SU654655A1 - Monoazo compounds of phenanthridone series for colouring plastics polygraphic and paint and varhish materials - Google Patents

Description

The proposed monoazo dyes are distinguished from those known in that as Ar, instead of phenyl, use residues of 2-amino-4, 4-amino- or 8-aminophenanthridone.

The method of obtaining the proposed insoluble monoazo dyes is that the amine of the general formula

tn.

- // g

where RI, R2 and Ra have the indicated meanings, diazotize and the resulting diazo compound is combined with acetoacetic (I) or 2,3-hydroxynaphthoic acid arylide of the general formula

COCHj

.N-h

Azo coupling is carried out in the presence of non-ionic surfactants and solvents miscible with water. In the form of a paste or dry powder, the pigments may be treated with solvents. The obtained pigments paint plastics, printing and paintwork materials in red, durable to light, heat, migration and solvents.

Example 1. 1.68 g (0.01 gmol) of 3-nitro-4-aminoanisole is stirred for 1 hour at 20 ° C with 3 ml of hydrochloric acid, 20 ml of water and 0.1 g of syntamide-5 and diazotized at About -5 ° C, tide 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 8-phenanthridide acetoacetic acid is dissolved by heating in 2 ml of a 20% sodium hydroxide solution, 50 ml of water and 50 ml of propyl alcohol.

A solution of 8-phenanthridide acetoacetic acid and then 10 ml of 20% sodium acetate solution (to pH 5) are quickly added to the filtered solution of the diazo compound. The reaction mixture is stirred for 1 h at 20 ° C and 1 h at 93-95 ° C. The precipitate is filtered off, washed with water and treated with 40 ml of dimethylformamide at boiling for 1 h.

4.32 g of pigment are obtained, which paints the polyvinyl chloride film in a strong orange-yellow color.

Example 2. 1.68 g (0.01 gmol) of 5-nitro-2-aminoanisole is stirred for 1 hour at 20 ° C with 3 ml of hydrochloric acid and 20 ml of water. Then it is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 8-phenanthridide acetoacetic acid are dissolved by heating in 2 ml of a 20% sodium hydroxide solution, 50 ml of water and 50 ml of propyl alcohol; 0.1 g of the OC-20 preparation is added to the solution and then filtered.

To a solution of 8-phenanthridide acetoacetic acid at 20 ° C is added a filtered solution of the diazo compound at such a rate that there is no large excess of diazo compound in the reaction mixture.

After adding the diazo components, the reaction mixture is stirred for 1 hour at 20 ° C.

and 1 hour at 93-95 ° C. The precipitate is filtered off, washed with water and dried at 50-60 ° C.

The dry powder is treated with 40 ml of dimethylformamide at boiling for

1 hour

Obtain 4.2 g of the pigment, dyeing polyvinyl chloride film in yellow color.

Example 3. 1.73 g (0.01 g-mol) of 4-chloro-2-nitroaniline is stirred for 1 hour at 20 ° C with 3 ml of hydrochloric acid and 20 ml of water. Then it is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 2-aminophenanthridide acetoacetic acid is dissolved by heating in 2 ml of a 20% sodium hydroxide solution, 50 ml of water and 50 ml of ethanol. 0.1 g of the preparation is added to the solution.

DS-10 and filtered.

To a solution of 8-phenanthridide acetoacetic acid at 20 ° C is added a filtered solution of diazotized 4-chloro-2-nitroaniline at such a rate that

the reaction mixture did not have a large excess of the diazo compound. After adding the diazo components, the reaction mixture is stirred for 1 hour at 20 ° C and 1 hour at 93-95 ° C. The precipitate is filtered off, washed with water and treated with 40 ml of boiling dimethylacetamide for 1 hour. 4.5 g of pigment are obtained, which paints the polyvinyl chloride film in a solid yellow color.

