JP5680648B2 - 潤滑組成物 - Google Patents
潤滑組成物 Download PDFInfo
- Publication number
- JP5680648B2 JP5680648B2 JP2012528340A JP2012528340A JP5680648B2 JP 5680648 B2 JP5680648 B2 JP 5680648B2 JP 2012528340 A JP2012528340 A JP 2012528340A JP 2012528340 A JP2012528340 A JP 2012528340A JP 5680648 B2 JP5680648 B2 JP 5680648B2
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- JP
- Japan
- Prior art keywords
- cation
- lubricating composition
- ionic liquid
- alkyl groups
- bis
- 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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- 239000000203 mixture Substances 0.000 title claims description 77
- 230000001050 lubricating effect Effects 0.000 title claims description 54
- -1 pyrazolium cation Chemical class 0.000 claims description 87
- 239000002608 ionic liquid Substances 0.000 claims description 40
- 239000000654 additive Substances 0.000 claims description 29
- 239000002199 base oil Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 150000001768 cations Chemical class 0.000 claims description 17
- 238000004939 coking Methods 0.000 claims description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
- OEDJAKMCWJUAHH-UHFFFAOYSA-M methyl(trioctyl)azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC OEDJAKMCWJUAHH-UHFFFAOYSA-M 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 11
- 230000000996 additive effect Effects 0.000 claims description 10
- 239000010802 sludge Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- HYNYWFRJHNNLJA-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;trihexyl(tetradecyl)phosphanium Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC HYNYWFRJHNNLJA-UHFFFAOYSA-N 0.000 claims description 5
- HQWOEDCLDNFWEV-UHFFFAOYSA-M diethyl phosphate;1-ethyl-3-methylimidazol-3-ium Chemical compound CC[N+]=1C=CN(C)C=1.CCOP([O-])(=O)OCC HQWOEDCLDNFWEV-UHFFFAOYSA-M 0.000 claims description 5
- BXSDLSWVIAITRQ-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCN1C=C[N+](C)=C1 BXSDLSWVIAITRQ-UHFFFAOYSA-M 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- CYNWZZPYFZFRNL-UHFFFAOYSA-O FC(=C(F)F)F.C(CCCCC)C1=C(N=C([NH+]1C)CCCCCC)CCCCCC Chemical compound FC(=C(F)F)F.C(CCCCC)C1=C(N=C([NH+]1C)CCCCCC)CCCCCC CYNWZZPYFZFRNL-UHFFFAOYSA-O 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- PNUQOORUABFOJG-UHFFFAOYSA-N P(=O)(F)(F)F.FC(=C(F)F)F.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC Chemical compound P(=O)(F)(F)F.FC(=C(F)F)F.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC.C(CCC)[P+](CCCC)(CCCC)CCCC PNUQOORUABFOJG-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005463 sulfonylimide group Chemical group 0.000 claims description 2
