JP4895478B2 - 硫化ポリイソブチレンベースの摩耗・酸化防止剤 - Google Patents
硫化ポリイソブチレンベースの摩耗・酸化防止剤 Download PDFInfo
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- JP4895478B2 JP4895478B2 JP2004022131A JP2004022131A JP4895478B2 JP 4895478 B2 JP4895478 B2 JP 4895478B2 JP 2004022131 A JP2004022131 A JP 2004022131A JP 2004022131 A JP2004022131 A JP 2004022131A JP 4895478 B2 JP4895478 B2 JP 4895478B2
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- polyisobutylene
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- sulfur
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- 229920002367 Polyisobutene Polymers 0.000 title claims description 91
- 239000003963 antioxidant agent Substances 0.000 title description 6
- 230000003078 antioxidant effect Effects 0.000 title description 4
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- -1 methylvinylidene Chemical class 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 65
- 229910052717 sulfur Inorganic materials 0.000 claims description 61
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 59
- 239000011593 sulfur Substances 0.000 claims description 57
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- 238000006243 chemical reaction Methods 0.000 claims description 41
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- 229910052698 phosphorus Inorganic materials 0.000 claims description 16
- 239000011574 phosphorus Substances 0.000 claims description 16
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- 229910052796 boron Inorganic materials 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 4
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
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- 125000001931 aliphatic group Chemical group 0.000 description 10
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- 238000005987 sulfurization reaction Methods 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 239000002562 thickening agent Substances 0.000 description 6
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- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
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- 150000002500 ions Chemical class 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- LZENMJMJWQSSNJ-UHFFFAOYSA-N 3H-1,2-dithiole-3-thione Chemical class S=C1C=CSS1 LZENMJMJWQSSNJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- KXPHJGWRCICEDH-UHFFFAOYSA-N 1-sulfanylidene-3h-dithiole Chemical compound S=S1SCC=C1 KXPHJGWRCICEDH-UHFFFAOYSA-N 0.000 description 2
- TUFZRYOCZCLYJO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-methylideneheptane Chemical compound CC(C)(C)CC(=C)CC(C)(C)C TUFZRYOCZCLYJO-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- CXYRUNPLKGGUJF-OZVSTBQFSA-M pamine Chemical compound [Br-].C1([C@@H](CO)C(=O)OC2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-OZVSTBQFSA-M 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- OHRVKCZTBPSUIK-UHFFFAOYSA-N tridodecyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OCCCCCCCCCCCC OHRVKCZTBPSUIK-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- SVETUDAIEHYIKZ-IUPFWZBJSA-N tris[(z)-octadec-9-enyl] phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCCOP(=O)(OCCCCCCCC\C=C/CCCCCCCC)OCCCCCCCC\C=C/CCCCCCCC SVETUDAIEHYIKZ-IUPFWZBJSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- KCVNDCFWUCRGBP-UHFFFAOYSA-N trizinc [butyl(phenyl)-lambda4-sulfanylidene]-dioxido-sulfido-lambda5-phosphane Chemical compound C(CCC)S(=P([S-])([O-])[O-])C1=CC=CC=C1.[Zn+2].C(CCC)S(=P([S-])([O-])[O-])C1=CC=CC=C1.[Zn+2].[Zn+2] KCVNDCFWUCRGBP-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- ZBDJNBFTEIUHPK-UHFFFAOYSA-L zinc;dihexoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCOP([S-])(=S)OCCCCCC.CCCCCCOP([S-])(=S)OCCCCCC ZBDJNBFTEIUHPK-UHFFFAOYSA-L 0.000 description 1
