JP2008037860A - リンモリブデン化合物及びその製造方法 - Google Patents
リンモリブデン化合物及びその製造方法 Download PDFInfo
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- JP2008037860A JP2008037860A JP2007101757A JP2007101757A JP2008037860A JP 2008037860 A JP2008037860 A JP 2008037860A JP 2007101757 A JP2007101757 A JP 2007101757A JP 2007101757 A JP2007101757 A JP 2007101757A JP 2008037860 A JP2008037860 A JP 2008037860A
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- Prior art keywords
- phosphomolybdenum
- compound
- acid
- group
- mono
- 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
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- 239000005078 molybdenum compound Substances 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 44
- AMWVZPDSWLOFKA-UHFFFAOYSA-N phosphanylidynemolybdenum Chemical compound [Mo]#P AMWVZPDSWLOFKA-UHFFFAOYSA-N 0.000 title abstract description 14
- -1 phosphorus molybdenum amine Chemical class 0.000 claims abstract description 220
- 239000000203 mixture Substances 0.000 claims abstract description 54
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 49
- 239000010687 lubricating oil Substances 0.000 claims abstract description 45
- 239000002253 acid Substances 0.000 claims abstract description 43
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000011574 phosphorus Substances 0.000 claims abstract description 39
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 38
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 32
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 23
- 239000010452 phosphate Substances 0.000 claims abstract description 22
- 150000002752 molybdenum compounds Chemical class 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims description 26
- 230000002829 reductive effect Effects 0.000 claims description 24
- 239000003638 chemical reducing agent Substances 0.000 claims description 18
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 claims description 18
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 16
- 239000011707 mineral Substances 0.000 claims description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 5
- 239000002518 antifoaming agent Substances 0.000 claims description 4
- 230000007797 corrosion Effects 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 4
- 239000001177 diphosphate Substances 0.000 claims description 4
- 235000011180 diphosphates Nutrition 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 4
