DE69808367T2 - Kautschukzusammensetzung enthaltend Russ mit auf seiner Oberfläche fixiertes Siliciumdioxid und ein mit Silanol-Gruppe funktionalisertes oder modifiziertes Dienpolymer - Google Patents
Kautschukzusammensetzung enthaltend Russ mit auf seiner Oberfläche fixiertes Siliciumdioxid und ein mit Silanol-Gruppe funktionalisertes oder modifiziertes DienpolymerInfo
- Publication number
- DE69808367T2 DE69808367T2 DE69808367T DE69808367T DE69808367T2 DE 69808367 T2 DE69808367 T2 DE 69808367T2 DE 69808367 T DE69808367 T DE 69808367T DE 69808367 T DE69808367 T DE 69808367T DE 69808367 T2 DE69808367 T2 DE 69808367T2
- Authority
- DE
- Germany
- Prior art keywords
- diene polymer
- carbon black
- silanol group
- functionalized
- silanol
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 110
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 107
- 229920000642 polymer Polymers 0.000 title claims abstract description 92
- 239000006229 carbon black Substances 0.000 title claims abstract description 52
- 239000000377 silicon dioxide Substances 0.000 title claims abstract description 52
- 125000005372 silanol group Chemical group 0.000 title claims abstract description 39
- 229920001971 elastomer Polymers 0.000 title claims abstract description 31
- 239000005060 rubber Substances 0.000 title claims abstract description 21
- 241000872198 Serjania polyphylla Species 0.000 title claims abstract description 11
- 150000001993 dienes Chemical class 0.000 title claims description 39
- -1 polysiloxane Polymers 0.000 claims abstract description 32
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 25
- 229920001577 copolymer Polymers 0.000 claims description 25
- 239000012763 reinforcing filler Substances 0.000 claims description 18
- 235000012239 silicon dioxide Nutrition 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002897 diene group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 244000043261 Hevea brasiliensis Species 0.000 claims description 3
- 229920003052 natural elastomer Polymers 0.000 claims description 3
- 229920001194 natural rubber Polymers 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000004636 vulcanized rubber Substances 0.000 claims 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000945 filler Substances 0.000 abstract description 6
- 235000019241 carbon black Nutrition 0.000 description 44
- 239000003795 chemical substances by application Substances 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- 239000000806 elastomer Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000007306 functionalization reaction Methods 0.000 description 7
- 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 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- VZEZONWRBFJJMZ-UHFFFAOYSA-N 3-allyl-2-[2-(diethylamino)ethoxy]benzaldehyde Chemical compound CCN(CC)CCOC1=C(CC=C)C=CC=C1C=O VZEZONWRBFJJMZ-UHFFFAOYSA-N 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- 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 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 239000010692 aromatic oil Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 239000011787 zinc oxide Substances 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
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 229910000077 silane Inorganic materials 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
- 238000005160 1H NMR spectroscopy Methods 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 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
- 239000000470 constituent Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000002542 deteriorative effect Effects 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
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical group [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 230000000930 thermomechanical effect Effects 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
- 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
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-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
- 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
