JP5086631B2 - ベンゾ[b]ペルヒドロ複素環アリールアミンとジアリールアミンとの混合物を含む相乗的潤滑油組成物 - Google Patents
ベンゾ[b]ペルヒドロ複素環アリールアミンとジアリールアミンとの混合物を含む相乗的潤滑油組成物 Download PDFInfo
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- JP5086631B2 JP5086631B2 JP2006343424A JP2006343424A JP5086631B2 JP 5086631 B2 JP5086631 B2 JP 5086631B2 JP 2006343424 A JP2006343424 A JP 2006343424A JP 2006343424 A JP2006343424 A JP 2006343424A JP 5086631 B2 JP5086631 B2 JP 5086631B2
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- 239000000203 mixture Substances 0.000 title claims description 142
- 239000010687 lubricating oil Substances 0.000 title claims description 31
- 230000002195 synergetic effect Effects 0.000 title claims description 12
- 125000005266 diarylamine group Chemical group 0.000 title description 20
- 125000005605 benzo group Chemical group 0.000 title description 14
- 150000004982 aromatic amines Chemical class 0.000 title description 11
- -1 amine phosphate esters Chemical class 0.000 claims description 89
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 47
- 239000011593 sulfur Substances 0.000 claims description 47
- 229910052717 sulfur Inorganic materials 0.000 claims description 47
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 239000003963 antioxidant agent Substances 0.000 claims description 28
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 28
- 229930195733 hydrocarbon Natural products 0.000 claims description 25
- 150000002430 hydrocarbons Chemical class 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 20
- 229960002317 succinimide Drugs 0.000 claims description 20
- 239000005078 molybdenum compound Substances 0.000 claims description 19
- 150000002752 molybdenum compounds Chemical class 0.000 claims description 19
- 239000011574 phosphorus Substances 0.000 claims description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 230000003078 antioxidant effect Effects 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 13
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 239000002270 dispersing agent Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005541 phosphonamide group Chemical group 0.000 claims description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 150000003017 phosphorus Chemical class 0.000 claims description 3
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 claims description 2
- JWXNJZPOYUARDX-UHFFFAOYSA-N 2-tert-butyl-n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical compound C=1C=CC=C(C(C)(C)C)C=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 JWXNJZPOYUARDX-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims 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 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- JLYVRXJEQTZZBE-UHFFFAOYSA-N ctk1c6083 Chemical compound NP(N)(N)=S JLYVRXJEQTZZBE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 2
