DE1644231C - Water-insoluble monoazo dye and its use for inks and printing - Google Patents

Description

1 2

The present invention relates to a new, valuable, water-insoluble monoazo dye of the formula

H ₃ COOC _X NH.

I f- ^CH ° / co

^ ", N = N-CH-CO-NH, j> HN

H ₃ COOC

and a process for its preparation by drawing component 5-acetoacetylamino-benzimidazolone

5-Amino-isophthalic acid dimethyl ester diazotized and the dye of the present invention through

couples with 5-acetoacetylamino-benzimidazolone. better lightfastness or by a

The coupling reaction can be carried out in a known manner with better solvent or migration, in particular with an aqueous 15 fastness or by a better heat medium, expediently in the presence of a nonionic resistance of the dyeings.
The dyestuff has a hue that is similar to that of the normal agent. Corresponds to RAL 1016 to achieve a better grain yellow color. In contrast to the nature of the pigment, it is beneficial to show the dyes, for example, to heat them from the mixture for some time, for example to 10 Belgian patent specification 622 476, table example 36 or cook under pressure at temperatures above on page 12 and 646 790, Example 1, has become known to maintain 100 ° C., if necessary in the presence of a solvent that is very different from the red or orange organic solvent, such as dichlorobenzene or a shade shifted towards. The one from the Belgian resin soap. U.S. Patent 612,657, Example 1, known dye

To achieve particularly pure and genuine coloration, »5 shows a greener shade than the one according to the invention.

gen it is expedient to use the dye according to the Kupp according dye and also has a poor one

suction and as a moist press cake or in bleeding and migration fastness.

Form of the dried and powdered dye. 11th

with organic solvents such as pyridine, di- B e 1 s ρ 1 e 1 1

methylformamide, alcohol, glacial acetic acid, glycol mono- 30 20.9 parts by weight of 5-amino-isophthalic acid dimethyl

Ethyl ether, chlorobenzene or glycol under reflux ester are about 30 parts by volume of 5 η hydrochloric acid

or to heat under pressure at an elevated temperature. stirred for one hour and then mixed with 300 vol-

The preparation can also be diluted in the presence of a carrier part of water. It is diazotized at 10 ¹ C with

materials, for example barite. 20 parts by volume of 5N sodium nitrite solution, clarifies with

The new pigment dye is suitable for the production of diatomite and removes any excess of printing inks for the preparation of dye in nitrous acid with a little amidosulfonic acid.
lacquers and dispersion paints, for dyeing This diazo solution is allowed at about 2O ⁰ C under rubber, and natural and Kunsttoffen good stirring to an acetic acid suspension of the synthetic resins. The new dye is suitable for flow azo component, which was made in the following way for pigment printing on a substrate, 40:

in particular a textile fiber material as well as 24 parts by weight of 5-acetoacetylamino-benzimidazo other sheet-like structures, such as, for example, 200 parts by volume of paper at room temperature. It can also be mixed with water for other purposes and dissolved by adding 60 parts by volume, for example in finely divided form for coloring 5η sodium hydroxide solution. This solution is clarified with active rayon made of viscose or cellulose ether and the clarified solution is mixed in about 30 minutes with esters, polyamides, polyurethanes, and then stirred into a solution of 300 parts by volume of polyglycol terephthalates or polyacrylonitrile in the water, 41 parts by volume of glacial acetic acid and 80 parts by volume of spinning pulp or / to dye paper used 5 η-sodium hydroxide solution dripped in at room temperature,
will. The coupling is ended immediately. You bring that

The dye can be in the media mentioned 50 coupling mixture for boiling, sucks off. washes

Due to its favorable theological properties - thoroughly with water and dries at 60 C. That

work well. The colorations obtained have the yellow pigment obtained is powdered and with

good light, wet and migration fastness. 450 parts by volume of dimethylformamide for 4 hours

They are heat-resistant and heated against the influence of 130 ° C. Subsequently, the Resistant to chemicals such as solvents. 35 Dimethylformamide washed off with methanol and The dye from German Patent 1,227,585 has been dried. A yellow pigment is obtained

