Coloring composition, ink for ink-jet, and ink-jet recording method

• US 20010023267A1
• Filed: 12/21/2000
• Published: 09/20/2001
• Est. Priority Date: 12/22/1999
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Kimura, Keizo, Yamada, Makoto, Ishizuka, Takahiro
• Granted Patent: US 6,756,423 B2
• Time in Patent Office: Days
• US Class Current: 524/86
• CPC Class Codes: C09B 55/009 Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
• CPC Class Codes: C09D 11/32 characterised by colouring agents

Abstract

The present invention related to an ink for ink-jet comprising: a coloring composition containing coloring particulates dispersed in a water based medium, the coloring particulates containing an oil soluble dye and an oil soluble polymer; and wherein the coloring composition has wavelength of maximum absorption (λ max(nm)) in the wavelength range from 510 to 560 nm and when the absorbance at the wavelength of maximum absorption (λ max(nm)) is regarded as 1, the absorbance at a wavelength (λ max+75 (nm)) is no more than 0.2 and the absorbance at a wavelength (λ max−75 (nm)) is no more than 0.4.

Claims

1. An ink for ink-jet comprising:

a coloring composition containing coloring particulates dispersed in a water based medium, the coloring particulates containing an oil soluble dye and an oil soluble polymer; and

wherein the coloring composition has wavelength of maximum absorption (λ

max(nm)) in the wavelength range from 510 to 560 nm and when the absorbance at the wavelength of maximum absorption (λ

max(nm)) is regarded as 1, the absorbance at a wavelength (λ

max+75 (nm)) is no more than 0.2 and the absorbance at a wavelength (λ

max−

75 (nm)) is no more than 0.4.

2. The ink for ink-jet according to

claim 1

, wherein the oil soluble dye is represented by the formula (I):

wherein R¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹, —

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²²CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R³¹; and

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³, R²⁴,R²⁵,R²⁶,R²⁷,R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

A represents —

NR⁴R⁵ or a hydroxyl group;

R⁴ and R⁵ each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group;

B¹ represents ═

C(R⁶)—

or ═

N—

;

B² represents —

C(R⁷)═

or —

N═

;

R²,R³,R⁶ and R⁷ each independently represents 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 or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵,R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹,R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷, R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R² and R³, R³ and R⁴, R⁴ and R⁵,R⁵ and R⁶, or R⁶ and R⁷ may be bonded to each other to form a ring;

C forms a 5- or 6-membered nitrogen-containing heterocycle, the heterocycle being substitutable with at least one substituent selected from an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR⁸¹, —

SR⁸²,—

CO₂R⁸³,—

OCOR⁸⁴,—

NR⁸⁵R⁸⁶,—

CONR⁸⁷R⁸⁸,—

SO₂R⁸⁹,SO₂NR⁹⁰R⁹¹,—

NR⁹²CONR⁹³R⁹⁴,—

NR⁹⁵CO₂R⁹⁶,—

COR⁹⁷,—

NR⁹⁸COR⁹⁹, and —

NR¹⁰⁰SO₂R¹⁰¹;

the substituent(s) may further have one or more substituents;

the nitrogen-containing heterocycle may be combined with another ring to form a condensed ring; and

R⁸¹,R⁸²,R⁸³,R⁸⁴,R⁸⁵,R⁸⁶,R⁸⁷,R⁸⁸,R⁸⁹,R⁹⁰,R⁹¹,R⁹²,R⁹³,R⁹⁴,R⁹⁵,R⁹⁶,R⁹⁷, R⁹⁸,R⁹⁹,R¹⁰⁰ and R¹⁰¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group.

3. The ink for ink-jet according to

claim 1

, wherein the oil soluble dye is represented by the following formula (II):

wherein R¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹,—

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²²CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R₃₁;

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³,R²⁴,R²⁵,R²⁶,R²⁷, R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

R²R³,R⁶ and R⁷ each independently represents 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,—

NR⁶⁵COR₂R⁶⁶,—

COR⁶⁷,—

NR⁶⁸COR⁶⁹ or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵, R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹,R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷,R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R⁴ and R⁵ each independently represents a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group; and

X and Y each represents —

C(R⁸)═

or —

N═

;

R⁸ is a hydrogen atom, an aliphatic group or an aromatic group;

either one of X and Y necessarily represents —

N═

, and X and Y do not represent —

N═

at the same time.

