DE1768745A1 - Pigment dyes - Google Patents

Description

wherein Y is an optionally substituted hydrocarbon, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or Arylsulfonylreet represents, R represents the grouping -CO-B-CO-NH-E, wherein B is a single bond or an optionally further substituted or interrupted by heteroatoms saturated or unsaturated alkylene radical, an optionally further substituted one or polynuclear arylene radical or heteroarylene radical and E denotes an optionally interrupted by heteroatoms, optionally substituted saturated or unsaturated alkyl or cycloalkyl radical, an optionally further substituted heteroaryl radical or an optionally one or several halogen atoms such as chlorine, fluorine or bromine, nitro groups, alkyl groups with 1-12 C atoms, cycloalkyl groups,

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fused-on cyclohexyl or benzene rings, trifluoromethyl groups, aryamino groups, hydroxyl groups, alkoxy groups with 1-3 carbon atoms, phenoxy groups, alkylsulfonyl groups, arylsulfonyl groups, alkylcarbonyl groups, aryloarbonyl groups, carboxyl groups, carboxylic acid ester groups, unsubstituted carboxamido groups, carboxylic acid ester groups, unsubstituted arylamino sulfonylamino groups, phenylsulfonylsulfonylsulfonylamino groups, phenylsulfonylsulfonyl, phenylsulfonylsulfonyl, phenylsulfonylamino groups, phenylsulfonylsulfonylsulfonylamido groups, hydroxy groups, alkoxy groups with 1-3 carbon atoms, phenoxy groups or Phenylazoxygruppen having aryl radical, and wherein the C and D rings may optionally have further substituents,

as well as their production and use as pigments.

Preferred dyes are those of the formula

0 NH-CO-B'-CO-NH-E

It I

(II)

where £ and Y have the abovementioned meaning and B * stands for an optionally substituted arylene radical, preferably an optionally substituted phenylene radical.

The compounds according to the invention are prepared according to on well-known processes by acylation of anthraquinone derivatives the formula

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(III)

«T O IH-Y

in which T has the meaning given above and the rings C and D optionally have more pus substituents.

Bit reactive derivatives of dicarboxylic acids of the formula

HO-CO-B-CO-OH (IV)

in which B has the abovementioned meaning and in which at least 1 mol of the compound (IV) is produced per free amino groups .

and subsequent implementation of an amine formula

B (V)

in which S has the meaning given,

with at least 1 mol of the amine (V) being used for each ML group to be converted into the Beat IH-R.

The preparation of the compounds according to the invention can according to Methods known per se are also carried out by acylating γόη anthraquinone derivatives of the formula

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(VI)

η ι

O NH-Y

wherein Y has the meaning given above and the rings C and D can optionally have further substituents,

with reactive carboxylic acid derivatives of N-substituted dicarboxylic acid monoamides of the formula

HQOC-B-CO-NH-E (TU)

in which B and £ have the meaning given.

Under reactive derivatives are in particular the halides, for example the chlorides or bromides and the esters, especially the alkyl esters.

The preparation of the compounds erfindungegemäßen can be carried out, for example, by reacting an amine of formula (VI) with excess or equivalent amounts of a Dicarbonsäurehaloge- W nids of formula

A-CO-B-CO-A (VIII)

in which B has the meaning given above, and A Ha- » Log like fluorine, chlorine or bromine means at temperatures between 40 ° C and 220 ° C in an organic solvent

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such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene, trichlorobenzene, nitrobenzene, optionally in the presence of other catalysts such as pyridine, piperidine, morpholine, trimethylamine, collidine, picoline, lutidine, quinoline with or without the addition of acid-binding agents such as soda, potash, sodium or potassium carbonate or quick lime until the Auagangsamin is completely consumed

and the resulting compound of the formula

(IX)

in which Y has the meaning given above and W is the radical -CO-B-CO-A is, in which B and A have the meaning given above,

after separation from the reaction solution or without isolation with amines of the formula (V) at temperatures between 40 ⁰ C and 220 ⁰ O using the amine H ₂ NE ala solvent or in an organic solvent such as benzene-toluene, xylene, chlorobenzene, dichlorobenzene, Trichlorobenzene, nitrobenzene, if appropriate in the presence of basic catalysts such as pyridine, piperidine, morpholine, triethylamine, collidine, picoline, lutidine, quinoline with or without the addition of acid-binding agents such as soda, potash, sodium or potassium bicarbonate or banned lime. As an example of the amino-anthraquinones of the formula preferably used for the preparation of the compounds according to the invention

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in which Y has the meaning given, ι may be mentioned

4-Amino-i-methylamino-anthraquinone, 4-Amino-i-hexahydroanilinoanthraquinone, 4-Amino-i-acetylamino-anthraquinone, 4-Amino-i-chloroacetylamino-anthraquinone, 4-Amino-i-butylamino-anthraquinone, 4 -Amino-i-stearoyl-amino-anthraquinone, 4-Amino-i-benzoylaminoanthraquinone, 4-Amino-1- (2-, 3- or 4-chlorobenzoylamino) -anthraquinone, 4-Amino-1- (2, 4- or 2,5-dichloro-benzoylemino) -anthraquinone, 4-amino-1- (2-, 3- or 4-nitro-benzoylamino) -anthraquinone, 4-amino-1- (4-chloro-3-nitro -benzoylamino) -anthraquinone, 4-amino-1- (3,5-dinitro-benzoylamino) -anthraquinone, 4-amino-1- (3-trifluoromethyl-benzoylamino) -anthraquinone, 4-amino-1- (4-methy1 -benzoylamino) -anthraquinone, 4 * amino-1- (4-methoxy-benzoylamino) -anthraquinone, 4-amino-1- (3-aulfamoyl-benzoyl-amino) -anthraquinone, 3-methyl-4-amino-1- (4-chloro-benzoylamino) -anthraquinone, 5-nitro-4-amino-1-benzoylamino-anthraquinone, 3-bromo-4-amino-1- (p-toluenesulfamido) -anthraquinone, 4-amino-l-anilino- anthraquinone, 4-amino-1- (4-methoxyanilino) -anthraquinone, 3-bromo-4-amino-1- (4-β βthy1-anilino) -anthrachir ϊ ^1, 3-bromo-4-amino-l- (2, o-diethyl - ^ - eethyl-anilino) anthraquinone.

All examples of the for the production of the erfindungegemäfl compounds used, derivatives of dicarboxylic acids of the formula HOCO-B-COOH, in which B has the meaning given, are preferably reactive derivatives such. B. esters or halides, especially fluorides, chlorides or

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. Bromides called of aliphatic dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, of heteroatom-containing aliphatic dicarboxylic acids such as diglycolic acid, thiodiglycolic acid, methylenebis-thioglycolic acid, such as methylenebis-thioglycolic acid, such as hydrogenated acid, methylenebis-thioglycolic acid, such as alcoholic acid. or - (1,9) '»Hydroxysuccinic acid, acetone dicarboxylic acid, acetylamino succinic acid, 2-acetylamino glutaric acid, of cycloaliphatic dicarboxylic acids such as cyclohexanedicarboxylic acid - (1,2) or - (1,4), camphoric acid, of bicyclic Dicarboxylic acids such as bicyclo [2,2, l]] - hepten- (5) -dicarboxylic acid- (2, j5), of unsaturated dicarboxylic acids such as fumaric acid, 1,2,3,6-tetrahydrophthalic acid, of mononuclear arylenedicarboxylic acids such as bensol carboxylic acid (1,2), - (1,3), or - (1,4), k- chloro-isophthalic acid, 5-nitro-isophthalic acid, 2-chloro-terephthalic acid, 2-nitro-terephthalic acid, 2,5-dichloro -terephthalic acid, HH ydroxyis © phthalic acid, 2,5-dimethoxy-terephthalic acid, 2,5-difluor-terephthalic acid, tetrachloro- 'or tetrafluor-terephthalic acid, of polynuclear, condensed arylenedicarboxylic acids such as naphthalenedicarboxylic acid- (1,4) - (1,5), or - (2,6), of polynuclear fused arylenedicarboxylic acids such as diphenyl-dicarboxylic acid (4,4 *), diphenylsulfon-dicarboxylic acid (4,4 '), azobenzene-dicarboxylic acid (4 _J 4 *), azoxybenzene-dicarboxylic acid (4, 4 ') hydrazobenzene dicarboxylic acid (4,4' benzophenone dicarboxylic acid (2,4 *), diphenyl ether dicarboxylic acid (4,4 *), diphenylmethanedicarboxylic acid (4,4 *) p-terphenyldicarboxylic acid (4 , 4, '*), 4 * -carboxy-biphenyl-4-azo-4-biphenyl-carbon

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aacid (4 *), or of heteroarylene dicarboxylic acids such as 2,5-furandicarboric acid, 2,5-thiophene-dicarboxylic acid, pyridine-dicarboxylic acid- (2,5), - (2,4), - (2,5) or - (2.6).

