MXPA98003569A - Compositions of diceto pirrolo pirrol novedo - Google Patents

Abstract

Compositions of substance, which comprise at least three diketopyrrolopyrroles of the formulas: (See Formulas) wherein: A is a group (See Formula), and B is a group (See Formula) R1 is an alkyl of 1 to 5 carbon atoms , alkoxy of 1 to 6 carbon atoms, halogen, or phenyl, R2 is a COX group, wherein: X is NR4R5 or a heterocyclic radical containing at least two N atoms, one of whose N atoms forms an amide with the carbonyl group , R3 is hydrogen, halogen, or alkyl of 1 to 6 carbon atoms. The meaning of R4 and R5 is as defined in claim 1. The mixture of this substance composition with diketopyrrolopyrrole pigments improves the rheological behavior of the latter, as well as the brightness of the placements produced therewith, to an unexpected degree

Description

COMPOSITIONS OF DICETOPIRROLOPIRROL NOVEDOSAS # The present invention relates to compositions of substance consisting of diketopyrrolopyrroles substituted by carbonamide groups, and their use to improve the brightness and rheology of diketopyrrolopyrrole pigments. Japanese Patent Number JP-A 91-26767 describes diketopyrrolopyrroles having substituents containing from 1 to 4 amino groups, including among many others, also the compound of the formula: and its use as dispersants for pigments. These compounds provide the pigments with a good rheological behavior, and the colorations obtained therewith with a beautiful luster. It has now been discovered that these properties, in a very surprising way, can be improved by the use of substance compositions consisting of three different diketodiphenyl pyrrolopyrroles, 2 of which one in an asymmetric configuration and the other in a symmetric configuration one or two carbonamide groups in the p position, or preferably in the m position of the phenyl. According to the above, this invention relates to compositions of substance, comprising at least 3 diketopyrrolopyrroles of the formulas: where : A is a group B is a group R1 is an alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halogen, or phenyl, R2 is a COX group, wherein: • X is NR4R5 or a heterocyclic radical containing at least two N atoms, one of whose N atoms forms an amide with the carbonyl group, R 3 is hydrogen, halogen, or alkyl of 1 to 6 carbon atoms, R 4 is hydrogen, a group - (CH 2 ) m-CH3, or R5, and G can be a direct bond, -CH2-, CH (CH3) -, -C (CH3) 2- -CH = N-, -N = N-, -O-, -S-, -SO-, -S02 -, or -NR9-, Rs is alkyl of 1 to 6 carbon atoms, R7 and Ra are each independently of the other, hydrogen, halogen, alkyl of 1 to 6 carbon atoms, Rg is hydrogen or methyl, m is zero or a number from 1 to 17, and n is a number from 2 to 6. k Any substituents defined as alkyl of 1 to 6 carbon atoms are alkyl of 1 to 6 unbranched carbon atoms, for example methyl, ethyl, normal propyl, normal butyl, normal pentyl, or normal hexyl, or alkyl of 5 to 6 branched carbon atoms, for example isopropyl, normal butyl, secondary butyl, tertiary butyl, secondary amyl, or tertiary amyl. Where R? is defined as alkoxy of 1 to 6 atoms of ^^ carbon and thioalkyl of 1 to 6 carbon atoms, alkyl has The same meaning as that given above for alkyl of 1 to 6 carbon atoms. R1, R3, R7 and R8, defined as halogen, are typically iodine, bromine, or preferably chlorine. X, defined as a heterocyclic radical containing at least two N atoms is, for example, a heterocycle of the formula: B is preferably a group Particularly interesting substance compositions according to the above definitions are those where: R- is methyl, alkyl of 1 to 6 carbon atoms branched, phenyl, halogen, R2 is C0NR5R6 or CON N-R6, R3 and R4 are hydrogen, R5 is a group - (CH2) n- (CH3) 2 or R7 is hydrogen or methyl, and n is a number from 2 to 6.

Preferred substance compositions of the above definition are those wherein: R1 is methyl, tertiary butyl, phenyl, or chloro, R5 is a group - (CH2) n-N (CH3) 2, and n is 2 or 3.

