Toner and method for producing toner

Patent metadata

Field	Value
Publication number	US-9964879-B2
Application number	US-201715457054-A
Country	US
Kind code	B2
Filing date	Mar 13, 2017
Priority date	Mar 18, 2016
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

Provided is a toner comprising a toner particle containing a binder resin, a resin A, and a pigment, wherein the resin A has a pKa of at least 6.0 and not more than 9.0, and also has a hydrophobic parameter HPA of at least 0.65 and not more than 0.95.

First claim

What is claimed is:

1. A toner comprising a toner particle containing:
a binder resin;
a resin A; and
a pigment, wherein
the resin A has a pKa of 6.0 to 9.0 where pKa represents an acid dissociation constant measured by preparing a resin solution in which 1.0 part by mass of the resin A, 70.0 parts by mass of toluene and 30.0 parts by mass of ethanol are mixed, and carrying out neutralization titration with a 0.1 mol/L potassium hydroxide ethanol solution, and
the resin A has a hydrophobic parameter HPA of 0.65 to 0.95 where HPA represents a volume fraction of heptane at a point of precipitation by the resin A as measured by the addition of heptane to a solution containing 0.01 parts by mass of the resin A and 1.48 parts by mass of chloroform.

2. The toner according to claim 1 , wherein the resin A has a structure represented by formula (1)

where one of R 2 and R 3 is a carboxyl group; R 1 , R 2 , R 3 , R 4 , and R 5 other than the carboxyl group are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms; L is a linker group represented by formula (2); and * represents a segment bonded to a main chain skeleton of the resin A,

where a is 0 or 1, and b is an integer of 0 to 4; X is a single bond or a group represented by —O—, —S—, or —NR 6 —; R 6 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and * represents a segment bonded to the main chain skeleton of the resin A.

3. The toner according to claim 2 , wherein the structure represented by the formula (1) is a structure represented by formula (3)

where one of R 8 and R 9 is a carboxyl group, and the other is a hydroxyl group; R 7 , R 10 , and R 11 are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; and * represents a segment bonded to the main chain skeleton of the resin A.

4. The toner according to claim 1 , wherein the resin A has an acid value of 3.0 to 25.0 mg KOH/g.

5. The toner according to claim 1 , wherein a content of the resin A is 3.0 to 30.0 parts by mass per 100 parts by mass of the pigment.

6. The toner according to claim 1 , wherein a weight-average molecular weight of the resin A is 10,000 to 75,000.

7. The toner according to claim 1 , wherein the resin A has the pKa of 7.0 to 8.0.

8. The toner according to claim 1 , wherein
the binder resin includes at least 50 parts by mass of a resin B when a resin component in the toner is taken as 100 parts by mass, and
a difference (HPB−HPA) between the hydrophobic parameter HPA of the resin A and a hydrophobic parameter HPB of the resin B is 0.10 to 0.25, where HPB represents a volume fraction of heptane at a point of precipitation by the resin B as measured by the addition of heptane to a solution containing 0.01 parts by mass of the resin B and 1.48 parts by mass of chloroform.

9. The toner according to claim 1 , wherein the pigment is at least one selected from the group consisting of carbon black, a phthalocyanine pigment, a quinacridone pigment, a pyrrolopyrrole pigment, a perylene pigment, an anthraquinone pigment, and an isoindoline pigment.

10. The toner according to claim 1 , wherein the resin A has an alkoxycarbonyl group represented by formula (5)

in the formula (5), n is 3 to 21; and ** represents a segment bonded to a main chain skeleton of the resin A.

11. A method for producing a toner comprising a toner particle containing a binder resin, a resin A and a pigment, the method comprising step (i) or (ii):
(i) a step of producing the toner particle by granulating, in an aqueous medium, a polymerizable monomer composition containing the resin A, the pigment, and a vinyl polymerizable monomer capable of forming the binder resin, and polymerizing the vinyl polymerizable monomer contained in the polymerizable monomer composition; and
(ii) a step of producing the toner particle by granulating, in an aqueous medium, an organic solvent dispersion containing the binder resin, the resin A, and the pigment in an organic solvent, wherein
the resin A has a pKa of 6.0 to 9.0 where pKa represents an acid dissociation constant measured by preparing a resin solution in which 1.0 part by mass of the resin A, 70.0 parts by mass of toluene and 30.0 parts by mass of ethanol are mixed, and carrying out neutralization titration with a 0.1 mol/L potassium hydroxide ethanol solution, and
the resin A has a hydrophobic parameter HPA of 0.65 to 0.95 HPA represents a volume fraction of heptane at a point of precipitation by the resin A as measured by the addition of heptane to a solution containing 0.01 parts by mass of the resin A and 1.48 parts by mass of chloroform.

12. A toner comprising a toner particle containing:
a binder resin;
a pigment; and
a resin A, wherein
the resin A has a hydrophobic parameter HPA of 0.65 to 0.95, where HPA represents a volume fraction of heptane at a point of precipitation by the resin A as measured by the addition of heptane to a solution containing 0.01 parts by mass of the resin A and 1.48 parts by mass of chloroform, and
the resin A has a structure represented by formula (3)

where one of R 8 and R 9 is a carboxyl group, and the other is a hydroxyl group; R 7 , R 10 , and R 11 are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; and * represents a segment bonded to a main chain skeleton of the resin A.

Assignees

• Canon Kk

Inventors

• Terui Yuhei
• Yoshida Yu
• Kubo Haruko
• Itabashi Hitoshi

Classifications

• G03G9/08711 Primary

  with esters of acrylic or methacrylic acid · CPC title

• G03G9/0804

  whereby the components are brought together in a liquid dispersing medium · CPC title

• G03G9/08755

  Polyesters · CPC title

• G03G9/0904

  Carbon black · CPC title

• G03G9/0918

  Phthalocyanine dyes · CPC title