# US 7,612,140 B2 · Toner, method for producing the same, image formation method and image formation apparatus

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- Number: US 7,612,140 B2
- Document ID: US7612140B2
- Status: Granted
- Kind: B2
- Application number: 11/357,015
- Filed: 2006-02-21
- Published: 2006-06-29
- Granted: 2009-11-03
- Earliest claimed: 2004-09-15
- Assignees: Canon Kabushiki Kaisha
- Inventors: Koichi Sato; Ken Eguchi
- Web page: https://patentgrep.com/patent/US7612140B2

## CPC

- G03G 9/08788: {Block polymers}
- C08F 287/00: Macromolecular compounds obtained by polymerising monomers on to block polymers
- G03G 9/08711: {with esters of acrylic or methacrylic acid}
- G03G 9/08786: {Graft polymers}
- G03G 9/08791: {characterised by the presence of specified groups or side chains}
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

There is provided a toner having favourable development characteristics and favourable stability and a method for production thereof. The toner comprises at least a graft copolymer and a coloring material, wherein the graft copolymer is formed by graft polymerization of a polymerizable monomer with a block copolymer having a polymerizable functional group on a side chain. The method for producing the toner has a step of subjecting a reaction mixture comprising at least a block copolymer having a polymerizable functional group in a side chain and having a polyalkenyl ether repeating unit structure, a polymerizable monomer, and a coloring material to suspension polymerization or emulsion polymerization, to produce a graft copolymer in which a polymer of the polymerizable monomer is grafted to the side chain of the block copolymer.

## Claims

### Claim 1

A toner, characterized in that the toner comprises at least a graft copolymer and a coloring material,
wherein the graft copolymer is formed by suspension polymerization or emulsion polymerization of a styrenic, methacrylic or acrylic monomer with an amphiphilic block copolymer having a hydrophilic block segment having a repeating unit structure represented by General Formula (1) shown below and a hydrophobic block segment having a repeating unit structure represented by general formula (2) shown below and a repeating unit structure represented by General Formula (3) shown below and has a structure in which a polymer produced by polymerization of styrenic, methacrylic or acrylic monomer is grafted to the side chain of the block copolymer;
wherein the polymerizable functional group that the block copolymer has on the side chain is in a content of 0.0001 to 50 mol % with respect to the entire block copolymer; and
wherein the styrenic, methacrylic or acrylic monomer that is graft polymerized to the block copolymer is in an amount of 0.1% by weight to 95% by weight in the toner;
General Formula (1)
wherein R0 represents —X—(COO-M)r or —X—SO3-M. X represents a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, or —(CH(R5)—CH(R6)—O)p—(CH2)m—CH3-r— or —(CH2)m—(O)n—(CH2)q—CH3-r—, or a structure in which at least one methylene group thereof is substituted by a carbonyl group, oxygen atom or aromatic ring structure; r represents 1 or 2; p represents an integer from 1 to 18; m represents an integer from 0 to 35; n represents 1 or 0; q represents an integer from 0 to 17; M represents a hydrogen atom or a monovalent or multivalent cation; and R5 and R6 represent a hydrogen atom or an alkyl group, and R5 and R6 may be the same or different from each other,
General Formula (2)
wherein R1 is selected from the group consisting of a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, -Ph, -Pyr, —(CH(R5)—CH(R6)—O)p—R7 and —(CH2)m—(O)n—R7, where a hydrogen atom in an aromatic ring may be substituted by a linear or branched alkyl group having 1 to 4 carbon atoms, and a carbon atom in an aromatic ring may be substituted by a nitrogen atom; p is an integer from 1 to 18; m is an integer from 1 to 36 and n is 0 or 1; R5 and R6 are each independently a hydrogen atom or —CH3; R7 comprises a substance selected from the group consisting of a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, -Ph, -Pyr, —CHO, —CH2CHO, —CO—CH═CH2, —CO—C(CH3)═CH2 and —CH2COOR8, provided that when R7 is other than a hydrogen atom, a hydrogen atom binding to a carbon atom in R7 can be substituted by a linear or branched alkyl group having 1 to 4 carbon atoms, —F, —Cl, or —Br, and a carbon atom in each aromatic ring can be substituted by a nitrogen atom; R8 is a hydrogen atom and an alkyl group having 1 to 5 carbon atoms; Ph represents a phenyl group and Pyr represents a pyridyl group,
General Formula (3)
wherein —OR2 is selected from the group consisting of the following formulas:
—OCH2CH2OCOCH═CH2,
—OCH2CH2OCOC (CH3)═CH2,
—OCH2CH2OCH2CH2OCOCH═CH2, or
—OCH2CH2OCH2CH2OCOC (CH3)═CH2.

### Claim 2 (depends on 1)

The toner according to any one of claims 1, characterized in that the toner is a wet toner.

### Claim 3 (depends on 1)

The toner according to claim 1, characterized in that the toner further contains a wax component.

### Claim 4 (depends on 1)

An image formation method characterized in that the method comprises a step of attaching the toner according to claim 1 on a medium for recording.

### Claim 5 (depends on 1)

An image formation apparatus characterized in that the apparatus has a means for attaching the toner according to claim 1 on a medium for recording.