Surface-modified pigment preparations

1. A pigment composition, comprising:

(a) an organic pigment comprising a chromophore Q 1 ; and

(b) from 0.1 to 30 mol, based on 100 mol of the organic pigment (a), of a compound of formula (I):

wherein Q 2 is an m-valent residue of the chromophore Q 1 ;

R 1 and R 2 are each independently CN, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, or C 6 -C 18 aryl, wherein an alkyl group of the C 1 -C 6 alkyl or a cycloalkyl group of the C 3 -C 7 cycloalkyl is optionally substituted with D and an aryl group of the C 6 -C 18 aryl is optionally substituted with E; or

R 1 and R 2 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—, —NR 4 —, —N(—OR 4 )—, and —N + R 4 R 5 An − -;

R 3 is C 1 -C 25 alkyl, C 3 -C 25 alkenyl, C 7 -C 25 aralkyl, or a group of formula (II):

wherein an alkyl group of the C 1 -C 25 alkyl or an alkenyl group of the C 3 -C 25 alkenyl is optionally substituted with D and an aryl group of the C 7 -C 25 aralkyl is optionally substituted with E;

p and q are each independently 0 or 1;

X is —O—, —S—, —NR 6 —, —CONR 6 —, —COO—, or —C(═NR 7 )NR 8 —;

Y is C 1 -C 25 alkylene, wherein an alkylene group of the C 1 -C 25 alkylene optionally comprises, at an end or within a chain, at least one selected from the group consisting of —O—, —S—, —CO—, —COO—, —CONR 6 —, —NR 6 —, —N + R 6 R 5 An − -, an alicyclic ring, and an aromatic ring, and an alkylene group of the C 1 -C 25 alkylene is optionally substituted one or more times with Z;

Z is H; OR 9 OCOR 9 ; CN; NR 9 R 10 ; N + R 9 R 10 R 5 An − ; C 6 -C 18 aryl; or a heterocyclic C 2 -C 20 ring system wherein an aryl group of the C 6 -C 18 aryl is optionally substituted with E; COOR 9 ; CONR 9 R 10 ;

SO 2 R 9 ; SO 3 R 9 ; SO 2 NR 9 R 10 ; SO 3 − Cat + ; or PO(OR 9 ) 2 , the heterocyclic C 2 -C 20 ring system comprises at least one selected from the group consisting of O, S, N, NR 4 , NOR 4 , N + R 4 R 5 An − , and N + R 5 An − , and the heterocyclic C 2 -C 20 ring system is optionally substituted with E;

R 4 is H or C 1 -C 4 alkyl, wherein an alkyl group of the C 1 -C 4 alkyl is optionally substituted with D;

R 5 is H, C 1 -C 4 alkyl, C 7 -C 10 aralkyl, or C 3 -C 5 alkenyl;

R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are each independently H, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 5 -C 12 cycloalkyl, C 6 -C 18 aryl, or C 7 -C 18 aralkyl, wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 18 alkenyl, or a cycloalkyl group of the C 5 -C 12 cycloalkyl is optionally substituted with D;

and an aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E; or

R 9 and R 10 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—, —NR 4 —, and —N + R 4 R 5 An − -; or

R 12 and R 13 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, NR 4 , N + R 4 R 5 An − , and N + R 5 An − ; or

R 11 and R 12 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 C 1 -C 4 alkyl, C 1 -C 4 alkoxy, COOH, OH, halogen, NR 9 R 10 , —N + R 9 R 10 R 5 An − , SO 3 R 9 , SO 2 NR 9 R 10 , or SO 3 − Cat + ;

D is C 1 -C 4 alkoxy, 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.

2. The pigment composition according to claim 1 , wherein the organic pigment is at least one 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, phthalocyanine, and a quinacridone pigment, or a mixture of said pigments, including a solid solution or a mixed crystal.

3. The pigment composition according to claim 1 , wherein m is 1 or 2.

4. The pigment composition according to claim 1 , wherein R 1 and R 2 are each independently C 1 -C 6 alkyl, or

R 1 and R 2 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—, —NR 4 —, —N(—OR 4 )—, and —N + R 4 R 5 An − -;

R 3 is a group of formula (II):

p and q are 0,

Z is OR 9 , OCOR 9 ; CN; NR 9 R 10 , N + R 9 R 10 R 5 An − ; C 6 -C 18 aryl, or a heterocyclic C 2 -C 20 ring system wherein an aryl group of the C 6 -C 18 aryl is optionally substituted with E; COOR 9 ; CONR 9 R 10 ;

