Pigment dispersion and toner

Patent metadata

Field	Value
Publication number	US-2016246200-A1
Application number	US-201615044745-A
Country	US
Kind code	A1
Filing date	Feb 16, 2016
Priority date	Feb 20, 2015
Publication date	Aug 25, 2016
Grant date	—

Abstract

A pigment dispersion containing a pigment, a non-water-soluble solvent, a compound in which an specific azo skeleton structure is bonded to a specific polymer having a monomer unit given, and a polymer compound having a monomer unit that contains a structure selected from the partial structures given by the specific formulas (3) and (4).

First claim

What is claimed is:

1 . A pigment dispersion comprising:
a pigment; a non-water-soluble solvent; a compound having:
a partial structure represented by formula (1) and
a polymer having a monomer unit represented by formula (2); and
a polymer compound having a monomer unit comprising at least one structure selected from the group consisting of partial structures represented by formulas (3) and (4)

[in formula (1), R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an OR 5 group, or an NR 6 R 7 group;
R 5 to R 7 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or an aralkyl group; and
Ar represents a substituted or unsubstituted aryl group;
wherein at least one of R 1 , R 2 , and Ar has a substituent that has a site bonded to the polymer]

[in formula (2), R 3 represents a hydrogen atom or an alkyl group and
R 4 represents a substituted or unsubstituted phenyl group, a carboxy group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted carboxamide group]

[in formula (3), R 8 to R 11 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a carboxy group, a sulfo group, a C 1-18 alkyl group, a C 1-18 alkoxy group, or an organic group as required to form a ring with an adjacent position, wherein at least one of R 8 to R 11 has a substituent that has a site bonded to a main chain or a side chain in the polymer compound, and M 1 and M 2 each independently represent a hydrogen atom, a metal atom, or NH 4 ]

[in formula (4), R 12 to R 16 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, or an alkoxy group, wherein at least one of R 12 to R 16 has a substituent that has a site bonded to a main chain or a side chain in the polymer compound, and M 3 represents a hydrogen atom, a metal atom, or NH 4 ].

2 . The pigment dispersion according to claim 1 , wherein an azo skeleton structure represented by formula (1) is represented by formula (5)

[in formula (5), R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an OR 5 group, or an NR 6 R 7 group;
Ar represents a substituted or unsubstituted aryl group;
R 5 to R 7 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or an aralkyl group;
R 17 to R 21 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a carboxy group, a COOR 22 group, or a CONR 23 R 24 group, SO 2 NR 25 R 26 , a group represented by formula (6-1), a group represented by formula (6-2), or a substituent having a site bonded to the polymer having a monomer unit with formula (2); and
R 22 to R 26 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group;
wherein at least one of Ar, R 1 , and R 17 to R 21 has a substituent that has a site bonded to the polymer]

[in formula (6-1), R 27 represents a hydrogen atom, a substituted or unsubstituted alkyl group, an aralkyl group, a substituted or unsubstituted alkyloxycarbonyl group, or a substituted or unsubstituted aralkyloxycarbonyl group;
Z 1 represents an oxygen atom, a sulfur atom, or an NR 28 group;
R 28 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyloxycarbonyl group, or a substituted or unsubstituted aralkyloxycarbonyl group; and
“*” represents a site bonded to an R 17 -to-R 21 -bearing aromatic ring of formula (5);
in formula (6-2), the “*” and “**” represent a site bonded to the R 17 -to-R 21 -bearing aromatic ring of formula (5);
the group represented by formula (6-2) forms a 5-membered heterocycle through bonding to the R 17 -to-R 21 -bearing aromatic ring in formula (5); and
Z 2 represents an oxygen atom, a sulfur atom, or an NR 28 group].

3 . The pigment dispersion according to claim 2 , wherein the azo skeleton structure represented by formula (1) is represented by formula (7)

[in formula (7),
R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an OR 5 group, or an NR 6 R 7 group;
R 5 to R 7 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or an aralkyl group;
R 17 to R 21 and R 29 to R 33 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a carboxy group, a COOR 22 group, or a CONR 23 R 24 group, SO 2 NR 25 R 26 , a group represented by formula (6-3), a group represented by formula (6-4), or a substituent having a site bonded to the polymer having a monomer unit with formula (2); and
R 22 to R 26 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group;
wherein at least one of R 17 to R 21 and R 29 to R 33 is a substituent that has a site bonded to the polymer]

[in formula (6-3), R 27 represents a hydrogen atom, a substituted or unsubstituted alkyl group, an aralkyl group, a substituted or unsubstituted alkyloxycarbonyl group, or a substituted or unsubstituted aralkyloxycarbonyl group;
Z 1 represents an oxygen atom, a sulfur atom, or an NR 28 group;
R 28 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyloxycarbonyl group, or a substituted or unsubstituted aralkyloxycarbonyl group; and
“*” represents a site bonded to an R 17 -to-R 21 -bearing aromatic ring or the R 29 -to-R 33 -bearing aromatic ring of formula (7);
in formula (6-4), “*” and “**” each represent a site bonded to the R 17 -to-R 21 -bearing aromatic ring or the R 29 -to-R 33 -bearing aromatic ring of formula (7);
the group represented by formula (6-4) forms a 5-membered heterocycle through bonding to the R 17 -to-R 21 -bearing aromatic ring or the R 29 -to-R 33 -bearing aromatic ring in formula (7); and
Z 2 represents an oxygen atom, a sulfur atom, or an NR 28 group].

4 . The pigment dispersion according to claim 1 , wherein an azo skeleton structure represented by formula (1) is bonded to the polymer having a monomer unit represented by formula (2) by a substituent having an alkoxycarbonyl group or a carboxamide group.

5 . The pigment dispersion according to claim 1 , wherein the polymer compound having a monomer unit comprising a structure selected from the partial structures represented by formulas (3) and (4) further has a monomer unit represented by formula (8) or (9)

Assignees

• Canon Kk

Inventors

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

Classifications

• G03G9/0904

  Carbon black · CPC title

• G03G9/092

  Quinacridones · CPC title

• C08K5/23

  Azo-compounds · CPC title

• C08K3/04

  Carbon · CPC title

• C08K5/30

  Hydrazones; Semicarbazones · CPC title