- GBEDXBRGRSPHRI-UHFFFAOYSA-L zinc;octoxy-octylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCCOP([O-])(=S)SCCCCCCCC.CCCCCCCCOP([O-])(=S)SCCCCCCCC GBEDXBRGRSPHRI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/02—Sulfurised compounds
- C10M135/04—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/42—Phosphor free or low phosphor content compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/10—Chemical after-treatment of the constituents of the lubricating composition by sulfur or a compound containing sulfur
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
前述したHR PIBの商業生産的方法は、(i)主として、C8H16乃至C28H56のオリゴマー(平均C14H28)を含み、(ii)約200の比較的低い平均分子量を示し、そして(iii)2−メチルビニリデンを少なくとも約25%の量で含む、HR PIB蒸留副生成物を生じることが、当該分野の熟練者によって一般に知られている。この低分子量の蒸留副生成物は、全HR PIB製造の数パーセントに達するが、あまり価値が無く、一般には燃料製品として販売されている。このため、化学工業ではHR PIB蒸留副生成物の価値ある使用を開発することが求められている。本発明は、好ましくはHR PIB蒸留副生成物またはその留分を用いた、硫化オレフィンおよび別のポリイソブチル−1,2−ジチオ−ル−4−シクロペンテン−3−チオン組成物及びその誘導体の製造方法を提供することによって、この要求を満たすものである。
HR PIBの硫化には、任意の適当な硫黄源(硫黄含有化合物)を使用することができる。硫黄元素、硫化水素、二酸化硫黄、水和硫化ナトリウムは、よく知られていて市販もされている。硫黄元素を使用することが好ましく、硫黄元素を加熱して溶融状態にして反応速度を促進し、そして一硫化物及び多硫化物、メルカプト成分を含むジチオール誘導体の形成を最小にすることができる、しかしながら、後者は更に分解して、本発明のポリイソブチル−1,2−ジチオ−ル−4−シクロペンテン−3−チオン組成物になることができる。
本発明の潤滑油組成物は、メチルビニリデン異性体を少なくとも40%含み、数平均分子量が約150乃至約600の範囲にある高反応性ポリイソブチレンを、硫黄原料を用いて約175℃以上の反応温度で硫化することによって製造した組成物を、潤滑粘度の油(基油)と単にブレンドまたは混合することにより都合よく製造することができる。潤滑粘度の油は、得られた一般式Iで代表される本発明のポリイソブチル−1,2−ジチオール−4−シクロペンテン−3−チオン組成物と混合してもよい。また、本発明の化合物は、所望の濃度の添加剤を含む潤滑油組成物のブレンドを容易にするために、濃縮物またはパッケージとして、その他各種の添加剤と一緒に適当な比率でプレブレンドすることもできる。摩耗防護をもたらし、そして油溶性でかつ所望とする完成潤滑油中の他の添加剤と混合性であるような濃度で、本発明の化合物を基油とブレンドする。この場合の混合性とは一般に、本発明の化合物が、適用可能な処理速度で油溶性であるのと同様に、他の添加剤も標準条件下で沈殿させないことを意味する。潤滑油配合物のある化合物に対する好適な油溶性/混合性の範囲は、当該分野の一般的な熟練者により日常溶解度試験法を用いて決定することができる。例えば、環境条件(約20℃〜25℃)で配合した潤滑油組成物からの沈殿は、油組成物からの実際の沈殿、あるいは不溶性の蝋粒子が形成された証拠となる「濁った」溶液の配合によって測定することができる。
イソブチレンと硫化水素および硫黄元素との反応からの多硫化飽和ジアルキルは、次の反応式により表すことができる:
反応条件、反応物充填温度を変えることにより、あるいは触媒を用いることにより、もっと複雑なアルキル−アルケニル型多硫化物の混合物を生成させることができる。生成したアルキル−アルケニル生成物は下記式で表される:
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硫化物構造 分子イオン(m/z) 重量%
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化6 140 2〜5
化7 176 15〜20
化8 208 25〜30
化9 230 1〜5
化10 262 3〜10
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メチルビニリデン2%以下で、約45%の2,2,6,6−テトラメチル−4−メチレンヘプタンと約53%の2,2,4,6,6−ペンタメチル−3−ヘプテンを含む、一般に市販されているトリイソブチレン(TCIアメリカ)を、硫黄2.5モル当量で処理した。トリイソブチレン362.9g(2.16モル)、および硫黄173g(5.4モル)を、実施例2に記載する条件と同様の条件下で反応させた。約180℃(還流)で約6時間経た後、硫化生成物の収率は4%であり、GCMSでは、1%以下の4,5−ジアルキル−1,2−ジチオ−ル−4−シクロペンテン−3−チオンが含まれていた。ジチオールチオンのアルキル基は、質量スペクトルで実証されてt−ブチルとネオペンチルであり、また質量スペクトルには分子イオン260m/z、および断片イオン57、189、203、227及び245m/zも含まれていた。
[実施例1] 高メチルビニリデンC8−C32ポリイソブテン留分からのポリイソブチル−1,2−ジチオ−ル−4−シクロペンテン−3−チオン「PDCT」混合物の製造
平均分子量が178で、約74%のメチルビニリデン含量を有する(そして、各オリゴマーの重量留分が、ガスクロマトグラフィーと核磁気共鳴分光法で確認したところ、C8H16約16重量%、C12H24約41重量%、C16H32約26重量%、C20H40約11重量%、C24H48約4重量%、及びC28H56約2重量%、そしてC32H64痕跡量である)高メチルビニリデン含量低分子量PIB1904.8g(10.7モル)、および硫黄元素1017.5gを、5リットルステンレス鋼製オートクレーブに入れた。オートクレーブを窒素で洗い流した後、密閉した。反応物を約2時間かけて撹拌しながら200℃まで加熱した。次いで、オートクレーブ内の圧力が200psiaを越えないような自己加熱圧力下で、温度を200と220℃の間に3.5時間維持した。反応を周囲温度まで冷却し、そしてオートクレーブに苛性アルカリスクラバーで穴を開けた。暗赤色の油2440gをペンタンで希釈し、濾過し、次いでストリッピングして溶媒を除去した。生成物は、LECO SC-32硫黄分析装置を用いてASTM D1552により分析したところ、硫黄29.3%を含み、またGCMSで確認したところ、一般式IのPDCT49.5%を含んでいた。