Example 4. 1.68 g (0.01 gmol) of 5-nitro-2-aminoanisole is stirred for 1 hour at 20 ° C with 3 ml of hydrochloric acid and 20 ml of water. Then it is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 8-phenanthridide acetoacetic acid is dissolved by heating in 2 ml of a 20% sodium hydroxide solution, 50 ml of water and 50 ml of isopropyl

alcohol. 0.1 g of OP-10 was added to the solution and filtered.

To a solution of 8-phenanthridide acetoacetic acid at 20 ° C is added a filtered solution of a diazo component with

at a rate such that there is not a large excess of diazo compound in the reaction mixture.

After adding the diazo components, the reaction mixture is stirred for 1 hour at 20 ° C and 1 hour at 93-95 ° C. The precipitate is filtered off, washed with water and treated with 30 ml of ethylene glycol at the boil for 1 h.

4.25 g of pigment are obtained, which paints the polyvinyl chloride film in yellow.

Example 5. 1.68 g (0.01 gmol) of 3-nitro-4-aminoanisole is stirred for 1 hour at 20 ° C with 3 ml of hydrochloric acid and 20 ml of water. Then it is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 8-phenanthridide acetoacetic acid and 0.1 g of syntamide-5 are dissolved when heated in 2 ml of a 20% sodium hydroxide solution, 50 ml of water and 50 ml of propyl alcohol and the solution is filtered.

To a solution of 8-phenanthridide aueTOVKCVcn acid at 20 ° C is added a filtered solution of the diazo compound as it disappears from the reaction mixture. After the addition of the diazo components, the reaction mixture is stirred for 1 hour at 20 ° C and at 1 hour at 93-95 ° C. The precipitate is filtered off, washed with water and dried at 50-60 ° C.

DRY powder is treated with 40 ml of aniline at boiling for 1 hour.

4.3 pigments are obtained, which dye the polyvinyl chloride film in a strong yellow-orange color.

Example 6. 1.22 g (0.01 gmol) of 2-nitroaniline are placed for 30 minutes at 20 ° C with 3 ml of hydrochloric acid and 20 ml of water. The solution is cooled to 0 ° C, diazotized, a tide of 2.4 ml of 30% sodium nitrite solution and filtered.

3 g (0,0102 g-mol) of 4-phenanthridide acetoacetic acid and 0.1 g of synanol-10 are dissolved by heating in 2 ml of a 20% sodium hydroxide solution, 50 ml of water and 50 ml of ethanol.

To a solution of 4-phenanthridide acetoacetic acid at 20 ° C is added a filtered solution of diazotized 2-nitroaniline as the diazo component disappears from the reaction mixture. After the addition of the diazo compound, the reaction mixture is stirred at 93–95 ° C for 1 hour. The precipitate is filtered off, washed with water and treated with 40 ml of dimethylformamide at boiling for 1 h.

 4.25 g of pigment are obtained, dyeing the PVC film in a strong yellow-green color.

Example 7. 12.2 g (0.01 g-mol) of 2-nitroaniline are stirred for 30 minutes at 20 ° C with 3 ml of hydrochloric acid and 20 ml of water. Then it is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 4-phenanthridide acetoacetic acid and 0.1 g of the preparation OP-20 are dissolved when heated in 2 ml of a 20% aqueous solution of sodium hydroxide and 100 ml of water.

To a solution of 4-phenanthridide acetoacetic acid at 20 ° C, a filtered solution of diazotized 2-nitroaniline is added as the diazo-co-component disappears from the reaction mixture. After the diazo-component was added, the reaction mixture was stirred at 20 ° C for 1 hour and at 93-95 ° C for 1 hour. The precipitate is filtered off, washed with water and treated with 30 ml of quinoline at the boil for 1 h.

Obtain 4.2 g of pigment, dyeing polyvinyl chloride film in a solid yellow-green color.