All examples of the amines of the formula (Y) used to prepare the compounds used according to the invention are called!

aliphatic amines such as methylamine, ethylamine, propylamine n-, iso- and tert-butylamine, dodecyl-, tetradecyl- or hexadecyl arain, 9-amino-heptadecane, stearylamine, substituted aliphatic Amines such as 2-amino or 1-amino-ethanol, 3-amine ° propanol, aminoacetic acid, 6-amino-hexanoic acid, aminoalkanes with a coastline Heteroatom such as 2- (2-amino-ethyl-amino) -ethanol- (l), 3-methoxypropylamine, 3-ethoxypropylamine, 3-butyloxypropylamine, 3- (2-ethylhexyloxy) propylamine, 2- Amino diethyl sulfide, alkenylamines such as Allylamine, cycloalkylamines such as cyclohexylamine, 2- (2-hydroxy-ethyl) -cyclohexylamine, 2-, 3- or '♦ -Methyl-cyclohexylamine, hexahydrobenzylamine, cycloalkylamines with interrupting heteroatoms in the Alkylene chain such as 3-amino-sulfolane, N- (2-amino-methyl) -piperazine, Aralkylamines such as benzylamine, 1-amino-1- or 2-phenyl-ethane, CJ-aminoacetophenone, optionally substituted arylamines with optionally fused or fused aryl nuclei such as Aniline, 2-, 3- or 4-chloro-aniline,

2,3-, 2,4-, 2,5-, 3,4- or 3,5-dichloroaniline, 2,4,5-trichloroaniline, 2-, 3- or 4-nitroaniline, 4-chloro-2- nitro-aniline, 5-chloro-2-nitro-aniline, J-chlorine - ^ - nitro-aniline, 2,5-dichloro-4-nitro-aniline, 2,4-dinitro-aniline, 6-drom-2,4-dinitro-aniline, 2-, 3- or M-amino

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toluene, 2-, 3- or 4-aminobenzotrifluoride, 4-chloro-2-aminotoluene, S-chloro - ^ - amino-benzotrifluoride, 4,5-dichloro-2-aminotoluene, k ~ _t 5 - Or 6-nitro-2-aminotoluene, 4-chloro-3-aminotoluene or benzotrifluoride, 2-ethylaniline, xylidines, 5-amino-1,3-bis-fluoromethylbenzene, 2-amino-1 , 3,5-trimethyl-benzene, 4-aminol-methyl-3,5-diethyl-benzene, ^ -amino-liJ-dimethyl-S-ethylbenzene, 4-dodecyl-aniline, 5,6,7 * 8-tetrahydro-naphthyl ~ amine- (l), or

- (2), ^ -amino-1-cyclohexylbenzene, 1- or 2-amino-naphthalene, 2-amino-anthracene, 1-amino-pyrene, 6-amino-chrysen, 2- or 4-amino-diphenylamine, ^ -Amino - ^ '- methyl-diphenylamine, 3-amino-4-roethyl-diphenylamine, 2-, 3- or 4-amino-diphenyl ether, 2-, 3- or 4-amino-1-methoxy-benzene, 4 -ChloΓ-5-nitΓO-2-ainino-lmethoxy-benzene, V-amino ^ -methoxy-diphenylamine, (2-hydroxyethyl) - (4-aminophenyl) sulfone, methyl- (4-aminophenyl) - sulfone, 4-amino-3-methoxydiphenylamine, 4-amino-1,3-dimethoxy-benzene, 6-chloro-4-amino-l, 3-dimethoxy-benzene, 2-amino-l, 4-diethoxy-benzene, 3-Amino-4-methoxy-diphenylsulphone, 4-Amino-acetophenone, 4-Amino-benzophenone, 2-, 3- or 4-Amino-benzamide, 'f-Amino-benzoic acid methyl or St -ethyl ester, 3 -Nitro-4-anlino-benzamide, ⁱ -chloro-2-aminobenzonitrile, amino-isophthalic acid dinitrile, 4-amino-isophthalic acid diamide, 6-aminonaphthoic acid arid (2), 3- or 4-amino-benzenesulphonic acid amide, 3-araino -benzenesulfonic acid (2-hydroxyethyl) amide, 4-amino-benzenesulfonic acid anilide, 2-amino-ben zoesäure.- sulfonic acid- (4) -diamide, 4-aroino-azobenzene, 4-amino-azobenzene carbonamide - ('4 *) or heteroaromatic amines such as 3- or 2-amino-dibenzofuran, 2-aminopyridine, 2-aminomethyl-pyridine , 9-ethyl-3-aminocarbazole, 2-

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Amino-4-methyl-pyrimidine, 3-Amino-1, .2,4-triazole, ^ 5-Amlno-2-phenylbenzotriazole, ^ Amino-thiazole, ^ -Amino-benzothiazole, 6-amino-2-methyl-benzthiazole, or ö-methoxy ^ -amino-benzothiazole.

The dyes produced fall in one suitable for pigments Form or can be converted into a form suitable for pigments by post-treatment known per se in fine distribution Can be converted, for example, by dissolving or swelling in strong inorganic acids such as sulfuric acid and discharging Ice cream. The fine division can also be done by grinding with or without Grinding aids such as inorganic salts or sand, if appropriate in the presence of solvents such as "" oluene, xylene, dichlorobenzene or N-methyl-pyrrolidone can be achieved. The color strength and transparency of the pigment can be changed by varying the aftertreatment to be influenced.

The pigments used according to the invention can be used to produce very real pigmented systems, such as mixtures with others Substances, preparations, paints, printing inks, colored paper and colored macromolecular substances are used. When mixed with other substances, for example, those with inorganic white pigments such as titanium dioxide (rutile) or to be understood with cement. Preparations are, for example, fluids with organic liquids or dough and finely pasted .ait water, dispersants and, if necessary, preservatives. The term paint stands, for example, for physically or oxidatively drying paints, Stoving lacquers, reactive lacquers, two-component lacquers, dispersing

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Blonde paints for weatherproof coatings and glue paints. Printing inks are to be understood as meaning those for paper, textile and metal printing. The macromolecular substances can be of natural origin such as rubber, obtained by chemical modification such as acetyl cellulose, cellulose butyrate or viscose, or produced synthetically such as polymers, polyaddition products and polycondensates. Plastic compounds such as polyvinyl chloride, polyvinyl acetate, polyvinyl propionate, polyolefins, for example polyethylene or polypropylene, polyesters, for example polyethylene terephthalate, polyamides, super polyaraids, polymers and copolymers of acrylic esters, methacrylic esters, acrylonitrile, acrylamide, butadiene, styrene, and polyurethanes and polycarbonates may be mentioned. The substances pigmented with the products claimed can be in any form. The compounds used according to the invention have excellent pigment properties and are not only excellent water-fast, oil-fast, acid-fast, lime-fast, alkali-resistant, solvent-fast, over-lacquer-proof, over-spray-proof, sublimation-proof, heat-resistant, vulcanization-resistant, but also very productive, easily distributed in plastic masses and of excellent lightness YJette Justice.
The parts given in the examples are Gt-wi ehtsteiüo.

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Example 1: "

a) 8 parts ^ - (^ - chlor-benzoylaminoJ-l ^ M-iJ-chlorophenylcarbaraoyl) -benzoylamino3-anthraquinone _# which are finely divided by grinding in a vibrating mill with 2 parts of xylene and 160 parts of sodium chloride and washing out of the common salt components are rubbed with a stoving enamel made of 25 parts of coconut oil alkyd resin (4o # coconut oil), 10 parts of melamine resin, 50 parts of toluene and 7 parts of glycol monomethyl ether on an automatic Hoover-Muller grinder. It carries the mixture to be painted on substrate, curing the coating by baking at 130 ⁰ C and receives violet deck strong coatings excellent Ueberladc ierechtheit and excellent light and weather fastness.

Pigmented stoving enamels with the same fastness properties are obtained by adding 15-25 parts of the specified alkyd resin or an alkyd resin based on cottonseed oil, ricin oil, castor oil or synthetic fatty acids and instead of the specified amount of melamine resin 10-15 parts of the mentioned melamine resin or a condensation product of formaldehyde with urea or with benzoguanamine is used. Similar to pigmented stoving enamels good fastness properties and a similar shade are obtained if instead of

of the given ^ - (^ - chloro-benzoylaminoJ-l - ^ - fJ-chlorophenylcarbamoyl) -benzoylamino] | -anthraquinone in fine distribution corresponding amounts ^ - ('l-chloro-benzoylaminoJ-lf ¹ »- (^ -methyl- phenylcarbamoylj-benzoylaminoj-anthraquinone,

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4- (4-chloro-benz.oylamino) -l- [ ⁱ l- (2,3-c3ichlor-phenylcarbamoyl) -benzoylaraino3-anthraehinone, ^ -Benzoylamino-lf] ¹ »- ^^ - dichlorpijeaylearbamoylD-benzoylamino-anthraquinone, ^ -Benzoylaminol ^ f4- (2,5-dichloro-phenylcarbamoyl) -benzoylaminoJ-anthraquinone or ^ -Benzoylamino-l - ^ - fM-nitro-phenylcarbamoylJ-benzoylaminoj-anthraquinone used.

b) Instead of the specified amount of pigment, 1 to 10 parts of a pigment are rubbed Mixture of titanium dioxide (rutile type) with one of the pigments specified in example la in a ratio of 0.5-50: 1 in the in example la specified varnish, varnishes with the same fastness properties and with increasing titanium dioxide content are obtained with the same further processing after white shifted violet hue.

c) The ^ - (^ - chloro-benzoylamino) -! -!] ¹ ! - (3 ~ ol \ lor-phenylcarbamoyl) -benzoylamino] -anthraquinone described in example la is prepared by adding 20 parts of ^ -amino-1 - ⁽¹ <-chlorbenzoylamino) anthraquinone as long as heated with 20 parts of terephthalic acid dichloride in ¹ JOO parts of nitrobenzene to 90-110 ⁰ C, until no starting amine is no longer detectable. The present in the form of red needles ¹ I- (^ -Chlor-benzoylaraino) -l- (4-chloroformyl-benzoylamlno) -anthraquinone is isolated and heated 10 parts of it in the presence of 3 parts of Ν, Ν-dimethylaniline, ¹ I parts 3-chloro-aniline in 200 parts of nitrobenzene bie to complete implementation of the Säurechioridee to 120-1 ^ 5 ⁰ C. the precipitate is filtered at 100 ⁰ C, washed with warm nitrobenzene, dimethylformamide, methanol and hot water and dried to violet in the form of needles present dye at 50 ° in a circulating air cabinet. The same compound is obtained if the nitrobenzene is replaced by 1,2-dichlorobenzene,

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if instead of Ν, Ν-dimethylaniline, equivalent amounts of soda, potash or pyridine is used.