蒸留してC8異性体を除去した、平均分子量が198で、73%のメチルビニリデン含量を有する低分子量ポリブテン497.4g(2.51モル)、および硫黄201gを、機械撹拌器、加熱マントル、熱電対、温度調節器、還流冷却器、窒素流入口および苛性アルカリスクラバーを備えたガラス製三つ口丸底フラスコ内で、窒素雰囲気下で加熱し撹拌した。穏やかな窒素流を継続的に容器とスクラバーに通した。全体で約1時間かけて反応物を約180℃に加熱して還流した後ゆっくりと200℃まで加熱し、200℃で約20分間維持し、次いで220℃で2.5時間加熱した。室温まで冷却した後、生成物をヘプタン400mlで希釈し、そして珪藻土で濾過した。溶媒を除去して、硫黄23.8%を含む暗赤色の粘性油447.4gを得た。
C16異性体を含み、約66重量%のメチルビニリデンを含むポリイソブテンからの蒸留留分を、実施例2と同様の方法で硫化した。この実施例の生成物は、ガスクロマトグラフィー質量分光法(GCMS)分析により確認された。下記の表は、分子構造または実験式、観測された分子イオンの質量電荷比、および主要な組成物の重量パーセントを含む。
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硫化物 分子イオン(m/z) 重量%
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C16H28S 252 1.2
C16H32S2 288 1.5
C16H28S2 284 3.2
化11 316 38.3
(C16H33)2S2 514 15.4
(C16H33)2S3 546 3.1
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実施例1の試料を、HPLCによりシリカゲルカラムで精製した。カラムをヘキサンで洗い流して、未反応のHR PIBおよびPDCT以外の硫黄含有化合物を取り除いた。溶離剤としてヘキサン:酢酸エチルが9:1のものを用いて、所望のジチオールチオンを含む画分を集めた。一連の画分から溶媒を除去して、GCによるとC8、12、16、20PDCTを88.4重量パーセント含む生成物を得た、生成物は硫黄約33%を含んでいた。
以下の実施例では、耐摩耗性、極圧性および酸化特性について試験した。基準線配合物として配合油を用いた。この配合油は、潤滑油と一般的な量の特別な目的の添加剤とからなり、これには次のものが含まれた:粘度グレード5W20のII種基油、分子量2300の後処理エチレンカーボネートビスコハク酸イミド分散剤3重量%、TBN17の低過塩基性カルシウムスルホネート1重量%、TBN250の高過塩基性カルシウムフェネート2.4重量%、第二級アルコールZnDTP0.6重量%、ジフェニルアミン酸化防止剤0.5重量%、および粘度指数向上剤。リン量が潤滑油組成物の全リン量に基づき約0.08重量%であるので、この配合物を低リン基準物と呼ぶことにする。
四球摩耗試験
ASTM D−4172(四球摩耗)と同様の方法で、以下に述べるように、四球摩耗試験を行った。実施例1、実施例3に従って製造したポリイソブチル−1,2−ジチオ−ル−4−シクロペンテン−3−チオン化合物、および市販の硫化イソブチレン(比較例A)の試料を、基準線の低リン自動車クランクケースエンジン油に、下記表に従って上記配合物に対して0.2乃至0.25重量パーセントの処理比でトップ処理した。これらの配合試験油を、鋼ボールベアリングを含む酸化浴中で160℃で、油中に15L/時の空気流を泡立たせながら、48時間老化させた。これらの老化した油を、四球摩耗試験機で100C6鋼球を用いて試験し、1500回転/分で、10kgから始めて増分10kgとして9段階で90kgの荷重を掛けた。荷重アームの移動量から摩耗指数を算出した。
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試料 処理比(%S基準) 摩耗指数
──────────────────────────
基準物(基準線) 0 179
実施例11 0.059 82
実施例31 0.039 165
比較例A1 0.054 331
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1:基準物の油に添加した
ファレックス極圧摩耗試験
実施例2、実施例3の生成物及び比較例Aについて、ファレックス極圧摩耗試験機で試験した。この試験は、高接触圧条件下で油の荷重負担能力を評価するために使用される。試料を上記基準物に、0.20乃至0.25重量パーセント%処理でトップ処理した。これらの配合試験油は予備老化させなかった。250ポンド荷重で5分間の試運転に続いて、室温で400ポンド荷重、ピンの回転290回転/分で1時間、ファレックス試験を行った。試験の結果は、試験の終了時のピンの重量損失として、あるいは試験の終了前に部品が融着したならば焼付きとして示され、表4に示す。比較例Aと実施例2の生成物の両方のトップ処理は基準線の荷重能力を改善したので、焼付きが生じなかった。
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試料 処理比(%S基準) 焼付き(有/無) 重量損失(mg)
───────────────────────────────
基準物 0% 有り n/a
(基準線)
実施例21 0.060 無し 35
実施例31 0.039 有り n/a
比較例A1 0.054 無し 18.5
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1:基準物の油に添加した
1997年5月13−15日、スウェーデン、ゴーテゴルグの第5回CEC国際シンポジウムで、自動車燃料及び潤滑剤の性能評価について提出された、B.-R ホーン、外著、「高EP性能のギヤ潤滑剤のためのFZGギヤ試験装置でのスカッフィング荷重能力試験」(B.-R Hohn et al, Scuffing load capacity test in the FZG gear test rig for gear lubricants with high EP performance)に記載の方法に従って、「衝撃荷重」条件を変更したFZGギヤ試験装置で、実施例1、2及び3の生成物と比較例A及びBについて試験した。FZG「衝撃荷重」ギヤ試験は、本発明の化合物の耐スカッフィング特性を評価するために行った。実施例1乃至3の生成物と二種類の市販の硫化イソブチレン、比較例A及びB。FZGギヤ試験では、シェブロン600ニュートラル油に添加剤を硫黄0.9%で添加したものを用いた。ASTM D5182には、FZG荷重段階試験の標準的方法と装置が詳しく述べられている。衝撃荷重法では、荷重段階1から始めてギヤの歯表面10mmがスカッフィングを受けるまで、段階的にギヤに荷重を掛けた。表5は、この破損が生じた段階として示した試験結果を含む。
表 5 FZG「衝撃荷重」ギヤ試験
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試料 試験結果−破損発生段階
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実施例1 11
実施例2 11
実施例3 8
比較例A 11
比較例B 11
