JP5956556B2 - シリル化アミノ基を含有するカルボン酸またはチオカルボン酸エステルで官能化されたポリマー - Google Patents
シリル化アミノ基を含有するカルボン酸またはチオカルボン酸エステルで官能化されたポリマー Download PDFInfo
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- JP5956556B2 JP5956556B2 JP2014502785A JP2014502785A JP5956556B2 JP 5956556 B2 JP5956556 B2 JP 5956556B2 JP 2014502785 A JP2014502785 A JP 2014502785A JP 2014502785 A JP2014502785 A JP 2014502785A JP 5956556 B2 JP5956556 B2 JP 5956556B2
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- amino
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- trimethylsilyl
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- 125000003277 amino group Chemical group 0.000 title claims description 134
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 95
- 125000000962 organic group Chemical group 0.000 claims description 77
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 70
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- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 125000000129 anionic group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 150000001993 dienes Chemical class 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
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- 125000004429 atom Chemical group 0.000 claims description 8
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- 229910052760 oxygen Inorganic materials 0.000 claims description 8
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 32
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- 239000006233 lamp black Substances 0.000 description 1
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- ZLPHTMMGQHNDDQ-UHFFFAOYSA-N lithium;2-methylbutane Chemical compound [Li+].CC(C)C[CH2-] ZLPHTMMGQHNDDQ-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- CKVWBMJEETWJTF-UHFFFAOYSA-N lithium;tributyltin Chemical compound CCCC[Sn]([Li])(CCCC)CCCC CKVWBMJEETWJTF-UHFFFAOYSA-N 0.000 description 1
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluenecarboxylic acid Natural products CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- CUIXFHFVVWQXSW-UHFFFAOYSA-N methyl-[3-(oxiran-2-ylmethoxy)propyl]-diphenoxysilane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C)CCCOCC1CO1 CUIXFHFVVWQXSW-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluenecarboxylic acid Natural products CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- UBOGEXSQACVGEC-UHFFFAOYSA-K phenyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1=CC=CC=C1 UBOGEXSQACVGEC-UHFFFAOYSA-K 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 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
