RU2565706C2 - Эластомер на основе функционализированного диена и композиция каучука, содержащая его - Google Patents
Эластомер на основе функционализированного диена и композиция каучука, содержащая его Download PDFInfo
- Publication number
- RU2565706C2 RU2565706C2 RU2012118621/05A RU2012118621A RU2565706C2 RU 2565706 C2 RU2565706 C2 RU 2565706C2 RU 2012118621/05 A RU2012118621/05 A RU 2012118621/05A RU 2012118621 A RU2012118621 A RU 2012118621A RU 2565706 C2 RU2565706 C2 RU 2565706C2
- Authority
- RU
- Russia
- Prior art keywords
- elastomer
- diene
- silanol
- star
- tin
- Prior art date
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 160
- 239000000806 elastomer Substances 0.000 title claims abstract description 110
- 239000000203 mixture Substances 0.000 title claims abstract description 86
- 150000001993 dienes Chemical class 0.000 title claims abstract description 41
- 239000005060 rubber Substances 0.000 title claims description 50
- -1 polysiloxane Polymers 0.000 claims abstract description 45
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 29
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000005372 silanol group Chemical group 0.000 claims abstract description 26
- 229920003244 diene elastomer Polymers 0.000 claims description 60
- 229920001577 copolymer Polymers 0.000 claims description 40
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 31
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 30
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- 239000011256 inorganic filler Substances 0.000 claims description 28
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 27
- 230000003014 reinforcing effect Effects 0.000 claims description 20
- 239000012763 reinforcing filler Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000011159 matrix material Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 238000007306 functionalization reaction Methods 0.000 claims description 15
- 239000000377 silicon dioxide Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000011265 semifinished product Substances 0.000 claims description 7
- 235000012239 silicon dioxide Nutrition 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 230000003750 conditioning effect Effects 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims 1
- 238000012545 processing Methods 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 230000006866 deterioration Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 229910052718 tin Inorganic materials 0.000 description 22
- 239000006229 carbon black Substances 0.000 description 15
- 235000019241 carbon black Nutrition 0.000 description 15
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000000945 filler Substances 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000523 sample Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 229920001021 polysulfide Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 241001441571 Hiodontidae Species 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000005077 polysulfide Substances 0.000 description 6
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- 239000003643 water by type Substances 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- 229910020175 SiOH Inorganic materials 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000001542 size-exclusion chromatography Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006085 branching agent Substances 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
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- 239000012766 organic filler Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 230000000930 thermomechanical effect Effects 0.000 description 4
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
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- 125000003636 chemical group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
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- 150000003254 radicals Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004071 soot Substances 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical compound CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
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- 238000009826 distribution Methods 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
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- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
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- DGLJYEKNUTVPAE-UHFFFAOYSA-N 2,4,6-triethyl-2,4,6-trimethyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound CC[Si]1(C)O[Si](C)(CC)O[Si](C)(CC)O1 DGLJYEKNUTVPAE-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- HMWCQCYUKQZPRA-UHFFFAOYSA-N 2,4-dimethyl-3-methylidenepent-1-ene Chemical compound CC(C)C(=C)C(C)=C HMWCQCYUKQZPRA-UHFFFAOYSA-N 0.000 description 1
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- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
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- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000006235 reinforcing carbon black Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium 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
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical group C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
