Surface-modified pigment preparations

A compound of formula (I):

• wherein Q2 is an m-valent residue of a chromophore Q1 of at least one organic pigment selected from the group consisting of bis(anthraquinone-1-yl-amino), bis(anthraquinone-1-yl-oxy), 1,1′-dianthraquinolyl, diketopyrrolopyrrole, indanthrone, isoindoline, isoindolinone, perylene, 1-phenylhydrazono-2-oxy-3-carbamoyl-1,2-dihydronaphthalene, and a quinacridone pigment, including a solid solution or a mixed crystal;
• R1 and R2 are each independently CN, C1-C6alkyl, C3-C7cycloalkyl, and C6-C18aryl, wherein an alkyl group of the C1-C6alkyl or a cycloalkyl group of the C3-C7cycloalkyl is optionally substituted with D, and an aryl group of the C6-C18aryl is optionally substituted with E;
• or
• R1 and R2 together with a linking carbon atom form a 5 to 12 membered ring, wherein the 5 to 12 membered ring is optionally substituted with E, and the 5 to 12 membered ring optionally further comprises at least one selected from the group consisting of —O—, —NR4—, —N(—OR4)—, and —N+R4R5 An−-;
• R3 is C1-C25alkyl, C3-C25alkenyl, C7-C25aralkyl, or a group of formula (II):
• wherein an alkyl group of the C1-C25alkyl or an alkenyl group of the C3-C25alkenyl is optionally substituted with D, an aryl group of the C7-C25aralkyl is optionally substituted with E,
• p and q are each independently 0 or 1;
• X is —O—, —S—, —NR6—, —CONR6—, —COO—, or —C(═NR7)NR8—;
• Y is C1-C25alkylene, wherein an alkylene group of the C1-C25alkylene optionally comprises at an end or within a chain, at least one selected from the group consisting of —O—, —S—, —CO—, —COO—, —CONR6—, —NR6—, —N+R6R5 An−, an alicyclic ring, and an aromatic ring, and the alkylene group is optionally substituted one or more times with Z;
• Z is H;
• OR9;
• OCOR9;
• CN;
• NR9R10;
• N+R9R10R5 An−;
• C6-C18aryl;
• or a heterocyclic C2-C20ring system, wherein an aryl group of the C6-C18aryl is optionally substituted with E;
• COOR9;
• CONR9R10;
• SO2R9;
• SO3R9;
• SO2NR9R10 SO3−Cat+;
• or PO(OR9)2;
• wherein the heterocyclic C2-C20ring system comprises at least one selected from the group consisting of O, S, N, NR4, NOR4, N+R4R5 An−, and N+R5 An−, the heterocyclic C2-C20ring system is optionally substituted with E;
• R4 is H or C1-C4alkyl, wherein an alkyl group of the C1-C4alkyl is optionally substituted with D;
• R5 is H, C1-C4alkyl, C7-C10aralkyl, or C3-C5alkenyl;
• R6, R7, R8, R9, R10, R11, R12, and R13 are each independently H, C1-C18alkyl, C3-C18alkenyl, C5-C12cycloalkyl, C6-C18aryl, or C7-C18aralkyl wherein an alkyl group of the C1-C18alkyl, an alkenyl group of the C3-C18alkenyl, or a cycloalkyl group of the C5-C12cycloalkyl is optionally substituted with D;
• and an aryl group of the C6-C18aryl or the C7-C18aralkyl is optionally substituted with E;
• or
• R9 and R10 together with a linking nitrogen atom form a 5 to 7 membered heterocyclic ring, wherein the 5 to 7 membered heterocyclic ring is optionally substituted with E, and wherein the 5 to 7 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of —O—, —NR4—, and —N+R4R5 An−-;
• or
• R12 and R13 together with a linking nitrogen atom form a 5 to 7 membered heterocyclic ring, wherein the 5 to 7 membered heterocyclic ring is optionally substituted with E, and the 5 to 7 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of O, N, NR4, N+R4R5 An−, and N+R5 An−;
• or
• R11 and R12 together with a linking NCN group form a 5 to 7 membered cyclic amidine, wherein an amidine group of the 5 to 7 membered cyclic amidine is optionally substituted with E;
• E is C1-C4alkyl, C1-C4alkoxy, COOH, OH, halogen, NR9R10, —N+R9R10R5 An−, SO3R9, SO2NR9R10, or SO3−Cat+;
• D is C1-C4alkoxy, OH, COOH, or halogen;
• An− is an equivalent of an anion;
• Cat+ is an equivalent of a cation;
• m is an integer from 1 to 4;
• and
• each group of formula (III):
• is selected independently.

An azo compound of formula (V):

• wherein
• R1 and R2 together with a linking carbon atom form a 8 to 12 membered ring or a 5 to 7 membered ring wherein the 8 to 12 membered ring or the 5 to 7 membered ring is optionally substituted with E, and the 5 to 7 membered ring comprises one or more groups of —N(—OR4)—;
• R3 is CN;
• and
• R14 is phenyl, triphenylmethyl, or CONR15R16,
• wherein R15 and R16 are each independently H, C1-C4alkyl, —
• or
• the azo compound of formula (V),
• wherein
• R1 and R2 are each independently CN, C1-C6alkyl, C3-C7cycloalkyl, or C6-C18aryl, wherein an alkyl group of the C1-C6alkyl or a cycloalkyl group of the C3-C7cycloalkyl is optionally substituted with D, and an aryl group of the C6-C18aryl, is optionally substituted with E;
• R3 is a group of formula (II):
• p and q are each independently 0 or 1;
• X is —CONR6—, —COO—, or —C(═NR7)NR8—;
• Y is C1-C25alkylene, wherein an alkylene group of the C1-C25alkylene optionally comprises at an end or within a chain, at least one group selected from the group consisting of —O—, —S—, —CO—, —COO—, —CONR6—, —NR6—, —N+R6R5 An−-, an alicyclic ring, and an aromatic ring, wherein the alkylene group is optionally substituted one or more times with Z;
• Z is SO2R9;
• SO3R9;
• SO2NR9R10, SO3 Cat+;
• PO(OR9)2;
• a saturated heterocyclic C2-C20ring system;
• or C2-C18heteroaryl, wherein the saturated heterocyclic C2-C20ring system comprises at least one selected from the group consisting of NR4, NOR4, and N+R4R5 An− and the saturated heterocyclic C2-C20ring system is optionally substituted with E;
• R4 is H or C1-C4alkyl, wherein an alkyl group of the C1-C4alkyl is optionally substituted with D;
• R5 is H, C1-C4alkyl, C7-C10aralkyl, or C3-C5alkenyl;
• R6, R7, R8, R9, and R10 are each independently H, C1-C18alkyl, C3-C18alkenyl, C5-C12cycloalkyl, C6-C18aryl, or C7-C18aralkyl, wherein an alkyl group of the C1-C18alkyl, an alkenyl group of the C3-C18alkenyl, or a cycloalkyl group of the C5-C12cycloalkyl is optionally substituted with D, an aryl group of the C6-C18aryl or the C7-C18aralkyl is optionally substituted with E;
• E is C1-C4alkyl, C1-C4alkoxy, COOH, OH, halogen, NR9R10, —N+R9R10R5 An−, SO3R9, SO2NR9R10, or SO3−Cat+;
• D is C1-C4alkoxy, OH, COOH, or halogen;
• An− is an equivalent of an anion;
• and
• Cat+ is an equivalent of a cation.