# US 12,346,064 B2 · Toner

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- Number: US 12,346,064 B2
- Document ID: US12346064B2
- Status: Granted
- Kind: B2
- Application number: 17/502,876
- Filed: 2021-10-15
- Published: 2022-04-28
- Granted: 2025-07-01
- Earliest claimed: 2020-10-23
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Masashi Kawamura; Akane Masumoto; Takayuki Toyoda; Kenji Ookubo; Taku Shimoda; Yu Yoshida
- Web page: https://patentgrep.com/patent/US12346064B2

## CPC

- C09D 151/003: {grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds (C09D151/04, C09D151/06 take precedence)}
- G03G 9/09775: {containing atoms other than carbon, hydrogen or oxygen (G03G9/09741 - G03G9/09766 take precedence)}
- C08F 8/32: by reaction with amines
- C08F 220/14: Methyl esters {, e.g. methyl (meth)acrylate}
- C08F 257/02: on to polymers of styrene or alkyl-substituted styrenes
- C08F 265/04: on to polymers of esters
- C08F 265/06: Polymerisation of acrylate or methacrylate esters on to polymers thereof
- C08F 283/02: on to polycarbonates or saturated polyesters {(C08F283/004 takes precedence)}
- C08G 63/08: Lactones or lactides
- C08G 63/183: Terephthalic acids
- C08G 63/20: Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
- C08G 63/672: Dicarboxylic acids and dihydroxy compounds
- C09D 151/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G 9/08711: {with esters of acrylic or methacrylic acid}
- G03G 9/08755: {Polyesters}
- G03G 9/08773: {Polymers having silicon in the main chain, with or without sulfur, oxygen, nitrogen or carbon only}
- G03G 9/08788: {Block polymers}
- G03G 9/08791: {characterised by the presence of specified groups or side chains}
- C08F 212/08: Styrene
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A toner comprising a toner particle, wherein the toner particle comprises a binder resin, a resin A, and a resin B, the resin A comprises a substituted or unsubstituted silyl group in a molecule, a substituent of the substituted silyl group is at least one selected from the group consisting of 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 the resin B comprises an azo group in a molecule.

## Claims

### Claim 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 P1 represents a polyester resin segment, L1 represents a single bond or a divalent linking group, R1 to R3 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 L1, a plurality of R1, a plurality of R2, and a plurality of R3 may be the same or different from each other.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

The toner according to claim 1, wherein at least one of R1 to R3 represents an alkoxy group having one or more carbon atoms, or a hydroxy group.

### Claim 4 (depends on 1)

The toner according to claim 1, wherein each of R1 to R3 independently represents an alkoxy group having one or more carbon atoms, or a hydroxy group.

### Claim 5 (depends on 1)

The toner according to claim 1, wherein L1 is represented by formula (2)
where R5 represents a single bond, an alkylene group or an arylene group, (*) represents a binding site to P1, and (**) represents a binding site to the silicon atom in formula (1).

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

The toner according to claim 1, wherein resin B includes a structure represented by formula (11A) below:
Ar11—N═N—Ar21 (11A)
where Ar11 and Ar21 independently represent a substituted or unsubstituted aromatic group, with the proviso that at least one of Ar11 and Ar21 has a substituent forming a binding segment with an organic resin in resin B.

### Claim 8 (depends on 1)

The toner according to claim 1, wherein the resin B includes a structure represented by formula (12A) below:
where R51 and R61 independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, an OR7 group or an NR8R9 group, R7 to R9 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group or an aralkyl group, and Ar31 represents a substituted or unsubstituted aryl group, with the proviso that at least one of R51, R61, and Ar31 has a divalent substituent forming a binding segment with an organic resin in resin B.

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 1)

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.

### Claim 11 (depends on 1)

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.