CA2571104C - Synergistic lubricating oil composition containing a mixture of a benzo[b] perhydroheterocyclic arylamine and a diarylamine - Google Patents
Synergistic lubricating oil composition containing a mixture of a benzo[b] perhydroheterocyclic arylamine and a diarylamine Download PDFInfo
- Publication number
- CA2571104C CA2571104C CA2571104A CA2571104A CA2571104C CA 2571104 C CA2571104 C CA 2571104C CA 2571104 A CA2571104 A CA 2571104A CA 2571104 A CA2571104 A CA 2571104A CA 2571104 C CA2571104 C CA 2571104C
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- Canada
- Prior art keywords
- component
- composition according
- carbon atoms
- alkyl
- group
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 149
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 25
- 230000002195 synergetic effect Effects 0.000 title claims description 10
- 125000005266 diarylamine group Chemical group 0.000 title abstract description 21
- 125000005605 benzo group Chemical group 0.000 title abstract description 13
- 150000004982 aromatic amines Chemical class 0.000 title abstract description 12
- 239000003921 oil Substances 0.000 claims abstract description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- -1 amine phosphates Chemical class 0.000 claims description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 50
- 239000011593 sulfur Substances 0.000 claims description 49
- 229910052717 sulfur Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 43
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 239000003963 antioxidant agent Substances 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000005078 molybdenum compound Substances 0.000 claims description 20
- 150000002752 molybdenum compounds Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229960002317 succinimide Drugs 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 230000003078 antioxidant effect Effects 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 239000002270 dispersing agent Substances 0.000 claims description 13
- 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
- BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical compound ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 150000003017 phosphorus Chemical class 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 235000021317 phosphate Nutrition 0.000 claims description 7
- 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 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000005541 phosphonamide group Chemical group 0.000 claims description 5
- 150000008039 phosphoramides Chemical class 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims description 3
- JLYVRXJEQTZZBE-UHFFFAOYSA-N ctk1c6083 Chemical compound NP(N)(N)=S JLYVRXJEQTZZBE-UHFFFAOYSA-N 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- 125000005538 phosphinite group Chemical group 0.000 claims description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
- 150000003013 phosphoric acid derivatives 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
- 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 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
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 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
- 230000001050 lubricating effect Effects 0.000 abstract description 13
- 238000006388 chemical passivation reaction Methods 0.000 abstract description 4
- 235000019198 oils Nutrition 0.000 description 60
- 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
- 239000002199 base oil Substances 0.000 description 31
- 229910052750 molybdenum Inorganic materials 0.000 description 31
- 239000011733 molybdenum Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 29
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 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 19
- 238000007254 oxidation reaction Methods 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 14
- 150000002430 hydrocarbons Chemical class 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 238000002360 preparation method 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 239000000314 lubricant Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 150000002751 molybdenum Chemical class 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 229940035422 diphenylamine Drugs 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000012044 organic layer 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 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 class 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
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 229940014800 succinic anhydride Drugs 0.000 description 5
- 239000010689 synthetic lubricating oil Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-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
- 239000005977 Ethylene Substances 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
- 125000001931 aliphatic group Chemical group 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
- 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 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 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
