EP0768366A1 - Composition d'huile lubrifiante - Google Patents
Composition d'huile lubrifiante Download PDFInfo
- Publication number
- EP0768366A1 EP0768366A1 EP96307382A EP96307382A EP0768366A1 EP 0768366 A1 EP0768366 A1 EP 0768366A1 EP 96307382 A EP96307382 A EP 96307382A EP 96307382 A EP96307382 A EP 96307382A EP 0768366 A1 EP0768366 A1 EP 0768366A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dithiophosphate
- zinc
- lubricating oil
- carbon atoms
- oil composition
- 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.)
- Granted
Links
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 129
- 239000000203 mixture Substances 0.000 title claims abstract description 111
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 108
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 95
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 95
- 239000011701 zinc Substances 0.000 claims abstract description 94
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 43
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 43
- 239000011574 phosphorus Substances 0.000 claims abstract description 43
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000012990 dithiocarbamate Substances 0.000 claims abstract description 29
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 17
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011593 sulfur Substances 0.000 claims abstract description 17
- 150000003464 sulfur compounds Chemical class 0.000 claims abstract description 14
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002199 base oil Substances 0.000 claims abstract description 10
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 10
- 239000011733 molybdenum Substances 0.000 claims abstract description 10
- 230000001050 lubricating effect Effects 0.000 claims abstract description 7
- 239000000654 additive Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
- -1 olefin sulfides Chemical class 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 150000002019 disulfides Chemical class 0.000 claims description 12
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 235000021323 fish oil Nutrition 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 239000010698 whale oil Substances 0.000 claims description 6
- 150000004867 thiadiazoles Chemical class 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 29
- 230000003647 oxidation Effects 0.000 abstract description 26
- 238000007254 oxidation reaction Methods 0.000 abstract description 26
- 238000002485 combustion reaction Methods 0.000 abstract description 16
- 238000002360 preparation method Methods 0.000 description 18
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 125000002704 decyl 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])* 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 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 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 125000001400 nonyl 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])[H] 0.000 description 6
- 125000002347 octyl 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])[H] 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
- 150000002148 esters Chemical class 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002960 margaryl 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])[H] 0.000 description 4
- 125000001421 myristyl 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])[H] 0.000 description 4
- 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 4
- 125000002958 pentadecyl 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])[H] 0.000 description 4
- 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 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 125000006178 methyl benzyl group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000000567 combustion gas Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 2
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HAIUDCAMWHQJSW-UHFFFAOYSA-N 1-n-propylbutyl Chemical group [CH2+]CC[CH]CC[CH2-] HAIUDCAMWHQJSW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical compound [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- XFJHAKDKUQBNDB-UHFFFAOYSA-N [5-(dithiane-4-carbonyl)-1,3,4-thiadiazol-2-yl]-(dithian-4-yl)methanone Chemical compound N=1N=C(C(=O)C2CSSCC2)SC=1C(=O)C1CCSSC1 XFJHAKDKUQBNDB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 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
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- OMAAXMJMHFXYFY-UHFFFAOYSA-L calcium trioxidophosphanium Chemical compound [Ca+2].[O-]P([O-])=O OMAAXMJMHFXYFY-UHFFFAOYSA-L 0.000 description 1
- AVVIDTZRJBSXML-UHFFFAOYSA-L calcium;2-carboxyphenolate;dihydrate Chemical compound O.O.[Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O AVVIDTZRJBSXML-UHFFFAOYSA-L 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940072082 magnesium salicylate Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 150000002815 nickel Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 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
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
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Definitions
- the present invention relates to a novel lubricating oil composition. More specifically, the present invention is concerned with a lubricating oil composition, which has excellent friction-reducing properties and high antiwear properties, is free from deterioration even in an air atmosphere containing NOx gas, retains friction-reducing properties over an extended period of time and accordingly, which is usable as a lubricating oil for internal combustion engines, automatic transmissions, dampers or power steering systems and makes it possible to achieve high gas mileage especially as a lubricating oil for internal combustion engines.
- Lubricating oils are used in internal combustion engines and in driving units and gears such as automatic transmissions, dampers and power steering systems to ensure smooth operation thereof.
- a lubricating oil for an internal combustion engine serves to cool the inside of the engine, to clean and disperse combustion products and to protect the engine from rusting and corrosion in addition to lubrication of various sliding portions such as piston rings and their associated cylinder liner, bearings for a crankshaft and a connecting rod, and a valve-operating mechanism including cams and valve lifters.
