DE102007021661A1 - vat dyes - Google Patents

Abstract

The present invention relates to vat dyes of the formula (I), wherein in the formula: A is the radical of the formula (II) $ F2 and B is the radical of the formula (III) $ F3 and m is a number from 0.5 to 1.5 and n is a number from 0.5 to 1.5, where m + n is a number from 1.8 to 2, processes for their preparation and their use.

Description

The Invention is in the technical field of vat dyes.

From the EP 0 057 375 A2 are known olive vat dyes which are obtained by reacting 1 mole of cyanuric chloride with a total of about 2.8 moles of a mixture of 2-amino-3,4-phthaloyl-7-bromo-acridone and 1-aminoanthraquinone, wherein the molar ratio between 2 Amino-3,4-phthaloyl-7-bromo-acridone and 1-aminoanthraquinone 1:> 1.5 (see especially Examples 1 and 9).

These Although dyes are characterized by good properties, you Olive green color usually does not match the Demands of the market, the blue olive to blue-green shades required.

Out For this reason, the dyes described above become common mixed with blue dyes or it will be used completely different dyes. When choosing this Dyes is from an application point of view as well a good infrared emission is important.

regrettably but are the candidate mixed dyes or alternatives Dyes are very expensive, so this procedure quickly reaches the limits the economic machinability encounters.

task Therefore, the present invention was to market products available to meet the requirements in terms of hue and infrared emission meet and are more economical.

It It has now surprisingly been found that this task is solved, starting from the above Products or procedures, the proportion of 2-amino-3,4-phthaloyl-7-bromo-acridone elevated.

worin
A für den Rest der Formel (II)

und
B für den Rest der Formel (III)

stehen und
m eine Zahl von 0,5 bis 1,5 und
n eine Zahl von 0,5 bis 1,5
bedeuten, wobei m + n eine Zahl von 1,8 bis 2 ist.The present invention thus provides vat dyes of the formula (I)

wherein
A is the radical of the formula (II)

and
B for the rest of the formula (III)

stand and
m is a number from 0.5 to 1.5 and
n is a number from 0.5 to 1.5
mean, where m + n is a number from 1.8 to 2.

The Molar ratio between 2-amino-3,4-phthaloyl-7-bromo-acridone and 1-aminoanthraquinone is thus 1: 1 to 1: 0.2.

In preferred compounds of the formula (I) m is a number of 1 to 1.5 and n is a number from 0.5 to 1, where m + n is a number of 1.8 to 2 is.

und mit 1-Aminoanthrachinon der Formel (V)

umgesetzt wird, wobei pro Mol Chlortriazin 1,5 bis 2,5 Mol der Verbindung der Formel (IV) und 0,5 bis 1,5 Mol der Verbindung der Formel (V) eingesetzt werden.The compounds of the formula (I) according to the invention can be prepared, for example, by reacting chlorotriazine with 2-amino-3,4-phthaloyl-7-bromo-acridone of the formula (IV)

and with 1-aminoanthraquinone of the formula (V)

is reacted, wherein per mole of chlorotriazine 1.5 to 2.5 moles of the compound of formula (IV) and 0.5 to 1.5 moles of the compound of formula (V) are used.

The reaction can, for example, analogous to that in the EP 0 057 375 A2 described method and is carried out in particular in an inert solvent such as chlorobenzene, dichlorobenzene or nitrobenzene, optionally in the presence of phenol. In addition, the reaction can also be carried out in phenol.

The Temperatures are preferably 80 to 150 ° C, in particular at 90 to 140 ° C.

The Reaction can be gradual by reaction of cyanuric chloride with first 1-aminoanthraquinone and then further with 2-amino-3,4-phthaloyl-7-bromo-acridone or in reverse order first with 2-amino-3,4-phthaloyl-7-bromo-acridone and then with 1-aminoanthraquinone or directly in the stew by reacting Cyanuric chloride with a mixture of 1-aminoanthraquinone and 2-amino-3,4-phthaloyl-7-bromo-acridone performed become.

The vat dyes of the invention general formula (I) are characterized by blue olive to blue-green Colors that meet the market requirements. The same applies to the IR remission.

This result is surprising in that it was unpredictable whether the compound of the formula (IV) would completely react with the chlorotriazine, ie the compounds according to the invention economically justifiable effort would be produced at all. Likewise, the IR remission properties were unpredictable.

