CA2991769A1 - Lubrifiants a base d'un detergent contenant du calcium et leur utilisation pour ameliorer un pre-allumage a basse vitesse - Google Patents
Lubrifiants a base d'un detergent contenant du calcium et leur utilisation pour ameliorer un pre-allumage a basse vitesse Download PDFInfo
- Publication number
- CA2991769A1 CA2991769A1 CA2991769A CA2991769A CA2991769A1 CA 2991769 A1 CA2991769 A1 CA 2991769A1 CA 2991769 A CA2991769 A CA 2991769A CA 2991769 A CA2991769 A CA 2991769A CA 2991769 A1 CA2991769 A1 CA 2991769A1
- Authority
- CA
- Canada
- Prior art keywords
- lubricating oil
- oil composition
- calcium
- detergent
- low
- 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.)
- Granted
Links
- 239000003599 detergent Substances 0.000 title claims abstract description 170
- 239000011575 calcium Substances 0.000 title claims abstract description 128
- 229910052791 calcium Inorganic materials 0.000 title claims abstract description 121
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims abstract description 113
- 239000000314 lubricant Substances 0.000 title claims description 21
- 239000000203 mixture Substances 0.000 claims abstract description 235
- 239000010687 lubricating oil Substances 0.000 claims abstract description 170
- 230000007935 neutral effect Effects 0.000 claims abstract description 57
- 239000002199 base oil Substances 0.000 claims abstract description 55
- 238000002485 combustion reaction Methods 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000003921 oil Substances 0.000 claims description 69
- 239000000654 additive Substances 0.000 claims description 52
- 239000002270 dispersing agent Substances 0.000 claims description 51
- 229910052751 metal Inorganic materials 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000002184 metal Substances 0.000 claims description 46
- 238000012360 testing method Methods 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 239000003607 modifier Substances 0.000 claims description 27
- 230000000996 additive effect Effects 0.000 claims description 24
- 239000003963 antioxidant agent Substances 0.000 claims description 24
- 230000001050 lubricating effect Effects 0.000 claims description 23
- 230000009467 reduction Effects 0.000 claims description 18
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 17
- 239000000446 fuel Substances 0.000 claims description 13
- 230000001603 reducing effect Effects 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 9
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- -1 that is Chemical group 0.000 description 124
- 235000019198 oils Nutrition 0.000 description 68
- 239000012530 fluid Substances 0.000 description 41
- 239000010936 titanium Substances 0.000 description 31
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 26
- 229910052719 titanium Inorganic materials 0.000 description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
- 239000011777 magnesium Substances 0.000 description 23
- 229910052749 magnesium Inorganic materials 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 23
- 125000001183 hydrocarbyl group Chemical group 0.000 description 21
- 239000010705 motor oil Substances 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 18
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 18
- 239000011593 sulfur Substances 0.000 description 18
- 239000011733 molybdenum Substances 0.000 description 17
- 229910052750 molybdenum Inorganic materials 0.000 description 17
- 229920002367 Polyisobutene Polymers 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- 230000006872 improvement Effects 0.000 description 16
- 239000005078 molybdenum compound Substances 0.000 description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 15
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 150000002752 molybdenum compounds Chemical class 0.000 description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 13
- 150000002989 phenols Chemical class 0.000 description 13
- 229910052698 phosphorus Inorganic materials 0.000 description 13
- 239000011574 phosphorus Substances 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 230000003078 antioxidant effect Effects 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 12
- 229960002317 succinimide Drugs 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 150000003609 titanium compounds Chemical class 0.000 description 11
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 230000006870 function Effects 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 229940014800 succinic anhydride Drugs 0.000 description 8
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 7
- 239000003502 gasoline Substances 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 150000001639 boron compounds Chemical class 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 4
- 229910000838 Al alloy Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 description 4
- AVVIDTZRJBSXML-UHFFFAOYSA-L calcium;2-carboxyphenolate;dihydrate Chemical compound O.O.[Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O AVVIDTZRJBSXML-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000000994 depressogenic effect Effects 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000002272 engine oil additive Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical compound C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- SMDQFHZIWNYSMR-UHFFFAOYSA-N sulfanylidenemagnesium Chemical compound S=[Mg] SMDQFHZIWNYSMR-UHFFFAOYSA-N 0.000 description 4