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ギヤ用潤滑剤配合物に用いられる本発明の化合物を評価するために、L−42後差動車軸試験を行った。実施例1乃至3の生成物、比較例A乃至Bについて、高速及び衝撃条件下で、DANAモデル44ハイポイド後車軸を用いて、ASTM公報STP 512Aに記載のL42法により、耐スコーリング特性の試験をした。表6の試験結果は、ピニオンとリングギヤのスコーリングを受けた面積、および参照油配合物との比較に基づく合格/不合格である。最低濃度の市販品が合格する硫黄量に基づいて種々の濃度で試料を試験した。合格/不合格の基準として、リングとピニオンギヤのスコーリングの量が関連する合格参照油試験での量よりも少ないことが要求される。合格するために比較例Aでは、硫黄1.1%を与えるのに十分な量の添加剤を必要とした。この硫黄の濃度では、実施例1及び実施例3の組成物は参照油と同様の性能を示さなかった。しかしながら、硫黄濃度1.1以上、1.8以下で実施例1及び3の組成物は合格すると考えられる。
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試料 処理比 スコーリング面積(%) 結果
(%S基準) リング ピニオン (合格/不合格)
───────────────────────────────
比較例A 1.1 11 12 合格
実施例1 1.1 27 33 不合格
実施例3 1.2 33 39 不合格
比較例B 1.7 14 21 合格
実施例2 1.8 5 6 合格
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実施例1の生成物及び実施例4の生成物について、
PCSインスツルメント社、英国ロンドンのミニ−トラクションマシン(MTM)摩擦摩耗試験機を用いて評価を行った。PCSインスツルメントの52100鋼の研磨ディスクと、ピンの代わりにファレックス社の同じく52100鋼の0.25インチ静止ボールベアリングとを用いて、ピン・オン・ディスク式で作動するようにMTM試験機を設定した。荷重0.1ニュートン、滑り速度2000mm/sで5分間の試運転に続いて、荷重7ニュートン、滑り速度200mm/sで、100℃で40分間試験を行った。表7の試験結果は、従来法により光学顕微鏡を用いて測定したところ、ボールベアリングに発生していた摩耗痕を示す。4回の試験運転の平均摩耗痕を報告する。比較のために、市販のジチオリン酸亜鉛の試験結果を含む。実施例4の生成物は、この試験の条件下で優れた摩耗防護をもたらした。実施例1の生成物は、シェブロン100ニュートラル油中で3種類の異なる濃度で試験し、実施例4の生成物は、実施例1に対して1.9重量%の等しい硫黄量で試験した。
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試料 100ニュートラル油 摩耗痕(μm)
中の添加剤重量%
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実施例1 0.5重量% 575
実施例1 1.0重量% 478
実施例1 1.9重量% 228
実施例4 1.9重量% 156
ZnDTP2 1.4重量% 172
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ZnDTP2は、第二級アルコールジチオリン酸亜鉛(sec−
ブタノールとメチルイソブチルカルビノールから)であり、
リン量で約0.2重量%の濃度で使用した。
E. S. ヤマグチ、外、トライポロジー・トランスアクション(E.S. Yamaguchi et al. Tribology Transactions)第42(4)巻、P.895−901、1999年に記載の大量潤滑油酸化ベンチ試験にて、実施例2の生成物の酸化研究を行った。この試験では、金属触媒を加えたある容積の油による酸素消費の速度を一定の圧力と温度でモニタし、表8に報告した試験結果では171℃、2psigO2でモニタした。試料25gで酸素消費250mlに要する時間、および酸素消費速度の著しい増加が観測された時刻を、基準線配合物、および実施例2の生成物0.5重量パーセントでトップ処理した基準線配合物について、下記表に報告する。
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試験パラメータ 配合物 時間(時)
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250mlO2消費/25g 基準線 17.3
基準線+実施例2 21.7
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増加O2消費 基準線 13.1
基準線+実施例2 28.6
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Claims (27)
- メチルビニリデン異性体を少なくとも40%含み、数平均分子量が150乃至600の範囲にある高反応性ポリイソブチレンを、硫黄源を用いて、175℃以上の反応温度で硫化することにより製造された組成物。
- ポリイソブチレン部がC8H16乃至C32H64のオリゴマーの混合物から選ばれる請求項1に記載の組成物。
- ポリイソブチレンが、C8H16が5重量%乃至20重量%、C12H24が35重量%乃至55重量%、C16H32が20重量%乃至30重量%、C20H40が8重量%乃至15重量%、C24H48が2重量%乃至8重量%、C28H56が0.5重量%乃至2重量%、およびC32H64が2重量%以下の各成分から構成される請求項2に記載の組成物。
- 反応が大気圧またはそれ以下で行なわれる請求項1に記載の組成物。
- ポリイソブチレン部がC12H24乃至C32H64のオリゴマーの混合物から選ばれる請求項4に記載の組成物。
- ポリイソブチレン部が40乃至95%のメチルビニリデン異性体を含む請求項1に記載の組成物。
- ポリイソブチレン部が60乃至85%のメチルビニリデン異性体を含む請求項6に記載の組成物。
- ポリイソブチレンの数平均分子量が150乃至240の範囲にある請求項1に記載の組成物。
- ポリイソブチレンの数平均分子量が175乃至225の範囲にある請求項8に記載の組成物。
- R1がメチルであり、そしてXが硫黄である請求項10に記載の化合物。
- R1が水素であり、そしてXが硫黄である請求項10に記載の化合物。
- mが少なくとも2である請求項10に記載の化合物。
- mが1〜6の整数である請求項10に記載の化合物。
- mが1〜5の整数である請求項14に記載の化合物。
- 硫化オレフィン組成物を製造する方法であって、メチルビニリデン異性体を少なくとも50%含み、数平均分子量が150乃至600の範囲にあるポリイソブチレンを、硫黄源と、175℃以上の反応温度で反応させることからなる製造方法。
- ポリイソブチレン部がC8H16乃至C32H64のオリゴマーの混合物から選ばれる請求項16に記載の方法。
- ポリイソブチレンが、C8H16が5重量%乃至20重量%、C12H24が35重量%乃至55重量%、C16H32が20重量%乃至30重量%、C20H40が8重量%乃至15重量%、C24H48が2重量%乃至8重量%、C28H56が0.5重量%乃至2重量%、およびC32H64が2重量%以下である各成分から構成される請求項17に記載の方法。
- ポリイソブチレン部がC12H24乃至C32H64のオリゴマーの混合物から選ばれる請求項16に記載の方法。
- ポリイソブチレン部が少なくとも70%のメチルビニリデン異性体を含む請求項16に記載の方法。
- ポリイソブチレンの数平均分子量が150乃至240の範囲にある請求項16に記載の方法。
- ポリイソブチレンの数平均分子量が175乃至225の範囲にある請求項21に記載の方法。