SO 2 R 9 ; SO 3 R 9 ; SO 2 NR 9 R 10 , SO 3 Cat + ;

or PO(OR 9 ) 2 ; the heterocyclic C 2 -C 20 ring system comprises at least one selected from the group consisting of O, S, N, NR 4 , NOR 4 , N + R 4 R 5 An and N + N 5 An − , and the heterocyclic C 2 -C 20 ring system is optionally substituted with E;

R 9 , R 10 , R 11 , R 12 , and R 13 are each independently H, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 5 -C 7 cycloalkyl, C 6 -C 18 aryl, and C 7 -C 18 aralkyl, wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 8 alkenyl or a cycloalkyl group of the C 5 -C 7 cycloalkyl is unsubstituted or optionally substituted with D;

and the aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E; or

R 9 and R 10 together with a linking nitrogen atom form a 5 or 6 membered heterocyclic ring, wherein the 5 or 6 membered heterocyclic ring is optionally substituted with E, and the 5 or 6 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of —O—, —NR 4 — and —N + R 4 R 5 An − -; or

R 12 and R 13 together with a linking nitrogen atom form a 5 or 6 membered heterocyclic ring, wherein the 5 or 6 membered heterocylic ring is optionally substituted with E, and the 5 or 6 membered heterocyclic ring optionally further comprises at least one selected from the group consisting of O, N, NR 4 , N + R 4 R 5 An − , and N + R 5 An − ; or

R 11 and R 12 together with a linking NCN group form a 5 to 6 membered cyclic amidine, wherein an amidine group of the 5 to 6 membered cyclic amidine is optionally substituted with E.

5. The pigment composition according to claim 1 , wherein R 1 and R 2 are each independently C 1 -C 6 alkyl or CN;

R 3 is a group of formula (II):

p and q are each independently 0 or 1, wherein a sum of p and q is 1 or 2;

X is —O—, —S—, —NR 6 —, —CONR 6 —, —COO—, or —C(═NR 7 )NR 8 —;

Y is C 1 -C 25 alkylene, wherein an alkylene group of the C 1 -C 25 alkylene optionally comprises at an end or within a chain, at least one selected from the group consisting of —O—, —S—, —CO—, —COO—, —CONR 6 —, —NR 6 —, —N + R 6 R 5 An − —, cyclohexylene, phenylene, and naphthylene, and an alkylene group of the C 1 -C 25 alkylene is optionally substituted one or more times with Z;

Z is H; OR 9 OCOR 9 ; CN; NR 9 R 10 , —N + R 9 R 10 R 5 An − ; C 6 -C 18 aryl, or an optionally saturated heterocyclic C 2 -C 20 ring system, wherein an aryl group of the C 6 -C 18 aryl is optionally substituted with E; COOR 9 ; CONR 9 R 10 ;

SO 2 R 9 ; SO 3 R 9 ; SO 2 NR 9 R 10 , SO 3 − Cat + ; or PO(OR 9 ) 2 , the optionally saturated heterocyclic C 2 -C 20 ring system comprises at least one selected from the group consisting of O, S, N, NR 4 , NOR 4 , N + R 4 R 5 An − , and N + R 5 An − , and the optionally saturated heterocyclic C 2 -C 20 ring system is optionally substituted with E;

R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are each independently H, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 5 -C 7 cycloalkyl, C 6 -C 18 aryl, or C 7 -C 18 aralkyl wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 8 alkenyl, or a cycloalkyl group of the C 5 -C 7 cycloalkyl is optionally substituted with D, and an aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E; or

R 9 and R 10 , or R 12 , and R 13 together with a linking nitrogen atom form a 5 or 6 membered heterocyclic ring, wherein the 5 or 6 membered heterocyclic ring is optionally substituted with E, and the 5 or 6 membered heterocyclic ring optionally further comprises —O—, —NR 4 —, or —N + R 4 R 5 An − -; or

R 11 and R 12 together with a linking NCN group form a 5 or 6 membered cyclic amidine, wherein an amidine group of the 5 or 6 membered cyclic amidine is optionally substituted with E.

6. The pigment composition according to claim 5 , wherein R 1 and R 2 are each independently methyl or ethyl,

R 3 is a group of formula (II):

p is 1, and q is 1;

X is —CONR 6 —, —COO—, or —C(═NR 7 )NR 8 —;

Y is C 1 -C 6 alkylene;

Z is OR 9 , OCOR 9 ; NR 9 R 10 ; or —N + R 9 R 10 R 5 An − ;

R 6 , R 7 , R 8 , R 9 , and R 10 are each independently H, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 5 -C 7 cycloalkyl, C 6 -C 18 aryl, or C 7 -C 18 aralkyl, wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 8 alkenyl or the cycloalkyl group of the C 5 -C 7 cycloalkyl is optionally substituted with D, and an aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E; or

R 9 and R 10 together with a linking nitrogen atom form a 5 or 6 membered heterocyclic ring, wherein the 5 or 6 membered ring is optionally substituted with E, and the 5 or 6 membered ring optionally further comprises —O—, —NR 4 —, or —N + R 4 R 5 An − .