- 238000012673 precipitation polymerization Methods 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000005838 radical anions Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- JHGCXUUFRJCMON-UHFFFAOYSA-J silicon(4+);tetraiodide Chemical compound [Si+4].[I-].[I-].[I-].[I-] JHGCXUUFRJCMON-UHFFFAOYSA-J 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FPTCHHKCUSVAOO-UHFFFAOYSA-N tert-butyl-dimethyl-propoxysilane Chemical compound CCCO[Si](C)(C)C(C)(C)C FPTCHHKCUSVAOO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VJHDVMPJLLGYBL-UHFFFAOYSA-N tetrabromogermane Chemical compound Br[Ge](Br)(Br)Br VJHDVMPJLLGYBL-UHFFFAOYSA-N 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- CUDGTZJYMWAJFV-UHFFFAOYSA-N tetraiodogermane Chemical compound I[Ge](I)(I)I CUDGTZJYMWAJFV-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- MWNSUONCJRRKFE-UHFFFAOYSA-N tributyl(chloro)germane Chemical compound CCCC[Ge](Cl)(CCCC)CCCC MWNSUONCJRRKFE-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- 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
- C08F236/10—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 with vinyl-aromatic monomers
-
- 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
- C08F8/10—Acylation
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- 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
- C08K3/02—Elements
- C08K3/06—Sulfur
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
- C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
-
- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2296—Oxides; Hydroxides of metals of zinc
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Tires In General (AREA)
Description
(式中、R1は一価有機基であり、R2は二価有機基であり、R3はヒドロカルビル基であり、各R4は独立して水素原子もしくは一価有機基であり、またはR3はヒドロカルビレン基を形成するためにR4と結合し、各αは独立して酸素原子または硫黄原子であり、但し、R2は非環式二価有機基、ヘテロ環式二価有機基、ヘテロ原子を欠く非芳香族環状二価有機基、またはヘテロ原子を欠く限り芳香環を含む二価有機基であり、R2がヘテロ原子を欠く芳香環を含む二価有機基である場合、シリル化アミノ基は芳香環に直接結合されない)、または式II、
(式中、R1は一価有機基であり、R2は二価有機基であり、各R4は独立して水素原子もしくは一価有機基であり、または2つのR4基は二価有機基を形成するために結合し、各αは独立して酸素原子または硫黄原子であり、但し、R2は非環式二価有機基、ヘテロ環式二価有機基、ヘテロ原子を欠く非芳香族環状有機基、またはヘテロ原子を欠く限り芳香環を含む二価有機基であり、R2がヘテロ原子を欠く芳香環を含む二価有機基である場合、シリル化アミノ基は芳香環に直接結合されない)によって定義されるシリル化アミノ基を含有する、カルボン酸またはチオカルボン酸エステルと反応するステップを含む。
(式中、R1は一価有機基であり、各αは独立して酸素原子または硫黄原子である)によって定義されてもよい。以下に説明されるように、一価有機基R1はヒドロカルビル基またはシリル基であってもよい。当業者には理解されるように、両方のα原子が酸素原子である場合は、エステル基はカルボン酸エステル基と呼ばれてもよい。一方または両方のα原子が硫黄原子である場合、エステル基はチオカルボン酸エステル基と呼ばれてもよい。より具体的には、一方のα原子が硫黄原子(いずれかのα原子)であり、他方のα原子が酸素原子である場合、エステル基はモノチオカルボン酸エステル基と呼ばれてもよく、対応するエステルはモノチオカルボン酸エステルと呼ばれてもよい。両方のα原子が硫黄原子である場合は、エステル基はジチオカルボン酸エステル基と呼ばれてもよく、対応するエステルはジチオカルボン酸エステルと呼ばれてもよい。本明細書のため、チオカルボン酸エステル基への言及は、モノチオカルボン酸エステル基およびジチオカルボン酸エステル基の両方を包含してもよく、チオカルボン酸エステルへの言及は、モノチオカルボン酸エステルおよびジチオカルボン酸エステルの両方を包含してもよい。