The other compounds given in Example la are obtained if instead of ^ -amino-1- (M-chloro-benzoylaminoJ-anthraquinone equivalent amounts of ^ -amino-1-benzoylamino-anthraquinone or instead of 3-chloro-aniline, equivalent amounts of 2 , 3- or 2,: - dichloro-aniline or ^ -nitro-aniline used, or lO-chloro-benzoylaminoJ- ¹ JC ¹ I-chloroformyl-benzoylaminoj-anthraquinone in p-toluidine as solvent and reactant at 1 ^ 0-160 ⁰ C. The other dyes described in the following BelSDlelen are obtained in an analogous manner.

Example 2;

In 100 parts of a nitrocellulose lacquer consisting of UH parts of collodion wool (low viscosity, 35%, moist butanol), 5 parts of dibutyl phthalate, 40 parts of ethyl acetate, 20 parts of toluene, k parts of n-butanol and 10 parts of glycol monomethyl ether, 6 parts are finely divided brought ^ - (3-trifluoromethyl-benzoylamino-li ^ -phenylcarbamoyl-benzoylaminoj-anthraquinone rubbed in.

After spreading and drying, bluish red tones are obtained Coatings with excellent light and varnish fastness.

The same results to get when using nitrocellulose lacquers with 10-15 parts of nitrocellulose content, 5-10 parts soft ^fi wheeler content and 70-85 parts solvent mixture smaller using preferred aliphatic esters such as ethyl acetate, butyl acetate and aromatics such as toluene and xylene, and

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Shares of allphatic ethers such as glycol ethers and alcohols such as Butanol. plasticizers can be understood as meaning, for example Phthalic acid esters such as dioctyl phthalate, dibutyl phthalate, phosphoric acid esters, castor oil alone or in combination “With oil-modified alkyl resins.

Coatings with similar fastness properties are obtained from Use of other physically drying fuel, zapon and nitro lacquers, of air-drying oil, synthetic resin and nitro combination lacquers, oven- and air-drying epoxy resin lacquers, if necessary in combination with urea, melamine, alkyd or phenolic resins.

Coatings with similar fastness properties and a red shade are obtained when using appropriate amounts brought into fine distribution

M- (5-trifluoromethyl-benzoylamino) -1- [H- (2-chloro-phenylcarbamoyl) -benzoylamino] -anthraquinone, ^ - (J-trifluoromethyl-benzoylamino) -! - ^ - (^ - chlorophenylcarbamoylj-benzoylaminoj -anthraquinone, ¹ U (J-fluoromethyl-benzoylamino) -1- [ ¹ i- (2,5-dichloro-phenylcarbamoyl) -benzoylamino3 ~ anthraquinone, M- ( ¹ I-chloro-benzoylamino) -1- ( ^ - dodecylcarbamoyl -benzoylaminoj-anthraquinone, M- (i | -Nitrobenzoylamino) -l- ( ^| i-phenylcarbamoyl-benzoylamino) -anthraquinone, ^ -Benzoylamino-l-iH-phenylcarbamoyl-benzoylaminoJ-anthraquinone, M-benzoyl-methylcarino-b benzoylaminoJ-anthraquinone, ^ -Benzoylamino-li ^ -isobutylcarbamoyl-benzoylaminoJ-anthraquinone, M-Benzoylamino-l - ^ - (tert. butyl-carbamoyl) -benzoylamino] -

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anthraquinone, M-benzoylamino-l - ^ - tetradecylcarbamoyl-benzoylaeino) -anthraquinone, M-benzoylamino-l- | [^ - (* kihlc «r-phenylcarbamoyl <) - benzoylamino] -anthraquinone instead of !! benzoylaniino) -l_ (l | -phenylcarbainoyl-benzoylainino) -anthrachlnon.

Example 3;

5 parts in fine distribution accommodated ^l UBenzoylamlno-l - ^[[| U (n-butylcarbainoyl) -benzoylanilncf] -anthrachlnon are tanned in 100 parts of a paraffin-free drying unsaturated polyester resin in a porcelain ball mill. With the grinding process, 10 parts of styrene monomer, 5 parts melamine Formaldenyd resin and 1 part be thoroughly stirred a paste of Ho parts of cyclohexanone peroxide and 6o parts of dibutyl phthalate and finally 4 parts TrocknerlOeung (10 £ lges cobalt naphthenate In Testbensin) and 1 Tell SiIikonöllOsung (l- ^ Ig in xylene) added. Nan applies the mixture to primed wood and receives a high-gloss, “race-proof and weather-proof bordo-colored finish with excellent lightfastness.

Is used instead of the reactive varnish based on Polyester resin amine-curing epoxy resin lacquers with dipropylenediaain as an amine component, bordo-colored coatings are obtained that are extremely weatherproof and blooming.

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Example *

100 parts of a 65-year-old solution of an aliphatic polyester with approx. Q>% free hydroxyl groups in glycol monoethyl ether acetate

are brought into fine distribution with 5 parts * l- (Juchlor

tenzoylaminojfl- (4-me

rubbed and then with 4H parts of a 67 Jfogen solution dee reaction product of 1 mole of trimethylolpropane with 5 moles Toluylene diisocyanate mixed well. Without affecting the pot life, the mixture and reaction result after application of the components high-gloss red-violet polyurethane coatings with excellent blooming, light and weather resistance.

Pigmentation of similar fastness is obtained when using other two-component lacquers based on aromatic or aliphatic isocyanates and polyethers containing hydroxyl groups or. Polyesters, as well as polyisocyanate varnishes resulting from moisture-drying, polyurea varnishes. Pigmentations of similar fastness properties and similar hues are obtained when using appropriate amounts of 4 - (^ - methoxybenzoylamino | -1- £ * - (n-but y 1- carbamoyl) -benz oylamino] - anthracinone, k- (^ -cailor-b ^ naoylaminoj-lf ^ - (S ^ dichloro-phenylcarbamoyl) -benzoy aeinoj-anthraohinon, k (^ chloro-benzoylaniino) - - ^ ¹ - (2 _r chloro-5-trlfluorroethyl-phenylcarbamoyl) benzoylamino ] -anthr aquinone, 4- (M-CSilor-benzoylaniino) -l- [ ¹ l- ( ⁱ l-dodecyl-phenylcarbaraoyl) -benzoylamino] J-anthraquinone, ^ - (J-chloro-benzoylamino) -anthraquinone) -l - (4-methylcarbamoyl-benzoylamino) -anthraquinone or ^ - {a-Cfalor-benzoylaminoJ-l - ^ - hexadecylcarbamoyl-

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benzoylaminoVanthraquinone instead of the dye given above in Example k.

Example 5:

5 parts of a fine dough obtained by kneading 50 parts M- (4-chloro-benzoylamino) -l - [] 4- (U-sulfamoyl-phenylcarb * amoyl) -benzoylamlno [] - anthraquinone with 15 parts of an aryl polyglycol ether emulsifier and 35 parts of water are with 10 parts of barite as filler, 10 parts of titanium dioxide (Rutile type) as a white pigment and 40 parts of an aqueous emulsion paint, containing approx. 50 # polyvinyl acetate, mixed. The color is spread and, after drying, red paints are very good fastness to lime and cement, and are also extremely fast to weather and light.

The fine dough obtained by kneading is equally suitable for pigmenting clear polyvinyl acetate emulsion paints, for emulsion paints, the copolymers of styrene and Contain maleic acids as binders, as well as dispersion dyeing based on polyvinyl propionate, polymethacrylate or butadiene styrene.

Paints similar hue and similar fastnesses is obtained if, instead of the specified ^ - (M-Chloro-benzoylaininoJ-lf] ¹ '- ^ - sulfamoyl -phenyloarbsmoyl) benzoylamino] -anthraquinone corresponding amounts of 4- ^(J i-chloro-benzoylamino ) -l- (4- phenylcarbamoylbenzoylamino) -anthraquinone, ⁱ * - (4-chloro-benzoylamino) -l- [] ¹ »- (2-

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_BATH

chlorophenylcarbamoyl) -benzoylEailno] -anthraquinone _> U- (4-

benzoylamino) -l-f ^ - (^ - chlorophenylearbaT.oyl) -benzoyiamino3-anthraquinone, ^ - (^ - chloro-benzoylaniinoJ-l-f ^ -in-butylcarb = amoyl) -benzoylamino [] - anthraquinone * n, * 1- (2-nitro-benzoylamino) -l- p- (n-butyl-carbamoyl J-benzoylaminoJ-anthraquinone, ^ - (J-Nitro benzoylamino) -1- (4-phenylcarbamoyl-benzoylamino) -anthraquinone,

amoyl) -benjEoylaraino] -anthraquinone, * t- (3 * 5-dinitro-benzoylaraino) -l- (ΐ-stearylcarbamoyl-benzoylainino) ~ anthraquinone or ^ - (il-chloro-benzoylaniinoJ-l-f ^ -cyclohexylcarbainoylbenzoylamino) -anthraquinone used.

