CA2740175A1 - Sulfur-containing cycloaliphatic compound, filled sulfur-vulcanizable elastomer composition containing sulfur-containing cycloaliphatic compound and articles fabricated therefrom - Google Patents
Sulfur-containing cycloaliphatic compound, filled sulfur-vulcanizable elastomer composition containing sulfur-containing cycloaliphatic compound and articles fabricated therefrom Download PDFInfo
- Publication number
- CA2740175A1 CA2740175A1 CA2740175A CA2740175A CA2740175A1 CA 2740175 A1 CA2740175 A1 CA 2740175A1 CA 2740175 A CA2740175 A CA 2740175A CA 2740175 A CA2740175 A CA 2740175A CA 2740175 A1 CA2740175 A1 CA 2740175A1
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- sulfur
- bis
- rubber
- mercapto
- 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
- 229920001971 elastomer Polymers 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 123
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 70
- 239000011593 sulfur Substances 0.000 title claims abstract description 70
- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
- 239000000806 elastomer Substances 0.000 title claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 239000004971 Cross linker Substances 0.000 claims abstract description 19
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 239000005060 rubber Substances 0.000 claims description 81
- 239000000945 filler Substances 0.000 claims description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 49
- -1 2-ethylhexyl Chemical group 0.000 claims description 31
- 239000000377 silicon dioxide Substances 0.000 claims description 22
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 13
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 13
- 229910000077 silane Inorganic materials 0.000 claims description 13
- 229920002857 polybutadiene Polymers 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 10
- OBEAYGIWBMQVKN-UHFFFAOYSA-N 2-[3,4-bis(2-sulfanylethyl)cyclohexyl]ethanethiol Chemical compound SCCC1CCC(CCS)C(CCS)C1 OBEAYGIWBMQVKN-UHFFFAOYSA-N 0.000 claims description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 239000005062 Polybutadiene Substances 0.000 claims description 7
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 7
- 239000005077 polysulfide Substances 0.000 claims description 7
- 229920001021 polysulfide Polymers 0.000 claims description 7
- 150000008117 polysulfides Polymers 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 6
- VHUAJJUEBGBMFV-UHFFFAOYSA-N s-[2-[3,4-bis(2-acetylsulfanylethyl)cyclohexyl]ethyl] ethanethioate Chemical compound CC(=O)SCCC1CCC(CCSC(C)=O)C(CCSC(C)=O)C1 VHUAJJUEBGBMFV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 4
- DEDLYXHHUFCCBW-UHFFFAOYSA-N 2-[2,4,6-trimethyl-4,6-bis(2-sulfanylethyl)-1,3,5,2,4,6-trioxatrisilinan-2-yl]ethanethiol Chemical compound SCC[Si]1(C)O[Si](C)(CCS)O[Si](C)(CCS)O1 DEDLYXHHUFCCBW-UHFFFAOYSA-N 0.000 claims description 3
- JHTXAARNQPIMTC-UHFFFAOYSA-N 2-[3,5,7,9-tetrakis(2-sulfanylethyl)cyclodecyl]ethanethiol Chemical compound SCCC1CC(CCS)CC(CCS)CC(CCS)CC(CCS)C1 JHTXAARNQPIMTC-UHFFFAOYSA-N 0.000 claims description 3
- GWELISGQQPRTBJ-UHFFFAOYSA-N 2-[3,5,7-tris(2-sulfanylethyl)cyclooctyl]ethanethiol Chemical compound SCCC1CC(CCS)CC(CCS)CC(CCS)C1 GWELISGQQPRTBJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002943 EPDM rubber Polymers 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UDSWPHJWACZZHK-UHFFFAOYSA-N o-[2-[4,6-bis(2-acetylsulfanylethyl)-2,4,6-trimethyl-1,3,5,2,4,6-trioxatrisilinan-2-yl]ethyl] ethanethioate Chemical compound CC(=S)OCC[Si]1(C)O[Si](C)(CCSC(C)=O)O[Si](C)(CCSC(C)=O)O1 UDSWPHJWACZZHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920001195 polyisoprene Polymers 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- PNBWQOOPOMGVSA-UHFFFAOYSA-N s-[2-[3,4-bis(2-acetylsulfanylethyl)cyclopentyl]ethyl] ethanethioate Chemical compound CC(=O)SCCC1CC(CCSC(C)=O)C(CCSC(C)=O)C1 PNBWQOOPOMGVSA-UHFFFAOYSA-N 0.000 claims description 3
