IP Library › Granted Patent US 10,240,053
Granted Patent B2
US 10,240,053 · App. 15/915,225 · Granted Mar 26, 2019

Aqueous ink, ink cartridge, and ink jet recording method

Inventors: Kazuya Nushiro (Ichikawa, JP); Takashi Saito (Kawasaki, JP); Yukako Tamanuki (Tokyo, JP); Hiroshi Kakikawa (Fujisawa, JP)
Assignee: Canon Kabushiki Kaisha
C09D11/328B41J2/17513B41J2/17553B41M5/0023C09D11/033C09D11/037
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Quick Facts
Patent No.
US 10,240,053
App. No.
15/915,225
Granted
Mar 26, 2019
Kind
B2
Abstract

An aqueous ink for ink jet having a high color developing property, capable of recording an image having an excellent hue, and having excellent storage stability, containing a coloring material and a water-soluble organic solvent is provided. The coloring material is a compound represented by the following General Formula (1). The water-soluble organic solvent contains a first water-soluble organic solvent having two or more hydroxy groups and having a Log P value of −1.88 or more to −1.09 or less. The content (mass %) of the first water-soluble organic solvent is 5.0 times or more to 30.0 times or less by a mass ratio with respect the content (mass %) of the coloring material.

Claims (36)

1. An aqueous ink for ink jet comprising a coloring material and a water-soluble organic solvent,

wherein the coloring material is a compound represented by the following General Formula (1),

wherein the water-soluble organic solvent comprises a first water-soluble organic solvent having two or more hydroxy groups and having a Log P value of −1.88 or more to −1.09 or less, and

wherein the content (mass %) of the first water-soluble organic solvent is 5.0 times or more to 30.0 times or less by a mass ratio with respect to the content (mass %) of the coloring material:

wherein, in General Formula (1),

R 1 , R 2 and R 3 each independently represent a hydrogen atom; a carboxylic acid group; a sulfonic acid group; a hydroxy group; an acetylamino group; a halogen atom; a cyano group; a nitro group; a sulfamoyl group; an alkyl group having 1 to 4 carbon atom(s); an alkoxy group having 1 to 4 carbon atom(s); an alkoxy group having 1 to 4 carbon atom(s) substituted by at least one kind of group(s) selected from the group consisting of a hydroxy group, an alkoxy group having 1 to 4 carbon atom(s), a sulfonic acid group, and a carboxylic acid group; an alkylsulfonyl group having 1 to 4 carbon atom(s); or an alkylsulfonyl group having 1 to 4 carbon atom(s) substituted by at least one kind of group(s) selected from the group consisting of a hydroxy group, a sulfonic acid group, and a carboxylic acid group;

R 4 and R 5 each independently represent an alkylthio group having 1 to 4 carbon atom(s); an alkylthio group having 1 to 4 carbon atom(s) substituted by at least one kind of group(s) selected from the group consisting of a hydroxy group, a sulfonic acid group, and a carboxylic acid group; an alkoxy group having 1 to 4 carbon atom(s); or an alkoxy group having 1 to 4 carbon atom(s) substituted by at least one kind of group(s) selected from the group consisting of a hydroxy group, a sulfonic acid group, and a carboxylic acid group;

R 6 represents a hydrogen atom; a carboxylic acid group; a sulfonic acid group; an alkylcarbonylamino group having 1 to 4 carbon atom(s); a halogen atom; an alkyl group having 1 to 4 carbon atom(s); an alkoxy group having 1 to 4 carbon atom(s); or an alkoxy group having 1 to 4 carbon atom(s) substituted by at least one kind of group(s) selected from the group consisting of a hydroxy group, an alkoxy group having 1 to 4 carbon atom(s), a sulfonic acid group, and a carboxylic acid group;

R 7 represents an anilino group substituted with a sulfonic acid group or a naphthylamino group substituted with a sulfonic acid group, and R 7 may further have at least one kind of substituent(s) selected from the group consisting of: a sulfonic acid group; a carboxylic acid group; a phosphoric acid group; a sulfamoyl group; a carbamoyl group; a hydroxy group; an alkoxy group having 1 to 6 carbon atom(s); an amino group; a mono- or di-alkylamino group having 1 to 6 carbon atom(s); a mono- or di-arylamino group; an acetylamino group; an ureido group; an alkyl group having 1 to 6 carbon atom(s); a nitro group; a cyano group; a halogen atom; an alkylsulfonyl group having 1 to 6 carbon atom(s); and an alkylthio group having 1 to 6 carbon atom(s);