- 150000004712 monophosphates Chemical class 0.000 claims description 3
- 229960002317 succinimide Drugs 0.000 claims description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 33
- 239000010705 motor oil Substances 0.000 abstract description 8
- 239000010723 turbine oil Substances 0.000 abstract description 3
- 230000003472 neutralizing effect Effects 0.000 abstract description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 43
- 229910052750 molybdenum Inorganic materials 0.000 description 42
- 239000003921 oil Substances 0.000 description 35
- 239000011733 molybdenum Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 26
- 239000010410 layer Substances 0.000 description 23
- 239000002199 base oil Substances 0.000 description 21
- 235000021317 phosphate Nutrition 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000010755 mineral Nutrition 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 239000010802 sludge Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 10
- 125000004437 phosphorous atom Chemical group 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- HSNVNALJRSJDHT-UHFFFAOYSA-N P(=O)(=O)[Mo] Chemical compound P(=O)(=O)[Mo] HSNVNALJRSJDHT-UHFFFAOYSA-N 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- RYYXDZDBXNUPOG-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCC2=C1SC(N)=N2 RYYXDZDBXNUPOG-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 230000001050 lubricating effect Effects 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000013329 compounding Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 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 6
- 239000007787 solid Substances 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 125000002704 decyl group Chemical group [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])* 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 4
- 239000002530 phenolic antioxidant Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 3
- 239000011609 ammonium molybdate Substances 0.000 description 3
- 235000018660 ammonium molybdate Nutrition 0.000 description 3
- 229940010552 ammonium molybdate Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000002542 deteriorative effect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 3
