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

• US 6,521,031 B2
• Filed: 03/08/2001
• Issued: 02/18/2003
• Est. Priority Date: 03/29/2000
• Status: Expired due to Fees

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Ito, Takayuki, Kimura, Keizo
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US09/800,779
• Publication Number:
  US 20010045176A1
• Time in Patent Office: 712 Days
• Field of Search: 106/31.47, 106/31.49, 106/31.46, 865/9, 544/224, 544/238, 546/183, 546/195, 546/200, 546/223, 548/454, 548/467, 548/486
• US Class Current: 106/31.47
• 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
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

An ink-jet ink which includes a coloring composition which contains an oil-soluble dye represented in the following formula (I). In the formula (I), R¹ and R² represent respectively independently a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, or the like. A represents —NR⁵R⁶ or a hydroxyl group. R⁵ and R⁶ represent respectively independently a hydrogen atom, an aliphatic group, or the like. B¹ represents ═C(R⁷)— or ═N—, and B²represents —C (R⁸)═ or —N═. R³, R⁴, R⁷, and R⁸ represent respectively independently a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, or the like. Q includes at least one nitrogen atom and, together with a carbon atom to be combined, represents an atom group which is required to form a nitrogen-containing heterocyclic ring having a five-membered ring or more.

Claims

1. An ink-jet ink which includes a coloring composition which contains an oil-soluble dye represented in the following formula (I):

wherein, R¹ and R² represent respectively independently one of a hydrogen atom, a halogen 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, and NR³⁰SO₂R³¹;

R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R^{17, R18}, R¹⁹, R²⁰, R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, and R³¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group;

R¹ and R² may be connected to each other and form a ring;

A represents one of —

NR⁵R⁶ and a hydroxyl group;

R⁵ and R⁶ represent respectively independently one of a hydrogen atom, an aliphatic group, an aromatic group, and a heterocyclic group;

B¹ represents one of ═

C(R⁷)— and

═

N— and

B² represents one of —

C(R⁸)═ and

—

N═

;

R³, R⁴, R⁷, and R⁸ 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;

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;

R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ may be combined with each other and form rings; and

Q includes at least one nitrogen atom and, together with a carbon atom to be combined, represents an atom group which is required to form a nitrogen-containing heterocyclic ring having a five-membered ring or more.

2. An ink-jet ink according to claim 1, wherein said oil-soluble dye which is represented in the formula (I) is an oil-soluble dye which is represented in the following formula (II):

wherein, R¹, R³, R⁴, R⁵, R⁶, R⁷, and R⁸ are respectively synonymous with R¹, R³, R⁴, R⁵, R⁶, R⁷, and R⁸ in the above formula (I);

R⁹¹and R⁹² represent respectively independently one of a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹⁰¹, —

SR¹⁰², —

CO₂R¹⁰³, —

OCOR¹⁰⁴, —

NR¹⁰⁵R¹⁰⁶, —

CONR¹⁰⁷R¹⁰⁸, —

SO₂R¹⁰⁹, —

SO₂NR¹¹⁰R¹¹¹, —

NR¹¹²CONR¹¹³R¹¹⁴, —

NR¹¹⁵CO₂R¹¹⁶, —

COR¹¹⁷, —

NR¹¹⁸COR¹¹⁹, and NR¹²⁰SO₂R¹²¹;

R¹⁰¹, R¹⁰², R¹⁰³, R¹⁰⁴, R¹⁰⁵, R¹⁰⁶, R¹⁰⁷, R¹⁰⁸, R¹⁰⁹, R¹¹⁰, R¹¹¹, R¹¹², R¹¹³, R¹¹⁴, R¹¹⁵, R¹¹⁶, R¹¹⁷, R¹¹⁸, R¹¹⁹, R¹²⁰, and R¹²¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group; and

R⁹¹ and R⁹² may be combined with each other and form a ring.

