JP3623332B2 - シラノール官能基を有しオルガノシラン誘導体を含むジエンポリマーを主成分として含有するゴム組成物 - Google Patents
シラノール官能基を有しオルガノシラン誘導体を含むジエンポリマーを主成分として含有するゴム組成物 Download PDFInfo
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- JP3623332B2 JP3623332B2 JP01261797A JP1261797A JP3623332B2 JP 3623332 B2 JP3623332 B2 JP 3623332B2 JP 01261797 A JP01261797 A JP 01261797A JP 1261797 A JP1261797 A JP 1261797A JP 3623332 B2 JP3623332 B2 JP 3623332B2
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- composition
- functionalized
- silanol
- carbon black
- silica
- 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.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 128
- 229920000642 polymer Polymers 0.000 title claims abstract description 73
- 229920001971 elastomer Polymers 0.000 title claims abstract description 53
- 125000005372 silanol group Chemical group 0.000 title claims abstract description 44
- 239000005060 rubber Substances 0.000 title claims abstract description 27
- 150000001282 organosilanes Chemical class 0.000 title claims abstract description 10
- 150000001993 dienes Chemical class 0.000 title claims description 40
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 90
- -1 polysiloxane Polymers 0.000 claims abstract description 58
- 239000006229 carbon black Substances 0.000 claims abstract description 45
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 44
- 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 22
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000000945 filler Substances 0.000 claims abstract description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 229920000768 polyamine Chemical group 0.000 claims abstract description 6
- 238000012545 processing Methods 0.000 claims description 27
- 239000000806 elastomer Substances 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 239000012763 reinforcing filler Substances 0.000 claims description 17
- 238000004073 vulcanization Methods 0.000 claims description 15
- 229920003244 diene elastomer Polymers 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- 238000005096 rolling process Methods 0.000 claims description 4
- 244000043261 Hevea brasiliensis Species 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 229920003052 natural elastomer Polymers 0.000 claims description 3
- 229920001194 natural rubber Polymers 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 229920001195 polyisoprene Polymers 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 230000002787 reinforcement Effects 0.000 claims description 2
- XDDVRYDDMGRFAZ-UHFFFAOYSA-N thiobenzophenone Chemical compound C=1C=CC=CC=1C(=S)C1=CC=CC=C1 XDDVRYDDMGRFAZ-UHFFFAOYSA-N 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000004615 ingredient Substances 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 3
- 150000002466 imines Chemical group 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000000879 imine group Chemical group 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 235000019241 carbon black Nutrition 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 12
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002897 diene group Chemical group 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000008366 benzophenones Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 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
- URXZKGGRKRRVDC-UHFFFAOYSA-N 1-[dimethoxy(propyl)silyl]oxyethanamine Chemical compound CCC[Si](OC)(OC)OC(C)N URXZKGGRKRRVDC-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 2
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 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
- 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