- 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 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 4
- 229960001124 trientine Drugs 0.000 description 4
- 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 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
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000002947 alkylene group 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
- 239000003795 chemical substances by application Substances 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
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- 229910052945 inorganic sulfide Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 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
- 150000002978 peroxides Chemical class 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
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- 239000010452 phosphate Substances 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
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- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000011275 tar sand Substances 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
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- 238000004448 titration Methods 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
- 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
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- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- 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
-
- 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
-
- 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
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
-
- 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
- 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—Overbased sulfonic acid salts
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/316,451 US7501386B2 (en) | 2005-12-21 | 2005-12-21 | Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine |
| US11/316,451 | 2005-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2571104A1 CA2571104A1 (en) | 2007-06-21 |
| CA2571104C true CA2571104C (en) | 2015-03-10 |
Family
ID=37944389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2571104A Expired - Fee Related CA2571104C (en) | 2005-12-21 | 2006-12-13 | Synergistic lubricating oil composition containing a mixture of a benzo[b] perhydroheterocyclic arylamine and a diarylamine |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7501386B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1801189B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5086631B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2571104C (cg-RX-API-DMAC7.html) |
| SG (1) | SG133567A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7285518B2 (en) * | 2005-12-21 | 2007-10-23 | Chevron Oronite Company Llc | Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions |
| US8003583B2 (en) * | 2005-12-21 | 2011-08-23 | Chevron Oronite Company Llc | Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions |
| EP2142624B1 (en) * | 2007-04-25 | 2017-09-06 | Dow Global Technologies LLC | Lubricant blend composition |
| US7879934B2 (en) * | 2007-08-16 | 2011-02-01 | Chemtura Corporation | Rubber compositions |
| EP2077315B1 (en) * | 2007-12-20 | 2012-10-31 | Chevron Oronite Company LLC | Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant and a diarylamine antioxidant |
| US8623798B2 (en) * | 2007-12-20 | 2014-01-07 | Chevron Oronite Company Llc | Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant |
| US20100081591A1 (en) * | 2008-09-30 | 2010-04-01 | Chevron Oronite Company Llc | Lubricating oil compositions |
| BR112013030491A2 (pt) * | 2011-05-31 | 2017-08-08 | Lubrizol Corp | composição lubrificante com retenção de nbt melhorada |
| US9752092B2 (en) * | 2015-10-30 | 2017-09-05 | Chevron Oronite Company Llc | Lubricating oil compositions containing amidine antioxidants |
| US10077410B2 (en) * | 2016-07-13 | 2018-09-18 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing mixture of antioxidants |
| US10723969B2 (en) * | 2016-09-20 | 2020-07-28 | Lanxess Solutions Us Inc. | Lubricant compositions stabilized by mixtures of diarylamine and hydroxydiarylamine antioxidants |
| EP3516018A1 (en) | 2016-09-20 | 2019-07-31 | Lanxess Solutions US Inc. | Alkylated alkoxydiarylamine antioxidants |
| CN109642177B (zh) | 2016-09-20 | 2022-01-04 | 朗盛解决方案美国公司 | 烷基化3-羟基二苯胺抗氧化剂 |
| EP4267707A1 (en) | 2020-12-23 | 2023-11-01 | The Lubrizol Corporation | Benzazepine compounds as antioxidants for lubricant compositions |
| EP4704835A2 (en) * | 2023-05-05 | 2026-03-11 | Flexsys IP Holdings, LLC | Antidegradant bis(dihydro and tetrahydroquinoline) compounds and uses thereof |
| TWI912188B (zh) * | 2025-04-16 | 2026-01-11 | 國立中央大學 | 二芳基胺及其製備方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1896461A (en) | 1927-02-14 | 1933-02-07 | Gen Aniline Works Inc | Indophenols and leucoindophenols of the azine series |
| US2342135A (en) | 1941-08-07 | 1944-02-22 | Goodrich Co B F | Arylamino dihydrobenzofurane |
| US2366018A (en) * | 1943-10-15 | 1944-12-26 | Goodrich Co B F | Antioxidant |
| US2419334A (en) * | 1943-12-10 | 1947-04-22 | American Cyanamid Co | Derivatives of amino-benzo-p-dioxans |
