Toner

Patent metadata

Field	Value
Publication number	US-9829814-B2
Application number	US-201615045589-A
Country	US
Kind code	B2
Filing date	Feb 17, 2016
Priority date	Feb 25, 2015
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

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 system containing at least two different polymers, said binder system comprising (i) a binder resin and (ii) a crystalline polyester other than the binder resin;
a pigment; and
a pigment dispersant, 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 −0.28≦(HP1−HP2)≦0.15
where 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,

where 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 (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, or (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 formula (2-1) or a group represented by formula (2-2); and
Ar and R 2 to R 6 satisfy at least one of (iii) Ar has a group represented by formula (2-1) or a group represented by formula (2-2) as a substituent, or (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 represented by the following formula (3)

where 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 (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, or (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 15 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 formula (2-1), or a group represented by formula (2-2); and
R 11 to R 15 and R 2 to R 6 satisfy at least one of (vii) at least one of R 11 to R 15 is a group represented by the formula (2-1) or a group represented by formula (2-2), or (viii) 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).

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

where n 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 formula (5),

where 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 group consisting of 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 group consisting of 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 formula (6) with a dihydric alcohol monomer represented by formula (7),
HOOC—(CH 2 ) m —COOH  (6)

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

wherein n is an integer from 4 to 12.

9. The toner according to claim 1 , wherein the crystalline polyester 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 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 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 dispersant contains a polyester unit.

13. The toner according to claim 1 , wherein Ar in formula (1) satisfies condition (iii).

14. The toner according to claim 1 , wherein R 2 to R 6 in formula (1) satisfy condition (ii).

15. A method of produc

Assignees

• Canon Kk

Inventors

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

Classifications

• G03G9/091

  Azo dyes · CPC title

• G03G9/0821 Primary

  characterised by physical parameters (magnetic parameters G03G9/083) · CPC title

• G03G9/0904

  Carbon black · CPC title

• G03G9/0918

  Phthalocyanine dyes · CPC title

• G03G9/0804

  whereby the components are brought together in a liquid dispersing medium · CPC title