# US 9,519,235 B2 · Toner, developer using the toner, image forming apparatus

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- Number: US 9,519,235 B2
- Document ID: US9519235B2
- Status: Granted
- Kind: B2
- Application number: 14/694,451
- Filed: 2015-04-23
- Published: 2015-08-13
- Granted: 2016-12-13
- Earliest claimed: 2011-10-17
- Assignees: Ricoh Company, Ltd.
- Applicants: Ricoh Company, Ltd.
- Inventors: Shingo Sakashita; Shinya Nakayama; Masahide Yamada; Atsushi Yamamoto; Hideyuki Santo; Yukiko Nakajima; Suzuka Amemori
- Web page: https://patentgrep.com/patent/US9519235B2

## CPC

- G03G 9/08764: {Polyureas; Polyurethanes}
- C08G 63/00: Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule (polyester-amides C08G69/44; polyester-imides C08G73/16)
- C08G 63/91: Polymers modified by chemical after-treatment
- C08L 67/00: Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers
- G03G 9/08755: {Polyesters}
- G03G 9/08768: {Other polymers having nitrogen in the main chain, with or without oxygen or carbon only}
- G03G 9/08793: {Crosslinked polymers}
- G03G 9/08795: {characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants}
- G03G 9/08797: {characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature}
- G03G 9/132: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds}
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A toner including at least a crystalline resin as a binder resin, wherein a tetrahydrofuran soluble content of the toner includes 5.0% or more as a peak area of a component having a molecular weight of 100,000 or greater in a molecular weight distribution measured by gel permeation chromatography, and the tetrahydrofuran soluble content of the toner has a weight-average molecular weight of 20,000 to 60,000.

## Claims

### Claim 1

A toner, comprising:
a binder resin comprising a crystalline resin, wherein the crystalline resin comprises a crystalline polyester resin and a urethane bond, a urea bond, or any combination thereof,
wherein a tetrahydrofuran soluble content of the toner comprises 5.0% or more as a peak area of a component having a molecular weight of 100,000 or greater in a molecular weight distribution measured by gel permeation chromatography, and
wherein the tetrahydrofuran soluble content of the toner has a weight-average molecular weight of 20,000 to 60,000.

### Claim 2 (depends on 1)

The toner of claim 1, wherein a ratio of (C) integrated intensity of a spectrum derived from a crystalline structure to a sum of the (C) and (A) integrated intensity of a spectrum derived from a non-crystalline structure [C/(A+C)] is 0.13 or greater in a diffraction spectrum of the toner obtained by an x-ray diffraction apparatus.

### Claim 3 (depends on 1)

The toner of claim 1, wherein the tetrahydrofuran soluble content of the toner comprises at least 0.5% or more as a peak area of a component having a molecular weight of 250,000 or greater in the molecular weight distribution measured by gel permeation chromatography.

### Claim 4 (depends on 1)

The toner of claim 1, wherein a ratio [ΔH(H)/ΔH(T)] of an endothermic quantity [ΔH(T), (J/g)] in a differential scanning calorimetry of the toner and an endothermic quantity [ΔH(H), (J/g)] in a differential scanning calorimetry of an insoluble content of the toner with respect to a mixed solvent of tetrahydrofuran and ethyl acetate [tetrahydrofuran/ethyl acetate=50/50 (mass ratio)] is in the range of 0.20 to 1.25.

### Claim 5 (depends on 1)

The toner of claim 1, wherein the crystalline resin comprises a component wherein a modified crystalline resin having an isocyanate group at an end thereof is elongated.

### Claim 6 (depends on 1)

The toner of claim 1, wherein the crystalline resin comprises a first crystalline resin and a second crystalline resin having a weight-average molecular weight greater than that of the first crystalline resin.

### Claim 7 (depends on 1)

The toner of claim 1, wherein a content of N element in a CHN analysis of the tetrahydrofuran soluble content of the toner is in the range of 0.3% by mass to 2.0% by mass.

### Claim 8 (depends on 1)

The toner of claim 1, wherein an insoluble content of the toner with respect to a mixed solution of tetrahydrofuran and ethyl acetate (tetrahydrofuran/ethyl acetate=50/50 (mass ratio)) is 10.0% by mass or greater.

### Claim 9 (depends on 1)

The toner of claim 1, wherein a common logarithmic value of a volume resistivity R of the toner by an AC bridge method is in the range of 10.0 to 10.6.

### Claim 10

A developer, comprising:
a toner comprising a binder resin comprising a crystalline resin, wherein the crystalline resin comprises a crystalline polyester resin and a urethane bond, a urea bond, or any combination thereof,
wherein a tetrahydrofuran soluble content of the toner comprises 5.0% or more as a peak area of a component having a molecular weight of 100,000 or greater in a molecular weight distribution measured by gel permeation chromatography, and
wherein the tetrahydrofuran soluble content of the toner has a weight-average molecular weight of 20,000 to 60,000.