JP7368737B2 - 動力伝達用潤滑油基油 - Google Patents
動力伝達用潤滑油基油 Download PDFInfo
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- JP7368737B2 JP7368737B2 JP2020553136A JP2020553136A JP7368737B2 JP 7368737 B2 JP7368737 B2 JP 7368737B2 JP 2020553136 A JP2020553136 A JP 2020553136A JP 2020553136 A JP2020553136 A JP 2020553136A JP 7368737 B2 JP7368737 B2 JP 7368737B2
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- JP
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- Prior art keywords
- methyl
- base oil
- group
- power transmission
- acid
- Prior art date
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- 239000002199 base oil Substances 0.000 title claims description 120
- 230000005540 biological transmission Effects 0.000 title claims description 86
- 239000000314 lubricant Substances 0.000 title claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 74
- -1 Aliphatic diols Chemical group 0.000 claims description 72
- 230000001050 lubricating effect Effects 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 24
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 22
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 17
- OJRJDENLRJHEJO-UHFFFAOYSA-N 2,4-diethylpentane-1,5-diol Chemical compound CCC(CO)CC(CC)CO OJRJDENLRJHEJO-UHFFFAOYSA-N 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000003138 primary alcohols Chemical class 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 37
- 239000002253 acid Substances 0.000 description 33
- 239000010687 lubricating oil Substances 0.000 description 22
- 230000000704 physical effect Effects 0.000 description 21
- 239000000344 soap Substances 0.000 description 17
- CIFSKZDQGRCLBN-UHFFFAOYSA-N 3-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCCC(C(O)=O)C1 CIFSKZDQGRCLBN-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000002562 thickening agent Substances 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VSKXJRZPVDLHFY-UHFFFAOYSA-N 2-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCCCC1C(O)=O VSKXJRZPVDLHFY-UHFFFAOYSA-N 0.000 description 6
- BENPUORLYFCUJH-UHFFFAOYSA-N 2-methylheptane-1,7-diol Chemical group OCC(C)CCCCCO BENPUORLYFCUJH-UHFFFAOYSA-N 0.000 description 6
- QTDXSEZXAPHVBI-UHFFFAOYSA-N 4-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)CC1 QTDXSEZXAPHVBI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- HYFFNAVAMIJUIP-UHFFFAOYSA-N 2-ethylpropane-1,3-diol Chemical group CCC(CO)CO HYFFNAVAMIJUIP-UHFFFAOYSA-N 0.000 description 5
- KCNMSJPBWBWPAF-UHFFFAOYSA-N 3-methylheptane-1,7-diol Chemical group OCCC(C)CCCCO KCNMSJPBWBWPAF-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- ZJWDJIVISLUQQZ-UHFFFAOYSA-N 2,4-dimethylpentane-1,5-diol Chemical group OCC(C)CC(C)CO ZJWDJIVISLUQQZ-UHFFFAOYSA-N 0.000 description 4
- IUXBZQXVNRAPJS-UHFFFAOYSA-N 2-ethylheptane-1,7-diol Chemical group CCC(CO)CCCCCO IUXBZQXVNRAPJS-UHFFFAOYSA-N 0.000 description 4