- BKNGPSHKIVJZHF-UHFFFAOYSA-N s-[2-[3,5,7,9-tetrakis(2-acetylsulfanylethyl)cyclodecyl]ethyl] ethanethioate Chemical compound CC(=O)SCCC1CC(CCSC(C)=O)CC(CCSC(C)=O)CC(CCSC(C)=O)CC(CCSC(C)=O)C1 BKNGPSHKIVJZHF-UHFFFAOYSA-N 0.000 claims description 3
- AHVREISWKMRAKI-UHFFFAOYSA-N s-[2-[3,5,7-tris(2-acetylsulfanylethyl)cyclooctyl]ethyl] ethanethioate Chemical compound CC(=O)SCCC1CC(CCSC(C)=O)CC(CCSC(C)=O)CC(CCSC(C)=O)C1 AHVREISWKMRAKI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000005023 xylyl group Chemical group 0.000 claims description 3
- HTSHECMMROIDET-UHFFFAOYSA-N 6-[3,4-bis(6-sulfanylhexyl)cyclohexyl]hexane-1-thiol Chemical compound SCCCCCCC1CCC(CCCCCCS)C(CCCCCCS)C1 HTSHECMMROIDET-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005065 High vinyl polybutadiene Substances 0.000 claims description 2
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-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
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229920003049 isoprene rubber Polymers 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
- NGAHEJQQIIVZTH-UHFFFAOYSA-N s-[3-[3,4-bis(3-acetylsulfanylpropyl)cyclohexyl]propyl] ethanethioate Chemical compound CC(=O)SCCCC1CCC(CCCSC(C)=O)C(CCCSC(C)=O)C1 NGAHEJQQIIVZTH-UHFFFAOYSA-N 0.000 claims description 2
- HUDRFGGMCFUAGP-UHFFFAOYSA-N s-[6-[3,4-bis(6-acetylsulfanylhexyl)cyclohexyl]hexyl] ethanethioate Chemical compound CC(=O)SCCCCCCC1CCC(CCCCCCSC(C)=O)C(CCCCCCSC(C)=O)C1 HUDRFGGMCFUAGP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 238000007720 emulsion polymerization reaction Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 description 25
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 20
- 238000001723 curing Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000006229 carbon black Substances 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 12
- 244000043261 Hevea brasiliensis Species 0.000 description 11
- 229920003052 natural elastomer Polymers 0.000 description 11
- 229920001194 natural rubber Polymers 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000011787 zinc oxide Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 235000021355 Stearic acid Nutrition 0.000 description 9
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000008117 stearic acid Substances 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000013329 compounding Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 238000004073 vulcanization Methods 0.000 description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000014509 gene expression Effects 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 description 5
- 239000004594 Masterbatch (MB) 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
- 229910000323 aluminium silicate Inorganic materials 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229960002447 thiram Drugs 0.000 description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000498 cooling water Substances 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 229920003244 diene elastomer Polymers 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000012990 dithiocarbamate Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000000930 thermomechanical effect Effects 0.000 description 4
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- CCNDOQHYOIISTA-UHFFFAOYSA-N 1,2-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1C(C)(C)OOC(C)(C)C CCNDOQHYOIISTA-UHFFFAOYSA-N 0.000 description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 2
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 2
- 229960002380 dibutyl phthalate Drugs 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 239000013500 performance material Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000002459 porosimetry Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000010058 rubber compounding Methods 0.000 description 2
- 150000004819 silanols Chemical class 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- 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
- C08K5/549—Silicon-containing compounds containing silicon in a ring
