Ink, ink jet recording method and azo compound

• US 6,878,196 B2
• Filed: 01/15/2003
• Issued: 04/12/2005
• Est. Priority Date: 01/15/2002
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Harada, Toru, Iwanaga, Hiroshi, Ogawa, Manabu, Yabuki, Yoshiharu
• Primary Examiner(s): Klemanski, Helene
• Application Number:
  US10/342,177
• Publication Number:
  US 20030213405A1
• Time in Patent Office: 818 Days
• Field of Search: 106/31.48, 106/31.5, 534/755, 534/757, 534/753, 534/775, 534/774, 534/765, 534/766, 534/767, 534/769, 347/100
• US Class Current: 106/31.48
• CPC Class Codes: C09B 29/0037 containing a five-membered heterocyclic ring with two nitrogen atoms
• CPC Class Codes: C09B 29/0092 containing a five-membered heterocyclic ring with two nitrogen and one sulfur as heteroatoms
• CPC Class Codes: C09B 29/3656 containing amino-1,2-diazoles
• CPC Class Codes: C09B 33/12 in which the coupling component is a heterocyclic compound
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

An ink containing at least one dye represented by formula (1):
wherein R¹, R² and R³ are each independently a hydrogen atom or a monovalent group; Z is a nitrogen atom, or a carbon atom to which a hydrogen atom or a monovalent group is bonded; and at least one of R¹, R², R³, and the monovalent group that Z has is a substituent having a heterocyclic group substituted with an azo group.

Claims

1. An ink, comprising at least one dye represented by formula (1):

wherein R¹, R² and R³ are each independently a hydrogen atom or a monovalent aroun;

Z is a nitrogen atom, or a carbon atom to which a hydrogen atom or a monovalent group is bonded; and

at least one of R¹, R², R³, and the monovalent group that Z has is a substituent having a heterocyclic group substituted with an azo group, wherein, in formula (1), at least two of R¹, R² and R³ each represent a substituent having a heterocyclic group substituted with an azo group.

2. An ink, comprising at least one dye represented by formula (3):

wherein R¹⁰ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group;

R¹¹ is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group;

Het is an aromatic heterocyclic group; and

R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group, a heterocyclic group, or a group represented by formula (3-1);

wherein, in formula (3-1), R^10a is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group; and

Het is an aromatic heterocyclic group;

in the formula (3), each group on the dye may have a substituent.

3. The ink according to claim 2, wherein, in formula (3), R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group.

4. The ink according to claim 2, wherein, in formula (3), R¹² is a group represented by the formula (3-1).

5. An ink-jet-recording method, comprising the step of:

forming an image with an ink on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support,

wherein the ink comprises at least one dye represented by formula (1);

wherein, in formula (1), R¹, R² and R³ are each independently a hydrogen atom or a monovalent group;

Z is a nitrogen atom, or a carbon atom to which a hydrogen atom or a monovalent group is bonded; and

at least one of R¹, R², R³, and the monovalent group that Z has is a substituent having a heterocyclic group substituted with an azo group, wherein, in formula (1), at least two of R¹, R² and R³ each represent a substituent having a heterocyclic group substituted with an azo group.

6. An ink-jet-recording method, comprising the step of:

forming an image with an ink on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support,

wherein the ink comprises at least one dye represented by formula (3);

wherein R¹⁰ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group;

R¹¹ is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group;

Het is an aromatic heterocyclic group; and

R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group, a heterocyclic group, or a group represented by formula (3-1);

wherein, in formula (3-1), R^10a is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group; and

Het is an aromatic heterocyclic group;

in the formula (3), each group on the dye may have a substituent.

7. The ink-jet-recording method according to claim 6, wherein, in formula (3), R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group.

8. The ink-jet-recording method according to claim 6, wherein, in formula (3), R¹² is a group represented by the formula (3-1).

9. A compound represented by formula (3):

wherein R¹⁰ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group;

R¹¹ is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group;

Het is an aromatic heterocyclic group; and

R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group, a heterocyclic group, or a group represented by formula (3-1);

wherein, in formula (3-1), R^10a is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group; and

Het is an aromatic heterocyclic group;

in the formula (3), each group on the compound may have a substituent.

10. The compound according to claim 9, wherein, in formula (3), R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group.

11. The compound according to claim 9, wherein, in formula (3). R¹² is a group represented by the formula (3-1).

12. The compound according to claim 9, which is represented by formula (4):

wherein R¹⁰ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group;

R¹¹ is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group;

one of X and Y is a nitrogen atom and the other is a —

C(—

R¹³)═

group;

R¹³ is a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkylthio group, an alkylsulfonyl group, an alkylsulfinyl group, an alkyloxycarbonyl group, a carbamoyl group, an alkoxy group, an aryl group, an arylthio group, an arylsulfonyl group, an arylsulfinyl group, an aryloxy group or an acylamino group; and

R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group, a heterocyclic group, or a group represented by formula (4-1);

wherein, in formula (4-1), R^10a is a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkoxy group or an aryl group; and

X and Y have the same meanings as those in formula (4); and

in the formula (4), each group on the compound may have a substituent.

13. The compound according to claim 12, wherein, in formula (4), R¹² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an amino group, a sulfo group or a heterocyclic group.

14. The compound according to claim 12, wherein, in formula (4), R¹² is a group represented by the formula (4-1).