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US 6,486,319 B1Granted
Thermochromic rylene dyes
AssigneesBASF SE, Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.
InventorsArno Böhm, Heinrich Schmeisser, Stefan Becker, Klaus Müllen
Life of this patent
Estimating the term…
Abstract
The invention relates to rylene dyes of the general formula (I), wherein the variables have the following meanings: R represents hydrogen; optionally substituted C1-C30 alkyl-C5-C8-cycloalkyl, aryl or hetaryl; R′ represents optionally substituted C2-C30 alkyl or C5-C8 cycloalkyl, substituted methyl; and n is 0 or 1. The invention also relates to the preparation and use of said dyes for coloring highly molecular organic and inorganic materials and to 9-amino-perylene-3,4-dicarboxylic acid imides (Va) as their intermediate products.
Claims10
A thermochromic rylene dye of formula I
- where
- R is hydrogen or C1-C30-alkyl, whose carbon chain may be interrupted by one or more —O—, —S—, —NR1—, —CO— and/or —SO2— groups and which may be monosubstituted or polysubstituted by cyano, C1-C6-alkoxy, aryl, which may be substituted by C1-C18-alkyl or C1-C6-alkoxy, or a 5- to 7-membered heterocyclic radical which is bonded via a nitrogen atom and may contain further heteroatoms and may be aromatic;
- C5-C8-cycloalkyl, whose carbon skeleton may be interrupted by one or more —O—, —S— and/or —NR1— groups and which may be monosubstituted or polysubstituted by C1-C6-alkyl;
- aryl or hetaryl, each of which may be monosubstituted or polysubstituted by C1-C18-alkyl, C1-C6-alkoxy, cyano, —CONHR2, —NHCOR2 and/or aryl- or hetarylazo, each of which may be substituted by C1-C10-alkyl, C1-C6-alkoxy or cyano, where
- R′ is C2-C30-alkyl, whose carbon chain may be interrupted by one or more —O— and/or —CO— groups and which may be monosubstituted or polysubstituted by cyano, C1-C6-alkoxy, C5-C8-cycloalkyl, whose carbon skeleton may be interrupted by one or more —O—, —S— and/or —NR1— groups and which may be C1-C6-alkyl-substituted, aryl, which may be substituted by C1-C18-alkyl or C1-C6-alkoxy, or a 5- to 7-membered heterocyclic radical which is bonded via a nitrogen atom and which may contain further heteroatoms and which may be aromatic;
- methyl, which is monosubstituted or disubstituted by aryl, hetaryl and/or C5-C8-cycloalkyl, each of which may be substituted by C1-C18-alkyl or C1-C6-alkoxy;
- C5-C8-cycloalkyl, whose carbon skeleton may be interrupted by one or more —O—, —S— and/or —NR1— groups and which may be monosubstituted or polysubstituted by C1-C6-alkyl;
- R1 is hydrogen or C1-C6-alkyl;
- R2 is hydrogen;
- C1-C18-alkyl;
- aryl or hetaryl, each of which may be substituted by C1-C6-alkyl, C1-C6-alkoxy or cyano;
- n is 0 or 1.
9 more elements
A process for the preparation of an aminorylenedicarboximide of formula V
- where
- R is hydrogen or C1-C30-alkyl, whose carbon chain may be interrupted by one or more —O—, —S—, —NR1—, —CO— and/or —SO2— groups and which may be monosubstituted or polysubstituted by cyano, C1-C6-alkoxy, aryl, which may be substituted by C1-C18-alkyl or C1-C6-alkoxy, or a 5- to 7-membered heterocyclic radical which is bonded via a nitrogen atom and may contain further heteroatoms and may be aromatic;
- C5-C8-cycloalkyl, whose carbon skeleton may be interrupted by one or more —O—, —S— and/or —NR1— groups and which may be monosubstituted or polysubstituted by C1-C6-alkyl;
- aryl or hetaryl, each of which may be monosubstituted or polysubstituted by C1-C18-alkyl, C1-C6-alkoxy, cyano, —CONHR2, —NHCOR2 and/or aryl- or hetarylazo, each of which may be substituted by C1-C10-alkyl, C1-C6-alkoxy or cyano;
- R1 is hydrogen or C1-C6-alkyl;
- R2 is hydrogen;
- C1-C18-alkyl;
- aryl or hetaryl, each of which may be substituted by C1-C6-alkyl, C1-C6-alkoxy or cyano;
- n is 0 or 1,
- which comprises reacting a bromorylenedicarboximide of formula III
- with a benzophenonimine of formula IV
- in the presence of an aprotic organic solvent, a transition-metal catalyst system and a base in an aryl-N coupling reaction, and hydrolysing the resultant ketimine in the presence of an acid and in the presence of a polar, aprotic solvent.
9 more elements
A 9-aminoperylene-3,4-dicarboximide of formula Va
- where
- R3 is hydrogen or C1-C30-alkyl, whose carbon chain may be interrupted by one or more —O—, —S—, —NR1—, —CO— and/or —SO2— groups and which may be monosubstituted or polysubstituted by cyano, C1-C6-alkoxy, aryl, which may be substituted by C1-C18-alkyl or C1-C6-alkoxy, or a 5- to 7-membered heterocyclic radical which is bonded via a nitrogen atom and may contain further heteroatoms and may be aromatic;
- C5-C8-cycloalkyl, whose carbon skeleton may be interrupted by one or more —O—, —S— and/or —NR1— groups and which may be monosubstituted or polysubstituted by C1-C6-alkyl;
- aryl or hetaryl, each of which may be monosubstituted or polysubstituted by C1-C18-alkyl, C1-C6-alkoxy, cyano, —CONHR2, —NHCOR2 and/or aryl- or hetarylazo, which may be substituted by C1-C10-alkyl, C1-C6-alkyl or cyano;
- R1 is hydrogen or C1-C6-alkyl;
- R2 is hydrogen, C1-C18-alkyl;
- aryl or hetaryl, each of which may be substituted by C1-C6-alkyl, C1-C6-alkoxy or cyano.
4 more elements
A process for the preparation of 9-bromoperylene-3,4-dicarboximide of formula IIIa
- where
- R is hydrogen or C1-C30-alkyl, whose carbon chain may be interrupted by one or more —O—, —S—, —NR1—, —CO— and/or —SO2— groups and which may be monosubstituted or polysubstituted by cyano, C1-C6-alkoxy, aryl, which may be substituted by C1-C18-alkyl or C1-C6-alkoxy, or a 5- to 7-membered heterocyclic radical which is bonded via a nitrogen atom and may contain further heteroatoms and may be aromatic;
- C5-C8-cycloalkyl, whose carbon skeleton may be interrupted by one or more —O—, —S— and/or —NR1— groups and which may be monosubstituted or polysubstituted by C1-C6-alkyl;
- aryl or hetaryl, each of which may be monosubstituted or polysubstituted by C1-C18-alkyl, C1-C6-alkoxy, cyano, —CONHR2, —NHCOR2 and/or aryl- or hetarylazo, which may be substituted by C1-C10-alkyl, C1-C6-alkoxy or cyano;
- R1 is hydrogen or C1-C6-alkyl;
- R2 is hydrogen;
- C1-C18-alkyl;
- aryl or hetaryl, each of which may be substituted by C1-C6-alkyl, C1-C6-alkoxy or cyano,
- which comprises reacting a perylene-3,4-dicarboximide of formula IIa
- with elemental bromine in the presence of an aliphatic monocarboxylic acid.
7 more elements
Dependencies are inferred from the claim text.