| US2718501A (en) | 1952-03-01 | 1955-09-20 | California Research Corp | Oils stable against oxidation |
| US2794020A (en) | 1953-08-03 | 1957-05-28 | Monsanto Chemicals | 6-amino substituted 1, 2, 3, 4-tetrahydroquinolines |
| US2998468A (en) | 1954-10-11 | 1961-08-29 | Monsanto Chemicals | Method of preserving natural rubber by adding thereto 2:2:4-trimethyl-decahydroquinoline and a substituted phenol |
| US2943112A (en) | 1957-11-06 | 1960-06-28 | Pennsalt Chemicals Corp | Alkylation of diphenylamine |
| US2956663A (en) * | 1958-04-09 | 1960-10-18 | West Point Mfg Co | Floor conveyor for card sliver cans |
| NL240511A (cg-RX-API-DMAC7.html) | 1958-06-25 | |||
| US3121691A (en) * | 1960-05-24 | 1964-02-18 | Sinclair Research Inc | Lubricant composition |
| US3345992A (en) | 1965-08-04 | 1967-10-10 | Vacudyne Corp | Method for conditioning tobacco |
| US3362929A (en) | 1966-03-01 | 1968-01-09 | Goodrich Co B F | Ozone resistant composition |
| US3944492A (en) | 1966-04-07 | 1976-03-16 | Uniroyal, Inc. | Lubricant compositions containing N-substituted naphthylamines as antioxidants |
| US3452056A (en) | 1966-04-07 | 1969-06-24 | Uniroyal Inc | Substituted diphenylamines |
| US3533992A (en) | 1966-04-07 | 1970-10-13 | Uniroyal Inc | Conjugated diolefin polymer rubber containing substituted diphenylamines as antioxidant |
| US3480635A (en) | 1966-09-28 | 1969-11-25 | Universal Oil Prod Co | N-piperidyl substituted phenylenediamines |
| GB1236740A (en) | 1969-04-11 | 1971-06-23 | Geigy Uk Ltd | Tertiary alkylated diphenylamines and their uses as antioxidants |
| BE756024A (nl) | 1969-09-22 | 1971-03-11 | Shell Int Research | Alkyl-gesubstitueerde fenylnaftylaminen en smeermiddelcomposities die deze bevatten |
| US3910918A (en) | 1971-04-26 | 1975-10-07 | Heliodoro Monroy | 1,2-Dihydroquinolines and process and apparatus for the obtention thereof |
| US4198134A (en) * | 1974-12-23 | 1980-04-15 | Montron Corporation | Film cartridge |
| US4089792A (en) | 1976-04-01 | 1978-05-16 | Chevron Research Company | Synergistic antioxidant additive composition |
| US4069195A (en) | 1976-06-18 | 1978-01-17 | The B.F. Goodrich Company | Substituted decahydroquinolines and their use as ultraviolet light stabilizer |
| CA1138472A (en) | 1979-05-21 | 1982-12-28 | Baldev K. Bandlish | ANTIOXIDANT FOR POLYESTER FLUIDS .alpha. - METHYL - N PHENYLBENZENEMETHANAMINE |
| CA1153757A (en) | 1979-05-31 | 1983-09-13 | Baldev K. Bandlish | Stabilizer systems for lubricating fluids |
| DE3276326D1 (en) | 1981-08-10 | 1987-06-19 | Ciba Geigy Ag | Tetrahydroquinoline as an antioxidant for lubricants |
| US4828741A (en) | 1986-12-30 | 1989-05-09 | Ciba-Geigy Corporation | N-substituted tetrahydroquinolines for use as antioxidants in lubricants |
| US5232614A (en) | 1989-02-23 | 1993-08-03 | Exxon Chemical Patents Inc. | Lubricating oil compositions and additives for use therein |
| EP0497735A1 (de) * | 1991-01-31 | 1992-08-05 | Ciba-Geigy Ag | Hydrochinolinverbindungen |
| US5198134A (en) | 1991-05-07 | 1993-03-30 | Ciba-Geigy Corporation | Substituted naphthalenediamine stabilizers |
| US5310491A (en) | 1993-04-13 | 1994-05-10 | Uniroyal Chemical Company, Inc. | Lubricant composition containing antioxidant |
| US5451702A (en) | 1993-04-26 | 1995-09-19 | Monsanto Company | Process for preparing substituted aromatic amines |
| DE69405410T2 (de) | 1993-12-15 | 1998-03-19 | Goodrich Co B F | Stabilisatormischung für synthetisches estergleitmittel |
| US5420354A (en) | 1994-10-06 | 1995-05-30 | Uniroyal Chemical Company, Inc. | Process of preparing para phenylamines |
| US5595963A (en) | 1994-12-05 | 1997-01-21 | Exxon Chemical Patents Inc. | Synergistic antioxidant combinations for lubricating oils |
| CA2202790C (en) | 1994-12-09 | 2004-02-24 | Raymond Frederick Watts | Synergistic antioxidant systems |
| SG65759A1 (en) | 1997-06-06 | 1999-06-22 | Ciba Sc Holding Ag | Nonylated diphenylamines |
| US5834544A (en) | 1997-10-20 | 1998-11-10 | Uniroyal Chemical Company, Inc. | Organic materials stabilized by compounds containing both amine and hindered phenol functional functionalities |
| JP3819579B2 (ja) * | 1998-02-06 | 2006-09-13 | 株式会社ジェイテクト | 生分解性グリース組成物 |
| US6174842B1 (en) | 1999-03-30 | 2001-01-16 | Ethyl Corporation | Lubricants containing molybdenum compounds, phenates and diarylamines |
| WO2003027215A2 (en) | 2001-09-21 | 2003-04-03 | R.T. Vanderbilt Company, Inc. | Improved antioxydant additive compositions and lubricating compositions containing the same |
| US20040087451A1 (en) * | 2002-10-31 | 2004-05-06 | Roby Stephen H. | Low-phosphorus lubricating oil composition for extended drain intervals |
-
2005
- 2005-12-21 US US11/316,451 patent/US7501386B2/en active Active
-
2006
- 2006-12-07 EP EP06256230A patent/EP1801189B1/en not_active Ceased
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| EP1801189A3 (en) | 2010-07-28 |
| EP1801189A2 (en) | 2007-06-27 |
| SG133567A1 (en) | 2007-07-30 |
| JP2007169644A (ja) | 2007-07-05 |
| US20070142243A1 (en) | 2007-06-21 |
| CA2571104A1 (en) | 2007-06-21 |
| JP5086631B2 (ja) | 2012-11-28 |
| EP1801189B1 (en) | 2012-11-07 |
| US7501386B2 (en) | 2009-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20201214 |