3. An ink-jet ink according to claim 1, wherein said oil-soluble dye which is represented in the formula (I) is an oil-soluble dye which is represented in the following formula (III):

wherein, R¹, R³, R⁴, R⁵, R⁶, R⁷, and R⁸ are respectively synonymous with R¹, R³, R⁴, R⁵, R⁶, R^7, and R⁸ in the above formula (I);

R⁹³, R⁹⁴, R⁹⁵, and R⁹⁶ represent respectively independently one of a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹⁰¹, —

SR¹⁰², —

CO₂R¹⁰³, OCOR¹⁰⁴, —

NR¹⁰⁵R¹⁰⁶, —

CONR¹⁰⁷R¹⁰⁸, —

SO₂R¹⁰⁹, —

SO₂NR¹¹⁰R¹¹¹, —

NR¹¹²CONR¹¹³R¹¹⁴, —

NR¹¹⁵CO₂R¹¹⁶, —

COR¹¹⁷, —

NR¹¹⁸CR¹¹⁹, and NR¹²⁰SO₂R¹²¹;

R¹⁰¹, R¹⁰², R¹⁰³, R¹⁰⁴, R¹⁰⁵, R¹⁰⁶, R¹⁰⁷, R¹⁰⁸, R¹⁰⁹, R¹¹⁰, R¹¹¹, R¹¹², R¹¹³, R¹¹⁴, R¹¹⁵, R¹¹⁶, R¹¹⁷, R¹¹⁸, R¹¹⁹, R¹²⁰, and R¹²¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group; and

R⁹³ and R⁹⁴, R⁹⁴ and R⁹⁵, and R⁹⁵ and R⁹⁶ may be combined with each other and form rings.

4. An ink-jet ink according to claim 1, wherein said oil-soluble dye which is represented in the formula (I) is dispersed in a water-based medium.

5. An ink-jet ink according to claim 4, wherein said oil-soluble dye is represented in the formula (I) and is dissolved in a high boiling point organic solvent which has a boiling point of 150°

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

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

6. An ink-jet ink according to claim 4, wherein coloring particulates, which contain said oil-soluble dye which is represented in the formula (I) and an oil-soluble polymer, are dispersed in the water-based medium.

7. An ink-jet ink according to claim 6, 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.

8. An ink-jet ink according to claim 6, wherein said coloring composition includes a high boiling point organic solvent.

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.

10. An ink-jet according to claim 6, wherein in the coloring particulates, said oil-soluble dye is dispersed in the oil-soluble polymer.

11. A coloring composition which contains an oil-soluble dye which is represented in the following formula (I):

wherein, R¹ and R² represent respectively independently one of a hydrogen atom, a halogen 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, and NR³⁰SO₂R³¹;

R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R²⁰, R²¹R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, and R³¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group;

R¹ and R² may be connected to each other and form a ring;

A represents one of —

NR⁵R⁶ and a hydroxyl group;

R⁵ and R⁶ represent respectively independently one of a hydrogen atom, an aliphatic group, an aromatic group, and a heterocyclic group;

B¹ represents one of ═

C(R⁷)— and

═

N— and

B²represents one of —

C(R⁸)═ and

—

N═

;

R³, R⁴, R⁷, and R⁸ 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;

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;

R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ may be combined with each other and form rings; and

Q includes at least one nitrogen atom and, together with a carbon atom to be combined, represents an atom group which is required to form a nitrogen-containing heterocyclic ring having a five-membered ring or more.

12. A coloring composition according to claim 11, wherein said coloring composition is used for an ink composition.

13. An ink jet recording method in which recording is carried out using an ink-jet ink, said ink-jet ink includes a coloring composition which contains an oil-soluble dye represented in the following formula (I):

wherein, R¹ and R² represent respectively independently one of a hydrogen atom, a halogen 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, and NR³⁰SO₂R³¹;

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

R¹ and R² may be connected to each other and form a ring;

A represents one of —

NR⁵R⁶ and a hydroxyl group;

R⁵ and R⁶ represent respectively independently one of a hydrogen atom, an aliphatic group, an aromatic group, and a heterocyclic group;

B¹ represents one of ═

C(R⁷)— and

═

N— and

B² represents one of —

C(R⁸)═ and

—

N═

;

R³, R⁴, R⁵, and R⁸ 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;

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;

R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ may be combined with each other and form rings; and

Q includes at least one nitrogen atom and, together with a carbon atom to be combined, represents an atom group which is required to form a nitrogen-containing heterocyclic ring having a five-membered ring or more.

