Printing process using specified AZO compounds

1. A process for printing an image on a substrate comprising applying thereto a composition comprising a liquid medium and a compound of Formula (1):

T-Q-N═N-L-T  Formula (1)

wherein:

each T independently is an azo group of the formula A-N═N— wherein each A independently is an optionally substiuted aryl, heteroaryl, non-aromatic heterocyclic or an alkenyl group;

Q is an optionally substituted, optionally metallised 1,8-dihydroxynaphthyl group of Formula (4);

L is a divalent organic linker group; and wherein each A and L independently carries 1 or 2 substituents, and with the proviso that at least one of the groups represented by T comprises a water-solubilising group.

2. A composition comprising a liquid medium and a compound of Formula (1):

T-Q-N═N-L-T  Formula (1)

wherein:

each T independently is an azo group of the formula A-N═N— wherein each A independently is an optionally substiuted aryl, heteroaryl, non-aromatic heterocyclic or an alkenyl group;

Q is an optionally substituted, optionally metallised 1,8-dihydroxynaphthyl group of Formula (4);

L is a divalent organic linker group; and wherein each A and L independently carries 1 or 2 substituents, and with the proviso that at least one of the groups represented by T comprises a water-solubilising group.

3. A composition according to claim 2 which further comprises a pH buffer and the composition has a H of 4 to 8.

4. A composition according to claim 3 wherein the buffer is selected from the group consisting of (tris(hydroxymethyl)aminomethane), cationic aliphatic primary amines, zwitterionic amino acids, phosphate buffers, amino-hydroxyalkylsulfonic acid zwitterions and trishydroxymethylaminomethane derivatives.

5. A composition according to claim 2 wherein the liquid medium further comprises an oxidant.

6. A process for the preparation of a compound of Formula (1):

T-Q-N═N-L-T  Formula (1)

wherein:

each T independently is an azo group of the formula A-N═N— wherein each A independently is an optionally substiuted aryl, heteroaryl, non-aromatic heterocyclic or an alkenyl group;

Q is an optionally substituted, optionally metallised 1,8-dihydroxynaphthyl group of Formula (4);

L is a divalent organic linker group; and wherein each A and L independently carries 1 or 2 substituents;

which process comprises diazotising an amine and coupling the resultant diazonium salt with a compound of formula T-Q-N═N-LH, wherein T, L and Q are each independently as defined in Formula (1), and with the proviso that at least one of the groups represented by T comprises a water-solubilising group.

7. A process for the preparation of Formula (1):

T-Q-N═N-L-T  Formula (1)

wherein:

each T independently is an azo group of the formula A-N═N— wherein each A independently is an optionally substiuted aryl, heteroaryl, non-aromatic heterocyclic or an alkenyl group;

Q is an optionally substituted, optionally metallised 1,8-dihydroxynaphthyl group of Formula (4);

L is a divalent organic linker group; and wherein each A and L independently carries 1 or 2 substituents;

which comprises the reaction of a compound of formula T-X—N═N-L-T with a strong base thereby forming a compound of Formula (1), wherein each T independently and L are as defined in Formula (1) and X is an optionally substituted 1-hydroxy-8-amino-naphthylene group, and with the proviso that at least one of the groups represented by T comprises a water-solubilising group.

8. A compound of Formula (1):

T-Q-N═N-L-T  Formula (1)

wherein:

each T independently is an azo group of the formula A-N═N— wherein each A independently is an optionally substiuted aryl, heteroaryl, non-aromatic heterocyclic or an alkenyl group;

Q is an optionally substituted, optionally metallised 1,8-dihydroxynaphthyl group of Formula (4);

L is a divalent organic linker group; and wherein each A and L independently carries 1 or 2 substituents; and with the proviso that at least one of the groups represented by T comprises a water-solubilising group.

9. A compound according to claim 8 wherein at least one group represented by A carries at least one sulpho group.

10. A compound according to claim 8 wherein at both groups represented by A carry at least one sulpho group.

11. A compound according to any one of claim 8 or 9 wherein L is of Formula (7):

-L 1 (-G-L 2 ) x -  Formula (7)

wherein:

L 1 is a single covalent bond or optionally substituted phenyl or naphthyl;

L 2 is optionally substituted phenyl or naphthyl;

G is —O—, —NR 2 —, —N═N—, —NR 2 —CO—, —NR 2 CONR 2 —, —S—, —SO—, —SO 2 —, —SO 2 NR 2 — or —CR 2 ═CR 2 —, wherein each R 2 independently is H or C 1-4 -alkyl; and

X is 0, 1 or 2.

