DE2532540A1 - NEW DISAZOPIGMENTS AND METHODS FOR THEIR PRODUCTION - Google Patents

Description

New disazo pigments and processes for their production

The present invention relates to valuable new disazo pigments the formula

Kr

(D

wherein R, a Η atom, an alkyl group optionally substituted by a phenyl group containing 1-4 C atoms, an aryl group, in particular a phenyl group optionally substituted by halogen atoms, alkyl or alkoxy groups containing 1-4 C atoms, R ₂ Η atom, an alkyl group containing 1-4 C atoms, a cyano or carbamoyl group, or an alkanoylamino group containing 2-4 C atoms, R ^ an alkyl group containing 1-4 C atoms, an alkoxycarbonyl group containing 2-6 C atoms or a halogen atom, alkyl or alkoxy group,

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containing 1-4 C atoms, substituted phenyl group, Z an O atom or an N atom, which together with the radical R,
forms a benzimidazole ring, X and Y represent H or halogen atoms, methyl or nitro groups and V represent an O atom or a -CO group.

The pigments of the formula are of particular interest
R.

(ID

or

(III)

wherein R ₁ , R 3 and Z have the meaning given above.

The new disazo pigments are obtained by using the tetrazo compound of a diamine of the formula

(IV)

with a pyridine derivative of the formula

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(ν)

couples in a molar ratio of 1: 2.

Of particular interest as diamines are 1,5- and 2,6-diaminoanthraquinone.

Other diamines are:

4,8-Dinitro-1,5-diaminoanthraquinone 2,6-dimethyl-1,5-diaminoanthraquinone 2,6-dibromo-1,5-diaminoanthraquinone 1,6-diaminoanthraquinone 1,7-diaminoanthraquinone 1,5-dichloro-2,6-diaminoanthraquinone 3,7-dibromo-2,6-diaminoanthraquinone 1,3,5,7-tetrabromo-2,6-diaminoanthraquinone 1,5-dinitro-2,6-diaminoanthraquinone 2,4,6,8-tetrachloro-1,5-diaminoanthraquinone 2,4,6,8-tetrabromo-1,5-diaminoanthraquinone 1,5-dibromo-2,6-diaminoanthraquinone 3,7-dibromo-2,6-diaminoanthraquinone

3,6-dibromo-2,7-diaminoanthraquinone and finally

2,6-diaminoxanthone

3-methyl-2,6-diaminoxanthone

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The coupling components preferably correspond

the formula

(VI)

where R ,, R ~ and Z have the meaning given.

Of particular interest are pyridine derivatives

Formulas

(VII)

(VIII)

wherein R, and R ^ have the meaning given, preferably mean a methyl or phenyl group, X, and Y-, H- or Halogen atoms, nitro or carbamoyl groups, alkyl, alkoxy or alkylsulfonyl groups containing 1-4 C atoms, alkoxycarbonyl, Containing alkanoylamino or alkylcarbamoyl groups 2-6 C atoms or optionally substituted by halogen atoms, alkyl or alkoxy groups containing 1-4 C atoms Phenoxy or phenylcarbamoyl groups.

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The pyridones of the formula (JlI) are known compounds.

Examples include: 4-methyl-3-cyano.-6-hydroxypyrid-.2-one 1-methyl-3-cyano-4-methy1-6-hydroxypyrid-2-one 1-Ethyl-3-cyano-4-methyl-6-hydroxypyrid-2-one 1-phenyl-3-cyano-4-methyl-6-hydroxypyrid-2-one 1-p-Tolyl-3-cyano-4-methyl-6-hydroxypyrid-2-one 1-p-anisyl-3-cyano-4-methyl-6-hydroxypyrid-2-one 1-phenyl-3-cyano-4-phenyl-6-hydroxypyrid-2-one 1-p-toly1-3-cyano-4-phenyl-6-hydroxypyrid-2-one 1-p-anisyl-3-cyano-4-phenyl-6-hydroxypyrid-2-one 1-phenyl-3-carbonamido-4-methyl-6-hydroxypyrid-2-one 1-phenyl-3-carbonarr.ido-4-phenyl-6-hydroxypyrid-2-one 2,6-dihydroxy-3-cyano-4-ethoxycarbonylpyridine 2,6-dihydroxy-4-methylpyridine 2,6-dihydroxy-4-phenylpyridine, 2,6-dihydroxy-4- (p-methoxyphenyl) pyridine 4-methyl-2,6-dihydroxypyridine l_Aethyl-4-methyl-3-acetylamino-6-hydroxypyrid-2-one 1,4-DimethyL-3-acetylamino-6-hydroxypyrid-2-one l-ethyl ^ -phenyl-S-acetylamino-ö-hydroxypyrid - ^ - one 1-phenyl-4-methyl-3-acetylamino-6-hydroxyρyrid-2-one

