Ink composition containing a particular type of dye, and corresponding ink-jet printing process
View Patent ↗An ink composition is disclosed which contains at least one novel dye (CU) n (SAU) m that is capable of self-assembling under appropriate conditions to form supramolecular structures. More than one novel dye (CU) n (SAU) m and/or at least one non-colored self-assembling compound (SAU′) p (X) q may be incorporated in these supramolecular structures. Also disclosed is an ink-jet printing process using these novel dyes, and an ink-jet printing apparatus provided with an ink cartridge containing such a dye.
1. An ink composition comprising at least one self-assembling dye according to formula (I)
(CU) n (SAU) m (I)
wherein,
CU means a chromophore group with an absorption maximum between 200 nm and 2000 nm and covalently linked to SAU;
Sau means a multiple H-donor/accepting group, which can form at least three hydrogen bonds;
n and m are at least 1;
when n is greater than 1 the individual CU groups may be the same or different; and
when m is greater than 1 the individual SAU groups may be the same or different.
2. Ink composition according to claim 1 , wherein said ink composition further contains at least one self-assembling non-dye compound according to formula (II):
(SAU′) p (X) q (II)
wherein, SAU′ means a multiple H-donor/accepting group covalently linked to X;
X represents hydrogen, a halogen, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted sulphoxy group, a substituted or unsubstituted sulphone group, a substituted or unsubstituted amino group, a nitrile group, a substituted or unsubstituted, saturated or unsaturated alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulphonyl group, a substituted or unsubstituted phosphoryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group or a heterocyclic group;
p and p are at least 1;
q is 0 or 1;
when p is greater than 1 the SAU′ groups may be the same or different.
3. Ink composition according to claim 2 , wherein said at least one of said self-assembling dyes present in said ink composition is capable of self-assembling with at least one of said self-assembling non-dye compounds according to formula (II) present in said ink composition.
4. Ink composition according to claim 1 , wherein said ink composition contains at least two self-assembling dyes according to formula (I).
5. Ink composition according to claim 4 , wherein said at least two self-assembling dyes according to formula (I) are capable of self-assembling with one another.
6. Ink composition according to claim 1 , wherein the association constant K ass Of the self-assembling reaction between individual self-assembling dyes according to formula (I), determined by 1 H-NMR in CDCl 3 , is at least 2.5 M −1 .
7. An ink composition according to claim 3 , wherein the association constant K ass of the self-assembling reaction between said at least one of said self-assembling dyes present in said ink composition with at least one of said self-assembling non-dye compounds according to formula (II) present in said ink composition, determined by 1 H-NMR in CDCl 3 , is at least 2.5 M −1 .
8. Ink composition according to claim 5 , wherein the association constant K ass of the self-assembling reaction between the two self-assembling dyes according to formula (I), determined by 1 H-NMR in CDCl 3 , is at least 2.5 M −1 .
9. Ink composition according to claim 1 wherein said SAU group is or said SAU groups are independently selected from the group consisting of ureidopyrimidone groups, aminopyrimidine groups, aminopyridine groups, imide groups, aminotriazine groups, barbituric acid groups, urea based groups and uric acid based groups.
10. Ink composition according to claim 2 wherein said SAU′ group is or said SAU′ groups are independently chosen from the group consisting of ureidopyrimidone groups, aminopyrimidine groups, aminopyridine groups, imide groups, aminotriazine groups, barbituric acid groups, urea based groups and uric acid based groups.