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 claims 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- QXWSCRJIAUGEDH-UHFFFAOYSA-N diethyl hydrogen phosphate;1-methylimidazole Chemical compound C[NH+]1C=CN=C1.CCOP([O-])(=O)OCC QXWSCRJIAUGEDH-UHFFFAOYSA-N 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 description 23
- 239000010705 motor oil Substances 0.000 description 18
- 239000003599 detergent Substances 0.000 description 15
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 14
- 229940059574 pentaerithrityl Drugs 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 9
- 238000005260 corrosion Methods 0.000 description 8
- 230000007797 corrosion Effects 0.000 description 8
- 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 7
- 238000009825 accumulation Methods 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 239000007866 anti-wear additive Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 239000000314 lubricant Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000002518 antifoaming agent Substances 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 3
- 150000003873 salicylate salts Chemical class 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N 2-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical group CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000004707 phenolate Chemical class 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AFQJYYPIAZDTHT-UHFFFAOYSA-N (3,5-dimethylphenyl) dihydrogen phosphate Chemical compound CC1=CC(C)=CC(OP(O)(O)=O)=C1 AFQJYYPIAZDTHT-UHFFFAOYSA-N 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- PXELHGDYRQLRQO-UHFFFAOYSA-N 1-butyl-1-methylpyrrolidin-1-ium Chemical compound CCCC[N+]1(C)CCCC1 PXELHGDYRQLRQO-UHFFFAOYSA-N 0.000 description 1
- MEMNKNZDROKJHP-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCN1C=C[N+](C)=C1 MEMNKNZDROKJHP-UHFFFAOYSA-M 0.000 description 1
- ZNZCBZJTANSNGL-UHFFFAOYSA-N 1-n,2-n-diphenylbenzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2C=CC=CC=2)C=1NC1=CC=CC=C1 ZNZCBZJTANSNGL-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- SZATXRHXOOLEFV-UHFFFAOYSA-N 2,6-ditert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SZATXRHXOOLEFV-UHFFFAOYSA-N 0.000 description 1