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical group CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- MCLXOMWIZZCOCA-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propan-1-amine Chemical compound CO[Si](C)(C)CCCN MCLXOMWIZZCOCA-UHFFFAOYSA-N 0.000 description 1
- HFRRNXHMVVEQKP-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;trimethoxy(propyl)silane Chemical compound C1CN=CN1.CCC[Si](OC)(OC)OC HFRRNXHMVVEQKP-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- JQWHQDBNJXSIJZ-UHFFFAOYSA-N 4-phenyl-N-trimethoxysilylbut-3-en-1-amine Chemical compound CO[Si](OC)(OC)NCCC=CC1=CC=CC=C1 JQWHQDBNJXSIJZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000010073 coating (rubber) Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 229940114937 microcrystalline wax Drugs 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 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
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YJDOIAGBSYPPCK-UHFFFAOYSA-N trimethoxy(3-morpholin-4-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCOCC1 YJDOIAGBSYPPCK-UHFFFAOYSA-N 0.000 description 1
- HXYMWKLNCJPAKW-UHFFFAOYSA-N trimethoxy(3-piperazin-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCNCC1 HXYMWKLNCJPAKW-UHFFFAOYSA-N 0.000 description 1
- PUFJKMYZVNKQCV-UHFFFAOYSA-N trimethoxy(3-piperidin-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCCCC1 PUFJKMYZVNKQCV-UHFFFAOYSA-N 0.000 description 1
- NGLLPRYTJGRGEU-UHFFFAOYSA-N trimethoxy(3-pyrrolidin-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCCC1 NGLLPRYTJGRGEU-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- C08K3/34—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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/006—Additives being defined by their surface area
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9601040 | 1996-01-26 | ||
| FR9601040A FR2744127A1 (fr) | 1996-01-26 | 1996-01-26 | Composition de caoutchouc a base d'un polymere dienique ayant une fonction silanol et comprenant un derive organosilane |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09208749A JPH09208749A (ja) | 1997-08-12 |
| JPH09208749A5 JPH09208749A5 (enExample) | 2004-12-02 |
| JP3623332B2 true JP3623332B2 (ja) | 2005-02-23 |
Family
ID=9488595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP01261797A Expired - Fee Related JP3623332B2 (ja) | 1996-01-26 | 1997-01-27 | シラノール官能基を有しオルガノシラン誘導体を含むジエンポリマーを主成分として含有するゴム組成物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5811479A (enExample) |
| EP (1) | EP0786493B1 (enExample) |
| JP (1) | JP3623332B2 (enExample) |
| KR (1) | KR100462096B1 (enExample) |
| CN (1) | CN1113927C (enExample) |
| AT (1) | ATE201036T1 (enExample) |
| AU (1) | AU724825B2 (enExample) |
| BR (1) | BR9700774A (enExample) |
| CA (1) | CA2195990C (enExample) |
| DE (1) | DE69704724T2 (enExample) |
| ES (1) | ES2156621T3 (enExample) |
| FR (1) | FR2744127A1 (enExample) |
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|---|---|---|---|---|
| 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 |
| US6020430A (en) * | 1998-05-20 | 2000-02-01 | Fmc Corporation | Functionalized diene and alkenylsubstituted aromatic silicone copolymers and processes for making the same |
| US6344521B1 (en) | 1998-05-20 | 2002-02-05 | Fmc Corporation | Protected functionalized diene and alkenyl substituted aromatic silicone triblock copolymers and processes for making the same |
| EP1153942B1 (en) * | 1998-09-02 | 2006-11-08 | Kaneka Corporation | Polymer, processes for producing polymer, and composition |
| JP4015327B2 (ja) * | 1998-09-02 | 2007-11-28 | 株式会社カネカ | 重合体、重合体の製造方法及び組成物 |
