-aldehyde Lind p-Tohiidin ..... ... yellow crystals reddish yellow unchanged olive weak greenish yellow o-Toluidine ......... greenish yellow reddish yellow unchanged olive weak Crystals greenish yellow Benzidine (: z: i Mol.) ... orange-red orange unchanged brown-yellow-orange Crystals orange i-aminoanthrachi- non-2-aldehyde and p-phenylenediamine (i: i IM.). . . . . .... shiny bronze brownish blue olive violet red Crystals p-phenylenediamine (2: i 141o1.). . . . . . . . . shiny bronze yellow olive blue-green olive violet Crystals d-amino-d'-oxydiphe- nylamine ...... .... blue black olive blue olive blativio'.ett Example 3.

to hgr of the azomethine compound obtained by the condensation of two molecules of antliracliinon-2-aldehyde and one molecule of benzidine, of the formula: together finitely 100 kg \ aphthalin, 30 kg sulfur and 0.5 kg iodine are heated to 22-230 ° (outside temperature) for 5 hours. The still warm Schipelze is diluted with naphtha; the deposited dye is filtered off and finitely washed out carbon disulfide. The dye thus obtained dissolves in concentrated sulfuric acid with a brownish yellow color. Cotton is dyed in brownish-yellow shades from a brown-dyed vat. By chlorinating the finely divided dyestuff, a purely yellow-colored product is obtained.

Example d ..

10 kg of the azoniethin compound of (-ler formula: 8o kg of naphthalene, 2j kg of sulfur and 0.4 kg of iodine are heated to 230-235 '(outside temperature) for <hours. The dye is separated from the still hot melt by adding naphtha. It can be obtained in pure form by crystallization from high-boiling solvents. The solution of the dye in concentrated sulfuric acid is yellow-brown in color and turns blue-green when paraformaldehyde is added. With hydrosulfite and lye you get a red-violet vat from which cotton is dyed in blue-red tones.

A yellowish, red coloring dye with very similar properties arises when using the condensation of i-aminoanthraquinone-2-aldehyde and aniline-available azomethine compound.

Example 5.

A mixture of 10 kg of the azomethine compound of the formula obtained by condensation of one molecule of i-aminoanthraquinone-2-aldehyde and one molecule of p-phenylenediamine and 30 kg of sulfur is heated to 220-230 ° (outside temperature) for 6 hours. The melt, which is powdered after cooling, is desulfurized in the usual way by treatment with sodium sulphide. The dye is soluble in concentrated sulfuric acid with an olive brown color; when paraformaldehyde is added, the color of the solution changes to blue. Cotton is dyed in violet tones from the violet-dyed vat.

Example 6.

io 1g of the azomethine compound obtained by condensation of two molecules of i-aminoanthraquinone-2-aldehyde and one molecule of p-phenylenediamine of the formula: are heated with 125 kg of naphthalene and 3o kg of sulfur with the addition of 0.3 kg of iodine for 8 hours to 2r5-225 ° (outside temperature). After adding naphtha to the hot melt, the dye is deposited in the usual way and can be purified by treatment with boiling nitrobenzene. The properties of the dye are very similar to the dye prepared according to Example 5.

Example 7.

10 kg of the azomethine compound of the formula: are heated with 100 kg of naphthalene, 40 kg of sulfur and 0.5 kg of iodine for 7 hours to about 220 ° (outside temperature). The dye is precipitated from the hot melt with naphtha and extracted with hot sodium sulphide solution. It dissolves in concentrated sulfuric acid with a violet color, which turns black-blue with the addition of paraformaldehyde. The vat is dyed @brown - violet and produces strong black - blue dyes on cotton.

Claims (1)

PATENT-ANSPRUCII: Process for the production of sulphurous vat dyes the anthraquinone series, consisting in the fact that the azomethine compounds of anthraquinone-2-aldehyde or its core substitution products with Sch-, vefel, in the presence or absence of inert diluents, as well as of catalysts; like iodine to higher ones Temperatures heated.