DE824816C - Process for the production of Kuepen dyes - Google Patents

Description

(WiGBl. P. 175)

ISSUED DECEMBER 13, 1951

C 1775 IVd I 22 b

Ciba A. G., Basel (Switzerland)

is used

It has been found that valuable vat dyes can be produced if one at least 2 mol ι - amino-5- (o-chlorobenzoyl) -aminoanthraquinone condensed to acid amide-like compounds.

The condensation to be carried out according to the present process to form acid amide-like compounds can in the simplest case be carried out in such a way that ι moles of a reactive! Derivative of a dicarboxylic acid, e.g. B. an acid halide with 2 moles of i-amino-5- (o-chlorobenzoyl) -aminoanthraquinone. It can e.g. B. the acid chlorides of aromatic dicarboxylic acids in which the carboxyl groups adhere to aromatic radicals, for example to one and the same benzene ring, or to different benzene rings ₎ which are linked to one another by simple bonds or by the fact that the benzene rings in question form a polynuclear System are condensed, which may optionally also have heterocyclic rings. Such dicarboxylic acids are, for example, iso- and terephthalic acid, diphenyl-4, ^ -dicarboxylic acid, naphthalenedicarboxylic acids, e.g. B. the 2,6-dicarboxylic acid, benzanthronedicarboxylic acids, z. B. as the 2, 6- and Bz-1, 6-dicarboxylic acid, anthraquinone-2, 6- or 2, 7-dicarboxylic acid, fluoranthene and thianthrenic dicarboxylic acid and diphenylene oxide and diphenylene sulfide dicarboxylic acid.

Acid amide-type condensation products are also obtained when the condensation is carried out with the aid of aromatic tricarboxylic acids, such as trimesic acid (benzene-i, 3,5-tricarboxylic acid), expediently in Form of a trihalide, e.g. B. of trichloride. In this case, 1 mole of a tricarboxylic acid trihalide can be used with 3 moles of I-amino-5- (o-chlorobenzoyl) -aminoanthrachijion or with 2 mol r -amino- 5- (o-chlorobenzoyl) -aminoanthra-

quinone and ι mol of another amino component, such as aniline, naphthylamine or i-aminoanthraquinone implemented. Quite analogously to the tricarboxylic acid trihalides with regard to the reaction and the dyes obtained also behave the Cyanuric halides, e.g. B. the cyanuric chloride, the formula

Cl-C C-Cl

N N

¹ p Cl

of which in the same way ι moles with 2 to 3 moles of i-amino-5- (o-chlorobenzoyl) -aminoanthraquinone to acid amide-like compounds reacted and any remaining halogen atom with any aromatic amine can be reacted.

The condensation can expediently at elevated temperature in high-boiling inert solvents, such as mono-, di- and trichlorobenzene, nitrobenzene or naphthalene, optionally in the presence acid-binding agents and / or catalytically active agents, such as pyridine, quinoline or dimethylaniline, be performed.

The products obtained are valuable, mainly yellow vat dyes, which are used to Partly due to the strength and / or purity of the color shade, partly due to good to excellent fastness properties distinguish.

The following examples explain the present invention without, however, restricting its scope. The parts are parts by weight, the percentages are percentages by weight, and the temperatures are given in degrees Celsius.

example 1

5.6 parts of i-amino-5- (o-chlorobenzoyl) -aminoanthraquinone and 1.5 parts of terephthalic acid dichloride are dissolved in 120 parts of anhydrous nitrobenzene Heated to the boil for 4 hours. After cooling, it is suctioned off, with nitrobenzene, then with benzene washed and dried. A yellow-red product is obtained which contains cotton from a brown-violet vat in real yellow tones · colors.

B e i β ρ i e 1 2

4.1 parts of i-amino-5- (chlorobenzoyl) -aminoanthraquinone and 1.5 parts of diphenyl-4,4'-dicarboxylic acid dichloride are heated to boiling ^{in 120 parts of anhydrous nitrobenzene for 1 hour.} After cooling, it is suctioned off, washed first with nitrobenzene, then with benzene and dried. A yellow-red product is obtained which dyes cotton from a brown-violet vat in real yellow tones.

τ, · ·,

Example 3

1.5 parts of isophthalic acid dichloride have 5.6 Part 1 -amino- 5 - (o-chlorobenzoyl) - aminoanthraquinone heated to boiling in 120 parts of nitrobenzene for 1 hour. After cooling down, suction takes place first washed with nitrobenzene, then with alcohol and dried. A yellow-red powder is obtained which Cotton from a brown-violet vat dyes real yellow tones.

