CN101010418B - 润滑油用添加剂 - Google Patents
润滑油用添加剂 Download PDFInfo
- Publication number
- CN101010418B CN101010418B CN2005800292329A CN200580029232A CN101010418B CN 101010418 B CN101010418 B CN 101010418B CN 2005800292329 A CN2005800292329 A CN 2005800292329A CN 200580029232 A CN200580029232 A CN 200580029232A CN 101010418 B CN101010418 B CN 101010418B
- Authority
- CN
- China
- Prior art keywords
- zinc
- additive
- lubricant
- compound
- acid ester
- 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 - Fee Related
Links
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 31
- 239000000654 additive Substances 0.000 title claims abstract description 28
- 230000000996 additive effect Effects 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000000314 lubricant Substances 0.000 claims abstract description 28
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 125000000962 organic group Chemical group 0.000 claims abstract description 8
- -1 alkylbenzene zinc carboxylate Chemical class 0.000 claims description 40
- 239000011701 zinc Substances 0.000 claims description 35
- 229910052725 zinc Inorganic materials 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 239000003879 lubricant additive Substances 0.000 claims description 19
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 18
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 16
- 239000005864 Sulphur Substances 0.000 claims description 13
- 150000003752 zinc compounds Chemical class 0.000 claims description 10
- 239000011787 zinc oxide Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 7
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical group 0.000 claims description 4
- MATKLGVYEVOFFU-UHFFFAOYSA-N 2-dodecylsulfanylethyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCSCCOP(O)(O)=O MATKLGVYEVOFFU-UHFFFAOYSA-N 0.000 claims description 3
- LMTYOTHYHDCUKY-UHFFFAOYSA-N 2-hexylsulfanylethyl dihydrogen phosphate Chemical group CCCCCCSCCOP(O)(O)=O LMTYOTHYHDCUKY-UHFFFAOYSA-N 0.000 claims description 3
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims description 3
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 3
- 239000011667 zinc carbonate Substances 0.000 claims description 3
- 229910000010 zinc carbonate Inorganic materials 0.000 claims description 3
