JP6316406B2 - 向上したエネルギー効率を有する潤滑油組成物 - Google Patents
向上したエネルギー効率を有する潤滑油組成物 Download PDFInfo
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- JP6316406B2 JP6316406B2 JP2016513290A JP2016513290A JP6316406B2 JP 6316406 B2 JP6316406 B2 JP 6316406B2 JP 2016513290 A JP2016513290 A JP 2016513290A JP 2016513290 A JP2016513290 A JP 2016513290A JP 6316406 B2 JP6316406 B2 JP 6316406B2
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- Prior art keywords
- acid
- mass
- monoalcohol
- group
- lubricating oil
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 74
- 239000010687 lubricating oil Substances 0.000 title claims description 28
- -1 alkyl naphthalene Chemical compound 0.000 claims description 49
- 239000003921 oil Substances 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 24
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 23
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 15
- 229920013639 polyalphaolefin Polymers 0.000 claims description 15
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 13
- 239000001361 adipic acid Substances 0.000 claims description 12
- 235000011037 adipic acid Nutrition 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 12
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 230000001050 lubricating effect Effects 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229920002545 silicone oil Polymers 0.000 claims description 7
- 239000002199 base oil Substances 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 5
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 5
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 5
- HDLHSQWNJQGDLM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,5-dicarboxylic acid Chemical compound C1C2C(C(=O)O)CC1C(C(O)=O)C2 HDLHSQWNJQGDLM-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 235000011087 fumaric acid Nutrition 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 3
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 description 55
- 150000002148 esters Chemical class 0.000 description 31
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 27
- 239000000314 lubricant Substances 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 18
- 229960002317 succinimide Drugs 0.000 description 17
- 150000003904 phospholipids Chemical class 0.000 description 16
- 239000012530 fluid Substances 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 230000005540 biological transmission Effects 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000010705 motor oil Substances 0.000 description 9
- 229920002367 Polyisobutene Polymers 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 235000010338 boric acid Nutrition 0.000 description 7
- 229960002645 boric acid Drugs 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000004034 viscosity adjusting agent Substances 0.000 description 7
- QEVWDMOIPOLQBL-UHFFFAOYSA-N 5-methyl-2-propylhexan-1-ol Chemical compound CCCC(CO)CCC(C)C QEVWDMOIPOLQBL-UHFFFAOYSA-N 0.000 description 6
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 5
- AOWJVNTZMBKLQO-UHFFFAOYSA-N 2-propan-2-ylheptan-1-ol Chemical compound CCCCCC(CO)C(C)C AOWJVNTZMBKLQO-UHFFFAOYSA-N 0.000 description 5
