# US 10,310,396 B2 · Method of producing toner > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,310,396 B2 - Document ID: US10310396B2 - Status: Granted - Kind: B2 - Application number: 15/974,936 - Filed: 2018-05-09 - Published: 2018-11-15 - Granted: 2019-06-04 - Earliest claimed: 2017-05-15 - Assignees: Canon Kabushiki Kaisha - Applicants: Canon Kabushiki Kaisha - Inventors: Kenta Kamikura; Kunihiko Nakamura; Maho Tanaka; Fumiya Hatakeyama - Web page: https://patentgrep.com/patent/US10310396B2 ## CPC - G03G 9/0806: {whereby chemical synthesis of at least one of the toner components takes place} - G03G 9/0804: {whereby the components are brought together in a liquid dispersing medium} - G03G 9/0812: {Pretreatment of components} - G03G 9/0825: {characterised by their structure; characterised by non-homogenuous distribution of components (microcapsular toners G03G9/093)} - G03G 9/0827: {characterised by their shape, e.g. degree of sphericity} - G03G 9/087: Binders for toner particles - G03G 9/08773: {Polymers having silicon in the main chain, with or without sulfur, oxygen, nitrogen or carbon only} - G03G 9/09775: {containing atoms other than carbon, hydrogen or oxygen (G03G9/09741 - G03G9/09766 take precedence)} - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract A first aspect is a toner production method in which an organosilicon compound is condensed in a surfactant-containing aqueous medium with a specific surface tension, in which a resin particle is dispersed, to produce a toner having the condensate of the organosilicon compound on the surface of the resin particle, and a second aspect is a toner production method in which an organosilicon compound is condensed in an aqueous medium which has a surfactant and a specific metal salt and in which a resin particle is dispersed, to produce a toner having the condensate of the organosilicon compound on the surface of the resin particle. ## Claims ### Claim 1 A method of producing a toner comprising a toner particle, the toner particle containing: a resin particle containing a binder resin, and a condensate of an organosilicon compound on a surface of the resin particle, the toner production method comprising: a condensation step of condensing an organosilicon compound given by formula (1) below in a surfactant-containing aqueous medium, in which the resin particle is dispersed, to obtain the toner particle, wherein a surface tension of the aqueous medium in the condensation step is at least 35.0 mN/m: Ra(n)—Si—Rb(4-n) (1) wherein, in formula (1), each Ra independently represents a halogen atom, a hydroxy group, or an alkoxy group; each Rb independently represents an alkyl group, an alkenyl group, an aryl group, an acyl group, or a methacryloxyalkyl group; and n represents an integer from 1 to 4. ### Claim 2 (depends on 1) The toner production method according to claim 1, wherein the surface tension of the aqueous medium in the condensation step is not more than 60.0 mN/m. ### Claim 3 (depends on 1) The toner production method according to claim 1, wherein n in formula (1) is an integer from 2 to 4. ### Claim 4 (depends on 1) The toner production method according to claim 1, wherein pH of the aqueous medium in the condensation step is from 7.5 to 12.0. ### Claim 5 (depends on 1) The toner production method according to claim 1, comprising a step of obtaining the resin particle by aggregating, in the aqueous medium, resin fine particles that contain the binder resin. ### Claim 6 (depends on 1) The toner production method according to claim 1, wherein concentration of the surfactant in the aqueous medium in the condensation step is from 1.0×10−4 mass % to 1.0×101 mass %. ### Claim 7 (depends on 1) The toner production method according to claim 1, wherein, in formula (1), each Ra independently represents a halogen atom, a hydroxy group, or an alkoxy group having 1 to 6 carbons, and each Rb independently represents an alkyl group having 1 to 8 carbons, an alkenyl group having 1 to 8 carbons, an aryl group having 6 to 12 carbons, an acyl group having 1 to 8 carbons, or a methacryloxyalkyl group having an alkyl chain having 1 to 8 carbons. ### Claim 8 A method of producing a toner comprising a toner particle, the toner particle containing: a resin particle containing a binder resin, and a condensate of an organosilicon compound on a surface of the resin particle, the toner production method comprising: a condensation step of condensing an organosilicon compound given by formula (1) below in a surfactant-containing aqueous medium, in which the resin particle is dispersed, to obtain the toner particle, wherein the aqueous medium in the condensation step contains a metal salt containing an at least divalent metal ion, and the metal salt satisfies formula (2) below: Ra(n)—Si—Rb(4-n) (1) wherein, in formula (1), each Ra independently represents a halogen atom, a hydroxy group, or an alkoxy group; each Rb independently represents an alkyl group, an alkenyl group, an aryl group, an acyl group, or a methacryloxyalkyl group; and n represents an integer from 1 to 4; and 70.0≤A×B (2) wherein, in formula (2), A represents the valence of the metal ion present in the metal salt and B represents the content (mmol/L) of the metal ion in the aqueous medium. ### Claim 9 (depends on 8) The toner production method according to claim 8, wherein the surface tension of the aqueous medium in the condensation step is not more than 60.0 mN/m. ### Claim 10 (depends on 8) The toner production method according to claim 8, wherein n in formula (1) is an integer from 2 to 4. ### Claim 11 (depends on 8) The toner production method according to claim 8, wherein pH of the aqueous medium in the condensation step is from 7.5 to 12.0. ### Claim 12 (depends on 8) The toner production method according to claim 8, comprising a step of obtaining the resin particle by aggregating, in the aqueous medium, resin fine particles that contain the binder resin. ### Claim 13 (depends on 8) The toner production method according to claim 8, wherein concentration of the surfactant in the aqueous medium in the condensation step is from 1.0×10−4 mass % to 1.0×101 mass %. ### Claim 14 (depends on 8) The toner production method according to claim 8, wherein, in formula (1), each Ra independently represents a halogen atom, a hydroxy group, or an alkoxy group having 1 to 6 carbons, and each Rb independently represents an alkyl group having 1 to 8 carbons, an alkenyl group having 1 to 8 carbons, an aryl group having 6 to 12 carbons, an acyl group having 1 to 8 carbons, or a methacryloxyalkyl group having an alkyl chain having 1 to 8 carbons.