The substance compositions of this invention are prepared in analogy to the commonly known method of preparation for diketopyrrolopyrroles, as described in U.S. Patent No. 4,579,949, ie, by on-site synthesis, wherein, by example, 1 mole of a disuccinate is reacted with two moles of a mixture consisting of at least two nitriles of the formulas: (IV) and (V) (VI) wherein R1, R2, and R3 have the meanings given above. The two nitriles of formulas IV and V or VI are conveniently used in a molar ratio of 1: 4 to 4: 1, one to the other. The nitriles of formulas IV, V, and VI are known compounds. Any of them that is still novel, can be prepared in analogy to commonly known processes. As already mentioned, it has been found that mixing a smaller proportion of a novel substance composition of the above definition with a diketopyrrolopyrrole pigment results in a very surprising improvement of the latter's rheological behavior, and that of the brightness of the colorations obtained with it. In particular, the rheological behavior of transparent diketopyrrolopyrrole pigments is improved. In addition, the novel substance compositions do not change the hue of the diketopyrrolopyrrole pigment, or at most only to a very minor degree.

Furthermore, it has been found that, if diketopyrrolopyrroles of formula II are mixed, which have the definitions and preferred meanings given above, by themselves, they are a diketopyrrole pigment, an unexpected improvement of rheological behavior and brightness is also effected. . The diketopyrrolopyrols of the formula II can be prepared, inter alia, by the method described in U.S. Patent No. US 4,778,899. Accordingly, this invention also relates to pigment compositions, which comprise: a) from 80 to 99.9 weight percent of at least one 1,4-diketopyrrolo pigment [3, -c] irol, in particular one of the formula: wherein R10, R ?, R12, and R13 are each independently of the others, hydrogen, Cl, Br, CH3, OCH3, C02R6 C (CH3) 3, CN or phenyl, and b) from 0.1 to 20 percent in weight of a composition of substance comprising three diketopyrrolopyrroles of formulas I, II, and III, or a diketopyrrolopyrrole of formula II of the above definition. Component b) is preferably a composition comprising 3 diketopyrrolopyrroles of formulas I, II, and III of the above definition. The preferred 1,4-diketopyrrolo [3, 4-c] pyrroles of formula VII are those wherein R 10 and R 12 are each independently of the other, Cl, CH 3, C (CH 3) 3, CN, or phenyl, and R 1 : L and R13 are hydrogen. Preferred pigment compositions are those comprising 1,4-diketopyrrolo [3, 4-c] pyrroles of formula VII, and a substance composition comprising three diketopyrrolopyrroles of formulas I, II, and II, wherein: R11 and R13 are hydrogen, and R10 'R12 R? they are identical, and are preferably ethyl, tertiary butyl, tertiary amyl, phenyl, or chloro. The 1,4-diketopyrrolopyrroles of the formula VII are known compounds. The two components a) and b) are mixed by any commonly known method. Component b) can be mixed with component a), for example, as a "JP wet press cake, or in the form of a powder during the synthesis, recrystallization, or filtration of said component a). and b) they can also be mixed by vigorous mixing or milling, or they can be added to the high molecular weight organic material to be colored and mixed during the dispersion process.The novel pigment compositions can be used as pigments for coloring a high molecular weight organic material 10 High molecular weight organic materials that can be colored or pigmented with novel pigment compositions are, for example, ethers and cellulose esters, such as ethyl cellulose, nitrocellulose, cellulose, cellulose butyrate, natural resins or resins synthetics, such as polymerization or condensation resins, for example aminoplasts, in particular resins # of urea / formaldehyde and melamine / formaldehyde, alkyl resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polytetrafluoroethylene, polyamides, polyurethanes, polyesters, polyetherketones, polyphenylene oxides, rubber, casein, silicone and silicone resins, alone or in mixtures. The aforementioned high molecular weight organic compounds can be obtained alone or in mixtures as plastic compositions, fusions, or in the form of centrifuged solutions, paints, coatings, or inks for printing. Depending on the predicted end use, it is convenient to use the novel pigment compositions as matizers, or in the form of preparations. The novel pigment compositions 5 can be used in an amount of 0.01 to 30 weight percent, preferably 0.1 to 10 weight percent, based on the high molecular weight material to be pigmented. ^ To pigment paints and inks for printing, the High molecular weight organic materials and novel pigment compositions, together with optional additives such as fillers, other pigments, slicatives, or plasticizers, are finely dispersed or dissolved in a common organic solvent or a mixture of solvents. He The process can be such that the individual components by themselves, or also several together, are dispersed or dissolved, and subsequently all the components are mixed. The colorations thus obtained, for example, in plastic materials, fibers, paints, or impressions, are distinguished by good firm properties all around, good dispersibility, good firmness to re-coating, migration, heat, light, and weathering, as well as a low viscosity and good gloss . Compared with unmodified base pigments, the novel pigment compositions additionally have better properties with respect to their performance in use, such as better rheology and storage stability, less separation effects such as Flood of the pigment when used together with, for example, white pigments, and less tendency to flocculate. Due to the good rheological properties of these compositions, it is also possible to prepare coatings and ^ a paintings of a high concentration (denominated of high charge). The high brightness is additionally obtained at the same time. The mixing of the novel pigment compositions does not change the hue, or only to a very minor degree. The novel pigment compositions, therefore, are preferably suitable for coloring printing inks and paintings, in particular for metallic effect finishes. The invention is illustrated by the following examples.