4. The ink for ink-jet according to

claim 3

, wherein X represents —

N═

, and Y represents —

C(R⁸)═

.

5. The ink for ink-jet according to

claim 1

, wherein in the coloring particulates, the oil soluble dye dispersed in the oil soluble polymer.

6. The ink for ink-jet according to

claim 1

, wherein the coloring particulates are obtained by emulsifying and making into fine particles an organic solvent which includes the oil soluble polymer and the oil soluble dye, by one of adding water to the organic solvent, and adding the organic solvent into water.

7. The ink for ink-jet according to

claim 1

, wherein the oil soluble polymer is a vinyl polymer.

8. The ink for ink-jet according to

claim 7

, wherein the vinyl polymer has at least one of a carboxyl groups and a sulfonic acid groups as an ionic groups.

9. The ink for ink-jet according to

claim 8

, wherein the ionic group of the vinyl polymer is a carboxyl group.

10. The ink for ink-jet according to

claim 7

, wherein the vinyl polymer has ionic groups in an amount of from 0.1 to 3.0 mmol/g.

11. An ink for ink-jet comprising:

a coloring composition containing coloring particulates dispersed in a water based medium, the coloring particulates containing an oil soluble dye represented by the following formula (I) and a vinyl polymer having at least one of carboxyl groups and sulfonic acid groups as ionic groups;

wherein R represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹,—

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²² CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R³¹; and

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³,R²⁴,R²⁵,R²⁶, R²⁷,R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

A represents —

NR⁴R⁵ or a hydroxyl group;

R⁴ and R⁵ each independently represents a hydrogen tom, an aliphatic group, an aromatic group or a heterocyclic group;

B¹ represents ═

C(R⁶)—

or ═

N—

;

B² represents —

C(R⁷)═

or —

N═

;

R²,R³, R⁶ and R⁷ each independently represents 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 or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵,R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹,R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷, R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R² and R³,R³ and R⁴, R⁴ and R⁵,R⁵ and R⁶, or R⁶, and R⁷ may be bonded to each other to form a ring;

C forms a 5- or 6-membered nitrogen-containing heterocycle;

this heterocycle may be substituted with at least one substituent selected from an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR⁸¹,—

SR⁸²,—

CO₂R⁸³,—

OCOR⁸⁴,—

NR⁸⁵R⁸⁶,—

CONR⁸⁷R⁸⁸,—

SO₂R⁸⁹,SO₂NR⁹⁰R⁹¹,—

NR⁹²CONR⁹³R⁹⁴,—

NR⁹⁵CO₂R⁹⁶,—

COR⁹⁷,—

NR⁹⁸COR⁹⁹, and —

NR¹⁰⁰SO₂R¹⁰¹;

the substituent(s) may further have one or more substituents;

the nitrogen-containing heterocycle may be combined with another ring to form a condensed ring; and

R⁸¹,R⁸²,R⁸³,R⁸⁴,R⁸⁵,R⁸⁶,R⁸⁷,R⁸⁸,R⁸⁹,R⁹⁰,R⁹¹,R⁹²,R⁹³,R⁹⁴,R⁹⁵,R⁹⁶,R⁹⁷, R⁹⁸,R⁹⁹,R¹⁰⁰ and R¹⁰¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group.

12. The ink for ink-jet according to

claim 11

, wherein the vinyl polymer has ionic groups in an amount of from 0.1 to 3.0 mmol/g.

13. An ink for ink-jet comprising:

a coloring composition dispersed in a water based medium, containing coloring particulates containing an oil soluble dye represented by the following formula (III) and an oil soluble polymer;

wherein R¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹,—

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²²CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R³¹; and

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³, R²⁴,R²⁵,R²⁶,R²⁷,R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

R², R³, R⁶ and R⁷ each independently represents 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 or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵, R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹,R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷,R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R⁴ and R⁵ each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic ring; and

R⁸ represents a hydrogen atom, an aliphatic group or an aromatic group.