- OPVAJFQBSDUNQA-UHFFFAOYSA-N 3,4-dimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C OPVAJFQBSDUNQA-UHFFFAOYSA-N 0.000 description 4
- HQZRFFDOIJVEFB-UHFFFAOYSA-N 3,4-dimethylcyclohexane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)CC1C HQZRFFDOIJVEFB-UHFFFAOYSA-N 0.000 description 4
- IBKKIFZBAGGCTR-UHFFFAOYSA-N 3,5-dimethylcyclohexane-1-carboxylic acid Chemical compound CC1CC(C)CC(C(O)=O)C1 IBKKIFZBAGGCTR-UHFFFAOYSA-N 0.000 description 4
- FDSDHQKRZOBZLX-UHFFFAOYSA-N 3-ethylpentane-1,5-diol Chemical group OCCC(CC)CCO FDSDHQKRZOBZLX-UHFFFAOYSA-N 0.000 description 4
- FNQSPTROLMILOY-UHFFFAOYSA-N C(C)C(CCO)CCCCO Chemical group C(C)C(CCO)CCCCO FNQSPTROLMILOY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- AZJYMKSURIMUHG-UHFFFAOYSA-N [2-ethyl-4-[(2-methylcyclohexanecarbonyl)oxymethyl]hexyl] 2-methylcyclohexane-1-carboxylate Chemical compound CCC(CC(CC)COC(=O)C1CCCCC1C)COC(=O)C2CCCCC2C AZJYMKSURIMUHG-UHFFFAOYSA-N 0.000 description 4
- LISHGZCECKGAGT-UHFFFAOYSA-N [2-ethyl-4-[(4-methylcyclohexanecarbonyl)oxymethyl]hexyl] 4-methylcyclohexane-1-carboxylate Chemical compound CCC(CC(CC)COC(=O)C1CCC(CC1)C)COC(=O)C2CCC(CC2)C LISHGZCECKGAGT-UHFFFAOYSA-N 0.000 description 4
- YCRZWXZOJROHCO-UHFFFAOYSA-N [2-methyl-3-(3-methylcyclohexanecarbonyl)oxypropyl] 3-methylcyclohexane-1-carboxylate Chemical compound CC1CCCC(C1)C(=O)OCC(C)COC(=O)C2CCCC(C2)C YCRZWXZOJROHCO-UHFFFAOYSA-N 0.000 description 4
- MOBMYAJBILUNQJ-UHFFFAOYSA-N [3-methyl-5-(4-methylcyclohexanecarbonyl)oxypentyl] 4-methylcyclohexane-1-carboxylate Chemical compound CC1CCC(CC1)C(=O)OCCC(C)CCOC(=O)C2CCC(CC2)C MOBMYAJBILUNQJ-UHFFFAOYSA-N 0.000 description 4
- CDQPXFOAMUDLFN-UHFFFAOYSA-N [4-(cyclohexanecarbonyloxymethyl)-2-ethylhexyl] cyclohexanecarboxylate Chemical compound CCC(CC(CC)COC(=O)C1CCCCC1)COC(=O)C2CCCCC2 CDQPXFOAMUDLFN-UHFFFAOYSA-N 0.000 description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 4
- LKXGYGYFPTZHLC-UHFFFAOYSA-N bicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1CC2CCC1(C(=O)O)C2 LKXGYGYFPTZHLC-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 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
- 239000000047 product Substances 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- DYHGIZFXHVQIEA-UHFFFAOYSA-N 2-methylhexane-1,6-diol Chemical group OCC(C)CCCCO DYHGIZFXHVQIEA-UHFFFAOYSA-N 0.000 description 3
- GQSJKULLLUNPMA-UHFFFAOYSA-N 2-methylnonane-1,9-diol Chemical group OCC(C)CCCCCCCO GQSJKULLLUNPMA-UHFFFAOYSA-N 0.000 description 3
- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical group OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 3
- AAAWJUMVTPNRDT-UHFFFAOYSA-N 2-methylpentane-1,5-diol Chemical group OCC(C)CCCO AAAWJUMVTPNRDT-UHFFFAOYSA-N 0.000 description 3
- SQAJRDHPLTWZQT-UHFFFAOYSA-N 3-methylhexane-1,6-diol Chemical group OCCC(C)CCCO SQAJRDHPLTWZQT-UHFFFAOYSA-N 0.000 description 3
- CLILDWHSGQDKNC-UHFFFAOYSA-N 3-methylnonane-1,9-diol Chemical group OCCC(C)CCCCCCO CLILDWHSGQDKNC-UHFFFAOYSA-N 0.000 description 3
