Toner and method for producing toner

Patent metadata

Field	Value
Publication number	US-10012922-B2
Application number	US-201715456833-A
Country	US
Kind code	B2
Filing date	Mar 13, 2017
Priority date	Mar 18, 2016
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

A toner comprising a toner particle containing a pigment, a resin A and a resin B, wherein the pigment is a pigment having a structure derived from a basic compound, the resin A has an acidic functional group, the resin B has an acid value of at least 2.0 mg KOH/g, the resin B has a glass transition temperature TgB of at least 50° C., and the hydrophobic parameter HPA of the resin A and the hydrophobic parameter of the resin B satisfy the following formulae:

HPA ≥0.60

HPB ≤0.70

HPA−HPB >0.

First claim

What is claimed is:

1. A toner comprising a toner particle, the toner particle comprising:
a binder resin;
a pigment having a structure derived from a basic compound;
a resin A having an acidic functional group, the content of resin A being 1.0 to 30.0 mass parts per 100 mass parts of the pigment; and
a resin B having an acid value of at least 2.0 mg KOH/g and a glass transition temperature TgB of at least 50° C., wherein
a hydrophobic parameter HPA of the resin A and a hydrophobic parameter HPB of the resin B satisfy:
HPA≥0.60 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 mass parts of the resin A and 1.48 mass parts of chloroform,
HPB≤0.70 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 mass parts of the resin B and 1.48 mass parts of chloroform, and
HPA−HPB> 0.

2. The toner according to claim 1 , wherein the pigment has a pKa of 4.0 to 7.0, where pKa is a base dissociation constant measured by preparing a pigment dispersion in which 10.0 mass parts of the pigment, 140.0 mass parts of toluene and 60.0 mass parts of ethanol are mixed, and then subjecting to neutralization titration with a 0.1 mol/L hydrochloric acid ethanol solution.

3. The toner according to claim 1 , wherein the pigment has a base value of 0.9 to 3.0 mg KOH/g.

4. The toner according to claim 1 , wherein the pigment having a structure derived from a basic compound is a pigment containing an organic dye having basic segments, the organic dye having a structure represented by Formula (2):

where P is an organic dye, x is 1 or 2, y is a value of 1 to 4, and each of R 1 and R 2 independently represents a hydrogen atom, or linear or branched alkyl group, or a group needed for forming a heterocycle in which R 1 and R 2 bind together.

5. The toner according to claim 4 , wherein P is an organic dye having a phthalocyanine skeleton or quinacridone skeleton.

6. The toner according to claim 1 , wherein the pigment having a structure derived from a basic compound is a pigment having a basic functional group represented by Formula (8):

where * represents a segment binding to the pigment, z is 1 or 2, and each of R 3 and R 4 independently represents a hydrogen atom, or linear or branched alkyl group, or a group needed for forming a heterocycle in which R 3 and R 4 bind together.

7. The toner according to claim 1 , wherein the acidic functional group of the resin A is a carboxyl group or sulfo group.

8. The toner according to claim 1 , wherein the resin A has a structure represented by Formula (3):

where either R 4 or R 5 is a carboxyl group, while each of the R 3 , R 4 , R 5 , R 6 and R 7 other than the carboxyl group independently represents a hydrogen atom, hydroxy group, amino group, C 1-8 alkoxy group or C 1-8 alkyl group, L is a linking group represented by Formula (4), and * is a segment binding to a main chain skeleton of the resin A;

where a is 0 or 1, b is an integer of 0 to 4, X is a single bond or a group represented by —O—, —S— or —NR 8 —, R 8 is a hydrogen atom or C 1-4 alkyl group, and * is a segment binding to the main chain skeleton of the resin A.

9. The toner according to claim 8 , wherein the structure represented by Formula (3) is represented by Formula (5):

where one of R 10 and R 11 is a carboxyl group, while the other is a hydroxy group, each of R 9 , R 12 and R 13 independently represents a hydrogen atom, hydroxy group, amino group, C 1-4 alkoxy group or C 1-4 alkyl group, and * is a segment binding to the main chain skeleton of the resin A.

10. The toner according to claim 1 , wherein the resin A has a structure represented by Formula (6):

where n is an integer of 3 to 21, and * is a segment binding to a main chain skeleton of the resin A.

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

12. The toner according to claim 1 , wherein the resin A has a weight-average molecular weight (Mw) of 10000 to 75000.

13. The toner according to claim 1 , wherein HPA−HPB≥0.05.

14. The toner according to claim 1 , wherein the content of the resin A is at least 1.0 mass part per 100 mass parts of the resin B.

15. The toner according to claim 1 , wherein the HPB is not more than 0.60.

16. The toner according to claim 1 , wherein the content of the resin A is 1.0 to 70.0 mass parts per 100 mass parts of the resin B.

17. A method for producing a toner comprising a toner particle, the toner particle comprising a binder resin, a pigment having a structure derived from a basic compound, a resin A having an acidic functional group, and a resin B, wherein the method comprises step (i) or step (ii) below:
(i) a step of granulating, in an aqueous medium, a polymerizable monomer composition containing the resin A, the resin B, the pigment and a vinyl polymerizable monomer capable of forming a binder resin, and polymerizing the vinyl polymerizable monomer contained in the polymerizable monomer composition to thereby manufacture the toner particle;
(ii) a step of granulating, in an aqueous medium, an organic solvent dispersion containing the binder resin, the resin A, the resin B and the pigment in an organic solvent, to thereby manufacture the toner particle, wherein
the content of resin A is 1.0 to 30.0 mass parts per 100 mass parts of the pigment,
the resin B has an acid value of at least 2.0 mg KOH/gm and a glass transition temperature TgB of at least 50° C., wherein
a hydrophobic parameter HPA of the resin A and a hydrophobic parameter HPB of the resin B satisfy:
HPA≥0.60 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 mass parts of the resin A and 1.48 mass parts of chloroform,
HPB≤0.70 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 mass parts of the resin B and 1.48 mass parts of chloroform, and
HPA−HPB> 0.

Assignees

• Canon Kk

Inventors

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

Classifications

• G03G9/08755

  Polyesters · CPC title

• G03G9/0806

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

• G03G9/0924 Primary

  Dyes characterised by specific substituents · CPC title

• G03G9/08726

  Polymers of unsaturated acids or derivatives thereof · CPC title

• G03G9/092

  Quinacridones · CPC title