Example 1: A sulfonation flask is charged under nitrogen with 9.2 grams of sodium in a mixture consisting of 50 milliliters of dry tertiary amyl alcohol, and 140 milliliters of dry xylene, and this mixture is stirred at 150 ° C until the sodium reacts completely. Then 18.5 grams of 3-cyano (3-dimethylaminopropyl) benzamide and 12.74 grams of tertiary butyl-benzonitrile are added. Subsequently, A solution of 23.95 grams of tertiary dibutyl succinate in 60 milliliters of xylene is slowly added dropwise at 120 ° C. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 50 ° C, and added to a mixture consisting of 670 milliliters of water and 24.6 grams of 5-acetic acid. The sulfonation flask is flooded with 160 milliliters of methanol, and then the mixture is distilled with steam, stirred for 18 hours at room temperature, and filtered. The residue is first washed with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then dried overnight in a vacuum drying oven at 80 ° C. Yield: 24.75 grams (65 percent) of an orange powder.

Analysis: C H N 15 found: 72.07 7.12 8.75 calculated: 72.00 7.18 8.69 # Example 2: A sulfonation flask is charged under nitrogen with 20 1.15 grams of sodium in a mixture consisting of 7 milliliters of dry tertiary amyl alcohol, and 13 milliliters of dry xylene, and this mixture is stirred at 150 ° C, until the sodium reacts completely. Then the resulting solution is charged with 2.31 grams of 3-cyano- (3-dimethylaminopropyl) benzamide and 1.37 grams of 4-chlorobenzonitrile at 90 ° C. Subsequently, a solution of 3.07 grams of tertiary dibutyl succinate in 10 milliliters of xylene is slowly added dropwise at 120 ° C. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 60 ° C, and added to a mixture consisting of 85 milliliters of water and 3.06 grams of acetic acid. The sulfonation flask is flooded with 25 milliliters of methanol, and then the mixture is distilled with steam, stirred for 18 hours at room temperature, and filtered. * I The residue is washed first with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then dried in a vacuum drying oven at 80 ° C, giving 2.32 grams of a red powder.

Analysis: C H N Cl 15 found: 61.69 4.33 9.50 11.98% calculated: 63.93 5.14 12.42 7.86% On 3; A sulfonation flask is charged under nitrogen with 20 1.15 grams of sodium in a mixture consisting of 7 milliliters of dry tertiary amyl alcohol, and 13 milliliters of dry xylene, and this mixture is stirred at 150 ° C, until the sodium reacts completely . The resulting solution is then charged with 2.31 grams of 3-cyano- (3-dimethylaminopropyl) benzamide, and 1.79 grams of 3-biphenyl nitrile, at 90 ° C.

Subsequently, a solution of 3.07 grams of tertiary dibutyl succinate in 10 milliliters of xylene is slowly added dropwise at 120 ° C. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 60 ° C, and added to a mixture consisting of 85 milliliters of water and 3.06 grams of acetic acid. The sulfonation flask is flooded with 25 milliliters of methanol, and the mixture is then distilled with steam, and stirred for 18 hours at room temperature, and filtered. The residue is washed first with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then dried in a vacuum drying oven at 80 ° C, giving 2.5 grams of a red powder.

