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

Patent metadata

Field	Value
Publication number	US-9926450-B2
Application number	US-201414914961-A
Country	US
Kind code	B2
Filing date	Aug 27, 2014
Priority date	Aug 29, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

The present invention provides a compound capable of improving the dispersibility of color 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 provides the compound containing a polymer having a monomer unit having a specific chemical structure, the compound having a moiety also having a specific structure.

First claim

The invention claimed is:

1. A compound containing a polymer having a monomer unit represented by the following formula (4), and having a moiety represented by the following formula (1),

wherein in the formula (1),
R 1 represents an alkyl group or a phenyl group,
Ar 1 represents an aryl group,
Ar 1 and R 2 to R 6 satisfy at least one of requirements (i) and (ii) described below,
(i) Ar 1 has a linking group which is bound to a carbon atom in the aryl group, and constitutes a bonding moiety with the polymer,
(ii) at least one of R 2 to R 6 has a linking group constituting a bonding moiety with the polymer,

when none of R 2 to R 6 has a linking group, R 2 to R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a cyano group, a trifluoromethyl group, a carboxy group, a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, or an NHR 11 group,
R 7 to R 11 each independently represent a group represented by the following formula (2) or (3), and
wherein Ar 1 and R 2 to R 6 satisfy at least one of requirements (iii) and (iv) described below,
(iii) Ar 1 has a substituent selected from a CONHR 7 group, a COOR 8 group, a NHCOR 9 group, an OCOR 10 group, and an NHR 11 group,
(iv) at least one of R 2 to R 6 represents a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, and an NHR 11 group,

wherein in the formula (2),
R 12 represents a COR 14 group or an SO 2 R 15 group,
R 14 and R 15 each independently represent an OR 16 group or an NR 17 R 18 group,
R 16 represents a hydrogen atom, an alkyl group, a phenyl group, an aralkyl group, or a cation that forms a salt with a carboxylate anion or a sulfonate anion,
R 17 and R 18 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group, and
n represents an integer of 1 to 11,

wherein in the formula (3),
R 13 represents a COR 14 group or an SO 2 R 15 group,
R 14 and R 15 each independently represent an OR 16 group or an NR 17 R 18 group,
R 16 represents a hydrogen atom, an alkyl group, a phenyl group, an aralkyl group, or a cation that forms a salt with a carboxylate anion or a sulfonate anion, and
R 17 and R 18 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group,

wherein in the formula (4),
R 19 represents a hydrogen atom or an alkyl group, and
R 20 represents a phenyl group, a carboxy group, a carboxylate group, or a carboxamide group.

2. The compound according to claim 1 , wherein the moiety represented by the formula (1) has a structure represented by the following formula (5):

wherein in the formula (5),
R 1 represents an alkyl group or a phenyl group,
R 21 to R 25 and R 2 to R 6 satisfy at least one of requirements (v) and (vi) described below,
(v) at least one of R 21 to R 25 has a linking group constituting a bonding moiety with the polymer,
(vi) at least one of R 2 to R 6 has a linking group constituting a bonding moiety with the polymer,

when none of R 21 to R 25 and R 2 to R 6 has a linking group, R 21 to R 25 and R 2 to R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a cyano group, a trifluoromethyl group, a carboxy group, a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, or an NHR 11 group, and
R 7 to R 11 each represent a group represented by the formula (2) or (3), and
wherein R 21 to R 25 and R 2 to R 6 satisfy at least one of requirements (vii) and (viii) described below,
(vii) at least one of R 21 to R 25 represents one of a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, and an NHR 11 group, and
(viii) at least one of R 2 to R 6 represents one of a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, and an NHR 11 group.

3. The compound according to claim 1 , wherein the linking group has a carboxylate linkage or a carboxamide linkage.

4. The compound according to claim 1 , wherein Ar 1 and R 2 to R 6 in the formula (1) satisfy at least one of requirements (ix) and (x) described below,
(ix) Ar 1 has, as a substituent, one of a CONHR 7 group and a COOR 8 group, and
(x) at least one of R 2 to R 6 represents one of a CONHR 7 group and a COOR 8 group.

5. The compound according to claim 1 , wherein Ar 1 in the formula (1) satisfies requirement (iii).

6. The compound according to claim 1 , wherein R 2 to R 6 in the formula (1) satisfy requirement (ii).

7. The compound according to claim 1 , wherein R 14 and R 15 in the formula (2) or (3) each represents an NH 2 group.

8. The compound according to claim 1 , wherein R 12 and R 13 in the formula (2) or (3) represents an SO 2 R 15 group.

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

10. A pigment composition comprising:
the compound according to claim 1 ; and
a pigment.

11. A pigment dispersion comprising:
the pigment composition according to claim 10 ; and
a water-insoluble solvent.

12. The pigment dispersion according to claim 11 , wherein the water-insoluble solvent is styrene.

13. A toner comprising:
toner particles each containing
a binder resin; and
a colorant,

wherein the colorant is the pigment composition according to claim 10 .

14. The toner according to claim 13 , wherein the toner particles are produced by a suspension polymerization method or a suspension granulation method.

15. The compound according to claim 1 , wherein the moiety represented by the formula (1) has a structure represented by the following formula (5):

wherein in the formula (5),
R 1 represents an alkyl group or a phenyl group,
only one of R 2 to R 6 has a linking group constituting a bonding moiety with the polymer,
when none of R 2 to R 6 has a linking group, R 2 to R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a cyano group, a trifluoromethyl group, a carboxy group, a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, or an NHR 11 group,
R 21 to R 25 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a cyano group, a trifluoromethyl group, a carboxy group, a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, or an NHR 11 group, and
R 7 to R 11 each represent a group represented by the formula (2) or (3), and
at least one of R 21 to R 25 represents one of a CONHR 7 group, a COOR 8 group, an NHCOR 9 group, an OCOR 10 group, and an NHR 11 group.

16. The compound according to claim 15 , wherein the linking group has a carboxylate linkage or a carboxamide linkage.

Assignees

• Canon Kk

Inventors

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

Classifications

• C09B67/0041

  mixtures containing one azo dye · CPC title

• C09B67/009 Primary

  polymeric dispersing agent · CPC title

• C08F212/08

  Styrene · CPC title

• C09B69/106

  containing an azo dye · CPC title

• C09B67/0046

  Mixtures of two or more azo dyes · CPC title