Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations

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).

1 . 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 a number from 0 to 2,  
 E + is H + or the equivalent M m+ /m of a metal cation M m+ 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 + R 9 R 10 R 11 R 12 , where the substituents R 9 , R 10 , R 11  and R 12  independently of one another are each a hydrogen atom, C 1 -C 30 -alkyl, C 2 -C 30 -alkenyl, C 5 -C 30 -cycloalkyl, phenyl, (C 1 -C 8 )-alkyl-phenyl, (C 1 -C 4 )-alkylene-phenyl, or a (poly)alkyleneoxy group of the formula —[CH(R 80 )-CH(R 80 )—O] k —H, in which k is a number from 1 to 30 and the two radicals R 80  independently of one another are hydrogen, C 1 -C 4 -alkyl or, if k is>1, a combination thereof;  
 and in which alkyl, alkenyl, cycloalkyl, phenyl or alkylphenyl is optionally substituted by amino, hydroxyl, carboxyl, or a combination thereof;  
 or where the substituents R 9  and R 10 , together with the quaternary nitrogen atom, are able to form a five- to seven-membered saturated ring system optionally containing further heteroatoms from the group consisting of O, S and N, or where the substituents R 9 , R 10  and R 11 , together with the quaternary nitrogen atom, are able to form a five- to seven-membered aromatic ring system, optionally containing further heteroatoms from the group consisting of O, S and N, and to which additional rings are optionally fused,  
 or in which E+defines an ammonium ion of the formula (Ic)  
                 
 
 in which  
 R 15 , R 16 , R 17  and R 18  independently of one another are hydrogen or a (poly)alkyleneoxy group of the formula —[CH(R 80 )—CH(R 80 )O] k —H, in which k is a number from 1 to 30 and the two radicals R 80  independently of one another are hydrogen, C 1 -C 4 -alkyl or, if k is>1, a combination thereof;  
 q is a number from 1 to 10,  
 p is a number from 1 to 5, where p is≦q+1;  
 T is a branched or unbranched C 2 -C 6 -alkylene radical; or in which T, if q is>1, may also be a combination of branched or unbranched C 2 -C 6 -alkylene radicals;  
 and in which the two radicals Z are identical or different and Z has the definition Z 1  or Z 4 , where  
 Z 1  is a radical of the formula (Ib)  
 —[X—Y] q R 3    (Ib)  
 in which  
 X is a C 2 -C 6 -alkylene radical, a C 5 -C 7 -cycloalkylene radical, or a combination of these radicals, it being possible for these radicals to be substituted by from 1 to 4 C 1 -C 4 -alkyl radicals, hydroxyl radicals, (C 1 -C 4 )-hydroxyalkyl radicals, by 1 or 2 C 5 -C 7 -cycloalkyl radicals, or in which X, if q is>1, may also be a combination of said definitions;  
 Y is a —O—,  
                 
 
 or in which Y, if q is>1, may also be a combination of said definitions;  
 q is a numberfrom 1 to 10;  
 R 2  and R 3  independently of one another are a hydrogen atom, a substituted or unsubstituted, or partly fluorinated or perfluorinated, branched or unbranched (C 1 -C 20 )-alkyl group, a substituted or unsubstituted C 5 -C 7 -cycloalkyl group or a substituted or unsubstituted, or partly fluorinated or perfluorinated (C 2 -C 20 )-alkenyl group, it being possible for the substituents to be hydroxyl, phenyl, cyano, chloro, bromo, amino, C 2 -C 4 -acyl or C 1 -C 4 -alkoxy, or  
 R 2  and R 3 , together with the nitrogen atom, form a saturated, unsaturated or aromatic heterocyclic 5- to 7-membered ring optionally containing 1 or 2 further nitrogen, oxygen or sulfur atoms or carbonyl groups in the ring, optionally being substituted by 1, 2 or 3 of the radicals OH, phenyl, CN, Cl, Br, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -acyl and carbamoyl, and optionally carrying 1 or 2 benzo-fused saturated, unsaturated or aromatic, carbocyclic or heterocyclic rings;  
 and where  
 Z 4  is hydrogen, hydroxyl, amino, phenyl, (C 1 -C 4 )-alkylene-phenyl, C 5 -C 7 -cycloalkyl or C 1 -C 20 -alkyl, it being possible for the phenyl ring, the (C 1 -C 4 )-alkylene-phenyl group and the alkyl group to be substituted by one or more substituents from the group consisting of Cl, Br, CN, NH 2 , OH, C 6 H 5 , mono-, di- or tri-C 1 -C 4 -alkoxy-substituted C 6 H 5 , carbamoyl, C 2 -C 4 -acyl and C 1 -C 4 -alkoxy, and it being possible for the phenyl ring and the (C 1 -C 4 )-alkylene-phenyl group to be substituted by NR 2 R 3 , or the alkyl group is perfluorinated or partly fluorinated.  
 
     
     
         2 . The pigment dispersant as claimed in    claim 1   , wherein s is a number from 0.2 to 3.0, preferably from 0.5 to 2.5; and n is a number from 0 to 0.5.  
     
     
         3 . The pigment dispersant as claimed in    claim 1   , wherein s is a number from 0.5 to 2.5, and n is a number from 0 to 0.2.  
     
     
         4 . The pigment dispersant as claimed in    claim 1   , wherein 
 R 2  and R 3  independently of one another are a hydrogen atom, a C 1 -C 6 -alkyl group or a C 1 -C 6 -alkyl group substituted by 1 or 2 substituents from the group consisting of hydroxyl, acetyl, methoxy, ethoxy, chloro and bromo, or    R 2  and R 3 , together with the adjacent nitrogen atom, form an imidazolyl, piperidinyl, morpholinyl, pipecolinyl, pyrrolyl, pyrrolidinyl, pyrazolyl, pyrrolidinonyl, indolyl or piperazinyl ring.    
     