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The benzimidazolopyridines are conveniently obtained by known processes by condensing a benzimidazole the formula

wherein R ^, X- ^ and Y have the meaning given, with a Acyl acetic ester of the formula

R ₃ COCH ₂ COOR

where R is an alkyl group containing 1-4 C atoms and Ro has the meaning given.

As examples of acyl acetic esters. are mentioned:

Methyl acetoacetate Ethyl acetoacetate Benzoylacetic acid ethyl ester Diethyl oxaloacetate.

As benzimidazoles are mentioned:

2-cyanomethyl-benzimidazole 2-cyanomethyl-4-chloro-benzimidazo1 2-cyanomethyl-5-chlorobenzimidazole 2-cyanomethyl-5,6-dichlorobenzimidazole 2-cyanomethyl -4-chloro-6-methy1-benzimidazo1 2-cyanomethyl-5-methoxy-benzimidazole 2-cyanomethyl-6-ethoxy-benzimidazole 2-cyanomethyl-6-nitro-benzimidazole 2-Cyanmethy1-5-methy / sulfonyl-benzimidazole Benzimidazolyl-2-acetic acid amide

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2-ethyl-benzimidazole
2-cyanomethyl-6-trifluoromethyl-benzimidazole

The coupling takes place expediently by gradual Addition of the tetrazonium solution to an aqueous or organic solution of the coupling component at a pH of 4-8 instead. The pH is advantageously adjusted by adding a buffer. The salts, for example, are used as buffers, in particular Alkali salts of formic acid, acetic acid or phosphoric acid as well as tertiary nitrogen bases such as pyridine, Trimethyl, triethyl or triethanolamine in question. In addition, the coupling solution can be wetting, dispersing or Emulsifiers, for example an aralkyl sulfonate such as dodecylbenzenesulfonate, Polycondensation products of ethylene oxides, such as the action product of ethylene oxide on p-tert. Octylphenol, also alkyl esters of sulforicinoleates, for example n-Butyl sulforicinoleate can be added. The coupling dispersion can also contain protective colloids, for example methyl cellulose or contain small amounts of an inert organic solvent that is sparingly soluble or insoluble in water, for example halogenated or nitrated aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene or nitrobenzene, as well as aliphatic halogenated hydrocarbons, such as carbon tetrachloride or trichlorethylene, also water-miscible organic solvents such as acetone, methanol, ethanol, isopropanol, methyl ethyl ketone as well as dimethylformamide.

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Thanks to their insolubility, the pigments obtained can be isolated from the reaction mixtures by filtering them off. In order to obtain excellent texture of these pigments, a post-treatment boiling organic solvent to be advantageous turns out usually in a, preferably about 10O ⁰ C. Benzene derivatives substituted by halogen atoms, alkyl or nitro groups, such as xylene, chlorobenzene, o-dichlorobenzene or nitrobenzene, and pyridine bases such as pyridine, picoline or quinoline, and ketones such as cyclohexanone, ethers such as ethylene glycol monomethyl ether, amide glycol monoethyl ether such as ethylene glycol monoethyl ether, prove to be particularly suitable Di-

Dimethylacetemide
methylformamide, / or N-methylpyrrolidone and sulfoxane. The post treatment is preferably accomplished by heating the dried pigment in the solvent at 100-150 ⁰ C to obtain a uniform crystal structure and is formed in many cases a grain coarsening, which has a favorable effect on the rheological behavior, and to the migration and light fastness of the pigments obtained.

The coupling can also be carried out advantageously in such a way that an acidic solution of the tetrazonium salt is used slowly to one with a tert. Base-buffered organic solution of the coupling component is added. As an organic solvent are particularly suitable solvents which are miscible with water, such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, as well as dimethyl sulfoxide or sulfoxone. This method has the advantage that after the coupling has ended, water is available and volatile solvents, which were added with the tetrazo component, distill off and the aftertreatment can perform in the coupling suspension.