- RNBMWJIBIBMXDK-UHFFFAOYSA-N 2,3-dibutyl-N-phenylaniline Chemical compound C(CCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCC RNBMWJIBIBMXDK-UHFFFAOYSA-N 0.000 claims 1
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims 1
- SRENRFDRXNVMKN-UHFFFAOYSA-N n-butyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCC)C1=CC=CC=C1 SRENRFDRXNVMKN-UHFFFAOYSA-N 0.000 claims 1
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 claims 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 claims 1
- 150000008301 phosphite esters Chemical class 0.000 claims 1
- 239000003921 oil Substances 0.000 description 55
- 235000019198 oils Nutrition 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 229910052750 molybdenum Inorganic materials 0.000 description 34
- 239000011733 molybdenum Substances 0.000 description 34
- 239000002199 base oil Substances 0.000 description 33
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 230000003647 oxidation Effects 0.000 description 20
- 238000007254 oxidation reaction Methods 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 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
- 239000011541 reaction mixture Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 9
- 239000000314 lubricant Substances 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 230000001050 lubricating effect Effects 0.000 description 6
- 150000002751 molybdenum Chemical class 0.000 description 6
- 239000005077 polysulfide Substances 0.000 description 6
- 229920001021 polysulfide Polymers 0.000 description 6
- 150000008117 polysulfides Polymers 0.000 description 6
- 150000003839 salts Chemical group 0.000 description 6
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000010689 synthetic lubricating oil Substances 0.000 description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- TZSNBHPFGNSWPO-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;platinum Chemical compound [Pt].[Pt].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 TZSNBHPFGNSWPO-UHFFFAOYSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 4
- 239000011609 ammonium molybdate Substances 0.000 description 4
- 235000018660 ammonium molybdate Nutrition 0.000 description 4
- 229940010552 ammonium molybdate Drugs 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 4
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- IMECLEIGZREVBB-UHFFFAOYSA-N n-phenyl-1,2,3,4-tetrahydroquinolin-6-amine Chemical compound C1=C2CCCNC2=CC=C1NC1=CC=CC=C1 IMECLEIGZREVBB-UHFFFAOYSA-N 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 4
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 229910052945 inorganic sulfide Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000036284 oxygen consumption Effects 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical class C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