Example 6:

10 parts of the pigment paste mentioned in Example 5 are mixed with a mixture of 5 parts of chalk and 5 parts of 20% glue solution. A red wallpaper coating color is obtained, with which one achieves excessive levels of excellent lightfastness. Other non-ionic emulsifiers such as the reaction products of nonylphenyol with ethylene oxide or ionic wetting agents such as the sodium salts of alkylarylsulfonic acids, for example dinaphthylmethanedisulfonic acid, sodium salts of substituted sulfofatty acid esters and sodium salts of paraffin sulfonic acids can be used in a combination of paraffin sulfonic acids to produce the pigment dough.

Example 7:

A mixture of 65 parts of polyvinyl chloride, 35 parts of diiso-

in 571-19-109843/1396

octyl phthalate, 2 parts dibutyltin mercaptide, 0.5 part Titanium dioxide and 0.5 part 4- (lUChlor-benzoylamino) -

, l-f ^ - ^ - chlorophenylcarbamoylJ-benzoylamino ^ -anthraquinone, which has been finely divided by grinding with sodium chloride in the presence of white spirit, is put on a rolling mill colored at l65 ° C. You get an intense bordo-!. red-colored mass that can be used for the production of foils or moldings. The coloring is excellent Fastness to light and very good plasticizer fastness.

Staining red clay and similar fastness properties are obtained when the specified ¹ t ⁽¹ »chloro-benzoylamino) -l- £ ^| i- (2-chlorophenylcarbamoyl) -benzoylaminol-anthraquinone by corresponding amounts of M - (^ - chlorobenzoylainino) -l- | ii- (2,5-dichlorophenylcarbamoyl) -benzoylamino]] - anthraquinone, ^ - (^ - dilor-benzoylamino JI- ^ ¹ U ( ¹ J -trifluoromethyl-phenylcarbamoyl) -benzoylamino] -anthraquinone, 4- (4-oilor-benzoylainino) - l-. | [ ¹ U ( ⁱ umethoxyphenylcarbamoyl) -benzoylamino] - anthraquinone, 4 - (M-chloro-benzoyl ~ amlnoJ-l-fl-iJ-sulfa-cyclopentyl-SiS-dioxld-carbaiDoylJ-benzoylamino] [- anthraquinone, ¹ U (J-trifluoromethyl-benzoylamino) -l- (4 -. butylcarbanjoyl-benzoylamino) -anthraquinone or 4- (4-Nitroben2oylamino) -l- (4-phenylcarbamoyl-benzoylaniino) - anthraquinone replaced.
Example 8;

0.2 parts, finely divided, 4- (4-chloro-benzoylamino) - ! - (^ - phenyicarbamoytbenzoylaininoy-anthraquinone be with 100 parts Mixed polyethylene, polypropylene or polystyrene granulate. the

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Mixing can either be done at 220 to 28o ° C directly in an injection molding machine sprayed, or processed into colored rods in an extruder or into colored skins on the mixing mill will. The rods or skins are, if necessary, granulated and injected in an injection molding machine.

The red briquettes have very good light and migration fastness. In a similar way, at 280-3OO ° C, if necessary below Nitrogen atmosphere, synthetic polyamides made from caprolactam or Adipic acid and hexamethylenediamine or the condensates of terephthalic acid and ethylene glycol can be colored. -. '

Example 9;

1 part finely divided ^ -Benzoyiaipino-l-Jf ^ -phenylcarbamoyl J-benzoylaminoJ-anthraquinone, 10 parts titanium dioxide (Rutile type and 100 parts of a mixed polymer in powder form based on acrylonitrile-butadiene-styrene are mixed and colored on a roller mill at 14o-18o °. Man receives e.in burgundy fur, which is granulated and in an injection molding machine is sprayed at 200 ~ 250 ° C. Wine-red moldings are obtained with very good lightfastness and migration fastness as well as calculated ones Heat resistance.

In a similar manner, but at temperatures of l80-220 ° C and without the addition of titanium dioxide plastics are colored based on cellulose acetate, cellulose butyrate and their mixtures with similar fastnesses.

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! , 109843 / 139B

Example IQ; **

• 0.2 parts of ¹ <-Benzoylamino-l- [il- (3, ⁱ -dichloro-phenylcarbamoyl) -benzoylamino] -anthraquinone are finely divided with parts of a plastic based on polycarconate in an extruder or in a kneading screw at 25O- Mixed at 28o ° C and processed into granules. A purple, transparent granulate of excellent lightfastness and heat resistance is obtained.

Example 11;

90 parts of a weakly branched polypropylene glycol with a molecular weight of 2500 and a hydroxyl number of 56, 0.25 part of endoethylene piperazine, 0.3 part of tin (II) octoate, 1.0 part of a polyether siloxane, 3.5 parts of water, 12, 0 parts of a grind of 10 parts of divided ^ -Benzoyiamino-l-Ct-methyl- • carbamoyl) -benzoylaminoj] -anthraquinone in 50 parts of the specified polypropylene glycol are mixed well with one another and then mixed with ¹ ^ parts of toluylene diiscyanate (.'Bo % 2 , 4- and 20j6 2,6-isomer es) mixed intimately and poured into a mold. The mixture becomes cloudy after 6 seconds and foam formation occurs. After 70 seconds, an intensely wine-red colored, soft polyurethane foam has formed, the pigmentation of which has excellent lightfastness.

Reddish blue flexible polyurethane foams similar to lichtecliter Pigmentation is obtained when replacing the ^ -Benz-oylamino- ! - (^ - methylcarbamoyl-benzoylaminoj-anthraquinone by ent-

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Speaking amounts of 2-bromo-4 ~ { ¹ i -., Tieth; yl-anilino) -l- ( ¹ i-phenylcarbamoylbenzoylamino) ~ anthraquinone, S-bromo-mi ^ -methyl-2,6-diethylanilino JI- ( ¹ I-phenylcarbamoyl-benzoylamino) -anthraquinone, ¹ UAnIlInO-I- [ ¹ J - (M-methyl-cyclohexylcarbamoylJ-benzoylaminoQ-anthraquinone, ¹ UAnIHnO-I- [ ¹ U (hexahydrobenzyl-carbamino-benzo-benzohrachamoylj-benzoylamino) , 4-AnIlInO-I- [ ¹ U (2-hydroxy-ethylcarbamoyl) -benzoylamino] -anthraquinone, ¹ UAnIlInO-I- [ ¹ U (3-hydroxypropylcarbamoyl) -benzoylaminoj-anthraquinone or ¹ UAnIlInO-I- [ ¹ U (J-chlorophenylcarbamoyl) -benzoylaznino] -anthraquinone,

Example 12;

90 parts of a weakly branched polyester made from adipic acid, diethylene glycol and trimethylolpropane with a molecular weight of 2000 and a hydroxyl number of 6o are mixed with the following components: 1.2 parts of dimethylbenzylamine, 2.5 parts of sodium castor oil sulfate, 2.0 parts of an oxethylated, benzylated oxydiphenyls, 1.75 parts of water, 12 parts of a paste, prepared by rubbing in 10 parts finely divided, h- (4-chloro-benzoylamino) -l-Q4- (k - carbamoyl - phenyl «carbamoyl) - benzoylamino] anthraquinone in 50 parts of the polyester indicated above. After mixing, 40 parts of tolylene diisocyanate (63% 2,4- and 35% 2,6-isomers) are stirred in and the mixture is poured into a mold and foamed.

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After 60 seconds, a red-violet colored, soft polyurethane foam has formed, the dyeing is characterized by very good light fastness, green-blue dyeing of similar light fastness is obtained when using appropriate amounts of 4-anilino-1- [4- (2,3-dichloro-phenylcarbamoyl) -benzoylaminoJ -anthraquinone, 4-anilino-1- [~ 4- (2,5-dichloro-phen ^ j oarbamoyl) -benzoylamino] -anthraquinone, 4-anilino-1-L4- (4-carbamoylphenylcarbamoyl) -benzoyl ~ aminq] -anthraquinone, 4- (4-methoxy-anilino) -1- £ 4- (n-butylcarbamoyl) -benzoylaalno "J -anthraquinone or 4- (4-methyl-anilino) -1- £ 4- (n-Butylcarbamoyl) -benzoylamine-anthraquinone instead of the indicated 4- (4-chloro-benzoy lamino ) -l- (4- (^ -carbamoyl-phenylcarbamoyl) -benzoylaminoj-anthraquinone.

Red inserts of similar lightfastness are obtained if, instead of the specified ^ - (^ - chloro-benzoylaminoJ-l - ^ - Ci-carbamQylphenylcarbamoylj-benzoylaminoj-anthraquinone, corresponding amounts of ^| l-chloroacetylajnino-l- ( ^l * -benzylcarbamoyl-benzoylamino) anthraehinCMi _; ^ l-valerylamino-lf ¹ »- (2-phenyi ~ ethylcarbamoyl) -benzoylamlno3-anthraquinone, 'f-stearoylamino-l - ^ - i ^ -carbethoxy-phenylcarbamoylJ-benzoylamino] sulfanthraquinone, ^ - -benzoylaralnoJ-li ^ -phenylcarbamoyl-benzoylamino) -anthraquinone or S-methyl-'J-Cl-chloro-benzoylamino) - ¹ I- (h -phenylcarbamoyl-benzoylamino) -anthraquinone used *

Example 13;

With a printing ink made by rubbing 35 parts in.