The Dyes according to the invention can therefore advantageously for dyeing cellulose fiber-containing Materials, in particular of cotton are used.

there can all be used for vat fuels Dyeing be applied. These are exhausting described in the literature and known in the art.

example 1

A Mixture of 1200 g of phenol and 210 g of 2-amino-3,4-phthaloyl-7-bromo-acridone of formula IV (0.5 mol) and 46 g of 1-aminoanthraquinone of the formula (V) (0.21 mol) and 48 g of cyanuric chloride (0.26 mol) is homogenized at 80 ° C. and heated to 125 ° C. The reaction becomes five Stirred at 125 ° C for hours. After complete Turnover of the reactants, the reaction mixture to 70 ° C. cooled and diluted with 533 g of methanol and Stirred at 60 ° C for 20 min. The failed product is filtered, phenol-free with methanol and methanol-free with water and washed salt-free. After drying, 222.5 g of dye, which colors in blue-green tones.

Blue-tinged olive to bluish green-coloring products are also obtained when the procedure described in Example 1 is repeated with the following amounts: example Formula (IV) Formula (V) cyanuric chloride G mol G mol G mol 2 200 0.48 52 0.23 48 0.26 3 43 0.1 17 0.08 12 0.06 4 210 0.5 64 0.29 53.7 0.29 5 200 0.48 35 0.16 44 0.24 6 230 0.55 35 0.16 48 0.26 7 60 0.14 8th 0.04 12 0.06

Example 8

A Mixture of 300 g of phenol and 50 g of 2-amino-3,4-phthaloyl-7-bromo-acridone of formula (IV) (0.12 mol) and 11.4 g of cyanuric chloride (0.06 mol) Homogenized at 60 ° C and heated to 92 ° C. The reaction mixture is stirred for two hours at 92.degree. After complete conversion of the reactants, 11.5 g of 1-aminoanthraquinone of the formula (V) (0.05 mol) and heated to 140 ° C. and stirred at 140 ° C for three hours. Subsequently the reaction mixture is cooled to 70 ° C and diluted with 533 g of methanol and 20 min at 60 ° C. touched. The precipitated product is filtered, with methanol phenol-free and washed with water methanol-free and salt-free. To Dry 48.9 g of dye, in blue-green tones colors, received.

Example 9

A Mixture of 450 g of phenol and 17.5 g of 1-aminoanthraquinone of the formula (V) (0.08 mol) and 18.5 g of cyanuric chloride (0.1 mol) at 60 ° C homogenized and heated to 92 ° C. The reaction mixture is stirred for two hours at 92 ° C. After complete Reactant conversion is 80 g of 2-amino-3,4-phthaloyl-7-bromo-acridone of the formula (IV) (0.19 mol) and heated to 140 ° C. and stirred at 140 ° C for three hours. Subsequently the reaction mixture is cooled to 70 ° C and diluted with 300 g of methanol and 20 min at 60 ° C. touched. The precipitated product is filtered, with methanol Washed phenol-free, with methanol free of methanol and with 1% sodium hydroxide solution Washed phenol-free and salt-free. After drying, 79.6 g of dye, which colors in blue-green tones.

QUOTES INCLUDE IN THE DESCRIPTION

This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.

Cited patent literature

• EP 0057375 A2 [0002, 0012]

Claims (4)

Vat dye of the formula (I)

where A is the radical of the formula (II)

and B is the radical of the formula (III)

and m is a number from 0.5 to 1.5 and n is a number from 0.5 to 1.5, where m + n is a number from 1.8 to 2. Vat dye according to claim 1, characterized in that m is a number from 1 to 1.5 and n a number from 0.5 to 1, where m + n is a number from 1.8 to 2. A process for preparing a vat dye according to claim 1 and / or 2, characterized in that chlorotriazine with 2-amino-3,4-phthaloyl-7-bromo-acridone of the formula (IV)

and with 1-aminoanthraquinone of the formula (V)

is reacted, wherein per mole of chlorotriazine 1.5 to 2.5 moles of the compound of formula (IV) and 0.5 to 1.5 moles of the compound of formula (V) are used. Use of a vat dye according to claim 1 and / or 2 for dyeing cellulose fiber-containing materials.