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-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 class COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- PJXJBPMWCKMWLS-UHFFFAOYSA-N 2-methyl-3-methylidenepent-1-ene Chemical compound CCC(=C)C(C)=C PJXJBPMWCKMWLS-UHFFFAOYSA-N 0.000 description 1
- UMROOINDDALMLN-UHFFFAOYSA-N 3,3-dichloroprop-2-enylsilane Chemical compound ClC(=CC[SiH3])Cl UMROOINDDALMLN-UHFFFAOYSA-N 0.000 description 1
- OAOZZYBUAWEDRA-UHFFFAOYSA-N 3,4-dimethylidenehexane Chemical compound CCC(=C)C(=C)CC OAOZZYBUAWEDRA-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 241001441571 Hiodontidae Species 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
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- GAZZTULIUXRAAI-UHFFFAOYSA-N [2,3-bis(diethylamino)phenyl]-phenylmethanone Chemical compound CCN(CC)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N(CC)CC GAZZTULIUXRAAI-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- XRBZWUQAUXLFDY-UHFFFAOYSA-N benzyl(dichloro)silane Chemical compound Cl[SiH](Cl)CC1=CC=CC=C1 XRBZWUQAUXLFDY-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 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
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 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
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 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
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-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
- 239000003921 oil Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 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
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 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
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002604 ultrasonography Methods 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
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/02—Ingredients treated with inorganic substances
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
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)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9705887A FR2763074B1 (fr) | 1997-05-07 | 1997-05-07 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69808367D1 DE69808367D1 (de) | 2002-11-07 |
| DE69808367T2 true DE69808367T2 (de) | 2003-06-12 |
Family
ID=9506858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69808367T Expired - Lifetime DE69808367T2 (de) | 1997-05-07 | 1998-04-24 | Kautschukzusammensetzung enthaltend Russ mit auf seiner Oberfläche fixiertes Siliciumdioxid und ein mit Silanol-Gruppe funktionalisertes oder modifiziertes Dienpolymer |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6071995A (enExample) |
| EP (1) | EP0877047B1 (enExample) |
| JP (1) | JP4394181B2 (enExample) |
| CN (1) | CN1202164C (enExample) |
| AT (1) | ATE225380T1 (enExample) |
| AU (1) | AU733790B2 (enExample) |
| BR (1) | BR9801587A (enExample) |
| CA (1) | CA2235095A1 (enExample) |
| DE (1) | DE69808367T2 (enExample) |
| ES (1) | ES2184166T3 (enExample) |
| FR (1) | FR2763074B1 (enExample) |
| WO (1) | WO1998050462A1 (enExample) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4105328B2 (ja) * | 1999-04-09 | 2008-06-25 | 住友ゴム工業株式会社 | 空気入りタイヤ |
| US6255404B1 (en) * | 1999-07-26 | 2001-07-03 | Bridgestone Corporation | Method to control increase in viscosity during aging of siloxane modified polymers |
| 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 |
| FR2804688B1 (fr) * | 2000-02-07 | 2006-08-11 | Michelin Soc Tech | Utilisation d'une composition de caoutchouc pour retarder lors du roulage l'apparition de l'usure irreguliere sur une bande de roulement de pneumatique destinee a porter de lourdes charges |
| DE60109224T2 (de) | 2000-02-24 | 2006-01-19 | Société de Technologie Michelin | Vulkanisierbare Kautschukmischung zur Herstellung eines Luftreifens und Luft- reifens und Luftreifen, der eine solche Zusammensetzung enthält. |
| CN101307162B (zh) | 2000-05-22 | 2014-03-19 | 米其林集团总公司 | 轮胎行驶胎面的组合物以及它的制造方法 |
| CN1140570C (zh) | 2000-05-26 | 2004-03-03 | 米其林技术公司 | 可用作轮胎胎面的橡胶组合物 |
| KR100403089B1 (ko) * | 2001-01-03 | 2003-10-30 | 금호석유화학 주식회사 | 말단변성 디엔계 공중합체의 제조방법 |
| US6569942B2 (en) * | 2001-03-14 | 2003-05-27 | The Goodyear Tire & Rubber Company | Rubber compositions containing silicon coupled oligomers |
