Back to results
US 7,102,014 B2Granted
Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
AssigneeClariant GmbH
InventorsJoachim Weber, Felix Wendelin Grimm, Erwin Dietz
Life of this patent
Estimating the term…
Abstract
The invention provides novel pigment dispersants of the formula (I): in which Q is a radical of the formula (Ia): s is a number from 0.1 to 4.0 and n is a number from 0 to 2.0; and provides pigment preparations comprising an organic base pigment and a pigment dispersant of the formula (I).
Claims9
A pigment dispersant of the formula (I):
- in which Q is a radical of the diketopyrrolopyrrole compound of the formula (Ia):
- s is a number from 0.1 to 4.0,
- n is 2-s,
- E+ is H+ or the equivalent Mm+/m of a metal cation Mm+ from main groups 1 to 5 or transition groups 1 or 2 or 4 to 8 of the periodic system of the chemical elements, m being 1, 2 or 3, an ammonium ion N+R9R10R11R12, where the substituents R9, R10, R11 and R12 independently of one another are each a hydrogen atom, C1-C30-alkyl, C2-C30-alkenyl, C5-C30-cycloalkyl, phenyl, (C1-C6)-alkyl-phenyl, (C1-C4)-alkylene-phenyl, or a (poly)alkyeneoxy group of the formula —[CH(R80)—CH(R80)—O]k—H, in which k is a number from 1 to 30 and the two radicals R80 independently of one another are hydrogen, C1-C4-alkyl or, if k is >1, a combination thereof;
- and in which alkyl, alkenyl, cycloalkyl, phenyl or alkylphenyl R9, R10, R11, and/or R12 may be substituted by amino, hydroxyl and/or carboxyl;
- or where the substituents R9 and R10, together with the quaternary nitrogen atom, are able to form a five- to seven-membered saturated ring system containing, if desired, further heteroatoms from the group consisting of O, S and N,
- or where the substituents R9, R10 and R11, together with the quaternary nitrogen atom, are able to form a five- to seven-membered aromatic ring system, containing, if desired, further heteroatoms from the group consisting of O, S and N, and to which additional rings may be fused if desired,
- and in which the two radicals Z are identical or different and Z has the definition Z1 or Z4, where
- Z1 is a radical of the formula (Ib):
- —[X—Y]qR3 (Ib)
- in which
- X is a C2-C8-alkylene radical, a C5-C7-cycloalkylene radical, or a combination of these radicals, it being possible for these radicals to be substituted by from 1 to 4 C1-C4-alkyl radicals, hydroxyl radicals, (C1-C4)-hydroxyalkyl radicals and/or by 1 or 2 further C5-C7-cycloalkyl radicals, or in which X, if q is >1, may also be a combination of said definitions;
- Y is a —O—,
- or —NR2— group,
- or in which Y, if q is >1, may also be a combination of said definitions;
- q is a number from 1 to 10;
- R2 and R3 independently of one another are a hydrogen atom, a substituted or unsubstituted, or partly fluorinated or perfluorinated, branched or unbranched (C1-C20)-alkyl group, a substituted or unsubstituted C5-C7-cycloalkyl group or a substituted or unsubstituted, or partly fluorinated or perfluorinated (C2-C20)-alkenyl group, it being possible for the substituents to be hydroxyl, phenyl, cyano, chloro, bromo, amino, C2-C4-acyl or C1-C4-alkoxy, or
- R2 and R3, together with the nitrogen atom, form a saturated, unsaturated or aromatic heteracyclic 5- to 7-membered ring containing, if desired, 1 or 2 further nitrogen, oxygen or sulfur atoms or carbonyl groups in the ring, being substituted if desired by 1.2 or 3 of the radicals OH, phenyl, CN, Cl, Br, C1-C4-alkyl, C1-C4-alkoxy, C2-C4 acyl and carbamoyl, and carrying, if desired, 1 or 2 benzo-fused saturated, unsaturated or aromatic, carbocyclic or heterocyclic rings;
- and where
- Z4 is hydrogen, hydroxyl, amino, phenyl, (C1-C4)-alkylene-phenyl, C6-C7-cycloalkyl or C1-C20-alkyl, it being possible for the phenyl ring, the (C1-C4)-alkylene-phenyl group and the alkyl group to be substituted by one or more substituents from the group consisting of Cl, Br, CN, NH2, OH, C6H5, mono-, di- or tri-C1-C4-alkoxy-substituted C6H6, carbamoyl, C2-C4-acyl and C1-C4-alkoxy, and it being possible for the phenyl ring and the (C1-C4)-alkylene-phenyl group to be substituted by NR2R2, or the alkyl group is perfluorinated or partly fluorinated.
17 more elements
Dependencies are inferred from the claim text.