JP6040986B2 - 流体軸受用潤滑油基油 - Google Patents
流体軸受用潤滑油基油 Download PDFInfo
- Publication number
- JP6040986B2 JP6040986B2 JP2014519923A JP2014519923A JP6040986B2 JP 6040986 B2 JP6040986 B2 JP 6040986B2 JP 2014519923 A JP2014519923 A JP 2014519923A JP 2014519923 A JP2014519923 A JP 2014519923A JP 6040986 B2 JP6040986 B2 JP 6040986B2
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- Prior art keywords
- acid
- base oil
- methyl
- lubricating base
- test
- 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.)
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- 239000002199 base oil Substances 0.000 title claims description 103
- 230000001050 lubricating effect Effects 0.000 title claims description 58
- 239000012530 fluid Substances 0.000 title claims description 44
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 68
- -1 aliphatic monocarboxylic acid Chemical class 0.000 claims description 62
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 39
- 239000000314 lubricant Substances 0.000 claims description 35
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 34
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 33
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 33
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 32
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 description 58
- 150000002148 esters Chemical class 0.000 description 41
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 39
- 150000005690 diesters Chemical class 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 229940077388 benzenesulfonate Drugs 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000010687 lubricating oil Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KYCZHYRHELYDEB-UHFFFAOYSA-N (5-hexanoyloxy-3-methylpentyl) hexanoate Chemical compound CCCCCC(=O)OCCC(C)CCOC(=O)CCCCC KYCZHYRHELYDEB-UHFFFAOYSA-N 0.000 description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 231100000241 scar Toxicity 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 230000002093 peripheral effect Effects 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
- 229920001296 polysiloxane Polymers 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000011521 glass 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
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000006078 metal deactivator Substances 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 229920013636 polyphenyl ether polymer Chemical class 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 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
- 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
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 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
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical compound CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
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- OJRJDENLRJHEJO-UHFFFAOYSA-N 2,4-diethylpentane-1,5-diol Chemical compound CCC(CO)CC(CC)CO OJRJDENLRJHEJO-UHFFFAOYSA-N 0.000 description 1
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- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- QUADBKCRXGFGAX-UHFFFAOYSA-N octane-1,7-diol Chemical compound CC(O)CCCCCCO QUADBKCRXGFGAX-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 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
- 150000003608 titanium Chemical class 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-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