- ACWBYVIQVCTYBJ-UHFFFAOYSA-N 3-methyloctane-1,8-diol Chemical group OCCC(C)CCCCCO ACWBYVIQVCTYBJ-UHFFFAOYSA-N 0.000 description 3
- ZFHZIIQASZBGGD-UHFFFAOYSA-N 4-methylheptane-1,7-diol Chemical group OCCCC(C)CCCO ZFHZIIQASZBGGD-UHFFFAOYSA-N 0.000 description 3
- AQYPYBYQBJVBGF-UHFFFAOYSA-N 4-methylnonane-1,9-diol Chemical group OCCCC(C)CCCCCO AQYPYBYQBJVBGF-UHFFFAOYSA-N 0.000 description 3
- DMIUMZKUIYPNLB-UHFFFAOYSA-N 4-methyloctane-1,8-diol Chemical group OCCCC(C)CCCCO DMIUMZKUIYPNLB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- UGVROSKLLNISKC-UHFFFAOYSA-N [2-ethyl-4-[(3-methylcyclohexanecarbonyl)oxymethyl]hexyl] 3-methylcyclohexane-1-carboxylate Chemical compound CCC(CC(CC)COC(=O)C1CCCC(C1)C)COC(=O)C2CCCC(C2)C UGVROSKLLNISKC-UHFFFAOYSA-N 0.000 description 3
- WCPGJPHDOQFAII-UHFFFAOYSA-N [2-methyl-3-(2-methylcyclohexanecarbonyl)oxypropyl] 2-methylcyclohexane-1-carboxylate Chemical compound CC1CCCCC1C(=O)OCC(C)COC(=O)C2CCCCC2C WCPGJPHDOQFAII-UHFFFAOYSA-N 0.000 description 3
- VVGFUEMSNACWHC-UHFFFAOYSA-N [3-(cyclohexanecarbonyloxy)-2-methylpropyl] cyclohexanecarboxylate Chemical compound CC(COC(=O)C1CCCCC1)COC(=O)C2CCCCC2 VVGFUEMSNACWHC-UHFFFAOYSA-N 0.000 description 3
- NVJBRXJHQQOPNJ-UHFFFAOYSA-N [3-methyl-5-(2-methylcyclohexanecarbonyl)oxypentyl] 2-methylcyclohexane-1-carboxylate Chemical compound CC1CCCCC1C(=O)OCCC(C)CCOC(=O)C2CCCCC2C NVJBRXJHQQOPNJ-UHFFFAOYSA-N 0.000 description 3
- FIUYVLBJHMUPRM-UHFFFAOYSA-N [3-methyl-5-(3-methylcyclohexanecarbonyl)oxypentyl] 3-methylcyclohexane-1-carboxylate Chemical compound CC1CCCC(C1)C(=O)OCCC(C)CCOC(=O)C2CCCC(C2)C FIUYVLBJHMUPRM-UHFFFAOYSA-N 0.000 description 3
- VCVJSWDSNWXXJT-UHFFFAOYSA-N [4-(1-methylpyrazol-3-yl)phenyl]methanol Chemical compound CN1C=CC(C=2C=CC(CO)=CC=2)=N1 VCVJSWDSNWXXJT-UHFFFAOYSA-N 0.000 description 3
- OZAJOTILTSSQBX-UHFFFAOYSA-N [5-(3,4-dimethylcyclohexanecarbonyl)oxy-3-methylpentyl] 3,4-dimethylcyclohexane-1-carboxylate Chemical compound CC1CCC(CC1C)C(=O)OCCC(C)CCOC(=O)C2CCC(C(C2)C)C OZAJOTILTSSQBX-UHFFFAOYSA-N 0.000 description 3
- GQIHXCZESWGAHX-UHFFFAOYSA-N [5-(3,5-dimethylcyclohexanecarbonyl)oxy-3-methylpentyl] 3,5-dimethylcyclohexane-1-carboxylate Chemical compound CC1CC(CC(C1)C(=O)OCCC(C)CCOC(=O)C2CC(CC(C2)C)C)C GQIHXCZESWGAHX-UHFFFAOYSA-N 0.000 description 3
- CCKCOLMDPFVCRC-UHFFFAOYSA-N [5-(cyclohexanecarbonyloxy)-3-methylpentyl] cyclohexanecarboxylate Chemical compound CC(CCOC(=O)C1CCCCC1)CCOC(=O)C2CCCCC2 CCKCOLMDPFVCRC-UHFFFAOYSA-N 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
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- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 3
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- 238000004821 distillation Methods 0.000 description 3
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- 125000004494 ethyl ester group Chemical group 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