14. The ink for ink-jet according to

claim 13

, wherein the oil soluble polymer is a vinyl polymer having at least one of carboxyl groups and sulfonic acid groups as ionic groups.

15. A coloring composition comprising:

coloring particulates containing an oil soluble dye and an oil soluble polymer, said coloring particulates being dispersed in an aqueous medium; and

wherein the coloring composition has wavelength of maximum absorption (λ

max(nm)) in the wavelength range from 510 to 560 nm and when the absorbance at the wavelength of maximum absorption (λ

max(nm)) is regarded as 1, the absorbance at a wavelength (λ

max +75 (nm)) is no more than 0.2 and the absorbance at a wavelength (λ

max−

75 (nm)) is no more than 0.4.

16. A coloring composition comprising:

coloring particulates containing an oil soluble dye represented by the following formula (I) and a vinyl polymer having at least one of carboxyl groups and sulfonic acid groups as ionic groups, said coloring particulates being dispersed in an aqueous medium;

wherein R¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹,—

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²²CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R³¹; and

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³,R²⁴,R²⁵,R²⁶, R²⁷,R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

A represents —

NR⁴R⁵ or a hydroxyl group;

R⁴ and R⁵ each independently represents a hydrogen tom, an aliphatic group, an aromatic group or a heterocyclic group;

B¹ represents ═

C(R⁶)—

or ═

N—

;

B² represents —

C(R⁷)═

or —

N═

;

R², R³, R⁶ and R⁷ each independently represents 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 or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵,R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹,R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷, R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R² and R³,R³ and R⁴,R⁴ and R⁵,R⁵ and R⁶, or R⁶ and R⁷ may be bonded to each other to form a ring;

C forms a 5- or 6-membered nitrogen-containing heterocycle;

this heterocycle may be substituted with at least one substituent selected from an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR⁸¹,—

SR⁸²,—

CO₂R⁸³,—

OCOR⁸⁴,—

NR⁸⁵R⁸⁶,—

CONR⁸⁷R⁸⁸,—

SO₂R⁸⁹,SO₂NR⁹⁰R⁹¹,—

NR⁹²CONR⁹³R⁹⁴,—

NR⁹⁵CO₂R⁹⁶,—

COR⁹⁷,—

NR⁹⁸COR⁹⁹, and —

NR¹⁰⁰SO₂R¹⁰¹;

the substituent(s) may further have one or more substituents;

the nitrogen-containing heterocycle may be combined with another ring to form a condensed ring; and

R⁸¹,R⁸²,R⁸³,R⁸⁴,R⁸⁵,R⁸⁶,R⁸⁷,R⁸⁸,R⁸⁹,R⁹⁰,R⁹¹,R⁹²,R⁹³,R⁹⁴,R⁹⁵,R⁹⁶,R⁹⁷, R⁹⁸,R⁹⁹,R¹⁰⁰ and R¹⁰¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group.

17. A coloring composition comprising:

coloring particulates containing an oil soluble dye represented by the following formula (III) and an oil soluble polymer, said coloring particulates being dispersed in an aqueous medium;

wherein R¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹,—

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²²CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R³¹; and

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³, R²⁴,R²⁵,R²⁶,R²⁷,R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

R²,R³,R⁶ and R⁷each independently represents 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 or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵, R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹,R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷,R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R⁴ and R⁵ each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic ring; and

R⁸ represents a hydrogen atom, an aliphatic group or an aromatic group.

18. An ink-jet printing process comprising:

(a) preparing an ink for ink jet, containing coloring composition in which coloring particulates containing an oil soluble dye and an oil soluble polymer are dispersed in an aqueous medium, wherein the coloring composition has wavelength of maximum absorption (λ

A max(nm)) in the wavelength range from 510 to 560 nm and when the absorbance at the wavelength of maximum absorption (λ

max(nm)) is regarded as 1, the absorbance at a wavelength (λ

max+75 (nm)) is no more than 0.2 and the absorbance at a wavelength (λ

max−

75 (nm)) is no more than 0.4; and

(b) using the ink for recording in an ink-jet printing device.