Example 8. 1.86 g (0.01 g-mol) 2.-aminotoluene-4-sulfamide stirred

30 min at 20 ° С with 3 ml of hydrochloric acid and 20 ml of water. Then it is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 2-phenanthridide acetoacetic acid is dissolved by heating in 2 ml of a 20% -Froro sodium hydroxide solution, 50 ml of water and 50 ml of isopropyl

alcohol. Then 0.1 g sintamide-5 is added. To the filtered solution of 2-phenanthridide at 20 ° C, add the diazo compound solution at such a rate that there is no large excess of the diazo compound in the reaction mixture. After adding the diazo components, the reaction mixture is stirred for 1 hour at 20 ° C and 1 hour at 93-95 ° C. The precipitate is filtered off, washed with water and treated with 40 ml of dimethylacetamide at boiling for 1 h.

Obtain 4.5 g of the pigment, dyeing polyvinyl chloride film in a solid yellow color.

Example 9. 2.14 g (0.01 gmol) of 4-aminobenzanilide are placed for 30 min with 3 ml of hydrochloric acid and 20 ml of water at 20 ° C. Then it is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 8-phenanthridide acetoacetic acid and 0.1 g of the preparation OC-20 are dissolved when heated in 2 ml of a 20% aqueous solution of sodium hydroxide, 50 ml of water and 50 ml of nopropyl alcohol.

To a solution of 8-phenanthridide acetoacetic acid at 20 ° C is added a filter. solution of diazotized 4-amiobenzanilide as it disappears into

the reaction mixture. After the diazo-component was added, the reaction mixture was stirred for 1 hour at 20 ° C and for 1 hour at 93-95 ° C. The precipitate is filtered off, washed with water and treated with 40 ml of triethanolamine at boiling for 1 h.

4.6 g of pigment are obtained, which paints the polyvinyl chloride film in yellow.

Example 10. 2.14 g (0.01 gmol) of 4-aminobenzanilide is stirred for 30 minutes with 3 ml of complete acid and 20 ml of water at 20 ° C. Then the solution is cooled to 0 ° C and diazotized with a tide of 2.4 ml of 30% sodium nitrite solution.

3 g (0,0102 g-mol) of 8-phenanthridide acetoacetic acid and 0.1 g of preparate OC-20 are dissolved by heating in 2 ml of a 20% solution of sodium hydroxide, 50 ml of water and 50 ml of isopropyl alcohol.

10 ml of 20% sodium acetate solution (to pH 5) are added to the filtered solution of the diazo compound at -5 ° C and a solution of 8-phenanthridide acetoacetic acid is quickly added. The reaction mixture is stirred for 1 h at 20 ° C and 1 h at 93-95 ° C. The precipitate is filtered off, washed with water and dried at 50-60 ° C. Dry powder is treated with 40 dimethylacetamide at boiling for 1 hour.

4.3 g of pigment are obtained, which paints the floor of the vinyl chloride film in a reddish yellow color.

Example 11. 2.42 g (0.01 g-mol) of Z-amino-4-methoxy-isanilide are stirred for 1 hour at 20 ° C with 3 ml of hydrochloric acid (C36.5%) and 20 ml of water and diazotized gp O-5 ° C, tide 2.3 ml of 30% sodium nitrite solution.

3.86 g (0,0102 g-mol) of 8-fecantedide 2,3-hydroxy naphthoic acid is dissolved by heating in 3 ml of 20% sodium hydroxide solution, 50 ml of water and 50 ml of propyl alcohol; 0.1 g of smithpmid-5 is added to the solution and filtered.

To the filtered solution of the diazo compound, 10 ml of a 20% sodium acetate solution (to pH 5) are added and a solution of 8-phenanthridide of 2,3-hydroxy naphthoic acid is rapidly added by FPI. The reaction mixture is stirred for 1 hour at 20 ° C, 1 hour at 93-95 ° C. Then the precipitate is filtered off, washed with water and treated with 40 ml of dimethylformamide at boiling for 1 h.

5.3 g of a pigment are obtained, which paints a polyvini chloride film in a bluish red color.

Example 12. 1.52 g (0.01 g-mol) of 3-nitro-4-aminotolurl is stirred for 1 hour at 20 ° C with 3 ml of 35.6% hydrochloric acid and 2.0 ml of water. Then they are diazotized at O-5C, with a tide of 2.3 ml of 30% sodium nitrite solution.