- 235000004416 zinc carbonate Nutrition 0.000 claims description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 3
- 229940007718 zinc hydroxide Drugs 0.000 claims description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 3
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 claims description 3
- LZSZSURMDPHQQA-UHFFFAOYSA-N 1,1'-biphenyl;zinc Chemical compound [Zn].C1=CC=CC=C1C1=CC=CC=C1 LZSZSURMDPHQQA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002485 combustion reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 18
- 230000003078 antioxidant effect Effects 0.000 abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 abstract description 7
- 239000003963 antioxidant agent Substances 0.000 abstract description 6
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 27
- 239000007795 chemical reaction product Substances 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 19
- 239000002585 base Substances 0.000 description 19
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
- 238000005299 abrasion Methods 0.000 description 13
- 239000002480 mineral oil Substances 0.000 description 13
- 235000010446 mineral oil Nutrition 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 6
- 238000012423 maintenance Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- IHGAVIJIBMCWQZ-UHFFFAOYSA-N 2-dodecylsulfanylethoxy dihydrogen phosphate Chemical compound CCCCCCCCCCCCSCCOOP(O)(O)=O IHGAVIJIBMCWQZ-UHFFFAOYSA-N 0.000 description 3
- QNKKORRUJNLHAC-UHFFFAOYSA-N 2-hexadecylsulfanylethoxy dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCSCCOOP(O)(O)=O QNKKORRUJNLHAC-UHFFFAOYSA-N 0.000 description 3
- HXBWMLNGEWZOGP-UHFFFAOYSA-N 2-hexylsulfanylethoxy dihydrogen phosphate Chemical compound CCCCCCSCCOOP(O)(O)=O HXBWMLNGEWZOGP-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000003915 liquefied petroleum gas Substances 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010023198 Joint ankylosis Diseases 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
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- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012208 gear oil Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