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000006078 metal deactivator Substances 0.000 description 3
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- CYVMBANVYOZFIG-ZCFIWIBFSA-N (2r)-2-ethylbutane-1,4-diol Chemical group CC[C@@H](CO)CCO CYVMBANVYOZFIG-ZCFIWIBFSA-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
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- 229940035437 1,3-propanediol Drugs 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
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- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- PQMXFROWMZSBDZ-UHFFFAOYSA-N 2,3,4-triethylpentane-1,5-diol Chemical group CCC(CO)C(CC)C(CC)CO PQMXFROWMZSBDZ-UHFFFAOYSA-N 0.000 description 2
- ZABMGUITRPYVRH-UHFFFAOYSA-N 2,3,4-trimethylpentane-1,5-diol Chemical group OCC(C)C(C)C(C)CO ZABMGUITRPYVRH-UHFFFAOYSA-N 0.000 description 2
- QWLIPWTWNKOORO-UHFFFAOYSA-N 2,3-diethyl-4-methylpentane-1,5-diol Chemical group CCC(CO)C(CC)C(C)CO QWLIPWTWNKOORO-UHFFFAOYSA-N 0.000 description 2
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- HXMRREGZBXNQRL-UHFFFAOYSA-N 2,3-diethylpentane-1,5-diol Chemical group CCC(CO)C(CC)CCO HXMRREGZBXNQRL-UHFFFAOYSA-N 0.000 description 2
- SKQUTIPQJKQFRA-UHFFFAOYSA-N 2,3-dimethylbutane-1,4-diol Chemical group OCC(C)C(C)CO SKQUTIPQJKQFRA-UHFFFAOYSA-N 0.000 description 2
- MJGXPIYXMGYKTR-UHFFFAOYSA-N 2,3-dimethylpentane-1,5-diol Chemical group OCC(C)C(C)CCO MJGXPIYXMGYKTR-UHFFFAOYSA-N 0.000 description 2
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- OXFUXNFMHFCELM-UHFFFAOYSA-N tripropan-2-yl phosphate Chemical compound CC(C)OP(=O)(OC(C)C)OC(C)C OXFUXNFMHFCELM-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
一般式(1):
で表される化合物を含有する動力伝達用潤滑油基油。
一般式(1)に記載のR1~R5が、同一又は異なって、それぞれ水素原子、メチル基、エチル基、イソプロピル基又はtert-ブチル基であり、R1~R5のうちのいずれか2つが互いに結合してメチレン基又はブチレン基を形成してもよい、[項1]に記載の動力伝達用潤滑油基油。
一般式(1)に記載のXが、炭素数3以上の直鎖状アルキレン基を主鎖とし、主鎖上の炭素原子にメチル基及びエチル基からなる群より選択される1種以上の基が結合した、2価の基である、[項1]又は[項2]に記載の動力伝達用潤滑油基油。
一般式(1)に記載のXが、2-メチル-1,3-プロパンジオール、3-メチル-1,5-ペンタンジオール及び2,4-ジエチル-1,5-ペンタンジオールからなる群より選択される1種から2つの水酸基を除いて得られる2価の基である、[項1]~[項3]のいずれかに記載の動力伝達用潤滑油基油。
一般式(1)で表される化合物の含有量が、動力伝達用潤滑油基油中、70質量%以上である、[項1]~[項4]のいずれかに記載の動力伝達用潤滑油基油。
前記動力伝達用潤滑油基油がトラクションドライブ用潤滑油基油である、[項1]~[項5]のいずれかに記載の動力伝達用潤滑油基油。
[項1]~[項6]のいずれかに記載の動力伝達用潤滑油基油を含有する動力伝達用潤滑油。
で表される化合物を含有することを特徴とする。
で表される化合物と表記することもできる。つまり、一般式(1)における「X」を「CH2-Y-CH2」と表記することもできる。
シクロヘキサンカルボン酸:シグマ-アルドリッチ社製
2-メチルシクロヘキサンカルボン酸:シグマ-アルドリッチ社製
3-メチルシクロヘキサンカルボン酸:シグマ-アルドリッチ社製
4-メチルシクロヘキサンカルボン酸:シグマ-アルドリッチ社製
3,4-ジメチルシクロヘキサンカルボン酸:特開昭49-135950号公報を参考に3,4-ジメチル安息香酸(東京化成工業社製)を5質量%パラジウム-カーボン触媒存在下で、水素化反応し、得られた粗物を蒸留精製することにより、3,4-ジメチルシクロヘキサンカルボン酸を得た。
3,5-ジメチルシクロヘキサンカルボン酸:特開昭49-135950号公報を参考に3,5-ジメチル安息香酸(東京化成工業社製)を5質量%パラジウム-カーボン触媒存在下で、水素化反応し、得られた粗物を蒸留精製することにより、3,5-ジメチルシクロヘキサンカルボン酸を得た。
4-tert-ブチルシクロヘキサンカルボン酸:東京化成工業社製
ビシクロ[2.2.1]ヘプタン-2-カルボン酸:富士フイルム和光純薬社製
2-メチル-1,3-プロパンジオール:東京化成工業社製