R 8 represents an anilino group; a naphthylamino group; a mono- or di-alkylamino group having 1 to 6 carbon atom(s); a mono- or di-arylamino group; an amino group; an alkylthio group having 1 to 6 carbon atom(s); a phenylthio group; a phenoxy group; an alkoxy group having 1 to 6 carbon atom(s); or a hydroxy group; and R 8 may further have at least one kind of substituent(s) selected from the group consisting of: a sulfonic acid group; a carboxylic acid group; a phosphoric acid group; a sulfamoyl group; a carbamoyl group; a hydroxy group; an alkoxy group having 1 to 6 carbon atom(s); an amino group; a mono- or di-alkylamino group having 1 to 6 carbon atom(s); a mono- or di-arylamino group; an acetylamino group; an ureido group; an alkyl group having 1 to 6 carbon atom(s); a nitro group; a phenyl group; a furyl group; a pyridyl group; a cyano group; a halogen atom; an alkylsulfonyl group having 1 to 6 carbon atom(s); and an alkylthio group having 1 to 6 carbon atom(s); and

R 9 represents a heterocyclic aromatic ring, or an aromatic ring to which a heterocyclic aromatic ring is bonded via an azo group, and these rings may have at least one kind of substituent(s) selected from the group consisting of: an alkyl group having 1 to 4 carbon atom(s); a sulfonic acid group; a carboxylic acid group; a phosphoric acid group; a sulfamoyl group; a carbamoyl group; a hydroxy group; an alkoxy group having 1 to 4 carbon atom(s); an alkoxy group having 1 to 4 carbon atom(s) substituted with a sulfonic acid group; a cyano group; an amino group; and an alkylcarbonylamino group having 1 to 4 carbon atom(s).

2. The aqueous ink according to claim 1 , wherein the compound represented by General Formula (1) is a compound represented by the following General Formula (2):

wherein, in General Formula (2),

R 10 represents an alkyl group having 1 to 4 carbon atom(s);

R 11 represents a carbamoyl group, a cyano group, an amino group, or an alkylcarbonylamino group having 1 to 4 carbon atom(s);

R 12 represents a hydrogen atom or an alkoxy group having 1 to 4 carbon atom(s);

Ms each independently represent a hydrogen atom, an alkali metal, an ammonium, or an organic ammonium;

a, b, c and d each independently represent an integer of 1 or more to 4 or less; and

e represents 1 or 2.

3. The aqueous ink according to claim 2 , wherein the compound represented by General Formula (2) is a compound represented by the following General Formula (3):

wherein, in General Formula (3),

R 11 represents a carbamoyl group, a cyano group, an amino group, or an alkylcarbonylamino group having 1 to 4 carbon atom(s);

R 12 represents a hydrogen atom or an alkoxy group having 1 to 4 carbon atom(s);

Ms each independently represent a hydrogen atom, an alkali metal, an ammonium, or an organic ammonium;

a, b, c and d each independently represent an integer of 1 or more to 4 or less; and

e represents 1 or 2.

4. The aqueous ink according to claim 1 , wherein the first water-soluble organic solvent comprises at least one kind selected from the group consisting of a polyethylene glycol having a number average molecular weight of 200, tetraethylene glycol, triethylene glycol, and diethylene glycol.

5. The aqueous ink according to claim 1 , wherein the first water-soluble organic solvent comprises bis(2-hydroxyethyl)sulfone.

6. An ink cartridge comprising:

an ink, and

an ink storage portion configured to house the ink,

wherein the ink comprises the aqueous ink according to claim 1 .

7. An ink jet recording method comprising:

ejecting an ink from an ink jet recording head; and

recording an image on a recording medium,

wherein the ink comprises the aqueous ink according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2018
From: NUSHIRO, KAZUYA; SAITO, TAKASHI; TAMANUKI, YUKAKO; KAKIKAWA, HIROSHI
To: CANON KABUSHIKI KAISHA
Reel/Frame 046330/0988 →
Priority Claims (2)
JP 2017-058409 · Mar 24, 2017 · national
JP 2018-022727 · Feb 13, 2018 · national
Continuity (1)
Related Publication 20180273786A1 · Sep 27, 2018
Cited By (5)
US 12,480,012 US 12,637,576 US 12,697,816 US 12,734,800 US 12,742,084