1-Benzoylamino-1- (4-phenylcarbamoyl-benzayiaoiino "| -anthraquinone) and 65 parts of linseed oil and the addition of 1 part of Sleoattr (Co-naphthenate, 50 ^ ig in white spirit) red offset prints are higher

Le A 11 571 -24- 109843/1395

Keep brilliance and color strength and very good light and lacquer fastness. Use of this printing ink in book, light, stone or steel engraving leads to red prints with similar fastness properties. Used nan the pigment for coloring tinplate printing or low-viscosity gravure printing inks or printing inks, red prints are more similar Fastnesses.

If the ty-benzoylamino-1- (4-phenylcarbamoyl-benzoylamino) -anthraquinone is replaced by corresponding amounts of M-CJ-chloro-benzoylamino) -1- (2,5-dichloro-4-phenylcarbamoyl-benzoylamino) -anthraquinone, 4-Benzoylamino-li ^ -hydroxy-J-phenylcarbamoyl-benzoylarainoJ-anthraquinone 4_ (i | «<3 ₁ lor-benzoylamino) -l- (6-phenylcarbamoyl-naphthoyl- (2) - 'ι

amino) -anthraquinone, ^ - (^ - chloro-benzoylaniinJ ^ C ^ amoyl-phenyl) -benzoylaminoJ-anthraquinone, M-Benzoylajaino-1- £ * J - (M -phenylcarbamoyl-phenoxy) -benzoylaniinoj-anthraquinone, M-benzoylaraino -l- ^[1 J- (2-phenylcarbamoyl-benzoyl) -benzoylaraino] -anthraquinone it-Benxoylaraino-lf ^ -cIF phenylsulfonyl) -benzoylaraino] anthraquinone, A- (^, - benzoylaiaino) -l- (5-phenylcarbaiBoyl -valeryla «ino) - anthraquinone, prints of a similar color with similar brilliance and authenticity are obtained.

example

From 10 parts of the fine pigment dough given in Example 5, parts of tragacanth 3 jftg, 100 parts of an aqueous 50% egg album in solution and 25 parts of a nonionic wetting agent is a Preparing printing paste. A textile fiber fabric is printed, and attenuated C and receives a red print, which is distinguished by excellent real

X · - * Ii 571 -25-108843/1386

BATH

uniqueness, especially lightfastness. In the pressure approach of the Traganths and egg albumin, for example those Britishgum or cellulose & lykolat can be used in place more usable for the fixing on the fiber binder based on synthetic resin.

Example 15:

A mixture of 100 parts of Cre * pe light, 2.6 parts of sulfur, 1 part of stearic acid, 1 part of mercaptobenzothiazole, 0.2 part of hexamethylenetetramine, 5 parts of zinc oxide, 60 parts of chalk and 2 parts of titanium dioxide (anatase type) is turned on a mixing roll mill at 50 ° C with 2 parts of ^ -Benzoylamino-l - ^ - in-butylcarbamoylJ-benzoylaminoj-anthraquinone and then vulcanized ^{at I 1} JO ^{0 C for 12 minutes.} A wine-red colored vulcanizate with very good lightfastness is obtained. Example 16;

100 parts of a 20 jfctgen aqueous paste of ^ - (^ - trifluoromethylbenzoylaminoJ-l-J ^ -C ^ -nitro-phenylcarbamoylJ-benzoylamino] anthraquinone, prepared for example by dissolving the Dyestuff in 96% sulfuric acid, discharge on ice, Piltrleren and neutral washing with water, will be 22 500 parts an aqueous, approximately 9% viscose solution in the stirrer added. The colored mass is stirred for 15 minutes, then deaerated and subjected to a spinning and desulfurization process subject.

Orange-red colored threads or films with very good lightfastness are obtained.

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Itelnrot pigmented threads or foils of similar authenticity receive one, if one, with the finely divided M-i'i-chloro-benzoylaminoJ-l- ^ l-ehlor-phenylcarbamoylJ-benzoyl-r amino] anthraquinone colored solution of acetyl cellulose in acetone or a 15-25% solution of polyacrylonitrile in dimethylformamide subjected to a dry spinning process.

Example 17;

10,000 parts of a paper pulp containing k parts of cellulose per 100 parts are treated in the Hollander for about 2 hours. During this time you are in each quarter-hour intervals I ¹ parts rosin size, 30 parts of an approximately 15 #igen Pigmentdispereion obtained by grinding in the ball mill ¹ of 1.8 parts of ¹ J - (^ - ^ trifluoroethyl-benzoylaminoJ-.l- -C ^ -chloro-phenylcarbaiiioylJ-benzoyl ^ ¹¹¹⁰ D-anthraquinone having ¹ 1.8 parts of dinaphthylmethanedisulfonic acid and 22 parts water, then 5 parts of aluminum sulfate to. After completion on the paper machine to obtain a blue- "tichig red-colored paper of excellent light fastness .

Example 18;

The red pigmented paper produced according to Example 17 is mixed with the 55 # solution of a urea-formaldehyde resin in Soaked in n-butanol and baked at lHo ° C. One receives a bluish red laminate paper with very good migration and excellent lightfastness.

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Laminate paper with the same fastness properties is obtained by lamination of a paper which has been printed in the gravure printing process with a printing ink which has the red pigment paste specified in Example 5 and contains water-soluble or saponifiable binders.

Examples 19 -

According to Example la, but using the corresponding amounts of the dyes given in the following table, finely divided instead of, 4- (^ - (fo \ or_-Ji $ nzoylpgaij \ oJ-I - [^ (Λ-ChlorophenylcarbamoyLtoenzcylamino ^ - anthraquinone, you get real pigmented stoving enamels in the colors given in the table:

Ex.

dye

hue

carbamoyl) benzoylamino] anthraquinone

k - ( k -chloro-benzoylamino) -1- £ Μ - ( k -chlorophenylcarbamoylj-benzoylamino ^ -anthraquinone ^ - (^ l-chloro-benzoyianiinoJ-l-f'l-Ci-carbamoylphenylcarbamoylJ-benzoylaminoJ-anthraquinone.

¹ I- (* l-chloro-benzoylamino) -l- (^ -phenylcarbamoylbenz oy1amino) -anthraquinone

M- (i »-chloro-benzoylaniino) -l- [ ¹ » - (2-chlorophenylcarbamoyl) -benzoylamino [] -anthraquinone

l »- (l | -Chlorobenzoylamino) -l- [l» - (3-dichlorophenylcarbamoyl) -benzoylamino1 anthraquinone

Red

bluish, red

bluish, red

Red

bluest. Red

bluish, red

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Bolep ± el

Dye

Coloring »

23 2 * 27 28 29 30

32

3% 35 3 « 37 3 » 39 ko kr

4_ (it-chloro-bensoylaaino) -1 - £ k- (2-ni tropheÄylcarba * oyl) -benzoylaiiino] -anthraquinone k ~ (4-chloro-benzoylamino) -1- £ 4- (3-ni trophenylcarbanoyl) - benzoylaeinoJ-anthraquinone% - (it-chloro-benzoylajnino) -1 - [k- ( k-ni trophenylcarbanoyl) -benaoylajBino ^ -anthraehanone

red br bluish, red Red

- blue, red Red Red

Red

ret Red Red

phenyl c arbaeoyl) -benzoylaeino ^ J-anthraquinone 4- (4-chloro-benzoylanino) -1 - [[4- (3-eulf aeoyl phevylcarbanoyl) -benzoylaminoj-anthraquinone 4- (4-chloro-benzoylanino) -1- £ 4- (3-thia-cyclopen tyl-S, S-dioxide-carbaMoyl) -benzoylaainoJ-anthra-

chinone

4-Benseylamino-1 - £ 4- (2-chloro-phenylcarbaeoyj) - benze] rla> iino]] - anthraohlnon

4- Bensoylaaino »1 - [[4- (3-chloro-phenylcarbaeoyl) - bens oylaalnej-anthraquinone

4>BenzoylaMiBo> t- [| 4- ( 2, 5-di chi or- phenyl car · - aaoyl) -benzoylaaino] | -anthrachlaon 4-Benzoylaaino-1- £ 4- (4-nitro-phenylcarbaeoy ^ - bensoylaaino ^ -anthraquinone

4- (4-M * thoxy-b * n * oyla «iino) -1- [4- (2,5-chloro-bluish, red phenyl «arbeJBoyl] -bensoplaaine ^ ftnthraquinone

4- (4-methoxy-benzoylamino) -1 - [4- (4-nitro- -violott

phenylearbaaoyl) -benseylatinoj-antfariohlnon 4- (3-Triflttereetkyl-beaeeylejaine) -4 -.] [4-phanyl- mouse, red earbaswyl-benseylasuLne) -anthrachlBon

i "- (3-trifluoro" ethyl-ben "oyla" ino) -i- [4- (4- blaoat. red

chlorophenylcarbaaoyl) benzoylajiiBo]] - anthraquinone 4 ~ (4-Hitre-benxoylasiitto) - '1- (4 * aothylcarbaJsayl- bluust «red be & aoylaaiao) aathraquinone

4- (4-Kltre-benmoyla «ino) -1- [i» - (n-butyl blue, red earbsjsoyl) -benzoylamlmo J-anthrachlnon 4- (4-Mitroben »oylejiino) -1- £ 4- (n-dodoeyl- bluust · red carbaswyJ) -bensoylaaine [] -anthrachijaoA

