DE1276255B - Process for the preparation of water-insoluble monoazo dyes - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY GERMAN AwA PATENT OFFICE

EDITORIAL

Int. Cl .:

C09b

C07c ' German class: 22a-l 12q-12 Number: 1276255 File number: P 12 76 255.9-43 (F 39783) Registration date: May 18, 1963 Display day: 29th August 1968

The subject of patent 1 213 551 is a process for the production of water-insoluble monoazo dyes, where amines of the general formula (I)

NH,

(D

in which X stands for a hydrogen, chlorine or bromine atom, diazotized and in an acidic medium with azo components of the general formula (II)

(II) Process for the preparation of water-insoluble monoazo dyes ^

Addition to the patent: 1213 551

Applicant:

Farbwerke Hoechst Aktiengesellschaft formerly Master Lucius & Brüning, 6000 Frankfurt

Named as inventor:

Dr. Helmut Gies, 6238 Hofheim; Dr. Helmut Lindner, 6000 Frankfurt-Sindlingen; Dr. Arthur Siebert, 6000 Frankfurt-Höchst

NH-CO

in the Ri an alkyl group, which was still by hydroxyl, In a further embodiment of this process Alkoxy or acyloxy groups can be substituted, now found that very valuable monoazo- and R2 denotes a cyanoalkyl or aralkyl radical, 25 dyes of the general formula (IV) are obtained, be coupled.

(IV)

wherein X and Ri have the meanings given above and R3 is a hydrogen atom or a Alkyl radical and R4 represents an alkyl radical if one the diazo compounds of the abovementioned amines of the general formula (I) in an acidic medium here with azo components of the general formula (III)

(III)

NH-CO

C-Xi C-O K4

in which Ri denotes an alkyl group through Hydroxy, alkoxy or acyloxy groups substituted CH2 CH CO R4

R ₃

can be, and R3 is a hydrogen atom or an alkyl radical and R4 is an alkyl radical, couples.

The new monoazo dyes obtainable according to the process dye as disperse dyes semi- and fully synthetic fibers, such as acetate silk and polyethylene terephthalate fibers, in purple to blue Tones and are suitable for setting black tones when mixed with other dyes. The dyeings obtained in this way are characterized by very good lightfastness and good heat-setting fastness the end.

Compared to the dye 2,4-dinitro-6-chloroaniline known from French patent specification 1,289,752 - ► 2- (N-4'-methyl-phenylsulfonylethylamino) -4-acetaminoanisole the dyes of a similar structure obtainable according to the process are characterized by better drawability on polyethylene

809 594/507

terephthalate fibers and a smaller shade difference the colorations in daylight and filament light.

example 1

21.7 parts by weight of 2,4-dinitro-6-chloroaniline are ' diazotized in the usual way in glacial acetic acid with nitrosylsulfuric acid. The diazo solution thus obtained leaves one added with stirring in one with 1 part by weight of sulfamic acid and 500 parts by weight of ice Solution of 26.4 parts by weight of 2 - [(8-acetyl-ethylamino] -4-acetaminophenetol run in 100 ml of 1N hydrochloric acid. Then the mixture is mixed with water diluted to about 3000 parts by volume and stirred for about 2 hours. ■ After that, the retired Dye of the formula

Cl

O, N

QC ₂ H ₅

f V_ _{N = N} _ <f V_ _NH _ _CH or — Co —CH ₃

NO ₂

NH - CO - CH ₃

filtered off, washed well with water and dried in the usual way. The dye obtained dyes polyethylene terephthalate fibers in navy blue shades of very from an aqueous dispersion good lightfastness and sublimation fastness.

If 2 - [ß -acetyl-propylamino] -4-acetaminophenetol is used instead of the azo components mentioned above, a dye with similarly good properties is obtained.

Example 2

18.3 parts by weight of 2,4-dinitraniline are diazotized in the usual way with nitrosylsulfuric acid. The diazo solution obtained is allowed to run into a solution of 30 parts by weight of hydrochloric acid 2 - [ß - acetyl - ethylamino] - 4 - acetaminophenetol in water with stirring. Ice is added for cooling. The mixture is then diluted to 3000 parts by volume with water and stirred for a further 2 hours. The dyestuff which has separated out is then filtered off with suction, washed until neutral and dried in the usual way. After drying, the dye is a blue-black powder which, from an aqueous dispersion on polyethylene terephthalate fibers, gives violet dyeings with very good fastness properties.

If the 2 - [/? - Propionyl-propylamino] -4-acetaminophenetol is used instead of the azo component mentioned above, in this way a dye with similarly good properties is obtained.

Example 3

26.2 parts by weight of 2,4-dinitro-6-bromaniline are diazotized in the usual way with nitrosylsulfuric acid. The resulting diazo solution is allowed to run into a solution, cooled with ice, of 30 parts by weight of 2- {ß- acetyl-ethylamino] -4-acetaminophenetol, which is cooled with ice. The mixture is slowly diluted to 3000 parts by volume with water and the precipitated dye is filtered off with suction after 2 hours, washed neutral and dried. It is a blue-black powder which dyes polyethylene terephthalate fibers from an aqueous dispersion in very lightfast and sublimation-fast dark blue tones.

If the 2 - [/ Msobutyro-ethylamino] -4-acetaminophenetoI is used instead of the azo component mentioned above, in this way a dye with similarly good properties is obtained.

65

Claims (1)

Claim: Another embodiment of the process for the production of water-insoluble monoazo dyes according to patent 1,213,551, according to which the diazo compounds of amines of the general Formula (I) O, N NH ₂ in which X is a hydrogen, chlorine or bromine atom, in an acidic medium with azo components the general formula OR ₁ ,H (II) NH-CO where Ri is an alkyl group, which is still through hydroxyl, Alkoxy or acyloxy groups can be substituted, and R2 is a cyanoalkyl or Aralkyl radical means coupling, characterized in that here in place of the Azo components of the general formula (II) those of the general formula (III) (ΠΙ)
^ CH ₂ -CH-CO-R ₄ NH-CO-CH ₃ in which Ri means an alkyl group, the can be substituted by hydroxyl, alkoxy or acyloxy groups, R3 is a hydrogen atom or an alkyl radical and R4 denotes an alkyl radical, is used. Considered publications:
French Patent No. 1,289,752. When the application was announced, a coloring table with explanations was laid out. 809 598/507 p. 68 O Bundesdruckerei Berlin