Compound having azo skeleton structure, pigment-dispersing agent, pigment composition, pigment dispersion, and toner

Patent metadata

Field	Value
Publication number	US-9625845-B2
Application number	US-201414787460-A
Country	US
Kind code	B2
Filing date	Apr 24, 2014
Priority date	Apr 30, 2013
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

The present invention provides a compound capable of improving the dispersibility of yellow, magenta, cyan, and black pigments in a water-insoluble solvent and a pigment-dispersing agent. The present invention also provides a pigment composition, a pigment dispersion, and a toner, which have satisfactory tinting strength. The present invention relates to a compound having a structure in which an azo skeleton structure is bound to a polymer portion via a linking group in the azo skeleton structure.

First claim

The invention claimed is:

1. A compound comprising:
a structure in which a moiety represented by the following formula (1) is bound to a polymer portion having a monomer unit represented by the following formula (2) via a linking group in the moiety,

wherein in the formula (1),
Ar 1 represents
an unsubstituted aryl group, or
an aryl group substituted with at least one group selected from the group consisting of an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a cyano group, a trifluoromethyl group, a carboxy group, a carboxylate group, a carboxamide group, an SOOR 9 group, an NR 10 SOOR 11 group, and the linking group,
R 1 represents an alkyl group, a phenyl group, or the linking group,
R 2 to R 6 each independently represent a hydrogen atom, an SOOR 60 group, an NR 61 SOOR 62 group, or the linking group,
R 9 and R 60 each independently represent an OR 12 group, an NR 13 R 14 group, or an NR 15 CONR 16 R 17 group,
R 10 , R 61 , and R 15 each independently represent a hydrogen atom or an alkyl group,
R 11 and R 62 each independently represent an alkyl group, a phenyl group, or an aralkyl group,
R 12 represents a hydrogen atom, an alkyl group, a phenyl group, an aralkyl group, an alkali metal ion, or a quaternary ammonium ion,
R 13 and R 14 each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group,
R 16 and R 17 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group,
Ar 1 and R 2 to R 6 satisfy at least one of requirements i) and ii) described below,
i) Ar 1 represents an aryl group having the substituent, the aryl group having an SOOR 9 group or an NR 10 SOOR 11 group serving as the substituent, and
ii) at least one of R 2 to R 6 represents an SOOR 60 group or an NR 61 SOOR 62 group, and wherein
at least one group selected from the group consisting of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and the substituent of Ar 1 in the case that Ar 1 represents an aryl group having the substituent, is the linking group; and

wherein in the formula (2),
R 7 represents a hydrogen atom or an alkyl group, and
R 8 represents a phenyl group, a carboxy group, a carboxylate group, or a carboxamide group.

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

wherein in the formula (3),
R 1 represents an alkyl group, a phenyl group, or the linking group,
R 2 to R 6 each independently represent a hydrogen atom, an SOOR 60 group, an NR 61 SOOR 62 group, or the linking group,
R 18 to R 22 each independently represent a hydrogen atom, an SOOR 9 group, an NR 10 SOOR 11 group, or the linking group,
R 9 and R 60 each independently represent an OR 12 group, an NR 13 R 14 group, or an NR 15 CONR 16 R 17 group,
R 10 , R 61 , and R 15 each independently represent a hydrogen atom or an alkyl group,
R 11 and R 62 each independently represent an alkyl group, a phenyl group, or an aralkyl group,
R 12 represents a hydrogen atom, an alkyl group, a phenyl group, an aralkyl group, an alkali metal ion, or a quaternary ammonium ion,
R 13 and R 14 each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group,
R 16 and R 17 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group,
R 2 to R 6 and R 18 to R 22 satisfy at least one of requirements i) and ii) described below,
i) at least one of R 2 to R 6 represents an SOOR 61 group or an NR 61 SOOR 62 group, and
ii) at least one of R 18 to R 22 represents an SOOR 9 group or an NR 10 SOOR 11 group, and
at least one of R 1 to R 6 and R 18 to R 22 represents the linking group.

3. The compound according to claim 1 , wherein at least one substituent of Ar 1 in the formula (1) is a group represented by the formula (2).

4. The compound according to claim 1 , wherein at least one substituent of Ar 1 in the formula (1) is an SOOR 9 group or an NR 10 SOOR 11 group.

5. The compound according to claim 4 , wherein at least one substituent of Ar 1 in the formula (1) is an SOOR 9 group, and R 9 represents an NR 13 R 14 group.

6. The compound according to claim 1 , wherein at least one of R 2 to R 6 in the formula (1) represents the linking group.

7. A pigment-dispersing agent comprising:
the compound according to claim 1 .

8. A pigment composition comprising:
the pigment-dispersing agent according to claim 7 ; and
a pigment.

9. A pigment dispersion comprising:
the pigment composition according to claim 8 ; and
a water-insoluble solvent.

10. The pigment dispersion according to claim 9 , wherein the water-insoluble solvent is styrene.

11. A toner comprising:
toner particles, each of which contains
a binder resin, and
a colorant,

wherein the colorant is the pigment composition according to claim 8 .

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

Assignees

• Canon Kk

Inventors

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

Classifications

• C08F8/34

  Introducing sulfur atoms or sulfur-containing groups · CPC title

• C09B29/337

  Carbocyclic arylides · CPC title

• C09B33/153

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

• C09B69/106

  containing an azo dye · CPC title

• G03G9/091 Primary

  Azo dyes · CPC title