| AU2002356721A1 (en) | 2001-11-26 | 2003-06-10 | Societe De Technologie Michelin | Rubber composition for running tread and method for obtaining same |
| US20040095244A1 (en) * | 2002-05-10 | 2004-05-20 | Kevin Conwell | Tire identification label and tire label film with integrated barrier |
| WO2003102053A1 (en) | 2002-05-31 | 2003-12-11 | Zeon Corporation | Conjugated diene rubber, process for producing the same, and rubber composition |
| KR100466200B1 (ko) * | 2002-09-02 | 2005-01-13 | 금호석유화학 주식회사 | 다가성 커플링제로 처리된 말단변성 스티렌-디엔블록공중합체 |
| US6998448B2 (en) * | 2002-09-16 | 2006-02-14 | The Goodyear Tire & Rubber Company | Tire with tread of CIS 1,4-polybutadiene rich rubber composition which contains a functional styrene/butadiene elastomer, silica and coupling agent |
| US7071251B2 (en) * | 2002-09-17 | 2006-07-04 | The Goodyear Tire & Rubber Company | Tire with component comprised of rubber composite of styrene/butadiene elastomer containing pendent silanol and/or siloxy groups |
| US7163975B2 (en) * | 2002-09-17 | 2007-01-16 | The Goodyear Tire & Rubber Company | Tire with compound of rubber composition comprised of silanol and/or siloxy functionalized elastomer and silica |
| US7137423B2 (en) * | 2003-06-06 | 2006-11-21 | The Goodyear Tire & Rubber Company | Tire with component comprised of amine functionalized styrene/diene copolymer elastomer, silanol functionalized carbon black and coupling agent |
| US7700693B2 (en) * | 2003-09-01 | 2010-04-20 | Zeon Corporation | Conjugated diene rubber compostion, process for producing the same and rubber vulcanizate |
| US20050171267A1 (en) * | 2004-01-29 | 2005-08-04 | Zanzig David J. | Tire with component of rubber composition comprised of functionalized styrene/butadiene elastomer, silica and styrene/alpha methylstyrene resin |
| US7338914B2 (en) | 2004-03-31 | 2008-03-04 | Intermec Ip Corp. | RFID tire label |
| 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 |
| 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 |
| CN102026826B (zh) * | 2008-03-10 | 2015-01-14 | 株式会社普利司通 | 改性共轭二烯(共)聚合物的制造方法、改性共轭二烯(共)聚合物以及使用其的橡胶组合物和轮胎 |
| JP5473360B2 (ja) * | 2008-03-10 | 2014-04-16 | 株式会社ブリヂストン | ゴム組成物及びそれを用いたタイヤ |
| DE102009023915A1 (de) * | 2009-05-27 | 2010-12-02 | Rhein-Chemie Rheinau Gmbh | Mischungen aus funktionalisierten Dienkautschuken mit Trimethylolpropan und Fettsäure, ein Verfahren zu deren Herstellung und deren Verwendung |
| 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 |
| IN2012DN02519A (enExample) * | 2009-08-27 | 2015-08-28 | Columbian Chem | |
| FR2951178B1 (fr) | 2009-10-08 | 2012-08-17 | Michelin Soc Tech | Elastomere dienique fonctionnalise et composition de caoutchouc le contenant. |
| FR2968006B1 (fr) | 2010-11-26 | 2012-12-21 | Michelin Soc Tech | Bande de roulement de pneumatique |
| FR2968005B1 (fr) | 2010-11-26 | 2012-12-21 | Michelin Soc Tech | Bande de roulement de pneumatique neige |
| FR2968600A1 (fr) | 2010-12-08 | 2012-06-15 | Michelin Soc Tech | Bande de roulement pour pneumatique neige |
| CN109251505A (zh) | 2010-12-14 | 2019-01-22 | 卡博特公司 | 控制填料-聚合物组合物中的电阻率的方法以及与其相关的产品 |
| JP5934251B2 (ja) | 2010-12-31 | 2016-06-15 | 株式会社ブリヂストン | カップリングされたポリマーおよびそれを製造する方法 |
| US8680210B2 (en) | 2011-05-02 | 2014-03-25 | Bridgestone Corporation | Method for making functionalized polymer |
| US8580886B2 (en) | 2011-09-20 | 2013-11-12 | Dow Corning Corporation | Method for the preparation and use of bis (alkoxysilylorgano)-dicarboxylates |
| 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 |
| JP5996961B2 (ja) * | 2012-08-03 | 2016-09-21 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
| WO2014021002A1 (ja) * | 2012-08-03 | 2014-02-06 | 住友ゴム工業株式会社 | トレッド用ゴム組成物及び空気入りタイヤ |
| CN105209558A (zh) | 2013-03-13 | 2015-12-30 | 卡博特公司 | 具有拥有组合的低介电常数、高电阻率、和光学密度性质及受控电阻率的填料-聚合物组合物的涂层、用它制成的器件、及其制造方法 |
| EP2796471A1 (de) | 2013-04-24 | 2014-10-29 | LANXESS Deutschland GmbH | Silanhaltige carboxyterminierte Polymere |
| US10207540B2 (en) | 2013-10-31 | 2019-02-19 | Compagnie Generale Des Etablissements Michelin | Functionalized polymer blends for improved wear |
| FR3021971B1 (fr) | 2014-06-05 | 2016-06-03 | Michelin & Cie | Pneumatique a faible resistance au roulement |
| FR3021972B1 (fr) | 2014-06-05 | 2016-06-03 | Michelin & Cie | Pneumatique a faible resistance au roulement |
| FR3023293B1 (fr) * | 2014-07-03 | 2016-07-01 | Michelin & Cie | Elastomere dienique a ip reduit possedant une fonction silanol en extremite de chaine et composition le contenant |
| WO2016109476A1 (en) | 2014-12-30 | 2016-07-07 | Compagnie Generale Des Etablissements Michelin | Rubber composition with resins |
| JP2018522996A (ja) | 2015-04-30 | 2018-08-16 | キャボット コーポレイションＣａｂｏｔ Ｃｏｒｐｏｒａｔｉｏｎ | 炭素コーティング粒子 |
| FR3036115B1 (fr) | 2015-05-11 | 2017-05-19 | Michelin & Cie | Composition de caoutchouc |
| FR3061187B1 (fr) | 2016-12-22 | 2019-02-01 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc avec une bonne dispersion de quantites elevees de charge inorganique renforcante |
| CN108250327B (zh) * | 2016-12-28 | 2020-04-14 | 北京化工大学 | 一种链端含硅和羟基的官能化聚合物及其制备方法和支化聚合物 |
| US11458768B2 (en) | 2017-07-19 | 2022-10-04 | Sumitomo Rubber Industries, Ltd. | Rubber composition for tread, and pneumatic tire |
| WO2019122602A1 (fr) | 2017-12-19 | 2019-06-27 | Compagnie Generale Des Etablissements Michelin | Bande de roulement de pneumatique dont le systeme de reticulation est a base de peroxyde organique |
| US20210087370A1 (en) | 2017-12-19 | 2021-03-25 | Compagnie Generale Des Etablissements Michelin | Tire tread, the crosslinking system of which is based on organic peroxide |
| US20210079200A1 (en) | 2017-12-19 | 2021-03-18 | Compagnie Generale Des Etablissements Michelin | Tire tread, the crosslinking system of which is based on organic peroxide |
| WO2019122604A1 (fr) | 2017-12-19 | 2019-06-27 | Compagnie Generale Des Etablissements Michelin | Bande de roulement de pneumatique dont le systeme de reticulation est a base de peroxyde organique |
| FR3081161B1 (fr) | 2018-05-17 | 2020-07-10 | Compagnie Generale Des Etablissements Michelin | Bande de roulement de pneumatique dont le systeme de reticulation est a base de peroxyde organique |
| FR3081162B1 (fr) | 2018-05-17 | 2020-04-24 | Compagnie Generale Des Etablissements Michelin | Bande de roulement de pneumatique dont le systeme de reticulation est a base de peroxyde organique |
| CN112094434B (zh) * | 2020-08-24 | 2022-05-27 | 杭州师范大学 | 一种含硅烷氧基硼硅氧烷改性白炭黑的制备方法及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0713158B2 (ja) * | 1987-01-14 | 1995-02-15 | 株式会社ブリヂストン | タイヤ |
| EP0447066B2 (en) * | 1990-03-02 | 2000-08-16 | Bridgestone Corporation | Pneumatic tyres |
| JP2788212B2 (ja) * | 1994-11-11 | 1998-08-20 | 横浜ゴム株式会社 | 表面処理カーボンブラック及びそれを用いたゴム組成物 |
-
1997
- 1997-05-07 FR FR9705887A patent/FR2763074B1/fr not_active Expired - Fee Related
-
1998
- 1998-04-24 EP EP98107525A patent/EP0877047B1/fr not_active Expired - Lifetime
- 1998-04-24 ES ES98107525T patent/ES2184166T3/es not_active Expired - Lifetime
- 1998-04-24 DE DE69808367T patent/DE69808367T2/de not_active Expired - Lifetime
- 1998-04-24 AT AT98107525T patent/ATE225380T1/de not_active IP Right Cessation
- 1998-05-05 WO PCT/EP1998/002652 patent/WO1998050462A1/fr not_active Ceased
- 1998-05-05 CN CNB988006103A patent/CN1202164C/zh not_active Expired - Fee Related
- 1998-05-06 US US09/073,551 patent/US6071995A/en not_active Expired - Lifetime
- 1998-05-06 AU AU64770/98A patent/AU733790B2/en not_active Ceased
- 1998-05-06 CA CA002235095A patent/CA2235095A1/fr not_active Abandoned
- 1998-05-06 BR BR9801587A patent/BR9801587A/pt not_active IP Right Cessation
- 1998-05-07 JP JP12450998A patent/JP4394181B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1226908A (zh) | 1999-08-25 |
| FR2763074B1 (fr) | 1999-06-25 |
| DE69808367D1 (de) | 2002-11-07 |
| EP0877047A1 (fr) | 1998-11-11 |
| AU733790B2 (en) | 2001-05-24 |
| JP4394181B2 (ja) | 2010-01-06 |
| EP0877047B1 (fr) | 2002-10-02 |
| JPH10316800A (ja) | 1998-12-02 |
| BR9801587A (pt) | 1999-07-06 |
| WO1998050462A1 (fr) | 1998-11-12 |
| FR2763074A1 (fr) | 1998-11-13 |
| CN1202164C (zh) | 2005-05-18 |
| CA2235095A1 (fr) | 1998-11-07 |
| US6071995A (en) | 2000-06-06 |
| ES2184166T3 (es) | 2003-04-01 |
| AU6477098A (en) | 1998-11-12 |
| ATE225380T1 (de) | 2002-10-15 |
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| 8364 | No opposition during term of opposition |