     
         5 . The pigment dispersant as claimed in    claim 1   , wherein Z 1  has the definition —[(CH 2 ) 3 —NH] 2 —H, —(CH 2 —CH 2 —NH) 2 H, —(CH 2 ) 3 —NH—(CH 2 ) 2 —NH—(CH 2 ) 3 —NH 2 ,  
                 
—(CH 2 ) 3 —N(CH 3 )—(CH 2 ) 3 —NH 2 , —(CH 2 ) 3 —O—(CH 2 ) 2 —O—(CH 2 ) 3 —NH 2 , —(CH 2 ) 3 —O—(CH 2 ) 3 —O—(CH 2 ) 3 —NH 2 , —(CH 2 ) 2 —NH—(CH 2 ) 3 —NH 2 , —(CH 2 ) 3 —NH—(CH 2 ) 2 —NH 2 , —(CH 2 —CH 2 —NH) 3 —H, —(CH 2 —CH 2 —NH) 4 —H, —(CH 2 —CH 2 —NH) 5 —H, —(CH 2 ) 3 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 3 —NH 2 , —(CH 2 ) 3 —O—(CH 2 ) 4 —O—(CH 2 ) 3 —NH 2 ,  
                 

 —(CH 2 ) 2 —OH, —(CH 2 ) 3 —OH, —CH 2 —CH 2 —CH(CH 3 )—OH, —CH(CH 2 —CH 3 )CH 2 —OH, —CH(CH 2 OH) 2 , —(CH 2 ) 2 —O—(CH 2 ) 2 —OH or —(CH 2 ) 3 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —OH; —(CH 2 ) 2 —NH 2 , —(CH 2 ) 3 —NH 2 , —CH 2 —CH(CH 3 )—NH 2 , —CH 2 —C(CH 3 ) 2 —CH 2 —NH 2 ,  
                 
 
 —(CH 2 ) 2 —N(CH 3 ) 2 , —(CH 2 ) 2 —NH—CH 2 —CH 3 , —(CH 2 ) 2 —N(CH 2 —CH 3 ) 2 , —(CH 2 ) 3 —NH—CH 3 , —(CH 2 ) 3 —N(CH 3 ) 2 , —(CH 2 ) 3 —NH—CH 2 —CH 3  or —(CH 2 ) 3 —N(CH 2 —CH 3 ) 2 .  
 
     
     
         6 . The pigment dispersant as claimed in    claim 1   , wherein Z 4  has the definition hydrogen, amino, phenyl, benzyl, NR R 3 -substituted phenyl or benzyl, C 1 -C 6 -alkyl, or a C 2 -C 6 -alkyl, phenyl or benzyl substituted by 1 or 2 substituents from the group consisting of hydroxyl, acetyl, methoxy and ethoxy.  
     
     
         7 . The pigment dispersant as claimed in    claim 1   , wherein X is a C 2 -C 4 -alkylene radical or cyclohexylene.  
     
     
         8 . A process for preparing a pigment dispersant as claimed in    claim 1   , which comprises chlorosulfonating a diketopyrrolopyrrole compound of the formula (Ia)  
                   
       and reacting the resultant sulfochloride with an amine of the formula (V)  
                 
 
       .  
     
     
         9 . A pigment preparation comprising 
 a) at least one organic base pigment, and    b) at least one pigment dispersant of the formula (I) as claimed in    claim 1   .    
     
     
         10 . A pigment preparation as claimed in    claim 9   , wherein the organic base pigment a) is a perylene, perinone, quinacridone, quinacridonequinone, anthraquinone, anthanthrone, benzimidazolone, disazo condensation, azo, indanthrone, phthalocyanine, triarylcarbonium, dioxazine, aminoanthraquinone, diketopyrrolopyrrole, thioindigo, isoindoline, isoindolinone, pyranthrone, isoviolanthrone or carbon black pigment or a mixture thereof.  
     
     
         11 . The pigment preparation as claimed in    claim 9   , consisting essentially of 
 a) from 50 to 99.5% by weight of at least one base pigment a),    b) from 0.5 to 20% by weight of at least one pigment dispersant b) of the formula (I),    c) from 0 to 20% by weight of surfactants, and    d) from 0 to 20% by weight of further customary additives, the fractions of the respective components being based on the overall weight of the preparation (100% by weight).    
     
     
         12 . The pigment preparation as claimed in    claim 9   , consisting essentially of 
 a) from 60 to 98.8% by weight of at least one base pigment a),    b) from 1 to 15% by weight of at least one pigment dispersant b) of the formula (I),    c) from 0.1 to 15% by weight of surfactants, and    d) from 0.1 to 10% by weight of further customary additives, the fractions of the respective components being based on the overall weight of the preparation (100% by weight).    
     
     
         13 . A process for preparing a pigment preparation as claimed in    claim 9   , which comprises mixing the pigment dispersant(s) as per b) and the base pigment(s) with one another.  
     
     
         14 . A method of pigmenting high molecular mass organic material, electrophotographic toners and developers, and writing, drawing and printing inks comprising the step of adding a pigment preparation as claimed in    claim 9    to a high molecular mass organic material, electrophotographic toner and developer, or to the basis of a writing, drawing or printing ink to be pigmented.  
     
     
         15 . The method as claimed in    claim 14   , wherein the high molecular mass organic material is a plastic, a resin, a varnish or a paint.  
     
     
         16 . A prepared pigment formulation consisting essentially of 
 a) one or more organic base pigments;    b) one or more pigment dispersants of the formula (I) as claimed in    claim 1   ; and    c) a high molecular mass organic material.