3-メチル-1,5-ペンタンジオール:東京化成工業社製
2,4-ジエチル-1,5-ペンタンジオール:東京化成工業社製
1,3-ブタンジオール:東京化成工業社製
2,2-ジメチル-1,3-プロパンジオール:東京化成工業社製
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ルブリカンツ社製 製品名「YUBASE 3」(飽和炭化水素の工業用流動パラフィン)
JIS K2501(2003)に準拠して測定した。なお検出限界は0.01KOHmg/gである。
JIS K0070(1992)に準拠して測定した。なお検出限界は0.1KOHmg/gである。
(c)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
滑り率:5%
試料温度:60℃
荷重:200N
<トラクション係数の評価>
[I]:0.100以上
[II]:0.090以上0.100未満
[III]:0.090未満
JIS-K-2269(1987)に準拠して流動点を測定した。
<低温流動性の評価>
[I]:-40℃以下
[II]:-40℃を越え-30℃以下
[III]:-30℃を越える
JIS K2265(クリーブランド開放式)に準拠して測定した。
<引火点の評価>
[I]:220℃以上
[II]:200℃以上220℃未満
[III]:200℃未満
動力伝達用潤滑油基油の評価としては、トラクション係数の評価、低温流動性の評価及び引火点の評価の結果において、[III]が1以上あれば不適と、[II]が2以下(他の評価は[I])であれば良好と、[II]が1以下(他の評価は[I])であれば特に良好と評価される。
撹拌器、温度計、冷却管付き水分分留受器を備えた1リットルの四ツ口フラスコに脂環式モノカルボン酸として3-メチルシクロヘキサンカルボン酸469.2g(3.30mol)、分岐鎖状の脂肪族ジオールとして2-メチル-1,3-プロパンジオール135.2g(1.50mol)、エステル化触媒として酸化スズ0.5g、エントレーナーとしてキシレン30g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。キシレンが還流するように減圧度を調整しながら、理論生成水量(54.0g)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、エステル化反応を行った。反応終了後、残存する3-メチルシクロヘキサンカルボン酸とキシレン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酸価に対して1.5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、2-メチル-1,3-プロパンジオールビス(3-メチル-シクロヘキサンカルボキシレート)409.6g(1.21mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(A)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸をシクロヘキサンカルボン酸423.0g(3.3mol)に、2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールジ(シクロヘキサンカルボキシレート)440.0g(1.30mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(B)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を2-メチルシクロヘキサンカルボン酸469.2g(3.3mol)に、2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールビス(2-メチル-シクロヘキサンカルボキシレート)465.5g(1.27mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(C)として評価した際の各物性を表1に示す。
2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールビス(3-メチルシクロヘキサンカルボキシレート)487.5g(1.33mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(D)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を4-メチルシクロヘキサンカルボン酸469.2g(3.3mol)に、2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールビス(4-メチルシクロヘキサンカルボキシレート)498.5g(1.36mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(E)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸をシクロヘキサンカルボン酸423.0g(3.3mol)に、2-メチル-1,3-プロパンジオールを2,4-ジエチル-1,5-ペンタンジオール240.4g(1.5mol)に変更した以外は実施例1と同様の方法で、2,4-ジエチル-1,5-ペンタンジオールジ(シクロヘキサンカルボキシレート)532.8g(1.40mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(F)として評価した際の各物性を表1に示す。
2-メチル-1,3-プロパンジオールを2,4-ジエチル-1,5-ペンタンジオール240.4g(1.5mol)に変更した以外は実施例1と同様の方法で、2,4-ジエチル-1,5-ペンタンジオールビス(3-メチルシクロヘキサンカルボキシレート)521.0g(1.28mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(G)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を3,4-ジメチルシクロヘキサンカルボン酸515.5g(3.3mol)に、2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールビス(3,4-ジメチルシクロヘキサンカルボキシレート)532.7g(1.35mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(H)