KR20170102320A - 변성 공액 디엔계 중합체 및 그의 제조 방법, 및 변성 공액 디엔계 중합체 조성물 - Google Patents
변성 공액 디엔계 중합체 및 그의 제조 방법, 및 변성 공액 디엔계 중합체 조성물 Download PDFInfo
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- KR20170102320A KR20170102320A KR1020177021439A KR20177021439A KR20170102320A KR 20170102320 A KR20170102320 A KR 20170102320A KR 1020177021439 A KR1020177021439 A KR 1020177021439A KR 20177021439 A KR20177021439 A KR 20177021439A KR 20170102320 A KR20170102320 A KR 20170102320A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- conjugated diene
- group
- diene polymer
- modified conjugated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 140
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- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
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- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- NBMUDWHKTYVBTA-UHFFFAOYSA-N dimethoxymethyl-[3-(2-methylazasilolidin-1-yl)propyl]silane Chemical compound C[SiH]1N(CCC1)CCC[SiH2]C(OC)OC NBMUDWHKTYVBTA-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- 230000005660 hydrophilic surface Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical group [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- XOXRRQOIDCIGAX-UHFFFAOYSA-N lithium ethyl(propyl)azanide Chemical compound [Li+].CCC[N-]CC XOXRRQOIDCIGAX-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- FUFBXNLRARNIOH-UHFFFAOYSA-N lithium;3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound [Li].C1C2NCC1(C)CC(C)(C)C2 FUFBXNLRARNIOH-UHFFFAOYSA-N 0.000 description 1
- LHPXHKQJYVVXKC-UHFFFAOYSA-N lithium;benzyl(ethyl)azanide Chemical compound [Li+].CC[N-]CC1=CC=CC=C1 LHPXHKQJYVVXKC-UHFFFAOYSA-N 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
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- AWQIHVZFQSNHCZ-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-phenylmethanediamine Chemical compound CN(C)C(N(C)C)C1=CC=CC=C1 AWQIHVZFQSNHCZ-UHFFFAOYSA-N 0.000 description 1
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
- WOQIWIYDKMIQQY-UHFFFAOYSA-N n,n-dibutyl-2-methylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1C WOQIWIYDKMIQQY-UHFFFAOYSA-N 0.000 description 1
- MUKJUKMSNRJVBD-UHFFFAOYSA-N n,n-dibutyl-3-methylaniline Chemical compound CCCCN(CCCC)C1=CC=CC(C)=C1 MUKJUKMSNRJVBD-UHFFFAOYSA-N 0.000 description 1
- YQYUUNRAPYPAPC-UHFFFAOYSA-N n,n-diethyl-2-methylaniline Chemical compound CCN(CC)C1=CC=CC=C1C YQYUUNRAPYPAPC-UHFFFAOYSA-N 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- XOZZATXWQMOVHL-UHFFFAOYSA-N n,n-dimethyl-1,1-di(propan-2-yloxy)methanamine Chemical compound CC(C)OC(N(C)C)OC(C)C XOZZATXWQMOVHL-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
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- 239000004945 silicone rubber Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5445—Silicon-containing compounds containing nitrogen containing at least one Si-N bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/06—Copolymers with styrene
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120130253A (ko) * | 2010-04-16 | 2012-11-29 | 아사히 가세이 케미칼즈 가부시키가이샤 | 변성 공액 디엔계 중합체의 제조 방법, 변성 공액 디엔계 중합체 및 변성 공액 디엔계 중합체 조성물 |
| JP2013087219A (ja) * | 2011-10-19 | 2013-05-13 | Asahi Kasei Chemicals Corp | サイドウォール用ゴム組成物 |
| JP2013129693A (ja) * | 2011-12-20 | 2013-07-04 | Asahi Kasei Chemicals Corp | 変性共役ジエン重合体の製造方法及び変性共役ジエン重合体の組成物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3441201B2 (ja) | 1993-12-29 | 2003-08-25 | 株式会社ブリヂストン | 重合体及びその重合体組成物 |
| WO2001023467A1 (en) | 1999-09-27 | 2001-04-05 | Asahi Kasei Kabushiki Kaisha | Rubber composition |
| JP4598909B2 (ja) | 1999-12-02 | 2010-12-15 | 株式会社ブリヂストン | ゴム組成物及びそれを用いた空気入りタイヤ |
| JP4129619B2 (ja) | 2001-09-27 | 2008-08-06 | Ｊｓｒ株式会社 | 共役ジオレフィン（共）重合ゴム、該（共）重合ゴムの製造方法、ゴム組成物およびタイヤ |
| KR100992324B1 (ko) * | 2005-09-22 | 2010-11-05 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 공액 디엔계 중합체 및 그의 제조 방법 |
| JP5568860B2 (ja) | 2006-03-31 | 2014-08-13 | 日本ゼオン株式会社 | タイヤ用ゴム組成物の製造方法、タイヤ用ゴム組成物、及びタイヤ |
| JP5127521B2 (ja) | 2008-03-24 | 2013-01-23 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体及びその製造方法、並びに重合体組成物 |
| ES2568892T3 (es) | 2008-10-14 | 2016-05-05 | Asahi Kasei Chemicals Corporation | Polímero a base de dieno conjugado modificado, procedimiento para producirlo, composición de polímero a base de dieno conjugado modificado y neumático para vehículos |
| CN103764682B (zh) * | 2011-08-26 | 2016-01-20 | 旭化成化学株式会社 | 改性共轭二烯系聚合物的制造方法、改性共轭二烯系聚合物、改性共轭二烯系聚合物组合物、橡胶组合物和轮胎 |
| JP5687768B2 (ja) | 2011-09-08 | 2015-03-18 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、変性共役ジエン系重合体組成物、ゴム組成物及びタイヤ |
