CA2296010A1 - Composition de caoutchouc dienique renforcee d'une charge blanche, comportant a titre d'agent de couplage (charge blanche/elastomere) un polyorganosiloxane multifonctionnalise - Google Patents
Composition de caoutchouc dienique renforcee d'une charge blanche, comportant a titre d'agent de couplage (charge blanche/elastomere) un polyorganosiloxane multifonctionnalise Download PDFInfo
- Publication number
- CA2296010A1 CA2296010A1 CA002296010A CA2296010A CA2296010A1 CA 2296010 A1 CA2296010 A1 CA 2296010A1 CA 002296010 A CA002296010 A CA 002296010A CA 2296010 A CA2296010 A CA 2296010A CA 2296010 A1 CA2296010 A1 CA 2296010A1
- Authority
- CA
- Canada
- Prior art keywords
- pos
- radical
- function
- elastomer
- white
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 144
- 229920001971 elastomer Polymers 0.000 title claims abstract description 71
- 239000000806 elastomer Substances 0.000 title claims abstract description 46
- 239000007822 coupling agent Substances 0.000 title claims abstract description 42
- 239000000945 filler Substances 0.000 title claims abstract description 36
- 229920003244 diene elastomer Polymers 0.000 title claims abstract description 33
- 239000005060 rubber Substances 0.000 claims abstract description 25
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 22
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 19
- 239000012763 reinforcing filler Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 230000006870 function Effects 0.000 claims description 93
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 66
- -1 i Chemical class 0.000 claims description 32
- 239000000377 silicon dioxide Substances 0.000 claims description 32
- 150000001993 dienes Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910018557 Si O Inorganic materials 0.000 claims description 21
- 229920001577 copolymer Polymers 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 20
- 239000002243 precursor Substances 0.000 claims description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 17
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000010703 silicon Substances 0.000 claims description 13
- 238000004073 vulcanization Methods 0.000 claims description 11
- 239000005062 Polybutadiene Substances 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 229920002857 polybutadiene Polymers 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 238000005987 sulfurization reaction Methods 0.000 claims description 7
- 244000043261 Hevea brasiliensis Species 0.000 claims description 6
- 229920003052 natural elastomer Polymers 0.000 claims description 6
- 229920001194 natural rubber Polymers 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 229920001195 polyisoprene Polymers 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229910018540 Si C Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000001012 protector Effects 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 10
- 239000005864 Sulphur Substances 0.000 abstract 1
- 238000012790 confirmation Methods 0.000 description 28
- 230000003014 reinforcing effect Effects 0.000 description 23
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 18
- 238000010411 cooking Methods 0.000 description 17
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 241001441571 Hiodontidae Species 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 229920003048 styrene butadiene rubber Polymers 0.000 description 11
- 239000002174 Styrene-butadiene Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 8
- 235000019241 carbon black Nutrition 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 150000001282 organosilanes Chemical class 0.000 description 8
- 229920002545 silicone oil Polymers 0.000 description 7
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 5
- 238000005096 rolling process Methods 0.000 description 5