-
- 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
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- 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
- 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
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/06—Copolymers with styrene
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- 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
- C08L9/02—Copolymers with acrylonitrile
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/290,368 US8124206B2 (en) | 2008-10-30 | 2008-10-30 | Sulfur-containing cycloaliphatic compound, filled sulfur-vulcanizable elastomer composition containing sulfur-containing cycloaliphatic compound and articles fabricated therefrom |
| US12/290,368 | 2008-10-30 | ||
| PCT/US2009/062666 WO2010059402A1 (en) | 2008-10-30 | 2009-10-30 | Sulfur-containing cycloali phatic compound, filled sulfur-vulcanizable elastomer composition containing sulfur-containing cycloaliphatic compound and articles fabricated therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2740175A1 true CA2740175A1 (en) | 2010-05-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2740175A Abandoned CA2740175A1 (en) | 2008-10-30 | 2009-10-30 | Sulfur-containing cycloaliphatic compound, filled sulfur-vulcanizable elastomer composition containing sulfur-containing cycloaliphatic compound and articles fabricated therefrom |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8124206B2 (enExample) |
| EP (1) | EP2342274B1 (enExample) |
| JP (2) | JP5827126B2 (enExample) |
| KR (1) | KR101659967B1 (enExample) |
| CN (1) | CN102272211B (enExample) |
| BR (1) | BRPI0920618B1 (enExample) |
| CA (1) | CA2740175A1 (enExample) |
| TW (1) | TWI476236B (enExample) |
| WO (1) | WO2010059402A1 (enExample) |
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| KR100996576B1 (ko) | 2003-05-09 | 2010-11-24 | 주식회사 탑 엔지니어링 | 액정적하장치 및 액정적하방법 |
| BR112014000685A2 (pt) * | 2011-07-15 | 2017-11-21 | Momentive Performance Mat Inc | composições estereoisoméricas de trivinil ciclo hexano e processos para a preparação das mesmas |
| EP2853558B1 (de) | 2013-09-27 | 2016-11-09 | Continental Reifen Deutschland GmbH | Schwefelvernetzbare Kautschukmischung |
| CN103756026B (zh) * | 2013-12-04 | 2016-02-17 | 铜陵日兴电子有限公司 | 一种电容器专用混炼胶密封圈及其制备方法 |
| ES2606834T3 (es) | 2013-12-20 | 2017-03-28 | Continental Reifen Deutschland Gmbh | Mezcla de caucho y neumáticos de coche |
| DE102015208813A1 (de) | 2015-05-12 | 2016-11-17 | Continental Reifen Deutschland Gmbh | Monomer zur Copolymerisation mit Alkenen, Dienen, Vinyl-Verbindungen und/oder Vinyliden-Verbindungen, Verfahren zur Herstellung eines Copolymers, Copolymer und Kautschukmischung sowie deren Verwendung |
| US9670379B2 (en) | 2015-07-23 | 2017-06-06 | The Boeing Company | Composites transmissive to visual and infrared radiation and compositions and methods for making the composites |
| US10414870B2 (en) | 2015-07-23 | 2019-09-17 | The Boeing Company | Transparent polymers and methods for making the same |
| US11440349B2 (en) | 2015-10-27 | 2022-09-13 | Sumitomo Rubber Industries, Ltd. | Pneumatic tire and crosslinked rubber composition |
| WO2017073493A1 (ja) | 2015-10-27 | 2017-05-04 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| JP6328723B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| JP6328724B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| CN108349313B (zh) | 2015-10-27 | 2020-10-27 | 住友橡胶工业株式会社 | 充气轮胎和交联橡胶组合物 |
| JP6329612B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| JP6329609B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| US11427029B2 (en) | 2015-10-27 | 2022-08-30 | Sumitomo Rubber Industries, Ltd. | Pneumatic tire and crosslinked rubber composition |
| JP6329611B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| JP6329608B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| JP6329610B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| JP6329607B2 (ja) * | 2015-10-27 | 2018-05-23 | 住友ゴム工業株式会社 | 空気入りタイヤおよび架橋ゴム組成物 |
