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US 8,883,889 B2Granted
Pigment compositions comprising pyrrolo[3,4-c]pyrroles
AssigneeBASF SE
InventorsVincent Ruffieux, Florence Modoux
Life of this patent
Estimating the term…
Abstract
The present invention relates to a process for the direct preparation of pyrrolo[3,4-c]pyrroles (DPPs) of the formula pigment compositions containing them and their use for coloring high molecular weight organic materials, such as plastics and paints. The obtained DPPs of the formula I possess a higher color strength, a higher chroma, a purer shade and a higher opacity versus corresponding commercially available DPPs.
Claims10
A pigment composition comprising:
- a) a 1,4-diketopyrrolo[3,4-c]pyrrole of the formula (I)
- wherein
- R1 and R2 independently of each other are
- R31, R32, and R33 independently of one another are hydrogen, carbamoyl, C2-18-alkylcarbamoyl, C2-18-alkoxycarborlyl, C2-18-alkanoylamino, halogen, C1-C24alkyl, C1-C6alkoxy, C1-C18alkylthio, C1-C18alkylamino, di(C1-C18alkyl)amino, —CN, —NO2, phenyl, trifluoromethyl, C5-C6cycloalkyl, —C═N—(C1-C24alkyl),
- imidazolyl, pyrazolyl, triazolyl, piperazinyl, pyrrolyl, oxazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, morpholinyl, piperidinyl, or pyrrolidinyl,
- T2 is —C(O)—NH—, —C(O)—O—, —NH—C(O)—, —CH2—, —CH(CH3)—, —C(CH3)2—, —CH═N—, —N═N—, —O—, —S—, —SO—, —SO2—, or —NR38—,
- R34 and R35 independently of one another are hydrogen, halogen, C1-6-alkyl, C1-6-alkoxy, or —CN,
- R36 and R37 independently of one another are hydrogen, halogen, or C1-6-alkyl, and
- R38 is hydrogen or C1-C6-alkyl;
- and
- b) from 0.5 to 4 weight % based on the weight of the 1,4-diketopyrrolo[3,4-c]pyrrole of formula (I) of a compound of formula (V)
- wherein
- X is O, S, or NR14, wherein R14 is linear or branched C1-10-alkyl, C7-10-aralkyl, or C6-10-aryl;
- R12 and R13 are independently of each other hydrogen, linear or branched C1-10-alkyl, linear or branched C1-10-alkoxy, linear or branched C1-10-thioalkyl, C5-10-cycloalkyl, C6-10-aryloxy, C6-10-arylthio, C7-10-aralkyloxy, C7-10-aralkylthio, halogen, CONR5R6, C(O)OR7, or SO2R9;
- R5 and R6 are hydrogen, linear or branched C1-10-alkyl, C5-10-cycloalkyl, or C6-10-aryl,
- R7 is hydrogen, linear or branched C1-10-alkyl, C5-10-cycloalkyl, C7-10-aralkyl, or C6-10-aryl, and
- R9 is hydrogen, linear or branched C1-10-alkyl, C5-10-cycloalkyl, C7-10-aralkyl, C6-10-aryl, or NR10R11, wherein R10 and R11 are hydrogen, linear or branched C1-10-alkyl, C7-10-aralkyl, or C6-10-aryl.
14 more elements
A pigment composition comprising:
- a) a 1,4-diketopyrrolo[3,4-c]pyrrole of the formula (I)
- wherein
- R1 and R2 are independently of each other a group of formula (Ib)
- wherein R31 and R32 independently of one another are hydrogen, methyl, tert-butyl, chlorine, bromine, CN, or phenyl;
- and
- b) from 0.5 to 4 weight % based on the weight of the 1,4-diketopyrrolo[3,4-c]pyrrole of formula (I) of a compound of formula (VI)
- wherein R15 is hydrogen, 4-phenyl, 3- or 4-chloro, 3- or 4-methyl, or 4-tert-butyl;
- and R16 is o-, m- or p-C1-10-alkoxy, or o- or m-chloro, wherein R15 and R16 are different from each other, with the proviso that when R16 is m-chloro, R15 is not hydrogen;
- and
- wherein the 1,4-diketopyrrolo[3,4-c]pyrrole of formula (I) is different from the compound of formula (VI).
7 more elements
Dependencies are inferred from the claim text.