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«• igpiol dye 5? Colors »

k2 ^ - (4-Nitro-benzoylaeino) -1- [4- (2-ChIor- red

phanylcarbamoyl ^ benzoylajnino ^ -anthraquinone k $ 4- (J »-nitro-b * nsoylamino) ~ 1- £ i» - (Jt-cblor- blauet, red

phenylcarbaaoy1) -benaoylamino} -anthraquinone kk 4- (4-Nitro-b0nzoyla «ino) -1- [4- (2,5-UiChIOr- blueat. Red

phanylcarbamoyl) -bansoylaninoJ-anthrachlmm kü 4- (2, ^ - dichloro-benzoylamino) -i - ^ - i5-carboxy- red

pentylcarbaaoyl) -benxoylaninoj | -anii'rachlnon k6 i »- (2 _f 4-Diohlor-ben» oylai _n ino) -1- / 4- [2- (2-hyclroxy- red

äthylaaiiiio) -Kthylcarbani oyij-ben »oyla» ino j -

antbjracbJ-non k7 ⁱ "- (2,4-Dlchlor-bon" oylajBino) -1- £ '^ - (3-butoxir- red

propylcarbaaoyl) -bonxoylaeinoj-anthraquinone HS 4- (2,4-dichlorobenzoyl> mino) -l- [4- (3,5-dichloro-red

phenylcarbaaoyl) -bensoylajaino ^ -anthracliinon k9 4- (2 _t 5-Oic ^ lor-benzo _y laaino) -1 - {['t- (2-fitkylaetr- red

capt o-ttthylcarbamoyl) -benzoy laaiAo2-antb.radii.non 4- (2,5-dichlorobenzoyla «ino) -l- £ 4- (b« n »oyl- red

■ • tbylcarbamoyl) -b & oaoylaaimoJ-anthiachinan 4- (2,3-dichloro-b * n "oyla" ino) -1 - [] 4- (2 _t ^, 5-triplet red

chlor-phanylcarbajBoyl) -bonsoylaalno J-antnrachlnon 4 - (^ i. | Utbyl-b «n« oyla »ino) -1 - (] J» - (5-chloro-2-nltro- red phenylcarbaapyl} -benzoylaainoj-utttaracbiiioa

4- (4-ll "tbyl-b * n" oyla "ino) -1- [i" - (2, i "-dinitro-red phenylcarbaaoyl) -banzoylawinoj-aiithracbtno «

5% 4- (i »-M * methyl-ben» o7laeino) -1- [4- (o-broe-2,% - <li red ni tr "-ph" nyl carbaaoyl) -lianzoylaalnoj-anthraehinon J "- (% - M * thyl-benzoyla" ino) -1- [4- (4-e "ethyl red phanylcarbaaoyl) -banBoylaalnoJwanvhrachinon i | -Ao «tyla« ino-1 - [] 4- (4-e * thyl-phenylcarbaeoyl) - red bansoylaainoj-antbracbinon

VNitro-4-b * nzoyla «ino-1- £ J» - (l »-eotbyl-phenyl- *" ot carbaaoyl) «bonzoylaaiinoj-ajithrachlnon 2-Bro "-1- [| i" - (4 - "*" hyl-ph * nylcarbaeoyl) -benzoyl- red aein ·] - ^ - (4-aatbyJHioaaolaalfaal4 «^ anthraquinone J "- (J ^ -Tr if luor" * thyl-b * nzoylaeino) -1- [i | - (-% - e · - red tbyl-phanylcarbaaoyl) -banaoylaeinoJ-anthrachlnon

57i _3o 1098 * 3/1395

BATH

·, 17687A5

Β · 1 game dye ^ _ shade

4-Benzoylamino-1 ~ £ U- (5-chloro-2-trifluoromethyl-red phenylcarbamoyl) -3eiizoylamino-anthraquinone

i | -Benzoylamino-1-j [J »- (5-nitro-2-methyl ~ red phenylcarbamoyl) benzoylaminol anthraquinone

i | -Benzoylamino-1- ^ U- (2 ~ chloro-5-diethyl red phenylcarbamoyl) benzoylamino "} - aiithraquinone ^ -Benzoylamino-1- ^ 4- (3,5-bis-trifluoromethyl- red phenylcarbamoyl) benzoylamino] anthraquinone

6k 4-Benzoylami »o-1- [] ⁱ 4- (2 _l 4,6-trimethyl-red

phenylcarbamoyl) benzoylaminoJ-anthraquinone 4- (3-chloro-benzoylamino) -1- [4- (i4-methyl-3,6- 'red diethyl-phenylcarbamoyQj-benzoylaminaJ-anthraquinone U ~ (3-chloro-benzoylamino) -1- £ ^ - (5 | 6,7,8-tetra-red hydro-naphthyl- (1) -carbamoyl) -benzoylamino] J-antbrachinone

^ - (S-chloro-benzoylaminoJ-i - ^ - i ^ -cyclohexyl- red phenylcarbamoyl) -benzoylaminoJ-anthraquinone 4- (3-chloro-benzoylamino) -1- (naphthyl- (1) - red carbaraoyl-benzoylamino) -anthraquinone 4- (U-chloro-benzoylamino) -1 - ^ - anthracenyl- (2) - red carbamoyl-benzoylamino) anthraquinone

7.0 ii-iit-chloro-benzoylamino ^ i-i ^ -pyrenyi-i 1) - red carbamoyl-benzoylamino) -anthraquinone ^ - (U-chloro-benzoylamimO-i-j ^ -iU-anilino- red phenylcarbamoyl) -benzoylaminoj-anthraquinone ^ - (4-chloro-benzoylami_no) -1 - ^ - (^ -phenoxy- red phenylcarbamoyl) benzoylamino ^ j-anthraquinone 4- (4-nitro-benzoylamino) -1 - ^ U- [J * - (4-methyl-red anilino) phenylcarbamoyl] benzoylaminoj anthraquinone

^ - (U-Nitro-benzoylamimO-i - ^ - ^ - i'i-niethoiy- rot anilino) -phenylcarbamoyl] | -benzoylaminoV anthraquinone

! »- (ii-Nitro-benzoylaminoJ-i-fU-i ^ -methylsul- red fonyl-phenylcarbamoyl) -benzoylaminoj-anthraquinone

571-31-109843/1395

B «J game dye *** I IOQ 1 * 9 hue

4- (3-Trifluonnethyl-benzoylamino) -1- £ U- (2-meth- red oxy-5-phenylaulfonyl-phenylcarbaeoyl) -benzoylaminoT-anthraquinone

U- (3-trifluoromethyl-benzoylaroino) -l- £ U- (U-ben- red zoyl-phenylcarbamoyl) -benzoylam iuo ^ j-anthraquinone

4- (3-trifluoromethyl-benzoylamino) -1 - [] i | - (4-ace- red tyl-phenylcarbamoyl) -benzoylaminoj anthraquinone

4- (3-trifluoromethyl-benzoylainino) -l- £ i | - (3-carb- red amoyl-phenylcarbamoyl) -benzoylamino ^ -anthraquinone

4- (3-Nitro-benzoylamino) -1 - [] 4- (5 ~ chloro-2-cyano-red phenylcarbaraoyl) benzoylamino ^ -antlirachinon

1- (3-Nitro-benzoylamino) -1-1- [4- (2 _t 11-dicyano-red phenylcarbamoyl) -benzoylamino ^ -anthraquinone

4- (3-Nitro-benzoylamino) -1 - [[^ 2 _l 4-dicarbajnoyl-red phenylcarbamoyl) -benzoylamino-1-anthraquinone

4- (3-nitro-benzoylatnino) -1 - ([4- (6-carbainoyl-red naphthyl- (2) -carbaMoyl) -benzoylaeino] | -anthraquinone

Qk k- (3-Nitro-benzoyla "ino) -1- | ^ - £ 2-chloro-5- (2-hydroxylsulfamoyl) -phenylcarbaeoyl J-benzoylamino-anthraquinone

U- (5-chloro-2-cyano-benzoylamino) -1 - [[U- (U-ChIoT- red , phenylcarbamoyl) benzoylamino'j-anthraquinone

U- (3-nitro-benzoylamino) -1- £ U- (U-phenylaulf- red amoyl-phenylcarbamoylJ-benzoylaminoJ-anthraquinone

U- (3-sulfamoyl-benzoylamino) -1> - [^ II- (U-methyl-red phenylcarbamoyl) -benzoy laminol-antJir.achinon

S-Nitro-i-iU-chloro-benzoylaminoJ-U- (U-phenyl- red carbanoyl-benzoylamino) anthraquinone

i-JU- ^ Phenylcarbamoyl-benzoylaminoJ-U-Cl-methyl- red benzenesulfamido) -2-phenylsulfonyl-anthraquinone

1 _t 5-dibenzoylamino-U- (4-phenylcarbaaioyl-red benzoylamino) -anthraquinone

9t U- (3-trifluoromethyl-benzoylaraino) -l - [[U- red (U-trifluoromethyl-phenylcarbamoyl-I-benzoylamino] -anthraquinone-2-carboxamide

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B "l" piel

dye

hue

92 93

95 96 97 98 99

tOO 101 tO2

Red

Brown

4-Benzoylamino-£ - ** - ^ - carbamoyl - ^ - eulfamoylphenylcarbamoyl) -benzoylaminoJ-anthraquinone U-Benzoylamino-1-Q ^ - (4-phenylazo-phenylcarbamoyl) -benzoylamino ^] - anthraquinone it-Benzoylamino-i -fU-fU-iU-carbamoyl-phenylazo) - brown phenylcarbamoyl ~ j-benzoylaminoj-anthraquinone 4-benzoylamino-1 - (4-pyridyl- (2) -carbaraoylbenzoylamino) -anthraquinone
4-Benzoylamino-1-J [If- (c / C -picolylcarbamoylbenzoylamino) anthraquinone