_ 8th _
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The coupling can also be carried out in such a way that an acidic solution of the tetrazonium salt with an alkaline solution of the coupling component in a mixing nozzle continuously combined, with an immediate coupling of the components takes place. The dye suspension obtained is the Mischdlise continuously withdrawn and the dye by filtering severed.

Instead of the tetrazonium salts it is also possible to use the corresponding tetrazoamino compounds. This receives one according to a known method by coupling an aryl tetrazonium salt with 2 mol of a primary or preferably one secondary amine. A wide variety of amines are suitable for this purpose, for example aliphatic amines such as methylamine. Ethylamine, ethanolamine, propylamine, butylamine, hexylamine and especially dimethylamine, diethylamine, diethanolamine, Methylethanolamine, dipropylamine or dibutylamine, aminoacetic acid, Methylaminoacetic acid, butylaminoacetic acid, aminoethanesulfonic acid, methylaminoethanesulfonic acid, guanylethanesulfonic acid, ß-aminoethylsulphuric acid, alicyclic amines, such as cyclohexylamine, N-methylcyclohexylamine, dicyclohexylamine, aromatic Amines, such as 4-aminobenzoic acid, sulfanilic acid, 4-sulfo-2-aminobenzoic acid, (4-sulfophenyl) -guanidine, 4-N-methylamino-benzoic acid, 4-ethylaminobenzoic acid, l-aminonaphthalene-4-sulfonic acid, l-aminonaphthalene-2,4-disulfonic acid, heterocyclic amines such as piperidine, morpholine, pyrrolidine, dihydroindole and finally also sodium cyanamide or dicyandiamide.

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As a rule, the tetrazoamino compounds obtained are sparingly soluble in cold water and can optionally after salting out in crystallized form from the reaction medium be separated. In many cases, the press cake can be moist can be used for further implementation. In individual cases it can prove useful to use the tetrazoamides prior to the implementation to be dewatered by vacuum drying.

Me coupling of the tetrazoamino compound with the
The coupling component takes place in an organic solvent, for example chlorobenzene, o-dichlorobenzene, nitrobenzene, pyridine, ethylene glycol, ethylene glycol monoethyl or monomethyl ether, dimethylformamide, formic acid or acetic acid. at
Using solvents that are miscible with water, it is not necessary to water-free the tetrazoamino compounds
Shape to use. For example, the watery, moist filter cake can be used.

The coupling is conveniently carried out at elevated temperature, preferably at temperatures between 80-180 ⁰ C, in an acidic medium
carried out and is generally very quick and complete. If neutral solvents are used, it is advantageous to add an acid, for example hydrogen chloride, sulfuric acid, formic acid or acetic acid. Thanks to their insolubility, the pigments obtained can be removed from the reaction mixture
can be isolated by filtration. A follow-up treatment with
organic solvents, as is required for pigments that are obtained by the aqueous coupling route
therefore unnecessary in most cases.

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Finally, the coupling can also be carried out in such a way that the diamine to be tetrazotised is mixed with the coupling component suspended in an organic solvent in a molar ratio of 1: 2 and treated with a diazotizing agent, in particular an ester of nitrous acid, such as methyl, ethyl, butyl, amyl or octyl nitrite, with nitrosyl sulfur

acid or treated with nitrosyl chloride.

The new dyes are valuable pigments which, in finely divided form, are used for pigmenting high molecular weight organic material can be used, e.g. cellulose ethers and esters, such as ethyl cellulose, nitrocellulose, Cellulose acetate, cellulose butyrate, natural resins or synthetic resins, such as polymerization resins or condensation resins, e.g. aminoplasts, in particular urea and melamine-formaldehyde resins, Alkyd resins, phenoplasts, polycarbonates. Polyolefins such as polystyrene, polyvinyl chloride, polyethylene, Polypropylene, polyacrylonitrile, polyacrylic acid esters, polyamides, polyurethanes or polyesters, rubber, casein, silicone and silicone resins, individually or in mixtures.

It does not matter whether the mentioned high molecular compounds as plastic masses, melts or in the form of spinning solutions, lacquers, paints. Depending on the intended use, it proves to be advantageous to use the to use new pigments as toners or in the form of preparations.