- RRKBRXPIJHVKIC-UHFFFAOYSA-N 2-(2-ethylhexyl)phenol Chemical compound CCCCC(CC)CC1=CC=CC=C1O RRKBRXPIJHVKIC-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- UNPVPOMSLNIIDV-UHFFFAOYSA-N 2-dodecan-3-ylphenol Chemical compound CCCCCCCCCC(CC)C1=CC=CC=C1O UNPVPOMSLNIIDV-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical group CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- DHTAIMJOUCYGOL-UHFFFAOYSA-N 2-ethyl-n-(2-ethylhexyl)-n-[(4-methylbenzotriazol-1-yl)methyl]hexan-1-amine Chemical compound C1=CC=C2N(CN(CC(CC)CCCC)CC(CC)CCCC)N=NC2=C1C DHTAIMJOUCYGOL-UHFFFAOYSA-N 0.000 description 1
- IHQZONJYGAQKGK-UHFFFAOYSA-N 2-tert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C(C(C)(C)C)=C1 IHQZONJYGAQKGK-UHFFFAOYSA-N 0.000 description 1
- PMRDUCIMVOFYBX-UHFFFAOYSA-N 2-tert-butyl-4-heptyl-6-methylphenol Chemical compound CCCCCCCC1=CC(C)=C(O)C(C(C)(C)C)=C1 PMRDUCIMVOFYBX-UHFFFAOYSA-N 0.000 description 1
- XCIGNJPXXAPZDP-UHFFFAOYSA-N 2-tert-butyl-4-heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C(C(C)(C)C)=C1 XCIGNJPXXAPZDP-UHFFFAOYSA-N 0.000 description 1
- ZXENURKTAAQNOU-UHFFFAOYSA-N 2-tert-butyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C(C)(C)C)=C1 ZXENURKTAAQNOU-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical compound C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 description 1
- TUSUWHFYKZZRIG-JQWMYKLHSA-N C([C@@H](NC(=O)[C@@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@H](CC(C)C)C(N)=O)C1=CC=CC=C1 Chemical compound C([C@@H](NC(=O)[C@@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@H](CC(C)C)C(N)=O)C1=CC=CC=C1 TUSUWHFYKZZRIG-JQWMYKLHSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 229910000316 alkaline earth metal phosphate Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000000573 anti-seizure effect Effects 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
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Classifications
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
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Description
(i)重量で50%から99%までのベースオイル;
(ii)重量で0.01%から5%までのイオン性液体;および
(iii)重量で0.01%から10%までの添加剤;
ここで、この潤滑組成物は高くても−54℃の流動点と、少なくとも246℃の引火点、および100℃において4.9〜5.4mm2/sの範囲の動粘度を有する。
本発明の潤滑組成物は、(ASTM D92によって測定される)少なくとも246℃の引火点、好ましくは少なくとも250℃の引火点を有する。
ベースオイルは、潤滑組成物の重量で、50%〜99%の範囲のレベルで、好ましくは70%〜99%の範囲で、より好ましくは80%〜97%の範囲で存在する。
好ましくは、ベースオイルにおいては、40℃における動粘度が20〜30mm2/sの範囲、より好ましくは22〜25mm2/sの範囲であり、100℃における動粘度が4〜6mm2/sの範囲、より好ましくは4.85〜5.15mm2/sの範囲であり、−40℃における動粘度が7000〜13000mm2/sの範囲、より好ましくは8000〜10000mm2/sの範囲であり、流動点が−50℃〜−65℃の範囲、より好ましくは−55℃〜−60℃の範囲であり、そして引火点が230〜260℃の範囲、より好ましくは250〜260℃の範囲である。