4-Benzoylamino-1- £ ** - (2-phenyl-benztriazolyl- (5) -carbamoyl) -benzoylainino] -anthraquinone it-Benzoylamino-1 - (* ♦ -thiazolyl- (2) -carbamoylbenzoylamino) -anthraquinone

4-Benzoylamino-1 - ^ - (2-methyl-benzthiazolyl- (6) -carbamoyl) -benzoylamino-1-anthraquinone 1-benzoylamino-1 - (1-benzthiazolyl- (2) -carbamoyl-red benapylamino) -anthraquinone

4- (4-chloro-benzoylamino) -1- £ ⁱ t-chloro-3- ( ¹ * -chlor- red phenylGarbamoyl) ^ benzoylamino ^ -anthraquinone ^ - (^ - chloro-benzoylaniino) -1- ^ 3 ^ ( ^z i-chloro-red phenylcarbamoyl) -benzoylaminoJ-anthraquinone

Red

Red

Red

Red

Red

Examples 105-1 * 16;

If you use according to Example 2 instead of ^ - (^ - trifluoromethyl-benzoylluBinoJ-l-i ^ -phenylcarbamoyl-benzoylaminoJ-anthraquinone Corresponding amounts of the finely divided dyes given in the following table are obtained which are genuinely pigmented Nitro lacquers with the colors specified in the table:

Le A 11 571

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Beispi el Farbs toff 17 KQ74 S color

103 4- (2,5-dichloro-benzoylamino) -l- [ ^I »- (n-butyl-

carbamoyl) benzoylamino]] - ar; thrachinone red

10 ¹ I ^ ~ C'-Nitrc-benzoylanino) -1 - [^ - (n-butylearb-

amoyl) benzoylamino [] anthraquinone red

105 ¹ i - (^ - methyl-betizoylarnir: o) -l- £ ¹ * - (n-butylcarb-

amoyl) -benzoylarr.inoJ-ar: thrachinone red

106 ^ - (iU.Methoxy-benzoylarnino) -! - ^ ¹ * - (n butylcarbamoyl) -benzoy] amino]] - anthrachir.on red

107 M - (^ - TrIf luormethyl-benzoylamino) -l- £ ² S- (n-butylcarbamoyl) -benzoylamino] -anthraquinone red

108 4- (5-chloro-2-cyano-benzoyla. ^ Ino) -l- £ ^ - (n-butylcarbamoylj-benzoylamino ^ -anthraquinone red

109 ^ -Acety] amino-1-f ¹ ^ - (n-butylcarbamoyl) -benzoylamino] -anthrachinone · red

110 !, ^ - Dibenzoylarnino-ll - ^ 'l-fn-butylcarbamoyl) -

benzoylamino "] - anthraquinone" red

111 ^ -Nitro-i-Cl-chloro-benzoylarrino) - ^ - (4-phenylcarbamoyl-benzoylamino) -anthraquinor. Red

112 5,8-dichloro- ¹ + - (H-chloro-benzoylatniino) -l- (M ~ phenylcarbamoyl-benzoylanino) -anthraquinone red

113 ^ -. (It-chloro-benzoylaminoJ-l- ^ io-inethoxy-benz- red thiazolyl- (2) -carbamoyl J-benzoylar.ilnoJ-anthrachlnon

Uli M- (4-chloro-benzoylamino) -l- [H- (2 ~ phenyl-benz = red triazolyl- (5) -carbamoyl) -benzoylanino] -

anthraquinone

₁₁₅ 4- (4-chloro-bei zoyla-nino) -l- (2-hydroxy-3-phenyla. Red carbamoyl-propionyl2. ^R nino) -ia-nthrachlnon

116 l »- (H-chloro-benzoylamino) -l- (9-phenylcarbamoyl- red octadecanoyl-amino) -anthraquinone

117 M - (^ - chloro-benzoylamino) -l- (2,5-dlfluoro- red Jl-phenylcarbamoyl-benzoylaminoJ-anthrachlnone

Le a 11 ^ 71 "" 109843/1395

BAD ORiGiNAL

dye

hue

1-Benzoylamino ~ 4- {phenylcarbamoyl-: formylamino) - ο rank antb.racb.inon

1-Benzoylamino-4- (3 ~ ph.enylcarbanioyl-propionyl-red amino) anthraquinone

1-Benzoylaniino-4- (7-ph.enylcarbamoyl-Höptanoyl- red anino) anthraquinone

4-Benzoylamino -! - (Ji-phenylcarbamoyl-naphthoyl-red (1) -amino) -anthraquinone

4-Benzoylamino -! - {i-phenylcarbamoyl-naphthoyl-red (1) -amino) -anthraquinone

^ -Benzoylamino-i-iS-pnenylcarbamoyl-furanoyl- red (2) -amino) -anthraquinone

4-Senzoylamino-i- (5-phenylcarbajnoyl-thiopheno-red yl ~ (2) - ««! no) -anthraquinone

4-Benzoylamino-i-io-phenylcarbamoyl-pyridinoyl-red (2) -anino) -anthraquinone

1-Benzoylamino-4- (4-phenylcarbainoyl-3-oxa red butyrylaaino) anthraquinone

1-Benzoylajnino-4- (4-phenylcarba »oyl-3-thla-red butyrylawino) anthraquinone

1-Benzoylamino-U- (4-phenylcarbamoyl-3-aza-red butyrylamino) anthraquinone

i-BenzoylaiBino-4 - (^ - phenylcarbamoyl-3-oxo-red butyrylaminoJ-anthraquinone

1-B * nzoylamino-4- (2-acetylamino-3-phenyl-red carbaeoyl-propionylamino) -anthraquinone 4-Benzoylamino-1- (2,5-dimethoxy-4-phenyl »red carbamoyl-benzoylaeino) anthraquinone % -B * nzoyXaraino-1- (2 _l 3.5 _f 6-tetrafluoro-4-phenyl-red carbamoyl-benzoylamino) -anthraquinone 4-Benzoylamino— 1 - [] 4 .- (U-phenylcarbamoyl red phenylazo) -benzoyla »ino ^ -anthraquinone Ji-Benzoylamino-i-J ^ -ilf-phenylcarbamoyl-red phenylazoxy) benzoylaminoJ-anthraquinone

Le A 11 571

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example

dye

hue

135

136 137 138 139

146

4-Benzoylainino-1 - j Ί-Γ4- {k · -phenylcarbamoylbiphenyl-C *) -azo) -phenyl-benzoylaeinojanthraquinone

Red

4-Benzoylamino-1-j ^ U- (4-phenylcarbaeoyl-benzyl) - red benzoylamino] anthraquinone

4-Benzoylainino-1 - [] * ♦ - (^ -phenylcarbaeioyl-phenyl-red hydraζtnο) -benzoylaminoj-anthraquinone

i-Benzoylainino-4- ^ ₍ 3 ~ ph- ^en yl ^car * ^{> anto} yJ ^L ~ ^acr Tl ° ylamino) -anthraquinone

1-Benzoylamino-4- (2-phenylcarbamoyl-3, U, 5,6-tetrahydro-benzoylamino) anthraquinone

i-Benzoylamino - ^ - iU-phenylcarbanioyl-hexahydrobenzoylamino) anthraquinone

^ -Benzoylajnino- 1- (3-nitro-4-phenylcarbamoylbenzoylaoiino ) anthraquinone

^ -Benzoylamino-1- (3-chloro-4-phenylcarbamoylbenzoylamino) anthraehinone

4-Benzoylamino-1- (2,3,5 _t ö-tetrachlor - ^ - phenyl- violet carbamoyl-benzoylaaiino) -5 · 8-dihydrite> xy-

anthraquinone

U-Methylamino-i - ^ - i ^ -sulfamoyl-phenylcarbamoyl) - blue benzoylaminoQ-anthraquinone

U-Cyclohexylamino-i - ^ - Cf-sulfamoyl-phenyl- blue carbamoyl) -benzoylaminojj-anthraquinone

blue

red red red red

phenylcarbanoyl) benzoylamino jantturaquinone

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Examples 1 * 17-1.5 ?:

According to Example 5, but using appropriate amounts of pein dough from the dyes indicated in the table instead of the pein dough from ^ - (iUCnlor-benzoylamino) -! - ^ - ^ - sulf araoyl-phenylcarbamoyl) -benzoylamino] -anthraquinone, one obtains real Coatings with the colors specified in the table:

Example dye ; hue

1 * 17 i | - (2-chloro-benzoylamino) -l- [3- (2-nitro-red

¹ l-carbamoyl-phenylcarbamoyl) -benzoylamineOj | - ' %

anthraquinone

^ - (J-chloro-benzoylaminoJ-l-p-CS-nitro-M- red carbamoyl-phenylcarbamoyl) -benzoyl amino] -anthraquinone

H-Benzoylamino-1- [ ^I »- ( ¹ -chlorophenylcarbamoyl) - red benzoylamino-anthraquinone

150 i) - (5-Trifluoromethyl-benzoylamino) -1- [ ¹ »- red (n-butylcarbamoyl) -benzoylamino ^ -anthraquinone

151 4 - (^ - Nitro-benzoylamino) -l- ( ¹ l-phenylcarbamoyl-red benzoylamino) -anthraquinone

Example ^ 6

According to Example 7, but using corresponding amounts of the dyes given in the table below, finely divided instead of ¹ I - (*! - ChlorobenzoylaminoJ-I - [^ - (2-chloro-phenyloarbamoyl) -benzoylamino] -anthraquinone , genuinely pigmented polyvinyl chloride is obtained with the color shades given in the table.