(式中、R1は一価有機基であり、R2は二価有機基であり、R3はヒドロカルビル基であり、各R4は独立して水素原子もしくは一価有機基であり、またはR3はヒドロカルビレン基を形成するためにR4と結合し、各αは独立して酸素原子または硫黄原子である)によって定義されてもよい。1つまたは複数の実施形態では、二価有機基R2は、1つもしくは複数の添加されたシリル化アミノ基、および/または1つもしくは複数の添加されたカルボン酸またはチオカルボン酸エステル基を含有してもよい。
(式中、R1は一価有機基であり、R2は二価有機基であり、各R4は独立して水素原子もしくは一価有機基であり、または2つのR4は二価有機基を形成するために結合し、各αは独立して酸素原子または硫黄原子である)によって表されてもよい。1つまたは複数の実施形態では、二価有機基R2は、1つもしくは複数の添加されたシリル化アミノ基、および/または1つもしくは複数の添加されたカルボン酸またはチオカルボン酸エステル基を含有してもよい。
(式中、R1は一価有機基であり、R2は二価有機基であり、R5はヒドロカルビレン基であり、各R4は独立して水素原子もしくは一価有機基であり、各αは独立して酸素原子または硫黄原子である)によって表されてもよい。
(式中、R1は一価有機基であり、R2およびR6はそれぞれに独立して二価有機基であり、各R4は独立して水素原子もしくは一価有機基であり、各αは独立して酸素原子または硫黄原子である)によって表されてもよい。
例1.エチル3−[ビス(トリメチルシリル)アミノ]プロピオン酸(3−BTMSAEP)の合成
約7.23gのエチル3−アミノプロピオン酸塩酸塩、15.71gのトリエチルアミン、および10mlのトルエンを氷浴で冷却した丸底反応フラスコ内で混合した。この混合物に液滴の形でトルエン50ml中におけるトリメチルシリルトリフルオロメタンスルホン酸23.00gの溶液を添加した。得られた混合物を室温で39時間撹拌して二相混合物を得た。上層を別のフラスコに移し、底層を40mlのトルエンで抽出した。混合したトルエン溶液を真空下で蒸発させた。残留物を100mlのヘキサンで抽出し、ヘキサン層を真空下で蒸発させ、無色油としてエチル3−[ビス(トリメチルシリル)アミノ]プロピオン酸(3−BTMSAEP)を得た(11.03g、90%収率)。生成物の1H NMRデータ(C6D6、25℃、テトラメチルシラン参照)は以下の通りに示される、すなわちδ3.91(四重項、2H、OCH2プロトン)、3.21(多重項、2H、NCH2CH2プロトン)、2.36(多重項、2H、NCH2CH2プロトン)、0.91(三重項、3H、CH3プロトン)、0.07(一重項、18H、Si−CH3プロトン)である。1H NMRデータから、生成物の構造は以下の通りに決定された。
約9.24gのエチル4−アミノ安息香酸、14.88gのトリメチルアミン、および10mlのトルエンを、氷浴で冷却した丸底反応フラスコ内で混合した。この混合物に液滴の形でトルエン50ml中におけるトリメチルシリルトリフルオロメタンスルホン酸32.68gの溶液を添加した。得られた混合物を8時間加熱して二相混合物を得た。上層を別のフラスコに移し、底層を40mlのトルエンで抽出した。混合したトルエン溶液を真空下で蒸発させた。残留物を100mlのヘキサンで抽出し、ヘキサン層を真空下で蒸発させ、黄色油としてエチル4−[ビス(トリメチルシリル)アミノ]安息香酸(4−BTMSAEBZ)を得た(16.04g、93%を得た)。生成物の1H NMRデータ(C6D6、25℃、テトラメチルシラン参照)は以下の通りに示される、すなわちδ8.07(二重項、2H、芳香族プロトン)、6.76(二重項、2H、芳香族プロトン)、4.12(四重項、2H、CH2プロトン)、1.00(三重項、3H、CH3プロトン)、0.02(一重項、18H、Si−CH3プロトン)である。1H NMRデータから、生成物の構造は以下の通りに決定された。
タービンアジテーターブレードを備えた5ガロンの窒素パージされた反応器に、ヘキサン5100g、33.0重量%のスチレンのヘキサン溶液1278g、および22.0重量%の1,3−ブタジエンのヘキサン溶液7670gを添加した。反応器に1.6Mのn−ブチルリチウムのヘキサン溶液11.98mlおよび1.6Mの2,2−ビス(2’−テトラヒドロフリル)プロパンのヘキサン溶液3.95mlを装填した。反応器のジャケットに熱水を適用することによりバッチを加熱した。一旦バッチ温度が50℃に達すると、反応器のジャケットを冷水で冷却した。
タービンアジテーターブレードを備えた2ガロンの窒素パージされた反応器に、ヘキサン1595g、34.0重量%のスチレンのヘキサン溶液400g、および22.3重量%の1,3−ブタジエンのヘキサン溶液2440gを添加した。反応器に1.6Mのn−ブチルリチウムのヘキサン溶液1.70mlおよび1.6Mの2,2−ビス(2’−テトラヒドロフリル)プロパンのヘキサン溶液0.56mlを装填した。反応器のジャケットに熱水を適用することによりバッチを加熱した。一旦バッチ温度が50℃に達すると、反応器のジャケットを冷水で冷却した。触媒添加の2.5時間後、重合混合物は、12重量%の2,6−ジ−tert−ブチル−4−メチルフェノール液のイソプロパノール溶液30mlを添加して失活させ、2,6−ジ−tert−ブチル−4−メチルフェノール5gを含有するイソプロパノール12リットルで凝固させ、次いでドラム乾燥した。得られた未修飾SBRの性質を表1にまとめる。
例3において合成したリビングポリマーセメント約343gを反応器から窒素パージされボトルに移し、続いて0.45Mのエチル3−[ビス(トリメチルシリル)アミノ]プロピオン酸(3−BTMSAEP)のヘキサン溶液0.95mlを添加した。ボトルを65℃に維持した水浴中で30分間混転した。得られたポリマーセメントを、12重量%の2,6−ジ−tert−ブチル−4−メチルフェノール液のイソプロパノール溶液3mlで失活させ、2,6−ジ−tert−ブチル−4−メチルフェノール0.5gを含有するイソプロパノール2リットルで凝固させ、次いでドラム乾燥した。得られた3−BTMSAEP修飾ポリマーの性質を表1にまとめる。