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- YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- JYTMDBGMUIAIQH-ZPHPHTNESA-N palmityl oleate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC JYTMDBGMUIAIQH-ZPHPHTNESA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 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
- 229940066675 ricinoleate Drugs 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
- 239000005060 rubber Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
- YYMWVZQRBNARFZ-UHFFFAOYSA-M sodium;2-[2,3-bis(sulfanyl)propoxy]ethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCOCC(S)CS YYMWVZQRBNARFZ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 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
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000011275 tar sand Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- IJTNSXPMYKJZPR-BYFNFPHLSA-N trans-parinaric acid Chemical compound CC\C=C\C=C\C=C\C=C\CCCCCCCC(O)=O IJTNSXPMYKJZPR-BYFNFPHLSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
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- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
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- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
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- C—CHEMISTRY; METALLURGY
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- 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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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Description
a)0.1乃至10質量%の下記I式に従う第一の酸化防止剤:
各R3は、水素または炭素原子数1〜6のアルキルであり、
XおよびX’は独立に、−CHR4−、酸素、硫黄またはNR5(ただし、R4およびR5は独立に水素または炭素原子数1〜6のアルキルである)から選ばれるが、XまたはX’のうちの少なくとも一方は架橋窒素原子に対してオルト又はパラ位に位置するヘテロ原子であり、またXあるいはX’が窒素であるときにはR1またはR2はヒドロキシルではなく、更にXまたはX’のうちの一方が−CHR4−であるときにはもう一方は酸素ではない、そして
nは、1もしくは2の整数である]、
および
b)0.01乃至10質量%の下記式の第二の酸化防止剤:
a)成分は、単独で酸化防止剤、耐オゾン剤、熱安定剤および紫外線安定剤として有用なベンゾ[b]ペルヒドロ複素環アリールアミンであり、そしてこれらの化合物は油溶性であるから、特に潤滑油組成物に酸化防止剤として使用するのに適している。ここに開示するのは、特に好適な下記I式に従う共鳴安定化した防止剤化合物である:
第二級ジアリールアミンはよく知られた酸化防止剤である。好ましくは第二級ジアリールアミン酸化防止剤は、一般式Ra−NH−Rb(ただし、RaおよびRbは各々独立に炭素原子数C6−C30の置換又は非置換アリール基を表し、好ましくはRaおよびRbは各々独立に、非置換であってもあるいは各々炭素原子数1〜20の1又は2個のアルキル基で置換されていてもよい、炭素原子数6〜10のアリールである)のうちの一つである。
本発明の潤滑油組成物は、主要量の潤滑粘度の基油を含有している。基油は、本明細書で使用するとき、単一の製造者により同一の仕様に(供給源や製造者の所在地とは無関係に)製造され、同じ製造者の仕様を満たし、そして独特の処方、製造物確認番号またはその両方によって識別される潤滑油成分である、基材油または基材油のブレンドと定義される。蒸留、溶剤精製、水素処理、オリゴマー化、エステル化および再精製を含むが、それらに限定されない各種の異なる方法を使用して基材油を製造することができる。再精製基材油には、製造、汚染もしくは以前の使用によって混入した物質が実質的に含まれない。本発明の基油は、任意の天然または合成の潤滑基油留分であってよく、特には、動粘度が摂氏100度(℃)で約5センチストークス(cSt)乃至約20cSt、好ましくは約7cSt乃至約16cSt、より好ましくは約9cSt乃至約15cStのものである。炭化水素合成油としては例えば、エチレンの重合から製造された油、すなわちポリアルファオレフィン又はPAO、あるいはフィッシャー・トロプシュ法などの一酸化炭素ガスと水素ガスを用いる炭化水素合成法により製造された油を挙げることができる。好ましい基油は、重質留分を含む場合でもその量が僅かである、例えば約100℃粘度が20cSt又はそれ以上の潤滑油留分を殆ど含むことのない油である。