- 239000010711 gasoline engine oil Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006038 hexenyl group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000001400 nonyl 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])[H] 0.000 description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011684 sodium molybdate Substances 0.000 description 3
- 235000015393 sodium molybdate Nutrition 0.000 description 3
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 3
- 238000003756 stirring Methods 0.000 description 3
- 235000011044 succinic acid Nutrition 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000002889 tridecyl 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])[H] 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-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
- SZAQZZKNQILGPU-UHFFFAOYSA-N 2-[1-(2-hydroxy-3,5-dimethylphenyl)-2-methylpropyl]-4,6-dimethylphenol Chemical compound C=1C(C)=CC(C)=C(O)C=1C(C(C)C)C1=CC(C)=CC(C)=C1O SZAQZZKNQILGPU-UHFFFAOYSA-N 0.000 description 2
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Images
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
- 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
金属を含有する添加剤の中で、最も代替の要望の強いものの一つに亜鉛ジチオホスフェートがある。亜鉛ジチオホスフェートはリン原子と亜鉛原子を含む添加剤であるが、酸化防止性能や耐磨耗性能等を持ち合わせ、多種多様な潤滑油に使用されている。亜鉛ジチオホスフェートが嫌われる原因は、上記のように様々な悪影響を及ぼすからであるが、中でも、自動車のエンジン油に添加すると、排気ガスとともに放出されたリン原子が自動車の排ガス触媒に付着し、触媒の活性を低下させることが大きな問題になっている。触媒の活性が低下すると、排ガスに含まれる窒素酸化物や硫黄酸化物等の有害な物質が、排ガス触媒で分解されずに大気中へ放出されてしまう。
しかし、亜鉛ジチオホスフェートの添加量を一定量以下に減らすと、潤滑油の酸化防止性能が極端に悪くなるため、亜鉛ジチオホスフェートの添加量を一定量以下に減らすことはできなかった。また、亜鉛ジチオホスフェートを減らすかわりに、フェーノール系酸化防止剤やアミン系酸化防止剤等の酸化防止剤を増量すると、潤滑油が劣化していく過程で潤滑油中のスラッジが増えてしまうため、これらの酸化防止剤の添加量を増やして対応することもできなかった。
また、特許文献3に記載されている油溶性モリブデン化合物は、6価のモリブデン化合物を還元剤で還元した後、酸性のリン化合物と反応させ、その後鉱酸で中和するものであるが、本発明のリンモリブデン化合物の製造方法により得られたリンモリブデン化合物とは本質的な異なる化合物である。
即ち、本発明は、下記の一般式(1)
で表されることを特徴とするリンモリブデン化合物にある。
ここで、本発明のリンモリブデン化合物の製造方法に使用できる6価のモリブデン化合物としては、例えば、三酸化モリブデン又はその水和物(MoO3・nH2O)、モリブデン酸(H2MoO4)、モリブデン酸ナトリウム、モリブデン酸カリウム等のモリブデン酸金属塩(M2MoO4;Mは金属原子)、モリブデン酸アンモニウム[(NH4)2MoO4又は(NH4)6(Mo7O24)・4H2O]、MoOCl4、MoO2Cl2、MoO2Br2、Mo2O3Cl6等が挙げられるが、入手しやすい三酸化モリブデン又はその水和物、モリブデン酸金属塩、モリブデン酸アンモニウム等が好ましい。
ここで、アルキル基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、2級ブチル、ターシャリブチル、ペンチル、イソペンチル、2級ペンチル、ネオペンチル、ターシャリペンチル、ヘキシル、2級ヘキシル、ヘプチル、2級ヘプチル、オクチル、2−エチルヘキシル、2級オクチル、ノニル、2級ノニル、デシル、2級デシル、ウンデシル、2級ウンデシル、ドデシル、2級ドデシル、トリデシル、イソトリデシル、2級トリデシル、テトラデシル、2級テトラデシル、ヘキサデシル、2級ヘキサデシル、ステアリル、エイコシル、ドコシル、テトラコシル、トリアコンチル、2−ブチルオクチル、2−ブチルデシル、2−ヘキシルオクチル、2−ヘキシルデシル、2−オクチルデシル、2−ヘキシルドデシル、2−オクチルドデシル、2−デシルテトラデシル、2−ドデシルヘキサデシル、2−ヘキサデシルオクタデシル、2−テトラデシルオクタデシル、モノメチル分枝−イソステアリル等が挙げられる。
