Aqueous pigment dispersion liquid and aqueous pigment inkjet ink using same

Patent metadata

Field	Value
Publication number	US-9260589-B2
Application number	US-201314374318-A
Country	US
Kind code	B2
Filing date	Feb 8, 2013
Priority date	Feb 16, 2012
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

The present invention is an aqueous pigment dispersion liquid for inkjet comprising a pigment and a pigment dispersant. The pigment dispersant is at least any one of a graft copolymer and a block copolymer each comprising a polymer chain A and a polymer chain B, wherein the polymer chain A comprises 20 to 60 mass % of a constituent unit derived from a first cycloalkyl group-containing (meth)acrylate, 10 to 35 mass % of a constituent unit derived from (meth)acrylic acid, and 5 to 70 mass % of a constituent unit derived from another (meth)acrylate and the polymer chain B comprises at least any one of a constituent unit derived from a second cycloalkyl group-containing (meth)acrylate and a constituent unit derived from a vinyl monomer or (meth)acrylate having an aromatic ring.

First claim

The invention claimed is:

1. An aqueous pigment dispersion liquid for inkjet comprising:
a pigment in a range from 5 to 35 mass %;
a pigment dispersant in a range from 0.5 to 25 mass %;
an aqueous organic solvent, which is an organic solvent having miscibility with water, in a range from 5 to 30 mass %; and
water in a range from 20 to 80 mass %,
wherein the pigment dispersant comprises a graft copolymer in which a polymer chain A is grafted onto a polymer chain B,
the polymer chain A comprises:
a constituent unit derived from a first cycloalkyl group-containing (meth)acrylate in a range from 20 to 60 mass %;
a constituent unit derived from (meth)acrylic acid in a range from 10 to 35 mass %; and
a constituent unit derived from another (meth)acrylate in a range from 5 to 70 mass %, and

the polymer chain A has a number average molecular weight in a range from 1,000 to 10,000,
the polymer chain B comprises at least one material selected from the group consisting of a constituent unit derived from a second cycloalkyl group-containing (meth)acrylate, a constituent unit derived from a vinyl monomer having an aromatic ring, and a constituent unit derived from (meth)acrylate having an aromatic ring,
wherein the second cycloalkyl group-containing (meth)acrylate for the polymer chain B is selected from the group consisting of cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, 3,3,5-trimethylcyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, cyclohexyloxyethyl (meth)acrylate, and tricyclodecyl (meth)acrylate, isobornyl (meth)acrylate,
the vinyl monomer having an aromatic ring for the polymer chain B is selected from the group consisting of styrene, vinyl toluene, and vinyl naphthalene, and
the (meth)acrylate having an aromatic ring for the polymer chain B is selected from the group consisting of phenyl (meth)acrylate, naphthoxy (meth)acrylate, benzyl (meth)acrylate, phenoxy ethyl (meth)acrylate, and para-cumyl phenol ethylene oxide-modified (meth)acrylate,

a mass ratio A:B of the polymer chain A to the polymer chain B is in a range of 30 to 70:70 to 30, and
the graft copolymer has a number average molecular weight in a range from 2,000 to 20,000.

2. The aqueous pigment dispersion liquid according to claim 1 ,
wherein the pigment is at least one material selected from the group consisting of Color Index number (C.I.) Pigment Blue 15:3 and 15:4, C.I. Pigment Red 122 and 269, C.I. Pigment Violet 19, C.I. Pigment Yellow 74, 155, and 180, C.I. Pigment Green 36 and 58, C.I. Pigment Orange 43, and C.I. Pigment Black 7, and
the pigment has a number average primary particle diameter of less than 150 nm.

3. The aqueous pigment dispersion liquid according to claim 1 ,
wherein the aqueous organic solvent has a solubility to water of 20 mass % or more at 25° C., and
the aqueous organic solvent is at least one material selected from the group consisting of poly(n=1 or more)alkylene(C2 to 3) glycol monoalkyl ethers, poly(n=1 or more)alkylene(C2 to 3) glycol monoaryl ethers, poly(n=1 or more)alkylene(C2 to 3) glycol dialkyl ethers, alkylene diols, alkylene monool monoalkyl ethers, alkylene polyols, and amide solvents.

4. The aqueous pigment dispersion liquid according to claim 1 , wherein the pigment is coated with the pigment dispersant.

5. The aqueous pigment dispersion liquid according to claim 1 , wherein the first cycloalkyl group-containing (meth)acrylate is at least one material of cyclohexyl (meth)acrylate and 3,3,5-trimethylcyclohexyl (meth)acrylate.