- VZXWJVFQXZUFQS-UHFFFAOYSA-N 4-methyl-2-propylhexan-1-ol Chemical compound CCCC(CO)CC(C)CC VZXWJVFQXZUFQS-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 150000001639 boron compounds Chemical class 0.000 description 5
- 239000010725 compressor oil Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Chemical class 0.000 description 5
- 239000010723 turbine oil Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000010721 machine oil Substances 0.000 description 4
- 238000005555 metalworking Methods 0.000 description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 239000010689 synthetic lubricating oil Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 230000000996 additive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- YKGYQYOQRGPFTO-UHFFFAOYSA-N bis(8-methylnonyl) hexanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC(C)C YKGYQYOQRGPFTO-UHFFFAOYSA-N 0.000 description 3
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
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- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 2
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- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
- IRKHIJIMXUBALO-UHFFFAOYSA-N triheptyl borate Chemical compound CCCCCCCOB(OCCCCCCC)OCCCCCCC IRKHIJIMXUBALO-UHFFFAOYSA-N 0.000 description 1
- KDQYHGMMZKMQAA-UHFFFAOYSA-N trihexyl borate Chemical compound CCCCCCOB(OCCCCCC)OCCCCCC KDQYHGMMZKMQAA-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AZLXEMARTGQBEN-UHFFFAOYSA-N trinonyl borate Chemical compound CCCCCCCCCOB(OCCCCCCCCC)OCCCCCCCCC AZLXEMARTGQBEN-UHFFFAOYSA-N 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- ZAGXLQIHXTXRFW-UHFFFAOYSA-N tris(2-ethyl-4-methylhexyl)-tris(2-ethyl-4-methylhexyl)silyloxysilane Chemical compound CCC(C)CC(CC)C[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)O[Si](CC(CC)CC(C)CC)(CC(CC)CC(C)CC)CC(CC)CC(C)CC ZAGXLQIHXTXRFW-UHFFFAOYSA-N 0.000 description 1
- WAXLMVCEFHKADZ-UHFFFAOYSA-N tris-decyl borate Chemical compound CCCCCCCCCCOB(OCCCCCCCCCC)OCCCCCCCCCC WAXLMVCEFHKADZ-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
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Description
a)任意に無水物の形の、少なくとも1つのジカルボン酸および
b1)10個の炭素原子を有し、一般式I
を含む混合物を反応させることによって得ることができるカルボン酸エステルと配合することを含む、機械装置の潤滑において潤滑油組成物の摩擦係数を減少させる方法を提供することであった。
R4は、ペンチル、イソペンチル、2−メチルブチル、3−メチルブチルおよび2,2−ジメチルプロピルからなる群から選択されており、
R5は、Hまたはメチルであり、および
R6は、エチル、プロピルおよびイソプロピルからなる群から選択されている〕の構造を有するモノアルコールb2)を含み、
それによって、モノアルコールb1)とモノアルコールb2)とは、異なる構造を有する。
R7は、ペンチル、イソペンチル、2−メチル−ブチル、3−メチル−ブチルおよび2,2−ジメチル−プロピルからなる群から選択されており、
R8は、Hまたはメチルであり、
R9は、エチル、プロピルおよびイソプロピルからなる群から選択されている〕の構造を有するモノアルコールb3)を含む。
a)グループIのベースストックは、飽和物質を90%を下回りおよび/または硫黄を0.03%を上回り含有しかつ以下の表中に規定された試験方法を使用して80以上および120未満の粘度指数を有する。
b)グループIIのベースストックは、飽和物質を90%以上および/または硫黄を0.03%以下含有しかつ以下の表中に規定された試験方法を使用して80以上および120未満の粘度指数を有する。
c)グループIIIのベースストックは、飽和物質を90%以上および/または硫黄を0.03%以下含有しかつ以下の表中に規定された試験方法を使用して120以上の粘度指数を有する。
エステル化合物の製造
プロピルヘプタノールは、BASF SE社、Ludwigshafen在、から商業的に入手可能である[2−プロピル−ヘプタノール93.0質量%;2−プロピル−4−メチル−ヘキサノール2.9質量%;2−プロピル−5−メチルヘキサノール3.9質量%および2−イソプロピルヘプタノール0.2質量%]。
