Surface-modified pigment compositions

1. A pigment composition, comprising:

(a) (a1) carbon black or (a2) an organic pigment comprising a chromophore Q 1 comprising a group of formula (I),

 or a cis/trans isomer thereof, wherein Z 1 and Z 2 are each independently of the other, O or N—, each C· is independently of all other C·, a carbon atom with an electron in a p orbital, and n is an integer from 1 to 4; and

(b) from 0.5 to 30 moles, based on 3.5·10 4 g of the carbon black (a1) or 100 moles of the organic pigment (a2), of a compound comprising a chromophore of formula (II),

wherein,

Q 2 is an m-valent residue of carbon black or of the chromophore Q 1 ;

G 1 is

 with one extremity of G 1 attached to an aromatic C atom in a meta position relative to Q 2 and another extremity of G 1 attached to the aromatic C atom in a para position relative to Q 2 ;

R 8 has, independently from R 4 the same definition as R 4 ;

R 1 , R 2 and R 3 are each, independently of the others H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR S , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

each R 4 is, independently from any other R 4 , H or R 7 ;

each R 5 is, independently from any other R 5 , H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

R 6 is H, a direct bond to a geminal R 5 or R 7 thus forming a 3- to 8-membered homo- or heterocyclic ring, or R 7 which is independently from any other R 7 ;

each R 7 is, independently of any other R 7 , C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl or C 3 -C 8 cycloalkenyl which are each unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen, an amino and a hydroxy, and are uninterrupted or interrupted by one or more —O—, —S—, —NH— or —N(C 1 -C 4 alkyl)-; and

m is an integer from 1 to 4.

2. The composition of claim 1 , wherein the chromophore of the formula (II) is of formula

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

R 1 , R 2 , R 3 , R 4 and R 8 are all H;

each R 5 is, independently from any other R 5 , H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

R 6 is H, a direct bond to a geminal R 5 or R 7 thus forming a 3- to 8-membered homo- or heterocyclic ring, or R7 which is independently from any other R 7 ;

each R 7 is, independently of any other R 7 , C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl or C 3 -C 8 cycloalkenyl which are each unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen, an amino and a hydroxy, and are uninterrupted or interrupted by one or more —O—, —S—, —NH— or —N(C 1 -C 4 alkyl)-; and

m is an integer from 1 to 4.

3. A colour filter, comprising image points (pixels) of at least three colours and optionally a black matrix, wherein a fraction of the image points, the optional black matrix, or both, comprise the pigment composition of claim 1 .

4. The pigment composition of claim 1 , wherein the composition comprises from 0.8 to 15 moles of the compound comprising the chromophore of formula (II).

5. The pigment composition of claim 1 , wherein each R 4 is, independently from any other R 4 , H, methyl, or ethyl.

6. The pigment composition of claim 1 , wherein m is an integer 1 or 2.

7. A compound, comprising a chromophore of formula (II),

wherein:

m is an integer from 1 to 4;

Q 2 is a residue of carbon black or of a chromophore comprising a group of the formula (I),

 or a cis/trans isomer thereof, wherein Z 1 and Z 2 are each, independently of the other O or N—, each C· is, independently of all other C·, a carbon atom with an electron in a p orbital, and n is an integer from 1 to 4;

G 1 is

 with one extremity of G 1 attached to an aromatic C atom in a meta position relative to Q 2 and the other extremity of G 1 attached to the aromatic C atom in para position to Q 2 ;

R 8 has, independently from R 4 , the same definition as R 4 ;

R 1 , R 2 and R 3 are each independently of the others, H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

each R 4 is independently from any other R 4 , H or R 7 ;

each R 5 is, independently from any other R 5 , H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

R 6 is H, a direct bond to a geminal R 5 or R 7 thus forming a 3- to 8-membered homo- or heterocyclic ring, or R 7 , which is independently from any other R 7 ; and

each R 7 is, independently of any other R 7 , C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl or C 3 -C 3 cycloalkenyl which are each unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen, an amino and a hydroxy, and are uninterrupted or interrupted by one or more —O—, —S—, —NH— or —N(C 1 -C 4 alkyl).

