Ink jet recording ink

• US 9,732,242 B2
• Filed: 06/22/2016
• Issued: 08/15/2017
• Est. Priority Date: 01/31/2014
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: Shinohara, Ryuji, Saito, Yuko
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US15/188,985
• Publication Number:
  US 20160297980A1
• Time in Patent Office: 419 Days
• Field of Search: 106 3151, 106 3152, 106 3158
• CPC Class Codes: B41J 2/01 Ink jet
• CPC Class Codes: C09B 29/103 of the naphthalene series
• CPC Class Codes: C09B 29/30 Amino naphtholsulfonic acid
• CPC Class Codes: C09B 33/18 Trisazo or higher polyazo dyes
• CPC Class Codes: C09B 33/30 Tetrazo dyes of the type
• CPC Class Codes: C09B 35/46 the component K being an amino naphthol
• CPC Class Codes: C09B 35/60 of the type
• CPC Class Codes: C09B 35/62 of the type
• CPC Class Codes: C09B 62/04 to a triazine ring
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: C09D 11/38 characterised by non-macromolecular additives other than solvents, pigments or dyes

Abstract

The present invention provides an ink jet recording ink including a dye which has a weight average molecular weight of 850 or less and is represented by Formula (1) below, a water-soluble organic solvent which has an SP value of 9.4 or more and less than 9.75 and is represented by Formula (2) or (3) below, and water, in which the content of a surfactant is less than 0.1% by mass. R₁, R₂: H, a halogen atom, OH, COOH, C1-C6 alkyl group, C1-C6 alkoxy group, NO₂, an azophenyl group, -L1-Ra and the like, L₁: O, CH₂, C₆H₄, N═N, SO₂ or a combination thereof, Ra: a phenyl group, a naphthyl group, or the like, R₃: H, an azophenyl group, an azonaphthalene group, -L₂-Rb or the like, L₂: C(═O), C₆H₄, N═N, NH, SO₂ or a combination thereof, Rb: a phenyl group, a naphthyl group, a pyrimidyl group, or the like; M⁺: H⁺, Na⁺, NH₄⁺, an alkylammonium ion or the like, R: C2-C6 unsubstituted alkyl group, and n is 1 to 3.

Claims

1. An ink jet recording ink comprising:

a dye which has a weight average molecular weight of 850 or less and is represented by Formula (1) below;

a water-soluble organic solvent which has an SP value of 9.6 or more and less than 9.7 and is represented by Formula (2) below; and

water,

wherein a content of a surfactant is less than 0.1% by mass,

2. The ink jet recording ink according to claim 1,

wherein a content of the water-soluble organic solvent represented by Formula (2) above is 0.1% by mass to 4.5% by mass with respect to the total mass of the ink.

3. The ink jet recording ink according to claim 1,

wherein the dye represented by Formula (1) above is a monoazo dye.

4. The ink jet recording ink according to claim 1,

wherein the dye represented by Formula (1) above has a weight average molecular weight of 650 to 850.

5. The ink jet recording ink according to claim 1,

wherein in Formula (1) above, R₃ represents —

NH—

SO₂—

C₆H₅ or —

NH—

SO₂—

C₆H₄—

CH₃.

6. The ink jet recording ink according to claim 1,

wherein in Formula (1) above, M⁺ is a sodium ion.

7. The ink jet recording ink according to claim 1,

wherein the dye represented by Formula (1) above has a weight average molecular weight of 650 to 850, and in Formula (1) above, R₃ represents —

NH—

SO₂—

C₆H₅ or —

NH—

SO₂—

C₆H₄—

CH₃.

8. The ink jet recording ink according to claim 7,

wherein a content of the water-soluble organic solvent represented by Formula (2) above is 0.1% by mass to 4.5% by mass with respect to the total mass of the ink.

9. The ink jet recording ink according to claim 1,

wherein the dye represented by Formula (1) above is a compound represented by Formula (1a) below, Formula (1a)

10. The ink jet recording ink according to claim 1,

wherein a content of the water-soluble organic solvent represented by Formula (2) above is 5 parts by mass to 200 parts by mass with respect to 100 parts by mass of the dye.

11. The ink jet recording ink according to claim 9,

wherein a content of the water-soluble organic solvent represented by Formula (2) above is 5 parts by mass to 200 parts by mass with respect to 100 parts by mass of the dye.

12. The ink jet recording ink according to claim 1,

wherein a content of the water-soluble organic solvent represented by Formula (2) above is 10 parts by mass to 150 parts by mass with respect to 100 parts by mass of the dye.

13. The ink jet recording ink according to claim 1, further comprising:

an organic solvent other than the water-soluble organic solvent represented by Formula (2) above,

wherein a content of the water-soluble organic solvent represented by Formula (2) above is 1% by mass to 40% by mass with respect to the total mass of the organic solvents.

14. The ink jet recording ink according to claim 9, further comprising:

an organic solvent other than the water-soluble organic solvent represented by Formula (2),

wherein a content of the water-soluble organic solvent represented by Formula (2) above is 1.2% by mass to 25% by mass with respect to the total mass of the organic solvents.

15. The ink jet recording ink according to claim 14,

wherein the organic solvent other than the water-soluble organic solvent represented by Formula (2) above is glycerin, diethylene glycol, a pyrrolidone derivative, or a combination thereof.

16. The ink jet recording ink according to claim 1,

wherein the water-soluble organic solvent represented by Formula (2) above is dipropylene glycol monobutyl ether, tripropylene glycol monoethyl ether, propylene glycol monohexyl ether, or tripropylene glycol monohexyl ether.

17. The ink jet recording ink according to claim 15, wherein the water-soluble organic solvent represented by Formula (2) above is dipropylene glycol monobutyl ether, tripropylene glycol monoethyl ether, propylene glycol monohexyl ether, or tripropylene glycol monohexyl ether.