| KR100312176B1 (ko) * | 1999-03-23 | 2001-11-14 | 김충섭 | 알콕시 실란으로 치환된 디엔 공중합체 및 유기·무기 하이브리드 조성물 |
| US6255404B1 (en) * | 1999-07-26 | 2001-07-03 | Bridgestone Corporation | Method to control increase in viscosity during aging of siloxane modified polymers |
| US6279632B1 (en) * | 1999-11-24 | 2001-08-28 | Bridgestone Corporation | Method to control increase in viscosity during aging of siloxane modified polymers |
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| WO2001075738A1 (en) * | 2000-03-31 | 2001-10-11 | Front End Capital, Llc | Method of raising capital for early stage companies through broker-dealer |
| US6524716B2 (en) | 2000-07-27 | 2003-02-25 | The Goodyear Tire & Rubber Company | Method for the preparation of a diene polymer interpenetrated with a polysiloxane |
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| DE10038488A1 (de) * | 2000-08-08 | 2002-02-21 | Bayer Ag | Isocyanatosilan- und mikrogelhaltige Kautschukmischungen |
| JP2002161139A (ja) * | 2000-11-24 | 2002-06-04 | Bridgestone Corp | ブロック共重合体及びその製造方法、並びに、ゴム組成物 |
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| WO2003002648A1 (fr) | 2001-06-28 | 2003-01-09 | Societe De Technologie Michelin | Bande de roulement pour pneumatique renforcee d'une silice a basse surface specifique |
| CN1325549C (zh) | 2001-06-28 | 2007-07-11 | 米其林技术公司 | 采用具有非常低比表面积的二氧化硅增强的轮胎胎面 |
| JP2003155383A (ja) * | 2001-11-21 | 2003-05-27 | Toyo Tire & Rubber Co Ltd | タイヤトレッド用ゴム組成物 |
| JP5016924B2 (ja) | 2003-06-09 | 2012-09-05 | 株式会社ブリヂストン | 逐次的に停止させたポリマーを含む改良されたヒステリシスを有するエラストマー組成物 |
| CN102816359B (zh) * | 2004-04-27 | 2016-06-22 | 株式会社普利司通 | 生产具有改进的氧化硅增强的轮胎组合物的方法 |
| CN101445568B (zh) * | 2004-10-26 | 2014-11-19 | 株式会社普利司通 | 具有连接基团的官能化聚合物 |
| US7836928B2 (en) * | 2004-10-26 | 2010-11-23 | Bridgestone Corporation | Method of producing a tire composition having improved silica reinforcement |
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| WO2006076629A1 (en) * | 2005-01-14 | 2006-07-20 | Bridgestone Corporation | Functionalized polymers and improved tires therefrom |
| ES2334702T3 (es) * | 2005-01-14 | 2010-03-15 | Bridgestone Corporation | Procedimiento de preparacion de un neumatico con esfuerzo de silice mejorado. |
| DE102005006870A1 (de) * | 2005-02-14 | 2006-08-24 | Byk-Chemie Gmbh | Oberflächenmodifizierte Nanopartikel, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP2004744B1 (en) * | 2006-04-13 | 2017-12-06 | Bridgestone Corporation | Composition including multiple functionalized polymers |
| US7858690B2 (en) * | 2006-10-06 | 2010-12-28 | Bridgestone Corporation | Functional coupling agents and polymers prepared therewith |
| JP4559403B2 (ja) * | 2006-12-06 | 2010-10-06 | 宇部興産株式会社 | 変性ジエン系ゴムの製造法 |
| JP4731453B2 (ja) * | 2006-12-06 | 2011-07-27 | 宇部興産株式会社 | ゴム加硫物 |
| DE102007031986A1 (de) | 2007-07-10 | 2009-01-15 | Continental Aktiengesellschaft | Kautschukmischung, insbesondere für Reifen |
| FR2930554B1 (fr) * | 2008-04-29 | 2012-08-17 | Michelin Soc Tech | Melange elastomerique comprenant majoritairement un elastomere dienique couple par un groupe amino-alcoxysilane, composition de caoutchouc le comprenant et leurs procedes d'obtention. |
| SG159473A1 (en) | 2008-08-27 | 2010-03-30 | Sumitomo Chemical Co | Conjugated diene polymer, conjugated diene polymer composition, and method for producing conjugated diene polymer |
| SG159479A1 (en) * | 2008-08-27 | 2010-03-30 | Sumitomo Chemical Co | Conjugated diene polymer, conjugated diene polymer composition, and method for producing conjugated diene polymer |
| US8071689B2 (en) * | 2008-09-10 | 2011-12-06 | The Goodyear Tire & Rubber Company | Methods of making siloxy-amine functionalized rubbery polymers and uses thereof in rubber compositions for tires |