例3において合成したリビングポリマーセメント約335gを反応器から窒素パージされたボトルに移し、続いて0.45Mのエチル4−[ビス(トリメチルシリル)アミノ]安息香酸(4−BTMSAEBz)のヘキサン溶液0.93mlを添加した。ボトルを65℃に維持した水浴中で30分間混転した。得られたポリマーセメントを、12重量%の2,6−ジ−tert−ブチル−4−メチルフェノール液のイソプロパノール溶液3mlで失活させ、2,6−ジ−tert−ブチル−4−メチルフェノール0.5gを含有するイソプロパノール2リットルで凝固させ、次いでドラム乾燥した。得られた4−BTMSAEBz修飾ポリマーの性質を表1にまとめる。
例3〜6で生成したポリ(スチレン−co−ブタジエン)試料を、カーボンブラックで充填したゴム化合物の状態で評価した。加硫物の組成を表2に示した。表中、数値は全ゴムの100重量部当たりの重量部(phr)として表されている。
Claims (7)
- 官能化ポリマーを調製するための方法であって、
(i)反応性ポリマーを形成するためにモノマーをアニオン開始剤で重合するステップと、
(ii)前記反応性ポリマーが、非環式部分、ヘテロ環式部分、および非芳香族環式部分からなる群から選択される部分に直接結合されるシリル化アミノ基を含有する、カルボン酸またはチオカルボン酸エステルと反応するステップと、を含む方法。 - 前記シリル化アミノ基は、ビス(トリヒドロカルビルシリル)アミノ、ビス(ジヒドロカルビルヒドロシリル)アミノ、1−アザ−ジシラ−1−シクロヒドロカルビル、(トリヒドロカルビルシリル)(ヒドロカルビル)アミノ、(ジヒドロカルビルヒドロシリル)(ヒドロカルビル)アミノ、および1−アザ−2−シラ−1−シクロヒドロカルビル基からなる群から選択される、請求項1に記載の方法。
- 前記アニオン開始剤は有機リチウム化合物であり、前記モノマーは共役ジエンモノマーおよび必要に応じてそれで共重合可能なモノマーを含む、請求項1に記載の方法。
- 前記カルボン酸またはチオカルボン酸エステル基およびシリル化アミノ基を含有する前記カルボン酸またはチオカルボン酸エステルの両方は、非環式部分、ヘテロ環式部分、および非芳香族環式部分からなる群から選択される部分に直接結合される、請求項1に記載の方法。
- 官能化ポリマーを調製するための方法であって、
(i)反応性ポリマーを形成するためにモノマーをアニオン開始剤で重合するステップと、
(ii)前記反応性ポリマーが式I、
(式中、R1は一価有機基であり、R2は二価有機基であり、R3はヒドロカルビル基であり、各R4は独立して水素原子もしくは一価有機基であり、またはR3はヒドロカルビレン基を形成するためにR4と結合し、各αは独立して酸素原子または硫黄原子であり、但し、R2は非環式二価有機基、ヘテロ環式二価有機基、ヘテロ原子を欠く非芳香族環状二価有機基、またはヘテロ原子を欠く芳香環を含む二価有機基であり、R2がヘテロ原子を欠く芳香環を含む二価有機基である場合、前記シリル化アミノ基は前記芳香環に直接結合されない)、または式II、
(式中、R1は一価有機基であり、R2は二価有機基であり、各R4は独立して水素原子もしくは一価有機基であり、または2つのR4基は二価有機基を形成するために結合し、各αは独立して酸素原子または硫黄原子であり、但し、R2は非環式二価有機基、ヘテロ環式二価有機基、ヘテロ原子を欠く非芳香族環状二価有機基、またはヘテロ原子を欠く芳香環を含む二価有機基であり、R2がヘテロ原子を欠く芳香環を含む二価有機基である場合、前記シリル化アミノ基は前記芳香環に直接結合されない)によって定義されるシリル化アミノ基を含有する、カルボン酸またはチオカルボン酸エステルと反応するステップと、を含む方法。 - シリル化アミノ基を含有する前記カルボン酸またはチオカルボン酸エステルは、式III、
(式中、R1は一価有機基であり、R2は二価有機基であり、R5はヒドロカルビレン基であり、各R4は独立して水素原子もしくは一価有機基であり、各αは独立して酸素原子または硫黄原子であり、但し、R2は非環式二価有機基、ヘテロ環式二価有機基、ヘテロ原子を欠く非芳香族環状二価有機基、またはヘテロ原子を欠く芳香環を含む二価有機基であり、R2がヘテロ原子を欠く芳香環を含む二価有機基である場合、前記シリル化アミノ基は前記芳香環に直接結合されない)、または式IV、
(式中、R1は一価有機基であり、R2およびR6はそれぞれ独立して二価有機基であり、各R4は独立して水素原子もしくは一価有機基であり、各αは独立して酸素原子または硫黄原子であり、但し、R2は非環式二価有機基、ヘテロ環式二価有機基、ヘテロ原子を欠く非芳香族環状二価有機基、またはヘテロ原子を欠く芳香環を含む二価有機基であり、R2がヘテロ原子を欠く芳香環を含む二価有機基である場合、前記シリル化アミノ基は芳香環に直接結合される)によって定義される、請求項5に記載の方法。 - 前記アニオン開始剤は有機リチウム化合物であり、前記モノマーは共役ジエンモノマーおよび必要に応じてそれで共重合可能なモノマーを含む、請求項5に記載の方法。
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US10179479B2 (en) | 2015-05-19 | 2019-01-15 | Bridgestone Americas Tire Operations, Llc | Plant oil-containing rubber compositions, tread thereof and race tires containing the tread |
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Family Cites Families (72)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1300240B (de) | 1964-01-22 | 1969-07-31 | Bayer Ag | Verfahren zur Herstellung von Polymerisaten konjugierter Diolefine |
