JP2018035203A - トラクションドライブ用潤滑油基油 - Google Patents
トラクションドライブ用潤滑油基油 Download PDFInfo
- Publication number
- JP2018035203A JP2018035203A JP2016166583A JP2016166583A JP2018035203A JP 2018035203 A JP2018035203 A JP 2018035203A JP 2016166583 A JP2016166583 A JP 2016166583A JP 2016166583 A JP2016166583 A JP 2016166583A JP 2018035203 A JP2018035203 A JP 2018035203A
- Authority
- JP
- Japan
- Prior art keywords
- group
- cyclohexanedicarboxylic acid
- acid
- dimethylundecyl
- base oil
- 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
- 239000002199 base oil Substances 0.000 title claims abstract description 67
- 239000000314 lubricant Substances 0.000 title claims abstract description 13
- -1 alicyclic dicarboxylic acid diester compound Chemical class 0.000 claims abstract description 698
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
- 230000001050 lubricating effect Effects 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 296
- 239000003054 catalyst Substances 0.000 description 56
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 39
- 239000002253 acid Substances 0.000 description 31
- 238000000034 method Methods 0.000 description 29
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000000344 soap Substances 0.000 description 14
- 238000011282 treatment Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000005809 transesterification reaction Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229940077388 benzenesulfonate Drugs 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 239000010953 base metal Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910000510 noble metal Inorganic materials 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920001083 polybutene Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000006078 metal deactivator Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920013636 polyphenyl ether polymer Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
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- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- XUVKLBIJXLIPDZ-UHFFFAOYSA-N (4-cyclohexyl-2-methylpentan-2-yl)cyclohexane Chemical compound C1CCCCC1C(C)CC(C)(C)C1CCCCC1 XUVKLBIJXLIPDZ-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical class C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
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- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- SXSWMAUXEHKFGX-UHFFFAOYSA-N 2,3-dimethylbutan-1-ol Chemical compound CC(C)C(C)CO SXSWMAUXEHKFGX-UHFFFAOYSA-N 0.000 description 2
- MIBBFRQOCRYDDB-UHFFFAOYSA-N 2,3-dimethylpentan-1-ol Chemical compound CCC(C)C(C)CO MIBBFRQOCRYDDB-UHFFFAOYSA-N 0.000 description 2
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- BAYAKMPRFGNNFW-UHFFFAOYSA-N 2,4-dimethylpentan-3-ol Chemical compound CC(C)C(O)C(C)C BAYAKMPRFGNNFW-UHFFFAOYSA-N 0.000 description 2
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-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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- 125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- 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 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Lubricants (AREA)
Abstract
Description
一般式(1)
で表される脂環式ジカルボン酸ジエステルを含有するトラクションドライブ用潤滑油基油。
R1及びR2のうちの少なくとも一方が、主鎖である直鎖状アルキル基とこれに結合した2個若しくは3個以上のメチル基(分枝)とからなる分岐鎖状アルキル基である、[項1]に記載のトラクションドライブ用潤滑油基油。
R1及びR2のうちの少なくとも一方が、3,5,5−トリメチルヘキシル基である、[項1]又は[項2]に記載のトラクションドライブ用潤滑油。
R1及びR2が、3,5,5−トリメチルヘキシル基である、[項1]〜[項3]のいずれかに記載のトラクションドライブ用潤滑油基油。
で表される脂環式ジカルボン酸ジエステルを含有していることを特徴とする。
ブタノール、2,3−ジメチルブタノール、3,3−ジメチルブタノール、3,3−ジメチル−2−ブタノール、4−メチル−2−ペンタノール、4,4−ジメチル−2−ペンタノール、2,4−ジメチル−3−ペンタノール、2,2−ジメチル−3−ヘキサノール、6−メチル−3−ヘプタノール、2−メチル−3−オクタノール、2,4−ジメチル−4−オクタノール、3,5,5−トリメチルヘキサノールが好ましく、特に、3,5,5−トリメチルヘキサノールが好ましい。
ジ(4,4,5−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(3,4,4−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(2,4,4−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,6−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,5−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,4−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(2,3,3−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,6−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,5−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,4−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,3−トリメチルオクチル)、1,4−シクロヘキサンジカルボン酸ジ(9,9―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(8,9―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,9―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,9―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,9―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,9―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,9―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,9―ジメチルデシル),1,4−シクロヘキサンジカルボン酸ジ(8,8―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,8―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,8―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,8―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,8―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,8―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,8―ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,7−