JP6434800B2 - αオレフィンの吸着阻害潤滑剤組成物及び吸着阻害方法並びに吸着阻害剤 - Google Patents
αオレフィンの吸着阻害潤滑剤組成物及び吸着阻害方法並びに吸着阻害剤 Download PDFInfo
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- JP6434800B2 JP6434800B2 JP2014254765A JP2014254765A JP6434800B2 JP 6434800 B2 JP6434800 B2 JP 6434800B2 JP 2014254765 A JP2014254765 A JP 2014254765A JP 2014254765 A JP2014254765 A JP 2014254765A JP 6434800 B2 JP6434800 B2 JP 6434800B2
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- olefin
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- 239000000203 mixture Substances 0.000 title claims description 77
- 239000004711 α-olefin Substances 0.000 title claims description 64
- 239000000314 lubricant Substances 0.000 title claims description 51
- 239000003112 inhibitor Substances 0.000 title claims description 18
- 238000001179 sorption measurement Methods 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 9
- 230000002401 inhibitory effect Effects 0.000 title claims description 7
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 28
- 239000002199 base oil Substances 0.000 claims description 22
- 108010077895 Sarcosine Proteins 0.000 claims description 21
- 229940043230 sarcosine Drugs 0.000 claims description 21
- 150000001509 aspartic acid derivatives Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229920002367 Polyisobutene Polymers 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 62
- 230000000052 comparative effect Effects 0.000 description 37
- 239000000654 additive Substances 0.000 description 31
- 230000000996 additive effect Effects 0.000 description 30
- 230000003647 oxidation Effects 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 15
- 230000003449 preventive effect Effects 0.000 description 15
- 230000002265 prevention Effects 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 12
- -1 cyclohexyloxypropyl group Chemical group 0.000 description 12
- 239000011575 calcium Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 229910052791 calcium Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000003443 succinic acid derivatives Chemical class 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 230000000694 effects Effects 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000010725 compressor oil Substances 0.000 description 4
- 239000010720 hydraulic oil Substances 0.000 description 4
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 4
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920013639 polyalphaolefin Polymers 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000006231 alkoxy propyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NISAHDHKGPWBEM-UHFFFAOYSA-N 2-(4-nonylphenoxy)acetic acid Chemical compound CCCCCCCCCC1=CC=C(OCC(O)=O)C=C1 NISAHDHKGPWBEM-UHFFFAOYSA-N 0.000 description 1
- BITAPBDLHJQAID-KTKRTIGZSA-N 2-[2-hydroxyethyl-[(z)-octadec-9-enyl]amino]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCN(CCO)CCO BITAPBDLHJQAID-KTKRTIGZSA-N 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- DIOYAVUHUXAUPX-KHPPLWFESA-N Oleoyl sarcosine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CC(O)=O DIOYAVUHUXAUPX-KHPPLWFESA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VBIGULIJWJPALH-UHFFFAOYSA-L calcium;2-carboxyphenolate Chemical class [Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O VBIGULIJWJPALH-UHFFFAOYSA-L 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000013535 sea water 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
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
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- 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
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- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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- C10M2203/1025—Aliphatic fractions used as base material
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- C10M2205/026—Butene
- C10M2205/0265—Butene used as base material
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- 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
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- 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
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/24—Epoxidised acids; Ester derivatives thereof
