KR100674059B1 - 충전고무용 차단된 메르캅토실란 커플링제 - Google Patents
충전고무용 차단된 메르캅토실란 커플링제 Download PDFInfo
- Publication number
- KR100674059B1 KR100674059B1 KR1019997003423A KR19997003423A KR100674059B1 KR 100674059 B1 KR100674059 B1 KR 100674059B1 KR 1019997003423 A KR1019997003423 A KR 1019997003423A KR 19997003423 A KR19997003423 A KR 19997003423A KR 100674059 B1 KR100674059 B1 KR 100674059B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- silane
- groups
- contain
- blocked mercaptosilane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 82
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 239000005060 rubber Substances 0.000 title claims abstract description 80
- 239000007822 coupling agent Substances 0.000 title description 10
- 239000000945 filler Substances 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 229920000592 inorganic polymer Polymers 0.000 claims abstract 2
- 229910000077 silane Inorganic materials 0.000 claims description 81
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 77
- -1 ethylnorbornyl Chemical group 0.000 claims description 69
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 50
- 229910052717 sulfur Inorganic materials 0.000 claims description 50
- 239000011593 sulfur Substances 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 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 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 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
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 59
- 238000002156 mixing Methods 0.000 abstract description 27
- 238000005859 coupling reaction Methods 0.000 abstract description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract description 7
- 230000008878 coupling Effects 0.000 abstract description 6
- 238000010168 coupling process Methods 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 89
- 150000002148 esters Chemical class 0.000 description 66
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 239000000047 product Substances 0.000 description 41
- 230000008569 process Effects 0.000 description 36
- 150000004756 silanes Chemical class 0.000 description 36
- 238000007792 addition Methods 0.000 description 35
- 238000004821 distillation Methods 0.000 description 33
- 239000002253 acid Substances 0.000 description 31
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000377 silicon dioxide Substances 0.000 description 26
- 125000000524 functional group Chemical group 0.000 description 23
- 238000010992 reflux Methods 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 20
- 229910052783 alkali metal Inorganic materials 0.000 description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 239000006229 carbon black Substances 0.000 description 13
- 235000019241 carbon black Nutrition 0.000 description 13
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 13
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 150000008065 acid anhydrides Chemical class 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 244000043261 Hevea brasiliensis Species 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 229920003052 natural elastomer Polymers 0.000 description 11
- 229920001194 natural rubber Polymers 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 239000012038 nucleophile Substances 0.000 description 10
- 229920000620 organic polymer Polymers 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 150000001340 alkali metals Chemical class 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 239000004594 Masterbatch (MB) Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000004073 vulcanization Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- SMDVDXOWTRMZKF-UHFFFAOYSA-N C1C[SiH2]SC1 Chemical compound C1C[SiH2]SC1 SMDVDXOWTRMZKF-UHFFFAOYSA-N 0.000 description 7
- 239000005062 Polybutadiene Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 150000007970 thio esters Chemical class 0.000 description 6
- 150000003606 tin compounds Chemical class 0.000 description 6
- 150000003609 titanium compounds Chemical class 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 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 5
- VTXSDKVOHQXOBQ-UHFFFAOYSA-N C1CCS[SiH2]C1 Chemical compound C1CCS[SiH2]C1 VTXSDKVOHQXOBQ-UHFFFAOYSA-N 0.000 description 5
- 241001441571 Hiodontidae Species 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 5
- 239000012990 dithiocarbamate Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 235000019645 odor Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000005077 polysulfide Substances 0.000 description 5
