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

• US 6,756,423 B2
• Filed: 12/21/2000
• Issued: 06/29/2004
• Est. Priority Date: 12/22/1999
• Status: Expired due to Fees

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Kimura, Keizo, Yamada, Makoto, Ishizuka, Takahiro
• Primary Examiner(s): SHOSHO, CALLIE E
• Application Number:
  US09/740,927
• Publication Number:
  US 20010023267A1
• Time in Patent Office: 1,286 Days
• Field of Search: 523/160, 523/161, 106/31.43, 106/31.46, 106/31.49, 106/31.47, 524/86, 524/87, 524/91, 524/94, 524/99, 524/102, 524/106, 524/589, 524/601
• US Class Current: 523/160
• 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, and 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;

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 group; and

wherein

X represents —

N═

, and Y represents —

C(R⁸)═

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

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

wherein the oil soluble dye and the vinyl polymer are separate compounds.

2. The ink for ink-jet according to claim 1, wherein in the coloring particulates, the oil soluble dye is dispersed in the oil soluble polymer.

3. 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 either adding water to the organic solvent or adding the organic solvent into water.

4. The ink for ink-jet according to claim 1, wherein the ionic group of the vinyl polymer is a carboxyl group.

5. The ink for ink-jet according to claim 1, wherein the vinyl polymer has ionic groups in and amount of from 0.1 to 3.0 mmol/g.

6. The ink for ink-jet according to claim 1, wherein R⁸ represents a substituted aryl group.

7. The ink for ink-jet according to claim 6, wherein a total number of substituents represented by —

NR⁷⁰SO₂R⁷¹ in the dye thereof is 2 or more.

8. 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 a vinyl polymer having at least one of a carboxyl group and a sulfonic acid group;

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 hologen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, —

OR⁵¹, —

SR⁵², —

CO₂R⁵³, —

OCOR⁵⁴, —

NR⁵⁵R⁵⁶, —

CONR⁵⁷R⁵⁸, —

SO₂R⁵⁹, SO₂R⁶⁰R⁶¹, —

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,

wherein the oil soluble dye and the vinyl polymer are separate compounds.

9. The ink for ink-jet according to claim 8, wherein R⁸ represents a substituted aryl group, and wherein a total number of substituents represented by —

NR⁷⁰SO₂R⁷¹ in the dye thereof is 2 or more.

10. A coloring composition comprising:

coloring particulates containing an oil soluble dye represented by the following formula (III) and a vinyl polymer having at least one of a carboxyl group and a sulfonic acid group, 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, and 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, —

SO₂R⁵³, —

OCOR⁵⁴, —

NR⁵⁵R⁵⁶, —

CONR⁵⁷R⁵⁸, —

SO₂R⁵⁹, SO₂NR⁶⁰R⁶¹, —

NR⁶²CONR⁶³R⁶⁴, —

NR⁶⁵SO₂R⁶⁶, —

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,

wherein the oil soluble dye and the vinyl polymer are separate compounds.

11. The ink for ink-jet according to claim 10, wherein R⁸ represents a substituted aryl group, and wherein a total number of substituents represented by —

NR⁷⁰SO₂R⁷¹ in the dye thereof is 2 or more.

12. An ink-jet printing process comprising:

(a) preparing an ink for an ink jet, containing coloring composition in which coloring particulates contain an oil soluble dye represented by the following formula (III) and a vinyl polymer having at least one of a carboxyl group and a sulfonic acid group, 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,

wherein the oil soluble dye and the vinyl polymer are separate compounds, and

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

13. The ink for ink-jet according to claim 12, wherein R⁸ represents a substituted aryl group, and wherein a total number of substituents represented by —

NR⁷⁰SO₂R⁷¹ in the dye thereof is 2 or more.