Pigment dispersant, production method for pigment dispersant, and pigment dispersion liquid

Patent metadata

Field	Value
Publication number	US-9988480-B2
Application number	US-201715645650-A
Country	US
Kind code	B2
Filing date	Jul 10, 2017
Priority date	Dec 11, 2012
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

The present invention provides a pigment dispersant that exhibits high fine dispersibility, stability, and fluidity in a small amount, a pigment dispersion liquid including the pigment dispersant, and a process of producing the pigment dispersant and pigment dispersion liquid. The pigment dispersant contains as a main component, a graft copolymer formed through living radical polymerization using two or more monomers including a methacrylate A having an acidic group or a basic group and a methacrylate-based macromonomer B having a methacrylate residue at one terminal of a particular polymer chain that has a molecular weight of from 500 to 5000. A ratio of a total molar number of the methacrylate-based monomers relative to 1 mol of a polymerization-initiating compound in the raw material monomers is from 20 to 50 mol. A ratio of the B component-derived polymer chain to the graft copolymer is from 50 to 90 mass %.

First claim

The invention claimed is:

1. A pigment dispersant comprising: as a main component, a polymer obtained by living radical polymerization of raw material monomers in the presence of a polymerization-initiating compound,
wherein the polymer is a graft copolymer formed from two or more monomers as the raw material monomers, comprising:
a methacrylate (A) having an acidic group or a basic group;
a methacrylate-based macromonomer (B) having weight average molecular weight in a range from 500 to 5000 and having a methacrylate residue at one terminal of any one of polymer chains selected from the group consisting of polyalkylene (C2 to C4) glycol chains, polyalkylene (C2 to C4) glycol monoalkyl (C1 to C18) ether chains, and poly(hydroxyalkyl (C2 to C18) carboxylic acid) chains; and
optionally other methacrylate-based monomer than the methacrylate (A) and the methacrylate-based macromonomer (B),

the graft copolymer has a main chain made of a methacrylate (A)-derived polymer having an acidic group or a basic group bonded thereto; and a side chain made of a macromonomer (B)-derived polymer chain,
the graft copolymer has an average degree of polymerization in a range from 20 to 50,
a mass ratio of the polymer chain selected from the group consisting of the polyalkylene (C2 to C4) glycol chains, the polyalkylene (C2 to C4) glycol monoalkyl (C1 to C18) ether chains, and the poly(hydroxyalkyl (C2 to C18) carboxylic acid) chains relative to the graft copolymer is in a range from 50 to 90 mass %, and
the methacrylate-based macromonomer (B) has the methacrylate residue at the one terminal of the any one of the polymer chains through a urea bond.

2. The pigment dispersant according to claim 1 ,
wherein a molar ratio of the methacrylate-based macromonomer (B) relative to a total amount of methacrylate-based monomers is in a range from 10 to 50%, where the total amount of the methacrylate-based monomers are a total amount of the methacrylate (A), the methacrylate-based macromonomer (B), and the other methacrylate-based monomer.

3. The pigment dispersant according to 1 ,
wherein the graft copolymer as the main component has number average molecular weight in a range from 5000 to 25000, and
the graft copolymer has an acid value in a range from 15 to 70 mgKOH/g or an amine value of from 15 to 70 mgKOH/g.

4. The pigment dispersant according to claim 1 ,
wherein the methacrylate (A) has a sulfonate group or a phosphate group.

5. A pigment dispersion liquid, which is a dispersion of the pigment dispersant according to claim 1 and a pigment in one or more liquid media selected from the group consisting of water, organic solvents, and polymerizable compounds.

6. A method for producing the pigment dispersant according to claim 1 , the method comprising:
obtaining the graft copolymer by subjecting the raw material monomers to the living radical polymerization in the presence of the polymerization-initiating compound,
wherein as the raw material monomers, the two or more monomers comprise:
the methacrylate (A) having the acidic group or the basic group; and
the methacrylate-based macromonomer (B); and
optionally the other methacrylate-based monomer,

a molar ratio of a total amount of methacrylate-based monomers in the raw material monomers relative to the polymerization-initiating compound, is in a range from 20 to 50 mol relative to 1 mol of the polymerization-initiating compound, where the total amount of the methacrylate-based monomers are a total amount of the methacrylate (A), the methacrylate-based macromonomer (B), and the other methacrylate-based monomer.

7. The method according to claim 6 ,
wherein the polymerization-initiating compound is at least one compound selected from the group consisting of iodine and iodine compounds.

8. A pigment dispersant comprising: as a main component, a polymer obtained by living radical polymerization of raw material monomers in the presence of a polymerization-initiating compound,
wherein the polymer is a graft copolymer formed from two or more monomers as the raw material monomers, comprising:
a methacrylate (A) having an acidic group, which is a sulfonate group or a phosphate group;
a methacrylate-based macromonomer (B) having weight average molecular weight in a range from 500 to 5000 and having a methacrylate residue at one terminal of any one of polymer chains selected from the group consisting of polyalkylene (C2 to C4) glycol chains, polyalkylene (C2 to C4) glycol monoalkyl (C1 to C18) ether chains, and poly(hydroxyalkyl (C2 to C18) carboxylic acid) chains; and
optionally other methacrylate-based monomer than the methacrylate (A) and the methacrylate-based macromonomer (B),

the graft copolymer has a main chain made of a methacrylate (A)-derived polymer having an acidic group bonded thereto; and a side chain made of a macromonomer (B)-derived polymer chain,
the graft copolymer has an average degree of polymerization in a range from 20 to 50, and
a mass ratio of the polymer chain selected from the group consisting of the polyalkylene (C2 to C4) glycol chains, the polyalkylene (C2 to C4) glycol monoalkyl (C1 to C18) ether chains, and the poly(hydroxyalkyl (C2 to C18) carboxylic acid) chains relative to the graft copolymer is in a range from 50 to 90 mass %.

9. A method for producing the pigment dispersant according to claim 8 , the method comprising:
obtaining the graft copolymer by subjecting the raw material monomers to the living radical polymerization in the presence of the polymerization-initiating compound,
wherein as the raw material monomers, the two or more monomers comprise:
the methacrylate (A) having the acidic group;
the methacrylate-based macromonomer (B); and
optionally the other methacrylate-based monomer,

a molar ratio of a total amount of methacrylate-based monomers in the raw material monomers relative to the polymerization-initiating compound, is in a range from 20 to 50 mol relative to 1 mol of the polymerization-initiating compound, where the total amount of the methacrylate-based monomers are a total amount of the methacrylate (A), the methacrylate-based macromonomer (B), and the other methacrylate-based monomer.

10. The pigment dispersant according to claim 8 ,
wherein a molar ratio of the methacrylate-based macromonomer (B) relative to a total amount of methacrylate-based monomers is in a range from 10 to 50%, where the total amount of the methacrylate-based monomers are a total amount of the methacrylate (A), the methacrylate-based macromonomer (B), and the other methacrylate-based monomer.

11. The pigment dispersant according to claim 8 ,
wherein the graft copolymer as the main component has number average molecular weight in a range from 5000 to 25000, and
the graft copolymer has an acid value in a range from 15 to 70 mgKOH/g.

Assignees

• Dainichiseika Color Chem

Inventors

• Shimanaka Hiroyuki
• Murakami Yoshikazu
• Tagi Yoichi

Classifications

• C09D11/107

  from unsaturated acids or derivatives thereof · CPC title

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• C08K3/04

  Carbon · CPC title

• C09D7/40

  Additives · CPC title

• C09D11/326

  characterised by the pigment dispersant · CPC title