| JP5971915B2 (ja) * | 2011-10-11 | 2016-08-17 | 旭化成株式会社 | 変性共役ジエン系重合体組成物及びその製造方法 |
| JP5964571B2 (ja) | 2011-10-12 | 2016-08-03 | 旭化成株式会社 | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、及び変性共役ジエン系重合体組成物、及びタイヤ |
| JP6106476B2 (ja) * | 2013-03-13 | 2017-03-29 | 旭化成株式会社 | 変性共役ジエン系重合体組成物、トレッド、サイドウォール及びタイヤ |
| JP2015113437A (ja) * | 2013-12-13 | 2015-06-22 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体組成物の製造方法 |
-
2016
- 2016-02-19 BR BR112017016522-8A patent/BR112017016522A2/pt not_active Application Discontinuation
- 2016-02-19 CN CN201680010344.8A patent/CN107250172B/zh active Active
- 2016-02-19 WO PCT/JP2016/054869 patent/WO2016133202A1/ja not_active Ceased
- 2016-02-19 EP EP16752588.0A patent/EP3260476B1/en active Active
- 2016-02-19 US US15/551,548 patent/US10766972B2/en active Active
- 2016-02-19 HU HUE16752588 patent/HUE044416T2/hu unknown
- 2016-02-19 JP JP2017500757A patent/JP6607916B2/ja active Active
- 2016-02-19 TW TW105105015A patent/TWI607026B/zh not_active IP Right Cessation
- 2016-02-19 KR KR1020177021439A patent/KR20170102320A/ko not_active Ceased
- 2016-02-19 KR KR1020197015111A patent/KR102160548B1/ko not_active Ceased
- 2016-02-19 SG SG11201706426YA patent/SG11201706426YA/en unknown
-
2019
- 2019-09-03 JP JP2019160438A patent/JP6908662B2/ja active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120130253A (ko) * | 2010-04-16 | 2012-11-29 | 아사히 가세이 케미칼즈 가부시키가이샤 | 변성 공액 디엔계 중합체의 제조 방법, 변성 공액 디엔계 중합체 및 변성 공액 디엔계 중합체 조성물 |
| JP2013087219A (ja) * | 2011-10-19 | 2013-05-13 | Asahi Kasei Chemicals Corp | サイドウォール用ゴム組成物 |
| JP2013129693A (ja) * | 2011-12-20 | 2013-07-04 | Asahi Kasei Chemicals Corp | 変性共役ジエン重合体の製造方法及び変性共役ジエン重合体の組成物 |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190031702A (ko) * | 2017-09-18 | 2019-03-27 | 주식회사 엘지화학 | 연속식 중합에 의한 공액디엔계 중합체의 제조방법 |
| US11130832B2 (en) | 2017-12-05 | 2021-09-28 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and rubber composition including the same |
| WO2019112261A1 (ko) * | 2017-12-05 | 2019-06-13 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2019112262A1 (ko) * | 2017-12-05 | 2019-06-13 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2019112263A1 (ko) * | 2017-12-05 | 2019-06-13 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2019112260A1 (ko) * | 2017-12-05 | 2019-06-13 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR20190066573A (ko) * | 2017-12-05 | 2019-06-13 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| US11414510B2 (en) | 2017-12-05 | 2022-08-16 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and rubber composition including the same |
| US11299559B2 (en) | 2017-12-05 | 2022-04-12 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and rubber composition including the same |
| US11198777B2 (en) | 2017-12-05 | 2021-12-14 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and rubber composition including the same |
| KR20190134450A (ko) * | 2018-05-25 | 2019-12-04 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR20200074073A (ko) * | 2018-05-25 | 2020-06-24 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2019225824A1 (ko) * | 2018-05-25 | 2019-11-28 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| US12122856B2 (en) | 2018-05-25 | 2024-10-22 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and rubber composition including the same |
| KR20200001996A (ko) * | 2018-06-28 | 2020-01-07 | 아사히 가세이 가부시키가이샤 | 변성 공액 디엔계 중합체 혼합물의 제조 방법 |
| US10995163B2 (en) | 2018-07-11 | 2021-05-04 | Lg Chem, Ltd. | Modified conjugated diene-based polymer and rubber composition including the same |
| KR102035177B1 (ko) * | 2018-07-11 | 2019-11-08 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR20210037161A (ko) * | 2019-09-27 | 2021-04-06 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR20210052197A (ko) * | 2019-10-30 | 2021-05-10 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20190060893A (ko) | 2019-06-03 |
| CN107250172A (zh) | 2017-10-13 |
| US20180037674A1 (en) | 2018-02-08 |
| JP6908662B2 (ja) | 2021-07-28 |
| JPWO2016133202A1 (ja) | 2017-11-02 |
| HUE044416T2 (hu) | 2019-10-28 |
| JP6607916B2 (ja) | 2019-11-20 |
| TW201708272A (zh) | 2017-03-01 |
| WO2016133202A1 (ja) | 2016-08-25 |
| EP3260476A1 (en) | 2017-12-27 |
| KR102160548B9 (ko) | 2022-02-18 |
| EP3260476A4 (en) | 2018-01-03 |
| EP3260476B1 (en) | 2019-05-08 |
| TWI607026B (zh) | 2017-12-01 |
| BR112017016522A2 (pt) | 2018-04-10 |
| SG11201706426YA (en) | 2017-09-28 |
| JP2019206723A (ja) | 2019-12-05 |
| CN107250172B (zh) | 2021-04-09 |
| US10766972B2 (en) | 2020-09-08 |
| KR102160548B1 (ko) | 2020-09-28 |
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