- 請求項16に従って製造された生成物。
- 請求項18に従って製造された生成物。
- 下記の成分を含む潤滑油組成物:
a)潤滑粘度の油、
b)メチルビニリデン異性体を少なくとも40%含み、数平均分子量が150乃至600の範囲にあるポリイソブチレンを、硫黄源と、175℃以上の反応温度で反応させることにより製造された硫化オレフィン、
c)無灰分散剤、
d)清浄剤、
e)ジアルキルジチオリン酸金属塩。 - 下記の成分を含むギヤ用潤滑油組成物:
a)主要量の潤滑粘度の油、
b)メチルビニリデン異性体を少なくとも40%含み、数平均分子量が150乃至600の範囲にあるポリイソブチレンを、硫黄原料と、175℃以上の反応温度で反応させることにより製造された硫化オレフィンを、硫黄量で0.5乃至8.0重量%、
c)極圧剤および耐摩耗剤から選ばれる少なくとも一種の油溶性リン含有化合物を、リン量で0.05乃至5.0重量%、
d)ホウ酸アルカリ金属塩又はその水和物を、ホウ素量で0.04乃至1.0重量%。 - 下記の添加成分のうちの少なくとも一種を更に含む請求項26に記載のギヤ用潤滑油組成物:
e)少なくとも一種の無灰分散剤を、該潤滑油組成物の重量に基づき0.1乃至5重量%、
f)少なくとも一種の銅腐食防止剤を、該潤滑油組成物の重量に基づき0.1乃至0.8重量%、
g)少なくとも一種の消泡剤を、該潤滑油組成物の重量に基づき0.01乃至0.1重量%、
h)少なくとも一種のさび止め剤を、該潤滑油組成物の重量に基づき0.01乃至0.1重量%。
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JP4895478B2 true JP4895478B2 (ja) | 2012-03-14 |
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JP2004022131A Expired - Lifetime JP4895478B2 (ja) | 2003-01-30 | 2004-01-29 | 硫化ポリイソブチレンベースの摩耗・酸化防止剤 |
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US (2) | US6884855B2 (ja) |
EP (3) | EP1443061B2 (ja) |
JP (1) | JP4895478B2 (ja) |
CA (1) | CA2454714C (ja) |
DE (2) | DE60334331D1 (ja) |
SG (1) | SG137660A1 (ja) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6884855B2 (en) | 2003-01-30 | 2005-04-26 | Chevron Oronite Company Llc | Sulfurized polyisobutylene based wear and oxidation inhibitors |
US20040214729A1 (en) | 2003-04-25 | 2004-10-28 | Buitrago Juan A. | Gear oil composition having improved copper corrosion properties |
JP2005008695A (ja) * | 2003-06-17 | 2005-01-13 | Nippon Oil Corp | 潤滑油組成物 |
US20050059561A1 (en) * | 2003-09-17 | 2005-03-17 | Nubar Ozbalik | Power transmitting fluids and additive compositions |
US7648948B2 (en) * | 2005-04-08 | 2010-01-19 | Exxonmobil Chemical Patents Inc. | Additive system for lubricants |
US20060264341A1 (en) * | 2005-05-20 | 2006-11-23 | Culley Scott A | Transmission composition |
ATE510903T1 (de) * | 2005-05-20 | 2011-06-15 | Infineum Int Ltd | Verwendung von schmierölzusammensetzungen zur verschleissreduzierung von mit drehendem zapfer versehenen personenkraftwagenmotoren |
US20070142247A1 (en) * | 2005-12-15 | 2007-06-21 | Baillargeon David J | Method for improving the corrosion inhibiting properties of lubricant compositions |
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JP5076112B2 (ja) * | 2007-03-13 | 2012-11-21 | 昭和シェル石油株式会社 | ディーゼルエンジン用潤滑油組成物 |
JP5075449B2 (ja) * | 2007-03-30 | 2012-11-21 | Jx日鉱日石エネルギー株式会社 | 銀含有材料と接触する潤滑油組成物 |
WO2009010441A2 (de) | 2007-07-16 | 2009-01-22 | Basf Se | Synergistische mischung |
JP5379361B2 (ja) * | 2007-08-08 | 2013-12-25 | 出光興産株式会社 | 耐摩耗剤、潤滑剤用添加剤組成物及び潤滑油組成物 |
US20090318319A1 (en) * | 2008-06-23 | 2009-12-24 | Afton Chemical Corporation | Friction modifiers for slideway applications |
US20100152073A1 (en) | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
US20100152072A1 (en) | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
US20100152074A1 (en) | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
CA2957073C (en) * | 2014-08-06 | 2023-08-29 | The Lubrizol Corporation | Industrial gear lubricant additive package with biodegradable sulfur component |
CN105524194B (zh) * | 2014-10-22 | 2017-11-03 | 中国石油化工股份有限公司 | 一种4‑聚异丁烯基‑1,2‑二硫代‑4‑环戊烯‑3‑硫酮的制备方法 |
EP3231820A1 (en) * | 2016-04-15 | 2017-10-18 | ARLANXEO Canada Inc. | Polymer compositions having a halo-containing polymer with a multi-functional phosphine linkage |