- 229920001021 polysulfide Polymers 0.000 description 5
- 150000008117 polysulfides Polymers 0.000 description 5
- 230000002028 premature Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000005096 rolling process Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 4
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 239000002174 Styrene-butadiene Substances 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-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
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000007701 flash-distillation Methods 0.000 description 4
- 150000002357 guanidines Chemical class 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 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 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229960002447 thiram Drugs 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- BFMKFCLXZSUVPI-UHFFFAOYSA-N ethyl but-3-enoate Chemical compound CCOC(=O)CC=C BFMKFCLXZSUVPI-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 3
- 239000004200 microcrystalline wax Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QDFFFDHNDDVFCN-UHFFFAOYSA-N o-(3-trimethoxysilylpropyl) ethanethioate Chemical compound CO[Si](OC)(OC)CCCOC(C)=S QDFFFDHNDDVFCN-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- ZVAHTTMDGSREKY-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCSC(C)=O ZVAHTTMDGSREKY-UHFFFAOYSA-N 0.000 description 3
- MOPINAXCCFNGGW-UHFFFAOYSA-N s-(3-trimethoxysilylpropyl) ethanethioate Chemical compound CO[Si](OC)(OC)CCCSC(C)=O MOPINAXCCFNGGW-UHFFFAOYSA-N 0.000 description 3
- AQSMLSJHYWHNRT-UHFFFAOYSA-N s-(3-trimethoxysilylpropyl) propanethioate Chemical compound CCC(=O)SCCC[Si](OC)(OC)OC AQSMLSJHYWHNRT-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 230000000930 thermomechanical effect Effects 0.000 description 3
- 239000004636 vulcanized rubber Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical class O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 2
- DEILIWSHLDNQRR-UHFFFAOYSA-N 1-(2-triethoxysilyl-4-bicyclo[2.2.1]hept-2-enyl)ethanethione Chemical compound C1CC2C([Si](OCC)(OCC)OCC)=CC1(C(C)=S)C2 DEILIWSHLDNQRR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VRVARBOMFPFVIB-UHFFFAOYSA-N 3-benzylsulfanylpropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCSCC1=CC=CC=C1 VRVARBOMFPFVIB-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
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- KRZHJDOXWGZKTG-UHFFFAOYSA-N o-[3-tri(propan-2-yloxy)silylpropyl] ethanethioate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCOC(C)=S KRZHJDOXWGZKTG-UHFFFAOYSA-N 0.000 description 1
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- CHQXYYLHPRFBKJ-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) hexadecanethioate Chemical compound CCCCCCCCCCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC CHQXYYLHPRFBKJ-UHFFFAOYSA-N 0.000 description 1
- ZEZMKKCCBMDNAF-UHFFFAOYSA-N s-(8-triethoxysilyloctyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCSC(C)=O ZEZMKKCCBMDNAF-UHFFFAOYSA-N 0.000 description 1
- OBRJKPQRGYFBPH-UHFFFAOYSA-N s-(8-trimethoxysilyloctyl) ethanethioate Chemical compound CO[Si](OC)(OC)CCCCCCCCSC(C)=O OBRJKPQRGYFBPH-UHFFFAOYSA-N 0.000 description 1
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- KHTZKHQMYLOHFT-UHFFFAOYSA-N sulfanylidene-(3-triethoxysilylpropoxy)-bis(3-triethoxysilylpropylsulfanyl)-$l^{5}-phosphane Chemical compound CCO[Si](OCC)(OCC)CCCOP(=S)(SCCC[Si](OCC)(OCC)OCC)SCCC[Si](OCC)(OCC)OCC KHTZKHQMYLOHFT-UHFFFAOYSA-N 0.000 description 1
- VGGJNLGZARHOQV-UHFFFAOYSA-N sulfanylidene-tris(3-triethoxysilylpropylsulfanyl)-$l^{5}-phosphane Chemical compound CCO[Si](OCC)(OCC)CCCSP(=S)(SCCC[Si](OCC)(OCC)OCC)SCCC[Si](OCC)(OCC)OCC VGGJNLGZARHOQV-UHFFFAOYSA-N 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical group [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- 238000005496 tempering Methods 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- 150000008111 thiosulfinates Chemical class 0.000 description 1
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- KFZYOLRKZIKUSD-UHFFFAOYSA-N triethoxy(2-hydroxysulfonothioylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCS(O)(=O)=S KFZYOLRKZIKUSD-UHFFFAOYSA-N 0.000 description 1
- BRTXVSVHFSOGED-UHFFFAOYSA-N triethoxy(4-hydroxysulfonothioylbutyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCS(O)(=O)=S BRTXVSVHFSOGED-UHFFFAOYSA-N 0.000 description 1
