Azo dye, ink-jet recording ink containing the same, and ink-jet recording method

• US 20020049310A1
• Filed: 08/02/2001
• Published: 04/25/2002
• Est. Priority Date: 08/07/2000
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Tateishi, Keiichi, Fujiwara, Toshiki, Azuma, Yasushi
• Granted Patent: US 6,455,679 B1
• Time in Patent Office: Days
• US Class Current: 534/875
• CPC Class Codes: C09B 29/0037 containing a five-membered heterocyclic ring with two nitrogen atoms
• CPC Class Codes: C09B 29/0811 further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

The present invention provides a novel heterylaniline azo dye as well as an ink-jet recording ink and an ink-jet recording method enabling the formation of an image having a good hue and high durability to light and ozone gas. The ink-jet recording ink contains a heterylaniline azo dye derivative having a novel structure. The ink-jet recording method is characterized in that an image is formed by using the ink described above on an image-receiving material comprising a support having thereon an ink-receiving layer containing white inorganic pigment particles.

Claims

1. An ink-jet recording ink comprising the azo dye represented by the following general formula (I):

2. An ink-jet recording ink according to claim 1, wherein R₂ in the general formula (I) is a substituent selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group.

3. An ink-jet recording ink according to claim 1, wherein R₃, R₄, and R₅ in the general formula (I) are each a hydrogen atom.

4. An ink-jet recording ink according to claim 1, wherein R₆ in the general formula (I) is a substituent selected from the group consisting of an amide group, a ureido group, and a sulfonamide group.

5. An ink-jet recording ink according to claim 1, wherein the ionic hydrophilic group is a carboxyl group or a sulfo group.

6. An ink-jet recording ink according to claim 1, wherein any one group of R₁ and R₂, R₃ and R₁, and R₂ and R₅ in the general formula (I) forms a ring indicated by one of the following formulae:

7. An ink-jet recording ink according to claim 1, wherein the nitrogen-containing heterocycle, which is made up of the group W of atoms, and the condensed ring of the heterocycle in the general formula (I) are selected from the group consisting of imidazole, benzimidazole, pyrazole, triazole, thiazole, benzothiazole, isothiazole, benzisothiazole, oxazole, benzoxazole, thiadiazole, 3H-pyrrole, 3H-indole, isoxazole, and benzisoxazole.

8. An ink-jet recording ink according to claim 1, wherein the ink-jet recording ink can be prepared by dissolving and/or dispersing the azo dye in an aqueous medium.

9. An ink-jet recording ink according to claim 1, wherein the azo dye represented by the general formula (I) is the azo dye represented by the general formula (II):

10. An ink-jet recording ink according to claim 9, wherein X in the general formula (II) is a substituent selected from the group consisting of a cyano group, an alkylsulfonyl group having 1 to 12 carbon atoms, and an arylsulfonyl group having 6 to 18 carbon atoms.

11. An ink-jet recording ink according to claim 9, wherein Y in the general formula (II) is a substituent selected from the group consisting of a secondary or tertiary alkyl group and an aryl group.

12. An ink-jet recording ink according to claim 9, wherein the ionic hydrophilic group is a carboxyl group or a sulfo group.

13. An ink-jet recording ink according to claim 9, wherein A in the general formula (II) is represented by any one of the following general formulae (III):

14. An ink-jet recording ink according to claim 1, wherein the azo dye in an amount between 0.2 and 10 parts by weight is incorporated in 100 parts by weight of the ink-jet recording ink.

16. An ink-jet recording method according to claim 15, wherein the ink-jet recording ink comprising the azo dye represented by the general formula (I) is an ink-jet recording ink comprising the azo dye represented by the following general formula (II):

17. An ink-jet recording method according to claim 16, wherein A in the general formula (II) is represented by any one of the following general formulae (III):

19. An azo dye according to claim 18, wherein A in the general formula (IV) is represented by any one of the following general formulae (V):

15. An ink-jet recording method in which an image is formed on an image-receiving material comprising a support having thereon an ink-receiving layer containing white inorganic pigment particles by using an ink-jet recording ink comprising the azo dye represented by the following general formula (I):

18. An azo dye represented by the general formula (IV):