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 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
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- 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
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- 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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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
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- 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
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- 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
-
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
- C10M2207/2895—Partial esters containing free hydroxy groups used as base material
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- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
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Description
即ち、本発明は、以下のものである。
3−メチル−1,5−ペンタンジオールと、
n−ウンデカン酸(A成分)、並びに
n−ヘキサン酸、n−ヘプタン酸、n−オクタン酸、n−ノナン酸及びn−デカン酸からなる群より選ばれる少なくとも1種の脂肪族モノカルボン酸(B成分)とをエステル化反応して得られるメチルペンタンジオールジエステルであって、
A成分とB成分のモル比が30:70〜70:30の範囲であるメチルペンタンジオールジエステルを含有することを特徴とする流体軸受用潤滑油基油。
B成分が、n−オクタン酸、n−ノナン酸及びn−デカン酸からなる群より選ばれる少なくとも1種である、項1に記載の流体軸受用潤滑油基油。
流体軸受用潤滑油基油中のメチルペンタンジオールジエステルが90重量%以上である、項1又は2に記載の流体軸受用潤滑油基油。
前記流体軸受用潤滑油基油が、動圧流体軸受用潤滑油基油又は焼結含油軸受用潤滑油基油である、項1〜3のいずれかに記載の流体軸受用潤滑油基油。
流体軸受用潤滑油基油が、スピンドルモータ用の流体軸受用潤滑油基油である、項1〜4のいずれかに記載の流体軸受用潤滑油基油。
流体軸受用潤滑油基油が、ハードディスクドライブのスピンドルモータ用の流体軸受用潤滑油基油である、項5に記載の流体軸受用潤滑油基油。
流体軸受用潤滑油基油が、サーバー向けハードディスクドライブのスピンドルモータ用の流体軸受用潤滑油基油である、項6に記載の流体軸受用潤滑油基油。
本発明に係るメチルペンタンジオールジエステルは、n−ウンデカン酸(A成分)、並びに、n−ヘキサン酸、n−ヘプタン酸、n−オクタン酸、n−ノナン酸及びn−デカン酸からなる群より選ばれる少なくとも1種の脂肪族モノカルボン酸(B成分)を、A成分とB成分のモル比が30:70〜70:30の範囲で含有する混合酸と、3−メチル−1,5−ペンタンジオールとのエステル化反応から得られるものである。
本発明のメチルペンタンジオールジエステルは、3−メチル−1,5−ペンタンジオールに脂肪族モノカルボン酸をエステル化反応することにより製造される。当該製造方法には、特に限定がなく、従来公知の製造方法を用いることができる。
JIS−K−2501(1992)に準拠して測定した。なお検出限界は0.01mgKOH/gである。
JIS−K−2283(2000)に準拠して、40℃、100℃における動粘度を測定した。但し、0℃動粘度はJIS−K−2283(2000)に規定される粘度−温度関係式より算出した。
JIS−K−2283(2000)に準拠して算出した。
JIS−K−2269(1987)に準拠して流動点を測定した。
実施例又は比較例の各々の潤滑油基油に対し、2,2’−メチレンビス−2,6−ジ−tert−ブチルフェノール(東京化成工業(株)製)、IRGANOX L57(製品名,BASF製)、各0.5重量%を添加し溶解させて潤滑油組成物を調製した。当該潤滑油組成物を、内径25mm、高さ90mmのガラス管にエステル10gを秤量し、ガラス管を2本取り付けたシリコンゴム栓を付け、片方の管から空気を1.0NL/minで送る。150℃に設定したオイルバスにガラス管を浸漬して、20時間加熱した。加熱試験後の揮発量は下記の式に従い算出した。
揮発量(%)=[(W0−W)/W0]×100
[式中、W0は試験前の重量を示し、Wは試験後の重量を示す。]。
JPI−5S−32−90に準拠して、高速四球型摩耗試験機(神鋼造機製)を用いて、回転数1200rpm、荷重40kg、温度75℃、時間60分の条件で試験し、摩耗痕径を測定した。
(g)部分エステルの増加量測定
潤滑性試験前及び試験後の潤滑油基油をガスクロマトグラフィー(GC)により分析し、部分エステル(ジエステル化合物の片方のエステル基が加水分解した化合物)を測定し、試験後の部分エステルのGC面積%の増加量を算出した。なお、混合エステルについては、各々の部分エステルを合計した。
[GC分析条件]
機器:島津製作所製 GC−2010
カラム:J&W製TC−5 30mx0.25mm
カラム温度:60〜300℃(昇温速度10℃/min)
インジェクション温度/検出器温度:305℃/305℃
検出器:FID
キャリアガス:ヘリウム
ガス流量:1.08ml/min
潤滑性試験前及び試験後の全酸価を測定し、試験後の全酸価の上昇量を算出した。
3−メチル−1,5−ペンタンジオール:クラレ(株)製[MPD]
n−ヘキサン酸:東京化成工業(株)製[Hexanoic Acid]を蒸留精製したものを使用(nC6酸)
n−ヘプタン酸:アルケマ社製[NORMAL HEPTANOIC ACID]を蒸留精製したものを使用(nC7酸)
n−オクタン酸:新日本理化(株)製[カプリル酸]を蒸留精製したものを使用(nC8酸)
n−ノナン酸:OXEA社製[n−Pelargonic Acid]を蒸留精製したものを使用(nC9酸)
n−デカン酸:新日本理化(株)製[カプリン酸]を蒸留精製したものを使用(nC10酸)
n−ウンデカン酸:東京化成工業(株)製[Undecanoic Acid]を蒸留精製したものを使用(nC11酸)