I、II及びIII種基材油の飽和度、硫黄及び粘度指数
─────────────────────────────────────
種類 飽和度(ASTM 粘度指数(ASTM D4294、
D2007に規定) ASTM D4297又は
硫黄(ASTM ASTM D3120に規定)
D2270に規定)
─────────────────────────────────────
I 飽和度90%未満及び/又は 80以上、120未満
硫黄0.03%より上
II 飽和度90%以上及び 80以上、120未満
硫黄0.03%以下
III 飽和度90%以上及び 120以上
硫黄0.03%以下
─────────────────────────────────────
油溶性モリブデン化合物およびモリブデン/硫黄錯体は、当該分野では知られていて、例えば米国特許第4263152号(キング、外)及び第6962896号(リューエ)の各明細書に記載されており、その開示内容も参照内容として本明細書の記載とするが、特に好ましいものである。本発明に使用することができるモリブデン化合物のその他の代表的なものとしては、次のものが挙げられる:米国特許第3285942号(プライス、外)明細書に記載されているモリブデン酸グリコール錯体;米国特許第4832857号(ハント、外)明細書に開示され特許請求されているもののような、モリブデンを含む過塩基性アルカリ金属及びアルカリ土類金属スルホネート、フェネート及びサリチレート組成物;米国特許第4889647号(ローワン、外)明細書に記載されているように、脂肪油、ジエタノールアミンおよびモリブデン源を反応させることにより製造されたモリブデン錯体;米国特許第5137647号(カロル)明細書に記載されているように、脂肪酸と2−(2−アミノエチル)アミノエタノールから製造されたモリブデン含有化合物などの、有機アミドの無硫黄無リンオルガノモリブデン錯体、および脂肪油または脂肪酸から誘導された脂肪残渣が置換した1−(2−ヒドロキシエチル)−2−イミダゾリンから製造されたモリブデン含有化合物;米国特許第5143633号(ガロ、外)明細書に記載されているように、アミン、ジアミン、アルコキシル化アミン、グリコールおよびポリオールから製造された過塩基性モリブデン錯体;米国特許第5412130号(カロル)明細書に記載されている2,4−ヘテロ原子置換−モリブデナ−3,3−ジオキサシクロアルカン;およびそれらの混合物。上記のうち代表的なモリブデン化合物は市販されていて、これらに限定されるものではないが、次のものが挙げられる:サクラ−ルーベ(Sakura-Lube、商品名)700、旭電化工業(株)(Asahi Denka Kogyo K.K.、東京) 製、モリブデンアミン錯体;モリブデンHEX−CEM(商品名)、OMグループ(OM Group, Inc.、オハイオ州クリーブランド)製、2−エチルヘキサン酸モリブデン;オクタン酸モリブデン、シェファード・ケミカル・カンパニー(Shepherd Chemical Company、オハイオ州シンシナティ)製、2−エチルヘキサン酸モリブデン;モリヴァン(Molyvan、商品名)855、R.T.ヴァンダービルト・カンパニー(コネチカット州ノーウォーク)製、有機アミドの無硫黄無リンオルガノモリブデン錯体;モリヴァン856−B(商品名)、同じくR.T.ヴァンダービルト製、オルガノモリブデン錯体。
1)フェノール型(フェノール系)酸化防止剤:4,4’−メチレンビス(2,6−ジ−t−ブチルフェノール)、4,4’−ビス(2,6−ジ−t−ブチルフェノール)、4,4’−ビス(2−メチル−6−t−ブチルフェノール)、2,2’−(メチレンビス(4−メチル−6−t−ブチルフェノール))、4,4’−ブチリデンビス(3−メチル−6−t−ブチルフェノール)、4,4’−イソプロピリデンビス(2,6−ジ−t−ブチルフェノール)、2,2’−メチレンビス(4−メチル−6−ノニルフェノール)、2,2’−イソブチリデンビス(4,6−ジメチルフェノール)、2,2’−メチレンビス(4−メチル−6−シクロヘキシルフェノール)、2,6−ジ−t−ブチル−4−メチルフェノール、2,6−ジ−t−ブチル−4−エチルフェノール、2,4−ジメチル−6−t−ブチルフェノール、2,6−ジ−t−α−ジメチルアミノ−p−クレゾール、2,6−ジ−t−4−(N,N’−ジメチルアミノメチルフェノール)、4,4’−チオビス(2−メチル−6−t−ブチルフェノール)、2,2’−チオビス(4−メチル−6−t−ブチルフェノール)、ビス(3−メチル−4−ヒドロキシ−5−t−ブチルベンジル)−スルフィド、およびビス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)。
1)非イオン性ポリオキシエチレン界面活性剤:ポリオキシエチレンラウリルエーテル、ポリオキシエチレン高級アルコールエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンオクチルステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンソルビトールモノステアレート、ポリオキシエチレンソルビトールモノオレエート、およびポリエチレングリコールモノオレエート。
選択した実施例の生成物の酸化研究を、E.S.ヤマグチ(E.S.Yamaguchi)、外著、トライボロジー・トランスアクションズ(Tribology Transactions)、第42(4)巻、p.895−901、1999年に記載されているように、バルク油酸化台上試験にて行った。この試験では、一定質量の油による定圧での酸素消費の速度をモニタした。試料25グラム当りの急速酸素消費に要する時間(誘導時間)を、171℃、酸素圧1.0気圧で測定した。試料を毎分1000回転で撹拌した。結果は、試料100グラム当りの急速酸素消費に要した時間で報告する。油は、油溶性ナフテネートとして加えた触媒を含み、鉄26ppm、銅45ppm、鉛512ppm、マンガン2.3ppmおよびスズ24ppmであった。