- RBDAXWQGOZWYFH-UHFFFAOYSA-N triethoxy(4-hydroxysulfonothioylpentyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCC(C)S(O)(=O)=S RBDAXWQGOZWYFH-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- SHQJOFANKPSLCU-UHFFFAOYSA-N triethoxy-(4-hydroxysulfonothioyl-4-propyl-3H-naphthalen-2-yl)silane Chemical compound C1=CC=C2C(CCC)(S(O)(=O)=S)CC([Si](OCC)(OCC)OCC)=CC2=C1 SHQJOFANKPSLCU-UHFFFAOYSA-N 0.000 description 1
- XGCGZQRQPNUUPB-UHFFFAOYSA-N triethoxy-(5-hydroxysulfonothioyl-5-propylcyclohexa-1,3-dien-1-yl)silane Chemical compound CCCC1(S(O)(=O)=S)CC([Si](OCC)(OCC)OCC)=CC=C1 XGCGZQRQPNUUPB-UHFFFAOYSA-N 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
- FVCAMBAGVUGJHH-UHFFFAOYSA-N triethoxy-[5-(hydroxysulfonothioylmethyl)-5-propylcyclohexa-1,3-dien-1-yl]silane Chemical compound CCCC1(CC(=CC=C1)[Si](OCC)(OCC)OCC)CS(=O)(=S)O FVCAMBAGVUGJHH-UHFFFAOYSA-N 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NEYNBSGIXOOZGZ-UHFFFAOYSA-L zinc;butoxymethanedithioate Chemical compound [Zn+2].CCCCOC([S-])=S.CCCCOC([S-])=S NEYNBSGIXOOZGZ-UHFFFAOYSA-L 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
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- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/203—Solid polymers with solid and/or liquid additives
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- 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
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
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- 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
-
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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Applications Claiming Priority (4)
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| US5656697P | 1997-08-21 | 1997-08-21 | |
| US6/056,566 | 1997-08-21 | ||
| US06/056,566 | 1997-08-21 | ||
| PCT/US1998/017391 WO1999009036A1 (en) | 1997-08-21 | 1998-08-21 | Blocked mercaptosilane coupling agents for filled rubbers |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020067013055A Division KR100825539B1 (ko) | 1997-08-21 | 1998-08-21 | 차단된 메르캅토실란의 제조 방법 |
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| KR20000068795A KR20000068795A (ko) | 2000-11-25 |
| KR100674059B1 true KR100674059B1 (ko) | 2007-01-25 |
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| KR1020067013055A Expired - Fee Related KR100825539B1 (ko) | 1997-08-21 | 1998-08-21 | 차단된 메르캅토실란의 제조 방법 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1020067013055A Expired - Fee Related KR100825539B1 (ko) | 1997-08-21 | 1998-08-21 | 차단된 메르캅토실란의 제조 방법 |
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| PT (1) | PT958298E (cg-RX-API-DMAC7.html) |
| WO (1) | WO1999009036A1 (cg-RX-API-DMAC7.html) |
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- 1998-08-21 WO PCT/US1998/017391 patent/WO1999009036A1/en not_active Ceased
- 1998-08-21 CN CNB988015625A patent/CN100376585C/zh not_active Expired - Lifetime
- 1998-08-21 JP JP51363999A patent/JP2001505225A/ja not_active Withdrawn
- 1998-08-21 KR KR1019997003423A patent/KR100674059B1/ko not_active Expired - Lifetime
- 1998-08-21 EP EP06004389A patent/EP1679315A1/en not_active Withdrawn
- 1998-08-21 US US09/284,841 patent/US6414061B1/en not_active Expired - Lifetime
- 1998-08-21 CN CNA2007101424877A patent/CN101139355A/zh active Pending
- 1998-08-21 AU AU89179/98A patent/AU8917998A/en not_active Abandoned
- 1998-08-21 EP EP98941025A patent/EP0958298B2/en not_active Expired - Lifetime
- 1998-08-21 ES ES02019729.9T patent/ES2458563T3/es not_active Expired - Lifetime
- 1998-08-21 DE DE69814353T patent/DE69814353T3/de not_active Expired - Lifetime
- 1998-08-21 KR KR1020067013055A patent/KR100825539B1/ko not_active Expired - Fee Related
- 1998-08-21 EP EP02019729.9A patent/EP1270581B1/en not_active Expired - Lifetime
- 1998-08-21 PT PT98941025T patent/PT958298E/pt unknown
- 1998-08-21 AT AT98941025T patent/ATE239737T1/de not_active IP Right Cessation
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1999
- 1999-02-05 US US09/245,454 patent/US6204339B1/en not_active Expired - Lifetime
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2001
- 2001-11-09 US US09/986,513 patent/US6528673B2/en not_active Expired - Lifetime
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2003
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2004
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2006
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