US3652516A (en) | 1969-02-10 | 1972-03-28 | Phillips Petroleum Co | Polymerization of conjugated dienes or monovinyl aromatic monomers with multifunctional initiators from diisopropenylbenzene |
US3873489A (en) | 1971-08-17 | 1975-03-25 | Degussa | Rubber compositions containing silica and an organosilane |
US3978103A (en) | 1971-08-17 | 1976-08-31 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Sulfur containing organosilicon compounds |
BE787691A (fr) | 1971-08-17 | 1973-02-19 | Degussa | Composes organosiliciques contenant du soufre |
SU580840A3 (ru) | 1974-02-07 | 1977-11-15 | Дегусса (Фирма) | Способ получени серосодержащих кремнийорганических соединений |
US4002594A (en) | 1975-07-08 | 1977-01-11 | Ppg Industries, Inc. | Scorch retardants for rubber reinforced with siliceous pigment and mercapto-type coupling agent |
JPS58136623A (ja) | 1982-02-05 | 1983-08-13 | Japan Synthetic Rubber Co Ltd | ポリジエン/ポリペプチドブロック共重合体の製造方法 |
US4429091A (en) | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Oligomeric oxolanyl alkanes as modifiers for polymerization of dienes using lithium-based initiators |
JPS62101640A (ja) * | 1985-10-29 | 1987-05-12 | Japan Synthetic Rubber Co Ltd | ゴム組成物 |
JPH0686500B2 (ja) * | 1985-12-10 | 1994-11-02 | 日本合成ゴム株式会社 | 共役ジオレフィン系重合体の製造方法 |
US4906706A (en) | 1986-09-05 | 1990-03-06 | Japan Synthetic Rubber Co., Ltd. | Modified conjugated diene polymer and process for production thereof |
US5064910A (en) | 1986-09-05 | 1991-11-12 | Japan Synthetic Rubber Co., Ltd. | Preparation of conjugated diene polymers modified with an organo-tin or germanium halide |
IT1230756B (it) | 1989-02-17 | 1991-10-29 | Enichem Elastomers | Metodo per la preparazione di polibutadiene a lavorabilita' migliorata. |
US5268439A (en) | 1991-01-02 | 1993-12-07 | Bridgestone/Firestone, Inc. | Tin containing elastomers and products having reduced hysteresis properties |
FR2673187B1 (fr) | 1991-02-25 | 1994-07-01 | Michelin & Cie | Composition de caoutchouc et enveloppes de pneumatiques a base de ladite composition. |
US5260123A (en) | 1991-06-28 | 1993-11-09 | Bridgestone Corporation | Block copolymers of polysiloxanes and copolymers of conjugated dienes and aromatic vinyl compounds, and multilayer structures containing same |
JP3211274B2 (ja) | 1991-08-27 | 2001-09-25 | 旭化成株式会社 | 共役ジエン系重合体の製造方法 |
JP3230532B2 (ja) | 1991-08-28 | 2001-11-19 | 旭化成株式会社 | 共役ジエン系重合体の製造法 |
WO1993023453A1 (en) | 1992-05-20 | 1993-11-25 | Nippon Zeon Company Ltd. | Polyamino acid/polyisoprene block copolymer, production thereof, article molded therefrom, and production thereof |