実施例1(リンモリブデン化合物1の製造例)
窒素導入管、還流管、撹拌装置及び温度計を備えた3000mlフラスコに、モリブデン酸ソーダ2水和物1モル(242g)に水206g加えて溶解させた後、窒素気流下50〜60℃で二酸化チオ尿素0.5モル(54g)を添加して1時間反応させた。次いで2モルの20%硫酸(980g)を1時間で滴下し、さらに2時間熟成させた。熟成後30〜40℃に冷却し、1モルのジオレイルリン酸エステル(598g)を1時間で滴下し、更に10時間反応させた。得られた反応物にn−ヘキサン300mlを加えて30分撹拌し、その後1時間放置して水層と油層の2層に分離させて水層を除去した。最後に得られた油層を減圧下で脱溶媒し、濃褐色オイル状生成物(リンモリブデン化合物1)711gを得た。得られた濃褐色オイル状生成物を分析した結果、モリブデン含量は12.2%であり、リン含量は4.2%であった。モリブデンについての収率は90%であった。
実施例1と同様の方法で、1モルのジオレイルリン酸エステルの代わりに、0.5モルのモノオクチルリン酸エステルと0.5モルのジオクチルリン酸エステルとの混合物を、0.5モルの二酸化チオ尿素の代わりに0.17モルのハイドロサルファイトを使用し、濃青色オイル状生成物(リンモリブデン化合物2)568gを得た。モリブデン含有量は21.0%であり、リン含量は7.2%であった。モリブデンについての収率は88%であった。
実施例1と同様の反応装置を使用し、三酸化モリブデン1モル(144g)に水144g加え、窒素気流下で50〜60℃に昇温し、1モルの20%苛性ソーダ(200g)を1時間で滴下し、1時間熟成させた。熟成後、二酸化チオ尿素0.5モル(54g)を添加して1時間反応させた。次いで2モルの20%硫酸(980g)を1時間で滴下し、さらに2時間熟成させた。40〜50℃に冷却し、0.5モルのモノオクチルリン酸エステルと0.5モルのジオクチルリン酸エステルとの混合物(266g)を1時間で滴下し、10時間反応させた。n−ヘキサン300mlを加えて30分撹拌し、その後1時間放置して水層と油層の2層に分離させて水層を除去した。最後に得られた油層を減圧下で脱溶媒を行い、濃褐色オイル状生成物(リンモリブデン化合物3)401gを得た。モリブデン含有量は22.5%であり、リン含量は7.7%であった。モリブデンについての収率は94%であった。
実施例3と同様の方法で、0.5モルのモノオクチルリン酸エステルと0.5モルのジオクチルリン酸エステルとの混合物の代わりに、1モルのジオクチルリン酸エステルを使用し、濃褐色オイル状生成物(リンモリブデン化合物4)440gを得た。モリブデン含有量は20.1%であり、リン含量は6.9%であった。モリブデンについての収率は92%であった。
実施例3と同様の方法で、0.5モルのモノオクチルリン酸エステルと0.5モルのジオクチルリン酸エステルとの混合物の代わりに、1モルのモノオレイルリン酸エステルを使用し、濃褐色オイル状生成物(リンモリブデン化合物5)340gを得た。モリブデン含有量は26.3%であり、リン含量は9.1%であった。モリブデンについての収率は93%であった。
実施例3と同様の方法で、0.5モルのモノオクチルリン酸エステルと0.5モルのジオクチルリン酸エステルとの混合物の代わりに、0.5モルのモノ−4−イソプロピルフェニルリン酸エステルと0.5モルのジ−4−イソプロピルフェニルリン酸エステルの混合物を使用し、濃褐色オイル状生成物(リンモリブデン化合物6)401gを得た。モリブデン含有量は22.2%であり、リン含量は7.6%であった。モリブデンについての収率は93%であった。
実施例3と同様の方法で、二酸化チオ尿素の量を2モルに増量して同様の反応を行い、濃褐色オイル状生成物(リンモリブデン化合物7)395gを得た。モリブデン含有量は22.6%であり、リン含量は7.7%であった。モリブデンについての収率は93%であった。
実施例1で得られたリンモリブデン化合物1(711g)と2モルのモノオレイルアミン(534g)を60〜70℃で4時間反応させた。更に2.3〜1.3kPaの減圧下で1時間攪拌し、濃青色オイル状生成物(リンモリブデン化合物化合物1)1224gを得た。モリブデン含量は7.0%であり、リン含量は2.4%であった。モリブデンについての収率は99%であった。
実施例3で得られたリンモリブデン化合物3(401g)と1モルのジオクチルアミン(241g)を60〜70℃で4時間反応させた。更に2.3〜1.3kPaの減圧下で1時間攪拌し、濃褐色オイル状生成物(リンモリブデンアミン化合物2)631gを得た。モリブデン含量は14.2%であり、リン含量は4.9%であった。モリブデンについての収率は99%であった。
実施例4で得られたリンモリブデン化合物4(440g)と1.2モルのアルケニルモノコハク酸ポリイミド(737g)を60〜70℃で4時間反応させた。更に2.3〜1.3kPaの減圧下で1時間攪拌し、濃褐色オイル状生成物(リンモリブデンアミン化合物3)1153gを得た。モリブデン含量は7.5%であり、リン含量は2.6%であった。モリブデンについての収率は98%であった。
窒素導入管、還流管、撹拌装置及び温度計を備えた3000mlフラスコに、モリブデン酸ソーダ1モル(206g)に水206g加えて溶解させた後、窒素気流下50〜60℃で二酸化チオ尿素0.5モルを添加し、1時間反応させた。30〜40℃に冷却し、2モルのジオクチルリン酸エステル(644g)を1時間で滴下し、さらに1モルの20%硫酸を1時間で滴下した。その後温度を100℃まで上昇させ、10時間反応させた。n−ヘキサン300mlを加えて30分撹拌し、その後1時間放置して水層と油層の2層に分離させて水層を除去した。最後に得られた油層を減圧下で脱溶媒し、濃青色オイル状生成物(比較品1)437gを得た。得られた濃褐色オイル状生成物を分析した結果、モリブデン含量は19.5%であり、リン含量は13.5%であった。モリブデンについての収率は89%であった。
