IP Library Granted Patent US 6,969,421
Granted Patent B2
US 6,969,421 · App. 10/441,278 · Granted Nov 29, 2005

Processes, compositions and compounds

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Quick Facts
Patent No.
US 6,969,421
App. No.
10/441,278
Granted
Nov 29, 2005
Kind
B2
Abstract

A process for printing an image on a substrate comprising applying thereto by means of an ink jet printer an ink containing a metal chelate compound of the Formula (1) and salts thereof: wherein: one of A and B is OH and the other is an azotriazole group; each W independently is a carboxy or carbonamido group; each X independently is a substituent other than H, sulphonamido, carboxy, sulpho and carbonamido; J is a sulphonamido group; M is a metal or boron; a, p, q and n are each independently 0, 1, 2, 3 or 4; and (p+q+a+n) is 0, 1, 2, 3 or 4. Also claimed are compounds of Formula (1), compositions and inks containing a compound of Formula (1) and an ink jet printer cartridge containing the ink.

Claims (65)

1. A process for printing an image on a substrate comprising applying thereto by means of an ink jet printer an ink containing a metal chelate compound of Formula (1a) or a salt thereof:

wherein:

n and a are each independently 0,1, 2, 3 or 4;

q is 1, 2, 3 or 4;

(a+q+n) is 1, 2, 3 or 4;

one of A and B is OH and the other is an azotriazole group

each X independently is a substituent other than H, sulphonamido, carboxy, sulpho and carbonamido;

J is a sulphonamido group;

M is a metal or boron.

2. A process claim 1 wherein the azotriazole group is of the Formula (2a), (2b), (2c), (2d) or (2e):

wherein:

Z is H, —OH, —Br, —Cl, —F, —CN, —NO 2 , —PO 3 H 2 , —SO 3 H, —CO 2 H, optionally substituted phosphoramide, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aralkyl, —SR 1 , —SO 2 R 1 , —SO 2 NR 2 R 3 , —SOR 1 , —OR 1 , —C(O)R 1 , —C(O)OR 1 , —C(O)NR 2 R 3 , —NR 2 R 3 , —NHCOR 1 ; and

Y is CF 3 or any one of the groups defined for Z; and

wherein:

R 1 , R 2 and R 3 are each independently H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted aralkyl; or

R 2 and R 3 together with the nitrogen to which they are attached form an optionally substituted 5- or 6-membered ring.

3. A process according to claim 1 wherein M is nickel.

4. A process according to claim 2 wherein Z is H and Y is CO 2 H or H.

5. A process according to claim 2 wherein Z is H, Y is CO 2 H or H and M is nickel.

6. A compound of Formula (1a) or a salt thereof:

wherein:

n and a are each independently 0, 1, 2, 3 or4;

q is 1, 2, 3 or 4;

(a+q+n) is 1, 2, 3 or4;

one of A and B is OH and the other is an azotriazole group

each X independently is a substituent other than H, sulphonamido, carboxy, sulpho and carbonamido;

J is a sulphonamido group;

M is a metal or boron.

7. A compound according to claim 6 wherein the azotriazole group is of the Formula (2a), (2b), (2c), (2d) or (2e):

wherein Z is H and Y is CO 2 H or H.

8. A compound according to claim 6 wherein M is nickel.

9. An ink comprising:

(a) a compound according to any one of claims 6 , 7 or 8 and

(b) a liquid medium.

10. An ink according to claim 9 wherein the liquid medium comprises a surfactant and a mixture of water and an organic solvent.

11. A substrate printed with an ink according to claim 9 .

12. A substrate printed with an ink according to claim 10 .

13. An ink jet printer cartridge comprising a chamber and ink, wherein the ink is as defined in claim 9 .

14. An ink jet printer containing an ink jet printer cartridge, wherein the ink jet printer cartridge is as defined n claim 13 .

15. A process according to claim 1 wherein n is 0.

16. A process according to claim 1 wherein a is 0.

17. A process according to claim 1 wherein q is 1 or 2.

18. A process according to claim 1 wherein the compound of Formula (1a) is a metal chelate compound of he Formula (1a-3) or (1a-4) or a salt thereof:

wherein:

D is an azotriazole group;

J is a sulphonamido group; and

M is a metal or boron.

19. A process according to claim 1 or claim 18 where J is SO 2 NR 6 R 7 wherein one of R 6 or R 7 is H and the other is optionally substituted aryl.

20. A process according to claim 19 where one of R 6 or R 7 is H and the other is an aryl group carrying a carboxy group.

21. A process according to claim 19 where one of R 6 or R 7 is H and the other is a carboxy phenyl group.

22. A process according to claim 1 or claim 18 where the compound of Formula (1a) is

wherein M is nickel.

23. A compound according to claim 6 wherein n is 0.

24. A compound according to claim 6 wherein a is 0.

25. A compound according to claim 6 wherein q is 1 or 2.

26. A compound according to claim 6 wherein the compound of Formula (1a) is a metal chelate compound of the Formula (1a-3) or (1a-4) or a salt thereof:

wherein:

D is an azotriazole group;

J is a sulphonamido group; and

M is a metal or boron.

27. A compound according to claim 6 or claim 26 where J is SO 2 NR 6 R 7 wherein one of R 6 or R 7 is H and the other is optionally substituted aryl.

28. A compound according to claim 27 where one of R 6 or R 7 is H and the other is an aryl group carrying a carboxy group.

29. A compound according to claim 27 where one of R 6 or R 7 is H and the other is a carboxy phenyl group.

30. A compound according to claim 6 or claim 26 of Formula:

wherein M is nickel.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2006
From: AVECIA LIMITED
To: AVECIA INKJET LIMITED
Reel/Frame 018132/0554 →
CHANGE OF NAME Recorded Aug 17, 2006
From: AVECIA INKJET LIMITED
To: FUJIFILM IMAGING COLORANTS LIMITED
Reel/Frame 018132/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 14, 2003
From: WRIGHT, GAVIN; JOHNSON, KEVIN; RAGGATT, MAIRI ELIZABETH; PATEL, PRAKASH
To: AVECIA LIMITED
Reel/Frame 014389/0481 →