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
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- 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
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/12—Partial amides of polycarboxylic acids
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- 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
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- 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
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
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- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014254765A JP6434800B2 (ja) | 2014-12-17 | 2014-12-17 | αオレフィンの吸着阻害潤滑剤組成物及び吸着阻害方法並びに吸着阻害剤 |
| PCT/EP2015/079638 WO2016096753A1 (en) | 2014-12-17 | 2015-12-14 | α-OLEFIN ADSORPTION INHIBITING LUBRICANT COMPOSITION, ADSORPTION INHIBITING METHOD AND ADSORPTION INHIBITOR |
| RU2017124359A RU2708248C2 (ru) | 2014-12-17 | 2015-12-14 | Смазочная композиция, ингибирующая адсорбцию альфа-олефина, способ ингибирования адсорбции и ингибитор адсорбции |
| US15/536,155 US20170369812A1 (en) | 2014-12-17 | 2015-12-14 | Lubricant composition inhibiting adsorption of alpha-olefin, and method and agent for inhibiting adsorption of alpha-olefin |
| CN201580068284.0A CN107109291B (zh) | 2014-12-17 | 2015-12-14 | α-烯烃吸附抑制性润滑剂组合物、吸附抑制方法及吸附抑制剂 |
| EP15816713.0A EP3242924B1 (en) | 2014-12-17 | 2015-12-14 | Alpha-olefin adsorption inhibiting lubricant composition, adsorption inhibiting method and adsorption inhibitor |
| BR112017012882-9A BR112017012882B1 (pt) | 2014-12-17 | 2015-12-14 | Método para inibir adsorção de a-olefina presente em uma composição lubrificante a uma superfície de metal |
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| JP2014254765A JP6434800B2 (ja) | 2014-12-17 | 2014-12-17 | αオレフィンの吸着阻害潤滑剤組成物及び吸着阻害方法並びに吸着阻害剤 |
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| JP2016113572A JP2016113572A (ja) | 2016-06-23 |
| JP6434800B2 true JP6434800B2 (ja) | 2018-12-05 |
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| JP6856296B2 (ja) * | 2016-03-31 | 2021-04-07 | 出光興産株式会社 | 潤滑油組成物、及び金属加工方法 |
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| JPH04166931A (ja) * | 1990-10-31 | 1992-06-12 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| RU2275387C2 (ru) * | 2001-09-14 | 2006-04-27 | Кромптон Корпорейшн | Диспергатор-добавка, улучшающая индекс вязкости, и способ ее получения |
| US7045055B2 (en) * | 2004-04-29 | 2006-05-16 | Chevron U.S.A. Inc. | Method of operating a wormgear drive at high energy efficiency |
| US20060211581A1 (en) * | 2005-03-17 | 2006-09-21 | Bullock Charles L Jr | Blend comprising group III and group IV basestocks |
| DE102005035277B4 (de) * | 2005-07-28 | 2007-10-11 | Clariant Produkte (Deutschland) Gmbh | Mineralöle mit verbesserter Leitfähigkeit und Kältefließfähigkeit |
| EP2041250A1 (en) * | 2006-07-19 | 2009-04-01 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition |
| JP5237562B2 (ja) * | 2007-01-23 | 2013-07-17 | 昭和シェル石油株式会社 | セラミックス球転がり軸受用潤滑油組成物 |
| JP5426829B2 (ja) * | 2007-02-07 | 2014-02-26 | 昭和シェル石油株式会社 | 油圧シリンダーのビビリ、振動、鳴き防止用潤滑油組成物 |
| JP5475984B2 (ja) * | 2007-12-12 | 2014-04-16 | 昭和シェル石油株式会社 | 潤滑油組成物 |
| US7943807B2 (en) * | 2008-02-06 | 2011-05-17 | Chemtura Corporation | Controlling branch level and viscosity of polyalphaolefins with propene addition |
| JP5366416B2 (ja) * | 2008-02-29 | 2013-12-11 | Ｊｘ日鉱日石エネルギー株式会社 | さび止め油組成物 |
| US8530712B2 (en) * | 2009-12-24 | 2013-09-10 | Exxonmobil Chemical Patents Inc. | Process for producing novel synthetic basestocks |
| JP5892800B2 (ja) * | 2012-02-06 | 2016-03-23 | Ｊｘ日鉱日石エネルギー株式会社 | 油圧作動油組成物 |
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|---|---|
| RU2017124359A3 (pt) | 2019-06-14 |
| JP2016113572A (ja) | 2016-06-23 |
| RU2708248C2 (ru) | 2019-12-05 |
| BR112017012882A2 (pt) | 2019-11-19 |
| US20170369812A1 (en) | 2017-12-28 |
| CN107109291A (zh) | 2017-08-29 |
| EP3242924B1 (en) | 2020-09-16 |
| WO2016096753A1 (en) | 2016-06-23 |
| CN107109291B (zh) | 2021-03-09 |
| RU2017124359A (ru) | 2019-01-17 |
| BR112017012882B1 (pt) | 2021-06-01 |
| EP3242924A1 (en) | 2017-11-15 |
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