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002551 biofuel Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010338 boric acid Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 238000007906 compression Methods 0.000 description 3
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- 150000005676 cyclic carbonates Chemical class 0.000 description 3
- 125000005266 diarylamine group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052752 metalloid Inorganic materials 0.000 description 3
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- 235000010446 mineral oil Nutrition 0.000 description 3
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- 239000001301 oxygen Substances 0.000 description 3
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- 239000003208 petroleum Substances 0.000 description 3
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- 229920000193 polymethacrylate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000003873 salicylate salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000000180 1,2-diols Chemical class 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 2
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- MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical class [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 description 2
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 239000007866 anti-wear additive Substances 0.000 description 2
- SCJNCDSAIRBRIA-DOFZRALJSA-N arachidonyl-2'-chloroethylamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCCl SCJNCDSAIRBRIA-DOFZRALJSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
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- JUWGUJSXVOBPHP-UHFFFAOYSA-B titanium(4+);tetraphosphate Chemical class [Ti+4].[Ti+4].[Ti+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JUWGUJSXVOBPHP-UHFFFAOYSA-B 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
- C10M135/10—Sulfonic acids or derivatives 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms 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
- C10M2207/027—Neutral 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
- 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
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- 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
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- 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
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- 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
- C10M2219/042—Sulfate esters
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- 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
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- 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—Overbased sulfonic acid salts
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- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
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- 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
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- 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
- C10N2010/12—Groups 6 or 16
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- 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
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- 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
- C10N2030/08—Resistance to extreme temperature
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- 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
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- 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
- C10N2040/25—Internal-combustion engines
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- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
L'invention concerne une composition d'huile lubrifiante et un procédé de fonctionnement d'un moteur à combustion interne suralimenté. La composition d'huile lubrifiante comprend plus de 50 % en poids d'une huile de base, un détergent surbasique ayant un TBN supérieur à 225 mg KOH/g et un détergent neutre/à faible indice de basicité dont l'indice TBN peut atteindre 175 mg KOH/g. Une quantité totale de calcium présent dans le détergent neutre surbasique et à faible indice de basicité est située dans une plage comprise entre une valeur supérieure à 1100 ppm et inférieure à 2400 ppm en poids sur la base du poids total de la composition d'huile lubrifiante. La composition d'huile lubrifiante et le procédé peuvent être efficaces pour réduire des événements de pré-allumage à basse vitesse dans un moteur à combustion interne suralimenté qui est lubrifié au moyen de la composition d'huile lubrifiante par rapport à des compositions d'huile lubrifiante disponibles dans le commerce.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
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US201562193297P | 2015-07-16 | 2015-07-16 | |
US62/193,297 | 2015-07-16 | ||
US15/047,934 | 2016-02-19 | ||
US15/047,934 US20170015933A1 (en) | 2015-07-16 | 2016-02-19 | Additives and lubricating oil compositions for improving low speed pre-ignition |
US15/147,317 | 2016-05-05 | ||