| CN101724185B (zh) * | 2008-10-16 | 2013-10-23 | 住友橡胶工业株式会社 | 橡胶组合物及轮胎 |
| US8022159B2 (en) | 2008-11-24 | 2011-09-20 | The Goodyear Tire & Rubber Company | Terminating compounds, polymers, and their uses in rubber compositions and tires |
| FR2940294B1 (fr) | 2008-12-23 | 2011-02-18 | Michelin Soc Tech | Nouveau systeme d'amorcage pour polymerisation anionique de dienes conjugues, procede de preparation d'elastomeres dieniques. |
| JP5663146B2 (ja) * | 2009-05-29 | 2015-02-04 | 株式会社ブリヂストン | 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、ゴム組成物、空気入りタイヤ |
| FR2951178B1 (fr) | 2009-10-08 | 2012-08-17 | Michelin Soc Tech | Elastomere dienique fonctionnalise et composition de caoutchouc le contenant. |
| FR2951186B1 (fr) * | 2009-10-12 | 2012-01-06 | Michelin Soc Tech | Composition de caoutchouc a base de glycerol et d'un elastomere fonctionnalise et bande de roulement pour pneumatique |
| FR2954774B1 (fr) | 2009-10-30 | 2012-01-06 | Michelin Soc Tech | Methode de preparation d'un melange maitre de caoutchouc naturel et de silice |
| FR2954775B1 (fr) | 2009-10-30 | 2012-03-30 | Michelin Soc Tech | Methode de preparation d'un melange maitre d'elastomere dienique synthetique et de silice |
| FR2952064B1 (fr) | 2009-10-30 | 2012-08-31 | Michelin Soc Tech | Methode de preparation d'un melange maitre d'elastomere dienique et de silice |
| CN102869715B (zh) * | 2010-06-25 | 2015-04-22 | 米其林集团总公司 | 用于汽车和轻型卡车的低滚动阻力胎面 |
| US9221923B2 (en) | 2010-12-31 | 2015-12-29 | Bridgestone Corporation | Coupled polymers and methods for making same |
| FR2974093B1 (fr) | 2011-04-15 | 2015-05-08 | Michelin Soc Tech | Procede de preparation d'un melange maitre d'elastomere et d'une charge inorganique renforcante |
| US8680210B2 (en) | 2011-05-02 | 2014-03-25 | Bridgestone Corporation | Method for making functionalized polymer |
| KR101247392B1 (ko) | 2011-05-19 | 2013-03-25 | 금호타이어 주식회사 | 승용차 타이어용 트레드 고무 조성물 |
| US8580886B2 (en) | 2011-09-20 | 2013-11-12 | Dow Corning Corporation | Method for the preparation and use of bis (alkoxysilylorgano)-dicarboxylates |
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| FR2981079B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode pour preparer un melange maitre d'elastomere dienique et de silice |
| FR2981080B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode de preparation d'un melange maitre de caoutchouc naturel et de silice dopee magnesium |
| FR2981081B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode de preparation d'un melange maitre de caoutchouc naturel et de silice |
| FR2981078B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode pour preparer un melange maitre d'elastomere dienique et de silice |
| FR2981076B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode pour preparer un melange maitre d'elastomere dienique et de silice |
| FR2981077B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode pour preparer un melange maitre d'elastomere dienique et de silice |
| EP2785726B1 (en) | 2011-12-02 | 2018-08-01 | Dow Silicones Corporation | Ester-functional silanes and the preparation and use thereof; and use of iminium compounds as phase transfer catalysts |
| KR101400732B1 (ko) * | 2012-04-16 | 2014-05-30 | 금호타이어 주식회사 | 회전저항 특성 및 내마모성이 향상된 타이어 고무조성물 |
| DE102013105193B4 (de) * | 2013-05-22 | 2024-10-17 | Continental Reifen Deutschland Gmbh | Kautschukmischung und Verwendung derselben in Fahrzeugreifen |
| US9758639B2 (en) | 2014-04-30 | 2017-09-12 | Bridgestone Corporation | Rubber composition with imidazole-based silica shielding agent |