- a lubricating oil for internal combustion engines is required to meet diverse property requirements. Moreover, keeping step with the trend toward internal combustion engines of higher performance such as those achieving higher gas mileage and higher power output and permitting more severe operating conditions in recent years, there is an increasing demand for lubricating oils of still higher performance. As a basic function of a lubricating oil for internal combustion engines, it is especially important to assure smooth operation of the engines while protecting them from wearing and seizure under all condition. Lubricated portions of an engine mostly remain under fluid lubrication conditions but around the top and bottom dead centers of its valve-operating system or a piston, they tend to come under boundary lubrication conditions.
- combustion gas partly leaks between a cylinder and its piston and penetrates as blowby gas into a crank case.
- NOx gas is contained at a considerably high level in combustion gas. In addition to oxygen contained in the blowby gas, this NOx gas also deteriorates the lubricating oil for the internal combustion engine. Due to the move toward internal combustion engines of higher performance in recent years, the concentration of NOx gas in a crank case tends to increase.
- a variety of additives are incorporated in a lubricating oil for internal combustion engines, including, for example, an antiwear agent, a metallic detergent, a friction modifier, a nonash dispersant and an antioxidant.
- a friction modifier is therefore added to a lubricating oil as a measure for reducing the friction loss and increasing the gas mileage.
- Usable examples of the friction modifier generally include organic molybdenum compounds, fatty esters and alkylamines. These friction modifiers show their effects in an early stage after the initiation of their use but when subjected to oxidative deterioration by oxygen in the air, their effects are lost. A marked reduction in their effects is observed especially in the presence of NOx gas.
- An object of the present invention is therefore to provide a lubricating oil composition which can retain friction-reducing effects for engines over an extended period of time without being adversely affected by NOx gas and possesses and exhibits both excellent friction-reducing properties and high antiwear properties.
- the present inventors have discovered a lubricating oil composition with a zinc di (primary alkyl) dithiophosphate and a zinc di (secondary alkyl) dithiophosphate, a specific sulfur compound, and an oxymolybdenum sulfide dithiocarbamate or an oxymolybdenum sulfide dithiophosphate added in specific proportions to a lubricating base oil which has been found to attain the above object, leading to the completion of the present invention.
- the present invention therefore provides a lubricating oil composition
- a lubricating oil composition comprising a major portion of lubricating base oil and a minor portion of the following components:
- the weight ratio of the phosphorus content of said zinc di (primary alkyl) dithiophosphate to that of said zinc di (secondary alkyl) dithiophosphate in the above-described lubricating oil composition can range from 25:75 to 80:20.
- R 1 , R 2 , R 3 and R 4 in the formula [1] can individually represent primary alkyl groups having 8 to 13 carbon atoms and R 5 , R 6 , R 7 and R 8 in the formula [2] can individually represent secondary alkyl groups having 4 to 6 carbon atoms, as another preferred embodiment of the present invention.
- lubricating base oil employed in the lubricating oil composition according to the present invention No particular limitation is imposed on the lubricating base oil employed in the lubricating oil composition according to the present invention.
- Those commonly employed as base oils in conventional lubricating oils for example, mineral oils and synthetic oils, can be used.
- the mineral oils include raffinates obtained by solvent-refining of raw materials for lubricating oils by using an aromatic extraction solvent such as phenol or furfural; hydrogenated oils obtained by hydrogenation of raw materials for lubricating oils by using a hydrogenation catalyst such as cobalt, molybdenum or the like supported on silica-alumina as a carrier; mineral oils such as lubricating oil fractions obtained by isomerization of wax, for example, 60 neutral oil, 100 neutral oil, 150 neutral oil, 300 neutral oil, 500 neutral oil, and bright stocks.
- examples of the synthetic oils include poly- ⁇ -olefin oligomers, polybutene, alkylbenzene, polyol esters, polyglycol esters, dibasic acid esters, phosphate esters and silicone oils. These base oils can be used either singly or in combination. It is also possible to use one or more mineral oils in combination with one or more synthetic oils.
- Preferred as base oils for use in the lubricating oil composition according to the present invention are those having viscosities at 100°C in a range of from 3 to 20 mm 2 /s.
