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

Patent metadata

Field	Value
Publication number	US-9732176-B2
Application number	US-201314439918-A
Country	US
Kind code	B2
Filing date	Nov 26, 2013
Priority date	Dec 11, 2012
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

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 containing 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 method for producing a pigment dispersant comprising as a main component, a polymer obtained by subjecting particular monomers to living radical polymerization using a polymerization-initiating compound, the method comprising:
reacting
a polymer (E) having an epoxy group, or an isocyanate group, or a combination thereof,
wherein the polymer (E) is obtained by subjecting at least one or more monomers comprising a methacrylate (D) having an epoxy group, or a methacrylate (D) having an isocyanate group, or a combination thereof, to living radical polymerization under the presence of the polymerization-initiating compound and a catalyst using the monomers in a ratio so that a total number of moles of the methacrylate-based monomers is in a range from 20 to 50 mol relative to 1 mol of the polymerization-initiating compound,

with a compound (F) having any one of functional groups selected from the group consisting of a hydroxy group, a primary amino group, a secondary amino group, and a carboxyl group and having an acidic group, or a basic group, or a combination thereof, and
a compound (G) having one of functional groups selected from the group consisting of a hydroxy group, a primary amino group, a secondary group, and a carboxyl group at a terminal thereof, and having any one of polymer chains having a molecular weight in a range from 500 to 5000 and being 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,
using the compound (G) so that a proportion of the compound (G)-derived polymer chain in the formed polymer is in a range from 50 to 90 mass % expressed as a mass ratio.

2. A method for producing a pigment dispersant comprising as a main component, a polymer obtained by subjecting particular monomers to living radical polymerization using a polymerization-initiating compound,
the method comprising:
obtaining the polymer by subjecting monomers to living radical polymerization in the presence of the polymerization-initiating compound and a catalyst,
using as raw materials, two or more monomers comprising at least 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 any one of polymer chains having a molecular weight in a range from 500 to 5000 and being 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
using the monomers in a ratio so that a total number of moles of the methacrylate-based monomers in the monomers is in a range from 20 to 50 mol relative to 1 mol of the polymerization-initiating compound, and are used so that a proportion of the polymer chain in the formed polymer is in a range from 50 to 90 mass % expressed as a mass ratio,

wherein the polymerization-initiating compound used in the living radical polymerization is at least one of iodine and an iodine compound, and
the catalyst used in the living radical polymerization is at least one compound selected from the group consisting of phosphorus halides, phosphite-based compounds, phosphinate compounds, imide-based compounds, phenol-based compounds, diphenylmethane-based compounds, and cyclopentadiene-based compounds.

3. A pigment dispersion liquid comprising:
a pigment dispersant;
a pigment;
a dye derivative; and
one or more liquid media;
wherein the pigment dispersant comprises, as a main component;
a polymer obtained by subjecting particular monomers to living radical polymerization using a polymerization-initiating compound,
the polymer is a graft copolymer formed through the living radical polymerization using two or more monomers comprising at least:
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 any one of polymer chains having a molecular weight from 500 to 5000 and being 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,

in a ratio so that a total number of moles of the methacrylate-based monomers in raw material monomers is in a range from 20 to 50 mol relative to 1 mol of the polymerization-initiating compound,

the graft copolymer has a main chain having a methacrylate (A)-derived acidic group or basic group bonded thereto and a side chain that is a macromonomer (B)-derived polymer chain, and
a ratio of the 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 relative to the graft copolymer is in a range from 50 to 90 mass %,

the pigment dispersion liquid is obtained by dispersing the pigment dispersant and the pigment in the one or more liquid media selected from the group consisting of water, organic solvents, and polymerizable compounds, and
the dye derivative is (i) a dye derivative having a basic group when the methacrylate (A) having an acidic group or a basic group, which is a synthetic raw material of the polymer and is the main component of the pigment dispersant, is a methacrylate having an acidic group, or (ii) a dye derivative having an acidic group when the methacrylate (A) having an acidic group or a basic group is a methacrylate having a basic group.

Assignees

• Dainichiseika Color Chem

Inventors

• Shimanaka Hiroyuki
• Murakami Yoshikazu
• Tagi Yoichi

Classifications

• C08K2201/003

  Additives being defined by their diameter · CPC title

• C09D7/40

  Additives · CPC title

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• C09D11/107

  from unsaturated acids or derivatives thereof · CPC title

• C08F2438/00

  Living radical polymerisation · CPC title