IP Library › Granted Patent US 12,228,882
Granted Patent B2
US 12,228,882 · App. 17/660,146 · Granted Feb 18, 2025

Toner

Inventors: Atsuhiko Ohmori (Kanagawa, JP); Hiroki Kagawa (Shizuoka, JP); Keisuke Adachi (Tokyo, JP); Tomoko Sugita (Shizuoka, JP)
Assignee: CANON KABUSHIKI KAISHA
G03G9/0825G03G9/08755G03G9/09328
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Quick Facts
Patent No.
US 12,228,882
App. No.
17/660,146
Granted
Feb 18, 2025
Kind
B2
Abstract

A toner comprising: a toner particle comprising a binder resin and a hydrocarbon wax; and inorganic fine particles, wherein the inorganic fine particles include silica fine particles surface-treated with specific polydimethylsiloxanes, a total amount of trimethylsilanol in the silica fine particles is from 1.0 ppm to 5.0 ppm, where a standard value of an amount of ions of an ester group is measured by time-of-flight secondary ion mass spectrometry, one or more peaks of the standard value are present within a range of 100 nm from the surface of the toner particle, and the maximum value A(d max) among the peaks of the standard value and the standard value A(0) on the surface of the toner particle satisfy the following relationships: 1.05≤ A ( d max)/ A (0)≤5.00, A (0)≥0.010.

Claims (50)

1. A toner comprising:

a toner particle comprising a binder resin and a hydrocarbon wax; and

an inorganic fine particle, wherein

the toner comprises, as the inorganic fine particle, a silica fine particle surface-treated with

a polydimethylsiloxane represented by a following formula (A) and

a polydimethylsiloxane represented by a following formula (B);

a total amount of trimethylsilanol in terms of octamethyltrisiloxane based on the mass of the silica fine particle in organic volatile component analysis of the silica fine particle at a heating temperature of 150° C. by a headspace method is 1.0 to 5.0 ppm;

where, in a measurement of the toner particle by time-of-flight secondary ion mass spectrometry measured from the surface of the toner particle to a depth of 100 nm, a value obtained by dividing an amount of ions of a structure represented by a following formula (C) by a total amount of counted ions is taken as a standard value,

at least one peak of the standard value is present within a range of 100 nm from the surface of the toner particle;

where the maximum value among the at least one peak of the standard value is denoted by A(d max), and the standard value on the toner particle surface is denoted by A(0),

the A(d max) and the A(0) satisfy following formulas (1) and (2):

where, in the formula (B), R 1 is a carbinol group, a hydroxy group, an epoxy group, a carboxy group, an alkyl group, or a hydrogen atom, and R 2 is a carbinol group, a hydroxy group, an epoxy group, a carboxy group, or a hydrogen atom; n and m are average numbers of repeating units, n is 30 to 200, and m is 30 to 200; and each methyl group (—CH 3 ) of side chains in the formula (B) may be substituted with a carbinol group, a hydroxy group, an epoxy group, a carboxy group, or a hydrogen atom.

2. The toner according to claim 1 , wherein the polydimethylsiloxane represented by the formula (B) is a polydimethylsiloxane represented by a following formula (D).

In the formula (D), p is the average number of repeating units, which is from 30 to 200.

3. The toner according to claim 1 , wherein the silica fine particle has a number average particle diameter of primary particle of 5 to 30 nm.

4. The toner according to claim 1 , wherein

where the standard value at a position at a depth of 100 nm from the surface of the toner particle among the standard values in the analysis by the time-of-flight type secondary ion mass spectrometry is denoted by A(100),

the A(dmax) and the A(100) satisfy a following formula (3):

1.05≤A(dmax)/A(100)≤5.00  (3).

