CS237378B1 - New disazopigments and method of their preparation - Google Patents

Abstract

New disazo pigments of yellow and red shades of general formula (51) Int. CL* C 09 B 35/26 where Rj., R? are the same or different residues of the azo component, not containing substituents causing water permeability and are coupled in the o-position to the phenolic or enolic hydroxy group, in particular residues of azo components of the type of acetoacetarylides, phenylmethylpyrazolones, 2-naphthol or arylides of 2-hydroxy-3-naphthoic acid.

Description

The invention relates to novel disazopigments of yellow to red shades which are insoluble or slightly soluble in conventional solvents. So far known and described are color disazopigraents starting from 4,4-diaminodiphenyl urea.

They are useful for dyeing paper and viscose fibers in mass, for printing textiles and paper, for pigmenting synthetic resins, lacquers and inks. At higher concentrations, they have satisfactory to good light fastness, good to very good fastness to washing, dry cleaning, migration, peroxide bleaching.

Color pigments of similar properties having the general formula have now been found

wherein R 6, R 8 are the same or different azo component having no water-solubility substituents and are coupled to the o-position to the phenolic or enolic hydroxyl group, especially acetoacetarylide, phenylmethylpyrazolone, 2-naphthol or 2-hydroxy-3-naphthoic acid arylide

The novel disazopigments can be prepared by tetrazolalating 3,3-diaminodiphenylurea in a mineral acid medium in the cold by slowly adding sodium nitrite solution. The tetra-compound may be coupled with azo components in acetic acid, neutral or soda alkali at temperatures of 0 to 50 ° C, optionally in the presence of solvents. Ready

- 2 237 378 pigments may be subjected to further mechanical processing, such as fine milling in pearl mills and amionic or non-ionic dispersants, to commercial forms of pigment dough,

In order to further elucidate the nature of the invention, the following examples are provided:

Example 1

12.1 g of 3,3-diaminodiphenylurea are dissolved in 200 ml of water with 50 ml of a 5 mol / l standard hydrochloric acid solution, cooled below 5 ° C and added dropwise with 40 ml of a 2.5 mol / l sodium nitrite solution.

After stirring for half an hour, 1 g of carborafine was added and the diazo solution was filtered. Capacity approx. 400 ml, clear, yellow-brown color.

Meanwhile, 18 g of acetoacetanilide is dissolved in 650 ml of water with about 11 ml of a 10 mol / l sodium hydroxide solution at 40 ° C. After the addition of 0.5 g of Solegal W (condensation product of ethylene oxide with aliphatic alcohols or alkylphenols), acetoacetanilide was precipitated with ca 6 ml of acetic acid, concentrated, pH adjusted to 5.5, and maintained at that value by sodium hydroxide solution, and diazo solution in 45 minutes at 45 to 45 ° C · After the components have reacted, the pH is adjusted to 7.0, the reaction mixture heated to 95 ° C, and stirred at this temperature for 1 hour · After cooling to 80 ° C filtration and paste washed with warm water Yield 204 g of paste, after drying 33 S. solids 274 to 277 ° C, after recrystallization from dimethylformamide 300 to 302 ° C. The greenish-yellow powder is insoluble in water, hexane, trichlorethylene, very poorly soluble in ethanol and ethyl acetate, partially soluble in dimethylformamide and dimethyl sulfoxide.

g of the dried pigment is ground in a pearl mill in 90 ml of water with 10 g of Solegal W and 1 g of silicone antifoam to a particle size of 0.1 to 1 µm · The dispersion of this dough in water shows a CIE coordinate at 0.210 in transmitted light

- 3 237 378 in «0.158. When used in textile printing with a suitable binder based on butadiene acrylate polymers, it gives a greenish-yellow color with excellent wash and dry fastnesses and average light fastnesses,

If the coupling is carried out at pHip H instead of 5.5, a more intensely colored product is formed with a melting point above 350 ° C.

Example 2

The diazotization and coupling performed as in Example 1, instead of acetoacetanilide used as azokomponenty 21 g acetoacet-o _f -anisididu. The yield was 37 g of a green-yellow powder, mp 64 DEG-268 DEG C., completely insoluble in hexane and trichlorethylene, slightly soluble in hot ethanol and ethyl acetate.

After grinding with water and Solegal W used to print textiles a light greenish shade with excellent fastnesses in washing and chemical cleaning and good light fastness. CIE coordinates of the transmitted light dispersion at 0,1 0.190, v = 0.105. After grinding with water and Tamol, NGO (the naphthalenesulfo acid-formaldehyde condensation product) used to color the viscose rayon in the mass to a yellow shade with excellent fastnesses in washing, dry cleaning, bleaching and light.

Example 3

Diazotization was carried out as in Example 1 (14 g of bis-acetoacet-p-phenylenedismin was used as an azo component instead of acetoacetanilide, coupled at pH 8-9 in sodium bicarbonate in the presence of an anionic dispersant (Turkish red oil) to yield 29 g of yellow powder. , completely insoluble in hexane, trichlorethylene, dibutyl phthalate and ethanol, slightly soluble in acetone, gives a yellow, non-migratory color with average light fastness in plasticized polyvinyl chloride.

Example 4

The diazotization was carried out as in Example 1. A mixture of 9 g of phenylmethylpyrazolone and 7.5 g of 2-naphthyl was added for coupling, which was dissolved together in water by addition of sodium hydroxide and precipitated by addition of sodium bicarbonate to pH 8-9.

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After coupling, the reaction mixture was filtered, the paste was washed with warm water until the filtrates were free of chloride ions, the pearl mill ground pasted by adding a non-ionic dispersant to a particle size below 1 µm and used for textile printing on orange shade with good wash fastness, dry cleaning and in the light.

Further disazopigmentys were prepared by the methods described in Examples 1-4

Azokomponenta

2-2-Hydroxy-3-naphthoic acid methoxyphenylamide 2-Naphthol

2,5-dimethoxyphenylamide 2-oxy-3-naphthoic acid acetoacet-o-chloroanilide 1- (p-tolyl) -3-methyl-5-pyrazolone 1- (2-chlorophenyl) -3-methyl-5-pyrazolone textile print red yellowish red bluish red greenish yellow reddish yellow reddish yellow

Claims (1)

OBJECT OF THE INVENTION 1. New disazopigments of general formula 237 378 ρ-ν = ν (\ / V = A / dkie RU R _o are the same or different azocaponent residues not containing water-solubility substitutes and are coupled also by o-positions to the phenolic or enolic hydroxyl group, , phenyl-ethyl-pyrazolones, 2-naphthol or 2-hydroxy-3-naphthoic acid aryls. A process for preparing novel disazopigments according to item 1, characterized in that one mole of tetrazotized 3,3-ia-acaiphenylurea is coupled with two aols of azo-apoaponent-free substituents, causing water-solubility and capable of coupling to the o-position to phenolicx or enol hydroxyl, or two moles of such mixtures. components, or with one mole of diffusive azo-components.