US15/147,317 US10336959B2 (en) | 2015-07-16 | 2016-05-05 | Lubricants with calcium-containing detergent and their use for improving low speed pre-ignition |
PCT/US2016/042220 WO2017011633A1 (fr) | 2015-07-16 | 2016-07-14 | Lubrifiants à base d'un détergent contenant du calcium et leur utilisation pour améliorer un pré-allumage à basse vitesse |
Publications (2)
Publication Number | Publication Date |
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CA2991769A1 true CA2991769A1 (fr) | 2017-01-19 |
CA2991769C CA2991769C (fr) | 2020-07-07 |
Family
ID=61066569
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2991769A Active CA2991769C (fr) | 2015-07-16 | 2016-07-14 | Lubrifiants a base d'un detergent contenant du calcium et leur utilisation pour ameliorer un pre-allumage a basse vitesse |
Country Status (8)
Country | Link |
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EP (1) | EP3322781B1 (fr) |
JP (1) | JP6708831B2 (fr) |
KR (1) | KR102103653B1 (fr) |
CN (1) | CN107922873B (fr) |
BR (1) | BR112018000353B1 (fr) |
CA (1) | CA2991769C (fr) |
MX (1) | MX371195B (fr) |
RU (1) | RU2720202C2 (fr) |
Families Citing this family (5)
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CN109983104A (zh) * | 2017-01-20 | 2019-07-05 | 雪佛龙奥伦耐有限责任公司 | 在直喷火花点火式发动机中防止或减少低速早燃的润滑油组合物和方法 |
CN111212891A (zh) * | 2017-10-18 | 2020-05-29 | 国际壳牌研究有限公司 | 用于减少低速提前点火的方法 |
CA3101044A1 (fr) * | 2018-05-25 | 2019-11-28 | Chevron Oronite Company Llc | Procede de prevention ou de reduction de preallumage a faible vitesse dans des moteurs a bougie a injection directe avec un lubrifiant contenant du silane |
CN113930274B (zh) * | 2020-06-29 | 2023-06-13 | 中国石油化工股份有限公司 | 一种低黏度节能兼顾低速早燃控制性能的发动机油组合物 |
CN116144418A (zh) * | 2023-02-27 | 2023-05-23 | 辽宁百特润滑科技有限责任公司 | 一种汽机油组合物及其制备方法 |
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US4954272A (en) * | 1989-03-27 | 1990-09-04 | Texaco Inc. | Process for preparing overbased calcium sulfonates |
US5498355A (en) * | 1994-09-20 | 1996-03-12 | Ethyl Corporation | Lubricant compositions of enhanced performance capabilities |
US5726133A (en) * | 1996-02-27 | 1998-03-10 | Exxon Research And Engineering Company | Low ash natural gas engine oil and additive system |
US6140280A (en) * | 1996-10-29 | 2000-10-31 | Idemitsu Kosan Co., Ltd. | Succinimide compound and method for producing it, lubricating oil additive comprising the compound and lubricating oil composition comprising the compound for diesel engine |
US6143701A (en) * | 1998-03-13 | 2000-11-07 | Exxon Chemical Patents Inc. | Lubricating oil having improved fuel economy retention properties |
US6723685B2 (en) * | 2002-04-05 | 2004-04-20 | Infineum International Ltd. | Lubricating oil composition |
EP1803799A4 (fr) * | 2004-10-19 | 2012-09-05 | Nippon Oil Corp | Formule de lubrifiant et formule d antioxydant |
US7550415B2 (en) * | 2004-12-10 | 2009-06-23 | Shell Oil Company | Lubricating oil composition |
JP5513703B2 (ja) * | 2005-05-27 | 2014-06-04 | 出光興産株式会社 | 潤滑油組成物 |
US7867957B2 (en) | 2007-03-30 | 2011-01-11 | Nippon Oil Corporation | Lubricating oil composition |
CN102690715B (zh) * | 2011-03-24 | 2014-03-12 | 中国石油化工股份有限公司 | 一种四冲程摩托车发动机润滑油组合物 |
US9279094B2 (en) * | 2012-12-21 | 2016-03-08 | Afton Chemical Corporation | Friction modifiers for use in lubricating oil compositions |
US10227544B2 (en) * | 2013-08-15 | 2019-03-12 | Infineum International Limited | Automotive transmission fluid compositions for improved energy efficiency |
EP3878933A1 (fr) * | 2013-09-19 | 2021-09-15 | The Lubrizol Corporation | Compositions lubrifiantes pour moteurs à injection directe |
ES2861315T3 (es) * | 2013-09-19 | 2021-10-06 | Lubrizol Corp | Composiciones lubricantes para los motores de inyección directa |
JP6300686B2 (ja) * | 2014-01-31 | 2018-03-28 | Emgルブリカンツ合同会社 | 潤滑油組成物 |
CN104140864A (zh) * | 2014-07-14 | 2014-11-12 | 广西大学 | 一种f-t发动机油组合物 |
CN104342266B (zh) * | 2014-09-29 | 2016-07-06 | 陕西通用石油化工有限公司 | 公交汽车燃气发动机专用润滑油 |
CN104403721B (zh) * | 2014-10-13 | 2017-04-05 | 菲玛(新加坡)有限公司 | 一种气缸油复合添加剂及其制备方法 |
JP6572597B2 (ja) | 2015-03-31 | 2019-09-11 | 出光興産株式会社 | 4サイクルエンジン用潤滑油組成物 |
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- 2016-07-14 RU RU2018104014A patent/RU2720202C2/ru active
- 2016-07-14 KR KR1020187003363A patent/KR102103653B1/ko active IP Right Grant
- 2016-07-14 EP EP16741792.2A patent/EP3322781B1/fr active Active
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- 2016-07-14 BR BR112018000353-0A patent/BR112018000353B1/pt active IP Right Grant
- 2016-07-14 JP JP2017567100A patent/JP6708831B2/ja active Active
- 2016-07-14 CA CA2991769A patent/CA2991769C/fr active Active
- 2016-07-14 CN CN201680039372.2A patent/CN107922873B/zh active Active
Also Published As
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CN107922873A (zh) | 2018-04-17 |
KR102103653B1 (ko) | 2020-04-22 |
RU2018104014A3 (fr) | 2019-12-23 |
BR112018000353B1 (pt) | 2022-01-18 |
EP3322781B1 (fr) | 2019-12-18 |
JP2018520240A (ja) | 2018-07-26 |
CN107922873B (zh) | 2021-08-27 |
CA2991769C (fr) | 2020-07-07 |
JP6708831B2 (ja) | 2020-06-10 |
BR112018000353A2 (pt) | 2018-09-11 |
EP3322781A1 (fr) | 2018-05-23 |
RU2018104014A (ru) | 2019-08-02 |
RU2720202C2 (ru) | 2020-04-27 |
KR20180048596A (ko) | 2018-05-10 |
MX371195B (es) | 2020-01-22 |
MX2018000152A (es) | 2018-03-23 |
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