11. Ink composition according to claim 1 wherein said ink composition is water based.
12. Ink composition according to claim 1 wherein said ink composition is solvent based.
13. Ink composition according to claim 1 wherein said ink composition is oil based.
14. Ink composition according to claim 1 wherein said ink composition is a hot melt ink.
15. Ink composition according to claim 1 wherein said ink composition is UV-curable.
16. Ink composition according to claim 6 wherein said association constant K ass is at least 10 2 M −1 .
17. Ink composition according to claim 6 wherein said association constant K ass is at least 10 5 M −1 .
18. Ink composition according to claim 7 wherein said association constant K ass is at least 10 2 M −1 .
19. Ink composition according to claim 7 wherein said association constant K ass is at least 10 5 M −1 .
20. Ink composition according to claim 8 wherein said association constant K ass is at least 10 2 M −1 .
21. Ink composition according to claim 8 wherein said association constant K ass is at least 10 5 M −1 .
22. Ink composition according to claim 1 wherein the concentration of self-assembling dye according to formula (I) is comprised between 0.5 wt % and 40 wt % based on the total ink weight.
23. Ink composition according to claim 11 wherein said concentration of self-assembling dye according to formula (I) is comprised between 1 wt % and 10 wt % based on the total ink weight.
24. A process for the formation of an ink-jet image comprising the step of image-wise jetting by means of an ink-jet printing apparatus onto an ink-jet recording element, comprising a support and optionally at least one ink receiving layer an ink composition comprising at least one self-assembling dye according to formula (I)
(CU) n (SAU) m (I)
wherein,
CU means a chromophore group with an absorption maximum between 200 nm and 2000 nm and covalently linked to SAU;
SAU means a multiple H-donor/accepting group, which can form at least three hydrogen bonds;
n and m are at least 1;
when n is greater than 1 the individual CU groups may be the same or different; and
when m is greater than 1 the individual SAU groups may be the same or different.
25. Process for the formation of an ink-jet image according to claim 24 , wherein said ink composition further comprises a self-assembling compound according to formula (II)
(SAU′) p (X) q (II)
wherein,
SAU′ means a multiple H-donor/accepting group, which can form at least three hydrogen bonds, and covalently linked to X;
X represents hydrogen, a halogen, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted sulphoxy group, a substituted or unsubstituted sulphone group, a substituted or unsubstituted amino group, a nitrile group, a substituted or unsubstituted, saturated or unsaturated alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulphonyl group, a substituted or unsubstituted phosphoryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group or a heterocyclic group;
p and p are at least 1;
q is 0 or 1;
when p is greater than 1 the SAU′ groups may be the same or different.
26. Process for the formation of an ink-jet image according to claim 25 , wherein said at least one of said self-assembling dyes present in said ink composition is capable of self-assembling with at least one of said self-assembling non-dye compounds according to formula (II) present in said ink composition.
27. Process for the formation of an ink-jet image according to claim 24 , wherein said ink composition comprises at least two self-assembling dyes according to formula (I).
28. Process for the formation of an ink-jet image according to claim 27 , wherein said at least two self-assembling dyes according to formula (I) are capable of self-assembling with one another.
29. Process for the formation of an ink-jet image according to claim 24 , wherein the association constant K ass of the self-assembling reaction between individual self-assembling dyes according to formula (I), determined by 1 H-NMR in CDCl 3 , is at least 2.5 M −1 .
30. Process for the formation of an ink-jet image according to claim 26 , wherein the association constant K ass of the self-assembling reaction between said at least one of said self-assembling dyes present in said ink composition with at least one of said self-assembling non-dye compounds according to formula (II) present in said ink composition, determined by 1 H-NMR in CDCl 3 , is at least 2.5 M −1 .
31. Process for the formation of an ink-jet image according to claim 28 , wherein the association constant K ass of the self-assembling reaction between the two self-assembling dyes according to formula (I), determined by 1 H-NMR in CDCl 3 , is at least 2.5 M −1 .
32. Process for the formation of an ink-jet image according to claim 24 , wherein said SAU group is or said SAU groups are independently selected from the group consisting of ureidopyrimidone groups, aminopyrimidine groups, aminopyridine groups, imide groups, aminotriazine groups, barbituric acid groups, urea based groups and uric acid based groups.