| FR3021971B1 (fr) * | 2014-06-05 | 2016-06-03 | Michelin & Cie | Pneumatique a faible resistance au roulement |
| US9951208B2 (en) | 2014-11-06 | 2018-04-24 | Bridgestone Corporation | Silica shielding agents and related methods |
| CN112625246B (zh) | 2014-12-30 | 2023-01-10 | 株式会社普利司通 | 末端官能化聚合物及相关方法 |
| WO2016180649A1 (de) * | 2015-05-13 | 2016-11-17 | Evonik Degussa Gmbh | Verbesserung des rollwiderstands von dienkautschukreifen durch silanmodifizierte polybutadiene |
| FR3038320A1 (fr) | 2015-07-02 | 2017-01-06 | Michelin & Cie | Composition de caoutchouc comprenant une silice de tres haute surface specifique et une resine hydrocarbonee de faible temperature de transition vitreuse |
| WO2017015592A1 (en) * | 2015-07-22 | 2017-01-26 | Bridgestone Corporation | Silane-functionalized polymer and process for making and using same |
| FR3042194A1 (fr) * | 2015-10-08 | 2017-04-14 | Michelin & Cie | Composition de caoutchouc contenant un elastomere dienique possedant une fonction en milieu de chaine |
| CN109937147B (zh) * | 2016-10-31 | 2021-04-20 | 米其林集团总公司 | 包括胎面的轮胎 |
| FR3065960B1 (fr) | 2017-05-05 | 2019-06-28 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant au moins une silice en tant que charge renforcante inorganique |
| DE102017221232A1 (de) * | 2017-11-28 | 2019-05-29 | Continental Reifen Deutschland Gmbh | Schwefelvernetzbare Kautschukmischung, Vulkanisat der Kautschukmischung und Fahrzeugreifen |
| FR3079842B1 (fr) | 2018-04-06 | 2020-10-09 | Michelin & Cie | Pneumatique comportant une composition de caoutchouc comprenant un nouvel agent de couplage polysulfure porteur de groupes associatifs azotes |
| FR3079841B1 (fr) | 2018-04-06 | 2020-10-09 | Michelin & Cie | Pneumatique comportant une composition de caoutchouc comprenant un nouvel agent de couplage polysulfure porteur de groupes associatifs azotes |
| CN109206694B (zh) * | 2018-09-11 | 2021-02-26 | 赛轮集团股份有限公司 | 一种轮胎胎面胶 |
| FR3087443B3 (fr) * | 2018-10-23 | 2020-10-23 | Michelin & Cie | Composition de caoutchouc |
| FR3113905B1 (fr) | 2020-09-04 | 2022-08-05 | Michelin & Cie | Composition de caoutchouc a base d’elastomere dienique fortement sature |
| FR3113906B1 (fr) | 2020-09-04 | 2022-08-05 | Michelin & Cie | Composition de caoutchouc a base d’elastomere dienique fortement sature |
| DE102020215725A1 (de) * | 2020-12-11 | 2022-06-15 | Continental Reifen Deutschland Gmbh | Kautschukmischung und Fahrzeugluftreifen |
| DE102020215722A1 (de) * | 2020-12-11 | 2022-06-15 | Continental Reifen Deutschland Gmbh | Kautschukmischung und Fahrzeugluftreifen |
| DE102020215719A1 (de) * | 2020-12-11 | 2022-06-15 | Continental Reifen Deutschland Gmbh | Kautschukmischung und Fahrzeugluftreifen |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051684A (en) | 1959-03-26 | 1962-08-28 | Directors Of The University Of | Organosiloxane polymers containing polydiene blocks |
| US3393182A (en) | 1965-02-23 | 1968-07-16 | Phillips Petroleum Co | Prevention of cold flow in polymers of conjugated dienes |
| US3483270A (en) | 1966-04-11 | 1969-12-09 | Gen Electric | Stereospecific organosiloxane-macromolecular hydrocarbon block copolymers |
| US3956232A (en) | 1972-11-20 | 1976-05-11 | Phillips Petroleum Company | Preparation of organometal terminated polymers |
| FR2273822A1 (fr) | 1974-06-05 | 1976-01-02 | Michelin & Cie | Polymeres ou copolymeres a composition sterique modifiee, obtenus par mise en oeuvre d'une nouvelle composition catalytique |
| FR2340958A2 (fr) | 1974-06-05 | 1977-09-09 | Michelin & Cie | Procede de polymerisation ou de copolymerisation de dienes conjugues et polymeres ainsi obtenus |
| US4026865A (en) | 1974-07-01 | 1977-05-31 | Phillips Petroleum Company | Preparation of organometal terminated polymers |