US5329005A (en) | 1992-10-02 | 1994-07-12 | Bridgestone Corporation | Soluble anionic polymerization initiators and preparation thereof |
US5332810A (en) | 1992-10-02 | 1994-07-26 | Bridgestone Corporation | Solubilized anionic polymerization initiator and preparation thereof |
US5393721A (en) | 1992-10-16 | 1995-02-28 | Bridgestone Corporation | Anionic polymerization initiators and reduced hysteresis products therefom |
DE69315965T2 (de) | 1992-10-30 | 1998-04-16 | Bridgestone Corp | Lösliche, anionische Polymerisationsinitiatoren und erhaltene Produkte |
ES2119008T3 (es) | 1993-04-30 | 1998-10-01 | Bridgestone Corp | Iniciadores de polimerizacion anionica y productos de histeresis reducida de los mismos. |
JP3769294B2 (ja) | 1993-07-30 | 2006-04-19 | 日本ゼオン株式会社 | 変性共役ジエン系重合体およびその製造方法ならびにその組成物 |
US5491230A (en) | 1993-12-29 | 1996-02-13 | Bridgestone Corporation | Anionic polymerization initiators containing adducts of cyclic secondary amines and conjugated dienes, and products therefrom |
DE4436059A1 (de) | 1994-10-10 | 1996-04-11 | Bayer Ag | Verfahren zur Herstellung von mittels Nd-Katalysatoren polymerisierten Dienkautschuken mit niedrigem cold-flow und geringem Eigengeruch |
US5521309A (en) | 1994-12-23 | 1996-05-28 | Bridgestone Corporation | Tertiary-amino allyl-or xylyl-lithium initiators and method of preparing same |
US5496940A (en) | 1995-02-01 | 1996-03-05 | Bridgestone Corporation | Alkyllithium compounds containing cyclic amines and their use in polymerization |
US5574109A (en) | 1995-02-01 | 1996-11-12 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
US5580919A (en) | 1995-03-14 | 1996-12-03 | The Goodyear Tire & Rubber Company | Silica reinforced rubber composition and use in tires |
US5674932A (en) | 1995-03-14 | 1997-10-07 | The Goodyear Tire & Rubber Company | Silica reinforced rubber composition and use in tires |
JP3555809B2 (ja) | 1995-06-19 | 2004-08-18 | 株式会社ブリヂストン | ラジアルタイヤ |
AT405285B (de) | 1995-09-07 | 1999-06-25 | Semperit Ag | Kautschukmischung |
US5583245A (en) | 1996-03-06 | 1996-12-10 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
US5719207A (en) | 1996-03-18 | 1998-02-17 | The Goodyear Tire & Rubber Company | Silica reinforced rubber composition and tire with tread |
US5696197A (en) | 1996-06-21 | 1997-12-09 | The Goodyear Tire & Rubber Company | Heterogeneous silica carbon black-filled rubber compound |
JP3606411B2 (ja) | 1996-07-10 | 2005-01-05 | 株式会社ブリヂストン | タイヤ加硫成型用金型およびその製造方法 |
JP3117645B2 (ja) | 1996-09-03 | 2000-12-18 | 株式会社ブリヂストン | 空気入りラジアルタイヤ |