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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
- C08C19/30—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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- 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
- 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
- C08L15/00—Compositions of rubber derivatives
Landscapes
- 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)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0957030A FR2951178B1 (fr) | 2009-10-08 | 2009-10-08 | Elastomere dienique fonctionnalise et composition de caoutchouc le contenant. |
| FR0957030 | 2009-10-08 | ||
| PCT/EP2010/065030 WO2011042507A1 (fr) | 2009-10-08 | 2010-10-07 | Elastomere dienique fonctionnalise et composition de caoutchouc le contenant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012118621A RU2012118621A (ru) | 2013-11-20 |
| RU2565706C2 true RU2565706C2 (ru) | 2015-10-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012118621/05A RU2565706C2 (ru) | 2009-10-08 | 2010-10-07 | Эластомер на основе функционализированного диена и композиция каучука, содержащая его |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9670291B2 (https=) |
| EP (1) | EP2486065B1 (https=) |
| JP (1) | JP6026279B2 (https=) |
| KR (2) | KR20170045369A (https=) |
| CN (1) | CN102549019B (https=) |
| BR (1) | BR112012008027B1 (https=) |
| FR (1) | FR2951178B1 (https=) |
| PL (1) | PL2486065T3 (https=) |
| RU (1) | RU2565706C2 (https=) |
| WO (1) | WO2011042507A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020106173A1 (en) | 2018-11-23 | 2020-05-28 | Public Joint Stock Company "Sibur Holding" | Polymer composition and a method for preparing thereof |
| RU2748399C2 (ru) * | 2016-10-26 | 2021-05-25 | Пирелли Тайр С.П.А. | Новые армирующие материалы, эластомерные композиции и шины для колес транспортных средств, их содержащие |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6228908B1 (en) * | 1997-07-11 | 2001-05-08 | Bridgestone Corporation | Diene polymers and copolymers incorporating partial coupling and terminals formed from hydrocarboxysilane compounds |
| EP1122281A1 (fr) * | 2000-02-07 | 2001-08-08 | Société de Technologie Michelin | Pneumatiques pour lourdes charges, et utilisation d'une composition de caoutchouc pour retarder l'usure irrégulière sur ces pneumatiques. |
| RU2320683C2 (ru) * | 2000-10-13 | 2008-03-27 | Сосьете Де Текнолоджи Мишлен | Эластомерная смесь, содержащая в качестве связывающего агента полифункциональный органосилан |
| EP2098541A1 (en) * | 2006-12-27 | 2009-09-09 | JSR Corporation | Method for producing modified conjugated diene polymer, modified conjugated diene polymer, and rubber composition |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3393182A (en) | 1965-02-23 | 1968-07-16 | Phillips Petroleum Co | Prevention of cold flow in polymers of conjugated dienes |
| EP0299074B1 (en) | 1987-01-14 | 1992-01-29 | Bridgestone Corporation | Tire |
| EP0447066B2 (en) | 1990-03-02 | 2000-08-16 | Bridgestone Corporation | Pneumatic tyres |
| FR2722503A1 (fr) | 1994-07-15 | 1996-01-19 | Michelin & Cie | Polymeres dieniques fonctionnels, leur procede de preparation et leur utilisation dans des compositions elastomeres chargees a la silice utilisables pour des enveloppes de pneumatiques |
| EP1637556A1 (en) | 1995-05-22 | 2006-03-22 | Cabot Corporation | Elastomer compounds incorporating silicon-treated carbon blacks |
| FR2740778A1 (fr) | 1995-11-07 | 1997-05-09 | Michelin & Cie | Composition de caoutchouc a base de silice et de polymere dienique fonctionalise ayant une fonction silanol terminale |
| FR2744127A1 (fr) * | 1996-01-26 | 1997-08-01 | Michelin & Cie | Composition de caoutchouc a base d'un polymere dienique ayant une fonction silanol et comprenant un derive organosilane |
| FR2763074B1 (fr) | 1997-05-07 | 1999-06-25 | Michelin & Cie | Composition de caoutchouc a base de noir de carbone ayant de la silice fixee a sa surface et de polymere dyenique fonctionalise ou modifie par des fonctions silanols |
| WO2002010269A2 (fr) | 2000-07-31 | 2002-02-07 | Societe De Technologie Michelin | Bande de roulement pour pneumatique |
| KR100776926B1 (ko) | 2000-10-13 | 2007-11-20 | 소시에떼 드 테크놀로지 미쉐린 | 커플링제로서 사용하기 위한 다관능성 오가노실란 및 이의제조방법 |
| FR2823215B1 (fr) | 2001-04-10 | 2005-04-08 | Michelin Soc Tech | Pneumatique et bande de roulement de pneumatique comportant a titre d'agent de couplage un tetrasulfure de bis-alkoxysilane |
| EP1419195B1 (fr) | 2001-06-28 | 2010-04-21 | Société de Technologie Michelin | Bande de roulement pour pneumatique renforcee d'une silice a basse surface specifique |
| EP1404755A1 (fr) | 2001-06-28 | 2004-04-07 | Société de Technologie Michelin | Bande de roulement pour pneumatique renforcee d'une silice a tres basse surface specifique |
| ATE427969T1 (de) * | 2001-09-27 | 2009-04-15 | Jsr Corp | (co)polymerkautschuk auf basis von konjugiertem diolefin, verfahren zur herstellung von (co)polymerkautschuk, kautschukzusammensetzung, verbundwerkstoff und reifen |
| JP4126533B2 (ja) * | 2002-06-20 | 2008-07-30 | 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 |