Thanks to their high color strength and transparency, the new dyes are particularly suitable for use in Printing inks such as letterpress, gravure and offset printing '.

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_λι 25325Α0

In CH-PS 522 713 a pigment is described that by coupling tetrazotized 1,5-diaminoanthraquinone with 2 moles of 3-cyano-4-methyl-2,6-dihydroxypyridine is obtained. However, the color of this known pigment is blue indicated, while the pigment obtained according to the invention of tetrazotized 1,5-diaminoanthraquinone and 2 moles of 3-cyano-4-methyl-2,6-dihydroxypyridine, whose constitution is ensured by combustion analysis and mass spectrum, turns orange. Compared to the dyes described in DAS 1.544.372, the pigments according to the invention by a particularly high color strength and transparency in printing inks, furthermore by better light and migration fastness.

In the following examples, unless otherwise stated, parts are parts by weight and percentages Percentages by weight and temperatures are given in degrees Celsius.

example

11.9 parts of 1,5-diaminoanthraquinone are concentrated in parts by volume of glacial acetic acid and 30 parts by volume. Hydrochloric acid several Stirred for hours, then cooled to 0-5 ° and tetrazotized at this temperature with 25 parts by volume of 4N sodium nitrite solution. The tetrazo solution is adjusted to a volume of 600 parts with ice and water and clarified by filtration. 18.5 parts l-Aethyl ^ -hydroxy ^ -methyl-S-cyano-pyridon- (6) are in 1000 parts by volume of dimethylformamide and 100 parts by volume of pyridine dissolved and the tetrazo solution in 1 hour at 20-25 ° added dropwise with good stirring. After the addition of the tetrazo solution is complete the mixture is stirred for 1 hour at room temperature and then heated

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60 9886/107 2

to simmer. Water and acetic acid are distilled off until until the internal temperature reaches 150 °. At this temperature is stirred for a further 4 hours, during which the pigment is converted into a uniformly crystalline form. Then you let Cool to 100 °, filtered and washed with 100 ° warm dimethylformamide until the filtrate is practically colorless. Then it is washed with cold methanol and finally with water. After drying in vacuo at 70-75 °, one obtains a grain-soft pigment that colors plastics and paints in bright orange tones. The pigment corresponds to the formula

N = C

The following table lists other dyes that are obtained if you follow the instructions of the Example 1 the diaminoanthraquinones mentioned in column I. tetrazotized and coupled with the coupling component listed in column II. The column III gives the nuance of a 0.2% staining achieved with the dye in PVC.

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No. I. II III 2 1,5 diamino
anthraquinone 6-hydroxy-3-cyano-4-methyl-
pyridon-2 orange 3 Il l-methyl-S-cyano - ^ - methyl-ö-
hydroxy-pyridon-2 orange 4th Il l-propyl-3-cyano-4-methyl-6-
hydroxy-pyridon-2 orange 5 π l-isopropyl-S-cyano - ^ - methyl-o-
hydroxy-pyridon-2 orange 6th ff ln-butyl-3-cyano-4-methyl-6-
hydroxy-pyridon-2 orange 7th Il l-Benzyl-S-cyano - ^ - methyl-o-
hydroxy-pyridon-2 Brown 8th Il 6-hydroxy-4-methyl-pyridon-2 orange 9 Il 6-hydroxy-4-methyl-1-ethyl
pyridon-2 orange 10 If 6-hydroxy-4-methyl-in-butyl-
pyridon-2 orange 11 ti 6-hydroxy-4-methyl-3-carbon
amido-1-methyl-pyridon-2 orange 12th If 6-hydroxy-4-ynethyl-3-carbon
amido-1-ethyl-pyridon-2 orange 13th If 6-hydroxy-4-methyl-3-carbon
amido-pyridon-2 orange 14th π 6-hydroxy-4-mechyl-3-carbon
amido-1-propyl-pyridon-2 orange 15th If e-Hydroxy - ^ - methyl - ^ - carbon-
amido-1-isopropyl-pyridon-2 orange 16 If 6-hydroxy-4-methyl-3-carbon
amido-ln-butyl-pyridon-2 orange 17th 2,6 diamino
anthraquinone 6-hydroxy-3-cyano-4-methyl-
pyridon-2 yellow 18th If 6-hydroxy-3-cyano-4-methyl-1-
ethyl-pyridone-2 yellow
orange 19th ft o-Hydroxy-S-carbonamido ^ -
methyl-ethyl-pyridon-2 yellow 20th ff 6-hydroxy-3-carbonamido-4-
methyl-1-propyl-pyridon-2 yellow

