# US 9,434,792 B2 · Modified conjugated diene rubber, method for producing same, and rubber composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,434,792 B2 - Document ID: US9434792B2 - Status: Granted - Kind: B2 - Application number: 14/114,123 - Filed: 2012-04-17 - Published: 2014-02-20 - Granted: 2016-09-06 - Earliest claimed: 2011-04-26 - Assignees: Jsr Corporation - Applicants: Hiroyuki Morita; Masahiro Shibata; Ryoji Tanaka - Inventors: Hiroyuki Morita; Masahiro Shibata; Ryoji Tanaka - Web page: https://patentgrep.com/patent/US9434792B2 ## CPC - C08C 19/25: Incorporating silicon atoms into the molecule - B60C 1/00: Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition - B60C 1/0016: {Compositions of the tread} - C08C 19/44: of polymers containing metal atoms exclusively at one or both ends of the skeleton - C08K 3/04: Carbon - C08K 3/36: Silica - C08L 9/00: Compositions of homopolymers or copolymers of conjugated diene hydrocarbons - C08L 15/00: Compositions of rubber derivatives (C08L11/00, C08L13/00 take precedence) - C08L 91/00: Compositions of oils, fats or waxes; Compositions of derivatives thereof - C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS - B60C: VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A method containing a step of reacting a conjugated diene polymer having an alkali metal or alkaline earth metal active end with a hydrocarbyloxysilane compound having one or more of each of the following functional groups I and II in its molecule to obtain a modified conjugated diene polymer containing a functional group II, and a step of mixing the modified conjugated diene polymer and a compound such as organic acid. A modified conjugated diene rubber which can be used as a raw material of a cross-linked rubber which can be used in tire treads and the like and can enhance low fuel consumption performance is provided. The functional group I is a hydrocarbyloxysilyl group. The functional group II is a nitrogen-containing group in which both of two hydrogen atoms of a primary amino group are substituted with protective groups. ## Claims ### Claim 1 A method comprising: reacting a conjugated diene polymer with a hydrocarbyloxysilane compound having one or more functional groups (I) and one or more a functional groups (II) in a molecule thereof to obtain a modified conjugated diene polymer containing the functional group (II), wherein the conjugate diene polymer comprises a structural unit derived from a conjugated diene compound and optionally a structural unit derived from an aromatic vinyl compound, and further comprises an alkali metal or alkaline-earth metal active end, the functional group (I) is a hydrocarbyloxysilyl group, and the functional group (II) is a nitrogen-containing group in which both of two hydrogen atoms of a primary amino group are substituted with a protective group; and mixing the modified conjugated diene polymer and at least one compound selected from the group consisting of an organic acid, an organic acid halide, and a carboxylic anhydride to obtain a modified conjugated diene rubber. ### Claim 2 (depends on 1) The method according to claim 1, wherein the at least one compound is selected from the group consisting of a carboxylic acid, a carboxylic anhydride, a carboxylic halide, an organic phosphoric acid, an organic phosphoric acid halide, an organic phosphorous acid, an organic phosphorous acid halide, an organic sulfonic acid, an organic sulfonic acid halide, an organic sulfinic acid, an organic sulfonic acid halide, and an organic thio acid. ### Claim 3 (depends on 1) The method according to claim 1, further comprising: bringing the modified conjugated diene rubber into contact with water. ### Claim 4 (depends on 1) The method according to claim 1, wherein the modified conjugated diene rubber has an onium structure formed by the modified conjugated diene polymer. ### Claim 5 (depends on 1) A modified conjugated diene rubber obtained by the method according to claim 1. ### Claim 6 (depends on 5) A rubber composition, comprising: the modified conjugated diene rubber according to claim 5, silica and/or carbon black, and a cross-linking agent. ### Claim 7 (depends on 6) A cross-linked rubber obtained by a process comprising cross-linking the rubber composition according to claim 6. ### Claim 8 (depends on 7) A tire, comprising the cross-linked rubber according to claim 7. ### Claim 9 (depends on 1) The method according to claim 1, further comprising: performing an anionic polymerization of the conjugated diene compound and optionally the aromatic vinyl compound in a presence of an alkali metal- or alkaline-earth metal-based polymerization initiator to obtain the conjugate diene polymer. ### Claim 10 (depends on 1) The method according to claim 1, wherein the alkali metal or alkaline-earth metal active end comprises lithium. ### Claim 11 (depends on 1) The method according to claim 1, wherein the conjugated diene compound is 1,3-butadiene. ### Claim 12 (depends on 1) The method according to claim 1, wherein the aromatic vinyl compound is styrene. ### Claim 13 (depends on 1) The method according to claim 1, wherein an amount of the at least one compound mixed with the modified conjugated diene polymer is 1.0 molar equivalent or more based on alkali components present in a reaction system. ### Claim 14 (depends on 1) The method according to claim 1, wherein an amount of the at least one compound mixed with the modified conjugated diene polymer is 1.5 molar equivalent or more based on alkali components present in a reaction system. ### Claim 15 (depends on 1) The method according to claim 1, wherein a temperature of mixing the modified conjugated diene polymer and the at least one compound is from 0 to 120° C. ### Claim 16 (depends on 1) The method according to claim 1, wherein a temperature of mixing the modified conjugated diene polymer and the at least one compound is from 20 to 100° C.