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,7−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,7−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,7−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,7−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,7−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,6−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,6−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,6−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,6−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,6−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,5−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,5−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,5−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,5−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,4−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,4−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,4−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,3−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,3−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,2−ジメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,8,8−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(6,8,8−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(5,8,8−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(4,8,8−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,8,8−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,8,8−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(6,7,7−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(5,7,7−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(4,7,7−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,7,7−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,7,7−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(5,6,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(4,6,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,6,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,6,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(5,5,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(4,5,5−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,5,5−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,5,5−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(4,4,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(4,4,5−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,4,4−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,4,4−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,5−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,4−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,3,3−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,6−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,5−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,4−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,3−トリメチルノニル)、1,4−シクロヘキサンジカルボン酸ジ(10,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(9,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(8,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,10―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(9,9―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(8,9―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,9―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,9―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,9―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,9―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,9―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,9―ジメチルウンデシル),1,4−シクロヘキサンジカルボン酸ジ(8,8―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,8―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,8―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,8―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,8―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,8―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,8―ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,7−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,7−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,7−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,7−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,7−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,7−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,6−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,6−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,6−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,6−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,6−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,5−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,5−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,5−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,5−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,4−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,4−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,4−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,3−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,3−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,2−ジメチルウンデシル)、1,4−シクロヘキサンジカルボン酸ジ(8,9,9−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,9,9−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