8. A rheology modifier, comprising the compound of claim 7 .

9. A process for preparing the compound of claim 7 , the process comprising treating a suspension of carbon black, or of an organic pigment comprising a chromophore Q 1 , with a diazonium salt, or with an aromatic amine and a diazolating agent, in a liquid medium,

wherein:

the chromophore Q 1 comprises a group of formula (I),

 or a cis/trans isomer thereof, wherein Z 1 and Z 2 are each independently of the other, O or N—, each C· is independently of all ethers other C·, a carbon atom with an electron in a p orbital, and n is an integer from 1 to 4;

the diazonium salt is a salt of formula (III),

 and

the aromatic amine is an amine of formula (IV),

 wherein X − is an inorganic anion; G 1 is

R 8 has, independently from R 4 , the same definition as R 4 ;

R 1 , R 2 and R 3 are each independently of the others, H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

each R 4 is independently from any other R 4 , H or R 7 ;

each R 5 is, independently from any other R 5 , H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

R 6 is H, a direct bond to a geminal R 5 or R 7 thus forming a 3- to 8-membered homo- or heterocyclic ring, or R7, which is independently from any other R 7 ; and

each R 7 is, independently of any other R 7 , C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl or C 3 -C 3 cycloalkenyl which are each unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen, an amino and a hydroxy, and are uninterrupted or interrupted by one or more —O—, —S—, —NH— or —N(C 1 -C 4 alkyl).

10. The compound of claim 7 , wherein m is an integer 1 or 2.

11. The compound of claim 7 , wherein each R 4 is, independently from any other R 4 , H, methyl or ethyl.

12. A coating composition, comprising

(a) from 0 to 50% by weight of a volatile part,

(b) from 10 to 50% by weight of a non-volatile, essentially colourless part, and

(c) from 5 to 85% by weight of (c1) a colourant part comprising carbon black, (c2) an organic pigment comprising a chromophore Q 1 comprising a group of formula (I),

 or a cis/trans isomer thereof, wherein Z 1 and Z 2 are each, independently of the other, O or N—, each C· is, independently of all other C·, a carbon atom with an electron in a p orbital, and n is an integer from 1 to 4, or (c3) both the colourant part (c1) and the organic pigment (c2),

all above weight percentages are based on a total weight of the curing coating composition which is always 100%, and

(d) from 0.5 to 30 moles, based on 3.5·10 4 g of the carbon black or 100 moles of the organic pigment, of a compound comprising a chromophore of formula (II),

wherein:

Q 2 is an m-valent residue of carbon black or of the chromophore Q 1 ;

G 1 is

 with one extremity of G 1 attached to an aromatic C atom in a meta position relative to Q 2 and another extremity of G 1 attached to an aromatic C atom in a para position relative to Q 2 ;

R 8 , independently from R 4 , has the same definition as R 4 ;

R 1 , R 2 and R 3 are each independently of the others H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

each R 4 is independently from any other R 4 , H or R 7 ;

each R 5 is, independently from any other R 5 , H, halogen, OH, NH 2 , NO 2 , R 7 , OR 7 , SR 7 , NR 6 R 7 , COR 7 , CO 2 R 7 , CONR 6 R 7 or SO 2 R 7 ;

R 6 is H, a direct bond to a geminal R 5 or R 7 thus forming a 3- to 8-membered homo- or heterocyclic ring, or R 7 , which is independently from any other R 7 ;

each R 7 is, independently of any other R 7 , C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl or C 3 -C 8 cycloalkenyl which are each unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen, an amino and a hydroxy, and are uninterrupted or interrupted by one or more —O—, —S—, —NH— or —N(C 1 -C 4 alkyl)-; and

m is an integer from 1 to 4.

13. The coating composition of claim 12 , wherein the chromophore Q 1 is [Q 2 H] m .

14. A coating, comprising the composition of claim 12 .

15. A coating prepared by curing the coating composition of claim 14 .

16. A color filter, comprising the composition of claim 12 .

17. The coating composition of claim 12 , comprising from 5 to 30% by weight of the volatile part (a).

18. The coating composition of claim 12 , comprising from 0.8 to 15 moles of the compound (d) comprising the chromophore of formula (II).