a)成分のI式のベンゾ[b]ペルヒドロ複素環アリールアミンと、b)成分のジアリールアミンとの混合物の性能を酸化台上試験で評価するために、基本配合物を製造した。基本配合物−配合物Aは、2+種の基油中に、ジアルキルジチオリン酸亜鉛12.5ミリモル/kg、ポリイソブテニルコハク酸イミド5.0%、過塩基性カルシウムスルホネート清浄剤35.0ミリモル/kg、カルシウムフェネート清浄剤15.0ミリモル/kg、およびVI向上剤0.3%を含有している。基本配合物Aを上記のバルク油酸化台上試験で試験して、その結果、急速O2消費に対して11.5時間の値を得た。この基本配合物(配合物A)にa)成分とb)成分を量を変えて添加したが、a)成分とb)成分の総添加量は1質量%で一定に保った。
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性能 配合物Aに仕上げ処理した相乗混合物 結果
実施例 a)成分 b)成分 急速O2消費
実施例1の濃度 アルキル化ジフェニル の時間
(質量%) アミン1の濃度(質量%)
──────────────────────────────────
1 0 1 33.0
2 0.15 0.85 38.0
3 0.3 0.7 47.0
4 0.45 0.55 55.0
5 0.6 0.4 60.0
6 0.75 0.25 70.0
7 0.9 0.1 60.0
8 1 0 54.0
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1:イルガノックスL57はチバ・ガイギーより市販されている。
a)成分のI式のベンゾ[b]ペルヒドロ複素環アリールアミンと、b)成分のジアリールアミンとの混合物の性能を酸化台上試験で評価するために、第二の基本配合物を製造した。これらの実施例のb)成分は、上記で使用したのと同じb)成分である。配合物Bは、2+種の基油中に、ジアルキルジチオリン酸亜鉛7.0ミリモル/kg、ポリイソブテニルコハク酸イミド4.0%、ポリイソブテニルコハク酸イミド(このポリイソブテニルコハク酸イミドはモリブデン5.5質量%も含む)0.5%、過塩基性カルシウムスルホネート清浄剤48.5ミリモル/kg、およびVI向上剤0.3%を含有した。上記と同様に、第2表の性能実施例9及び16はb)成分とa)成分それぞれの寄与を示している。第2表に示すように、少量のa)成分をb)成分に添加すると、どちらかの成分単独よりも優れた結果を生むことができる、例えば性能実施例11−15を参照されたい。
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性能 配合物Bに仕上げ処理した相乗混合物 結果
実施例 a)成分 b)成分 急速O2消費
実施例1の濃度 アルキル化ジフェニル の時間
(質量%) アミンの濃度(質量%)
──────────────────────────────────
9 0 1 38.0
10 0.15 0.85 58.0
11 0.3 0.7 71.5
12 0.45 0.55 82.0
13 0.6 0.4 95.0
14 0.75 0.25 100.0
15 0.9 0.1 95.0
16 1.0 0 71.5
──────────────────────────────────
a)成分のI式のベンゾ[b]ペルヒドロ複素環アリールアミン0.375質量%と、b)成分のジアリールアミン0.125質量%との混合物の性能を、c)成分の米国特許第6962896号(リューエ)明細書に記載のようにして製造したモリブデン含有ポリイソブテニルコハク酸イミド(このポリイソブテニルコハク酸イミドはモリブデン5.5質量%を含む)の量を変えて、酸化台上試験で評価するために、第三の基本配合物を製造した。これらの実施例のa)及びb)成分は、上記で使用したのと同じa)及びb)成分である。配合物Cは、2+種基油中に、ジアルキルジチオリン酸亜鉛7.0ミリモル/kg、ポリイソブテニルコハク酸イミド4.0%、過塩基性カルシウムスルホネート清浄剤48.5ミリモル/kg、VI向上剤0.3%、フェニル−(1,2,3,4−テトラヒドロ−キノリン−6−イル)−アミン0.375%、およびイルガノックスL570.125%を含有した。第1表及び第2表のデータ全体の比較と同じように、第3表の性能実施例17−24も、a)成分とb)成分の組合せにc)成分を添加すると、それらの性能が増大することを示している。
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性能 c)成分の濃度 結果
実施例 (質量%) 急速O2消費の時間
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17 0 26.0
18 0.125 31.0
19 0.250 34.5
20 0.500 42.0
21 0.750 48.0
22 1.000 55.5
23 1.500 55.0
24 2.000 47.5
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Claims (27)
- 潤滑油、及び下記の成分を含む酸化防止剤の相乗的混合物を含有する組成物:
a)0.1乃至10質量%の下記I式に従う第一の酸化防止剤:
R3のそれぞれは、水素または炭素原子数1〜6のアルキルであり、
XおよびX’は独立に、−CHR4−、酸素、硫黄またはNR5(ただし、R4およびR5は独立に水素または炭素原子数1〜6のアルキルである)から選ばれるが、XまたはX’のうちの少なくとも一方は架橋窒素原子に対してオルト又はパラ位に位置するヘテロ原子であり、またXまたはX’が窒素であるときには、R1またはR2はヒドロキシルではなく、更にXまたはX’のうちの一方が−CHR4−であるときには、他の一方は酸素ではな
い、そして
nは、1もしくは2の整数である]
および
b)0.01乃至10質量%の下記式に従う第二の酸化防止剤:
- a)成分とb)成分との比が0.5:1乃至10:1である請求項1に記載の組成物。
- a)成分とb)成分との比が0.75:1乃至5:1である請求項2に記載の組成物。
- 組成物中の酸化防止剤の混合物の全質量%が5質量%未満である請求項2に記載の組成物。
