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 (https=) |
| EP (1) | EP2432786B1 (https=) |
| JP (1) | JP5806659B2 (https=) |
| CN (1) | CN102439016B (https=) |
| FR (1) | FR2947552B1 (https=) |
| RU (1) | RU2575932C2 (https=) |
| WO (1) | WO2010133373A1 (https=) |
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 |
| US3873489A (en) | 1971-08-17 | 1975-03-25 | Degussa | Rubber compositions containing silica and an organosilane |
| BE787691A (fr) | 1971-08-17 | 1973-02-19 | Degussa | Composes organosiliciques contenant du soufre |
| 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 |
| WO1999002590A1 (fr) | 1997-07-07 | 1999-01-21 | Compagnie Generale Des Etablissements Michelin - Michelin & Cie | Composition de caoutchouc de pneumatique couleur |
| FR2765881B1 (fr) * | 1997-07-09 | 1999-08-13 | Michelin & Cie | Composition de caoutchouc vulcanisable au soufre contenant de la silice |
| PL338041A1 (en) | 1997-07-11 | 2000-09-25 | Michelin & Cie | Diene rubber compound containing a white filler and a multifunctionalised polyorganosiloxane as a cross-linking agent (for the filler/elastomer mix) |
| KR100632720B1 (ko) | 1997-11-28 | 2006-10-16 | 꽁빠니 제네랄 드 에따블리세망 미쉘린-미쉘린 에 씨 | 보강 알루미늄계 충전제, 이의 제조방법, 이를 포함하는 고무 조성물, 및 이에 의해 보강된 타이어 및 타이어용 트레드 |
| DE19825796A1 (de) * | 1998-06-10 | 1999-12-16 | Degussa | Neue oligomere Organosilanpolysulfane, deren Verwendung in Kautschukmischungen und zur Herstellung von Formkörpern |
| EP1115785B1 (fr) | 1998-07-22 | 2002-10-09 | Société de Technologie Michelin | Systeme de couplage (charge blanche/elastomere dienique) a base d'alkoxysilane polysulfure, d'enamine et de derive guanidique |
| AU5161699A (en) | 1998-07-22 | 2000-02-14 | Michelin Recherche Et Technique S.A. | Coupling system (white filler/diene elastomer) based on polysulphide alkoxysilane, zinc dithiophosphate and guanidine derivative |
| 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 |
| EP1114093B1 (fr) | 1999-05-28 | 2004-10-13 | Société de Technologie Michelin | Composition de caoutchouc pour pneumatique, a base d'elastomere dienique et d'un oxyde de titane renfor ant |
| JP5022548B2 (ja) | 1999-05-28 | 2012-09-12 | ソシエテ ド テクノロジー ミシュラン | ジエンエラストマー及び強化酸化チタンに基づくタイヤ用ゴム組成物 |
| 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. |
| JP4391238B2 (ja) * | 2001-12-20 | 2009-12-24 | ソシエテ ド テクノロジー ミシュラン | ポリチオスルフェンアミド官能基を有するカップリング剤を含むタイヤ用ゴム組成物 |
| WO2003097734A1 (fr) * | 2002-05-15 | 2003-11-27 | Societe De Technologie Michelin | Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiobenzothiazyle |
| US9303148B2 (en) * | 2004-07-29 | 2016-04-05 | Compagnie Generale Des Etablissements | Rubber composition devoid of or practically devoid of zinc |
| 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 |
-
2009
- 2009-05-20 FR FR0902452A patent/FR2947552B1/fr not_active Expired - Fee Related
-
2010
- 2010-05-20 CN CN201080021988.XA patent/CN102439016B/zh not_active Expired - Fee Related
- 2010-05-20 RU RU2011151971/04A patent/RU2575932C2/ru not_active IP Right Cessation
- 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 JP JP2012511199A patent/JP5806659B2/ja not_active Expired - Fee Related
- 2010-05-20 US US13/321,825 patent/US8987361B2/en not_active Expired - Fee Related
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| 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 |
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Also Published As
| Publication number | Publication date |
|---|---|
| FR2947552A1 (fr) | 2011-01-07 |
| EP2432786A1 (fr) | 2012-03-28 |
| CN102439016B (zh) | 2015-07-22 |
| CN102439016A (zh) | 2012-05-02 |
| US8987361B2 (en) | 2015-03-24 |
| FR2947552B1 (fr) | 2011-08-26 |
| WO2010133373A1 (fr) | 2010-11-25 |
| US20120165468A1 (en) | 2012-06-28 |
| JP5806659B2 (ja) | 2015-11-10 |
| EP2432786B1 (fr) | 2015-05-13 |
| JP2012527499A (ja) | 2012-11-08 |
| RU2011151971A (ru) | 2013-07-10 |
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