RU2575932C2 - Органосилановое связующее - Google Patents
Органосилановое связующее Download PDFInfo
- Publication number
- RU2575932C2 RU2575932C2 RU2011151971/04A RU2011151971A RU2575932C2 RU 2575932 C2 RU2575932 C2 RU 2575932C2 RU 2011151971/04 A RU2011151971/04 A RU 2011151971/04A RU 2011151971 A RU2011151971 A RU 2011151971A RU 2575932 C2 RU2575932 C2 RU 2575932C2
- Authority
- RU
- Russia
- Prior art keywords
- organosilane
- carbon atoms
- binder
- formula
- composition
- Prior art date
Links
- 150000001282 organosilanes Chemical class 0.000 title claims abstract description 35
- 239000007822 coupling agent Substances 0.000 title abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- RUHCATDGSSLXPZ-UHFFFAOYSA-N dicarboxyazaniumylideneazanide Chemical compound OC(=O)[N+](=[N-])C(O)=O RUHCATDGSSLXPZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 6
- 239000011230 binding agent Substances 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 111
- 238000012545 processing Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 150000004756 silanes Chemical class 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 description 49
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 239000005060 rubber Substances 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000011256 inorganic filler Substances 0.000 description 28
- 229910003475 inorganic filler Inorganic materials 0.000 description 27
- 238000004073 vulcanization Methods 0.000 description 25
- 229920003244 diene elastomer Polymers 0.000 description 20
- 239000000377 silicon dioxide Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 230000003014 reinforcing effect Effects 0.000 description 15
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 14
- 235000012239 silicon dioxide Nutrition 0.000 description 13
- 239000011701 zinc Substances 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 239000000806 elastomer Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 238000005096 rolling process Methods 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 229910052725 zinc Inorganic materials 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- 241001441571 Hiodontidae Species 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- OAPAXRSWOWOBMN-UHFFFAOYSA-N dihydroxy-methyl-[3-(octyldisulfanyl)propyl]silane Chemical compound CCCCCCCCSSCCC[Si](C)(O)O OAPAXRSWOWOBMN-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 230000002028 premature Effects 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920001021 polysulfide Polymers 0.000 description 4
- 239000005077 polysulfide Substances 0.000 description 4
- 150000008117 polysulfides Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 101000717377 Homo sapiens Ribokinase Proteins 0.000 description 3
- 102100020783 Ribokinase Human genes 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- AQOXPHXAEXAUKP-UHFFFAOYSA-N S-[3-(dihydroxymethylsilyl)propyl] octanethioate Chemical compound CCCCCCCC(=O)SCCC[SiH2]C(O)O AQOXPHXAEXAUKP-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical class [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- -1 ethoxyl groups Chemical group 0.000 description 2
- JXMLAPZRDDWRRV-UHFFFAOYSA-N ethyl n-(ethoxycarbonylamino)carbamate Chemical compound CCOC(=O)NNC(=O)OCC JXMLAPZRDDWRRV-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012764 mineral filler 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
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- LOOUJXUUGIUEBC-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propane-1-thiol Chemical compound COC(OC)[SiH2]CCCS LOOUJXUUGIUEBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 229920006978 SSBR Polymers 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 230000003534 oscillatory effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical group CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0902452A FR2947552B1 (fr) | 2009-05-20 | 2009-05-20 | Agent de couplage organosilane |