適切なものとして、ポリオールエステルのベースオイルは、約80〜95重量%のモノペンタエリトリトールと5〜20重量%のジペンタエリトリトールの混合物であってもよい。この混合物は典型的には「工業用の(technical)」ペンタエリトリトールとして知られていて、幾分かのトリペンタエリトリトールとテトラペンタエリトリトールを含んでいてもよく、これらは工業用のペンタエリトリトールを製造する間の副生物として典型的に形成される。
イオン性液体は、潤滑組成物の重量で、0.01%〜5%の範囲のレベルで、好ましくは0.01%〜2%の範囲で、より好ましくは0.05%〜0.5%の範囲で、特に0.1%〜0.3%の範囲で存在する。
イオン性液体はC+A−の式で示すことができて、ここでC+は適切なカチオンであり、A−は適切なアニオンである。
メチルトリオクチルアンモニウム−トリフルオロアセテート(MOAac)、トリヘキシル(テトラデシル)ホスホニウム−ビス(トリフルオロメチルスルホニル)イミド(HDPimid)、ヘキシルメチルイミダゾリウムテトラフルオロボレート(HMI BF4)、ヘキシルメチルイミダゾリウムヘキサフルオロホスフェート(HMI PF6)、1−エチル−3−メチルイミダゾリウムジエチルホスフェート(EMIM DEP)、1−エチル−3−メチルイミダゾリウムメチルスルフェート(EMIM DSU)、およびこれらの混合物。
潤滑組成物に消泡剤を、有利なものとして添加してもよい。これらの添加剤は、安定した泡の形成を抑制する。シリコーンと有機ポリマーが典型的な消泡剤であり、例えばポリシロキサンである。消泡剤は、例えばDow Corning社からDCF 200/12500、DCF 200/500、DCF 200/30000、DCF 200/1000として市販されていて、解乳化剤のような他の添加剤とともに通常の副次的な量で用いてもよく、これらの添加剤を合わせた量は通常1重量%未満である。
実施例1〜18および比較例A
以下の表1〜3に示されるベースオイルと添加剤を配合することによって実施例1〜18および比較例Aのタービンエンジンオイルを調製した。
表1〜3の配合物において用いたベースオイルは5cSt(5センチストークス)のペンタエリトリトールエステルであり、この配合物にはさらに、トリクレジルホスフェート耐摩耗添加剤、トルトリアゾール腐食防止剤、ジカルボン酸腐食防止剤、ジフェニルアミン(DPA)のタイプの酸化防止剤成分としてのジオクチルジフェニルアミン(DODPA)およびジアリールジフェニルアミン、フェニル−アルファ−ナフタレン(PANA)のタイプの酸化防止剤成分としてのp−tert−オクチルフェニル−アルファ−ナフチルアミン、およびポリシロキサン消泡剤を含んでいた。ペンタエリトリトールエステルは、100℃において5mm2/sの粘度と−40℃において13000mm2/sの最大粘度を有していた。また、ペンタエリトリトールエステルは−54℃の最高流動点と246℃の最低引火点を有していた。
本発明のタービンエンジンオイルの様々な利益を証明するために、実施例1、4および16(それぞれ0.2%のMOAac、0.2%のHDPimidおよび0.2%のEMIM MSUを含む)および比較例Aを、試験を行なう間の粘度の増大量、TANの増大量および蒸発減量を測定するためのFED−STD−791−5308.7に示された試験法に供した。試験を218℃において72時間にわたって行った。結果を下の表5に示す。
本発明に係る潤滑組成物のコーキング挙動を測定するために、実施例1および4(それぞれ0.2重量%のMOAacおよび0.2重量%のHDPimidを含む)および比較例Aを、HLPS標準試験法であるSAE ARP 5996に供した。20時間後にステンレス鋼の管の上に形成されたコークスの量を秤量し、そして管の目視による外観を記録した。結果を表6に示す。
本発明に係る潤滑組成物の耐力(負荷耐力)および耐摩耗特性を測定するために、実施例7〜12および比較例Aを、四ボール試験(IP 239)に供し、また各々の試料の最大融着荷重を測定した(各々の荷重段階は10秒間)。結果を下の表7に示す。
表4に示される結果は、タービンエンジンオイルへの低レベルのイオン性液体の導入はタービンエンジンオイルの物理的性質に有害な影響を及ぼさないことを証明している(軍事用および民間用の仕様、すなわちMIL−PRF−23699およびSAE−AS−5780の各仕様によって要求される物理的性質)。
Claims (10)
- 潤滑組成物であって:
(i)重量で50%から99%までのベースオイル;
(ii)重量で0.01%から5%までのイオン性液体;および
(iii)重量で0.01%から10%までの添加剤;
を含み、−54℃未満の流動点と、246℃よりも高い引火点、および100℃において4.9〜5.4mm2/sの範囲の動粘度を有し、
