Ink jet recording ink

Patent metadata

Field	Value
Publication number	US-9732242-B2
Application number	US-201615188985-A
Country	US
Kind code	B2
Filing date	Jun 22, 2016
Priority date	Jan 31, 2014
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

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. R 1 , R 2 : H, a halogen atom, OH, COOH, C1-C6 alkyl group, C1-C6 alkoxy group, NO 2 , an azophenyl group, -L1-Ra and the like, L 1 : O, CH 2 , C 6 H 4 , N═N, SO 2 or a combination thereof, Ra: a phenyl group, a naphthyl group, or the like, R 3 : H, an azophenyl group, an azonaphthalene group, -L 2 -Rb or the like, L 2 : C(═O), C 6 H 4 , N═N, NH, SO 2 or a combination thereof, Rb: a phenyl group, a naphthyl group, a pyrimidyl group, or the like; M + : H + , Na + , NH 4 + , an alkylammonium ion or the like, R: C2-C6 unsubstituted alkyl group, and n is 1 to 3.

First claim

What is claimed is:

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,

wherein in Formula (1), R 1 represents a hydrogen atom, methyl group, a nitro group, an anilino group, an acetamide group, —O—C 6 H 5 , or —O—CH 2 —C 6 H 5 ,
R 2 represents a hydrogen atom or a halogen atom,
R 3 represents a monovalent group selected from the group consisting of a hydrogen atom, an amino group, an acetamide group, an azophenyl group, an azonaphthalene group, and -L 2 -Rb,
L 2 represents a bivalent linking group consisting of one or a combination of two to five selected from the group consisting of —C(═O)—, —C 6 H 4 —, —N═N—, —NH—, and —SO 2 —,
Rb represents a phenyl group, a naphthyl group, a pyrimidyl group, a triazinyl group, or a quinoxaline group, and
M + represents a hydrogen ion, a sodium ion, a potassium ion, a lithium ion, an ammonium ion, or an alkylammonium ion, and

in Formula (2), R represents an unsubstituted alkyl group having 2 to 6 carbon atoms, and n represents an integer of 1 to 3.

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, R 3 represents —NH—SO 2 —C 6 H 5 or —NH—SO 2 —C 6 H 4 —CH 3 .

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, R 3 represents —NH—SO 2 —C 6 H 5 or —NH—SO 2 —C 6 H 4 —CH 3 .

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)

wherein in Formula (1a), R 4 and R 5 each independently represent a monovalent group selected from the group consisting of a hydrogen atom, a halogen atom, a methyl group, a phenoxy group, a nitro group, an acetamide group, and a phenylmethoxy group, and
R 6 represents a hydrogen atom or a methyl group.

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.

Assignees

• Fujifilm Corp

Inventors

• Shinohara Ryuji
• Saito Yuko

Classifications

• B41J2/01

  Ink jet · CPC title

• C09B33/18

  Trisazo or higher polyazo dyes · CPC title

• C09B33/30

  Tetrazo dyes of the type [IMAGE cpc-sch-C09B-1014.gif] · CPC title

• C09B29/30

  Amino naphtholsulfonic acid · CPC title

• C09B62/04

  to a triazine ring · CPC title