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n−ヘキサン酸106.5g(0.92モル)、n−ウンデカン酸398.4g(2.14モル)、3−メチル−1,5−ペンタンジオール177.0g(1.50モル)、キシレン(原料の総量に対し5重量%)及び触媒として酸化スズ(原料の総量に対し0.1重量%)を仕込み、窒素置換した後、徐々に230℃まで昇温した。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、還流が起こ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20以下となるまで反応を行った。反応終了後、キシレン及び残存する原料脂肪族モノカルボン酸を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1.2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した。更に、得られたエステル化粗物を活性炭で処理した後、濾過により活性炭を除去して、全酸価が0.01mgKOH/g以下、部分エステル量0.12GC面積%の3−メチル−1,5−ペンタンジオールとn−ヘキサン酸、n−ウンデカン酸(モル比:nC6酸/nC11酸=30/70)とのジエステル521.8gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘキサン酸に代えてn−オクタン酸220.3g(1.53モル)を用い、n−ウンデカン酸の使用量を284.6g(1.53モル)に変えた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオールとn−オクタン酸、n−ウンデカン酸(モル比:nC8酸/nC11酸=50/50)とのジエステル574.7gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘキサン酸に代えてn−ノナン酸241.7g(1.53モル)を用い、n−ウンデカン酸の使用量を284.6g(1.53モル)に変えた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオールとn−ノナン酸、n−ウンデカン酸(モル比:nC9酸/nC11酸=50/50)とのジエステル594.3gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘキサン酸に代えてn−デカン酸157.9g(0.92モル)を用いた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオールとn−デカン酸、n−ウンデカン酸(モル比:nC10酸/nC11酸=30/70)とのジエステル620.2gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘキサン酸に代えてn−デカン酸263.2g(1.53モル)を用い、n−ウンデカン酸の使用量を284.6g(1.53モル)に変えた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオールとn−デカン酸、n−ウンデカン酸(モル比:nC10酸/nC11酸=50/50)とのジエステル613.8gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘキサン酸に代えてn−デカン酸368.4g(2.14モル)を用い、n−ウンデカン酸の使用量を170.7g(0.92モル)に変えた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオールとn−デカン酸、n−ウンデカン酸(モル比:nC10酸/nC11酸=70/30)とのジエステル606.4gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘキサン酸に代えてn−ノナン酸145.0g(0.92モル)及びn−デカン酸157.9g(0.92モル)を用い、n−ウンデカン酸の使用量を227.7g(1.22モル)に変えた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオールとn−ノナン酸、n−デカン酸、n−ウンデカン酸(モル比:nC9酸/nC10酸/nC11酸=30/30/40)とのジエステル594.3gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘキサン酸355.0g(3.06モル)と3−メチル−1,5−ペンタンジオール177.0g(1.50モル)とを用いた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオール−ジ(n−ヘキサノエート)438.0gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ヘプタン酸397.8g(3.06モル)と3−メチル−1,5−ペンタンジオール177.0g(1.50モル)とを用いた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオール−ジ(n−ヘキサノエート)477.1gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−オクタン酸440.6g(3.06モル)と3−メチル−1,5−ペンタンジオール177.0g(1.50モル)とを用いた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオール−ジ(n−ヘキサノエート)516.2gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ノナン酸483.5g(3.06モル)と3−メチル−1,5−ペンタンジオール177.0g(1.50モル)とを用いた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオール−ジ(n−ヘキサノエート)555.2gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−デカン酸526.3g(3.06モル)と3−メチル−1,5−ペンタンジオール177.0g(1.50モル)とを用いた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオール−ジ(n−ヘキサノエート)594.3gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
n−ウンデカン酸569.2g(3.06モル)と3−メチル−1,5−ペンタンジオール177.0g(1.50モル)とを用いた以外は、実施例1と同様の方法により、本発明の3−メチル−1,5−ペンタンジオール−ジ(n−ヘキサノエート)633.3gを得た。合成したエステルの全酸価、動粘度、粘度指数、低温流動性試験、耐熱性試験、潤滑性試験及び潤滑性試験後の潤滑油基油の分析を行い、それらの試験結果を表1に示した。
Claims (5)
- 3−メチル−1,5−ペンタンジオールと、
n−ウンデカン酸(A成分)、並びに
n−ヘキサン酸、n−ヘプタン酸、n−オクタン酸、n−ノナン酸及びn−デカン酸からなる群より選ばれる少なくとも1種の脂肪族モノカルボン酸(B成分)とをエステル化反応して得られるメチルペンタンジオールジエステルであって、
A成分とB成分のモル比が30:70〜70:30の範囲であるメチルペンタンジオールジエステルを含有することを特徴とする流体軸受用潤滑油基油。 - B成分が、n−オクタン酸、n−ノナン酸及びn−デカン酸からなる群より選ばれる少なくとも1種である、請求項1に記載の流体軸受用潤滑油基油。
- 流体軸受用潤滑油基油中のメチルペンタンジオールジエステルが90重量%以上である、請求項1又は2に記載の流体軸受用潤滑油基油。
- 流体軸受用潤滑油基油が、動圧流体軸受用潤滑油基油又は焼結含油軸受用潤滑油基油である、請求項1〜3のいずれかに記載の流体軸受用潤滑油基油。
- 流体軸受用潤滑油基油が、スピンドルモータ用の流体軸受用潤滑油基油である、請求項1〜4のいずれかに記載の流体軸受用潤滑油基油。
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