Analysis: C H N found: 74.13 5.36 8.47% calculated: 73.15 5.73 11.37% Example 4: A sulfonation flask is charged under nitrogen with 1. 15 grams of sodium in a mixture consisting of 7 milliliters of dry tertiary amyl alcohol and 13 milliliters of dry xylene, and this mixture is stirred at 150 ° C until the sodium reacts completely. Then the resulting solution is charged with 2.31 grams of 3-cyano- (3-dimethylaminopropyl) benzamide and 1.17 grams of 4-toluonitrile at 90 ° C. Subsequently, a solution of 3.07 grams of tertiary dibutyl succinate in 10 milliliters of xylene is slowly added dropwise at 120 ° C. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 60 ° C, and added to a mixture consisting of 85 milliliters of water and 3.06 grams of acetic acid. The sulfonation flask is flooded with 25 milliliters of methanol, and the mixture is distilled with steam, stirred for 18 hours at room temperature, and filtered. He # 10 residue is washed first with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then dried in a vacuum drying oven at 80 ° C, giving 1.23 grams of a red powder.

Analysis: c H N found: 67.43 6.08 10.49% calculated: 69.75 6.09 13.01% In 5; (as Example 1) A sulfonation flask is charged under nitrogen with 1.15 grams of sodium in a mixture consisting of 7 milliliters of dry tertiary amyl alcohol and 13 milliliters of dry xylene, and this mixture is stirred at 150 ° C until Sodium reacts completely. The resulting solution is loaded then with 2.31 grams of 3-cyano- (3-dimethylaminopropyl) benzamide and 1.33 grams of 4-methoxybenzonitrile at 90 ° C.

Subsequently, a solution of 3.07 grams of tertiary dibutyl succinate in 10 milliliters of xylene is slowly added dropwise at 120 ° C. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 60 ° C, and added to a mixture consisting of 85 milliliters of water and 3.06 grams of acetic acid. The sulfonation flask is flooded with 25 milliliters of methanol, and the mixture is then distilled with steam, stirred for 18 hours at room temperature, and filtered. The residue is washed first with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then dried in a vacuum drying oven at 80 ° C, giving 0.71 grams of a red powder.

Analysis: c H N found: 65. 12 5. 61 8. 83% calculated .: 67. 25 5. 87 12. 55% Example 6; A sulfonation flask is charged under nitrogen with milliliters of tertiary amyl alcohol. After adding 0. 76 grams of sodium, the mixture is heated to 92-102 ° C. With vigorous stirring, molten sodium is maintained overnight at 100-107 ° C. The resulting solution is charged at 100 ° C with 2.77 grams of 3-cyano- (3-dimethylaminopropyl) benzamide, and then, for 2 hours, with 3.16 grams of pyrrolinone of the formula (X): in portions [prepared in accordance with Ann. 260, page 137 (1980)]. The reaction mixture is stirred for 3 hours at reflux, and then cooled to 60 ° C, and added to a mixture consisting of 25 milliliters of water and 25 milliliters of methanol. This mixture is stirred for 4 hours at 70 ° C, and then cooled to room temperature and filtered. The residue is washed with water and methanol, until the filtrate is colorless, and then dried in a vacuum drying oven at 80 ° C, giving 1.1 grams of an orange powder.

Analysis: c H N found: 70. 54 7. 01 11. 82 calculated: 71. 16 6. 82 11. 86 Example 7; A sulfonation flask is charged under nitrogen with 4.60 grams of sodium in a mixture consisting of 25 milliliters of dry tertiary amyl alcohol and 90 milliliters of dry xylene, and this mixture is stirred at 150 ° C, until the sodium reacts completely. Then the resulting solution is charged with 9.25 grams of 3-cyano- (3-dimethylaminopropyl) benzamide and 4.73 grams of 4-toluobenzonitrile at 90 ° C. Subsequently, a solution of 11.98 grams of tertiary dibutyl succinate in 30 [mu] milliliters of xylene at 120 [deg.] C. is slowly added dropwise. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 50 ° C, and added to a mixture consisting of 325 milliliters of water and 12.31 grams of acetic acid. The sulfonation flask is flooded with 70 milliliters of methanol, and then the mixture is distilled with steam, stirred for 18 hours at room temperature. room temperature, and filtered. The residue is first washed with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then dried in a vacuum drying oven at 80 ° C, giving 13.4 grams of a red powder. 20 Analysis: C H N found: 69.59 6.44 11.01% calculated: 69.75 6.09 13.01% # Example 8: A sulfonation flask is charged under nitrogen with 3.68 grams of sodium in a mixture consisting of 20 milliliters of dry tertiary amyl alcohol and 56 milliliters of dry xylene, and this mixture is stirred at 150 ° C, until Sodium reacts completely. The resulting solution is then charged with 7.40 grams of 3-cyano- (3-dimethylaminopropyl) benzamide and 4.10 grams of isophthalic acid dinitrile at 90 ° C. Subsequently, it is added slowly drip a solution of 9.58 grams of tertiary dibutyl succinate in 24 milliliters of xylene at 120 ° C. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 50 ° C, and added to a mixture consisting of 270 milliliters of water and 9.85 grams of acetic acid. The flask of sulfonation is flooded with 60 milliliters of methanol, and then the mixture is distilled with steam, stirred for 18 hours at room temperature, and filtered. The residue is washed first with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then is dried in a vacuum drying oven at 80 ° C, giving 12.2 grams of a red powder.

