DE1768948C3 - Water-insoluble monoazo dyes, process for their preparation and their use - Google Patents

Description

N = N - CH - CO

NH-R ₃

where X is hydrogen, halogen or an alkyl group having 1 to 4 carbon atoms, R and R _{1 are} hydrogen or —CONH, but cannot have the same meaning at the same time, and R _{3 is} acetyl, propionyl or butyryl.

2. Water-insoluble monoazo dyes according to Claim 1 of the general formula

The invention relates to valuable water-insoluble monoazo dyes of the general formula

CH ₃

I.
CO

N = N-CH CO-NH

NH-R ₃

co

CONH ₂

wherein X is hydrogen, halogen or an alkyl group having 1 to 4 carbon atoms and R _{3 is} acetyl. Is propionyl or butyryl.

3. A process for the preparation of water-insoluble monoazo dyes according to claim I of the general formula

where X is hydrogen, halogen, in particular chlorine or bromine or an alkyl group having 1 to 4 carbon atoms, R and R _{1 are} hydrogen or - CONH, but cannot simultaneously have the same meaning and R _{3 is} acetyl, propionyl or butyryl, a process for their production and their use as pigment dyes.

Compared to Example 1 3 of Belgian patent specification 638 928, the pigment according to the invention shows mn one Carbonamidgruppc in the 5-position of the diazo component the better lightfastness; Likewise, the pigments with an acetylamino or butyrylamino-

group in place of the benzoylamino group from Japanese Patent Publication 22 396/66, 9. Table example of Example 4, known pigment superior in light fastness.

Preferred dyes are those of the general formula

CH ₃
CO

j (IJ)

CONH ₂

wherein X and R ₃ are as defined above

wherein X is hydrogen, halogen or an alkyl.

is a group with 1 to 4 carbon atoms. R and R ₁ The azo dyes according to the invention are generally hydrogen or —CONH ₂ , but do not mean formula I, are obtained by digi at the same time and azonium compounds of amines of the general R ₃ acetyl, propionyl or butyry! is, thereby 50 formula
characterized in that one diazonium compounds X
of amines of the general formula

NH,

(IH)

in which X, R and R _{1 have} the meaning given above, with acetoacetic anilides of the general formula

in which X, R and R _{1 have} the meaning given above with acetoacetanilides of the general formula

λ - \

1-R ₃ (IV)

CH ₃ ■ CO · CH, · CO · NH - <f ^> --NH-R ₃ 65 in which R _{3 has} the meaning given above,

^^ couples.

in which R, has the abovementioned meaning. Suitable diuzo components are, among others

sits, couples. 3-Aminohzocsäurcamid. 4-AmiiH) benzocic acid amide.

4-methyl-3-amino-knoic acid amide / L 3-methyl -4-amino-benzoic acid amide. 4-chloro-3-amino-benzoic acid amide and 3- (chloro-4-amino-benzoic acid amide.

The acetoacetanilides are l-acetoacetylamino-4-acetylaminobenzoL 1 -Accloacetylamino-J-propionylaminobenzene and l-acetoacelylamino-4-butyrylaminobenzene.

The coupling of the starting components is preferably carried out in weakly acidic to weakly alkaline run aqueous medium.

The dyes of the general formula 1 according to the invention are insoluble in water and are suitable as Pigment dyes are excellent for a wide variety of purposes, e.g. B. in pigment printing, for Pigmenting of paints and plastics, for dyeing synthetic fibers in bulk and for manufacture of printing inks. They are characterized by very good light and solvent fastness. From the series of dyes obtainable according to the invention, z. B. those as particularly valuable, in which X is chlorine or a methyl group and R 1 is the acetyl radical.

In the following examples, parts by volume are given in parts by weight in the ratio of millimeters to grams.

example 1

18 parts by weight of 1-acetoacetylamino-4-acetylaminobenzene are dissolved in dilute sodium hydroxide solution, prepared from 150 parts by weight of water and 3.2 parts by weight of sodium hydroxide. 16 parts by weight of nairium acetate are added to the solution. which is dissolved in 70 parts by weight of water. and 100 parts by volume of a 5% strength aqueous solution of the reaction product of 1 mole of alcohol with 20 moles of ethylene oxide, then diluted with water to 600 parts by volume. cools down to 10 and the 1-acetoacetylamino-4-acctylaminobenzene precipitates out of the alkaline soda solution by quickly adding 50 parts by volume of normal acetic acid. To this end, the ice-cold diazonium salt solution is run in, which is prepared from 12.4 parts by weight of 4-chloro-3-aminobenzoic acid amide by diazotics in a mixture of 150 parts by weight of water and 17.3 parts by weight of hydrochloric acid (d = 1.16) with 5 parts by weight of sodium nitrite will. The reaction mixture shows an acetic acid reaction. After the coupling has ended, it is heated to 90 to 100 and kept at this temperature for half a hour. The dye, which is isolated and dried in the usual way, is suitable for the production of printing inks, especially for textile printing, and for dyeing paints and plastic materials. The greenish yellow dyeings obtained have excellent solvent and overspray fastness properties and are distinguished by high light fastness properties

the end.

Example 2

10.9 parts by weight of 4-methyl-3-aminobenzoic acid in a mixture of 150 parts by weight of water and 17.3 parts by weight of hydrochloric acid (d = 1.16) are diazotized with 5 parts by weight of sodium nitrite at about 0 in the usual way. The diazonium salt solution is 18 parts by weight of 1-acetoacetylamino-4-acetylaminobenzene. which, as described in Example 1, is dissolved in alkaline soda and, after adding the amount of sodium acetate specified there, is treated with acetic acid

will fall. After the coupling has ended, the reaction mixture is heated to 90 to 100 for half an hour heated. The dye is then filtered off, washed on the filter with water and dried The greenish yellow colorations obtained with this dye are very good Solvents and light spots.

Example 3

The from 10.9 parts by weight of 2-methyl-4-aminobenzoic acid amide and 18 parts by weight of 1-acetoacetylamino-4-acetylaminobenzene Dye prepared according to Example 2 is filtered off after coupling is complete, washed on the filter with water and dried. This dye is the same as that described in Example 2 with regard to shade and fastness properties similar.

Yellow pigment dyes with similar properties are obtained by using those in the preceding Examples of chloro- or methyl-aminobenzoic acid amides mentioned as diazo components are replaced by 3-aminobenzoic acid amide, 4-ethyl -3-aminobenzoic acid amide, 4 - aminobenzoic acid amide, 3 - chloro - 4-aminobenzoic acid amide or 3-ethyl-4-aminobenzoic acid amide or if you use ais coupling component instead of the mentioned l-acetoacetylamino ^ -acetylaminobenzene for the production of the dyes 1-acetoacetylamino-4-propionylaminoben / ol used, and in each case the diazo components mentioned in Examples 1 to 3 were used.

Claims (1)

Patent claims: 1. Water-insoluble monoazo dyes of the general form! 4. Use of the dyes of claim 1 as pigment dyes. co