Example 4

ι Part of trimesic acid chloride (benzene-1,3, 5-tricarbonisäuretrichloridi) and 4.2 parts of i-amino-5- (ochlorobenzoyl) -aminoanthraquinone boil for 4 hours in 60 parts of anhydrous nitrobenzene heated. After cooling, it is suctioned off, washed first with nitrobenzene, then with alcohol and dries. A yellow-red powder is obtained, the cotton from a black-violet vat in yellow Dyes shades of good fastness.

Example 5

6.1 parts of i-amino-5- (o-chlorobenzoyl) -aminoanthraquinone and 1 part of cyanuric chloride are dissolved in 120 parts of anhydrous nitro-enzene for 1 hour heated to boiling. After cooling, it is filtered off with suction, washed with nitrobenzene and then with benzene and dried. A yellow-red product is obtained, the cotton from a red vat in real yellow Tones colors. ,

Example 6

2 parts of cyanuric chloride and 8.2 parts of i-amino-5- (o-chlorobenzoyl) -aminoanthraquinone be in 240 parts of anhydrous nitrobenzene for 1 hour at 180 ° -185 ^0, then for 1 hour heated to boiling. After adding 2.4 parts of i-aminoanthraquinone, the mixture is heated to boiling for a further hour. After cooling, it is suctioned off, washed first with nitrobenzene, then with alcohol and dried. A yellow-red powder is obtained which dyes cotton from a brown-red vat in yellow shades of good fastness.

Example 7

1.5 parts of cyanuric chloride are mixed with 6.1 parts of l-amino-5- (o-chlorobenzoyl) -aminoanthraquinone and 240 parts of anhydrous nitrobenzene for 1 hour to 145 to 150 ⁰ , 1 hour to 155 to 160 °, then 1 hour to 165 to 170 ⁰ heated. Then ι part of aniline is added and the mixture is heated to the boil for 1 hour. u ₀ After cooling, it is suctioned off, washed first with nitrobenzene, then with alcohol and dried. A red-brown powder is obtained which dyes cotton from a brown-red vat in yellow-red shades of good fastness.

Example 8

3 parts Thianthrendicarbonsäure (see Swiss Patent 236231) is distributed together with 6 parts of thionyl chloride in 120 parts of o-dichlorobenzene and transformed by heating at 165 ⁰ in the Thianthrendicarbonisäuredichlorid. After the excess of thionyl chloride has been distilled off, 7.5 parts of 1-amino-5- (o-chlorobenzoyl) aminoanthraquinone are added and the mixture is heated to the boil for 1 hour. After cooling, it is filtered,

Claims (6)

washed out with o-dichlorobenzene, then with alcohol and dried. A yellow-red product is obtained, the cotton from a brown-violet vat in real yellow tones. Example 9 2 parts of fluoranthendicarboxylic acid (see German patent specification 729492) and 5 parts of thionyl chloride are distributed in 120 parts of nitrobenzene and through When heated to 160 °, it is converted into the corresponding acid chloride. After distilling off the excess 5.2 parts of i-amino-5- (o-chlorobenzoyl) -aminoanthraquinone are added to thionyl chloride and boiled for 34 hours. After cooling, it is filtered, with nitrobenzene, then with Benzene washed out and dried. A yellow-red product is obtained, the cotton from brown-violet Küpe colors in real yellow tones. Godfather χ ta χ sfrüch e: i. Process for the preparation of vat dyes, characterized in that min ^ at least 2 moles of 1-amino-5 - (o-chlorobenzoyl) -aminoanthraquinone condensed to acid amide-like compounds. 2. The method according to claim 1, characterized in that there are 2 moles of i-amino-5- (o-chlorobenzoyl) aminoanthraquinone with 1 mole of a reactive derivative of an aromatic Condensed dicarboxylic acid. 3. The method according to claim 2, characterized by the use of the acid chlorides. 4. The method according to any one of the claims ι and 3, characterized by the use of reactive derivatives of aromatic Tricarboxylic acids. 5. The method according to claim 1, characterized in that there are 2 or more moles ι -Amino-5- (o-chlorobenzoyl) -aminoanthraquinone condensed with ι mol of a cyanuric halide and a remaining halogen atom with a converts aromatic amine. 6. The method according to claim 5, characterized by the use of cyanuric chlorides Q 2512 12:51