US5663396A (en) | 1996-10-31 | 1997-09-02 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
US5786441A (en) | 1996-12-31 | 1998-07-28 | Bridgestone Corporation | Polymers, elastomeric compounds and products thereof, derived from novel amine compounds containing side-chain organolithium moieties |
US5684171A (en) | 1997-02-11 | 1997-11-04 | The Goodyear Tire & Rubber Company | Process for the preparation of organosilicon polysulfide compounds |
US5684172A (en) | 1997-02-11 | 1997-11-04 | The Goodyear Tire & Rubber Company | Process for the preparation of organosilicon polysulfide compounds |
JP3724125B2 (ja) | 1997-07-15 | 2005-12-07 | Jsr株式会社 | 共役ジエン系重合体の製造方法 |
JP4489194B2 (ja) | 1997-03-05 | 2010-06-23 | Jsr株式会社 | 共役ジエン系重合体の製造方法 |
ES2198651T3 (es) | 1997-03-05 | 2004-02-01 | Jsr Corporation | Metodo para producir polimeros dieno conjugados. |
US6221943B1 (en) | 1997-07-11 | 2001-04-24 | Bridgestone Corporation | Processability of silica-filled rubber stocks |
US6525118B2 (en) | 1997-07-11 | 2003-02-25 | Bridgestone Corporation | Processability of silica-filled rubber stocks with reduced hysteresis |
US6384117B1 (en) | 1997-07-11 | 2002-05-07 | Bridgestone Corporation | Processability of silica-filled rubber stocks |
US6414061B1 (en) | 1997-08-21 | 2002-07-02 | Crompton Corporation | Blocked mercaptosilane coupling agents for filled rubbers |
US5971046A (en) | 1997-09-17 | 1999-10-26 | Bridgestone/Firestone, Inc. | Method and apparatus for bonding an active tag to a patch and a tire |
DE60041550D1 (de) | 1999-11-12 | 2009-03-26 | Bridgestone Corp | Modifizierte polymere hergestellt mit katalysator auf basys von lanthaniden |
EP1099711B1 (en) | 1999-11-12 | 2006-03-29 | JSR Corporation | Modified conjugated diene polymer, method of producing it and rubber composition comprising the same |
US6977281B1 (en) | 1999-11-12 | 2005-12-20 | Bridgestone Corporation | Modified polymers prepared with lanthanide-based catalysts |
FR2802542A1 (fr) | 1999-12-20 | 2001-06-22 | Michelin Soc Tech | Composition de caoutchouc vulcanisable pour la fabrication d'un pneumatique et pneumatique dont la bande de roulement comprend une telle composition |
US6590017B1 (en) | 2000-05-15 | 2003-07-08 | Bridgestone Corporation | Processability of silica-reinforced rubber containing an amide compound |
US6608145B1 (en) | 2000-10-13 | 2003-08-19 | Bridgestone Corporation | Silica-reinforced rubber compounded with an organosilane tetrasulfide silica coupling agent at high mixing temperature |
ES2412979T3 (es) | 2000-11-10 | 2013-07-15 | Bridgestone Corporation | Cis-1,4-polibutadieno altamente funcionalizado preparado usando nuevos agentes de funcionalización |