| FR0902452 | 2009-05-20 | ||
| PCT/EP2010/003117 WO2010133373A1 (fr) | 2009-05-20 | 2010-05-20 | Agent de couplage organosilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2011151971A RU2011151971A (ru) | 2013-07-10 |
| RU2575932C2 true RU2575932C2 (ru) | 2016-02-27 |
Family
ID=41328474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011151971/04A RU2575932C2 (ru) | 2009-05-20 | 2010-05-20 | Органосилановое связующее |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8987361B2 (enExample) |
| EP (1) | EP2432786B1 (enExample) |
| JP (1) | JP5806659B2 (enExample) |
| CN (1) | CN102439016B (enExample) |
| FR (1) | FR2947552B1 (enExample) |
| RU (1) | RU2575932C2 (enExample) |
| WO (1) | WO2010133373A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2984326B1 (fr) * | 2011-12-16 | 2014-01-10 | Michelin Soc Tech | Agent de couplage mercaptosilane bloque |
| FR3053337B1 (fr) * | 2016-06-30 | 2018-07-06 | Compagnie Generale Des Etablissements Michelin | Polysulfure de monohydroxysilane |
| JP2018080754A (ja) * | 2016-11-16 | 2018-05-24 | 内山工業株式会社 | エンジン回りのガスケット及びその製造方法 |
| CN110016166A (zh) * | 2017-12-05 | 2019-07-16 | 东洋橡胶工业株式会社 | 橡胶组合物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US13A (en) * | 1836-08-31 | Mode of laying veneers on ogee and other moldings | ||
| RU99120664A (ru) * | 1998-09-29 | 2001-07-20 | Дегусса-Хюльс Акциенгезельшафт | Сульфанилсиланы |
| RU2267493C2 (ru) * | 2004-01-15 | 2006-01-10 | Семен Моисеевич Кавун | Блокированный меркаптосилановый сшивающий агент для резиновых смесей с кремнекислотными и минеральными наполнителями |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1310379A (en) | 1970-12-10 | 1973-03-21 | Ppg Industries Inc | Tire tread |
| BE787691A (fr) | 1971-08-17 | 1973-02-19 | Degussa | Composes organosiliciques contenant du soufre |
| US3873489A (en) | 1971-08-17 | 1975-03-25 | Degussa | Rubber compositions containing silica and an organosilane |
| BG25805A3 (en) | 1972-11-13 | 1978-12-12 | Degussa Ag | A rubber mixture |
| SU580840A3 (ru) | 1974-02-07 | 1977-11-15 | Дегусса (Фирма) | Способ получени серосодержащих кремнийорганических соединений |
| US4002594A (en) | 1975-07-08 | 1977-01-11 | Ppg Industries, Inc. | Scorch retardants for rubber reinforced with siliceous pigment and mercapto-type coupling agent |
| FR2673187B1 (fr) | 1991-02-25 | 1994-07-01 | Michelin & Cie | Composition de caoutchouc et enveloppes de pneumatiques a base de ladite composition. |
| DE4415658A1 (de) | 1994-05-04 | 1995-11-09 | Bayer Ag | Schwefelhaltige Organosiliciumverbindungen enthaltende Kautschukmischungen |
| FR2732351B1 (fr) | 1995-03-29 | 1998-08-21 | Michelin & Cie | Composition de caoutchouc pour enveloppe de pneumatique renfermant de la silice dopee aluminium a titre de charge renforcante |
| US5733963A (en) | 1996-02-20 | 1998-03-31 | The Goodyear Tire & Rubber Company | Silica reinforced rubber composition and tire with tread thereof |
| FR2749313A1 (fr) | 1996-05-28 | 1997-12-05 | Michelin & Cie | Composition de caoutchouc dienique a base d'alumine en tant que charge renforcante et son utilisation pour la fabrication d'enveloppes de pneumatiques |
| FR2763593B1 (fr) | 1997-05-26 | 1999-07-09 | Michelin & Cie | Composition de caoutchouc a base de silice destinee a la fabrication d'enveloppes de pneumatiques routiers ayant une resistance au roulement amelioree |
| BR9810559A (pt) | 1997-07-07 | 2000-08-15 | Michelin & Cie | Composição de borracha de pneumático, branca, clara ou colorida, desprovida de negro de fumo, pneumático de cor ou artigo de borracha de um tal pneumático, processo para proteger contra o envelhecimento foto-oxidante uma composição de borracha, e, utilização de um sistema foto-oxidante |