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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 2
- IIZRZKZFPRBVEZ-UHFFFAOYSA-N 2-hydroxyoctane-2-sulfonic acid Chemical compound CCCCCCC(C)(O)S(O)(=O)=O IIZRZKZFPRBVEZ-UHFFFAOYSA-N 0.000 description 1
- XFKXMKBEITXADM-UHFFFAOYSA-N 2-hydroxytetradecane-2-sulfonic acid Chemical compound CCCCCCCCCCCCC(C)(O)S(O)(=O)=O XFKXMKBEITXADM-UHFFFAOYSA-N 0.000 description 1
- 208000008822 Ankylosis Diseases 0.000 description 1
- AUHSOCNTXNVKIQ-UHFFFAOYSA-N C(C)P(O)(O)=O.[S] Chemical compound C(C)P(O)(O)=O.[S] AUHSOCNTXNVKIQ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
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- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
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- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- 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
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- 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
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- 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
- C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
- C10M129/54—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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Abstract
本发明提供作为具有抗氧化稳定性、热稳定性、耐NOx性的极压添加剂或耐磨耗剂而具有优良性能的润滑剂用添加剂及含有该润滑剂用添加剂的润滑油组合物。本发明为含有通式[I]表示的磷酸酯衍生物的润滑剂用添加剂、以及配合该润滑油用添加剂的润滑油组合物。[式中,Y表示S(硫)或O(氧)。R1表示碳数4-24的一价有机基团,R2表示碳数1-6的二价有机基团。n表示1-3的整数。]
Description
技术领域
本发明涉及润滑剂用添加剂,更详细地说,涉及抗氧化稳定性、热稳定性、耐NOx劣化性优良的、作为极压添加剂或耐磨耗剂具有优异功能的新型磷酸酯衍生物,含有该磷酸酯衍生物与锌化合物的反应物或者磷酸酯衍生物与有机锌化合物的混合物的润滑剂用添加剂,以及配合上述添加剂的润滑油组合物。
背景技术
在机械装置运转时,润滑油需要具有防止部件之间滑动接触或转动接触而使金属表面磨耗的能力和控制磨耗的能力。因此,为了提高润滑油的耐磨耗性,且延长装置寿命,添加剂的作用就变得极为重要。
另一方面,单独使用基油,无法具备以内燃机用润滑油或驱动类润滑油为代表的其它润滑油组合物的用途所要求的多种特殊性质。因此,有必要使用润滑油用添加剂,赋予各自特殊的性质,以提高润滑油组合物的性能。因此,一直以来致力于适用于这些润滑油组合物的具有一种或一种以上的性质的润滑油的探索。
例如,专利文献1中,作为润滑油,公开了通式
[式中,R表示碳数2-3的饱和脂肪烃基,X分别为O或S,且多个R′分别为碳数1-18的烷基等。]表示的含有磷和硫的磷酸酯化合物,但没有记载具体的用途。
专利文献2中,公开了通式
[式中,A表示碳数2-6的亚烷基,R′分别为碳数2-4的烷基。]表示的磷酸酯衍生物,而且,其与丙烯酸酯共聚,可用作防火剂。
专利文献3中,公开了含有芳胺和通式
[式中,X为O或S(至少1个是S),m为0或1(至少3个m为1),多个R表示烷基或芳基。]表示的含有有机硫磷酸或亚磷酸的酯基的润滑组合物,可用作抗氧化剂。
专利文献4中,公开了通式Ya-S-Yb[式中,Ya为
Z为烃基,R分别为烃基、烃氧基等,R′为氢原子或二价烃基。X为S或O,Yb为烃基等。]表示的含有磷和硫的化合物,可用作抗氧化稳定剂和耐磨耗剂。
专利文献5中,公开了通式
[式中,R表示烷基、环烷基等,R′表示烷基,x为1-4,m为1或2,m+m′=3。]表示的烷基硫磷酸酯,可用作亚铁金属的防腐剂。