比較例1と同様の方法で、0.5モルの二酸化チオ尿素の代わりに0.17モルのハイドロサルファイト、2モルのジオクチルリン酸エステルの代わりに0.5モルのモノオクチルリン酸エステルと0.5モルのジオクチルリン酸エステルとの混合物を使用し、濃青色オイル状生成物(比較品2)359gを得た。モリブデン含有量は16.6%であり、モリブデンについての収率は62%であった。リン含量は8.1%であった。
リンモリブデン化合物2 :Mo含量21.0質量%、リン含量7.2質量%
比較品2 :Mo含量16.6質量%、リン含量8.1質量%
この結果から、リンモリブデン化合物2と比較品2は異なるものであることが確認された。
上述のようにして得られた本発明品のリンモリブデン化合物4について、n−ヘキサン及び水を使用して水洗を3回繰り返して行った後、減圧にて脱溶媒して精製度を高めたリンモリブデン化合物4を使用して、構造解析を行った:
<元素分析>
C:42.6%、H:7.6%、Mo:21.4%、P:6.9%
ここで、精製前と精製後のリンモリブデン化合物4の分析値を比較すると、精製後のリンモリブデン化合物4において、モリブデン含量が増加している。これは、モリブデン原子と結合していない酸性リン酸エステルが精製により除去され、化合物の全量が減少し、相対的にモリブデン含量が増加し、また、精製により未結合の酸性リン酸性エステル中のリン原子は除去されるので、リン含量には変化がないものと推測される。上記元素分析の結果から、モリブデン原子とリン原子は等モルで存在していることが確認できる。モリブデン原子とリン原子が等モルで、モリブデン原子は5価に還元されていることから、以下の構造が基本骨格を成していると考えられる。
TOF−MS分析は、飛行時間型質量分析装置によるものであり、試料をイオン化して一定距離飛行させ、その飛行時間を測定することによって分子量を求めるものである。TOF−MS分析装置として、Perseptive Biosystems社のVayager-DE STRを使用してリンモリブデン化合物4の分子量を測定した。試料は、以下の溶液3種類を混合して使用した:
(1)リンモリブデン化合物4の1%THF溶液:2μl
(2)ジスラノール(マトリックス物質:1,8−ジヒドロキシ−9,10−ジヒドロア ントラセン−9−オン)の1%THF溶液:20μl
(3)トリフルオロ酢酸カリウム:0.05μl
なお、(3)を入れると、リンモリブデン化合物4にカリウムの分子量が加算されたピークが表れる。これにより、誤ピークかどうかを確認することができる。得られたチャートを図3及び4に示す。
モリブデン原子には同位体が多く、それらの同位体の中でも存在比が突出して多いものはない。主な原子量とその割合は以下の通りである:
92:14.84%、94:9.25%、95:15.92%、96:16.68%、97:9.55%、98:24.13%
TOF−MS分析は、分子量が1違っていても異なるピークとして認識するため、モリブデンを含む化合物のチャートでは、分子量が1づつ細かく分かれたピークが出現する。図3に示すチャートは、TOF−MS分析の結果であるが、これらのピークを細かく見ていくと、モリブデン特有のピークは分子量1800前後にしかなかった。それ以上大きな分子量のピークもないことから、これが分析したリンモリブデン化合物4であると考えられる。なお、分子量の低いところに表れているピークは、リンモリブデン化合物4が分解したリン酸エステル等のピークである。
図4に示すチャートは、図3に示すチャートの分子量1800前後を拡大したものである。モリブデン原子特有のピーク集団が2つ見られるが、2つの集団の分子量差が39であることから、右側の集団は左側の集団にカリウムが付加されたものであることが判る。よって、左側の集団がリンモリブデン化合物4の分子量である。
左側の集団の一番大きなピークの分子量は約1797であるが、これは元素分析より得られた基本骨格の分子量のちょうど4倍にあたる。基本骨格を4つ繋げると、モリブデン原子は酸素原子と交互に環を巻くことになり、結果的に下記の構造となる:
(リン含量8.2%、一般式(3)におい、てR1=n−ブチル、R2=1−オクチル、a=0.2)
化合物12:p,p’−ジドデシルジフェニルアミン
化合物13:3−(4−ヒドロキシ−3,5−ジ−t−ブチルフェニル)プロピオン酸オ クチル
上記リンモリブデン化合物1〜7、リンモリブデンアミン化合物8〜10、比較品1〜2、化合物11(亜鉛ジチオホスフェート)の二次酸化防止性能を以下の方法にて評価した。ガラス製内筒管の入った100mlのオートクレーブに、トルエン37.5g、クメンハイドロパーオキサイド(以下CHPと略す)2.5g、上記化合物をリン含量で50質量ppmになるように入れて密閉した。オートクレーブを70℃の振とう恒温槽に入れて70回/分にて振とうさせ、4時間後にサンプリングし、過酸化物価を測定してCHPの残量を分析した。CHP残量は、最初に添加したCHPに対するパーセンテージで表わした。また、化合物が二次酸化防止剤として働いた結果による生成物であるフェノール量をガスクロマトグラフィーにより定量した。始めに添加したクメンハイドロパーオキサイド全量がイオン分解することにより生成したフェノール量を100%とし、それに対するパーセンテージで示した。結果を表1に示す。