- particularly preferred are hydrogenated oil and isomerized wax oils, which contain 3 wt% or less of aromatic components, 50 ppm or less (weight basis) of sulfur and 50 ppm or less (weight basis) of nitrogen.
- the lubricating oil composition according to the present invention contains the zinc di (primary alkyl) dithiophosphate represented by the formula [1] and the zinc di (secondary alkyl) dithiophosphate represented by the formula [2].
- R 1 , R 2 , R 3 and R 4 individually represent primary alkyl groups having 1 to 20 carbon atoms, which may be the same or different.
- a primary alkyl group means an alkyl group in which two hydrogen atoms and one carbon atom are bonded to the carbon atom directly bonded to an oxygen atom or an alkyl group in which three hydrogen atoms are bonded to the carbon atom directly bonded to an oxygen atom.
- Each primary alkyl group in the formula [1] can be either linear or branched.
- Illustrative of such primary alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, and 2-ethyl hexyl.
- a zinc di (primary alkyl) dithiophosphate with primary alkyl groups having 3-12 carbon atoms as its primary alkyl groups can be used particularly preferably.
- R 5 , R 6 , R 7 and R 8 individually represent secondary alkyl group having 3 to 7 carbon atoms, which may be the same or different.
- a secondary alkyl group means an alkyl group in which one hydrogen atom and two carbon atoms are bonded to the carbon atom directly bonded to an oxygen atom.
- Such secondary alkyl groups are isopropyl, secondary butyl, 1-methylbutyl, 1-methylpentyl, 1-methylhexyl, 1-ethylpropyl, 1-ethylbutyl, 1-ethylpentyl, 1-n-propylbutyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,3-dimethylbutyl, 1,2-dimethylpentyl, 1,3-dimethylbutyl, 1,3-dimethylbutyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, 1-ethyl-2-methylpropyl, 1-ethyl-2-methylbutyl, 1-ethyl-3-methylbutyl, 1-isopropylbutyl, and 1-isopropyl-2-methylpropyl.
- the zinc di (primary alkyl) dithiophosphate represented by the formula [1] and the zinc di (secondary alkyl) dithiophosphate represented by the formula [2] are added to the lubricating base oil in such amounts that the weight ratio of the phosphorus content of the former dithiophosphate to that of the latter dithiophosphate ranges from 20:80 to 80:20, preferably from 25:75 to 80:20, more preferably from 30:70 to 70:30.
- the addition of the zinc di (primary alkyl) dithiophosphate and the zinc di (secondary alkyl) dithiophosphate at a weight ratio in phosphorous content of from 20:80 to 80:20 makes it possible to improve the friction-reducing properties without reducing the antiwear properties.
- the weight ratio of the phosphorus content of the zinc di (primary alkyl) dithiophosphate to that of the zinc di (secondary alkyl) dithiophosphate is smaller than 20:80, that is, the proportion of the zinc di (primary alkyl) dithiophosphate is unduly small relative to that of the zinc di (secondary alkyl) dithiophosphate, there is the potential problem that the resulting lubricating oil composition may not be provided with sufficient friction-reducing properties.
- the weight ratio of the phosphorus content of the zinc di (primary alkyl) dithiophosphate to that of the zinc di (secondary alkyl) dithiophosphate exceeds 80:20, that is, the proportion of the zinc di (secondary alkyl) dithiophosphate is unduly small relative to that of the zinc di (primary alkyl) dithiophosphate, there is the potential problem that the resulting lubricating oil composition may be provided with lowered antiwear properties.
- the zinc di (primary alkyl) dithiophosphate and the zinc di (secondary alkyl) dithiophosphate are incorporated in amounts so that the amount of phosphorus derived therefrom is in the range 0.07 to 0.15 wt%, preferably 0.08 to 0.10 wt% based on the total weight of the lubricating oil composition.
- An amount of phosphorus derived from the zinc di (primary alkyl) dithiophosphate and the zinc di (secondary alkyl) dithiophosphate smaller than 0.07 wt% of the total weight of the lubricating oil composition may disadvantageously lead to insufficient antiwear properties.
- an amount of phosphorus derived from the zinc di (primary alkyl) dithiophosphate and the zinc di(secondary alkyl) dithiophosphate greater than 0.15 wt% of the total weight of the lubricating oil composition is not expected to bring about an additional improvement in effects in proportion to the increase in the amount of phosphorus.
