DE1644623C3 - Anthraquinone dyes, their production and use - Google Patents

Description

CO _n

CH ₂ -N

(CH ₂ ) /

where R is a lower alkyl radical and η is a number from 5 to 11

4. Use of the dyestuffs according to Claim 1 for dyeing and printing wool, silk and synthetic polyamide fiber materials.

5. Use of dyes of claim 1 for dyeing and printing wool, silk and synthetic polyamide fiber materials.

The invention relates to water-soluble anthraquinone dyes of the general formula

CO.

CH ₂ -N

in which R is a lower alkyl radical and η is a number from 5 to 11, characterized in that anthraquinone compounds of the general formula

O NH,

SO ₃ H

OR

O NH

Methylol compounds or their derivatives of the general formula

X-CH ₂ -N

COv

(CH,

wherein X is a radical which can be split off with splitting off of HX, in particular a hydroxyl radical, a lower one Represents an alkoxy group, a chlorine or a bromine substituent, in the presence of acidic, preferred reacts strongly acidic condensing agent.

3. Modification of the process for the preparation of dyes according to claim 2, characterized in that that one l-amino-'t-bromo-anthraquinone ^ -

60 in which R is a lower alkyl radical and η is a number from 5 to 11.

The dyes are produced by reacting anthraquinone compounds of the formula

O NH,

45

O NH

SO ₃ H

/ v_

(H)

OR

wherein R represents a lower alkyl radical, with methylolamides or with how these react Compounds of the formula

55 CO

X-CH ₂ -N

(111)

(CH

2'n

where η is a number from 5 to 11 and X is a group which can be split off with splitting off of HX, in particular a hydroxyl, an alkoxy group, e.g. B. the methoxy or the ethoxy group, or a halogen atom, e.g. B. represents chlorine or bromine, in the presence of acidic condensing agents, especially strongly acidic condensing agents, such as 80 to 100% sulfuric acid,

3 * 4th

80 to 100% phosphoric acid or glacial acetic acid-hydrochloric acid-anthraquinone-2-sulfonic acid with amines of the formula mixtures, at temperatures from about -5 to about mel
+ 90 ° C, preferably from about 0 to about 30 ° C

Suitable compounds of the formula (III) are, for example, ₅

H, N

Il

C-CH,

CH,

HO-CH ₇ -N

CH ₃ O-CH ₂ -N

CH ₂ -CH ₂ -CH ₂ O

Il

C — CH ₂ CH,

CH ₂ -CH ₁ -CH,

C, H, O-CH, -N

Cl-CH, -N

Br-CH ₂ -N

(CHA '

HO-CH ₂ -N

(CH ₂ )

'2'K)

HO-CH ₂

(CH ₂ );

"5

55

6o

Another way of preparing the dyes of the formula (Π consists in the reaction of 1-amino-4-

CO

OV)

CK, - N

(CH ₂ ) ,,

where R is a lower alkyl radical and π is a number from 5 to 11

The lower alkyl radicals R are in particular those with 1 to 6 carbon atoms are considered

The new dyes are suitable for dyeing and printing leather, but especially wool and silk and synthetic polyamide fiber materials. On these materials, the dyes give a greenish blue Dyeings with very good light and wash fastness properties, good leveling properties and a favorable evening color.

In the following examples, parts represent Parts by weight; the temperature data are degrees Celsius.

example 1

110 parts of methylolcaprolactam and 315 parts are dissolved in 1000 parts of 96% strength sulfuric acid at 0 ° to 10 ° 1 -Amino ^ -p-anisidino-anthraquinone ^ -sulfonic acid and stirs for 20 hours at 18 to 20 °. It is then carried out on ice, the precipitated dye is suctioned off and washed with water. The dye paste is introduced into 5000 parts of water and neutralized with sodium hydroxide solution placed. The mixture is heated to 90 °, acidified with hydrochloric acid and filtered off with suction. After drying, 410 parts are obtained the dye of the composition

40

45 O NH

SO ₃ H

-O — CH,

CO-CH ₁ -CH,

CH, -N

CH, -CH, -1

which dyes wool, silk and polyamide fibers a greenish blue with good lightfastness and washfastness.

Example 2

170 parts of methylol-dodecanlaclam and 318 parts are dissolved in 1000 parts of 95% strength sulfuric acid at 0 ° to 10 ° 1 · Amino-4-p-ethoxyphenyl-anthraquinone-2-sulfonic acid and stirred for 20 hours at 20 °. One carries out on ice sucks off the precipitated dye and washes with water and with dilute sodium chloride solution. To

drying leaves 460 parts of the dye of the composition

NH,

SO ₃ H

O NH-

CH, N

(CH ₂ ), ',

"5

which dyes wool, silk and polyamide fibers a greenish blue with very good light and wash fastness properties. tam) -4-butyloxybenzene and heated to 60 °. The temperature is slowly increased over the course of 2 hours 80 ° and during this time a solution of 2.5 parts of CuCl in 30 parts of saline solution is added dropwise. To When the reaction is complete, the blue reaction product is filtered off with suction, washed with water and obtained drying 120 parts of the dye of the composition

O NH ₁

k:

\ ι

O NH - '<

SO ₃ H

-; CO -CHXH,

CH, -N _n / CH ₂

ch, ch, c'h.

Example 3 To 1500 parts of water, 87 parts of l-amino-4-

bromo-anthraquinone-2-sulfonic acid, 51 parts of sodium card- der wool and polyamide fibers greenish blue with bonat, and 60 parts of 1-amino-3- (N-methylene-suberolak- 25 good light and wash fastness dyes.

Claims (2)

sulfonic acid with amines of the general formula Patent claims:
1. Anthraquinone dyes of the formula H, N IO where R is a lower alkyl radical and π is a number from 5 to 11 2. Process for the preparation of anthraquinone dyes of the general formula