Granted Patent B2

US 7,294,730 · App. 11/291,056 · Granted Nov 13, 2007

Abstract

Claims (50)

1. A colorant compound of the formula

wherein R 1 , R 2 , and R 3 each, independently of the others, is a hydrogen atom, an alkyl group, including linear and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, an arylalkyl group, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or an alkylaryl group, including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the alkylaryl group, provided that the total number of carbon atoms and heteroatoms, excluding atoms in any substituents, in R 1 +R 2 +R 3 is at least about 18, M is a metal atom, each A, each E, and each G, independently of the other, represents a substituent on a phenyl or pyrazolone ring, wherein G can also be a hydrogen atom, m is an integer of 0, 1, or 2, p is an integer of 0, 1, 2, 3, or 4, J represents (i) a hydrogen atom, (ii) an alkyl group (including linear and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group), (iii) an aryl group (including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group), (iv) an arylalkyl group (including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, saturated or unsaturated, and cyclic or acyclic, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group), or (v) an alkylaryl group (including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, saturated or unsaturated, and cyclic or acyclic, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the alkylaryl group), wherein two or more substituents on the phenyl or pyrazolone rings can be joined together to form a ring, and n represents an integer of 1, 2, or 3.

2. A colorant compound according to claim 1 of the formula

3. A colorant compound according to claim 1 of the formula

4. A colorant compound according to claim 1 wherein at least one of A, E, G, and J is an alkyl group, provided that when A is the at least one alkyl group, m is at least 1, and provided that when E is the at least one alkyl group, p is at least 1.

5. A colorant compound according to claim 4 wherein the alkyl group is a substituted alkyl group.

6. A colorant compound according to claim 4 wherein the alkyl group is an unsubstituted alkyl group.

7. A colorant compound according to claim 4 wherein the alkyl group contains at least one heteroatom therein.

8. A colorant compound according to claim 4 wherein the alkyl group contains no heteroatoms therein.

9. A colorant compound according to claim 1 wherein at least one of A, E, G, and J is an aryl group, provided that when A is the at least one aryl group, m is at least 1, and provided that when E is the at least one aryl group, p is at least 1.

10. A colorant compound according to claim 9 wherein the aryl group is a substituted aryl group.

11. A colorant compound according to claim 9 wherein the aryl group is an unsubstituted aryl group.

12. A colorant compound according to claim 9 wherein the aryl group contains at least one heteroatom therein.

13. A colorant compound according to claim 9 wherein the aryl group contains no heteroatoms therein.

14. A colorant compound according to claim 1 wherein at least one of A, E, G, and J is an arylalkyl or alkylaryl group, provided that when A is the at least one arylalkyl or alkylaryl group, m is at least 1, and provided that when E is the at least one arylalkyl or alkylaryl group, p is at least 1.

15. A colorant compound according to claim 14 wherein the arylalkyl or alkylaryl group is a substituted arylalkyl or alkylaryl group.

16. A colorant compound according to claim 14 wherein the arylalkyl or alkylaryl group is an unsubstituted arylalkyl or alkylaryl group.

17. A colorant compound according to claim 14 wherein the arylalkyl or alkylaryl group contains at least one heteroatom therein.

18. A colorant compound according to claim 14 wherein the arylalkyl or alkylaryl group contains no heteroatoms therein.

19. A colorant compound according to claim 1 wherein at least one of A, E, and G is a substituent selected from the group consisting of a hydroxy group, a halogen atom, an amine group, an imine group, an ammonium group, a cyano group, a pyridine group, a pyridinium group, an ether group, an aldehyde group, a ketone group, an ester group, an amide group, a carbonyl group, a thiocarbonyl group, a sulfate group, a sulfonate group, a sulfonic acid group, a sulfide group, a sulfoxide group, a phosphine group, a phosphonium group, a phosphate group, a nitrile group, a mercapto group, a nitro group, a nitroso group, a sulfone group, an acyl group, an azo group, a cyanato group, a carboxylate group, a carboxylic acid group, a urethane group, a urea group, or mixtures thereof, provided that when A is the at least one substituent, m is at least 1, and provided that when E is the at least one substituent, p is at least 1.

20. A colorant compound according to claim 1 wherein n is 1.

21. A colorant compound according to claim 1 wherein n is 2.

22. A colorant compound according to claim 1 wherein n is 3.

23. A colorant compound according to claim 1 wherein M is a metal in the Lanthanide Series.

24. A colorant compound according to claim 1 wherein M is chromium, iron, cobalt, molybdenum, tungsten, ruthenium, osmium, rhodium, iridium, manganese, rhenium, vanadium, niobium, tantalum, titanium, zirconium, hafnium, scandium, yttrium, lanthanum, zinc, or aluminum.

25. A colorant compound according to claim 1 wherein M is chromium, iron, cobalt.

26. A colorant compound according to claim 1 wherein M is chromium.

27. A colorant compound according to claim 1 of the formula

28. A colorant compound according to claim 1 of the formula

29. A colorant compound according to claim 1 wherein R 1 , R 2 , and R 3 each, independently of the others, are hydrogen atoms or alkyl groups, including linear and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, boron, and the like either may or may not be present in the alkyl group.

30. A colorant compound according to claim 29 wherein at least one of the alkyl groups is linear.

31. A colorant compound according to claim 29 wherein at least one of the alkyl groups is branched.

32. A colorant compound according to claim 29 wherein at least one of the alkyl groups is substituted.

33. A colorant compound according to claim 29 wherein at least one of the alkyl groups is unsubstituted.

34. A colorant compound according to claim 29 wherein at least one of the alkyl groups has hetero atoms therein.

35. A colorant compound according to claim 29 wherein at least one of the alkyl groups has no hetero atoms therein.

36. A colorant compound according to claim 29 wherein R 1 , R 2 , and R 3 are the same as each other.

37. A colorant compound according to claim 29 wherein at least two of R 1 , R 2 , and R 3 are different from each other.

38. A colorant compound according to claim 29 wherein all three of R 1 , R 2 , and R 3 are different from each other.

39. A colorant compound according to claim 29 wherein the compound is of the formula

40. A colorant compound according to claim 29 wherein the compound is of the formula

41. A colorant compound according to claim 29 wherein the compound is of the formula

42. A colorant compound according to claim 29 wherein the compound is of the formula

43. A colorant compound according to claim 29 wherein the compound is of the formula

44. A colorant compound according to claim 29 wherein the compound is of the formula

45. A colorant compound according to claim 1 wherein at least one of R 1 , R 2 , and R 3 is an aryl group, an arylalkyl group, or an alkylaryl group.

46. A colorant compound according to claim 45 wherein the aryl, arylalkyl, or alkylaryl group is substituted.

47. A colorant compound according to claim 45 wherein the aryl, arylalkyl, or alkylaryl group is unsubstituted.

48. A colorant compound according to claim 45 wherein the aryl, arylalkyl, or alkylaryl group contains at least one heteroatom therein.

49. A colorant compound according to claim 45 wherein the aryl, arylalkyl, or alkylaryl group contains no heteroatoms therein.

Assignments (9)