Compound having azo skeleton and pigment dispersant, pigment composition, pigment dispersion, and toner containing the compound

Patent metadata

Field	Value
Publication number	US-9470995-B2
Application number	US-201314381192-A
Country	US
Kind code	B2
Filing date	Feb 20, 2013
Priority date	Feb 29, 2012
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

To provide an azo compound which improves the dispersibility of an azo pigment in a non-water soluble solvent.
The purpose is achieved by an azo compound having a specific structure in which a high molecular weight polymer unit is bonded.

First claim

The invention claimed is:

1. An azo compound comprising:
a partial structure represented by the following Formula (A) or Formula (B) and
a polymer unit,
wherein
the polymer unit bonds to the partial structure and has a repeating unit represented by Formula (2) and has a number average molecular weight of 500 or more and 200000 or less,

wherein, in Formula (A),
R 1 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, or a cyano group,
R 2 and R 2 ′ represents an alkyl group having 1 to 6 carbon atoms, a phenyl group, an alkoxy group having 1 to 6 carbon atoms, or an amino group,
R 3 to R 7 , and R 3 ′ to R 7 ′ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, or a linking group, the linking group is bonded to the polymer, and at least one of R 3 to R 7 and at least one of R 3 ′ to R 7 ′ are is the linking group;

wherein, in Formula (B),
R 1 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, or a cyano group,
R 2 , R 2 ′, and R 2 ″, represent an alkyl group having 1 to 6 carbon atoms a phenyl group, an alkoxy group having 1 to 6 carbon atoms, or an amino group,
R 3 to R 7 , R 3 ′ to R 7 ′, and R 3 ″ to R 7 ″ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, a cyano group, or a linking group, the linking group is bonded to the polymer, and at least one of R 3 to R 7 , at least one of R 3 ′ to R 7 ′, and at least one of R 3 ″ to R 7 ″ are the linking group;

In Formula (2), R 8 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms and R 9 represents a phenyl group, a carboxyl group, a carboxylic acid ester group, or a carboxylic acid amide group.

2. The azo compound according to claim 1 , wherein R 2 is a methyl group.

3. The azo compound according to claim 1 , wherein R 1 is a hydrogen atom.

4. The azo compound according to claim 1 , wherein the linking group has an amide bond or an ester bond.

5. A pigment dispersant, comprising the azo compound according to claim 1 .

6. A pigment composition, comprising the pigment dispersant of claim 5 and an azo pigment.

7. The pigment composition according to claim 6 , wherein the azo pigment is an acetanilide pigment.

8. The pigment composition according to claim 6 , wherein the azo pigment is an azo pigment represented by the following Formula (3)

9. A pigment dispersion, comprising the pigment composition according to claim 6 and a non-water soluble solvent.

10. The pigment dispersion according to claim 9 , wherein the non-water soluble solvent is a styrene monomer.

11. A toner, comprising toner particles each of which contains a binder resin, a colorant, and a wax component, wherein the colorant is the pigment composition according to claim 6 .

12. The toner according to claim 11 , wherein the toner particles are manufactured by a suspension polymerization method or a suspension granulation method.

Assignees

• Canon Kk

Inventors

• Seki Masanori
• Hasegawa Yuki
• Hasegawa Waka
• Kawamura Masashi
• Watanabe Taiki
• Nishiura Chiaki
• Toyoda Takayuki
• Mashida Ayano
• Murai Yasuaki
• Hirose Masashi

Classifications

• C09B67/0055

  Mixtures of two or more disazo dyes · CPC title

• C09B33/153

  in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide) · CPC title

• G03G9/08795

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

• C09D17/003

  containing an organic pigment (process features in the making of dye stuff preparations C09B67/00) · CPC title

• G03G9/091 Primary

  Azo dyes · CPC title