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No. I. II III 21 2,6 diamino
anthraquinone 6-hydroxy ~ 3-carbonamido-4-
methyl-1-isopropyl-pyridone-2 yellow
orange 22nd Il 6-hydroxy-3-carbonamido-4-
methyl-1-n-butyl-pyridon-2 yellow 23 π 6-hydroxy-3-carbonamido-4-
methyl-1-methyl-pyridon-2 yellow 24 Il 6-hydroxy-3-cyano-4-methyl-1-
methyl-pyridone-2 yellow 25th It 6-hydroxy-3-cyano-4-methyl-i-
propyl-pyridon-2 yellow 26th Il 6-hydroxy-4-methyl-pyridon-2 yellow 27 Il 6-hydroxy-4-methyl-1-ethyl
pyridon-2 yellow 28 Il 6-hydroxy-4-methyl-1-n-butyl-
pyr idon-2 yellow 29 2,7 diamino
anthr ah inon 6-hydroxy-4-methyl-3-cyano-1-
ethyl-pyridone-2 yellow
orange 30th Il 3-cyano-4-carbethoxy-l, 2- (l ^f , 2 ') -
benz- (4 ', 5') - imidazolo-6-hydroxy-
pyridine Brown 31 2,6-diamino-7-
methyl-
anthr ah inon 6-hydroxy-3-cyano-4-methyl-1-
ethyl-pyridone-2 yellow 32 1,5 diamino
2,6-dimethyl-
anthr aquinone 3-Gyan-4-phenyl-l, 2- (l ^l , 2 ') - benz-
(4 ¹ , 5 ') - imidazolo-6-hydroxy-
pyridine bordeaux 33 2,6 diamino
3,7-dibromo-
anthraquinone 3-cyano-4-methyl-1.2- (l ^l , 2 ^f ) -benz-
(4 ¹ , 5 ') - imidazolo-6-hydroxy-
pyridine Red 34 Il 6-hydroxy-4-methyl-pyridon-2 yellow 35 2,6 diamino
1,5-dichloro
anthraquinone Il Brown 36 Il 3-cyano-4-methyl-l, 2- (l ', 2') - benz-
(4 ¹ , 5 ') - imidazolo-6-hydroxy-
pyridine Red 37 2,6 diamino
anthraquinone M. Red

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No. I. II CH ₃
^CN Yi CH ₃ III 38 1,5 diamino
anthraquinone 3-Cyano_4-methyl-l, 2- (l ^l , 2 ') -
benz- (4 ', 5') - imidazolo-6-
hydr oxypyr id in ^ λνΝ ^ ΟΗ
I. ΎΐοΗ Red 39 If 3-Cyano_4-phenyl-l, 2- (l ^f , 2 ') -
benz- (4 ¹ , 5 ') - imidazolo-6-
hydroxypyr i din CH ₃ CH ₃ Red 40 2,6 diamino
anthraquinone Il 6-hydroxy-4-methyl-3-acetyl-
aminopyridon-2 Brown 41 It 3-cyano-4-carbethoxy-l, 2- (l ', 2 ¹ ) -
benz- (4 ', 5') - imidazolo-6-hydroxy- 5-hydroxy-3-cyano-4-methyl-1-
ethyl-pyridone-2 beige 42 1,5 diamino
anthraquinone tt pyridine bordeaux 43 1,5 diamino
anthraquinone bordeaux 44 11 bordeaux 45 1,5 diamino
anthraquinone Red 46 2,6 diamino
xanthone yellow-
orange

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No. I. II III 47 1,5 diamino
anthraquinone 6-hydroxy-3-cyano-4-itiethyl-1-
phenyl-pyridon-2 range 48 ti 6-hydroxy-3-cyano-4-methyl-1-
(4 ¹ -chloro) -phenyl-pyridon-2 orange 49 Il 6-hydroxy-3-cyano-4-methyl-1-
(4 ¹ -methyl) -phenyl-pyridon-2 orange 50 M. 6-hydroxy-3-cyano-4-methyl-1-
(4 ¹ -methoxy) -phenyl-pyridon-2 orange

Example 51

65 parts stabilized polyvinyl chloride,

35 parts of dioctyl phthalate and 0.2 part of the dye obtained in Example 1 are stirred together and rolled back and forth on a two-roll calender for 7 minutes at 140 °. A pure orange-colored film of very good fastness to light and migration is obtained.