DE60231905D1 (de) * | 2001-09-27 | 2009-05-20 | Jsr Corp | (co)polymerkautschuk auf basis von konjugiertem diolefin, verfahren zur herstellung von (co)polymerkautschuk, kautschukzusammensetzung, verbundwerkstoff und reifen |
US6579949B1 (en) | 2001-10-30 | 2003-06-17 | Bridgestone Corporation | Preparation of low hysteresis rubber by reacting a lithium polymer with a sulfur containing reagent |
JP4522947B2 (ja) | 2002-10-30 | 2010-08-11 | 株式会社ブリヂストン | モノマーのアニオン重合に硫黄含有開始剤を使用する方法 |
ES2588177T3 (es) | 2004-03-02 | 2016-10-31 | Bridgestone Corporation | Proceso de polimerización en masa |
BRPI0609075B1 (pt) * | 2005-04-15 | 2018-10-09 | Bridgestone Corp | copolímero de dieno conjugado modificado, composições de borracha e pneus |
US7335712B2 (en) | 2005-04-21 | 2008-02-26 | Bridgestone Corporation | Process of producing a siloxy-functionalized polymer |
US20060264590A1 (en) | 2005-05-20 | 2006-11-23 | Bridgestone Corporation | Anionic polymerization initiators and polymers therefrom |
US7868110B2 (en) | 2005-05-20 | 2011-01-11 | Bridgestone Corporation | Anionic polymerization initiators and polymers therefrom |
KR101598638B1 (ko) * | 2007-06-18 | 2016-02-29 | 가부시키가이샤 브리지스톤 | 아미노기 함유 할로실란으로 관능화된 중합체 |
JP2009108277A (ja) * | 2007-11-01 | 2009-05-21 | Jsr Corp | ポリアミノ酸−ポリジエンブロック共重合体の製造方法 |
US8178641B2 (en) | 2007-10-30 | 2012-05-15 | Jsr Corporation | Amino group-containing conjugated diene polymer and method for producing the same, and block copolymer and method for producing the same |
RU2492189C2 (ru) * | 2007-12-28 | 2013-09-10 | Бриджстоун Корпорейшн | Функционализованный полимер и способы его получения и применения |
US20110077325A1 (en) * | 2009-09-30 | 2011-03-31 | Bridgestone Corporation | Functionalized polymers and methods for their manufacture |
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- 2012-03-29 RU RU2013147979/04A patent/RU2599633C2/ru active
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- 2012-03-29 CN CN201280025830.9A patent/CN103562237B/zh active Active
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BR112013025124A2 (pt) | 2021-06-01 |
CN103562237B (zh) | 2016-02-17 |
CN103562237A (zh) | 2014-02-05 |
RU2013147979A (ru) | 2015-05-10 |
EP2699606B1 (en) | 2016-09-28 |
SG194665A1 (en) | 2013-12-30 |
EP2699606A4 (en) | 2015-01-21 |
EP2699606A2 (en) | 2014-02-26 |
US20140018500A1 (en) | 2014-01-16 |
WO2012135451A3 (en) | 2013-01-03 |
WO2012135451A2 (en) | 2012-10-04 |
BR112013025124B1 (pt) | 2022-03-29 |
US9403919B2 (en) | 2016-08-02 |
RU2599633C2 (ru) | 2016-10-10 |
JP2014509686A (ja) | 2014-04-21 |
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