Monoazo dyes are already known, to their origin of soft grain, good color strength and pure

"Sharing the same azo component, the 5-aceto shade, fn polyvinyl chloride, a varnish, a print"

acelylamino-benzimidazolon, is used and the paint or a dispersion paint is incorporated,

from the dye of the present invention by βο yellow dyeings of high lightfastness are obtained,

the use of other diazo components with “perfect fastness to overcoating and very good

divorce. Compared to these known dyes. 1, fastness to bleeding in polyvinyl chloride,

For example, the monoazo dyes from the diazo «Instead of dimethylformamide one can use the same

Use components 1 "Amfno-2" methyl-4 "chlorobenzene or amounts by weight of pyridine or acetic acid. In

3'Ammo-4-chloro-enzamide or 1 "amino-2" nitroben "it is heated in this case for 4 hours under reflux,

zol odur 1 * Amino'2 <chlorobenzene or l-Amino-2-me- Processing in polyvinyl chloride takes place at «

Ethylbenzene or l-amino'2-methoxy-benzene or, for example, by the following process; 16.5 Ge "

l'AmiMO'2 "niiro'4 * nieiliylbenzol and the Azokont" wiehtsteile a "plasticizer mixture, consisting

from equal parts of dioctyl phthalate and dibutyl phthalate, are mixed with 0.05 part by weight of dye and 0.25 part by weight of titanium dioxide. Then 33.5 parts by weight of polyvinyl chloride are added. The mixture is rolled for 10 minutes on a two-roll mill with friction, the skin that forms being continuously cut up with a spatula and rolled up. Here, the one roller at a temperature of 40 ° C, the other kept at a temperature of 140 ⁰ C. The mixture is then peeled off as a skin and pressed between two polished metal plates ^{at 160 ° C. for 5 minutes.}

Example 2

The coupling takes place in the manner described in Example 1. After the coupling has ended, however, the coupling mixture is adjusted to a pH of 6.5 to 7 by adding dilute sodium hydroxide solution, placed in a closed vessel and ^{heated at a temperature of 150 °} C. for 7 hours. It is then filtered off with suction, washed and dried. A yellow pigment is obtained which has practically the same very good fastness properties as the dye prepared according to Example 1.

Example 3

The coupling is carried out in the manner described in Example 1, and when the coupling is complete, the dye is filtered off with suction and washed with water. This wet dye is stirred with 300 parts by weight of ethyl alcohol and heated for 5 hours at 15O ⁰ C in a closed vessel. S is then cooled, washed with water and dried. The yellow pigment obtained corresponds practically to the dye obtained according to Example 1 in terms of its fastness properties.

_J0 B bis ρ ί e I 4

20.9 parts by weight of 5-aminoisophthalic acid dimethyl ester are diazotized in the manner described in Example 1. Likewise, there is 24 parts by weight of S-acetoacetylaminobenzene dissolved according to Example 1 and clarified with charcoal. This clarified solution is left with Room temperature in a solution of 300 parts by volume of water, 1.5 parts by weight of oleylamine acetate, 41 parts by volume Pour in glacial acetic acid and 80 parts by volume of 5 n soda! The suspension obtained is heated to 60.degree heated and coupled with the diazo solution at this temperature. After the coupling is over, you give an aqueous solution of 5 parts by weight of resin soap added, heated to a boil, kept for two hours Boil, then vacuum, wash with water and dry at 60 ° C. A yellow pigment is obtained, which gives slightly more reddish and more transparent colors in polyvinyl chloride than the one according to the example! obtained dye.

Claims: 1. Water-insoluble monoazo dye of the formula

H ₃ COOC

CH ₃ CO N = N - CH - CO - NH CO

NH

H ₃ COOC

2. Use of the monoazo dye according to Claim 1 for dyeing or printing Rubber, plastics, natural or synthetic resins, textile fiber materials or paper, or as a coloring component of printing inks, color lacquers or emulsion paints.