14. An ink jet recording method according to claim 13, wherein said oil-soluble dye which is represented in the formula (I) is an oil-soluble dye which is represented in the following formula (II):

wherein, R¹, R³, R⁴, R⁵, R⁶, R⁷, and R⁸ are respectively synonymous with R¹, R³, R⁴, R⁵, R⁶, R⁷, and R⁸ in the above formula (I);

R⁹¹and R⁹² represent respectively independently one of a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹⁰¹, —

SR¹⁰², —

CO₂R¹⁰³, —

OCOR¹⁰⁴, —

NR¹⁰⁵R¹⁰⁶, —

CONR¹⁰⁷R¹⁰⁸, —

SO₂R¹⁰⁹, —

SO₂NR¹¹⁰R¹¹¹, —

NR¹¹²CONR¹¹³R¹¹⁴, —

NR¹¹⁵, CO₂R¹¹⁶, —

COR¹¹⁷, —

NR¹¹⁸COR¹¹⁹, and NR¹²⁰SO₂R¹²¹;

R¹⁰¹, R¹⁰², R¹⁰³, R¹⁰⁴, R¹⁰⁵, R¹⁰⁶, R¹⁰⁷, R¹⁰⁸, R¹⁰⁹, R¹¹⁰,R¹¹¹, R¹¹², R¹¹³, R¹¹⁴, R¹¹⁵, R¹¹⁶, R¹¹⁷, R¹¹⁸, R¹¹⁹, R¹²⁰, and R¹²¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group; and

R⁹¹ and R⁹² may be combined with each other and form a ring.

15. An ink jet recording method according to claim 13, wherein said oil-soluble dye which is represented in the formula (I) is an oil-soluble dye which is represented in the following formula (III):

wherein, R¹, R³, R⁴, R⁵, R⁶, R⁷, and R⁸ are respectively synonymous with R¹, R³, R⁴, R⁵, R⁶, R⁷, and R⁸ in the above formula (I);

R⁹³, R⁹⁴, R⁹⁵, and R⁹⁶ represent respectively independently one of a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR¹⁰¹, —

SR¹⁰², —

CO₂R¹⁰³, —

OCOR¹⁰⁴, —

NR¹⁰⁵R¹⁰⁶, —

CONR¹⁰⁷R¹⁰⁸, —

SO₂R₁₀₉, —

SO₂NR¹¹⁰R¹¹¹, —

NR¹¹²CONR¹¹³R¹¹⁴, —

NR¹¹⁵CO₂R¹¹⁶, —

COR¹¹⁷, —

NR¹¹⁸COR¹¹⁹, and NR¹²⁰SO₂R¹²¹;

R¹⁰¹, R¹⁰², R¹⁰³, R¹⁰⁴, R¹⁰⁵, R¹⁰⁶, R¹⁰⁷, R¹⁰⁸, R¹⁰⁹, R¹¹⁰, R¹¹¹, R¹¹², R¹¹³, R¹¹⁴, R¹¹⁵, R¹¹⁶, R¹¹⁷, R¹¹⁸, R¹¹⁹, R¹²⁰, and R¹²¹ represent respectively independently one of a hydrogen atom, an aliphatic group, and an aromatic group; and

R⁹³ and R⁹⁴, R⁹⁴ and R⁹⁵, and R⁹⁵ and R⁹⁶ may be combined with each other and form rings.

16. An ink jet recording method according to claim 13, wherein said oil-soluble dye which is represented in the formula (I) is dispersed in a water-based medium.

17. An ink jet recording method according to claim 16, wherein said oil-soluble dye is represented in the formula (I) and is dissolved in a high boiling point organic solvent which has a boiling point of 150°

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

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

18. An ink jet recording method according to claim 16, wherein coloring particulates, which contain said oil-soluble dye which is represented in the formula (I) and an oil-soluble polymer, are dispersed in the water-based medium.

19. An ink jet recording method according to claim 18, wherein said coloring composition includes a high boiling point organic solvent.

20. An ink jet recording method according to claim 18, wherein in the coloring particulates, said oil-soluble dye is dispersed in the oil-soluble polymer.