“プロピルヘプタノール”(2.4モル)およびアジピン酸(1.0モル)として、BASF SE社から入手可能である、10個の炭素原子を有するアルコールの構造異性体の混合物を、イソプロピル−ブチル−チタネート(0.001モル)の存在下にオートクレーブ中で不活性ガス(N2)の下、230℃の反応温度で反応させる。反応中に形成される水を、不活性ガス流(N2流)によって反応混合物から除去する。180分後に、過剰のアルコールを、50ミリバールの圧力での蒸留によって前記混合物から除去する。次に、こうして得られたアジピン酸エステルを80℃で0.5%NaOHで中和する。有機相と水相とが分離された後で、続いて有機相を2回水で洗浄する。さらなる工程において、有機相を、粗製アジピン酸エステルを蒸気で180℃および50ミリバールで処理することによって精製する。次に、エステルを150℃および50ミリバールでN2流に供することによって、このエステルを乾燥させる。最終的に、前記エステルを活性炭と混合し、および減圧下に80℃でレオロジー剤としてスープラセオライト(supra−theorit)を使用してろ過する。アジピン酸エステルは、そのつどASTM D 4052でDIN 51757に従って測定した、20℃での0.916g/cm3の密度を示す。
流体をMTM(Mini−Traction Machine)トラクション計測器中で、いわゆる、トラクション試験モードを使用して試験した。前記モードで、摩擦係数を滑り率(SRR)の範囲に亘って一定の平均速度で測定してトラクション曲線をもたらす。SRR=滑り速度/平均連行速度=2(U1 − U2)/(U1 + U2)、ここで、それぞれ、U1は、鋼球速度であり、およびU2は、ディスク速度である。
MTM試験の結果は、図1および2中に示されている。そのつど、上側の曲線は、配合物Aの評価から得られたものであり、および下側の曲線は、配合物Bの評価から得られたものである。そのつど、本発明によるエステルを含有する配合物は、著しく低い摩擦係数を示す。
Claims (13)
- 機械装置の潤滑において潤滑油組成物の摩擦係数を減少させる方法であって、
前記潤滑油組成物を、
a)任意に無水物の形の、少なくとも1つのジカルボン酸ならびに
b1)10個の炭素原子を有し、一般式I
の構造を有するモノアルコールおよび
b2)10個の炭素原子を有し、一般式II
R 4 は、ペンチル、イソペンチル、2−メチルブチル、3−メチルブチルおよび2,2−ジメチルプロピルからなる群から選択されており、
R 5 は、Hまたはメチルであり、および
R 6 は、エチル、プロピルおよびイソプロピルからなる群から選択されている〕
の構造を有する、少なくとも1つのモノアルコール
を含む混合物を反応させることによって得ることができるカルボン酸エステルと配合することを含み、
前記モノアルコールb1)と前記モノアルコールb2)とは異なる構造を有し、
前記ジカルボン酸は、フタル酸、コハク酸、アルキルコハク酸、アルケニルコハク酸、マレイン酸、アゼライン酸、スベリン酸、セバシン酸、フマル酸、アジピン酸、リノール酸二量体、マロン酸、アルキルマロン酸、アルケニルマロン酸、グルタル酸、ジグリコール酸、1,4−シクロヘキサンジカルボン酸、2,6−デカヒドロナフタレンジカルボン酸、1,3−シクロヘキサンジカルボン酸および2,5−ノルボルナンジカルボン酸からなる群から選択されている、前記方法。 - 摩擦係数を、70℃および1GPaでの小型トラクション計測器(MTM)による測定を用いて25%の滑り率(SRR)で測定する、請求項1記載の方法。
- 前記ジカルボン酸は、グルタル酸、ジグリコール酸、コハク酸、アゼライン酸、セバシン酸、1,4−シクロヘキサンジカルボン酸、アジピン酸、2,6−デカヒドロナフタレンジカルボン酸、1,3−シクロヘキサンジカルボン酸および2,5−ノルボルナンジカルボン酸からなる群から選択されている、請求項1または2記載の方法。
- 前記ジカルボン酸は、アジピン酸である、請求項1から3までのいずれか1項に記載の方法。
- モノアルコールb1)対モノアルコールb2)の質量比は、5:1〜95:1の範囲内にある、請求項1から4までのいずれか1項に記載の方法。
- 前記モノアルコールb1)は、酸a)に対して、2.05:1〜3.0:1の範囲内のモル比で存在する、請求項1から5までのいずれか1項に記載の方法。
- 前記潤滑油組成物は、潤滑油組成物の全体量に対して、少なくとも1つのカルボン酸エステルを、1質量%以上〜10質量%以下または1質量%以上〜40質量%以下または20質量%以上〜100質量%以下含む、請求項1から6までのいずれか1項に記載の方法。
- 前記潤滑油組成物は、さらに、鉱油(グループI、IIまたはIII油)、ポリα−オレフィン、重合されたオレフィン、共重合されたオレフィン、アルキルナフタレン、アルキレンオキサイドポリマー、シリコーン油およびリン酸エステルからなる群から選択された基油を含む、請求項1から7までのいずれか1項に記載の方法。
- 前記潤滑油組成物は、潤滑油組成物の全体量に対して、基油を1質量%以上〜49質量%以下または50質量%以上〜99質量%以下含む、請求項8記載の方法。
- 前記機械装置は、軸受、アクチュエータ、歯車、ピストン、クランク軸、継手および誘導装置からなる群から選択されている、請求項1から9までのいずれか1項に記載の方法。
- 前記機械装置は、10℃以上ないし120℃以下の範囲内の温度で運転される、請求項1から10までのいずれか1項に記載の方法。
- 機械装置の潤滑において潤滑油組成物の摩擦係数を減少させるための、
a)任意に無水物の形の、少なくとも1つのジカルボン酸ならびに
b1)10個の炭素原子を有し、一般式I
の構造を有するモノアルコールおよび
b2)10個の炭素原子を有し、一般式II
R 4 は、ペンチル、イソペンチル、2−メチルブチル、3−メチルブチルおよび2,2−ジメチルプロピルからなる群から選択されており、
R 5 は、Hまたはメチルであり、および
R 6 は、エチル、プロピルおよびイソプロピルからなる群から選択されている〕
の構造を有する、少なくとも1つのモノアルコール
を含む混合物を反応させることによって得ることができるカルボン酸エステルの使用であって、
前記モノアルコールb1)と前記モノアルコールb2)とは異なる構造を有し、
前記ジカルボン酸は、フタル酸、コハク酸、アルキルコハク酸、アルケニルコハク酸、マレイン酸、アゼライン酸、スベリン酸、セバシン酸、フマル酸、アジピン酸、リノール酸二量体、マロン酸、アルキルマロン酸、アルケニルマロン酸、グルタル酸、ジグリコール酸、1,4−シクロヘキサンジカルボン酸、2,6−デカヒドロナフタレンジカルボン酸、1,3−シクロヘキサンジカルボン酸および2,5−ノルボルナンジカルボン酸からなる群から選択されている、前記使用。 - 摩擦係数を、70℃および1GPaでの小型トラクション計測器(MTM)による測定を用いて25%の滑り率(SRR)で測定する、請求項12記載の使用。
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PCT/EP2014/059338 WO2014184068A1 (en) | 2013-05-14 | 2014-05-07 | Lubricating oil composition with enhanced energy efficiency |
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