| FR2765881B1 (fr) * | 1997-07-09 | 1999-08-13 | Michelin & Cie | Composition de caoutchouc vulcanisable au soufre contenant de la silice |
| KR100511701B1 (ko) | 1997-07-11 | 2005-09-02 | 꽁빠니 제네랄 드 에따블리세망 미쉘린-미쉘린 에 씨 | 다관능화 폴리오가노실록산을 커플링제(백색충전제/탄성중합체)로서 포함하는, 백색 충전제로 강화된디엔 고무 조성물 |
| CA2310133A1 (fr) | 1997-11-28 | 1999-06-10 | Compagnie Generale Des Etablissements Michelin - Michelin & Cie | Charge alumineuse renforcante et composition de caoutchouc comportant une telle charge |
| DE19825796A1 (de) * | 1998-06-10 | 1999-12-16 | Degussa | Neue oligomere Organosilanpolysulfane, deren Verwendung in Kautschukmischungen und zur Herstellung von Formkörpern |
| ATE226229T1 (de) | 1998-07-22 | 2002-11-15 | Michelin Soc Tech | Haftvermittlerzusammensetzung (weisser füllstoff/dienrubber) die ein alkoxysilanpolysulfid, ein zinkdithiophosphat und ein guanidinderivat enthält |
| CN1256374C (zh) | 1998-07-22 | 2006-05-17 | 米凯林技术公司 | 基于多硫化烷氧基硅烷、烯胺和胍衍生物的偶联体系及其应用，包含该偶联体系的橡胶组合物及其应用 |
| EP1165681A1 (en) | 1999-03-10 | 2002-01-02 | BRIDGESTONE/FIRESTONE, Research, Inc. | Solid silica coupling agent composites in silica rubber |
| DE19915281A1 (de) | 1999-04-03 | 2000-10-05 | Degussa | Kautschukmischungen |
| KR20010072070A (ko) | 1999-05-28 | 2001-07-31 | 미첼 롤리에르 | 디엔 탄성중합체 및 강화 산화티탄을 기재로 하는 공기타이어용 고무 조성물 |
| CA2338160A1 (fr) | 1999-05-28 | 2000-12-07 | Jean-Claude Tardivat | Composition de caoutchouc pour pneumatique, a base d'elastomere dienique et d'un oxyde de titane renforcant |
| DE19951281A1 (de) | 1999-10-25 | 2001-04-26 | Cebim Handelsmij B V | Bauplatten auf der Grundlage von zementgebundenen Holzspanplatten sowie Verfahren zu deren Herstellung und ihre Verwendung |
| ES2256317T3 (es) * | 2000-10-13 | 2006-07-16 | Societe De Technologie Michelin | Organosilano polifuncional utilizable como agente de acoplamiento y su procedimiento de obtencion. |
| DE60225188T2 (de) * | 2001-12-20 | 2009-02-19 | Société de Technologie Michelin | Kautschukzusammensetzung für reifen, die ein kupplungsmittel mit einer polythiosulfenamid-gruppe enthält |
| AU2003233302A1 (en) * | 2002-05-15 | 2003-12-02 | Michelin Recherche Et Technique S.A | Rubber composition for tyre comprising a coupling agent with polythiobenzothiazyl function |
| JP5501563B2 (ja) * | 2004-07-29 | 2014-05-21 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | 亜鉛を含まない又は実質的に含まないゴム組成物 |
| FR2908416B1 (fr) * | 2006-11-09 | 2009-01-16 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique incorporant un nouveau systeme anti-oxydant |
| FR2940290B1 (fr) * | 2008-12-22 | 2010-12-31 | Michelin Soc Tech | Agent de couplage mercaptosilane bloque |
| FR2940302B1 (fr) * | 2008-12-22 | 2012-07-27 | Michelin Soc Tech | Composition de caoutchouc comportant un agent de couplage mercaptosilane bloque |
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2009
- 2009-05-20 FR FR0902452A patent/FR2947552B1/fr not_active Expired - Fee Related
-
2010
- 2010-05-20 RU RU2011151971/04A patent/RU2575932C2/ru not_active IP Right Cessation
- 2010-05-20 JP JP2012511199A patent/JP5806659B2/ja not_active Expired - Fee Related
- 2010-05-20 CN CN201080021988.XA patent/CN102439016B/zh not_active Expired - Fee Related
- 2010-05-20 WO PCT/EP2010/003117 patent/WO2010133373A1/fr not_active Ceased
- 2010-05-20 EP EP10734903.7A patent/EP2432786B1/fr not_active Not-in-force
- 2010-05-20 US US13/321,825 patent/US8987361B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2010133373A1 (fr) | 2010-11-25 |
| EP2432786A1 (fr) | 2012-03-28 |
| EP2432786B1 (fr) | 2015-05-13 |
| CN102439016A (zh) | 2012-05-02 |
| RU2011151971A (ru) | 2013-07-10 |
| JP5806659B2 (ja) | 2015-11-10 |
| FR2947552A1 (fr) | 2011-01-07 |
| CN102439016B (zh) | 2015-07-22 |
| US8987361B2 (en) | 2015-03-24 |
| FR2947552B1 (fr) | 2011-08-26 |
| JP2012527499A (ja) | 2012-11-08 |
| US20120165468A1 (en) | 2012-06-28 |
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