33. Process for the formation of an ink-jet image according to claim 25 , wherein said SAU′ group is or said SAU′ groups are independently chosen from the group consisting of ureidopyrimidone groups, aminopyrimidine groups, aminopyridine groups, imide groups, aminotriazine groups, barbituric acid groups, urea based groups and uric acid based groups.
34. Process for the formation of an ink-jet image according to claim 24 , wherein said ink composition is water based.
35. Process for the formation of an ink-jet image according to claim 24 , wherein said ink composition is solvent based.
36. Process for the formation of an ink-jet image according to claim 24 , wherein said ink composition is oil based.
37. Process for the formation of an ink-jet image according to claim 24 , wherein said ink composition is a hot melt ink.
38. Process for the formation of an ink-jet image according to claim 24 , wherein said ink composition is UV-curable.
39. Process for the formation of an ink-jet image according to claim 29 , wherein said association constant K ass is at least 10 2 M −1 .
40. Process for the formation of an ink-jet image according to claim 29 , wherein said association constant K ass is at least 10 5 M −1 .
41. Process for the formation of an ink-jet image according to claim 30 , wherein said association constant K ass is at least 10 2 M −1 .
42. Process for the formation of an ink-jet image according to claim 30 , wherein said association constant K ass is at least 10 5 M −1 .
43. Process for the formation of an ink-jet image according to claim 31 , wherein said association constant K ass is at least 10 2 M −1 .
44. Process for the formation of an ink-jet image according to claim 31 , wherein said association constant K ass is at least 10 5 M −1 .
45. Process for the formation of an ink-jet image according to claim 24 , wherein the concentration of self-assembling dye according to formula (I) is comprised between 0.5 wt % and 40 wt % based on the total ink weight.
46. Process for the formation of an ink-jet image according to claim 34 , wherein said concentration of self-assembling dye according to formula (I) is comprised between 1 wt % and 10 wt % based on the total ink weight.
47. An ink-jet printing apparatus comprising an ink cartridge containing an ink composition comprising at least one self-assembling dye according to formula (I)
(CU) n (SAU) m (I)
wherein,
CU means a chromophore group with an absorption maximum between 200 nm and 2000 nm and covalently linked to SAU;
SAU means a multiple H-donor/accepting group, which can form at least three hydrogen bonds;
n and m are at least 1;
when n is greater than 1 the CU groups may be the same or different; and
when m is greater than 1 the SAU groups may be the same or different.
48. Ink composition according to claim 1 wherein said at least one self-assembling dye is a dye according to formula (III):
wherein
Linker represents any linking group containing at least one carbon, silicon, nitrogen, phosphorous, sulfur or oxygen atom;
CU means any dye chosen from the group consisting of an azo dye with a molar extinction coefficient larger than 10 3 l mol −1 cm −1 , an anthraquinone dye, a (poly)methine dye, an azomethine dye, a disazo dye, a carbonium dye, a styryl dye, a stilbene dye, a phthalocyanine dye, a coumarin dye, an aryl-carbonium dye, a nitro dye, a naphtholactam dye, a dioxazine dye, a flavin dye and a formazan dye;
n and o are the same or different and are integers having a value of at least 1; m can be zero or any integer having a value of at least 1;
R 1 and R 2 are the same or different and represent hydrogen, a halogen, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted sulphoxy group, a substituted or unsubstituted sulphone group, a substituted or unsubstituted amino group, a nitrile group, a substituted or unsubstituted, saturated or unsaturated alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulphonyl group, a substituted or unsubstituted phosphoryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a heterocyclic group, a chromophore group, or R 1 and R 2 represent the necessary atoms to form a ring system.
49. Ink composition according to claim 48 wherein said Linker is selected from the group consisting of a substituted or unsubstituted, saturated or unsaturated aliphatic group, a substituted or unsubstituted alicyclic hydrocarbon group, a substituted or unsubstituted aromatic group and a substituted or unsubstituted heteroaromatic group.