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000002787 reinforcement Effects 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000010692 aromatic oil Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 125000004354 sulfur functional group Chemical group 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
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000001808 coupling effect Effects 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000003607 modifier Substances 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
- 230000036961 partial effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000011265 semifinished product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000008096 xylene 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
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 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
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-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
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-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
- PYKCEDJHRUUDRK-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-2-methylpropanenitrile Chemical compound CC(C)(C)N=NC(C)(C)C#N PYKCEDJHRUUDRK-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-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
- 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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- SANOBPWVEQEGQR-UHFFFAOYSA-N N(=O)O.CC(C)CC(C)C Chemical compound N(=O)O.CC(C)CC(C)C SANOBPWVEQEGQR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001356 alkyl thiols Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003738 black carbon Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000002897 diene group Chemical group 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 235000021110 pickles Nutrition 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
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol 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
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- ISJNFTWEKXOMIH-UHFFFAOYSA-N tert-butyl(2-methylbutan-2-yl)diazene nitrous acid Chemical compound N(=O)O.C(C)(C)(C)N=NC(C)(CC)C ISJNFTWEKXOMIH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
-
- 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
-
- 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
- B60C1/0008—Compositions of the inner liner
-
- 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
-
- 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
- B60C1/0025—Compositions of the sidewalls
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- 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
- C08K5/5403—Silicon-containing compounds containing no other elements than carbon or hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
- C08L23/22—Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
-
- 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
-
- 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
-
- 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
- C08L9/06—Copolymers with styrene
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)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9709047 | 1997-07-11 | ||
| FR97/09047 | 1997-07-11 | ||
| FR9801452 | 1998-02-04 | ||
| FR98/01452 | 1998-02-04 | ||
| PCT/EP1998/004308 WO1999002602A1 (fr) | 1997-07-11 | 1998-07-10 | Composition de caoutchouc dienique renforcee d'une charge blanche, comportant a titre d'agent de couplage (charge blanche/elastomere) un polyorganosiloxane multifonctionnalise |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2296010A1 true CA2296010A1 (fr) | 1999-01-21 |
Family
ID=26233680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002296010A Abandoned CA2296010A1 (fr) | 1997-07-11 | 1998-07-10 | Composition de caoutchouc dienique renforcee d'une charge blanche, comportant a titre d'agent de couplage (charge blanche/elastomere) un polyorganosiloxane multifonctionnalise |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6313205B1 (enExample) |