| FR2302311A1 (fr) | 1975-02-27 | 1976-09-24 | Michelin & Cie | Procede de preparation de polymeres de dienes |
| FR2338953A2 (fr) | 1976-01-21 | 1977-08-19 | Michelin & Cie | Procede de preparation de polymeres de dienes conjugues ou de copolymeres de dienes conjugues soit entre eux, soit avec un compose vinylaromatique |
| JPS58189203A (ja) | 1982-04-30 | 1983-11-04 | Nippon Zeon Co Ltd | ゴム組成物 |
| FR2562534B1 (fr) | 1984-04-06 | 1986-06-27 | Rhone Poulenc Chim Base | Nouvelle silice precipitee a caracteres morphologiques ameliores, procede pour son obtention et application, notamment comme charge |
| JPH078956B2 (ja) * | 1984-11-26 | 1995-02-01 | 鐘淵化学工業株式会社 | 硬化性組成物 |
| US4618650A (en) * | 1985-09-04 | 1986-10-21 | The Goodyear Tire & Rubber Company | Siloxane containing network polymer |
| US4783504A (en) * | 1986-02-28 | 1988-11-08 | Shell Oil Company | Hot melt adhesive containing a silane grafted hydrogenated block polymer |
| EP0299074B1 (en) | 1987-01-14 | 1992-01-29 | Bridgestone Corporation | Tire |
| JPH068366B2 (ja) | 1987-04-23 | 1994-02-02 | 株式会社ブリヂストン | タイヤ用ゴム組成物 |
| JP2652795B2 (ja) | 1988-03-31 | 1997-09-10 | 日本ゼオン株式会社 | ジエン系重合体ゴムの製造方法及びゴム組成物 |
| ES2085959T5 (es) * | 1990-03-02 | 2001-02-01 | Bridgestone Corp | Neumaticos. |
| DE4023537A1 (de) | 1990-07-25 | 1992-01-30 | Degussa | Mit organosiliciumverbindungen chemisch modifizierte russe, verfahren zu deren herstellung und deren verwendung |
| FR2673187B1 (fr) | 1991-02-25 | 1994-07-01 | Michelin & Cie | Composition de caoutchouc et enveloppes de pneumatiques a base de ladite composition. |
| DE4119959A1 (de) | 1991-06-18 | 1992-12-24 | Degussa | Verfahren zur herstellung von vulkanisierbaren, mit russ gefuellten kunststoff- und kautschukmischungen |
| FR2678259B1 (fr) | 1991-06-26 | 1993-11-05 | Rhone Poulenc Chimie | Nouvelles silices precipitees sous forme de granules ou de poudres, procedes de synthese et utilisation au renforcement des elastomeres. |
-
1996
- 1996-01-26 FR FR9601040A patent/FR2744127A1/fr active Pending
-
1997
- 1997-01-15 DE DE69704724T patent/DE69704724T2/de not_active Expired - Lifetime
- 1997-01-15 EP EP97100508A patent/EP0786493B1/fr not_active Expired - Lifetime
- 1997-01-15 AT AT97100508T patent/ATE201036T1/de not_active IP Right Cessation
- 1997-01-15 ES ES97100508T patent/ES2156621T3/es not_active Expired - Lifetime
- 1997-01-23 US US08/787,777 patent/US5811479A/en not_active Expired - Lifetime
- 1997-01-24 CA CA002195990A patent/CA2195990C/fr not_active Expired - Fee Related
- 1997-01-24 KR KR1019970001978A patent/KR100462096B1/ko not_active Expired - Fee Related
- 1997-01-24 AU AU12333/97A patent/AU724825B2/en not_active Ceased
- 1997-01-24 BR BR9700774A patent/BR9700774A/pt not_active IP Right Cessation
- 1997-01-27 JP JP01261797A patent/JP3623332B2/ja not_active Expired - Fee Related
- 1997-01-27 CN CN97100458A patent/CN1113927C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE201036T1 (de) | 2001-05-15 |
| KR970059218A (ko) | 1997-08-12 |
| EP0786493A1 (fr) | 1997-07-30 |
| ES2156621T3 (es) | 2001-07-01 |
| EP0786493B1 (fr) | 2001-05-09 |
| AU1233397A (en) | 1997-07-31 |
| CA2195990C (fr) | 2006-08-29 |
| US5811479A (en) | 1998-09-22 |
| DE69704724D1 (de) | 2001-06-13 |
| MX9700588A (es) | 1998-06-30 |
| AU724825B2 (en) | 2000-09-28 |
| CA2195990A1 (fr) | 1997-07-27 |
| DE69704724T2 (de) | 2001-11-29 |
| CN1113927C (zh) | 2003-07-09 |
| BR9700774A (pt) | 1998-10-06 |
| JPH09208749A (ja) | 1997-08-12 |
| KR100462096B1 (ko) | 2005-04-19 |
| CN1162607A (zh) | 1997-10-22 |
| FR2744127A1 (fr) | 1997-08-01 |
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