Toner

Patent metadata

Field	Value
Publication number	US-2016246192-A1
Application number	US-201615045589-A
Country	US
Kind code	A1
Filing date	Feb 17, 2016
Priority date	Feb 25, 2015
Publication date	Aug 25, 2016
Grant date	—

Abstract

A toner having a toner particle that contains a binder resin, a pigment, a pigment dispersant, and a crystalline polyester, wherein the pigment dispersant has a specific pigment adsorption segment and a polymer moiety and a hydrophobic parameter HP1 for the pigment dispersant and a hydrophobic parameter HP2 for the crystalline polyester satisfy the formula −0.28≦(HP1−HP2)≦0.15.

First claim

What is claimed is:

1 . A toner comprising a toner particle containing:
a binder resin; a pigment; a pigment dispersant; and a crystalline polyester,
wherein
the pigment dispersant comprises a structure represented by formula (1) and a polymer moiety, and
a hydrophobic parameter HP1 of the pigment dispersant and a hydrophobic parameter HP2 of the crystalline polyester satisfy the following formula,
−0.28≦(HP1−HP2)≦0.15

wherein
HP1 represents a volume fraction of heptane at a point of precipitation by the pigment dispersant as measured by the addition of heptane to a solution containing 0.05 mass parts of the pigment dispersant and 1.48 mass parts of chloroform, and
HP2 represents a volume fraction of heptane at a point of precipitation by the crystalline polyester as measured by the addition of heptane to a solution containing 0.05 mass parts of the crystalline polyester and 1.48 mass parts of chloroform,

wherein in formula (1):
R 1 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group;
Ar represents a substituted or unsubstituted aryl group;
Ar and R 2 to R 6 satisfy at least one of the following conditions (i) and (ii):
(i) Ar has a linking group that is bonded to a carbon atom in the aryl group and that forms a linking portion of bond to the polymer moiety, and
(ii) at least one of R 2 to R 6 is a linking group that forms a linking portion of bond to the polymer moiety;
each of the R 2 to R 6 that is not a linking group independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, an amino group, a cyano group, a trifluoromethyl group, a carboxyl group, or a group represented by the following formula (2-1) or a group represented by the following formula (2-2); and
Ar and R 2 to R 6 satisfy at least one of the following conditions (iii) and (iv):
(iii) Ar has a group represented by formula (2-1) or a group represented by formula (2-2) as a substituent, and
(iv) at least one of R 2 to R 6 is a group represented by formula (2-1) or a group represented by formula (2-2),

wherein in formula (2-1):
* represents a site where the group bonds to the Ar or the aromatic ring having R 2 to R 6 in formula (1);
R 7 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;
A 1 represents an oxygen atom, a sulfur atom, or an NR 8 group; and
R 8 represents a hydrogen atom, a substituted or unsubstituted alkyloxycarbonyl group, or a substituted or unsubstituted aralkyloxycarbonyl group,

wherein in formula (2-2):
* and ** each represent a site where the group bonds to the Ar or the aromatic ring having R 2 to R 6 in formula (1);
the group represented by formula (2-2) forms a 5-membered heterocycle by bonding with the Ar or the aromatic ring having R 2 to R 6 in formula (1);
A 2 represents an oxygen atom, a sulfur atom, or an NR 8 group; and
R 8 represents a hydrogen atom, a substituted or unsubstituted alkyloxycarbonyl group, or a substituted or unsubstituted aralkyloxycarbonyl group.

2 . The toner according to claim 1 , wherein the structure represented by formula (1) is a structure represented by the following formula (3)

wherein in formula (3):
R 1 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group;
R 11 to R 15 and R 2 to R 6 satisfy at least one of the following conditions (v) and (vi):
(v) at least one of R 11 to R 15 is a linking group that forms a linking portion of bond to the polymer moiety, and
(vi) at least one of R 2 to R 6 is a linking group that forms a linking portion of bond to the polymer moiety;
each of the R 11 to R 1 and R 2 to R 6 that is not a linking group independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, an amino group, a cyano group, a trifluoromethyl group, a carboxyl group, a group represented by the formula (2-1), or a group represented by the formula (2-2); and
R 11 to R 15 and R 2 to R 6 satisfy at least one of the following conditions (vii) and (viii):
(vii) at least one of R 11 to R 15 is a group represented by the formula (2-1) or a group represented by the formula (2-2), and
(viii) at least one of R 2 to R 6 is a group represented by the formula (2-1) or a group represented by the formula (2-2).

3 . The toner according to claim 1 , wherein
the pigment dispersant has in a molecule thereof a group represented by the following formula (4), and the number of groups represented by formula (4) per molecule of the pigment dispersant is from 2 to 10,

wherein n in formula (4) represents an integer from 3 to 21.

4 . The toner according to claim 1 , wherein the number of structures represented by formula (1) per molecule of the pigment dispersant is from 1 to 6.

5 . The toner according to claim 1 , wherein the polymer moiety has a monomer unit represented by the following formula (5),

wherein in formula (5):
R 9 represents the hydrogen atom or an alkyl group, and
R 10 represents a substituted or unsubstituted phenyl group, a carboxyl group, a substituted or unsubstituted alkoxycarbonyl group, or a substituted or unsubstituted carboxamide group.

6 . The toner according to claim 1 , wherein the pigment comprises a pigment selected from the following group: carbon black; C. I. Pigment Yellow 74, 93, 139, 155, 180, and 185; and C. I. Pigment Red 31, 122, 150, 170, 258, and 269.

7 . The toner according to claim 6 , wherein the pigment comprises a pigment selected from the following group: carbon black; C. I. Pigment Yellow 155, 180, and 185; and C. I. Pigment Red 122 and 150.

8 . The toner according to claim 1 , wherein the crystalline polyester has a condensate of a dibasic acid monomer represented by the following formula (6) with a dihydric alcohol monomer represented by the following formula (7),
HOOC—(CH 2 ) m —COOH  formula (6)

wherein m in formula (6) is an integer from 4 to 12,
HO—(CH 2 ) n —OH  formula (7)

wherein n in formula (7) is an integer from 4 to 12.

9 . The toner according to claim 1 , wherein the crystalline polyester is a resin which has a polyester segment and a polystyrene segment.

10 . The toner according to claim 1 , wherein the content of the crystalline polyester is from 0.5 mass % to 20 mass % with respect to a total amount of the binder resin and the crystalline polyester.

11 . The toner according to claim 1 , wherein the content of the pigment dispersant is from 1.0 mass parts to 20 mass parts per 100 mass parts of the pigment.

12 . The toner according to claim 1 , wherein when the binder resin contains a styrene unit, the polymer moiety of the pigment dispersant contains a styrene unit, and when the binder resin contains a polyester unit, the polymer moiety of the pigment di

Assignees

• Canon Kk

Inventors

• Yoshida Yu
• Terui Yuhei
• Kubo Haruko
• Kawamura Masashi
• Murai Yasuaki
• Toyoda Takayuki

Classifications

• G03G9/091

  Azo dyes · CPC title

• G03G9/0918

  Phthalocyanine dyes · CPC title

• G03G9/092

  Quinacridones · CPC title

• G03G9/0904

  Carbon black · CPC title

• G03G9/08711

  with esters of acrylic or methacrylic acid · CPC title