| EP (1) | EP0996676B1 (enExample) |
| JP (1) | JP2001509530A (enExample) |
| KR (1) | KR100511701B1 (enExample) |
| CN (1) | CN1214069C (enExample) |
| AU (1) | AU8807198A (enExample) |
| BR (1) | BR9811001A (enExample) |
| CA (1) | CA2296010A1 (enExample) |
| DE (1) | DE69806008T2 (enExample) |
| ES (1) | ES2177038T3 (enExample) |
| PL (1) | PL338041A1 (enExample) |
| WO (1) | WO1999002602A1 (enExample) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19905820A1 (de) * | 1998-10-27 | 2000-05-04 | Degussa | Schwefelfunktionelle Polyorganosilane |
| WO2001096442A1 (fr) * | 2000-06-16 | 2001-12-20 | Societe De Technologie Michelin | Composition de caoutchouc pour pneumatique comportant un polyorganosiloxane multifonctionnel a titre d'agent de couplage |
| CN1257211C (zh) | 2000-07-31 | 2006-05-24 | 米其林技术公司 | 轮胎胎面 |
| DE10044989A1 (de) * | 2000-09-11 | 2002-03-21 | Bayer Ag | Flüssige schwefelhaltige Oligosiloxane und ihre Verwendung in Kautschukmischungen |
| DE60221184T2 (de) * | 2001-05-15 | 2008-04-10 | Sumitomo Rubber Industries Ltd., Kobe | Kautschukzusammensetzung für Reifenlauffläche und Reifen mit derselben |
| 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 |
| JP3826081B2 (ja) * | 2001-09-04 | 2006-09-27 | 横浜ゴム株式会社 | 空気入りタイヤ及びその製造方法 |
| AU2003299302A1 (en) * | 2002-12-19 | 2004-07-14 | Michelin Recherche Et Technique S.A. | Rubber composition for tyres, comprising a polyorganosiloxane oligomer as coupling agent |
| FR2849045B1 (fr) * | 2002-12-19 | 2005-01-21 | Rhodia Chimie Sa | Oligomeres polyorganosiloxane portant des fonctions thiols ou episulfures et leurs procedes de preparation |
| JP4243962B2 (ja) * | 2003-02-27 | 2009-03-25 | 横浜ゴム株式会社 | 空気入りタイヤ及びその製造方法 |
| CA2446474C (en) * | 2003-10-24 | 2011-11-29 | Rui Resendes | Silica-filled elastomeric compounds |
| MY164448A (en) * | 2003-12-15 | 2017-12-15 | Ciba Holding Inc | Coupling agents between filler and elastomer |
| CN101180344B (zh) | 2005-03-24 | 2012-01-11 | 株式会社普利司通 | 具有低挥发性有机化合物（voc）释放的配混二氧化硅补强橡胶 |
| FR2886303B1 (fr) * | 2005-05-26 | 2007-07-20 | Rhodia Chimie Sa | Utilisation d'une combinaison particuliere d'un agent de couplage et d'un agent de recouvrement, comme systeme de couplage(charge blanche-elastomere) dans les compositions de caoutchouc comprenant une charge inorganique |
| JP5520483B2 (ja) * | 2005-09-21 | 2014-06-11 | チバ ホールディング インコーポレーテッド | 改善された加工性を有する充填ゴム配合物 |
| US7915368B2 (en) | 2007-05-23 | 2011-03-29 | Bridgestone Corporation | Method for making alkoxy-modified silsesquioxanes |
| US8501895B2 (en) | 2007-05-23 | 2013-08-06 | Bridgestone Corporation | Method for making alkoxy-modified silsesquioxanes and amino alkoxy-modified silsesquioxanes |
| US8962746B2 (en) | 2007-12-27 | 2015-02-24 | Bridgestone Corporation | Methods of making blocked-mercapto alkoxy-modified silsesquioxane compounds |
| US8794282B2 (en) | 2007-12-31 | 2014-08-05 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for improved metal adhesion and metal adhesion retention to cured rubber |
| US8097674B2 (en) | 2007-12-31 | 2012-01-17 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxanes in silica-filled rubber with low volatile organic chemical evolution |
| DE102008001007A1 (de) * | 2008-04-04 | 2009-10-08 | Robert Bosch Gmbh | Silikon-Polymer modifizierte Gummi-Zusammensetzungen, Verfahren zu ihrer Herstellung sowie dieses Material umfassende Scheibenwischer |
| CN101260190B (zh) * | 2008-04-28 | 2011-04-27 | 华南理工大学 | 多官能度聚硅氧烷偶联剂及其制备方法 |
| FR2940290B1 (fr) | 2008-12-22 | 2010-12-31 | Michelin Soc Tech | Agent de couplage mercaptosilane bloque |
| FR2945815B1 (fr) | 2009-05-20 | 2011-07-01 | Michelin Soc Tech | Composition de caoutchouc comportant un agent de couplage organosilane |
| FR2947552B1 (fr) | 2009-05-20 | 2011-08-26 | Michelin Soc Tech | Agent de couplage organosilane |