在专利文献6中,公开了通式
RO-(CH2CH2O)xP(R′)-OH
[式中,R表示烷基或烯基,R′表示OH、烷氧基等,x为2-4。1表示的烷氧基聚乙烯含氧酸亚磷酸酯,可用作使对油的水容许度提高的添加剂。
专利文献7中,公开了通式
[式中,R为烷基等,R′为亚烷基,X表示O、NH或S。m为1-3,m′为1-12,m″为0或1。]表示的环式磷酸酯,可用作汽车传动装置液体之类的润滑油组合物的防磨耗剂、抗氧化剂和摩擦改性剂。
专利文献8中,公开了至少1种硫组合物与二-或三-烃基亚磷酸酯和/或胺化合物反应得到的含硫化合物的含磷和氮的衍生物,作为对燃料及润滑和功能性流体组合物有用的添加剂。
专利文献9和专利文献10中,公开了含有(1)β-羟基硫醚反应物,(2)亚磷酸氢二烃、亚磷酸三烃及它们的混合物、(3)特定的求核反应物的反应混合物的反应产物,可用作耐磨耗剂或抗氧化剂。
专利文献11中,公开了通式
(R-X′-R′-Y′)m-P-(OH)3-m
[式中,X′表示S(硫)、Y′表示S(硫)或O(氧)。R表示碳数6-20的有机基团,R′表示碳数1-6的有机基团。m为1-3的整数。]
和通式
[式中,X′、Y′、R、R′同上。P为0-2的整数、q为0或1的整数,它们不同时为0。]表示的含有磷和硫的亚磷酸化合物。
专利文献12中,公开了将通式
A-(RO)-(R′O)-P-(O)m
[式中,A表示H或OH,m表示0或1,m为0时A表示OH、m为1时A表示H或OH,R和R′分别表示H或含有至少1个S或O的烃。]表示的磷酸和/或亚磷酸与含硼的酰亚胺分散剂进行加热处理得到的组合物。
专利文献13中,公开了通式
[式中,R分别为氢原子或碳数1-30的烃基,X分别为O和S,Z表示金属原子。]表示的磷酸化合物,可用作碱值维持性、防磨耗性的添加剂。
但是,将这些现有的添加剂用作润滑油时,在高负荷、严苛条件下,还不能满足极压性、耐磨耗性和摩擦特性的要求。
【专利文献1】美国专利第2750342号说明书
【专利文献2】美国专利第2960523号说明书
【专利文献3】美国专利第3446738号说明书
【专利文献4】美国专利第4081387号说明书
【专利文献5】美国专利第4511480号说明书
【专利文献6】美国专利第4579672号说明书
【专利文献7】美国专利第4776969号说明书
【专利文献8】WO88/03554号小册子
【专利文献9】WO89/12666号小册子
【专利文献10】特表平3-500061号公报
【专利文献11】特开平11-171892号公报
【专利文献12】美国专利第6352962号说明书
【专利文献13】特开2002-294271号公报
发明内容
发明要解决的课题
本发明正是鉴于上述情况而开发的,其目的是提供新型含硫有机磷化合物以及含有该化合物的润滑油用添加剂,进一步提供在内燃机或驱动类机械等高负荷的严苛运转条件下,极压性、耐磨耗性及摩擦特性优良的润滑油组合物。
解决课题的方法
本发明人等为达成上述目的,进行反复深入的研究结果,发现特定的磷酸酯衍生物的热稳定性、抗氧化稳定性、耐NOx性及碱值维持性优良,作为极压剂、耐磨耗剂及摩擦特性改性剂是有用的,至此完成本发明。
即,本发明提供下述的润滑剂用添加剂等。
1.含有通式[I]表示的磷酸酯衍生物(A)的润滑剂用添加剂。
[式中,Y表示S(硫)或O(氧)。R1表示碳数4-24的一价有机基团,R2表示碳数1-6的二价有机基团。n表示1-3的整数。]
2.含有通式[I]表示的磷酸酯衍生物(A)与锌化合物(B)的反应物的润滑剂用添加剂。
[式中,Y表示S(硫)或O(氧)。R1表示碳数4-24的一价有机基团,R2表示碳数1-6的二价有机基团。n表示1-3的整数。]
3.含有通式[I]表示的磷酸酯衍生物(A)和有机锌化合物(C)的混合物的润滑剂用添加剂。
[式中,Y表示S(硫)或O(氧)。R1表示碳数4-24的一价有机基团,R2表示碳数1-6的二价有机基团。n表示1-3的整数。]
4.上述1-3中任一项所述的润滑剂用添加剂,是上述通式(I)中Y为O(氧)的磷酸酯衍生物。
5.上述2所述的润滑剂用添加剂,其中,锌化合物(B)为选自金属锌、锌氧化物、有机锌化合物、锌含氧酸盐、卤化锌及锌配合物中的至少1种化合物。
6.上述2所述的润滑剂用添加剂,其中,锌化合物(B)为选自锌、氧化锌、氢氧化锌、碳酸锌、二甲基锌、二苯基锌及锌配合物中的至少1种化合物。
7.上述3所述的润滑剂用添加剂,其中,有机锌化合物(C)为选自烷基羧酸锌、烯基羧酸锌、烷基苯羧酸锌及烯基苯羧酸锌中的至少1种化合物。
8.上述3所述的润滑剂用添加剂,其中,有机锌化合物(C)为选自油酸锌、异硬脂酸锌、硬脂酸锌、烷基苯羧酸锌、烷基水杨酸锌中的至少1种化合物。
9.润滑剂用添加剂组合物,配合上述1-8中任一项所述的润滑剂用添加剂而成。
10.润滑油组合物,其特征在于,润滑油基油中含有按磷元素换算量计为0.001-0.5质量%的上述1-8中任一项所述的润滑剂用添加剂。
11.内燃机用润滑油组合物,其特征在于,润滑油基油中含有按磷元素换算量计为0.001-0.5质量%的上述1-8中任一项所述的润滑剂用添加剂
12.润滑剂用添加剂的制造方法,其特征在于,由上述2或4所述的磷酸酯衍生物(A)与锌化合物(B)反应制得。
发明效果
