Toner and production method thereof

Patent metadata

Field	Value
Publication number	US-9958801-B2
Application number	US-201615152313-A
Country	US
Kind code	B2
Filing date	May 11, 2016
Priority date	May 14, 2015
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Provided is a toner including a toner particle containing a graft polymer, in which: the graft polymer has a crystalline polyester segment and an amorphous vinyl polymer segment; the crystalline polyester segment has a unit derived from a specific monomer (a) and a unit derived from a specific monomer (b); a content X (mol %) of the unit derived from the monomer (b) calculated from a specific formula is 1.0 mol % or more and 24 mol % or less; and a melting point of the graft polymer is 50° C. or more and 85° C. or less.

First claim

What is claimed is:

1. A toner, comprising a toner particle containing a binder resin, comprising:
a graft polymer having (i) an amorphous vinyl polymer segment and a crystalline polyester segment branched from the amorphous vinyl polymer segment, or (ii) a crystalline polyester segment and an amorphous vinyl polymer segment branched from the crystalline polyester segment;
the crystalline polyester segment comprising a unit derived from a monomer (a) and a unit derived from a monomer (b), monomer (a) being one or more monomers selected from the group consisting of a C 2-11 α,ω-straight-chain aliphatic diol, a C 2-13 α,ω-straight-chain aliphatic dicarboxylic acid, a C 2-12 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, an intramolecular acid anhydride of a C 2-13 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 2-13 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 2-12 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid and a lactonized compound of a C 2-12 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, and monomer (b) being one or more monomers selected from the group consisting of a C 12-22 α,ω-straight-chain aliphatic diol, a C 14-24 α,ω-straight-chain aliphatic dicarboxylic acid, a C 13-23 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, an intramolecular acid anhydride of a C 14-24 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 14-24 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 13-23 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid and a lactonized compound of a C 13-23 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, wherein
the crystalline polyester segment has a content X (mol %) of the unit derived from the monomer (b) of 1.0 to 20 mol % as calculated from X={Mb/(Ma+Mb)}×100 where Ma (mol/g) is the number of moles of the unit derived from the monomer (a) per unit mass, and Mb (mol/g) is the number of moles of the unit derived from the monomer (b) per unit mass, and
a melting point of the graft polymer is 50 to 85° C.

2. A toner according to claim 1 , wherein a content of the graft polymer is 1.0 to 35 mass % with respect to a total mass of the binder resin.

3. A toner according to claim 1 , wherein a mass ratio (C/A ratio) of the crystalline polyester segment to the amorphous vinyl polymer segment in the graft polymer is 40/60 to 90/10.

4. A toner according to claim 1 , wherein the amorphous vinyl polymer segment in the graft polymer has a weight-average molecular weight (Mw) of 3,000 to 20,000.

5. A toner according to claim 1 , wherein the graft polymer has a weight-average molecular weight (Mw) of 15,000 to 100,000.

6. A toner according to claim 1 , wherein the crystalline polyester segment is a terpolymer.

7. A toner according to claim 1 , wherein the content X (mol %) of the unit derived from the monomer (b) is 3.0 to 20 mol %.

8. A toner according to claim 1 , wherein the monomer group A is the C 2-11 α,ω-straight-chain aliphatic diol, the C 2-13 α,ω-straight-chain aliphatic dicarboxylic acid, or the C 2-12 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, and
the monomer group B is the C 12-22 α,ω-straight-chain aliphatic diol, the C 14-24 α,ω-straight-chain aliphatic dicarboxylic acid, or the C 13-23 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid.

9. A toner according to claim 1 , wherein the binder resin further contains a styrene-acrylic resin.

10. A method of producing a toner, comprising the steps of:
granulating a polymerizable monomer composition containing a polymerizable monomer capable of forming the binder resin and a graft polymer in an aqueous medium to polymerize the polymerizable monomer composition, wherein
the toner comprises a toner particle containing a binder resin,
the binder resin comprising:
a graft polymer having (i) an amorphous vinyl polymer segment and a crystalline polyester segment branched from the amorphous vinyl polymer segment, or (ii) a crystalline polyester segment and an amorphous vinyl polymer segment branched from the crystalline polyester segment;
the crystalline polyester segment comprising a unit derived from a monomer (a) and a unit derived from a monomer (b), monomer (a) being one or more monomers selected from the group consisting of a C 2-11 α,ω-straight-chain aliphatic diol, a C 2-13 α,ω-straight-chain aliphatic dicarboxylic acid, a C 2-12 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, an intramolecular acid anhydride of a C 2-13 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 2-13 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 2-12 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid and a lactonized compound of a C 2-12 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, and monomer (b) being one or more monomers selected from the group consisting of a C 12-22 α,ω-straight-chain aliphatic diol, a C 14-24 α,ω-straight-chain aliphatic dicarboxylic acid, a C 13-23 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, an intramolecular acid anhydride of a C 14-24 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 14-24 α,ω-straight-chain aliphatic dicarboxylic acid, an alkyl ester of a C 13-23 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid and a lactonized compound of a C 13-23 α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid, wherein
the crystalline polyester segment has a content X (mol %) of the unit derived from the monomer (b) of 1.0 to 20 mol % as calculated from X={Mb/(Ma+Mb)}×100 where Ma (mol/g) is the number of moles of the unit derived from the monomer (a) per unit mass, and Mb (mol/g) is the number of moles of the unit derived from the monomer (b) per unit mass, and
a melting point of the graft polymer is 50 to 85° C.

Assignees

• Canon Kk

Inventors

• Tanaka Masatake
• Nakagawa Yoshihiro
• Isono Naoya
• Takada Harumi
• TAGAWA Reo

Classifications

• G03G9/08755

  Polyesters · CPC title

• G03G9/08797

  characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature · CPC title

• G03G9/08795

  characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants · CPC title

• G03G9/08786 Primary

  Graft polymers · CPC title

• G03G9/0806

  whereby chemical synthesis of at least one of the toner components takes place · CPC title