5. The toner according to claim 1 , wherein

the binder resin comprises a polyester resin;

the polyester resin comprises a monomer unit represented by a following formula (E), a monomer unit represented by a following formula (F), and a monomer unit represented by a following formula (G);

a content ratio of the monomer unit represented by the following formula (E) in the polyester resin is 30 to 50% by mass;

a content ratio of the monomer unit represented by the following formula (F) in the polyester resin is 25 to 50% by mass; and

a content ratio of the monomer unit represented by the following formula (G) in the polyester resin is 0.4 to 50% by mass:

where, in the formula (E), R 3 represents a benzene ring, in the formula (F), R 4 each represent an ethylene group or a propylene group, x and y are each an integer of 1 or more, and an average value of x+y is 2 to 10, in the formula (G), R 5 represents an ethylene group or a propylene group.

6. The toner according to claim 5 , wherein

the toner particle comprises a core particle, and a shell on a surface of the core particle;

the core particle comprises a styrene-acrylic resin; and

the shell comprises the polyester resin.

7. The toner according to claim 6 , wherein, in cross-sectional observation of the toner with a transmission electron microscope, an average value of a thickness of the shell is 100 to 200 nm.

8. The toner according to claim 1 , wherein

the binder resin comprises a polyester resin, and

the polyester resin comprises a monomer unit represented by a following formula (H).

9. The toner according to claim 6 , wherein a content ratio of the monomer unit represented by the formula (H) in the polyester resin is 1.0 to 4.0% by mass.

10. A toner comprising:

a toner particle comprising a styrene-acrylic resin, a polyester resin and a hydrocarbon wax; and

an inorganic fine particle, wherein

the inorganic fine particle comprises a silica fine particle surface-treated with a polydimethylsiloxane represented by a following formula (A) and a polydimethylsiloxane represented by a following formula (B);

the toner particle comprises a core particle, and a shell on a surface of the core particle;

the core particle comprises the styrene-acrylic resin;

the shell comprises the polyester resin;

an average value of a thickness of the shell in cross-sectional observation of the toner with a transmission electron microscope is 100 to 200 nm;

where, in a measurement of the toner particle by time-of-flight secondary ion mass spectrometry measured from the surface of the toner particle to a depth of 100 nm, a value obtained by dividing an amount of ions of a structure represented by a following formula (C) by a total amount of counted ions is taken as a standard value,

at least one peak of the standard value is present within a range of 100 nm from the surface of the toner particle;

where the maximum value among the at least one peak of the standard value is denoted by A(d max), and the standard value on the toner particle surface is denoted by A(0),

the A(d max) and the A(0) satisfy following formulas (1) and (2):

where, in the formula (B), R 1 is a carbinol group, a hydroxy group, an epoxy group, a carboxy group, an alkyl group, or a hydrogen atom, and R 2 is a carbinol group, a hydroxy group, an epoxy group, a carboxy group, or a hydrogen atom; n and m are average numbers of repeating units, n is 30 to 200, and m is 30 to 200; and each methyl group (—CH 3 ) of side chains in the formula (B) may be substituted with a carbinol group, a hydroxy group, an epoxy group, a carboxy group, or a hydrogen atom.

11. The toner according to claim 10 , wherein a surface treatment amount of the polydimethylsiloxane represented by the formula (A) is 3 to 40 parts by mass with respect to 100 parts by mass of the silica fine particle before a surface treatment, and

a mass ratio (B)/(A) of the polydimethylsiloxane represented by the formula (B) to the polydimethylsiloxane represented by the formula (A) in the surface treatment is 0.05 to 10.00.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2022
From: OHMORI, ATSUHIKO; KAGAWA, HIROKI; ADACHI, KEISUKE; SUGITA, TOMOKO
To: CANON KABUSHIKI KAISHA
Reel/Frame 061668/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2022
From: OHMORI, ATSUHIKO; KAGAWA, HIROKI; ADACHI, KEISUKE; SUGUTA, TOMOKO
To: CANON KABUSHIKI KAISHA
Reel/Frame 061573/0059 →
Priority Claims (1)
JP 2021-076193 · Apr 28, 2021 · national
Continuity (1)
Related Publication 20220373906A1 · Nov 24, 2022
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