Toner and production method thereof

Patent metadata

Field	Value
Publication number	US-2016334727-A1
Application number	US-201615152313-A
Country	US
Kind code	A1
Filing date	May 11, 2016
Priority date	May 14, 2015
Publication date	Nov 17, 2016
Grant date	—

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, wherein
the binder resin comprises 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 comprises a unit derived from a monomer (a) and a unit derived from a monomer (b), the monomer (a) is one or more selected from the group consisting of the monomer group A described below; and the monomer (b) is one or more selected from the group consisting of the monomer group B described below; the crystalline polyester segment has a content X (mol %) of the unit derived from the monomer (b), as calculated from the following formula (1), of 1.0 mol % or more and 24 mol % or less:
X={Mb /( Ma+Mb )}×100  (1)

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° C. or more and 85° C. or less:
monomer group A:
an α,ω-straight-chain aliphatic diol having 2 or more and 11 or less carbon atoms;
an α,ω-straight-chain aliphatic dicarboxylic acid having 2 or more and 13 or less carbon atoms;
an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 2 or more and 12 or less carbon atoms;
an intramolecular acid anhydride of an α,ω-straight-chain aliphatic dicarboxylic acid having 2 or more and 13 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic dicarboxylic acid having 2 or more and 13 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 2 or more and 12 or less carbon atoms; and
a lactonized compound of an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 2 or more and 12 or less carbon atoms,

monomer group B:
an α,ω-straight-chain aliphatic diol having 12 or more and 22 or less carbon atoms;
an α,ω-straight-chain aliphatic dicarboxylic acid having 14 or more and 24 or less carbon atoms;
an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 13 or more and 23 or less carbon atoms;
an intramolecular acid anhydride of an α,ω-straight-chain aliphatic dicarboxylic acid having 14 or more and 24 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic dicarboxylic acid having 14 or more and 24 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 13 or more and 23 or less carbon atoms; and
a lactonized compound of an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 13 or more and 23 or less carbon atoms.

2 . A toner according to claim 1 , wherein a content of the graft polymer is 1.0 mass % or more and 35 mass % or less 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 or more and 90/10 or less.

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 or more and 20,000 or less.

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

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 mol % or more and 20 mol % or less.

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

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

10 . A method of producing a toner, wherein
the method comprises 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, the toner comprises a toner particle containing a binder resin, the binder resin comprises the 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 comprises a unit derived from a monomer (a) and a unit derived from a monomer (b), the monomer (a) is one or more selected from the group consisting of the monomer group A described below; and the monomer (b) is one or more selected from the group consisting of the monomer group B described below; the crystalline polyester segment has a content X (mol %) of the unit derived from the monomer (b), as calculated from the following formula (1), of 1.0 mol % or more and 24 mol % or less:
X={Mb /( Ma+Mb )}×100  (1)

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° C. or more and 85° C. or less:
monomer group A:
an α,ω-straight-chain aliphatic diol having 2 or more and 11 or less carbon atoms;
an α,ω-straight-chain aliphatic dicarboxylic acid having 2 or more and 13 or less carbon atoms;
an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 2 or more and 12 or less carbon atoms;
an intramolecular acid anhydride of an α,ω-straight-chain aliphatic dicarboxylic acid having 2 or more and 13 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic dicarboxylic acid having 2 or more and 13 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 2 or more and 12 or less carbon atoms; and
a lactonized compound of an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 2 or more and 12 or less carbon atoms,
monomer group B:
an α,ω-straight-chain aliphatic diol having 12 or more and 22 or less carbon atoms;
an α,ω-straight-chain aliphatic dicarboxylic acid having 14 or more and 24 or less carbon atoms;
an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 13 or more and 23 or less carbon atoms;
an intramolecular acid anhydride of an α,ω-straight-chain aliphatic dicarboxylic acid having 14 or more and 24 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic dicarboxylic acid having 14 or more and 24 or less carbon atoms;
an alkyl ester of an α,ω-straight-chain aliphatic monohydroxymonocarboxylic acid having 13 or more and 23 or less carbon atoms; and
a lactonized compound of an α,ω-straight-chain aliphat

Assignees

• Canon Kk

Inventors

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

Classifications

• G03G9/08711

  with esters of acrylic or methacrylic acid · 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

• G03G9/08755

  Polyesters · CPC title

• G03G9/0806

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