- a)成分において、XおよびX’のうちの少なくとも一方がNR5および酸素から選ば
れる請求項1に記載の組成物。 - a)成分において、XおよびX’のうちの少なくとも一方がNR5である請求項5に記
載の組成物。 - a)成分において、Xが−CHR4−であり、そしてX’がNR5である請求項6に記載の組成物。
- a)成分において、nが2である請求項7に記載の組成物。
- a)成分において、R3、R4およびR5が各々水素である請求項8に記載の組成物。
- a)成分において、R1およびR2が各々独立に、水素および炭素原子数1〜20のアルキルからなる群より選ばれるが、R1およびR2が互いに隣接している場合には一緒に、各々炭素原子数1〜20の一又は二個のアルキル基で任意に置換されていてもよい五乃至六員の脂環族環又は芳香環を形成している請求項7に記載の組成物。
- a)成分において、R1およびR2が各々独立に、水素および炭素原子数1〜20のアルキルからなる群より選ばれる請求項10に記載の組成物。
- a)成分において、XおよびX’のうちの少なくとも一方が硫黄である請求項5に記載の組成物。
- a)成分において、XおよびX’が独立に、酸素、硫黄またはNR5(ただし、R5は水素または炭素原子数1〜6のアルキルである)から選ばれる請求項5に記載の組成物。
- a)成分において、XおよびX’が酸素である請求項13に記載の組成物。
- a)成分において、R1およびR2が互いに隣接していて、一緒に、各々炭素原子数1〜6の一又は二個のアルキル基で任意に置換されていてもよい五乃至六員の芳香環を形成している請求項1に記載の組成物。
- a)成分において、R1が水素であり、そしてR2が、炭素原子数1〜20のアルキル、−OR、−SRおよび−NRR’(ただし、RおよびR’は独立に水素または炭素原子数1〜6のアルキルである)からなる群より選ばれる請求項1に記載の組成物。
- a)成分において、R2が−NRR’(ただし、RおよびR’は炭素原子数1〜6のア
ルキルである)である請求項16に記載の組成物。 - b)成分が、ジフェニルアミン、モノアルキル化ジフェニルアミン、ジアルキル化ジフェニルアミン、トリアルキル化ジフェニルアミンおよびそれらの混合物からなる群より選ばれる請求項1に記載の組成物。
- b)成分が、ブチルジフェニルアミン、ジ−ブチルジフェニルアミン、オクチルジフェニルアミン、ジ−オクチルジフェニルアミン、ノニルジフェニルアミン、ジ−ノニルジフェニルアミン、t−ブチル−t−オクチルジフェニルアミンおよびそれらの混合物からなる群より選ばれる請求項18に記載の組成物。
- b)成分が、フェニル−アルファ−ナフチルアミン、フェニル−ベータ−ナフチルアミン、及びt−オクチル化N−フェニル−1−ナフチルアミンからなる群より選ばれる請求項18に記載の組成物。
- さらに、油溶性モリブデン化合物をc)成分として含む請求項1に記載の組成物。
- c)成分が、(i)酸性モリブデン化合物と、コハク酸イミド、カルボン酸アミド、炭化水素モノアミン、ホスホルアミド、チオホスホルアミド、マンニッヒ塩基、分散型粘度指数向上剤またはそれらの混合物からなる分散剤群から選ばれた塩基性窒素化合物とを、極性促進剤の存在下で反応させてオキシモリブデン錯体を生成させることにより製造された、未硫化又は硫化のオキシモリブデン含有組成物である請求項21に記載の組成物。
- 塩基性窒素化合物がコハク酸イミドである請求項22に記載の組成物。
- さらに、金属ジチオリン酸塩、リン酸エステル、アミンリン酸エステルおよびアミンホスフィン酸エステル、硫黄含有リンエステル、リンアミドおよびホスホンアミドからなる群より選ばれる油溶性のリン含有耐摩耗性化合物を含有する請求項1に記載の組成物。
- 該リン酸エステルが、リン酸エステル、ホスホン酸エステル、ホスフィン酸エステル、酸化ホスフィン、亜リン酸エステル、亜ホスホン酸エステル、亜ホスフィン酸エステルおよびホスフィンからなる群より選ばれる請求項24に記載の組成物。
- 油溶性のリン含有耐摩耗性化合物が金属ジチオリン酸塩である請求項24に記載の組成物。
- 金属ジチオリン酸塩がジアルキルジチオリン酸亜鉛である請求項26に記載の組成物。
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-
2005
- 2005-12-21 US US11/316,451 patent/US7501386B2/en active Active
-
2006
- 2006-12-07 EP EP06256230A patent/EP1801189B1/en active Active
- 2006-12-13 CA CA2571104A patent/CA2571104C/en not_active Expired - Fee Related
- 2006-12-20 JP JP2006343424A patent/JP5086631B2/ja not_active Expired - Fee Related
- 2006-12-21 SG SG200608983-3A patent/SG133567A1/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014218512A (ja) * | 2005-12-21 | 2014-11-20 | シェブロン・オロナイト・カンパニー・エルエルシー | ジベンゾ[b]ペルヒドロ複素環アミンおよび潤滑油組成物 |
Also Published As
Publication number | Publication date |
---|---|
US7501386B2 (en) | 2009-03-10 |
EP1801189B1 (en) | 2012-11-07 |
EP1801189A3 (en) | 2010-07-28 |
US20070142243A1 (en) | 2007-06-21 |
CA2571104C (en) | 2015-03-10 |
SG133567A1 (en) | 2007-07-30 |
JP2007169644A (ja) | 2007-07-05 |
EP1801189A2 (en) | 2007-06-27 |
CA2571104A1 (en) | 2007-06-21 |
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