3.86. g (0,0102 g-mol) of 8-phenanthridide 2,3-hydroxy naphthoic acid and 0.1 g of preparation DS-10 are dissolved in a mixture of 35 ml of water,. 35 ml of isopropyl alcohol and 3 ml of a 20% solution of caustic soda.

To the solution of 8-phenanthridide 2,3-hydroxy naphthoic acid is added a filtered solution of the diazo compound as it disappears in the reaction mass. After adding the entire solution, the reaction mixture is stirred for 1 hour in a nrn 20 ° C, 1 hour at 93-95 ° C. Then the precipitate is filtered off and work out 40 ml of triethanolamine at 100-110 ° C.

Obtain 5.1 g of pigment, dyeing polyvinyl chloride film in a durable

Red color.

Example 13. 1.7 g (0.01 gmol) of 3-nitro-4-aminoanisole are stirred for 1 hour at 20 ° C with 3 ml of 35.6% hydrochloric acid and 20 ml of water. Then diazotiruet at O-5 ° C

tide 2.3 ml of 30% sodium nitrite solution.

3.86 g (0,0102 g-mol) of 8-phenanthridide 2,3-hydroxy naphthoic acid is dissolved in 35 ml of water, 35 ml of ethyl

alcohol and 3 ml of a 20% aqueous solution of caustic soda. To the solution is added 0.1 g of synanol-10, stirred until dissolved, and filtered. The filtered solution of the diazo compound is added to the solution of 8-phenanthridide 2,3-hydroxy naphthoic acid at such a rate that there is no large excess of diazo compound in the reaction mass. After adding the entire solution, the reaction

the mixture is stirred for 1 h at 20 ° C, 1 h at 93-95 ° C. Then the precipitate is filtered off, washed with water and dried at 50-60 ° C.

Dry powder is treated with 40 ml of aniline at boiling for 1 hour.

5.33 g of pigment are obtained, which paints the polyvinyl chloride film in a solid red color.

Example 14. 1.62 g (0.01 g-mol) 2,5 dichloroaniline stirred for 1 h at 20 ° C

with 3 ml of 35.6% hydrochloric acid, 20 ml

water and diazotiruet at O-5 ° C, tide

2.3 ml of 30% sodium nitrite solution.

3.86 g (0,0102 g-mol) 8-phenanthridide

2.3-hydroxynaphthoic acid is dissolved in

3 ml of a 20% solution of sodium hydroxide, 35 ml of water and 35 ml of propyl alcohol. 0.1 g of the preparation OS- / 0 is added to the solution, stirred until complete dissolution and filtered.

The filtered solution of the diazo compound is added to the solution of 8-phenanthridide 2,3-hydroxy naphthoic acid at such a rate that there is no large excess of the diazo component in the reaction mass.

After adding the entire solution, the reaction mixture is stirred for 1 hour at 20 ° C, 1 hour at 93-95 ° C. Then the precipitate is filtered off, washed with water and 40 ml of ethylene glycol are worked at boiling for 1 hour.

5.12 g of a pigment are obtained which dyes a brown color to the polyvinyl chloride film. Said monoazo dyes possess

Claims (1)

high strength to organic solvents (5 points), good mitration resistance (4-5 points) and light resistance (5 points) in full tone, which makes it possible to create a new range of durable water-soluble azo dyes. The proposed monoazo dyes can be used in dyeing plastics, printing and paintwork materials. Claims of the invention Monoazo compounds of the phenanthridone series of the general formula 10 15 20 A - a group of the following structure eosTj -CH-dOMO COTift R-H, chlorine, methyl, methoxy, ntro, carbamoyl, carbmethoxy; R2 is H, chlorine, methyl, methoxy, nitro, carbamoyl, N-arylcarbamoyl, sulfamide group; Нз - Н, chlorine, methoxy, carbamoyl, N-arylcarbamoyl, sulfamide group, N-dialkylsulfonamide group for dyeing plastics, printing and paintwork materials.