本发明的润滑油组合物在NOx气氛下的碱值维持性,即长效润滑性能极优异,而且具有优良的防磨耗性能和高温净化性能。
因此,可有效用作在NOx气体浓度高、且较高温下的内燃机用的润滑油,例如汽油机或柴油机以及气体发动机的,以天然气体、LPG(液化石油气)、裂化气、煤裂化气等为燃料的内燃机的曲柄箱用油等。另外,本发明的润滑油组合物也可用作需要碱值维持性、以及防磨耗性能及高温净化性的润滑油,例如,动力传输用润滑油、齿轮油、轴承油、消震器油、工业用润滑油等。
具体实施方式
本申请第一个发明为含有上述通式[I]表示的磷酸酯衍生物(A)的润滑剂用添加剂。
通式[I]中,R1优选碳数4-24的烃基,特别优选碳数8-16的烷基。R1的碳数小于4时,油溶性、极压特性、耐磨耗特性、摩擦特性、润滑特性变差,同时腐蚀性增大。R1具体地可举出丁基、戊基、各种己基、各种庚基、各种辛基、各种壬基、各种癸基、各种十一烷基、各种十二烷基、各种十三烷基、各种十四烷基、各种十五烷基、各种十六烷基、各种十七烷基、各种十八烷基、各种十九烷基、各种二十烷基等烷基;环己基、各种甲基环己基、各种乙基环己基、各种丙基环烷基、各种二甲基环烷基等环烷基;苯基、各种甲苯基、各种乙苯基、各种丙苯基、各种三甲苯基、各种丁苯基、各种萘基等芳基;苄基、各种苯乙基、各种甲基苄基、各种苯丙基、各种苯丁基等芳烷基等。
另外,通式[I]中,R2优选碳数1-6的烃基,特别优选碳数1-4的亚烷基。具体来说,可举出亚甲基、亚乙基、1,2-亚丙基;1,3-亚丙基、各种亚丁基、各种亚戊基、各种亚己基的二价脂肪族基、环己烷、甲基环戊烷等脂环烃上有2个键合部位的脂环基、各种亚苯基等。
另外,Y表示S(硫)或O(氧),通式[I]中含有至少1个以上S。n表示1-3的整数,优选1或2,更优选2。
作为上述通式[I]表示的磷酸酯衍生物的具体例子,可举出三(己基硫代乙氧基)磷酸酯、三(辛基硫代乙氧基)磷酸酯、三(十二烷基硫代乙氧基)磷酸酯、三(十六烷基硫代乙氧基)磷酸酯、二(己基硫代乙氧基)磷酸酯、二(辛基硫代乙氧基)磷酸酯、二(十二烷基硫代乙氧基)磷酸酯、二(十六烷基硫代乙氧基)磷酸酯、单(己基硫代乙氧基)磷酸酯、单(辛基硫代乙氧基)磷酸酯、单(十二烷基硫代乙氧基)磷酸酯、单(十六烷基硫代乙氧基)磷酸酯等。
上述通式[I]表示的磷酸酯衍生物的制造方法没有特殊限制,例如,磷酸酯衍生物可通过使通式[II]表示的烷硫基烷基醇或者通式[III]表示的烷硫基醇盐与氧氯化磷(POCl3)在无催化剂或碱的存在下发生反应来制得。
R1-S-R2-YH...[II]
[式中,Y表示S(硫)或O(氧)。R1、R2同上。]
R1-X-R2-YNa...[III]
[式中,X、Y、R1、R2同上。]
上述反应中,烷硫基烷基醇或烷硫基醇盐与氧氯化磷的使用比例,通常按摩尔比,相对于氧氯化磷1摩尔,烷硫基烷基醇或烷硫基醇盐为0.1-5.0摩尔,更优选1-3摩尔,进一步优选1.5-2.5摩尔的范围。
另外,反应温度通常在-60~100℃、优选-30~50℃的范围内选择。该反应既可以在无催化剂下进行,也可以在碱存在下进行。所述碱例如可使用三乙胺、吡啶等。予以说明,进行该反应时,溶剂例如可使用二甲苯、甲苯、四氢呋喃(THF)、二乙醚等。
作为其他制造方法,可通过使通式[II]表示的烷硫基烷基醇与五氧化二磷(P2O5)发生反应来制得。
R1-S-R2-YH...[II]
[式中,Y表示S(硫)或O(氧)。R1、R2同上。]
在该反应中,烷硫基烷基醇与五氧化二磷的使用比例,通常按摩尔比,相对于五氧化二磷1摩尔,烷硫基烷基醇为1-12摩尔,更优选2-6摩尔,进一步优选3-4摩尔的范围。
另外,反应温度通常在0~140℃左右,优选30~110℃,更优选在50~90℃的范围内选择。予以说明,进行该反应时,溶剂例如可使用二甲苯、甲苯、THF、二乙醚、氯仿等。
本申请第二个发明为含有上述磷酸酯衍生物(A)与锌化合物(B)的反应物的润滑剂用添加剂。
锌化合物(B)优选金属锌、锌氧化物、有机锌化合物、锌含氧酸盐、卤化锌、锌配合物等,具体来说,可举出锌、氧化锌、氢氧化锌、碳酸锌、二甲基锌、二苯锌、锌配合物等。
磷酸酯衍生物(A)与锌化合物(B)的反应可在无催化剂或催化剂存在下进行反应而制得。该反应中,磷酸酯衍生物与锌化合物的使用比例,通常按摩尔比,相对于锌化合物1摩尔,磷酸酯衍生物为0.1-5.0摩尔、优选1-3摩尔、更优选1.5-2.5摩尔的范围。
另外,反应温度范围,通常在室温~200℃、优选40~150℃的范围内进行选择。予以说明,进行该反应时,溶剂例如可使用二甲苯、甲苯、己烷等。
本申请第三个发明是含有磷酸酯衍生物(A)和有机锌化合物(C)的混合物的润滑剂用添加剂。
有机锌盐(C)优选烷基或烯基羧酸锌、烷基或烯基苯羧酸锌等,具体来说,可举出油酸锌、异硬脂酸锌、硬脂酸锌、烷基苯羧酸锌、烷基水杨酸锌等。
如上所述,本发明中的润滑剂用添加剂可以仅使用磷酸酯衍生物(A),但优选使用(A)成分与锌化合物(B)的反应物,或者(A)成分和有机锌化合物(C)的混合物。另外,这些反应物和混合物,可以只有1种,也可以含有2种以上。
上述添加剂的有效配合量根据用途各不相同,通常以基油为基准,含有以磷元素换算量计为0.001-1.0质量%,优选0.005-0.5质量%的比例。