イオン性液体は一般式がC + A − の塩であり、カチオンC + は、第四級アンモニウムカチオン、ホスホニウムカチオン、イミダゾリウムカチオン、ピリジニウムカチオン、ピラゾリウムカチオン、オキサゾリウムカチオン、ピロリジニウムカチオン、ピペリジニウムカチオン、トリアルキルスルホニウムカチオン、チアゾリウムカチオン、グアニジニウムカチオン、モルホリニウムカチオン、スルホニウムカチオンおよびトリアゾリウムカチオンから選択され、アニオンA − は、[PF 6 ] − 、[BF 4 ] − 、[CF 3 CO 2 ] − 、[CF 3 SO 3 ] − 、およびその高級同族体、[C 4 F 9 SO 3 ] − または[C 8 F 17 SO 3 ] − および高級ペルフルオロアルキルスルホネート、[(CF 3 SO 2 ) 2 N] − 、[(CF 3 SO 2 )(CF 3 COO)N] − 、Cl − 、Br − 、I − 、[C(CN) 3 ] − 、SCN − 、[B(C 2 O 4 ) 2 ] − 、[N(SO 2 CF 3 ) 2 ] − 、[R 4 SO 3 ] − 、[R 4 OSO 3 ] − 、[R 4 COO] − 、[NO 3 ] − 、[N(CN) 2 ] − 、[HSO 4 ] − 、PF 6−x R 6 x または[R 4 R 5 PO 4 ] − から選択され、ここでR 4 とR 5 は、水素、線状または枝分れした飽和または不飽和の脂肪族または脂環式アルキル基であって1〜20個の炭素原子を有するもの、ヘテロアリール基およびヘテロアリール−C 1 −C 6 −アルキル基であってヘテロアリール残基中の3〜8個の炭素原子とN、OおよびSから選択される少なくとも1個のヘテロ原子を有するもの(これらはC 1 −C 6 −アルキル基および/またはハロゲン原子から選択される少なくとも1個の群で置換することができる)、アリール−アリール−C 1 −C 6 −アルキル基であってアリール残基中の5〜12個の炭素原子を有するもの(これらは少なくとも1個のC 1 −C 6 −アルキル基で置換することができる)から独立して選択され、R 6 はペルフルオロエチル基または高級ペルフルオロアルキル基とすることができて、そしてxは1〜4の整数である、潤滑組成物。 - 重量で0.01%から1%までのイオン性液体を含む、請求項1に記載の潤滑組成物。
- 重量で0.05%から0.5%までのイオン性液体を含む、請求項1または2に記載の潤滑組成物。
- イオン性液体は、ブチルメチルピロリジニウム−ビス(トリフルオロメチルスルホニル)イミド、メチルプロピルピロリジニウム−ビス(トリフルオロメチルスルホニル)イミド、トリス−ヘキシルメチルイミダゾリウム(ペルフルオロエチレン)−トリフルオロホスフェート、ヘキシルメチルイミダゾリウム−ビス(トリフルオロメチルスルホニル)イミド、ヘキシルメチルピロリジニウム−ビス(トリフルオロメチルスルホニル)イミド、トリス−テトラブチルホスホニウム(ペルフルオロエチレン)トリフルオロホスフェート、オクチルメチルイミダゾリウム−ヘキサフルオロホスフェート、ヘキシルピリジニウム−ビス(トリフルオロメチル)スルホニルイミド、メチルトリオクチルアンモニウム−トリフルオロアセテート、ブチルメチルピロリジニウムトリス(ペンタフルオロエチル)トリフルオロホスフェート、トリヘキシル(テトラデシル)ホスホニウム−ビス(トリフルオロメチルスルホニル)イミド、ヘキシルメチルイミダゾリウムテトラフルオロボレート、ヘキシルメチルイミダゾリウムヘキサフルオロホスフェート、1−エチル−3−メチルイミダゾリウムジエチルホスフェート、1−エチル−3−メチルイミダゾリウムメチルスルフェート、1−エチル−3−メチルイミダゾリウムビス[オキサレート(2−)−O,O+]ボレート、およびこれらの混合物から選択される、請求項1から3のいずれか1項に記載の潤滑組成物。
- イオン性液体は、メチルトリオクチルアンモニウム−トリフルオロアセテートおよびトリヘキシル(テトラデシル)ホスホニウム−ビス(トリフルオロメチルスルホニル)イミド、ヘキシルメチルイミダゾリウムテトラフルオロボレート、ヘキシルメチルイミダゾリウムヘキサフルオロホスフェート、1−エチル−3−メチルイミダゾリウムジエチルホスフェート、1−エチル−3−メチルイミダゾリウムメチルスルフェート、およびこれらの混合物から選択される、請求項1から3のいずれか1項に記載の潤滑組成物。
- イオン性液体は、トリヘキシル(テトラデシル)ホスホニウム−ビス(トリフルオロメチルスルホニル)イミド、ヘキシルメチルイミダゾリウムヘキサフルオロホスフェート、およびこれらの混合物から選択される、請求項1から5のいずれか1項に記載の潤滑組成物。
- ベースオイルは、ポリオールと式RCOOHのカルボン酸との反応によって形成される合成エステルであり、ここでRは5〜10個の炭素原子を有する直鎖または枝分れ鎖ヒドロカルビル基である、請求項1から6のいずれか1項に記載の潤滑組成物。
- タービンエンジンを潤滑するための、請求項1から7のいずれか1項に記載の潤滑組成物の使用。
- (i)ベースオイル、(ii)イオン性液体および(iii)1種以上の添加剤を含む潤滑組成物のスラッジ含有量を減少させるためのイオン性液体の使用であって、
イオン性液体は一般式がC + A − の塩であり、カチオンC + は、第四級アンモニウムカチオン、ホスホニウムカチオン、イミダゾリウムカチオン、ピリジニウムカチオン、ピラゾリウムカチオン、オキサゾリウムカチオン、ピロリジニウムカチオン、ピペリジニウムカチオン、トリアルキルスルホニウムカチオン、チアゾリウムカチオン、グアニジニウムカチオン、モルホリニウムカチオン、スルホニウムカチオンおよびトリアゾリウムカチオンから選択され、アニオンA − は、[PF 6 ] − 、[BF 4 ] − 、[CF 3 CO 2 ] − 、[CF 3 SO 3 ] − 、およびその高級同族体、[C 4 F 9 SO 3 ] − または[C 8 F 17 SO 3 ] − および高級ペルフルオロアルキルスルホネート、[(CF 3 SO 2 ) 2 N] − 、[(CF 3 SO 2 )(CF 3 COO)N] − 、Cl − 、Br − 、I − 、[C(CN) 3 ] − 、SCN − 、[B(C 2 O 4 ) 2 ] − 、[N(SO 2 CF 3 ) 2 ] − 、[R 4 SO 3 ] − 、[R 4 OSO 3 ] − 、[R 4 COO] − 、[NO 3 ] − 、[N(CN) 2 ] − 、[HSO 4 ] − 、PF 6−x R 6 x または[R 4 R 5 PO 4 ] − から選択され、ここでR 4 とR 5 は、水素、線状または枝分れした飽和または不飽和の脂肪族または脂環式アルキル基であって1〜20個の炭素原子を有するもの、ヘテロアリール基およびヘテロアリール−C 1 −C 6 −アルキル基であってヘテロアリール残基中の3〜8個の炭素原子とN、OおよびSから選択される少なくとも1個のヘテロ原子を有するもの(これらはC 1 −C 6 −アルキル基および/またはハロゲン原子から選択される少なくとも1個の群で置換することができる)、アリール−アリール−C 1 −C 6 −アルキル基であってアリール残基中の5〜12個の炭素原子を有するもの(これらは少なくとも1個のC 1 −C 6 −アルキル基で置換することができる)から独立して選択され、R 6 はペルフルオロエチル基または高級ペルフルオロアルキル基とすることができて、そしてxは1〜4の整数である、前記使用。 - (i)ベースオイル、(ii)イオン性液体および(iii)1種以上の添加剤を含む潤滑組成物のコーキングを減少させるためのイオン性液体の使用であって、
イオン性液体は一般式がC + A − の塩であり、カチオンC + は、第四級アンモニウムカチオン、ホスホニウムカチオン、イミダゾリウムカチオン、ピリジニウムカチオン、ピラゾリウムカチオン、オキサゾリウムカチオン、ピロリジニウムカチオン、ピペリジニウムカチオン、トリアルキルスルホニウムカチオン、チアゾリウムカチオン、グアニジニウムカチオン、モルホリニウムカチオン、スルホニウムカチオンおよびトリアゾリウムカチオンから選択され、アニオンA − は、[PF 6 ] − 、[BF 4 ] − 、[CF 3 CO 2 ] − 、[CF 3 SO 3 ] − 、およびその高級同族体、[C 4 F 9 SO 3 ] − または[C 8 F 17 SO 3 ] − および高級ペルフルオロアルキルスルホネート、[(CF 3 SO 2 ) 2 N] − 、[(CF 3 SO 2 )(CF 3 COO)N] − 、Cl − 、Br − 、I − 、[C(CN) 3 ] − 、SCN − 、[B(C 2 O 4 ) 2 ] − 、[N(SO 2 CF 3 ) 2 ] − 、[R 4 SO 3 ] − 、[R 4 OSO 3 ] − 、[R 4 COO] − 、[NO 3 ] − 、[N(CN) 2 ] − 、[HSO 4 ] − 、PF 6−x R 6 x または[R 4 R 5 PO 4 ] − から選択され、ここでR 4 とR 5 は、水素、線状または枝分れした飽和または不飽和の脂肪族または脂環式アルキル基であって1〜20個の炭素原子を有するもの、ヘテロアリール基およびヘテロアリール−C 1 −C 6 −アルキル基であってヘテロアリール残基中の3〜8個の炭素原子とN、OおよびSから選択される少なくとも1個のヘテロ原子を有するもの(これらはC 1 −C 6 −アルキル基および/またはハロゲン原子から選択される少なくとも1個の群で置換することができる)、アリール−アリール−C 1 −C 6 −アルキル基であってアリール残基中の5〜12個の炭素原子を有するもの(これらは少なくとも1個のC 1 −C 6 −アルキル基で置換することができる)から独立して選択され、R 6 はペルフルオロエチル基または高級ペルフルオロアルキル基とすることができて、そしてxは1〜4の整数である、前記使用。
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- 2010-09-07 US US13/394,179 patent/US20120178658A1/en not_active Abandoned
- 2010-09-07 RU RU2012113710/04A patent/RU2555703C2/ru active
- 2010-09-07 WO PCT/EP2010/063082 patent/WO2011026990A1/en active Application Filing
- 2010-09-07 JP JP2012528340A patent/JP5680648B2/ja active Active
- 2010-09-07 EP EP10749866A patent/EP2475753A1/en not_active Ceased
- 2010-09-07 CN CN201080047677.0A patent/CN102625827B/zh active Active
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CN102625827B (zh) | 2014-12-24 |
US20120178658A1 (en) | 2012-07-12 |
CN102625827A (zh) | 2012-08-01 |
WO2011026990A1 (en) | 2011-03-10 |
EP2475753A1 (en) | 2012-07-18 |
BR112012005155A2 (pt) | 2019-07-09 |
RU2012113710A (ru) | 2013-10-20 |
BR112012005155B1 (pt) | 2023-03-07 |
JP2013503957A (ja) | 2013-02-04 |
RU2555703C2 (ru) | 2015-07-10 |
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