CHPは、イオン分解によりフェノールを生成し、ラジカル分解により各種ラジカルを経てクミルアルコールやアセトフェノン等を生成する。ラジカルの生成は酸化防止という観点において好ましくないため、フェノールの生成が多いほど酸化防止剤の性能が良いことを示す。
動粘度4.24mm2/秒(100℃)、19.65mm2/秒(40℃)、粘度指数=126の鉱物油系高度VI油に、上記の化合物をMo含量として100質量ppmになるように溶解させ、JIS K 2514−1993「潤滑油−酸化安定度試験方法」の4.に規定するISOT試験に準拠して、試験油を劣化させた。試験は、触媒として銅板と鉄板を入れたガラス容器に試験油を250ml入れ、1300rpmで空気を巻き込むよう攪拌しながら、165.5℃で168時間加熱して試験油を酸化劣化させた。試験終了後、試験油を全てろ紙でろ過して発生したスラッジを濾別し、トルエンでスラッジを洗浄・乾燥して、発生したスラッジの重さを測定した。結果を表1に示す。
ガラス製内筒管に基油5gに対して、上記化合物を表2の組み合わせで添加し、攪拌して分散・溶解させた後、100mlのオートクレーブにセットし、圧力センサー及び排気管の取り付けてある蓋で密閉した。真空ポンプを利用してオートクレーブ内の空気を排気管から排出し、代わりに酸素を入れ、オートクレーブ内を100%酸素雰囲気下にし、同時に圧力を101kPaにした。このオートクレーブを160℃の恒温槽に入れて1時間おきに圧力をチェックし、圧力が80kPaを切るまでの時間を酸化誘導期間として測定した。酸化劣化が進むと酸素が消費されて圧力が減少するので、酸化誘導期間が長いほど良好な酸化防止性能を持つと判断できる。結果を表2に示した。
なお、使用した基油は、上記<スラッジ量の測定>で使用した鉱物油系高度VI油と同じものである。
ガソリンエンジン油組成物(ベースオイルA及びB)、ディーゼルエンジン油組成物(ベースオイルC)を配合し、それぞれの油100質量部に対して、表4に示した量の上記化合物を溶解させた。得られた試験油で実施例2と同様のISOT試験を行って酸化劣化させ、劣化油の全酸価の増加(劣化油の全酸価から劣化前の試験油の全酸価を引いた値)を求めた。全酸価の増加が少ないものほど酸化安定性が高いことを示し、本試験で全酸価の増加が10mgKOH/gを超えると、通常のエンジン油としての使用は困難である。ガソリンエンジン油組成物およびディーゼルエンジン油組成物の配合を表3に、試験結果を表4に示した。なお、使用した基油は、実施例2で使用した鉱物油系高度VI油と同じものである。
Claims (12)
- pが、2である、請求項1記載のリンモリブデン化合物。
- 請求項1又は2に記載のリンモリブデン化合物の製造方法において、6価のモリブデン化合物を還元剤で還元し、それを鉱酸で中和した後、酸性リン酸エステルと反応させることを特徴とするリンモリブデン化合物の製造方法。
- 酸性リン酸エステルは、炭素数4〜18のアルキル基を持つモノリン酸エステル及び/又はジリン酸エステルである、請求項3に記載のリンモリブデン化合物の製造方法。
- 請求項1又は2に記載のリンモリブデン化合物とアミン化合物とを反応させることを特徴とするリンモリブデンアミン化合物の製造方法。
- アミン化合物は、脂肪族アミン又はN置換アルキル(アルケニル)コハク酸イミドである、請求項5に記載のリンモリブデンアミン化合物の製造方法。
- 請求項5又は6に記載のリンモリブデンアミン化合物の製造方法により得られたリンモリブデンアミン化合物。
- 請求項1又は2に記載のリンモリブデン化合物及び/又は請求項7に記載のリンモリブデンアミン化合物を含有することを特徴とする潤滑油組成物。
- 更に、亜鉛ジチオホスフェートを含有する、請求項8に記載の潤滑油組成物。
- 更に、フェノール系及び/又はアミン系酸化防止剤を含有する、請求項8又は9に記載の潤滑油組成物。
- 更に、摩擦低減剤、極圧剤、油性向上剤、清浄剤、分散剤、粘度指数向上剤、流動点降下剤、防錆剤、腐食防止剤及び消泡剤からなる群から選択される1種または2種以上を含有する、請求項8ないし10のいずれか1項に記載の潤滑油組成物。
- リン含量が800質量ppm以下である、請求項8ないし11のいずれか1項に記載の潤滑油組成物。
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CN115960660A (zh) * | 2021-10-08 | 2023-04-14 | 中国石油化工股份有限公司 | 汽油发动机润滑油组合物及其制备方法 |
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WO2018139326A1 (ja) | 2017-01-26 | 2018-08-02 | 東ソー株式会社 | アルカノールアミン、摩擦低減剤、及び潤滑油組成物 |
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CN115960660A (zh) * | 2021-10-08 | 2023-04-14 | 中国石油化工股份有限公司 | 汽油发动机润滑油组合物及其制备方法 |
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EP2039698A4 (en) | 2012-05-09 |
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