Azo pigment, method for preparing azo pigment, dispersion including azo pigment, coloring composition, and inkjet recording ink

Patent metadata

Field	Value
Publication number	US-9359503-B2
Application number	US-201414166362-A
Country	US
Kind code	B2
Filing date	Jan 28, 2014
Priority date	Jul 29, 2011
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

An azo pigment or a tautomer thereof represented by the following Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.5°, 7.1° and 21.8° in the CuKα characteristic X-ray diffraction.

First claim

What is claimed is:

1. A pigment dispersion comprising:
an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.5°, 7.1° and 21.8° in a CuKα characteristic X-ray diffraction

wherein a volume average particle diameter of pigment particles in the pigment dispersion is 0.01 μm to 0.2 μm.

2. The pigment dispersion according to claim 1 ,
wherein the azo pigment has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.5°, 7.1°, 14.4°, 21.8° and 23.6° in the CuKα characteristic X-ray diffraction.

3. A pigment dispersion comprising:
an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.3°, 6.4° and 22.3° in a CuKα characteristic X-ray diffraction

wherein a volume average particle diameter of pigment particles in the pigment dispersion is 0.01 μm to 0.2 μm.

4. The pigment dispersion according to claim 3 ,
wherein the azo pigment has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.3°, 6.4°, 12.6°, 13.0° and 22.3° in the CuKα characteristic X-ray diffraction.

5. A pigment dispersion comprising:
an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 5.9° and 7.0° in a CuKα characteristic X-ray diffraction

wherein a volume average particle diameter of pigment particles in the pigment dispersion is 0.01 μm to 0.2 μm.

6. The pigment dispersion according to claim 5 ,
wherein the azo pigment has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 5.9°, 7.0°, 10.4° and 23.5° in the CuKα characteristic X-ray diffraction.

7. A pigment dispersion comprising:
an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 4.8°, 7.2° and 9.7° in a CuKα characteristic X-ray diffraction

wherein a volume average particle diameter of pigment particles in the pigment dispersion is 0.01 μm to 0.2 μm.

8. The pigment dispersion according to claim 7 ,
wherein the azo pigment has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 4.8°, 7.2°, 9.7°, 20.1° and 26.8° in the CuKα characteristic X-ray diffraction.

9. The pigment dispersion according to claim 7 ,
wherein a BET specific surface area by a nitrogen adsorption method is 50 m 2 /g or more.

10. A pigment dispersion comprising:
an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 4.9°, 8.8° and 13.1° in a CuKα characteristic X-ray diffraction

wherein a volume average particle diameter of pigment particles in the pigment dispersion is 0.01 μm to 0.2 μm.

11. The pigment dispersion according to claim 10 ,
wherein the azo pigment has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 4.9°, 8.8°, 13.1°, 19.7° and 25.2° in the CuKα characteristic X-ray diffraction.

12. A pigment dispersion comprising:
an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.6°, 9.2° and 21.5° in a CuKα characteristic X-ray diffraction

wherein a volume average particle diameter of pigment particles in the pigment dispersion is 0.01 μm to 0.2 μm.

13. The pigment dispersion according to claim 12 ,
wherein the azo pigment has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.6°, 9.2°, 10.3°, 21.5° and 25.6° in the CuKα characteristic X-ray diffraction.

14. A pigment dispersion comprising:
an azo pigment or a tautomer thereof represented by the following Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 4.8°, 9.2° and 13.0° in a CuKα characteristic X-ray diffraction

wherein a volume average particle diameter of pigment particles in the pigment dispersion is 0.01 μm to 0.2 μm.

15. The pigment dispersion according to claim 14 ,
wherein the azo pigment has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 4.8°, 6.5°, 9.2°, 9.7°, 13.0° and 24.4° in the CuKα characteristic X-ray diffraction.

16. A method for preparing an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.5°, 7.1 and 21.8° in a CuKα characteristic X-ray diffraction, the method comprising:
desolvating a solvate of an azo compound or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.3°, 6.4° and 22.3° in the CuKα characteristic X-ray diffraction

17. The method according to claim 16 ,
wherein desolvation is performed by heating the solvate at 60° C. or more.

18. A method for preparing an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 6.3°, 6.4° and 22.3° in a CuKα characteristic X-ray diffraction, the method comprising:
subjecting an azo compound or a tautomer thereof, which is represented by Formula (1), and has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of any one of (i) 6.6°, 9.2° and 21.5°, (ii) 4.8°, 7.2° and 9.7°, and (iii) 5.9°, 7.0° and 8.9° in the CuKα characteristic X-ray diffraction, to solvent heating treatment

19. The method according to claim 18 ,
wherein the solvent heating treatment is performed by heating and stirring the azo compound or the tautomer thereof, which is represented by Formula (1), and has characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of any one of (i) 6.6°, 9.2° and 21.5°, (ii) 4.8°, 7.2° and 9.7°, and (iii) 5.9°, 7.0° and 8.9° in the CuKα characteristic X-ray diffraction, at 20° C. or more in an organic solvent.

20. The method according to claim 19 ,
wherein the organic solvent is an alcohol-based organic solvent, a ketone-based organic solvent or an aprotic organic solvent.

21. A method for preparing an azo pigment or a tautomer thereof represented by Formula (1), and having characteristic X-ray diffraction peaks at Bragg angles (2θ±0.2°) of 4.8°, 7.2°, 9.5°, 9.7°, 10.7°, 17.4°, 19.0°, 20.1° and 26.8° in a CuKα characteristic X-ray diffraction, the method comprising:
heating and stirring the azo pigment or the tautomer thereof represented by Formula (1) at 60° C. or more in an organic solvent

Assignees

• Fujifilm Corp

Inventors

• Tateishi Keiichi
• Hayashi Shinya
• Yamada Hiroshi
• Nagata Yoshiaki

Classifications

• C09B67/0028 Primary

  of azo compounds · CPC title

• C09B67/0015

  of azoic pigments · CPC title

• C09D11/322

  Pigment inks · CPC title

• C09B67/009

  polymeric dispersing agent · CPC title

• C09D11/326

  characterised by the pigment dispersant · CPC title