,9,9−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,9,9−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,9,9−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,9,9−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,9,9−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(7,8,8−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,8,8−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,8,8−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,8,8−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,8,8−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,8,8−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(6,7,7−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,7,7−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,7,7−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,7,7−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,7,7−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,6,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,6,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,6,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,6,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(5,5,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,5,5−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,5,5−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,5,5−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4,4,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(4
,4,5−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,4,4−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,4,4−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,5−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(3,3,4−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,3,3−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,6−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,5−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,4−トリメチルデシル)、1,4−シクロヘキサンジカルボン酸ジ(2,2,3−トリメチルデシル)、等が挙げられる。その中でも、1,4−シクロヘキサンジカルボン酸ジ(2,2−ジメチルプロピル)、1,4−シクロヘキサンジカルボン酸ジ(2,2−ジメチルブチル)、1,4−シクロヘキサンジカルボン酸ジ(2,3−ジメチルブチル)、1,4−シクロヘキサンジカルボン酸ジ(3,3−ジメチルブチル)、1,4−シクロヘキサンジカルボン酸ジ(3,3−ジメチル−2−ブチル)、1,4−シクロヘキサンジカルボン酸ジ(4−メチル−2−ペンチル)、1,4−シクロヘキサンジカルボン酸ジ(4,4−ジメチル−2−ペンチル)、1,4−シクロヘキサンジカルボン酸ジ(2,4−ジメチル−3−ペンチル)、1,4−シクロヘキサンジカルボン酸ジ(2,2−ジメチル−3−ヘキシル)、1,4−シクロヘキサンジカルボン酸ジ(6−メチル−3−ヘプチル)、1,4−シクロヘキサンジカルボン酸ジ(2−メチル−3−オクチル)、1,4−シクロヘキサンジカルボン酸ジ(2,4−ジメチル−4−ヘプチル)、1,4−シクロヘキサンジカルボン酸ジ(3,5,5−トリメチルヘキシル)が好ましく、特に、1,4−シクロヘキサンジカルボン酸ジ(3,5,5−トリメチルヘキシル)が好ましい。
1,4−シクロヘキサンジカルボン酸:新日本理化株式会社製 製品名「リカシッド CHDA」
3,5,5−トリメチルヘキサノール:KHネオケム株式会社製 製品名「ノナノール」
2−エチルヘキサノール:KHネオケム株式会社製 製品名「オクタノール」
n−オクタノール:新日本理化株式会社製 製品名「コノール 10WS」
アジピン酸ジイソデシル:新日本理化株式会社製 製品名「サンソサイザー DIDA」
鉱物油Y:SKルブリカンツ製 製品名「YUBASE 3」(飽和炭化水素の工業用流動パラフィン)
<酸価(AV)>
JIS K2501(2003)に準拠して測定した。
JIS K0070(1992)に準拠して測定した。
<トラクション係数>
下記装置および条件にて試験した時の最大トラクション係数を測定し、トラクション係数(60℃)とした。
[測定条件]
装置:ボールオンリング型摩擦試験機(Phoenix Tribology社製TE54型)
試験片形状:上試験片(Φ25mmの球)、下試験片(Φ50mmのリング)
試験片材質:SUJ2
回転速度:1.0〜1.5mm/s
滑り率:0.5〜50%(0.5%毎に変化させた)
試料温度:60℃
荷重:100N
JIS K2283(2000)に準拠して、40℃、100℃における動粘度を測定し、得られた測定値から粘度指数を算出した。
JIS K2269(1987)に準拠して流動点を測定した。
JIS K2265(クリーブランド開放式)に準拠して測定した。
撹拌器、温度計、冷却管付き水分分留受器を備えた2リットルの四ツ口フラスコに脂環式ジカルボン酸として1,4−シクロヘキサンジカルボン酸568.2g(3.3mol)、分岐鎖状アルコールとして3,5,5−トリメチルヘキサノール1047.3g(7.26mol)、エステル化触媒として酸化スズ1.4gを仕込み、フラスコ内を窒素置換した後、徐々に230℃まで昇温した。理論生成水量(118.8g)を目処にして留出してくる生成水を水分分留受器で除去しつつ、3,5,5−トリメチルヘキサノールが還流するように減圧度を調整しながら、エステル化反応を行い、全酸価が0.1mgKOH/g以下となるまで反応を行った。反応終了後、残存する3,5,5−トリメチルヘキサノールを減圧下で蒸留により除去してエステル化粗物を得た。次いで、得られたエステル化粗物の全酸価に対して3倍当量の苛性ソーダ水溶液で中和した後、中性になるまで水洗を繰り返した。得られたエステル化粗物に硫酸マグネシウムを加えて脱水した後、濾過により硫酸マグネシウムを除去して、1,4−シクロヘキサンジカルボン酸ジ(3,5,5−トリメチルヘキシル)1298.2g(3.06mol)を得た。得られた脂環式ジカルボン酸ジエステルの酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該脂環式ジカルボン酸ジエステルをトラクションドライブ用潤滑油基油(A)として評価した際の各物性を表1に示す。
3,5,5−トリメチルヘキサノールを2−エチルヘキサノール945.5g(7.26mol)に変更した以外は実施例1と同様の方法で、1,4−シクロヘキサンジカルボン酸ジ(2−エチルヘキシル)1189.8g(3.00mol)を得た。得られた脂環式ジカルボン酸ジエステルの酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該脂環式ジカルボン酸ジエステルをトラクションドライブ用潤滑油基油(a)として評価した際の各物性を表1に示す。
3,5,5−トリメチルヘキサノールをn−オクタノール945.5g(7.26mol)に変更した以外は実施例1と同様の方法で、1,4−シクロヘキサンジカルボン酸ジ(n−オクチル)1201.2g(3.03mol)を得た。得られた脂環式ジカルボン酸ジエステルの酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該脂環式ジカルボン酸ジエステルをトラクションドライブ用潤滑油基油(b)として評価した際の各物性を表1に示す。
アジピン酸ジイソデシルをトラクションドライブ用潤滑油基油(c)として評価した際の各物性値を表1に示す。
鉱物油Yをトラクションドライブ用潤滑油基油(d)として評価した際の各物性を表1に示す。
Claims (4)
- 一般式(1)
で表される脂環式ジカルボン酸ジエステルを含有するトラクションドライブ用潤滑油基油。 - R1及びR2のうちの少なくとも一方が、主鎖である直鎖状アルキル基とこれに結合した2個若しくは3個以上のメチル基(分枝)とからなる分岐鎖状アルキル基である、請求項1に記載のトラクションドライブ用潤滑油基油。
- R1及びR2のうちの少なくとも一方が、3,5,5−トリメチルヘキシル基である、請求項1又は請求項2に記載のトラクションドライブ用潤滑油基油。
- R1及びR2が、3,5,5−トリメチルヘキシル基である、請求項1〜3のいずれかに記載のトラクションドライブ用潤滑油基油。
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JP2004083917A (ja) * | 1995-12-12 | 2004-03-18 | New Japan Chem Co Ltd | 潤滑油 |
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JP2016108543A (ja) * | 2014-12-08 | 2016-06-20 | 新日本理化株式会社 | トラクションドライブ用基油 |
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JP2004083917A (ja) * | 1995-12-12 | 2004-03-18 | New Japan Chem Co Ltd | 潤滑油 |
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JPWO2020080269A1 (ja) * | 2018-10-19 | 2021-09-09 | 新日本理化株式会社 | 動力伝達用潤滑油基油 |
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