Granted Patent B2

US 12,314,005 · App. 17/502,876 · Granted May 27, 2025

Inventors: Masashi Kawamura (Kanagawa, JP); Akane Masumoto (Shizuoka, JP); Takayuki Toyoda (Shizuoka, JP); Kenji Ookubo (Shizuoka, JP); Taku Shimoda (Tokyo, JP); Yu Yoshida (Shizuoka, JP)

Assignee: CANON KABUSHIKI KAISHA

G03G9/09775C08F8/32C08F265/04G03G9/08711

Abstract

Claims (23)

1. A toner, comprising:

a toner particle, the toner particle comprising a binder resin, a resin A, and a resin B;

the resin A comprising a structure represented by formula (1)

where P 1 represents a polyester resin segment, L 1 represents a single bond or a divalent linking group, R 1 to R 3 independently represent a hydrogen atom, an alkyl group having 1 or more carbon atoms, an alkoxy group having 1 or more carbon atoms, a hydroxy group, a halogen atom, and an aryl group having 6 or more carbon atoms, and m represents a positive integer; and

the resin B comprises an azo group in a molecule, wherein

when m is 2 or more, a plurality of L 1, a plurality of R 1, a plurality of R 2 , and a plurality of R 3 may be the same or different from each other.

2. The toner according to claim 1 , wherein an amount of silicon atoms in the resin A is 0.02 to 10.00% by mass.

3. The toner according to claim 1 , wherein at least one of R 1 to R 3 represents an alkoxy group having one or more carbon atoms, or a hydroxy group.

4. The toner according to claim 1 , wherein each of R 1 to R 3 independently represents an alkoxy group having one or more carbon atoms, or a hydroxy group.

5. The toner according to claim 1 , wherein L 1 is represented by formula (2)

where R 5 represents a single bond, an alkylene group or an arylene group, (*) represents a binding site to P 1 , and (**) represents a binding site to the silicon atom in formula (1).

6. The toner according to claim 1 , wherein resin A has a weight average molecular weight of 3000 to 100000.

7. The toner according to claim 1 , wherein resin B includes a structure represented by formula (11A) below:

Ar 11 —N═N—Ar 21 (11A)

where Ar 11 and Ar 21 independently represent a substituted or unsubstituted aromatic group, with the proviso that at least one of Ar 11 and Ar 21 has a substituent forming a binding segment with an organic resin in resin B.

8. The toner according to claim 1 , wherein the resin B includes a structure represented by formula (12A) below:

where R 51 and R 61 independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an OR 7 group or an NR 8 R 9 group, R 7 to R 9 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group or an aralkyl group, and Ar 31 represents a substituted or unsubstituted aryl group, with the proviso that at least one of R 51, R 61, and Ar 31 has a divalent substituent forming a binding segment with an organic resin in resin B.

9. The toner according to claim 1 , wherein resin B has a weight average molecular weight of 3000 to 100000.

10. The toner according to claim 1 , wherein

Tg(A)>Tg(C)

Tg(B)>Tg(C)

where Tg(A) is stands for a glass transition temperature Tg of resin A, Tg(B) is for a glass transition temperature Tg of resin B, and Tg(C) is a glass transition temperature Tg of binder resin.

11. The toner according to claim 1 , wherein the binder resin is a copolymer of styrene and a (meth) acrylic acid alkyl ester with an alkyl group having 1 to 8 carbon atoms, and having a styrene: (meth)acrylic acid alkyl ester copolymerization ratio (mass ratio) of 55:45 to 80:20.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (217)