Compound having azo skeleton, pigment dispersant, pigment composition, pigment dispersion, and toner

Patent metadata

Field	Value
Publication number	US-10087328-B2
Application number	US-201414915160-A
Country	US
Kind code	B2
Filing date	Aug 28, 2014
Priority date	Aug 29, 2013
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

Abstract

A compound that improves the dispersibility of pigments in non-water-soluble solvents is provided, the compound having a pigment dispersant, a pigment composition, a pigment dispersion, and a toner wherein the compound has a polymer and a monoazo compound having a certain structure binding to each other.

First claim

The invention claimed is:

1. A compound comprising a polymer having a monomer unit represented by formula (3), wherein the compound has a partial structure represented by formula (1):

wherein
R 1 represents an alkyl group or a phenyl group,
Ar represents an aryl group, and
Ar and R 2 to R 6 meet at least one of conditions (i) and (ii):
(i) Ar has a linking group that binds to a carbon atom of the aryl group and forms a linking portion where the partial structure binds to the polymer;
(ii) at least one of R 2 to R 6 is a linking group that forms a linking portion where the partial structure binds to the polymer;
each of R 2 to R 6 , when not being the linking group, independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a cyano group, a trifluoromethyl group, a carboxyl group, a group represented by formula (2-1), or a group represented by formula (2-2); and

Ar has a group represented by formula (2-1) or a group represented by formula (2-2) as a substituent;

wherein
the symbol * represents a site where the group binds to Ar or the aromatic ring having R 2 to R 6 in formula (1),

R 7 represents a hydrogen atom, an alkyl group, an aralkyl group, an alkyloxycarbonyl group, or an aralkyloxycarbonyl group, and
A 1 represents an oxygen atom, a sulfur atom, or an NR 8 group,
where R 8 represents a hydrogen atom, an alkyloxycarbonyl group, or an aralkyloxycarbonyl group;

wherein
the symbols * and ** represent sites where the group binds to Ar or the aromatic ring having R 2 to R 6 in formula (1),
the group represented by formula (2-2) forming a five-member heterocycle by binding to Ar or the aromatic ring having R 2 to R 6 in formula (1), and
A 2 represents an oxygen atom, a sulfur atom, or an NR 16 group,
where R 16 represents a hydrogen atom, an alkyloxycarbonyl group, or an aralkyloxycarbonyl group:

wherein

R 9 represents a hydrogen atom or an alkyl group, and
R 10 represents a phenyl group, a carboxyl group, a carboxylic acid ester group,
or a carboxylic acid amide group.

2. The compound according to claim 1 , wherein the partial structure represented by formula (1) is a structure represented by formula (4):

wherein
R 1 represents an alkyl group or a phenyl group, and
R 11 to R 15 and R 2 to R 6 meet at least one of conditions (v) and (vi):
(v) at least one of R 11 to R 15 is a linking group that forms a linking portion where the partial structure binds to the polymer;
(vi) at least one of R 2 to R 6 is a linking group that forms a linking portion where the partial structure binds to the polymer;
each of R 11 to R 15 and R 2 to R 6 , when not being the linking group, independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a cyano group, a trifluoromethyl group, a carboxyl group, a group represented by formula (2-1), or a group represented by formula (2-2); and

at least one of R 11 to R 15 is a group represented by formula (2-1) or a group represented by formula (2-2).

3. The compound according to claim 1 , wherein the linking group has a carboxylic acid ester bond or a carboxylic acid amide bond.

4. The compound according to claim 1 , wherein: the partial structure represented by formula (1) has a group represented by formula (2-2); and A 2 in formula (2-2) is an oxygen atom.

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

6. A pigment composition comprising the compound according to claim 1 and a pigment.

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

8. The pigment dispersion according to claim 7 , wherein the non-water-soluble solvent is styrene.

9. A toner comprising a toner particle containing a binder resin and a colorant, wherein the colorant is the pigment composition according to claim 6 .

10. The toner according to claim 9 , wherein the toner particle is produced using suspension polymerization or suspension granulation.

11. A compound comprising a polymer having a monomer unit represented by formula (3), wherein the compound has a partial structure represented by formula (1):

wherein
R 1 represents an alkyl group or a phenyl group,
Ar represents an aryl group, and
Ar and R 2 to R 6 meet at least one of conditions (i) and (ii):
(i) Ar has a linking group that binds to a carbon atom of the aryl group and forms a linking portion where the partial structure binds to the polymer;
(ii) at least one of R 2 to R 6 is a linking group that forms a linking portion where the partial structure binds to the polymer;
each of R 2 to R 6 , when not being the linking group, independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a cyano group, a trifluoromethyl group, a carboxyl group, a group represented by formula (2-1), or a group represented by formula (2-2); and
Ar and R 2 to R 6 meet at least one of conditions (iii) and (iv):

(iii) Ar has a group represented by formula (2-1) as a substituent;
(iv) at least one of R 2 to R 6 is a group represented by formula (2-1):

wherein
the symbol * represents a site where the group binds to Ar or the aromatic ring having R 2 to R 6 in formula (1),

R 7 represents a hydrogen atom, an alkyl group, an aralkyl group, an alkyloxycarbonyl group, or an aralkyloxycarbonyl group, and
A 1 represents an oxygen atom

wherein
the symbols * and ** represent sites where the group binds to the aromatic ring having R 2 to R 6 in formula (1),
the group represented by formula (2-2) forming a five-member heterocycle by binding to the aromatic ring having R 2 to R 6 in formula (1), and
A 2 represents an oxygen atom, a sulfur atom, or an NR 16 group,
where R 16 represents a hydrogen atom, an alkyloxycarbonyl group, or an aralkyloxycarbonyl group:

wherein

R 9 represents a hydrogen atom or an alkyl group, and
R 10 represents a phenyl group, a carboxyl group, a carboxylic acid ester group,
or a carboxylic acid amide group.

12. A compound comprising a polymer having a monomer unit represented by formula (3), wherein the compound has a partial structure represented by formula (1

Assignees

• Canon Kk

Inventors

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

Classifications

• G03G9/09

  Colouring agents for toner particles · CPC title

• C08F112/08

  Styrene · CPC title

• G03G9/0926

  characterised by physical or chemical properties · CPC title

• C08F2810/50

  wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority · CPC title

• C09B69/106

  containing an azo dye · CPC title