- the lubricating oil composition according to the present invention further contains one or more sulfur compounds selected from the group consisting of zinc dialkyl dithiocarbamates, copper dialkyl dithiocarbamates or nickel dialkyl dithiocarbamates in which each alkyl group has 2 to 18 carbon atoms, tetraalkylthiuram disulfides in which each alkyl group has 2 to 18 carbon atoms, disulfides containing one or more alkyl groups having 2 to 18 carbon atoms, disulfides containing one or more aryl groups having 6 to 18 carbon atoms or one or more alkylaryl or arylalkyl groups having 7 to 18 carbon atoms, thiadiazole compounds having one or more sulfur-containing substituent groups and 3 to 24 carbon atoms, olefin sulfides, sulfurized fish oil and sulfurized whale oil.
- one or more sulfur compounds selected from the group consisting of zinc dialkyl dithiocarbamates, copper dialkyl dithiocarbamates or
- M represents a zinc atom, a copper atom or a nickel atom
- R 17 , R 18 , R 19 and R 20 individually represent alkyl groups having 2 to 18 carbon atoms, which may be the same or different.
- the alkyl groups which are represented by R 17 , R 18 , R 19 and R 20 and have 2 to 18 carbon atoms can either be linear or branched.
- R 21 , R 22 , R 23 and R 24 individually represent alkyl groups having 2 to 18 carbon atoms, which may be the same or different.
- the alkyl groups which are represented by R 21 , R 22 , R 23 and R 24 and have 2 to 18 carbon atoms can be either linear or branched.
- Disulfides usable for addition to the lubricating oil composition according to the present invention include compounds represented by the following formula [7]: R 25 -S-S-R 26 [7]
- R 25 and R 26 individually represent alkyl groups having 2 to 18 carbon atoms, aryl groups having 6 to 18 carbon atoms, or alkylaryl or arylalkyl groups having 7 to 18 carbon atoms, preferably alkyl groups having 6 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms, or alkylaryl or arylalkyl groups having 7 to 12 carbon atoms, which may be either the same or different.
- the alkyl groups which are represented by R 25 and R 26 and have 2 to 18 carbon atoms can be either linear or branched.
- examples of the aryl groups having 6 to 18 carbon atoms and the alkylaryl and arylalkyl groups having 7 to 18 carbon atoms, which are represented by R 25 and R 26 include phenyl, naphthyl, benzyl, phenethyl, methylbenzyl, and diphenylmethyl.
- dibenzyl disulfide can be used as a particularly preferred disulfide.
- Illustrative examples of the monovalent groups which are represented by R 27 and R 28 in the formula [8] and contain one or more sulfur atoms include 5-thianonyl, 2,5-dithiahexyl, 3,4-dithiahexyl, 4,5-dithiahexyl, 3,4,5-trithiaheptyl, 3,4,5,6-tetrathiaoctyl, 5-thia-2-heptenyl, 4-thiacyclohexyl, 1,4-dithianaphthyl, 5-(methylthio) octyl, 4-(ethylthio)-2-pentenyl, 4-(methylthio) cyclohexyl, 4-mercaptophenyl, 4-(methylthio) phenyl, and 4-(hexylthio) benzyl.
- groups containing 2 to 4 sulfur atoms successively bonded together in their chains such as a 3,4-dithiahexyl group represented by the following formula [9], a 4,5-dithiahexyl group represented by the following formula [10], a 3,4,5-trithiaheptyl group represented by the following formula [11] and a 3,4,5,6-tetrathiaoctyl group represented by the following formula [12]: CH 3 CH 2 -S-S-CH 2 CH 2 - [9] CH 3 -S-S-CH 2 CH 2 CH 2 - [10] CH 3 CH 2 -S-S-S-CH 2 CH 2 - [11] CH 3 CH 2 -S-S-S-S-CH 2 CH 2 - [12]
- olefin sulfides polysulfides obtained by subjecting polymers of isobutylene and the like to sulfurization treatment and having sulfur contents of from 25 to 40 wt%.
- sulfurized fish oil and sulfurized whale oil those obtained by similarly subjecting fish oil and whale oil to sulfurization treatment can be exemplified.
- the dialkyl dithiocarbamates represented by the formula [5], the tetraalkylthiuram disulfides represented by the formula [6], the disulfides represented by the formula [7], the thiadiazole compounds represented by the formula [8] and the olefin sulfides, the sulfurized fish oil and the sulfurized whale oil can be used either singly or in combination.