| FR2954774B1 (fr) | 2009-10-30 | 2012-01-06 | Michelin Soc Tech | Methode de preparation d'un melange maitre de caoutchouc naturel 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 |
| 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 |
| US8642691B2 (en) | 2009-12-28 | 2014-02-04 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for improved metal adhesion and metal adhesion retention to cured rubber |
| FR2962440B1 (fr) * | 2010-07-12 | 2012-08-03 | Total Raffinage Marketing | Procede de preparation de polymeres greffes sans amorceur et sans solvant et compositions bitume/polymere comprenant lesdits polymeres greffes |
| 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 |
| 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 |
| 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 |
| FR2981079B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode pour preparer un melange maitre d'elastomere dienique et de silice |
| FR2981081B1 (fr) | 2011-10-11 | 2013-11-01 | Michelin Soc Tech | Methode de preparation d'un melange maitre de caoutchouc naturel et de silice |
| FR2984326B1 (fr) | 2011-12-16 | 2014-01-10 | Michelin Soc Tech | Agent de couplage mercaptosilane bloque |
| WO2014129662A1 (ja) * | 2013-02-25 | 2014-08-28 | 横浜ゴム株式会社 | タイヤ用ゴム組成物及びこれを用いる空気入りタイヤ |
| US9550850B2 (en) * | 2013-02-25 | 2017-01-24 | The Yokohama Rubber Co., Ltd. | Rubber composition for tire tread, and pneumatic tire using same |
| CN105008451B (zh) * | 2013-02-25 | 2017-07-14 | 横滨橡胶株式会社 | 轮胎胎面用橡胶组合物及使用该橡胶组合物的充气轮胎 |
| EP3086928B1 (en) | 2013-12-27 | 2019-09-11 | Bridgestone Corporation | Vulcanizates and tire components prepared from compositions including mercapto-functional siloxanes |
| JP6247591B2 (ja) * | 2014-05-08 | 2017-12-13 | 株式会社ブリヂストン | ゴム組成物、インナーライナー、シーラントおよび空気入りタイヤ |
| CN107406689A (zh) | 2014-12-31 | 2017-11-28 | 株式会社普利司通 | 用于将钢合金粘附到橡胶的氨基烷氧基改性倍半硅氧烷粘合剂 |
| 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 |
| EP3263359A1 (en) * | 2016-06-28 | 2018-01-03 | Sumitomo Rubber Industries, Ltd. | Rubber composition for sealants |
| FR3053337B1 (fr) | 2016-06-30 | 2018-07-06 | Compagnie Generale Des Etablissements Michelin | Polysulfure de monohydroxysilane |
| FR3053345B1 (fr) | 2016-06-30 | 2018-07-06 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un agent de couplage polysulfure de monohydroxysilane |
| CN109641482B (zh) | 2016-09-02 | 2021-11-05 | 株式会社普利司通 | 具有通过聚合物胶水的原位硅氢加成制备的多个硅烷官能团的顺式-1,4-聚二烯的制备 |
| FR3060565A1 (fr) | 2016-12-16 | 2018-06-22 | Michelin & Cie | Polysulfure d'alcoxysilane |
| 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 |
| 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 |
| 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 |
| CN116082641B (zh) * | 2021-11-08 | 2024-07-09 | 中蓝晨光化工有限公司 | 一种t型对称结构的大分子烷氧基硅烷处理剂及其制备方法与应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1310379A (en) * | 1970-12-10 | 1973-03-21 | Ppg Industries Inc | Tire tread |
| JPS6248743A (ja) * | 1985-08-28 | 1987-03-03 | Shin Etsu Chem Co Ltd | ゴム組成物 |
| US4725630A (en) * | 1987-06-01 | 1988-02-16 | Wacker Silicones Corporation | α, β-unsaturated carbonyl-functional silicone compositions |
| US6191247B1 (en) * | 1996-04-10 | 2001-02-20 | The Yokohama Rubber Co., Ltd. | Polysiloxane composition having superior storage stability and rubber composition containing same |
-
1998
- 1998-07-10 KR KR10-2000-7000257A patent/KR100511701B1/ko not_active Expired - Fee Related
- 1998-07-10 WO PCT/EP1998/004308 patent/WO1999002602A1/fr not_active Ceased
- 1998-07-10 PL PL98338041A patent/PL338041A1/xx unknown
- 1998-07-10 BR BR9811001-2A patent/BR9811001A/pt not_active IP Right Cessation
- 1998-07-10 DE DE69806008T patent/DE69806008T2/de not_active Expired - Fee Related
- 1998-07-10 CA CA002296010A patent/CA2296010A1/fr not_active Abandoned
- 1998-07-10 CN CNB988076578A patent/CN1214069C/zh not_active Expired - Fee Related
- 1998-07-10 AU AU88071/98A patent/AU8807198A/en not_active Abandoned
- 1998-07-10 ES ES98939630T patent/ES2177038T3/es not_active Expired - Lifetime
