Toner and method for manufacturing toner particles

Patent metadata

Field	Value
Publication number	US-9176407-B2
Application number	US-201214357163-A
Country	US
Kind code	B2
Filing date	Nov 8, 2012
Priority date	Nov 10, 2011
Publication date	Nov 3, 2015
Grant date	Nov 3, 2015

Abstract

The present invention provides a toner that contains an azo pigment well-dispersed in a binder resin and has a satisfactory color tone.
The toner contains toner particles each containing a binder resin and a colorant. Each of the toner particles contains a compound having a polyester moiety and a bisazo structure moiety. The colorant is the azo pigment.

First claim

The invention claimed is:

1. A toner, comprising toner particles each containing a binder resin and a colorant,
wherein each of the toner particles contains a compound having a polyester moiety and a bisazo structure moiety represented by the following formula (1) or (2), and
the colorant is an azo pigment:

wherein R 1 to R 4 independently denote a hydrogen atom or a halogen atom,
R 5 and R 6 independently denote an alkyl group having 1 to 6 carbon atoms or a phenyl group,
R 7 to R 11 independently denote a hydrogen atom, a COOR 12 group, or a CONR 13 R 14 group, provided that at least one of R 7 to R 11 denotes the COOR 12 group or the CONR 13 R 14 group,
R 12 to R 14 independently denote a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and
L 1 denotes a divalent linking group to be bonded to the polyester moiety.

2. The toner according to claim 1 , wherein R 5 and R 6 denote a methyl group.

3. The toner according to claim 1 , wherein R 7 and R 10 denote COOR 12 , and R 8 , R 9 , and R 11 denote a hydrogen atom.

4. The toner according to claim 1 , wherein L 1 denotes a linking group having a carboxylate bond, a carboxylic acid amide bond, or a sulfonate bond.

5. The toner according to claim 1 , wherein the compound has the bisazo structure moiety having the formula (1), and the bisazo structure moiety having the formula (1) has the following formula (7)

6. The toner according to claim 1 , wherein the azo pigment is an acetoacetanilide pigment.

7. The toner according to claim 6 , wherein the acetoacetanilide pigment has the following formula (8)

8. A method for manufacturing toner particles, comprising: dispersing a polymerizable monomer composition containing a pigment composition and a polymerizable monomer in an aqueous medium, forming particles of the polymerizable monomer composition, and polymerizing the polymerizable monomer in the particles to manufacture toner particles,
wherein the pigment composition contains an azo pigment and a compound having a polyester moiety and a bisazo structure moiety represented by the following formula (1) or (2):

wherein R 1 to R 4 independently denote a hydrogen atom or a halogen atom,
R 5 and R 6 independently denote an alkyl group having 1 to 6 carbon atoms or a phenyl group,
R 7 to R 11 independently denote a hydrogen atom, a COOR 12 group, or a CONR 13 R 14 group, provided that at least one of R 7 to R 11 denotes the COOR 12 group or the CONR 13 R 14 group,
R 12 to R 14 independently denote a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and
L 1 denotes a divalent linking group to be bonded to the polyester moiety.

9. A method for manufacturing toner particles, comprising: dispersing a resin solution containing a pigment composition, a binder resin, and a solvent in an aqueous medium, forming particles from the resin solution to produce a suspension, and removing the solvent from the suspension to manufacture toner particles,
wherein the pigment composition contains an azo pigment and a compound having a polyester moiety and a bisazo structure moiety represented by the following formula (1) or (2):

wherein R 1 to R 4 independently denote a hydrogen atom or a halogen atom,
R 5 and R 6 independently denote an alkyl group having 1 to 6 carbon atoms or a phenyl group,
R 7 to R 11 independently denote a hydrogen atom, a COOR 12 group, or a CONR 13 R 14 group, provided that at least one of R 7 to R 11 denotes the COOR 12 group or the CONR 13 R 14 group,
R 12 to R 14 independently denote a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and
L 1 denotes a divalent linking group to be bonded to the polyester moiety.

Assignees

• Canon Kk

Inventors

• Hasegawa Yuki
• Murai Yasuaki
• Tanaka Masatake
• Toyoda Takayuki
• Kawamura Masashi
• Hasegawa Waka
• Hirose Masashi

Classifications

• G03G9/0806

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

• G03G9/08768

  Other polymers having nitrogen in the main chain, with or without oxygen or carbon only · CPC title

• G03G9/08755

  Polyesters · CPC title

• G03G9/08791

  characterised by the presence of specified groups or side chains · CPC title

• G03G9/091 Primary

  Azo dyes · CPC title