US10704009B2 (en) | 2018-01-19 | 2020-07-07 | Chevron Oronite Company Llc | Ultra low ash lubricating oil compositions |
US20190276565A1 (en) * | 2018-03-12 | 2019-09-12 | Exxonmobil Research And Engineering Company | Functionalized polyalphaolefins |
WO2020190859A1 (en) | 2019-03-20 | 2020-09-24 | Basf Se | Lubricant composition |
CN113583743B (zh) * | 2021-08-10 | 2022-08-30 | 山东阿莫索能源科技有限公司 | 一种拖轮轴瓦油及其制备方法 |
CN118339265A (zh) * | 2021-11-16 | 2024-07-12 | 雪佛龙日本有限公司 | 用于电动车辆的润滑油组合物 |
US11572524B1 (en) | 2022-05-25 | 2023-02-07 | Afton Chemical Corporation | Lubricating composition for differential and gear fluids |
US11873461B1 (en) | 2022-09-22 | 2024-01-16 | Afton Chemical Corporation | Extreme pressure additives with improved copper corrosion |
US11795412B1 (en) | 2023-03-03 | 2023-10-24 | Afton Chemical Corporation | Lubricating composition for industrial gear fluids |
Family Cites Families (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE869799C (de) † | 1940-05-08 | 1953-03-09 | Bruno Boettcher Dr | Verfahren zur Herstellung schwefelhaltiger organischer Verbindungen (5-Thion-1, 2-dithiole) |
US2337473A (en) | 1940-09-28 | 1943-12-21 | Texas Co | Sulphurization of hydrocarbons |
US2535706A (en) | 1947-03-07 | 1950-12-26 | Gulf Research Development Co | 4-methyl-1,2-dithia-4-cyclopentene-3-thione |
US2535705A (en) | 1947-03-07 | 1950-12-26 | Gulf Research Development Co | 4-neopentyl-1,2-dithia-4-cyclopentene-3-thione and 4-methyl-5-tertiary-butyl-1,2-dithia-4-cyclopentene-3-thione |
US2658900A (en) † | 1951-02-15 | 1953-11-10 | Gulf Research Development Co | Sulfurization of di-isobutylene |
BE510012A (ja) | 1951-03-29 | |||
US3000822A (en) | 1957-01-22 | 1961-09-19 | Lubrizol Corp | Phosphorodithioate inhibitors |
US2995569A (en) | 1957-05-02 | 1961-08-08 | Socony Mobil Oil Co Inc | Process for preparation of alkyl-1, 2-dithiole-3-thiones |
US3151075A (en) | 1961-03-03 | 1964-09-29 | Lubrizol Corp | Oxidation-resistant lubricating composition |
US3235502A (en) | 1962-06-11 | 1966-02-15 | Socony Mobil Oil Co Inc | Foam-inhibited oil compositions |
US3235499A (en) | 1962-06-11 | 1966-02-15 | Socony Mobil Oil Co Inc | Foam-inhibited oil compositions |
US3235498A (en) | 1962-06-11 | 1966-02-15 | Socony Mobil Oil Co Inc | Foam-inhibited oil compositions |
US3235501A (en) | 1962-06-11 | 1966-02-15 | Socony Mobil Oil Co Inc | Foam-inhibited oil compositions |
US3385791A (en) | 1965-03-22 | 1968-05-28 | Standard Oil Co | Lubricant oil composition |
US3345380A (en) | 1965-03-29 | 1967-10-03 | Shell Oil Co | Trithione production |
US3364232A (en) | 1966-01-05 | 1968-01-16 | Chevron Res | Sulfur containing pseudoaromatic detergents |
US3427246A (en) * | 1966-09-28 | 1969-02-11 | Chevron Res | Trithione-tervalent phosphorus reaction product and lubricating oil containing same |
GB1162443A (en) | 1966-11-10 | 1969-08-27 | Mobil Oil Corp | Additives for Organic Lubricants. |
US3364262A (en) * | 1966-11-25 | 1968-01-16 | Universal Oil Prod Co | Polyhydroxyalkylpolyamines |
GB1195749A (en) | 1966-12-19 | 1970-06-24 | Lubrizol Corp | Sulfur-Containing Cycloaliphatic Reaction Products and their use in Lubricant Compositions |
US3703504A (en) | 1970-01-12 | 1972-11-21 | Mobil Oil Corp | Process for producing sulfurized olefins |
US3697221A (en) | 1970-01-19 | 1972-10-10 | Petrolite Corp | Use of thionium derivatives as corrosion inhibitors |
US3703505A (en) | 1970-08-31 | 1972-11-21 | Mobil Oil Corp | Preparation of sulfurized olefins |