- 1998-07-10 JP JP2000502111A patent/JP2001509530A/ja not_active Ceased
- 1998-07-10 EP EP98939630A patent/EP0996676B1/fr not_active Expired - Lifetime
-
2000
- 2000-01-10 US US09/480,768 patent/US6313205B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR100511701B1 (ko) | 2005-09-02 |
| JP2001509530A (ja) | 2001-07-24 |
| AU8807198A (en) | 1999-02-08 |
| DE69806008D1 (de) | 2002-07-18 |
| KR20010021698A (ko) | 2001-03-15 |
| US6313205B1 (en) | 2001-11-06 |
| CN1265126A (zh) | 2000-08-30 |
| ES2177038T3 (es) | 2002-12-01 |
| CN1214069C (zh) | 2005-08-10 |
| DE69806008T2 (de) | 2002-11-28 |
| PL338041A1 (en) | 2000-09-25 |
| BR9811001A (pt) | 2000-11-07 |
| WO1999002602A1 (fr) | 1999-01-21 |
| EP0996676A1 (fr) | 2000-05-03 |
| EP0996676B1 (fr) | 2002-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0996676B1 (fr) | Composition de caoutchouc dienique renforcee d'une charge blanche, comportant a titre d'agent de couplage (charge blanche/elastomere) un polyorganosiloxane multifonctionnalise | |
| EP1115785B1 (fr) | Systeme de couplage (charge blanche/elastomere dienique) a base d'alkoxysilane polysulfure, d'enamine et de derive guanidique | |
| EP1265955B1 (fr) | Composition de caoutchouc pour pneumatique comportant un agent de couplage (charge blanche/elastomere) a fonction ester | |
| EP1265956B1 (fr) | Composition de caoutchouc pour pneumatique comportant un agent de couplage (charge blanche/elastomere dienique) active par un initiateur radicalaire a amor age thermique | |
| FR2823215A1 (fr) | Pneumatique et bande de roulement de pneumatique comportant a titre d'agent de couplage un tetrasulfure de bis-alkoxysilane | |
| CA2425330A1 (fr) | Composition de caoutchouc comportant a titre d'agent de couplage un organosilane polyfonctionnel | |
| EP1102812A1 (fr) | Systeme de couplage (charge blanche/elastomere dienique) a base d'alkoxysilane polysulfure, de dithiophosphate de zinc et de derive guanidique | |
| WO2001055252A1 (fr) | Composition de caoutchouc pour pneumatique comportant une charge inorganique renforçante et un systeme de couplage (charge inorganique/elastomere) | |
| WO2001055253A1 (fr) | Composition de caoutchouc pour pneumatique comportant une charge inorganique renforçante et un systeme de couplage (charge inorganique/elastomere) | |
| FR2886304A1 (fr) | Composition de caoutchouc pour pneumatique comportant un systeme de couplage organosilicique | |
| EP2212379A2 (fr) | Composition de caoutchouc pour pneumatique comportant un agent de recouvrement hydroxysilane | |
| CA2444025A1 (fr) | Organoxysilanes polysulfures utilisables notamment en tant qu'agent de couplage, compositions d'elastomere(s) les contenant et articles en elastomere(s) prepares a partir de telles compositions | |
| CA2422370A1 (fr) | Composition de caoutchouc pour pneumatique comportant un citraconimido-alkoxysilane a titre d'agent de couplage | |
| EP1409581A1 (fr) | Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiosulfenamide | |
| EP1474475B1 (fr) | Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiosulfenamide | |
| EP1576044A1 (fr) | COMPOSITION DE CAOUTCHOUC POUR PNEUMATIQUE COMPORTANT UN OLIGOMERE POLYORGANOSILOXANE A TITRE D’AGENT DE COUPLAGE | |
| EP1517799B1 (fr) | SEL DE THIOURONIUM A TITRE D AGENT ANTI-REVERSION DANS UNE C OMPOSITION DE CAOUTCHOUC VULCANISABLE ET PNEUMATIQUE A BASE D'UNE TELLE COMPOSITION | |
| EP1525259A1 (fr) | Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polysulfure cyclique | |
| WO2003097734A1 (fr) | Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiobenzothiazyle | |
| FR3053345A1 (fr) | Composition de caoutchouc comprenant un agent de couplage polysulfure de monohydroxysilane | |
| MXPA00000387A (en) | Diene rubber composition reinforced with white filler, comprising as coupling agent (white filler/elastomer) a multifunctionalized polyorganosiloxane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |