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)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Tires In General (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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP0877047B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4394181B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1202164C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE225380T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU733790B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR9801587A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2235095A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69808367T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2184166T3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2763074B1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO1998050462A1 (cg-RX-API-DMAC7.html) |
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. |
| EP1290083A1 (fr) | 2000-05-22 | 2003-03-12 | Société de Technologie Michelin | Composition pour bande de roulement de pneumatique et son procede de preparation |
| BR0106664A (pt) | 2000-05-26 | 2002-04-02 | Michelin Soc Tech | Composição de borracha reticulável ou reticulada que pode ser utilizada para constituir uma banda de rodagem de pneumático, processo de preparação de uma composição de borracha reticulável, e, banda de rodagem de pneumático |
| 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 |
| JP2005510610A (ja) | 2001-11-26 | 2005-04-21 | ソシエテ ド テクノロジー ミシュラン | タイヤトレッド用ゴム組成物及びその製造方法 |
| 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 |
| 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 |
| 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 |
| 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 |
| CN1878830B (zh) | 2003-09-01 | 2012-07-04 | 日本瑞翁株式会社 | 共轭二烯类橡胶组合物、其制造方法及橡胶交联物 |
| 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 |
| US8063153B2 (en) * | 2004-10-26 | 2011-11-22 | Bridgestone Corporation | Functionalized polymer with linking group |
| 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 |
| 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 |
| WO2009113546A1 (ja) * | 2008-03-10 | 2009-09-17 | 株式会社ブリヂストン | 変性共役ジエン（共）重合体の製造方法、変性共役ジエン（共）重合体、並びにそれを用いたゴム組成物及びタイヤ |
| 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 |
| HUE047720T2 (hu) * | 2009-08-27 | 2020-05-28 | Birla Carbon U S A Inc | Felületkezelt kormok alkalmazása egy elasztomerben, keverék hiszterézis és abroncs gördülési ellenállás csökkentésére és nedves tapadás javítására |
| 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 |
| CN103370377B (zh) * | 2010-12-14 | 2019-01-15 | 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 |
| BR112013016430B1 (pt) | 2010-12-31 | 2020-12-01 | Bridgestone Corporation | polímeros acoplados e métodos para produzir os mesmos |
| 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 |
| US9518072B2 (en) | 2011-12-02 | 2016-12-13 | Dow Corning Corporation | Ester-functional silanes and the preparation and use thereof; and use of iminium compounds as phase transfer catalysts |
| 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 |
| 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 |
| JP6173556B2 (ja) | 2013-03-13 | 2017-08-02 | キャボット コーポレイションＣａｂｏｔ Ｃｏｒｐｏｒａｔｉｏｎ | 組み合わされた低誘電率、高抵抗率及び光学濃度特性、ならびに、制御された電気抵抗率を有するフィラー−ポリマー組成物を含むコーティング、それから製造されるデバイス及びその製造方法 |
| EP2796471A1 (de) * | 2013-04-24 | 2014-10-29 | LANXESS Deutschland GmbH | Silanhaltige carboxyterminierte Polymere |
| WO2015065884A1 (en) | 2013-10-31 | 2015-05-07 | 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 |
| CN107709472B (zh) | 2015-04-30 | 2021-05-18 | 卡博特公司 | 包覆有碳的颗粒 |
| 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 |
| WO2019017067A1 (ja) | 2017-07-19 | 2019-01-24 | 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 |
| WO2019122605A1 (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 |
| 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 |
| 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 |
| EP3728451B1 (fr) | 2017-12-19 | 2022-02-02 | Compagnie Generale Des Etablissements Michelin | Bande de roulement de pneumatique dont le système de réticulation est à 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 |
|---|---|---|---|---|
| WO1988005448A1 (fr) * | 1987-01-14 | 1988-07-28 | Bridgestone Corporation | Pneu |
| DE69119125T3 (de) * | 1990-03-02 | 2001-01-11 | Bridgestone Corp., Tokio/Tokyo | Luftreifen |
| 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 AT AT98107525T patent/ATE225380T1/de not_active IP Right Cessation
- 1998-04-24 DE DE69808367T patent/DE69808367T2/de not_active Expired - Lifetime
- 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 BR BR9801587A patent/BR9801587A/pt not_active IP Right Cessation
- 1998-05-06 CA CA002235095A patent/CA2235095A1/fr not_active Abandoned
- 1998-05-06 AU AU64770/98A patent/AU733790B2/en not_active Ceased
- 1998-05-06 US US09/073,551 patent/US6071995A/en not_active Expired - Lifetime
- 1998-05-07 JP JP12450998A patent/JP4394181B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10316800A (ja) | 1998-12-02 |
| AU6477098A (en) | 1998-11-12 |
| CN1202164C (zh) | 2005-05-18 |
| ATE225380T1 (de) | 2002-10-15 |
| JP4394181B2 (ja) | 2010-01-06 |
| FR2763074B1 (fr) | 1999-06-25 |
| ES2184166T3 (es) | 2003-04-01 |
| EP0877047A1 (fr) | 1998-11-11 |
| CN1226908A (zh) | 1999-08-25 |
| DE69808367D1 (de) | 2002-11-07 |
| CA2235095A1 (fr) | 1998-11-07 |
| AU733790B2 (en) | 2001-05-24 |
| EP0877047B1 (fr) | 2002-10-02 |
| US6071995A (en) | 2000-06-06 |
| BR9801587A (pt) | 1999-07-06 |
| FR2763074A1 (fr) | 1998-11-13 |
| WO1998050462A1 (fr) | 1998-11-12 |
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