润滑油基油可使用矿物油或合成油。矿物油、合成油各种各样,可根据用途等进行适当选择。矿物油例如可举出石蜡基系矿物油、环烷基系矿物油、中间基系矿物油等,具体例子可举出经溶剂纯化或氢化纯化的轻质中性油、中质中性油、重质中性油、重质润滑油料等。
另一方面,合成油例如可举出聚α-烯烃、α-烯烃共聚物、聚丁烯、烷基苯、聚醇酯、二元酸酯、多元醇酯、聚氧亚烷基二醇、聚氧亚烷基二醇酯、聚氧亚烷基二醇醚、环链烷烃类化合物等。
这些润滑油基油可以分别单独或者两种以上组合使用,也可以组合矿物油和合成油来使用。
在不损害本发明目的的范围内,根据需要,可以在本发明的润滑剂用添加剂组合物中配合以往润滑剂组合物中常用的各种添加成分,例如净化分散剂、抗氧化剂、防锈剂、消泡剂、粘度指数改善剂、倾点下降剂、抗乳化剂、其他极压剂、耐磨耗剂等。
【实施例】
以下,通过实施例说明本发明,但本发明并不局限于这些实施例。
实施例1
在氮气流下,向500毫升的烧瓶中加入氢化钠13.2g(0.55mol)和二甲苯100毫升,边搅拌边滴入辛基硫代乙醇95.2g(0.5mol)的二甲苯100毫升溶液。边回流边反应5小时。
另一方面,在1000毫升的烧瓶中,边用冰水冷却边在氮气流下加入氧氯化磷38.3g(0.25mol)和THF100毫升。用2小时滴入上述反应混合物,然后在室温下反应1小时。
向反应溶液中滴入水10g(0.55mol),在室温下搅拌1小时后,加入水100毫升,在室温下搅拌1小时。静置,使有机层和水层分离,再向有机层中加入水100毫升,在室温下搅拌。将该操作重复2次。从有机层中蒸馏除去二甲苯及THF,减压蒸馏除去未反应的辛基硫代乙醇及副反应生成的辛基硫乙基氯化物。生成的辛基硫乙基磷酸酯的产量为75g。
实施例2
向300毫升的烧瓶中加入实施例1所得辛基硫代乙基磷酸酯45g、甲苯50ml、水1g,升温至70℃。添加氧化锌4.1g(0.05mol)。在70℃下反应3小时。减压蒸馏除去甲苯和水后,用相当于150N的矿物油15g进行稀释,过滤反应物。所得反应产物的产量为60g。
实施例3
除了在实施例1中使用十二烷基硫代乙醇123.3g(0.5mol)代替辛基硫代乙醇以外,其余与实施例1同样操作。所得反应产物(十二烷基硫代乙基磷酸酯)的产量为92g。
实施例4
除了在实施例2中使用实施例3所得反应产物(十二烷基硫代乙基磷酸酯)55g代替实施例1所得反应产物以外,其余与实施例2同样操作。所得反应产物的产量为70g。
实施例5
除了在实施例1中使用己基硫代乙醇81.1g(0.5mol)代替辛基硫代乙醇以外,其余与实施例1同样操作。所得反应产物(己基硫代乙基磷酸酯)的产量为61g。
实施例6
除了在实施例2中使用实施例5所得反应产物(己基硫代乙基磷酸酯)33g代替实施例1所得反应产物以外,其余与实施例2同样操作。所得反应产物的产量为50g。
实施例7
除了在实施例1中使用氧氯化磷42.2g(0.275mol)代替氧氯化磷38.3g(0.25mol)以外,其余与实施例1同样操作。所得反应产物(辛基硫代乙基磷酸酯)的产量为62g。
实施例8
除了在实施例2中使用实施例7所得反应产物(辛基硫代乙基磷酸酯)代替实施例1所得反应产物以外,其余与实施例2同样操作。所得反应产物的产量为60g。
实施例9
除了在实施例1中使用氧氯化磷34.5g(0.225mol)代替氧氯化磷38.3g(0.25mol)以外,其余与实施例1同样操作。所得反应产物的产量为78g。
实施例10
除了在实施例2中使用实施例9所得反应产物(辛基硫代乙基磷酸酯)代替实施例1所得反应产物以外,其余与实施例2同样操作。所得反应产物的产量为61g。
实施例11
向500毫升烧瓶中加入辛基硫代乙醇142.8g(0.75mol)和甲苯500毫升,缓缓加入五氧化二磷35.0g(0.25mol)。添加结束后,在80℃下边搅拌边反应6小时,然后减压蒸馏除去甲苯。所得反应产物的产量为178g。
实施例12
向500毫升烧瓶中加入加入油酸112.8g(0.4mol)、氧化锌16.2g(0.2mol)、甲苯500毫升、水2g,在70℃下反应3小时,减压蒸馏除去甲苯和水后,用相当于150N的矿物油30g进行稀释,过滤反应物。所得反应产物的产量为145g。
实施例13
除了在实施例12中使用硬脂酸113.6g(0.4mol)代替油酸以外,其余与实施例12同样操作。所得反应产物的产量为148g。
实施例14
除了在实施例12中使用十二烷基水杨酸122.4g(0.4mol)代替油酸以外,其余与实施例12同样操作。所得反应产物的产量为156g。实施例15-23及比较例1、2
按照表1的配方,向100N矿物油或500N矿物油的基油中加入上述所得磷酸酯衍生物或市售的耐磨耗剂或磷酸二丁酯以及各种添加剂,分别配制本发明的润滑油组合物(实施例15-23)及比较用的润滑油组合物(比较例1、2)。
【表1】
(注)
*1氢化纯化矿物油,100℃运动粘度4.5mm2/s,硫分0.0质量%以下
*2氢化纯化矿物油,100℃运动粘度10.9mm2/s,硫分0.01质量%以下
*3仲二烷基二硫代磷酸锌,含磷量8.2质量%,含锌量9.0质量%、含硫量17.1质量%
*4水杨酸钙,Ca:7.94质量%
*5聚丁烯基琥珀酰亚胺,含氮量1.56质量%
*6硼改性聚丁烯基琥珀酰亚胺,含氮量1.76质量%,含硼量2.0质量%
*7二烷基二苯基胺与受阻酚类抗氧化剂的混合物
