Azo dye, ink jet recording ink, heat sensitive recording material, color toner, color filter, ink jet recording method, ink cartridge and ink jet printer

• US 7,648,943 B2
• Filed: 07/07/2005
• Issued: 01/19/2010
• Est. Priority Date: 07/08/2004
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: Fujiwara, Toshiki, Takasaki, Masaru, Yabuki, Yoshiharu, Fujie, Yoshihiko
• Primary Examiner(s): Hess; Bruce H
• Application Number:
  US11/175,500
• Publication Number:
  US 20060009357A1
• Time in Patent Office: 1,657 Days
• Field of Search: None
• US Class Current: 503/227
• CPC Class Codes: B41M 2205/02 Dye diffusion thermal transfer printing (D2T2)
• CPC Class Codes: B41M 5/388 Azo dyes
• CPC Class Codes: C09B 29/0037 containing a five-membered heterocyclic ring with two nitrogen atoms
• CPC Class Codes: C09B 29/0088 Benzothiazoles
• CPC Class Codes: C09B 29/0092 containing a five-membered heterocyclic ring with two nitrogen and one sulfur as heteroatoms
• CPC Class Codes: C09B 29/3639 from a pyridine ring containing one or more amino groups
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: G03G 9/091 Azo dyes
• CPC Class Codes: G03G 9/0912 Indigoid; Diaryl and Triaryl methane; Oxyketone dyes
• CPC Class Codes: G03G 9/0914 Acridine; Azine; Oxazine; Thiazine-;(Xanthene-) dyes

Abstract

An azo dye represented by formula (II) as defined in the specification, a process of producing the same and a coloring composition containing the azo dye.

Claims

1. An azo dye represented by formula (I):

2. The azo dye according to claim 1, which is represented by formula (II):

3. A process of producing a compound represented by formula (II) according to claim 2, the process comprising:

(a) allowing an aminopyrazole represented by formula (III) to react with a diazotizing agent to form a diazonium salt;

(b) allowing the diazonium salt to react with a coupling agent represented by formula (IV) to form a compound represented by formula (II-H1); and

(c) allowing the compound represented by formula (II-H1) to react with an alkylating agent, an arylating agent or a heterylating agent in a presence of a base to form a compound represented by formula (II-R1);

4. The process of producing a compound represented by formula (II) according to claim 3, wherein the compound represented by formula (II-R1) is a compound represented by formula (II-R2):

5. A process of producing a compound represented by formula (II) according to claim 2, the process comprising:

6. The azo dye according to claim 1,

wherein the at least one ionic hydrophilic group contains a sulfo group.

7. The azo dye according to claim 6,

wherein the sulfo group has a counter ion, and

wherein the counter ion is a lithium ion.

8. An ink jet recording ink comprising at least one azo dye according to claim 1.

9. An ink jet recording method, which comprises forming an image with an ink jet recording ink according to claim 8 on an image receiving material comprising a substrate and an ink receiving layer containing an inorganic white pigment.

10. An ink cartridge comprising an ink jet recording ink according to claim 8.

11. An ink jet printer comprising an ink cartridge according to claim 10.

12. A heat sensitive recording material comprising at least one azo dye according to claim 1.

13. A color toner comprising at least one azo dye according to claim 1.

14. A color filter comprising at least one azo dye according to claim 1.

15. The azo dye according to claim 1, wherein formula (I) comprises 3 to 6 ionic hydrophilic groups.

16. The azo dye according to claim 1, wherein the ionic hydrophilic group is selected from the group consisting of a carboxyl group, a phosphono group, and a sulfo group.

17. The azo dye according to claim 16, wherein the ionic hydrophilic group is a sulfo group.

18. The azo dye according to claim 1, wherein a and e are each a substituted or unsubstituted alkyl group.

19. The azo dye according to claim 1, wherein a + e have 3 to 5 carbon atoms in total.

20. The azo dye according to claim 1, wherein the azo dye is represented by formula (I-1):

21. The azo dye according to claim 1, wherein the azo dye is represented by formula (I-2):