| FR2866028B1 (fr) | 2004-02-11 | 2006-03-24 | Michelin Soc Tech | Systeme plastifiant pour composition de caoutchouc |
| US20060033909A1 (en) | 2004-07-23 | 2006-02-16 | Bowers Gerald M | Reticle particle calibration standards |
| FR2877348B1 (fr) | 2004-10-28 | 2007-01-12 | Michelin Soc Tech | Systeme plastifiant pour composition de caoutchouc |
| FR2880349B1 (fr) | 2004-12-31 | 2009-03-06 | Michelin Soc Tech | Nanoparticules de polyvinylaromatique fonctionnalise |
| FR2880354B1 (fr) | 2004-12-31 | 2007-03-02 | Michelin Soc Tech | Composition elastomerique renforcee d'une charge de polyvinylaromatique fonctionnalise |
| FR2886305B1 (fr) | 2005-05-26 | 2007-08-10 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un agent de couplage organosilicique et un agent de recouvrement de charge inorganique |
| FR2886306B1 (fr) | 2005-05-26 | 2007-07-06 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un agent de couplage organosiloxane |
| FR2886304B1 (fr) | 2005-05-26 | 2007-08-10 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un systeme de couplage organosilicique |
| FR2889538B1 (fr) | 2005-08-08 | 2007-09-14 | Michelin Soc Tech | Systeme plastifiant pour compsition de caoutchouc. |
| FR2903411B1 (fr) | 2006-07-06 | 2012-11-02 | Soc Tech Michelin | Nanoparticules de polymere vinylique fonctionnalise |
| FR2903416B1 (fr) | 2006-07-06 | 2008-09-05 | Michelin Soc Tech | Composition elastomerique renforcee d'une charge de polymere vinylique non aromatique fonctionnalise |
| JP5611585B2 (ja) * | 2007-03-23 | 2014-10-22 | Jsr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、及びゴム組成物 |
| BRPI0705025A2 (pt) | 2007-12-14 | 2009-08-11 | Petroflex Ind E Com S A | produto de copolìmero de 1,3-butadieno e estireno, funcionalizado nas extremidades das suas cadeias poliméricas e seu processo de preparação |
| BRPI0704674A2 (pt) * | 2007-12-14 | 2009-08-11 | Petroflex Ind E Com S A | processo para preparação de copolìmero de 1,3-butadieno e estireno contendo em sua cadeia principal segmento aleatório, seguido de bloco com estrutura diferenciada da cadeia principal, homopolimérico ou copolimérico, funcionalizado e produto obtido a partir do mesmo |
| EP2070952A1 (en) * | 2007-12-14 | 2009-06-17 | Continental Aktiengesellschaft | Vulcanizable rubber mixture and its use for rubber products |
-
2009
- 2009-10-08 FR FR0957030A patent/FR2951178B1/fr not_active Expired - Fee Related
-
2010
- 2010-10-07 WO PCT/EP2010/065030 patent/WO2011042507A1/fr not_active Ceased
- 2010-10-07 KR KR1020177010265A patent/KR20170045369A/ko not_active Ceased
- 2010-10-07 RU RU2012118621/05A patent/RU2565706C2/ru active
- 2010-10-07 EP EP10770750.7A patent/EP2486065B1/fr active Active
- 2010-10-07 CN CN201080044753.2A patent/CN102549019B/zh active Active
- 2010-10-07 BR BR112012008027-0A patent/BR112012008027B1/pt not_active IP Right Cessation
- 2010-10-07 US US13/500,942 patent/US9670291B2/en not_active Expired - Fee Related
- 2010-10-07 PL PL10770750T patent/PL2486065T3/pl unknown
- 2010-10-07 KR KR1020127011793A patent/KR20120093269A/ko not_active Ceased
- 2010-10-07 JP JP2012532597A patent/JP6026279B2/ja not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6228908B1 (en) * | 1997-07-11 | 2001-05-08 | Bridgestone Corporation | Diene polymers and copolymers incorporating partial coupling and terminals formed from hydrocarboxysilane compounds |
| EP1122281A1 (fr) * | 2000-02-07 | 2001-08-08 | Société de Technologie Michelin | Pneumatiques pour lourdes charges, et utilisation d'une composition de caoutchouc pour retarder l'usure irrégulière sur ces pneumatiques. |
| RU2320683C2 (ru) * | 2000-10-13 | 2008-03-27 | Сосьете Де Текнолоджи Мишлен | Эластомерная смесь, содержащая в качестве связывающего агента полифункциональный органосилан |
| EP2098541A1 (en) * | 2006-12-27 | 2009-09-09 | JSR Corporation | Method for producing modified conjugated diene polymer, modified conjugated diene polymer, and rubber composition |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2748399C2 (ru) * | 2016-10-26 | 2021-05-25 | Пирелли Тайр С.П.А. | Новые армирующие материалы, эластомерные композиции и шины для колес транспортных средств, их содержащие |
| US11091607B2 (en) | 2016-10-26 | 2021-08-17 | Pirelli Tyre S.P.A. | Reinforcement materials, elastomeric compositions and tyres for vehicles wheels comprising the same |
| WO2020106173A1 (en) | 2018-11-23 | 2020-05-28 | Public Joint Stock Company "Sibur Holding" | Polymer composition and a method for preparing thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120093269A (ko) | 2012-08-22 |
| US20120252928A1 (en) | 2012-10-04 |
| CN102549019A (zh) | 2012-07-04 |
| PL2486065T3 (pl) | 2015-06-30 |
| CN102549019B (zh) | 2014-12-24 |
| JP2013507468A (ja) | 2013-03-04 |
| BR112012008027A8 (pt) | 2018-01-02 |
| WO2011042507A1 (fr) | 2011-04-14 |
| BR112012008027A2 (pt) | 2016-03-15 |
| EP2486065B1 (fr) | 2014-12-24 |
| EP2486065A1 (fr) | 2012-08-15 |
| JP6026279B2 (ja) | 2016-11-16 |
| KR20170045369A (ko) | 2017-04-26 |
| FR2951178A1 (fr) | 2011-04-15 |
| US9670291B2 (en) | 2017-06-06 |
| BR112012008027B1 (pt) | 2019-08-13 |
| RU2012118621A (ru) | 2013-11-20 |
| FR2951178B1 (fr) | 2012-08-17 |
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