Example 52

1.00 g of the pigment prepared according to Example 1 is mixed with 4.00 g of bonding varnish of the composition

29.4% linseed oil stand oil (300 poise)

67.2 % linseed oil stand oil (20 poise)

2.1% cobaltoacetate (870 Co) and

1.3 7o lead acetate

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finely rubbed on an Engelsmann rubbing machine and then with the help of a cliché in the letterpress process

1 g / m printed on art paper. One obtains a strongly colored, pure and shiny orange tone of very good transparency.

The pigment is also suitable for other printing processes, such as gravure printing, offset printing, and flexographic printing Excellent results in these applications too.

Example 53

10 parts of titanium dioxide and 2 parts of the color body prepared according to Example 1 are mixed with 88 parts of a mixture of 26.4 parts of coconut alkyd resin, 24.0 parts of melamine-formaldehyde resin (50% solids content), 8.8 parts of ethylene glycol monomethyl ether and 28.8 parts of xylene ground in a ball mill for 48 hours.

If this lacquer is sprayed onto an aluminum foil, dried for 30 minutes at room temperature and then baked for 30 minutes at 120 °, a brilliant orange-colored lacquer with good gloss is obtained, which is characterized by very good lacquer, light and weather resistance.

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Claims (1)

Claims 1. Disazo pigments of the formula wherein R, a Η atom, one optionally by a phenyl radical substituted alkyl group containing 1-4 C atoms, an aryl radical, IU a Η atom, an alkyl group containing 1-4 C atoms, a cyano or carbamoyl group, or an alkanoylamino group containing 2-4 C atoms, R-, an alkyl group containing 1-4 C atoms, containing an alkoxycarbonyl group 2-6 carbon atoms or one optionally by halogen atoms, alkyl or alkoxy groups, containing 1-4 carbon atoms, substituted phenyl group, Z is an O atom or an N atom, the N atom together with the remainder R, forms a benzimidazole ring, X and Y H or halogen atoms, Methyl or nitro groups and V denotes an O atom or a —CO group. - 19 - 509886/1072 Disazo pigments of the formula R. Ri = 0 Hi ην - * = j R wherein R, R and Z have the meaning given in claim 1 to have. Disazo pigments of the formula wherein R ₁ , R ₃ and Z have the meaning given in claim 1. 4. Process for the preparation of disazo pigments of the formula i R, R. NO, - 20 ^ 509886/1072 253254U wherein R _{1 is} a Η atom, an alkyl group optionally substituted by a phenyl radical and containing 1-4 carbon atoms, an aryl radical, R _? a Η atom, an alkyl group containing 1-4 carbon atoms, a cyano or carbamoyl group or an alkanoylamino group containing 2-4 carbon atoms, R ~ an alkyl group containing 1-4 carbon atoms, an alkoxycarbonyl group containing 2-6 carbon atoms -Atoms or one optionally substituted by halogen atoms, alkyl or alkoxy groups containing 1-4 C atoms, substituted phenyl group, Z is an O atom or an N atom, the N atom together with the radical R-. forms a benzimidazole ring, X and Y denote H or halogen atoms, methyl or nitro groups and V denote an O atom or a -CO group, characterized in that the tetrazo compound of a diamine of the formula with a dihydropyridine derivative of the formula couples in a molar ratio of 1: 2. _ 21 - 509886/1072 5. The method according to claim 4, characterized in that that 1,5-diaminoanthraquinone is used as the diamine. 6. The method according to claim 4, characterized in that the diamine used is 2,6-diaminoanthraquinone. 7. The method according to claim 4, characterized in that the coupling component is a dihydropyridine derivative 1 Tf-I ' t the formula used, wherein R ,, R ~ and Z are given in claim 4 Have meaning. 8. A method for pigmenting high molecular weight organic material, characterized by the use the pigments according to claim 1. 9. High molecular weight organic material containing a pigment according to claim 1. - 22 _ 509886/1072