*8金属惰性剂、消泡剂、抗乳化剂等
对上述所得各组合物,按下述方法进行耐NOx性试验、气门传动磨耗试验及法列克司(Falex)耐负荷性能试验。
(1)耐NOx性试验
在铁、铜催化剂(氧化试验JIS K-2514的试验片)的存在下,向样品油250毫升中以6升/小时吹入浓度8000ppm的一氧化氮(NO)气体和以6升/小时吹入空气。使样品油的温度保持在140℃,测定强制劣化时的碱值(盐酸法)。可见碱值越减少,即使在内燃机使用的氮氧化物气体气氛下碱值维持性也越高,是更能长期使用的润滑油。
(2)气门传动类磨耗试验
实施JASO M328-95气门传动类磨耗试验,测定100小时试验后的摇臂护垫划痕面积、摇臂磨耗量、凸轮磨耗量。只要其值分别在10以下,则是耐磨耗性能优良的润滑油组合物。
(3)法列克司(Falex)耐负荷性能试验
销的材质:AISI-3153,块的材质:AISI-1137,油量:300ml,旋转数:290rpm,油温:100℃,负荷1112N的条件下,连续运转5分钟后,在油温100℃下持续增加负荷,以ASTM D3233为基准,测定胶住荷重。胶住荷重越高,则表示耐负荷性能越优良的润滑油。
【表2】
表2-1
表2-2
【表3】
JASO M328-95气门传动类磨耗试验 | 实施例15 | 实施例20 | 比较例1 | 比较例2 |
摇臂护垫面的划痕面积(%) | 8.5 | 5.4 | 9.3 | 10 |
凸轮尖部的磨耗量(μm) | 6.7 | 6.9 | 26.8 | 6.7 |
【表4】
法列克司(Falex)耐负荷性能试验 | 实施例15 | 实施例20 | 比较例1 | 比较例2 |
胶住荷重N | 3620 | 3800 | 3900 | 2400 |
由上述表2所示的耐NOx性试验结果可知,本发明的润滑油组合物(实施例15-20)即使在氮氧化物气体气氛下也能显示出优良的碱值维持性。另一方面,在将本发明中的耐磨耗剂替换为二硫代磷酸锌而进行同样试验的比较例1中,碱值维持特性显著的差。
另外,由表3所示气门传动类磨耗试验结果可知,本发明的润滑油组合物(实施例15、20)的耐磨耗性能优良,但比较例1的耐磨耗性能显著的差。
比较例2在氮气氛下显示优良的碱值持续性(表2),耐磨耗性能也优良(表3),但耐负荷性能却比本发明的润滑油组合物(实施例15、20)明显差得多(表4)。
产业实用性
本发明的润滑油组合物例如可用作内燃机用润滑油、动力传输用润滑油、齿轮油、轴承油、消震器油、工业用润滑油等。
Claims (9)
1.润滑剂用添加剂,含有选自己基硫代乙基磷酸酯、辛基硫代乙基磷酸酯和十二烷基硫代乙基磷酸酯中的至少一种的磷酸酯衍生物(A)与锌化合物(B)的反应物。
3.权利要求2所述的润滑剂用添加剂,上述通式(I)中,Y为O(氧)。
4.权利要求1所述的润滑剂用添加剂,其中,锌化合物(B)为选自金属锌、锌氧化物、有机锌化合物、锌含氧酸盐、氢氧化锌、卤化锌及锌配合物中的至少1种化合物。
5.权利要求4所述的润滑剂用添加剂,其中,锌化合物(B)为选自锌、氧化锌、碳酸锌、二甲基锌、二苯基锌及锌配合物中的至少1种化合物。
6.润滑剂用添加剂组合物,其是配合权利要求1-5中任一项所述的润滑剂用添加剂而成的。
7.润滑油组合物,其特征在于,润滑油基油中含有按磷元素换算量计为0.001-0.5质量%的权利要求1-5中任一项所述的润滑剂用添加剂。
8.内燃机用润滑油组合物,其特征在于,润滑油基油中含有按磷元素换算量计为0.001-0.5质量%的权利要求1-5中任一项所述的润滑剂用添加剂。
9.润滑剂用添加剂的制造方法,其特征在于,由权利要求1所述的磷酸酯衍生物(A)与锌化合物(B)反应而制得。
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JP249807/2004 | 2004-08-30 | ||
JP2004249807A JP4563114B2 (ja) | 2004-08-30 | 2004-08-30 | 潤滑剤用添加剤 |
PCT/JP2005/015400 WO2006025246A1 (ja) | 2004-08-30 | 2005-08-25 | 潤滑剤用添加剤 |
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CN101010418B true CN101010418B (zh) | 2011-07-06 |
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US (1) | US20080161215A1 (zh) |
EP (1) | EP1783196A4 (zh) |
JP (1) | JP4563114B2 (zh) |
KR (1) | KR101252867B1 (zh) |
CN (1) | CN101010418B (zh) |
WO (1) | WO2006025246A1 (zh) |
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CN101668838A (zh) * | 2007-04-26 | 2010-03-10 | 出光兴产株式会社 | 润滑油组合物 |