7. The pigment composition according to claim 5 , wherein R 1 and R 2 are methyl or ethyl

R 3 is a group of formula (II):

p is 1 and q is 1;

X is —CONR 6 —, —COO—, or —C(═NR 7 )NR 8 —;

Y is C 1 -C 25 alkylene, wherein an alkylene group of the C 1 -C 25 alkylene optionally comprises at an end or within a chain, at least one selected from the group consisting of —O—, —CO—, —COO—, —CONR 6 —, —NR 6 —, and —N + R 6 R 5 An − -;

Z is phenyl, naphthyl, or a saturated heterocyclic C 2 -C 20 ring system or C 2 -C 18 hetaryl ring system, wherein the phenyl or the naphthyl is optionally substituted with E, the saturated heterocyclic C 2 -C 20 ring system or C 2 -C 18 hetaryl ring system comprises at least one selected from the group consisting of O, S, N, NR 4 , NOR 4 , N + R 4 R 5 An − and N + R 5 An − , and the saturated heterocyclic C 2 -C 20 ring system or C 2 -C 18 hetaryl ring system is optionally substituted with E;

R 6 , R 7 , and R 8 are each independently H or C 1 -C 18 alkyl.

8. The pigment composition according to claim 1 , wherein R 1 and R 2 are each independently C 1 -C 6 alkyl, or

R 1 and R 2 together with a linking carbon atom form a 5 to 12 membered alicyclic ring, wherein the 5 to 12 membered alicyclic ring is optionally substituted with E;

R 3 is C 1 -C 25 alkyl, C 3 -C 25 alkenyl, or C 7 -C 25 aralkyl, wherein an alkyl group of the C 1 -C 25 alkyl or an alkenyl group of the C 3 -C 25 alkenyl is optionally substituted with D, and an aryl group of the C 7 -C 25 aralkyl is optionally substituted with E, and

D and E are each independently C 1 -C 4 alkyl.

9. A compound of formula (I):

wherein Q 2 is an m-valent residue of a chromophore Q 1 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;

R 1 and R 2 are each independently CN, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, and C 6 -C 18 aryl, wherein an alkyl group of the C 1 -C 6 alkyl or a cycloalkyl group of the C 3 -C 7 cycloalkyl is optionally substituted with D, and an aryl group of the C 6 -C 18 aryl is optionally substituted with E; or

R 1 and R 2 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—, —NR 4 —, —N(—OR 4 )—, and —N + R 4 R 5 An − -;

R 3 is C 1 -C 25 alkyl, C 3 -C 25 alkenyl, C 7 -C 25 aralkyl, or a group of formula (II):

wherein an alkyl group of the C 1 -C 25 alkyl or an alkenyl group of the C 3 -C 25 alkenyl is optionally substituted with D, an aryl group of the C 7 -C 25 aralkyl is optionally substituted with E,

p and q are each independently 0 or 1;

X is —O—, —S—, —NR 6 —, —CONR 6 —, —COO—, or —C(═NR 7 )NR 8 —;

Y is C 1 -C 25 alkylene, wherein an alkylene group of the C 1 -C 25 alkylene optionally comprises at an end or within a chain, at least one selected from the group consisting of —O—, —S—, —CO—, —COO—, —CONR 6 —, —NR 6 —, —N + R 6 R 5 An − , an alicyclic ring, and an aromatic ring, and the alkylene group is optionally substituted one or more times with Z;

Z is H; OR 9 ; OCOR 9 ; CN; NR 9 R 10 ; N + R 9 R 10 R 5 An − ; C 6 -C 18 aryl; or a heterocyclic C 2 -C 20 ring system, wherein an aryl group of the C 6 -C 18 aryl is optionally substituted with E; COOR 9 ; CONR 9 R 10 ;

SO 2 R 9 ; SO 3 R 9 ; SO 2 NR 9 R 10 SO 3 − Cat + ; or PO(OR 9 ) 2 ; wherein the heterocyclic C 2 -C 20 ring system comprises at least one selected from the group consisting of O, S, N, NR 4 , NOR 4 , N + R 4 R 5 An − , and N + R 5 An − , the heterocyclic C 2 -C 20 ring system is optionally substituted with E;