| US9611375B1 (en) | 2015-11-03 | 2017-04-04 | The Boeing Company | Rapid curing thiol epoxy resin with improved compression strength performance |
| US10307981B2 (en) | 2017-02-15 | 2019-06-04 | VF Asia Limited | Methods for making a footwear article |
| WO2018187243A1 (en) | 2017-04-03 | 2018-10-11 | Eastman Chemical Company | Modified resins and uses thereof |
| EP3606993B1 (en) | 2017-04-03 | 2023-10-11 | Continental Reifen Deutschland GmbH | Modified resins and uses thereof |
| PT3606992T (pt) | 2017-04-03 | 2023-08-24 | Synthomer Adhesive Tech Llc | Resinas modificadas e utilizações das mesmas |
| ES2971873T3 (es) | 2017-04-10 | 2024-06-10 | Continental Reifen Deutschland Gmbh | Resina funcionalizada que tiene un conector polar |
| BR112019021095B1 (pt) | 2017-04-10 | 2023-05-16 | Continental Reifen Deutschland Gmbh | Composição de borracha vulcanizada, e pneu, mangueira, gaxeta, correia ou sola de um sapato |
| ES2968401T3 (es) | 2017-04-10 | 2024-05-09 | Synthomer Adhesive Tech Llc | Resina funcionalizada que tiene un ligador polar |
| US12319795B2 (en) | 2019-12-30 | 2025-06-03 | Bridgestone Corporation | Rubber compositions prepared with a polar polysulfide crosslinking agent |
| EP4397706A4 (en) * | 2021-08-30 | 2025-08-20 | Eneos Mat Corporation | RUBBER COMPOSITION AND METHOD FOR PRODUCING SAME, AND TIRE |
| CN113788935B (zh) * | 2021-10-22 | 2022-05-27 | 韦尔通(厦门)科技股份有限公司 | 一种环氧树脂组合物及其制备方法和应用 |
| CN113943420B (zh) * | 2021-10-22 | 2022-10-04 | 韦尔通(厦门)科技股份有限公司 | 一种uv光固化树脂组合物及其制备方法和应用 |
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| US3284481A (en) * | 1963-10-28 | 1966-11-08 | Dow Chemical Co | alpha, alpha'-bis(substituted sulfonylthio)-p-tolyl ethers |
| US3462472A (en) * | 1967-06-01 | 1969-08-19 | Dow Chemical Co | 1,4- and 1,2-bis(substituted sulfonylthiomethyl)cyclohexane |
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| EP0530590B1 (de) * | 1991-08-30 | 1996-01-17 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von Dienkautschuk-Vulkanisaten |
| CA2104537A1 (en) * | 1993-06-18 | 1994-12-19 | Paul Harry Sandstrom | Silica reinforced rubber composition |
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| EP2277939B1 (en) * | 2005-03-24 | 2017-02-22 | Bridgestone Corporation | Compounding silica-reinforced rubber with low volatile organic compound (VOC) emission |
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-
2008
- 2008-10-30 US US12/290,368 patent/US8124206B2/en active Active
-
2009
- 2009-10-26 TW TW098136177A patent/TWI476236B/zh not_active IP Right Cessation
- 2009-10-30 CN CN2009801533833A patent/CN102272211B/zh active Active
- 2009-10-30 CA CA2740175A patent/CA2740175A1/en not_active Abandoned
- 2009-10-30 EP EP09752034.0A patent/EP2342274B1/en active Active
- 2009-10-30 JP JP2011534791A patent/JP5827126B2/ja active Active
- 2009-10-30 BR BRPI0920618-3A patent/BRPI0920618B1/pt active IP Right Grant
- 2009-10-30 WO PCT/US2009/062666 patent/WO2010059402A1/en not_active Ceased
- 2009-10-30 KR KR1020117012275A patent/KR101659967B1/ko active Active
-
2012
- 2012-01-17 US US13/351,818 patent/US8846170B2/en active Active
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2015
- 2015-02-19 JP JP2015030216A patent/JP6314096B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015134925A (ja) | 2015-07-27 |
| US8846170B2 (en) | 2014-09-30 |
| EP2342274B1 (en) | 2013-04-17 |
| JP6314096B2 (ja) | 2018-04-18 |
| KR20110079914A (ko) | 2011-07-11 |
| TWI476236B (zh) | 2015-03-11 |
| KR101659967B1 (ko) | 2016-09-27 |
| BRPI0920618B1 (pt) | 2019-09-17 |
| JP5827126B2 (ja) | 2015-12-02 |
| CN102272211B (zh) | 2013-10-02 |
| US20120116002A1 (en) | 2012-05-10 |
| JP2012507610A (ja) | 2012-03-29 |
| EP2342274A1 (en) | 2011-07-13 |
| CN102272211A (zh) | 2011-12-07 |
| US8124206B2 (en) | 2012-02-28 |
| WO2010059402A1 (en) | 2010-05-27 |
| TW201035208A (en) | 2010-10-01 |
| US20100112259A1 (en) | 2010-05-06 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20151030 |