Analysis: c H N found: 68.60 5.78 13.45% 25 calculated: 68.01 5.25 15.86% Jff Ei emplo 9; A sulfonation flask is charged under nitrogen with 4.60 grams of sodium in a mixture consisting of 20 milliliters of dry tertiary amyl alcohol and 90 milliliters of dry xylene, and this mixture is stirred at 150 ° C, until the sodium reacts completely. Then the resulting solution is charged with 7.40 grams of 3-cyano- (3-dimethylaminopropyl) benzamide and 5.50 grams of 3,4-dichlorobenzonitrile at 90 ° C. Subsequently, a solution is added slowly by dripping of 11.98 grams of tertiary dibutyl succinate in 30 milliliters of xylene, at 120 ° C. The reaction mixture is stirred for 2 hours at reflux, and then cooled to 50 ° C, and added to a mixture consisting of 325 milliliters of water and 12.31 grams of acetic acid. The sulfonation flask was is flooded with 70 milliliters of methanol, and the mixture is then distilled with steam, stirred for 18 hours at room temperature, and filtered. The residue is first washed with a large amount of water, then with a small amount of a water / methanol mixture, 1: 1, and then dried in a vacuum drying oven at 80 ° C, giving 10.5 grams of a red powder.

Analysis: c H N found 58. 88 4. 59 8. 37% 25 calculated: 59. 39 4. 57 11. Example 10; Preparation of a pigment composition 45.5 grams of a press cake (34.1 percent) of a pigment mixture consisting of 1,4-diketo-3,6-diphenylpyrrolo [3,4-c] pyrrole, and 1, 4- Diceto-3-phenyl-6- (4-5-chlorophenyl) -pyrrolo [3,4-c) pyrrole, and 1,4-diketo-3,6-di (4-chlorophenyl) -pyrrole [3, 4-c] ] pyrrole, prepared according to Example 1, US Pat. No. 5,476,949, are stirred in 450 milliliters of water for 1 hour at room temperature, and then allowed to stand for 18 hours (= suspension 1). At the same time, 0.989 grams of the substance of Example 1 is stirred in 30 milliliters of methanol for 1 hour at room temperature, and this mixture is charged with 30 milliliters of water, and also allowed to stand for 18 hours (= suspension) 2) .

Both suspensions are stirred individually for another hour at room temperature. Subsequently, suspension 2 * Pour into suspension 1. The residue is rinsed with some water, and thoroughly mixed for 2 minutes with an Ultraturrax at 13.5000 at 20,500 rpm. The foaming is counteracted by the addition of some 1,6-hexanediol. The suspension is stirred for 4 hours at room temperature, filtered, washed with water, and dried in a vacuum drying oven at 80 ° C, giving 16.1 grams of an orange-red powder.

Example 11: The procedure of Example 10 is repeated, but jf replacing the pigment mixture of Example 10 with 36.3 grams of a press cake (2.7 percent) of 1,4-diketo-3, 6-di (4- biphenyl) irritated [3, 4-c] irrol, prepared according to Example 19, US Pat. No. 5,579,949, giving 16.0 grams of a dark red substance.

