JPS5819698B2 - Monoazoganryo no Seihou - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The object of the present invention is a monoazo pigment of the following formula, which is prepared by diazotizing p-nitroaniline by a known method and coupling it with 5-acetoacetylamino-benzimidacylone. Manufactured by

Furthermore, the present invention uses the crude pigment obtained above in water and (
or) It relates to a method for producing a monoazo pigment in the desired form represented by the above formula by heat treatment at 80 to 180°C in the presence of an organic solvent.

The pigment can be produced by coupling a solution of the diazo compound with a coupling component which is present in the form of a fine dispersion in a weakly acidic medium, or by coupling an alkaline solution of the coupling component with a previously prepared solution of sodium acetate. This can be carried out by flowing into a solution of the diazo component which has been added to a pH value of 5 to 6.

Another possibility for carrying out the coupling is to flow the solutions of the diazo component and the coupling component together into a sodium acetate-acetic acid buffer mixture.

In all these operating methods, it is preferred to operate in the presence of cationic, anionic or nonionic surface-active compounds.

In order to create a pigment form that is optimal with respect to particle flexibility, tinctorial strength, covering power and processability in lacquers and synthetic resins, the pigments obtained must be subjected to a thermal aftertreatment according to the invention.

The aqueous pigment suspension is prepared in water at a temperature of 80 DEG to 150 DEG C., optionally under pressure, or in organic solvents, such as alcohols, lower carboxylic acids, carboxylic acid alkyl esters, aromatics, chlorinated The treatment can be carried out in the presence of aromatic hydrocarbons, inert solvents such as dimethylformamide, dimethylsulfoxide, pyridine at temperatures from 80 to 180°C.

The above-mentioned organic solvents can be applied to the dry, untreated pigment in pure form or as a mixture with one another.

The azo pigment according to the invention has a melting range of 323 DEG to 328 DEG C. and is an orange powder, which is completely insoluble in common solvents.

The pigments are distinguished by their tinting strength, brilliant shade, good covering power and particularly good light and weather resistance.

In this case, the pigment is superior to most comparable azo pigments, which are prepared using the same coupling component, but which, as a diazo component, contain a compound that most closely resembles p-nitroaniline.

The pigment according to the invention thus contains 3-nitroaniline, 2
, 4-dinitroaniline, 4-chloroaniline, 4-methylaniline or 4-methoxyaniline as a diazo component in terms of light resistance and weather resistance.

Further, the pigment according to the present invention contains 2-chloroaniline, 2-methylaniline or 2-methoxyaniline as a diazo component in terms of light resistance and weather resistance, as described in German Patent No. 122758.
This is more worrying than the azo pigment described in Specification No. 5,
In terms of covering power and color gloss, it is superior to an ab pigment containing 2-nitroaniline as a diazo component.

The novel azo pigments according to the invention can be used in a very wide variety of pigment applications.

They can be used, for example, for the production of printing inks or for preparing lacquers and dispersion paints, or for coloring rubber, man-made substances, natural and synthetic resins.

The pigments are furthermore suitable for pigment printing onto substrates, in particular textile fibers, and also onto other planar shapes, such as paper.

The pigments may be used for other purposes, for example for dyeing viscose rayon, or cellulose-ethers or -esters, polyolefins, polyamides, polyurethanes, polyglycol terephthalates or polyacrylonitrile in the spinning solution; It can also be used to color paper.

Example 1 13.8 g (0.1 mol) of p-nitroaniline was added to 5N
Stir in 80 ml of hydrochloric acid.

This is cooled to 0-5 DEG C. using ice and then diazotized by flowing 20 rI'Ll of 5N sodium nitrite under the surface.

Then add diatomaceous earth, stir for 10 minutes and strain.

On the other hand, 5-acetoacetylaminobenzimidacylone (3
5%) 70.9 is dissolved in 200 ml of water and 25 ml of 33% caustic soda solution at 22°C and then clarified using bone char.

A mixture consisting of 500 rrLl of water, 25g of phosphoric acid, 30rl of 33% caustic soda solution and 10wLl of a 10% aqueous solution of stearyl alcohol oxyethylate (containing 20 units of ethylene oxide) is initially charged as a buffer.

The diazo solution and the coupling component solution are then simultaneously introduced into the buffer at 22°C.

Heat this to 95°C and continue stirring at this temperature for 1 hour.
Then, it is suction filtered and washed.

150 g of moist pressed cake is stirred with 140 g of inbutanol and 200 ml of water and 1/2 to
Hold at 125°C for 1 hour.

Removing the inbutanol with water vapor and wiping off the residue produces an orange-red pigment with poor light and weather resistance, high covering power, and baking properties, good flowability and high gloss in lacquers. is obtained.

Example 2 27.6 g (0.2 mol) of p-nitroaniline are diazotized as described in Example 1.

The diazo solution and the azo component are simultaneously introduced into a Na-acetate/glacial acetic acid buffer with the following composition.

This composition is 10,100 O of water, 8 O of sodium acetate.
2.9, 10 of stearyl alcohol oxyethylate containing 20 ml of glacial acetic acid and 20 units of ethylene oxide
Consisting of 10 ml of hydrophobic solution.

The mixture is heated to 95° C. and kept at this temperature for 1 hour, then filtered with suction and washed with water.

A wet press cake containing approximately 25 parts of pigment is worked up using imbutanol as described in Example 1.

This mixture was subjected to steam distillation and the dried backside 1
An orange-red pigment is obtained having the properties described in .

Example 3 13.8 g of p-nitroaniline are diazotized and coupled with a solution consisting of 24 g of 5-acetoacetylaminobenzimidacylon and 24 ml of 33% caustic soda solution in 200 TL of water.

In this case, both solutions are prepared at about 20° C. starting from 500 ml of water, 40 g of sodium acetate, 10 TL of glacial acetic acid, and stearyl alcohol, and mixed with 2 ml of ethylene oxide.
10 of the emulsifier obtained by reacting with 0 mol
% aqueous solution in a buffer consisting of 10 TfLl.

Stirring is continued for 1 hour, heated to 95°C, held at this temperature for 1 hour, and then filtered with suction.

125 g of moist pressed cake are heated under pressure to 125 DEG C. for 1/2 to 1 hour while adding 200 wLl of water, filtered with suction and washed with water.

After drying, an orange-red pigment with very good fastness properties is obtained.

Example 4 Pressed cake obtained as described in Example 3 (approximately 20 cakes)
125. ! i1' is stirred with 96 g of O-dichloropenzole and 100 ml of water and heated at 125 DEG C. in a closed container for 1 hour.

The 0-C/70 rubenzole is then removed from the pigment emulsion by blowing in steam.

After subsequent filtration, washing and drying, an orange-red pigment having properties similar to those described under 1 is obtained.

[Brief explanation of the drawing]

The drawing shows the infrared spectrum of the pigment obtained according to the invention.

Claims (1)

[Scope of Claims] 1. A method for producing a monoal pigment represented by the following formula, which comprises coupling diazotized P-nitroaniline with 5-acetoacetylaminobenzimidacylon. 2. Coupling diazotized p-nitroaniline with 5-acetoacetylaminobenzimidacylone,
A monoazo pigment of the formula according to claim 1, characterized in that the coupling product is then subjected to a thermal after-treatment at 80 to 180°C in the presence of water and/or an organic solvent. manufacturing method.