US3796661A (en) | 1971-07-19 | 1974-03-12 | Texaco Inc | Sulfurized triisobutylene |
US3753908A (en) | 1971-08-30 | 1973-08-21 | Chevron Res | Oxidation inhibited lubricating oil compositions with extreme pressure properties |
US3873454A (en) | 1974-03-22 | 1975-03-25 | Mobil Oil | Lubricant composition |
FR2300793A1 (fr) | 1975-02-17 | 1976-09-10 | Orogil | Nouvelles compositions lubrifiantes |
US4119550A (en) | 1975-03-21 | 1978-10-10 | The Lubrizol Corporation | Sulfurized compositions |
US4344854A (en) | 1975-03-21 | 1982-08-17 | The Lubrizol Corporation | Sulfurized compositions |
US4119549A (en) | 1975-03-21 | 1978-10-10 | The Lubrizol Corporation | Sulfurized compositions |
CA1064463A (en) | 1975-03-21 | 1979-10-16 | Kirk E. Davis | Sulfurized compositions |
GB1560667A (en) | 1976-09-24 | 1980-02-06 | Cooper & Co Ltd Edwin | Sulphurize olefins and their use as lubricant additives |
DE2702604C2 (de) | 1977-01-22 | 1984-08-30 | Basf Ag, 6700 Ludwigshafen | Polyisobutene |
GB2016479B (en) | 1978-03-15 | 1982-09-02 | Bp Chem Int Ltd | Sulphurised polybutens |
US4158633A (en) | 1978-03-30 | 1979-06-19 | Edwin Cooper, Inc. | Lubricating oil |
US4194980A (en) | 1978-12-15 | 1980-03-25 | Mobil Oil Corporation | Sulfurized olefin lubricant additives and compositions containing same |
US4240958A (en) | 1978-12-20 | 1980-12-23 | Mobil Oil Corporation | Process of preparing sulfurized olefins |
US4377527A (en) | 1981-03-09 | 1983-03-22 | Standard Oil Company (Indiana) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates |
GB8329082D0 (en) | 1983-11-01 | 1983-12-07 | Bp Chem Int Ltd | Low molecular weight polymers of 1-olefins |
US4495075A (en) | 1984-05-15 | 1985-01-22 | Chevron Research Company | Methods and compositions for preventing the precipitation of zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group |
ZA862362B (en) | 1985-04-08 | 1987-11-25 | Mobil Oil Corp | Sulfurized olefins |
US4778906A (en) | 1986-08-28 | 1988-10-18 | Texaco Inc. | Process for the preparation of zinc dialkyldithiophosphate |
EP0275651A1 (en) * | 1987-01-02 | 1988-07-27 | Petrolite Corporation | Carbon dioxide corrosion inhibiting composition and method of use thereof |
US4797219A (en) * | 1987-04-24 | 1989-01-10 | Exxon Chemical Patents Inc. | Novel dispersants for oleaginous compositions |
FR2630449B1 (fr) | 1988-04-26 | 1992-03-20 | Bp Chimie Sa | Nouveau produit d'addition entre un thiol et un polybutene comportant une double liaison carbone-carbone et procede de preparation |
US5135670A (en) | 1990-06-22 | 1992-08-04 | Mobil Oil Corporation | Sulfurized olefin extreme pressure/antiwear additives and compositions thereof |
US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
US5286823A (en) * | 1991-06-22 | 1994-02-15 | Basf Aktiengesellschaft | Preparation of highly reactive polyisobutenes |
CA2076140C (en) * | 1991-08-21 | 2002-02-26 | Andrew G. Papay | Oil additive concentrates and lubricants of enhanced performance capabilities |
US5338468A (en) | 1992-10-05 | 1994-08-16 | Mobil Oil Corporation | Sulfurized olefins |
US5368758A (en) | 1992-10-13 | 1994-11-29 | The Lubrizol Corporation | Lubricants, greases and aqueous fluids containing additives derived from dimercaptothiadiazoles |
IL107927A0 (en) * | 1992-12-17 | 1994-04-12 | Exxon Chemical Patents Inc | Oil soluble ethylene/1-butene copolymers and lubricating oils containing the same |