R 4 is H or C 1 -C 4 alkyl, wherein an alkyl group of the C 1 -C 4 alkyl is optionally substituted with D;

R 5 is H, C 1 -C 4 alkyl, C 7 -C 10 aralkyl, or C 3 -C 5 alkenyl;

R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are each independently H, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 5 -C 12 cycloalkyl, C 6 -C 18 aryl, or C 7 -C 18 aralkyl wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 18 alkenyl, or a cycloalkyl group of the C 5 -C 12 cycloalkyl is optionally substituted with D;

and an aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E; or

R 9 and R 10 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—, —NR 4 —, and —N + R 4 R 5 An − -; or

R 12 and R 13 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, NR 4 , N + R 4 R 5 An − , and N + R 5 An − ; or

R 11 and R 12 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 C 1 -C 4 alkyl, C 1 -C 4 alkoxy, COOH, OH, halogen, NR 9 R 10 , —N + R 9 R 10 R 5 An − , SO 3 R 9 , SO 2 NR 9 R 10 , or SO 3 − Cat + ;

D is C 1 -C 4 alkoxy, 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.

10. A process for preparing the pigment composition of claim 1 , the process comprising:

treating a suspension of the organic pigment with a radical of formula (IV):

11. An azo compound of formula (V):

wherein

R 1 and R 2 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(—OR 4 )—;

R 3 is CN; and

R 14 is phenyl, triphenylmethyl, or CONR 15 R 16 ,

wherein R 15 and R 16 are each independently H, C 1 -C 4 alkyl, —

or

the azo compound of formula (V),

wherein

R 1 and R 2 are each independently CN, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, or C 6 -C 18 aryl, wherein an alkyl group of the C 1 -C 6 alkyl or a cycloalkyl group of the C 3 -C 7 cycloalkyl is optionally substituted with D, and an aryl group of the C 6 -C 18 aryl, is optionally substituted with E;

R 3 is a group of formula (II):

p and q are each independently 0 or 1;

X is —CONR 6 —, —COO—, or —C(═NR 7 )NR 8 —;

Y is C 1 -C 25 alkylene, wherein an alkylene group of the C 1 -C 25 alkylene optionally comprises at an end or within a chain, at least one group selected from the group consisting of —O—, —S—, —CO—, —COO—, —CONR 6 —, —NR 6 —, —N + R 6 R 5 An − -, an alicyclic ring, and an aromatic ring, wherein the alkylene group is optionally substituted one or more times with Z;

Z is SO 2 R 9 ; SO 3 R 9 ; SO 2 NR 9 R 10 , SO 3 Cat + ; PO(OR 9 ) 2 ; a saturated heterocyclic C 2 -C 20 ring system; or C 2 -C 18 heteroaryl, wherein the saturated heterocyclic C 2 -C 20 ring system comprises at least one selected from the group consisting of NR 4 , NOR 4 , and N + R 4 R 5 An − and the saturated heterocyclic C 2 -C 20 ring system is optionally substituted with E;

R 4 is H or C 1 -C 4 alkyl, wherein an alkyl group of the C 1 -C 4 alkyl is optionally substituted with D;

R 5 is H, C 1 -C 4 alkyl, C 7 -C 10 aralkyl, or C 3 -C 5 alkenyl;

R 6 , R 7 , R 8 , R 9 , and R 10 are each independently H, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 5 -C 12 cycloalkyl, C 6 -C 18 aryl, or C 7 -C 18 aralkyl, wherein an alkyl group of the C 1 -C 18 alkyl, an alkenyl group of the C 3 -C 18 alkenyl, or a cycloalkyl group of the C 5 -C 12 cycloalkyl is optionally substituted with D, an aryl group of the C 6 -C 18 aryl or the C 7 -C 18 aralkyl is optionally substituted with E;

E is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, COOH, OH, halogen, NR 9 R 10 , —N + R 9 R 10 R 5 An − , SO 3 R 9 , SO 2 NR 9 R 10 , or SO 3 − Cat + ;

D is C 1 -C 4 alkoxy, OH, COOH, or halogen;

An − is an equivalent of an anion; and

Cat + is an equivalent of a cation.

12. A colored composition, comprising:

a high molecular weight organic material, and

from 0.01 to 70% by weight, based on a weight of the high molecular weight organic material, of the pigment composition of claim 1 .

13. The colored composition of claim 12 , wherein the colored composition is a coating composition and the high molecular weight organic material is an organic film-forming binder.

14. A coating prepared by a method comprising curing the coating composition of the colored composition of claim 13 on a substrate.

15. A pigmenting plastic, a coating composition or a printing ink, comprising:

the pigment composition of claim 1 .