12. A compound according to claim 8 wherein:

each A independently is optionally substituted phenyl, naphthyl, pyridyl or pyrazolyl;

Q is of Formula (5) or (6) or a metal complex thereof:

L is of Formula (7):

-L 1 (-G-L 2 ) x -  Formula (7)

wherein;

L 1 is a single covalent bond or optionally substituted phenyl or naphthyl;

L 2 is optionally substituted phenyl or naphthyl;

G is —O—, —NR 2 —, —N═N—, —NR 2 —CO—, —NR 2 CONR 2 —, —S—, —SO—, —SO 2 —, —SO 2 NR 2 — or —CR 2 ═CR 2 —, wherein each R 2 independently is H or C 1-4 -alkyl; and

X is 0, 1 or 2.

13. A compound according to claim 8 or 12 wherein said optional substituents which may be present on A and L are selected from the group consisting of OH, SO 3 H, PO 3 H 2 , CO 2 H, NO 2 , NH 2 , optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amine, optionally substituted acylamine and optionally substituted azo.

14. A compound according to claim 8 or 12 wherein said optional substituents which may be present on A and L are selected from the group consisting of OH; SO 3 H; PO 3 H 2 ; CO 2 H; NO 2 ; NH 2 ; C 1-4 -alkyl optionally carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group; C 1-4 -alkoxy optionally carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, C 1-4 alkyl, amino or hydroxy group; N carrying one or two C 1-4 -alkyl groups optionally carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group; C 1-4 -acylamino; and phenylazo, naphthylazo and heteroarylazo where the phenyl, naphthyl and heteroaryl units are optionally further substituted with one or more groups selected from the group consisting of OH, SO 3 H, PO 3 H 2 , CO 2 H, NO 2 and NH 2 , and azo groups containing a substituent of Formula (2):

wherein

Y is an electron withdrawing group;

Y 1 is H, alkyl or aryl, OR or N(R) 2 in which each R independently is H, optionally substituted alkyl or optionally substituted aryl; or,

Y and Y 1 together with the double bond shown above form a 5- or 6-membered ring; and

X 1 comprises at least one heteroatom selected from the group consisting of N, O and S.

15. A compound according to claim 8 of Formula (8) or a salt thereof:

16. A compound according to claim 8 of Formula (9) or a salt thereof:

17. A paper, an overhead projector slide or a textile material printed by means of a process according to claim 1 .

18. A paper, an overhead projector slide or a textile material printed with a compound according to claim 8 .

19. An ink jet printer cartridge, optionally refillable, comprising one or more chambers and a composition, wherein the composition is present in at least one of the chambers and the composition is as defined in claim 2 .

20. An ink set comprising a black ink, a magenta ink, a cyan ink an a yellow ink, wherein the black ink comprises a compound according to claim 8 or 15 .

21. An ink set comprising a black ink, a magenta ink, a cyan ink and a yellow ink, wherein the black ink comprises a composition according to claim 2 .

22. A compound according to claim 12 wherein said substituents which may be present on A and L 1 and L 2 are selected from the group consisting of OH, SO 3 H, PO 3 H 2 , CO 2 H, NO 2 , NH 2 , optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amine, optionally substituted acylamine and optionally substituted azo.

23. A compound according to claim 12 wherein said optional substituents which may be present on A and L 1 and L 2 are selected from the group consisting of OH; SO 3 H; PO 3 H 2 ; CO 2 H; NO 2 ; NH 2 ; C 1-4 -alkyl optionally carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group; C 1-4 -alkoxy optionally carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, C 1-4 alkyl, amino or hydroxy group; N carrying one or two C 1-4 -alkyl groups optionally carrying a sulpho, carboxy, phosphato, C 1-4 -alkoxy, amino or hydroxy group; C 1-4 -acylamino; and phenylazo, naphthylazo and heteroarylazo where the phenyl, naphthyl and heteroaryl units are optionally further substituted with one or more groups selected from OH, SO 3 H, PO 3 H 2 , CO 2 H, NO 2 and NH 2 , and azo groups containing a substituent of Formula (2):

wherein

Y is an electron withdrawing group;

Y 1 is H, alkyl or aryl, OR or N(R) 2 in which each R independently is H, optionally substituted alkyl or optionally substituted aryl; or,

Y and Y 1 together with the double bond shown above form a 5- or 6-membered ring; and

X 1 comprises at least one heteroatom selected from the group consisting of N, O and S.

24. A compound according to claim 8 wherein L carries at least one substituent of the formula —O—(CH 2 ) 1-4 OH or carries at least one sulpho group.