WO2009061208A1 (en) * | 2007-11-09 | 2009-05-14 | Pronova Biopharma Norge As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
WO2009104682A1 (ja) * | 2008-02-20 | 2009-08-27 | 出光興産株式会社 | 内燃機関用潤滑油組成物 |
EP2147910A1 (en) | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
MA33341B1 (fr) | 2009-05-08 | 2012-06-01 | Pronova Biopharma Norge As | Acides gras polyinsaturés pour le traitement de maladies relatives au domaine des maladies cardiovasculaires, métaboliques et inflammatoires |
JP5498089B2 (ja) * | 2009-08-12 | 2014-05-21 | 国立大学法人北海道大学 | 複合組成物及び光学プラスチック製品 |
JP2011084721A (ja) * | 2009-09-15 | 2011-04-28 | Idemitsu Kosan Co Ltd | 摺動機構 |
DE102010015207A1 (de) * | 2010-04-16 | 2011-10-20 | Schaeffler Technologies Gmbh & Co. Kg | Verfahren zur Überwachung einer Linearführung |
UA111475C2 (uk) | 2010-11-05 | 2016-05-10 | Пронова Байофарма Нордж Ас | Способи лікування із застосуванням ліпідних сполук |
CN103805312A (zh) * | 2012-11-14 | 2014-05-21 | 重庆工商大学 | 一种高效无硫磷多功能润滑添加剂 |
ES2748562T3 (es) | 2013-02-28 | 2020-03-17 | Basf As | Una composición que comprende un compuesto lipídico, un triglicérido y un tensioactivo, y procedimientos de uso de la misma |
JP6247600B2 (ja) * | 2014-06-16 | 2017-12-13 | Jxtgエネルギー株式会社 | 変速機用潤滑油組成物 |
US10000721B2 (en) | 2014-12-30 | 2018-06-19 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
US10781397B2 (en) | 2014-12-30 | 2020-09-22 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
CN107530306A (zh) | 2015-04-28 | 2018-01-02 | 普罗诺瓦生物医药挪威公司 | 结构增强的含硫脂肪酸在预防和/或治疗非酒精性脂肪性肝炎中的用途 |
JP7318164B2 (ja) * | 2016-12-14 | 2023-08-01 | 出光興産株式会社 | 潤滑油組成物、潤滑方法及びギヤ |
SG11202005007VA (en) | 2017-12-06 | 2020-06-29 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
JP7475256B2 (ja) * | 2020-10-09 | 2024-04-26 | Eneos株式会社 | 潤滑油組成物 |
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Also Published As
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US20080161215A1 (en) | 2008-07-03 |
EP1783196A1 (en) | 2007-05-09 |
WO2006025246A1 (ja) | 2006-03-09 |
KR20070048745A (ko) | 2007-05-09 |
JP4563114B2 (ja) | 2010-10-13 |
JP2006063248A (ja) | 2006-03-09 |
KR101252867B1 (ko) | 2013-04-09 |
CN101010418A (zh) | 2007-08-01 |
EP1783196A4 (en) | 2010-07-21 |
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