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を3,5-ジメチルシクロヘキサンカルボン酸515.5g(3.3mol)に、2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールビス(3,5-ジメチルシクロヘキサンカルボキシレート)538.6g(1.37mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(I)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を4-tert-ブチルシクロヘキサンカルボン酸608.1g(3.3mol)に、2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールビス(4-tert-ブチルシクロヘキサンカルボキシレート)554.4g(1.23mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(J)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸をビシクロ[2.2.1]ヘプタンカルボン酸462.6g(3.3mol)に、2-メチル-1,3-プロパンジオールを3-メチル-1,5-ペンタンジオール177.3g(1.5mol)に変更した以外は実施例1と同様の方法で、3-メチル-1,5-ペンタンジオールビス(ビシクロ[2.2.1]ヘプタンカルボキシレート)467.7g(1.29mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(K)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を2-メチルシクロヘキサンカルボン酸469.3g(3.3mol)に変更した以外は実施例1と同様の方法で、2-メチル-1,3-プロパンジオールビス(2-メチルシクロヘキサンカルボキシレート)462.1g(1.37mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(L)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を2-メチルシクロヘキサンカルボン酸469.6g(3.3mol)に、2-メチル-1,3-プロパンジオールを2,4-ジエチル-1,5-ペンタンジオール240.4g(1.5mol)に変更した以外は実施例1と同様の方法で、2,4-ジエチル-1,5-ペンタンジオールジ(2-メチルシクロヘキサンカルボキシレート)521.0g(1.28mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(M)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸を4-メチルシクロヘキサンカルボン酸469.6g(3.3mol)に、2-メチル-1,3-プロパンジオールを2,4-ジエチル-1,5-ペンタンジオール240.4g(1.5mol)に変更した以外は実施例1と同様の方法で、2,4-ジエチル-1,5-ペンタンジオールジ(4-メチルシクロヘキサンカルボキシレート)514.9g(1.26mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(N)として評価した際の各物性を表1に示す。
3-メチルシクロヘキサンカルボン酸をシクロヘキサンカルボン酸423.0g(3.3mol)に、2-メチル-1,3-プロパンジオールを1,3-ブタンジオール135.2g(1.5mol)に変更した以外は実施例1と同様の方法で、1,3-ブタンジオールジ(シクロヘキサンカルボキシレート)366.3g(1.18mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(a)として評価した際の各物性を表2に示す。
3-メチルシクロヘキサンカルボン酸をシクロヘキサンカルボン酸423.0g(3.3mol)に、2-メチル-1,3-プロパンジオールを2,2-ジメチル-1,3-プロパンジオール156.2g(1.5mol)に変更した以外は実施例1と同様の方法で、2,2-ジメチル-1,3-プロパンジオールジ(シクロヘキサンカルボキシレート)395.8g(1.22mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(b)として評価した際の各物性を表2に示す。
2-メチル-1,3-プロパンジオールを1,3-ブタンジオール135.2g(1.5mol)に変更した以外は実施例1と同様の方法で、1,3-ブタンジオールビス(3-メチルシクロヘキサンカルボキシレート)457.0g(1.35mol)を得た。得られた化合物の酸価は、0.01mgKOH/g以下、水酸基価は、1mgKOH/g以下であった。当該化合物を動力伝達用潤滑油基油(c)として評価した際の各物性を表2に示す。
アジピン酸ジイソデシルを動力伝達用潤滑油基油(d)として評価した際の各物性値を表2に示す。
鉱物油Yを動力伝達用潤滑油基油(e)として評価した際の各物性を表2に示す。
Claims (7)
- 一般式(1)に記載のR1~R5が、同一又は異なって、それぞれ水素原子、メチル基、エチル基、イソプロピル基又はtert-ブチル基であり、R1~R5のうちのいずれか2つが互いに結合してメチレン基又はブチレン基を形成してもよい、請求項1に記載の動力伝達用潤滑油基油。
- 一般式(1)に記載のXが、炭素数3以上の直鎖状アルキレン基を主鎖とし、主鎖上の炭素原子にメチル基及びエチル基からなる群より選択される1種以上の基が結合した、2価の基である、請求項1又は請求項2に記載の動力伝達用潤滑油基油。
- 一般式(1)に記載のXが、2-メチル-1,3-プロパンジオール、3-メチル-1,5-ペンタンジオール及び2,4-ジエチル-1,5-ペンタンジオールからなる群より選択される1種から2つの水酸基を除いて得られる2価の基である、請求項1~3のいずれかに記載の動力伝達用潤滑油基油。
- 一般式(1)で表される化合物の含有量が、動力伝達用潤滑油基油中、70質量%以上である、請求項1~4のいずれかに記載の動力伝達用潤滑油基油。
- 前記動力伝達用潤滑油基油がトラクションドライブ用潤滑油基油である、請求項1~5のいずれかに記載の動力伝達用潤滑油基油。
- 請求項1~6のいずれかに記載の動力伝達用潤滑油基油を含有する動力伝達用潤滑油。
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