CH545839A - Yellow heterocyclic pigments - for plastics,paints, paper etc - Google Patents

Abstract

Greenish/yellow and reddish/yellow slightly water-sol heterocyclic cpds. for colouring paints and varnishes based on plastic or resin materials for bulk dyeing viscose and cellulose acetete, pigmenting polyolefins, rubber, synthetic leather, printing inks, paper pulp and for coating or pigment printing textiles fast shades, esp. to migration have the formula: (wherein R1 is Cl and R is H or R1 is H and R is CH3). Prepared by reacting e.g. 2 mols of 5:6 - dichloro-3 imin-isoindolinone with 1 mol 2,2'-dichloro-4,4-diamino-biphenyl.

Description

  

  
 



  The invention relates to a process for the preparation of sparingly soluble compounds of the general formula
EMI1.1
 wherein Hal denotes a halogen atom and the nuclei A and B can carry further substituents, with the exception of carboxylic acid and sulfonic acid groups. These compounds are outstandingly suitable as pigments, in particular for coloring plastic compounds.



   It has been found that you can get very valuable pigments of the formula
EMI1.2
 obtained, in which the symbols R1 independently of one another fluorine, chlorine or bromine, R2 fluorine. Chlorine. Bromine, diethyl ethyl with optional substituents. Methoxy or ethoxy, R3 hydrogen or one of the meanings of R2 and R4 and Rs, independently of one another, one of the meanings of R3 or together a ring member of the formula -CO-, -SO2. -CH2, -NHCO-CH2-, -NH -, - S- or -O- mean when 2 moles of a compound or a mixture of compounds of the formula
EMI1.3
 wherein X is a group of the formula = NH or two halogen atoms. preferably chlorine or bromine atoms, with 1 mol of a compound of the formula
EMI2.1
 condensed.



   As substituents on the alkyl or alkoxy radicals (R2 and / or R3), for. B. chlorine, bromine, methoxy, ethoxy or cyan in.Beicht.



   The condensation of compounds of formula (II) in which X is an imino group takes place preferably in polar organic solvents, e.g. B. alcohols, ether alcohols, N-dialkyl acylamides or dimethyl sulfoxide, in the absence of acids that bind the ammonia released, instead. It can also be in an organic acid, e.g. B.



  Glacial acetic acid, which also acts as a solvent, can be worked.



   The condensation can also be carried out using a neutral salt of the diamine of the formula (III) with a strong mono- or polybasic acid (for example the chlorohydrate or the sulfate).



   If X in formula (II) is halogen, it is preferably used in an inert solvent or solvent mixture, e.g. B.



  Toluene, nitrobenzene or a chlorobenzene, in the presence of acid-binding agents, e.g. B. alkali acetate, carbonate, bicarbonate, magnesium oxide, or pyridine, etc. worked.



   In general, regardless of the meaning of X, the reaction is carried out at temperatures between 20 and 200 ° C., preferably between 70 and 120 ° C.



   The compounds prepared in this way are, especially after the conditioning customary for pigment dyes, e.g. B.



  for coloring plastic masses, which means solvent-free and solvent-containing masses made of plastics or synthetic resins (in paints on an oily or watery basis, in varnishes of various types, for spin dyeing viscose or cellulose acetate, for pigmenting polyethylene, polystyrene, polyvinyl chloride, rubber and synthetic leather) suitable. They can also be used in printing inks for the graphic industry, for pulp dyeing, for coating textiles or for pigment printing.



   The dyeings obtained are outstandingly fast to migration and light, have very good fastness to washing, chlorine bleach, hypochlorite, bleach, overdyeing, blind vat, peroxide bleaching, rubbing, overcoating and solvent fastness and are distinguished by good transparency and heat resistance out.



   In the following examples, the parts are parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius.



   Production of the starting material
235 parts of 4,5-dichlorophthalic acid, 180 parts of urea and 2.5 parts of ammonium molybdate are stirred in 1000 parts of ortho dichlorobenzene for 6 hours at 140 ° to 150 ° C., during which time carbon dioxide, ammonia and water are released. The reaction mass is then cooled to 1000, the precipitate formed is filtered off. washed first with methanol and finally with water. After drying, e.g. B. in a vacuum at 60 ° C., very pure 5,6-dichloro-3imino-isoindolinone is obtained. Starting from an equivalent amount of 4.5 dibromophthalic acid, this procedure gives 5,6-dibromo-3-iminoisoindolinone.



   example
47 parts of 5,6-dichloro-3-imino-isoindolinone and 28.5 parts of 3,3-dichloro-4,4-diaminodiphenyl chlorohydrate are heated in 400 parts of dimethylformamide to 1000 for 3 hours with thorough stirring. The resulting yellow precipitate is filtered hot, washed with dimethylformamide and then with water and dried. The product is dissolved in a mixture of 500 parts of ethyl alcohol and 25 parts of 33 percent sodium hydroxide solution at 600, stirred briefly after the addition of activated charcoal, filtered and reprecipitated from the filtrate by acidification with 15 parts of acetic acid. The pigment thus obtained is filtered off while hot, washed with ethyl alcohol and water and dried at 1000.

 

   The strongly colored, reddish-yellow pigment of the formula
EMI2.2
 is ideal for coloring plastics and lacquers and is characterized by its very good fastness to light, heat, migration and varnish.



  The dyes in the following table correspond to the formula
EMI3.1
 and are prepared analogously to the procedure of Example 1.



   table
R1 R2 R3 R4 R5 Nuance
2 Cl OCH3 OCH3 H H orange
3 Cl CH3 CH3 Cl Cl yellow 4 Cl H H Cl Cl green. yellow 5 Cl CH3 CH3 CH3 CH3 green. yellow 6 Cl OCH3 OCH3 Cl Cl yellow 7 Cl H H Br Br yellow 8 Cl H H -S02- yellow

 

Claims (1)

PATENT CLAIMS I. Process for the preparation of sparingly soluble heterocyclic compounds of the formula EMI3.2 wherein the symbols Rl independently of one another fluorine, chlorine or Bromine, R2 fluorine, chlorine, bromine, optionally methyl, ethyl, methoxy or ethoxy bearing substituents, R3 is hydrogen or one of the meanings of R2 and R4 and, independently of one another, one of the meanings Rs gen of R3 or together a bridge member of the formula -CO-, -SO2-, -CR2-, -NHCO-, -NR-, -S- or -O- mean, characterized in that 2 mol of a compound or of a mixture of compounds of the formula EMI4.1 wherein X is a group of the formula = NH or two halogen atoms, with 1 mol of a compound of the formula EMI4.2 condensed. II. Use of a compound of the formula (I) prepared according to patent claim I for coloring plastic compositions. III. Compound of formula (I), produced by the process according to claim I.