^{Le A 11} 571-37-109843/1395

Example dye ** shade

^ - (^ - chloro-benzoylaminoJ-l-f ^ -phenylcarb- red amoyl-benzoylamino) anthraquinone

155 H-fll-chloro-benzoylamincO-l - ^ - ^ - sulf- red amoyl-phenylcarbamoyl) -benzoylamino] -anthraquinone

156 ¹ i- (3-chloro-benzoylamino) -l- [ ¹ <- (3-chloro-red phenylcarbamoyl) -rbenzoylamino] -anthraquinone

157 4 - (^ - Chloro-benzoylamino) -l- [3- ( ¹ -ChIOr- red phenylcarbamoylj-benzoylamino ^ -anthraquinone

158 ¹ I- (3-Trifluoromethyl-benzoylamino) -l- ( ¹ I-red phenylcarbamoyl-benzoylaminoj-anthraquinone

159 ¹ l- (3-trifluoromethyl-benzoylamino) -l- [ ¹ <- red (M-chlorophenylcarbamoyli-benzoylamino]) - anthraquinone

160 ¹ * - ( ¹ l -nitro-benzoylamino) -l- [ ¹ l- (2-chloro-red phenylcarbamoylj-benzoylaminoj-anthraquinone

161 ¹ U ( ¹ I-Ni tro-benzoylamino) -l- (^ -phenyl = red carbamoyl-benzoylaminoj-anthraquinone

Example l62-171t

If a pigmented paper is produced according to Example 17 using the dyes indicated in the table, or a paper is printed with a printing ink which contains a fine paste produced according to Example 5 using the dyes indicated below, as well as water-soluble or saponifiable binders, and treats the paper pigmented or printed in this way according to Example 18, real laminate papers with the specified color shades are obtained:

Le A 11 571 - 38 -

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example

dye

hue

162 163 1 6k 165 166 167 168

172

4- (4-Chloro-benzoylamino) -1 ~ ^ -methylcarbamoyl · benzoylamino ) anthraquinone

k- (4-Chloro-benzoylamino) -1- £ 4- {k -nitro phenylcarbamoyl ) -benzoylamino ^ -anthraquinone

U-Benzoylamino-1 ~ \ J * - (n-butyl-carbamoyl ) benzoylaminol-anthraquinone

^ -Benzoylamino-i-i ^ -phenylcarbamoylbenzoylamino) anthraquinone

it-Benzoylamino-1 - ^ k- (Z-chloro-phenylcarbamoyl) -benzoylaminol-anthraquinone

4 -Benzoylamino-1- \ _ h- (4-nitro-phenylcarbamoyl) -benzoylamino] -anthraquinone

- (3-Trifluoromethyl-benzoylamino) -1- (4-butylcarbamoyl-benzoylamino) anthraquinone

k- (4-Ni tro-benzoylamino) -1 - \ _ k- (4-chlorophenylcarbamoyl) -benzoylaminoJ-anthraquinone

2-bromo-1 - £ * ♦ - (^ - chlorophenylcarbamoyl) benzoylamino]] - ^ - (U-methyl-benzenesulf amido) anthraquinone

red-violet red bordo red red red red red

T- ,, χ

Le η 11 571

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Claims (8)

Claims; Dyes of the formula where Y is an optionally substituted hydrocarbon, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl radical, R is the grouping -CO-B-CO-NH-E, where B is a single bond or a saturated one which is optionally further substituted or interrupted by heteroatoms or unsaturated alkylene radical, an optionally further substituted mononuclear or polynuclear arylene radical or heteroarylene radical and E denotes an optionally substituted saturated or unsaturated alkyl or cycloalkyl radical, an optionally further substituted heteroaryl radical or an optionally one or more halogen atoms, nitro groups, alkyl groups with 1-12 carbon atoms, cycloalkyl groups, fused cyclohexyl or benzene rings, trifluoromethyl groups, arylamino groups, hydroxyl groups, alkoxy groups with 1-3 carbon atoms, phenoxy groups, alkylsulfonyl groups, arylsulfonyl groups, alkylcarbory represents l groups, arylcarbonyl groups, carboxyl groups, carboxylic acid ester groups, unsubstituted carbonamide groups, sulfamoyl groups, alkylsulfonylamino groups, arylsulfonylamino groups, aryl radicals containing phenylazo or phenylazoxy groups, and rings C and D may optionally have further substituents. - 40 - Le λ 11 571 109843/1395 «Μ 2. Dyes of the formula NH-CO-B'-CO-NH-E
ι where Y is an optionally substituted hydrocarbon, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl radical, R is the grouping -CO-B-CO-NH-E, where B is a single bond or a saturated one which is optionally further substituted or interrupted by heteroatoms or unsaturated alkylene radical, an optionally further substituted mononuclear or polynuclear arylene radical or heteroarylene radical and E denotes an optionally substituted saturated or unsaturated alkyl or cycloalkyl radical, an optionally further substituted heteroaryl radical or an optionally one or more halogen atoms, nitro groups, alkyl group with 1-12 carbon atoms, cyoloalkyl groups, fused cyclohexyl or benzene rings, trifluoro- amino groups, hydroxyl groups, alkoxy groups with 1-5 carbon atoms, phenoxy groups, alkylsulfonyl groups, arylsulfonyl groups, alkylcar carbonyl groups, arylcarbonyl groups, carboxyl groups, carboxylic acid ester groups, unsubstituted carbonamide groups, sulfamoyl groups, alkylsulfonylamino groups, arylsulfonylamino groups, aryl radicals containing phenylazo or phenylazoxy groups, and B ^{1 represents} an optionally substituted arylene radical and the rings C and D can optionally have further substituents. Le A 11 571 - 41 - 109843/1395 3) Use of dyes of claim 1 as pigments. 4) Use of dyes of claim 1 for pigmenting of lacquers and paints, for coloring polymers, Polycondensates and polyaddition products as well as for coloring printing inks and printing inks. 5) Use of dyes of claim 1 for mass coloring of vulcanizates, polyvinyl chloride, polyacrylonitrile, polyesters, Polypropylene, polyethylene and cellulose derivatives. 6) Polymers, polycondensates, polyaddition products, printing inks, Printing inks, varnishes and paints pigmented or mass-colored with the dyes of claim 1. 7) Process for the preparation of dyes of the formula 0 NH-R Il I Il I 0 NH-Y wherein Y is an optionally substituted hydrocarbon, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or Arylsulfonyl radical, R stands for the grouping -CO-B-CO-NH-E, in which B is a single bond or an optionally further substituted or interrupted by heteroatoms saturated or unsaturated alkylene radical, an optionally further substituted one or polynuclear arylene radical or heteroarylene radical and E is an optionally substituted saturated or unsaturated one which is optionally interrupted by heteroatoms Alkyl or cycloalkyl radical, an optionally further substituted heteroaryl radical or an optionally one one or more halogen atoms. Nitro groups, alkyl groups ■ with 1-12 carbon atoms !!, cycloalkyl groups, ad- j. _P 109843/1395 Le A 11 571 - 42 - BATH ORIGINAL Densed cyclohexyl or benzene rings, trifluorine thy 1 groups, ary! amino groups, hydroxyl groups, alkoxy groups with 1-5 carbon atoms, phenoxy groups, alkylsulfonyl groups, arylsulfonyl groups, alkylcarbonyl groups, arylcarbonyl groups, carboxyl groups, carboxylic acid ester groups, unsubstituted carboxylic acid sulfonyl groups, aamoylsulfonyl groups, ! represents amino groups, arylsulfonylamino groups, aryl radical containing phenylazo or phenylazoxy groups, and rings C and D may optionally have further substituents, characterized in that .nnthraquinone derivatives of the formula 0 NH ₉ H I <- ti I 0 Nn-Y wherein Y has the abovementioned meaning and the rings C and D optionally have further substituents, with at least one mole of a reactive derivative of a dicarboxylic acid the formula HO-CO-B-CO-OH where B has the meaning given above, reacted and then with at least one mole of an amine of the formula H ₂ NE viorin E has the meaning given above, to react. L. A 11 571 - * ³ - 109843/1395 8) Process for the preparation of dyes of the formula where Y is an optionally substituted hydrocarbon, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl radical, R is the grouping -CO-B-CO-NH-E, where B is a single bond or a saturated one which is optionally further substituted or interrupted by heteroatoms or unsaturated alkylene radical, an optionally further substituted mononuclear or polynuclear arylene radical or heteroarylene radical and E denotes an optionally substituted saturated or unsaturated alkyl or cycloalkyl radical, an optionally further substituted heteroaryl radical or an optionally one or more halogen atoms, nitro groups, alkyl group, optionally interrupted by heteroatoms -12 carbon atoms, cycloalkyl groups, fused cyclohexyl or benzene rings, trifluonethyl groups, aryamino groups, hydroxyl groups, alkoxy groups with 1-3 carbon atoms, phenoxy groups, alkylsulfonyl groups, arylsulfonyl groups, alkylcarbony represents oil groups, arylcarbonyl groups, carboxyl groups, carboxylic acid ester groups, unsubstituted carbonamide groups, sulfamoyl groups, alkylsulfonylamino groups, arylsulfonylamino groups, aryl radicals containing phenylazo or phenylazoxy groups, and rings C and D may optionally have further substituents, Le A 11 571 108843M39S characterized in that one anthraquinone derivatives of the formula Il I 0 NH-Y wherein Y has the meaning given above and the rings G and D optionally have further substituents, with at least one mole of an N-substituted dicarboxylic acid monoamide the formula HOOC-B-CO-NH-E wherein B and E have the abovementioned meaning, is reacted. L · · λ 11 571 _f 109843/1395