Ink-jet ink and ink jet recording method

• US 6,645,281 B2
• Filed: 03/30/2001
• Issued: 11/11/2003
• Est. Priority Date: 03/30/2000
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Tateishi, Keiichi, Noro, Masaki, Yabuki, Yoshiharu
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US09/820,746
• Publication Number:
  US 20020067399A1
• Time in Patent Office: 956 Days
• Field of Search: 106/31.27, 106/31.25, 106/31.43, 106/31.47, 106/31.49
• US Class Current: 106/31.27
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

An ink-jet ink which includes a coloring composition containing oil-soluble dye aggregates is provided. The oil-soluble dye which forms aggregates is preferred a compound represented in the following general formula (1):

D-(Y)_n  General Formula (1)

wherein, D represents a dye portion having a chromophore;

Y represents a polar group which is connected to D directly or via a bivalent connecting group and which generates interaction between the compounds represented in said general formula (1); and

n represents any integer of 2 to 10.

Claims

1. An ink-jet ink which includes a coloring composition containing oil-soluble dye aggregates formed from two or more dye molecules.

2. An ink-jet ink according to claim 1, wherein an oil-soluble dye which forms aggregates is a compound represented in the following general formula (1):

3. An ink-jet ink according to claim 2, wherein Y in said general formula (1) is at least one which is selected from the group consisting —

CO₂H, —

CONHR, —

SO₂NHR, —

NHCONHR, —

OCONHR, —

NHCOR, —

NHSO₂R, —

NHCOOR, —

CONHCOR, —

CONHSO₂R wherein R represents one of a hydrogen atom, an alkyl group, an aryl group, and a heterocyclic group, and —

CN.

4. An ink-jet ink according to claim 2, wherein D in said general formula (1) is a compound represented in the following general formula (2):

wherein, X represents the residue of a color coupler;

A represents one of —

NR⁴R⁵ and a hydroxyl group;

R⁴ and R⁵ represent respectively independently one of a hydrogen atom, an aliphatic group, an aromatic group, and a heterocyclic group;

B¹ represents one of ═

C(R⁶)— and

═

N—

;

B² represents one of —

C(R⁷)═ and

—

N═

;

R², R³, R⁶, and R⁷ represent respectively independently one of a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR⁵¹, —

SR⁵², —

CO₂R⁵³, —

OCOR⁵⁴, —

R⁵⁵R⁵⁶ CNR⁵⁷R⁵⁸, —

SO₂R⁵⁹, —

SO₂NR⁶⁰R⁶¹, —

NR⁶²CONR⁶³R⁶⁴, —

NR⁶⁵CO₂R⁶⁶, —

COR⁶⁷, —

NR⁶⁸COR⁶⁹, and —

NR⁷⁰SO₂R⁷¹; and

R⁵¹, R⁵² R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷, R⁵⁸, R⁵⁹, R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵, R⁶⁶, R⁶⁷, R⁶⁸, R⁶⁹, R⁷⁰, and R⁷¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group.

5. An ink-jet ink according to claim 2, wherein D in said general formula (1) is a phthalocyanine.

6. An inkjet ink according to claim 1, wherein content of said oil-soluble dye aggregates in the coloring composition is from 0.5 to 30% by mass.

7. An ink-jet ink according to claim 1, wherein the oil-soluble dye aggregates are dispersed in a water-based medium.

8. An ink-jet ink according to claim 7, wherein the oil-soluble dye is aggregated in a high boiling point organic solvent having a boiling point of 150°

C. or more and a specific inductive capacity at 25°

C. of 3 to 12, and the oil-soluble dye is dispersed in the water-based medium.

9. An ink-jet ink according to claim 8, wherein content of said high boiling point organic solvent in the coloring composition is from 1 to 1000 mass parts, relative to 100 mass parts of the oil-soluble dye aggregates.

10. An ink-jet ink according to claim 7, wherein coloring particulates which contain the oil-soluble dye aggregates and an oil-soluble polymer are dispersed in the water-based medium.

11. An ink-jet ink according to claim 10, wherein content of said oil-soluble polymer in the coloring composition is from 10 to 1000 mass parts, relative to 100 mass parts of the oil-soluble dye aggregates.

12. An ink-jet ink according to claim 10, wherein said coloring composition contains a high boiling point organic solvent.

13. An ink-jet ink according to claim 10, wherein said coloring particulates are formed by dispersing the oil-soluble dye aggregates in the oil-soluble polymer.

14. An ink-jet ink according to claim 1, wherein the oil-soluble dye aggregates are J aggregates or H aggregates.

15. An ink jet recording method, comprising jetting an ink-jet ink which includes a coloring composition containing oil-soluble dye aggregates formed from two or more dye molecules to record an image.

16. An ink jet recording method according to claim 15, wherein an oil-soluble dye which forms aggregates is a compound represented in the following general formula (1):

17. An ink jet recording method according to claim 15, wherein Y in said general formula (1) is at least one which is selected from a group formed by —

CO₂H, —

CONHR, —

SO₂NHR, —

NHCONHR, —

OCONHR, —

NHCOR, —

NHSO₂R, —

NHCOOR, —

CONHCOR, —

CONHSO₂R (R represents one of a hydrogen atom, an alkyl group, an aryl group, and a heterocyclic group), and —

CN.

18. An ink jet recording method according to claim 16, wherein D in said general formula (1) is a compound represented in the following general formula (2):

wherein, X represents the residue of a color coupler;

A represents one of —

NR⁴R⁵ and a hydroxyl group;

R⁴ and R⁵ represent respectively independently one of a hydrogen atom, an aliphatic group, an aromatic group, and a heterocyclic group;

B¹ represents one of ═

C(R⁶)— and

═

N—

;

B²represents one of —

C(R⁷)═ and

—

N═

;

R², R³, R⁶, and R⁷ represent respectively independently one of a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR⁵¹, —

SR⁵², —

CO₂R⁵³, —

OCOR⁵⁴, —

NR⁵⁵R⁵⁶, —

CONR⁵⁷R⁵⁸, —

SO₂R⁵⁹, —

SO₂NR⁶⁰R⁶¹, —

NR⁶²CONR⁶³R⁶⁴, —

NR⁶⁵CO₂R⁶⁶, —

COR⁶⁷, —

NR⁶⁸COR⁶⁹, and —

NR⁷⁰SO₂R⁷¹; and

R⁵¹, R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷, R⁵⁸, R⁵⁹, R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵, R⁶⁶, R⁶⁷, R⁶⁸, R⁶⁹, R⁷⁰, and R⁷¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group.

19. An ink jet recording method according to claim 16, wherein D in said general formula (1) is a phthalocyanine.

20. An ink jet recording method according to claim 15, wherein the oil-soluble dye aggregates are dispersed in a water-based medium.

21. An ink jet recording method according to claim 20, wherein the oil-soluble dye is aggregated in a high boiling point organic solvent having a boiling point of 150°

C. or more and a specific inductive capacity at 25°

C. of 3 to 12, and the oil-soluble dye is dispersed in the water-based medium.