US5348927A (en) * | 1993-03-01 | 1994-09-20 | Scientific Design Company, Inc. | Treatment for virgin phosphorous/vanadium oxidation catalysts |
FR2706572B1 (fr) | 1993-06-11 | 1995-08-25 | Presto Robinets Sa | Dispositif d'assemblage à inviolabilité renforcée pour robinet à fermeture temporisée. |
US5397486A (en) | 1993-07-30 | 1995-03-14 | Chevron Chemical Company | Lubricating oil compositions for railroad diesel engines |
US5448000A (en) | 1994-02-17 | 1995-09-05 | New Mexico Tech Research Foundation | End-quenching the living polymerization of isobutylene with acetyl sulfate |
US5849677A (en) | 1995-12-27 | 1998-12-15 | Exxon Chemical Patents Inc | Sulfurized olefin composition and its method of preparation |
DE19704482A1 (de) † | 1997-02-06 | 1998-08-13 | Basf Ag | Verfahren zur Herstellung von halogenfreiem, reaktivem Polyisobuten |
US6410491B1 (en) | 2000-03-17 | 2002-06-25 | Chevron Chemical Company Llc | Polyalkenyl sulfonates |
EP1167496A2 (en) * | 2000-04-14 | 2002-01-02 | Chevron Oronite Company LLC | A gear oil composition with improved properties |
JP2002097488A (ja) * | 2000-09-19 | 2002-04-02 | Ethyl Corp | 増強された最終動力伝達装置性能のギア油配合物 |
US6303547B1 (en) * | 2000-09-19 | 2001-10-16 | Ethyl Corporation | Friction modified lubricants |
DE10059318B4 (de) * | 2000-11-29 | 2005-02-10 | Clariant Gmbh | Kosmetische Mittel enthaltend Alk(en)ylbernsteinsäurederivate |
US20020151441A1 (en) * | 2001-02-14 | 2002-10-17 | Sanjay Srinivasan | Automatic transmission fluids with improved anti-shudder properties |
US6355839B1 (en) * | 2001-08-31 | 2002-03-12 | Chevron U.S.A., Inc. | Alkylation of diphenylamine with polyisobutylene oligomers |
US6884855B2 (en) | 2003-01-30 | 2005-04-26 | Chevron Oronite Company Llc | Sulfurized polyisobutylene based wear and oxidation inhibitors |
-
2003
- 2003-01-30 US US10/355,539 patent/US6884855B2/en not_active Expired - Lifetime
- 2003-12-22 EP EP03258131A patent/EP1443061B2/en not_active Expired - Lifetime
- 2003-12-22 DE DE60334331T patent/DE60334331D1/de not_active Expired - Lifetime
- 2003-12-22 EP EP07016758A patent/EP1857474B1/en not_active Expired - Lifetime
- 2003-12-22 EP EP10177372A patent/EP2287210B1/en not_active Expired - Lifetime
- 2003-12-22 DE DE60317872T patent/DE60317872T3/de not_active Expired - Lifetime
- 2003-12-31 CA CA2454714A patent/CA2454714C/en not_active Expired - Fee Related
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2004
- 2004-01-13 SG SG200400114-5A patent/SG137660A1/en unknown
- 2004-01-29 JP JP2004022131A patent/JP4895478B2/ja not_active Expired - Lifetime
- 2004-11-23 US US10/997,610 patent/US7414013B2/en not_active Expired - Lifetime
Also Published As
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EP2287210A2 (en) | 2011-02-23 |
DE60317872T2 (de) | 2008-11-27 |
US7414013B2 (en) | 2008-08-19 |
EP1857474A3 (en) | 2008-02-13 |
US20050153850A1 (en) | 2005-07-14 |
EP2287210B1 (en) | 2012-07-18 |
CA2454714A1 (en) | 2004-07-30 |
DE60317872T3 (de) | 2013-01-24 |
US6884855B2 (en) | 2005-04-26 |
DE60317872D1 (de) | 2008-01-17 |
EP1443061A1 (en) | 2004-08-04 |
US20040152817A1 (en) | 2004-08-05 |
EP1443061B2 (en) | 2012-10-31 |
EP1857474A2 (en) | 2007-11-21 |
EP1857474B1 (en) | 2010-09-22 |
EP1443061B1 (en) | 2007-12-05 |
EP2287210A3 (en) | 2011-04-20 |
CA2454714C (en) | 2012-03-13 |
DE60334331D1 (de) | 2010-11-04 |
JP2004231654A (ja) | 2004-08-19 |
SG137660A1 (en) | 2007-12-28 |
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