6. An aqueous pigment inkjet ink comprising the aqueous pigment dispersion liquid according to claim 1 , wherein a content ratio of the pigment in the aqueous pigment inkjet ink is in a range from 4 to 10 mass %.

7. A method for preparing a dispersant-coated pigment, in which a coating treatment using a pigment dispersant is applied to a pigment, comprising:
(i) a step of precipitating the pigment dispersant by adding an acid to a pigment dispersion liquid obtained by mixing the pigment, the pigment dispersant, an aqueous organic solvent, which is an organic solvent having miscibility with water, water, and an alkaline agent, or
(ii) a step of precipitating the pigment dispersant by adding a kneaded product obtained by kneading the pigment and the pigment dispersant into a poor solvent for the pigment dispersant,
wherein the pigment dispersant comprises a graft copolymer in which a polymer chain A is grafted onto a polymer chain B;
the polymer chain A comprises:
a constituent unit derived from a first cycloalkyl group-containing (meth)acrylate in a range from 20 to 60 mass %;
a constituent unit derived from (meth)acrylic acid in a range from 10 to 35 mass %; and
a constituent unit derived from another (meth)acrylate in a range from 5 to 70 mass %, and

the polymer chain A has a number average molecular weight in a range from 1,000 to 10,000,
the polymer chain B comprises at least one material selected from the group consisting of a constituent unit derived from a second cycloalkyl group-containing (meth)acrylate, a constituent unit derived from a vinyl monomer having an aromatic ring, and a constituent unit derived from (meth)acrylate having an aromatic ring,
wherein the second cycloalkyl group-containing (meth)acrylate for the polymer chain B is selected from the group consisting of cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, 3,3,5-trimethylcyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, cyclohexyloxyethyl (meth)acrylate, and tricyclodecyl (meth)acrylate, isobornyl (meth)acrylate,
the vinyl monomer having an aromatic ring for the polymer chain B is selected from the group consisting of styrene, vinyl toluene, and vinyl naphthalene, and
the (meth)acrylate having an aromatic ring for the polymer chain B is selected from the group consisting of phenyl (meth)acrylate, naphthoxy (meth)acrylate, benzyl (meth)acrylate, phenoxy ethyl (meth)acrylate, and para-cumyl phenol ethylene oxide-modified (meth)acrylate,

a mass ratio A:B of the polymer chain A to the polymer chain B is in a range of 30 to 70:70 to 30, and
the graft copolymer has a number average molecular weight in a range from 2,000 to 20,000.

8. An aqueous pigment dispersion liquid for inkjet comprising:
a pigment in a range from 5 to 35 mass %;
a pigment dispersant in a range from 0.5 to 25 mass %;
an aqueous organic solvent, which is an organic solvent having miscibility with water, in a range from 5 to 30 mass %; and
water in a range from 20 to 80 mass %,
wherein the pigment dispersant comprises a block copolymer in which one end of a polymer chain A is linked to one end of a polymer chain B,
the polymer chain A comprises:
a constituent unit derived from a first cycloalkyl group-containing (meth)acrylate in a range from 28.9 to 60 mass %;
a constituent unit derived from (meth)acrylic acid in a range from 10 to 35 mass %; and
a constituent unit derived from another (meth)acrylate in a range from 5 to 70 mass %, and

the polymer chain A has a number average molecular weight in a range from 1,000 to 10,000,
the polymer chain B comprises at least one material selected from the group consisting of a constituent unit derived from a second cycloalkyl group-containing (meth)acrylate, a constituent unit derived from a vinyl monomer having an aromatic ring, and a constituent unit derived from (meth)acrylate having an aromatic ring,
a mass ratio A:B of the polymer chain A to the polymer chain B is in a range of 30 to 70:70 to 30, and
the block copolymer has a number average molecular weight in a range from 2,000 to 20,000.

9. The aqueous pigment dispersion liquid according to claim 8 ,
wherein the pigment is at least one material selected from the group

Assignees

• Dainichiseika Color Chem

Inventors

• Shimanaka Hiroyuki
• Aoyagi Shinichiro
• Murakami Yoshikazu
• Kanou Katsuhiko

Classifications

• C08K3/04

  Carbon · CPC title

• C09B67/0041

  mixtures containing one azo dye · CPC title

• C09B67/0013

  with polymeric coatings · CPC title

• C08K5/053

  Polyhydroxylic alcohols · CPC title

• C08K5/3437 Primary

  condensed with carbocyclic rings · CPC title