Example 12; The procedure of Example 10 is repeated, but replacing the pigment mixture of Example 10 with 50.1 grams of a press cake (30.9 percent) of 1,4-diketo-3,6-di (4-chlorophenyl) pyrrolo [3, 4-c] pyrrole, prepared according to Example 6, Patent of the United States of America Number 4,579,949, giving 16.5 grams of a red substance. Example 13; Preparation of a composition comprising a * high molecular weight organic material and pigment mixtures of Example 10: .0 grams of the pigment mixture of Example 10, 200 grams of glass granules (0 = 2 millimeters), 28.5 grams of CAB solution consist of: 41.0 grams of cellulose acetobutyrate RCAB 531.1, 20 percent in butanol / xylene, 2: 1 (Eastman Chem.), 25 1.5 grams of zirconium octoate, 18.5 grams of RSOLVESSO 150 (ESSO) 21.5 grams of butyl acetate, and 17.5 grams of xylene, 38.0 grams of RDYNAPOL H700 polyester resin (Dynamit Nobel), and 28.5 grams of MAPRENAL MF650 melamine resin (Hoechst), are dispersed together in a disperser for 360 minutes. The flow behavior of the paint thus obtained is determined using a Mettler viscometer RM 180 (25 ° C). '^? 10 The paint is distinguished by excellent rheological properties.

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Claims (10)

1. A composition of substantial, which comprises at least three diketopyrrolopyrroles of the formulas: where : 15 A is a group B is a group 20 R? is an alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halogen, or phenyl, R2 is a group COX, wherein: X is NR4R5 or a heterocyclic radical which contains at least two N atoms, one of whose N atoms forms an amide with the carbonyl group, R3 is hydrogen, halogen, or alkyl of 1 to 6 carbon atoms, R4 is hydrogen, a group - (CH2) m-CH3, or R5, and 15 G can be a direct bond, -CH2-, CH (CH3) -, -C (CH3) 2- -CH = N-, -N = N-, -O-, -S-, -SO-, - S02-, or -NRg-, F Rg is alkyl of 1 to 6 carbon atoms, R7 and R8 are each independently of the other, hydrogen, halogen, alkyl of 1 to 6 carbon atoms, Rg is hydrogen or methyl, m is zero or a number of 1 to 17, and n is a number from 2 to 6.

2. A composition of substance according to 25 claim 3, wherein: R-L is methyl, tertiary butyl, tertiary amyl, phenyl or chloro, R3 and R4 are hydrogen, R5 is a group - (CH2) n-N (CH3) 2, and n is 2 or 3.

3. A pigment composition, which comprises: a) from 80 to 99.9 weight percent of at least one 1,4-diketopyrrolo [3, 4-c] pyrrole pigment, and b) from 0.1 to 20 weight percent of a composition of substance comprising three diketopyrrolopyrroles of formulas I, II, and III according to claim 1, or a diketopyrrolopyrrole of formula II.

4. A pigment composition according to claim 3, wherein component b) is from 0.1 to 20 weight percent of a substance composition comprising three diketopyrrolopyrroles of formulas I, II, and III in accordance with claim 1.

A pigment composition according to claim 3, wherein a) comprises a 1,4-diketopyrrolo [3,4-c] pyrrole pigment of the formula: wherein R10, Rn, Ri2 'and Ri3 are each independently f of the others, hydrogen, Cl, Br, CH3, 0CH3, C (CH3) 3, CN or phenyl.

6. A pigment composition according to claim 3, which comprises 1,4-diketopyrrolo [3, 4- c] pyrroles of formula VII, and a substance composition comprising three diketopyrrolopyrroles of formulas I, II. , and II, where: R ?? and Ri3 are hydrogen, and R10, R12 and R-L are identical.

7. A pigment composition according to claim 6, wherein: R10 'Ri2 and R? they are methyl, tertiary butyl, tertiary amyl, phenyl or chloro.

8. A composition, which comprises a high molecular weight organic material, and a pigment composition 25 according to claim 3.

9. A process for coloring a high molecular weight organic material, which material comprises a tintorically effective amount of a pigment composition according to claim 3.

10. A high molecular weight organic material according to the material claim 9, which is a painting or ink for printing. # F • SUMMARY Compositions of substance, which comprise at least three diketopyrrolopyrroles of the formulas: O O O NH NH NH NH NH NH and O O B O B (0 (II) (III) where: # 10 "-L is an alkyl of 1 to 6 carbon atoms, alkoxy F of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halogen, or phenyl, R2 is a COX group, wherein: X is NR4R5 or a heterocyclic radical containing at least two N atoms, one of which N atoms form an amide with the carbonyl group, R3 is hydrogen, halogen, or alkyl of 1 to 6 carbon atoms. The meaning of R4 and R5 is as defined in claim 1. The mixture of this substance composition with diketopyrrolopyrrole pigments improves the rheological behavior of the latter, as well as the brightness of the colorations produced therewith, to a degree unexpected. 10 ^ W