19. An ink-jet printing process comprising:

(a) preparing an ink for ink jet, containing coloring composition in which coloring particulates containing an oil soluble dye represented by the following formula (I) and a vinyl polymer having at least one of carboxyl groups and sulfonic acid groups as ionic groups, are dispersed in an aqueous medium;

wherein R¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹,—

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²²CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R³¹; and

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³,R²⁴,R²⁵,R²⁶, R²⁷,R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

A represents —

NR⁴R⁵ or a hydroxyl group;

R⁴ and R⁵ each independently represents a hydrogen tom, an aliphatic group, an aromatic group or a heterocyclic group;

B¹ represents ═

C(R⁶)—

or ═

N—

;

B² represents —

C(R⁷)═

or —

N═

;

R²,R³,R⁶ and R⁷ each independently represents 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 or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵,R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷, R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R² and R³,R³ and R⁴,R^{4 and R5},R⁵ and R⁶, or R⁶ and R⁷ may be bonded to each other to form a ring;

C forms a 5- or 6-membered nitrogen-containing heterocycle;

this heterocycle may be substituted with at least one substituent selected from an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR⁸¹,—

SR⁸²,—

CO₂R⁸³,—

OCOR⁸⁴,—

NR⁸⁵R⁸⁶,—

CONR⁸⁷R⁸⁸,—

SO₂R⁸⁹,SO₂NR⁹⁰R⁹¹,—

NR⁹²CONR⁹³R⁹⁴,—

NR⁹⁵CO₂R⁹⁶,—

COR⁹⁷,—

NR⁹⁸COR⁹⁹, and —

NR¹⁰⁰SO₂R¹⁰¹;

the substituent(s) may further have one or more substituents;

the nitrogen-containing heterocycle may be combined with another ring to form a condensed ring; and

R⁸¹,R⁸²,R⁸³,R⁸⁴,R⁶⁵,R⁸⁶,R⁸⁷,R⁸⁸,R⁸⁹,R⁹⁰,R⁹¹,R⁹²,R⁹³,R⁹⁴,R⁹⁵,R⁹⁶,R⁹⁷, R⁹⁸,R⁹⁹,R¹⁰⁰ and R¹⁰¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group, and

(b) using the ink for recording in an ink-jet printing device.

20. An ink-jet printing process comprising:

(a) preparing an ink an ink jet, containing coloring composition in which coloring particulates contain an oil soluble dye represented by the following formula (III) and an oil soluble polymer, said coloring particulates being dispersed in an aqueous medium,

wherein R¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹¹,—

SR¹²,—

CO₂R¹³,—

OCOR¹⁴,—

NR¹⁵R¹⁶,—

CONR¹⁷R¹⁸,—

SO₂R¹⁹,—

SO₂NR²⁰R²¹,—

NR²²CONR²³R²⁴,—

NR²⁵CO₂R²⁶,—

COR²⁷,—

NR²⁸COR²⁹, or —

NR³⁰SO₂R³¹; and

R¹¹,R¹²,R¹³,R¹⁴,R¹⁵,R¹⁶,R¹⁷,R¹⁸,R¹⁹,R²⁰,R²¹,R²²,R²³, R²⁴,R²⁵,R²⁶,R²⁷,R²⁸,R²⁹,R³⁰ and R³¹ each independently represents a hydrogen atom, an aliphatic group, or an aromatic group;

R²,R³,R⁶ and R⁷ each independently represents 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 or —

NR⁷⁰SO₂R⁷¹;

R⁵¹,R⁵²,R⁵³,R⁵⁴,R⁵⁵, R⁵⁶,R⁵⁷,R⁵⁸,R⁵⁹,R⁶⁰,R⁶¹,R⁶²,R⁶³,R⁶⁴,R⁶⁵,R⁶⁶,R⁶⁷,R⁶⁸,R⁶⁹,R⁷⁰ and R⁷¹ each independently represents a hydrogen atom, an aliphatic group or an aromatic group;

R⁴ and R⁵ each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic ring; and

R⁸ represents a hydrogen atom, an aliphatic group or an aromatic group, and

(b) using the ink for recording in an ink-jet printing device.