- One or more of these sulfur compounds are added in such amount(s) that the amount of sulfur derived from the sulfur compound(s) ranges from 300 to 1,200 ppm (weight basis) of the total weight of the lubricating oil composition.
- the sulfur compound(s) are added in such an amount that the amount of sulfur derived from the sulfur compound(s) is smaller than 300 ppm (weight basis) or greater than 1,200 ppm (weight basis), there is the potential problem that the effect of retaining friction-reducing properties over an extended period of time may not be exhibited sufficiently.
- the oxymolybdenum sulfide dithiocarbamate represented by the following formula [3] or the oxymolybdenum sulfide dithiophosphate represented by the following formula [4] is incorporated:
- R 9 , R 10 , R 11 and R 12 individually represent hydrocarbon groups having 1 to 30 carbon atoms, and Xs represent oxygen or sulfur atoms.
- the hydrocarbon groups represented by R 9 , R 10 , R 11 and R 12 may all be the same or different.
- all Xs can be sulfur atoms or oxygen atoms, or some X(s) can be sulfur atom(s) and the remaining X(s) can be oxygen atom(s).
- Examples of the hydrocarbon groups represented by R 9 , R 10 , R 11 and R 12 include alkyl groups having 1 to 30 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, cycloalkyl groups having 5 to 30 carbon atoms, aryl groups having 6 to 30 carbon atoms, and alkylaryl and arylalkyl groups having 7 to 30 carbon atoms.
- hydrocarbon groups having 1 to 30 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, cyclohexyl, dimethylcyclohexyl, ethylcyclohexyl, butylcyclohexyl, heptylcyclohexyl, phenyl, benzyl, dimethylphenyl, methylbenzyl, phenethyl, naphthyl, and dimethylnaphthyl.
- R 9 , R 10 , R 11 and R 12 in the formula [3] are alkyl groups having 8 to 13 carbon atoms
- R 13 , R 14 , R 15 and R 16 individually represent hydrocarbon groups having 1 to 30 carbon atoms, and Xs represent oxygen or sulfur atoms.
- the hydrocarbon groups represented by R 13 , R 14 , R 15 and R 16 may all be the same or different.
- all Xs can be sulfur atoms or oxygen atoms, or some X(s) can be sulfur atom(s) and the remaining X(s) can be oxygen atom(s).
- Examples of the hydrocarbon groups represented by R 9 , R 10 , R 11 and R 12 include alkyl groups having 1 to 30 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, cycloalkyl groups having 5 to 30 carbon atoms, aryl groups having 6 to 30 carbon atoms, and alkylaryl and arylalkyl groups having 7 to 30 carbon atoms.
- hydrocarbon groups having having 1 to 30 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, cyclohexyl, dimethylcyclohexyl, ethylcyclohexyl, methylcyclo-hexylmethyl, cyclohexylethyl, propylcyclohexyl, butylcyclohexyl, heptylcyclohexyl, phenyl, benzyl, dimethylphenyl, methylbenzyl, phenethyl, naphthyl, and dimethylnaphthyl.
- such oxymolybdenum sulfide dithiocarbamates or oxymolybdenum sulfide dithiophosphates can be used either singly or in combination. Further, the oxymolybdenum sulfide dithiocarbamate or oxymolybdenum sulfide dithiophosphate is added in an amount such that the amount of molybdenum derived from the oxmolybdenum sulfide dithiocarbamate or oxymolybdenum sulfide dithiophosphate ranges from 200 to 2,000 ppm (weight basis), preferably from 300 to 800 ppm (weight basis).
- the amount of the oxymolybdenum sulfide dithiocarbamate or oxymolybdenum sulfide dithiophosphate is so small that the amount of molybdenum derived from the oxymolybdenum sulfide dithiocarbamate or oxymolybdenum sulfide dithiophosphate is lower than 200 ppm (weight basis) of the total weight of the lubricating oil composition, there is the potential problem that the improving effect of friction-reducing properties may not be fully exhibited.
- additives which have heretofore been commonly employed in lubricating oils, to extents not impairing the object of the present invention.
- additives include other antiwear agents, metallic detergents, other friction modifiers, nonash dispersants, antioxidants, viscosity index improvers, pour-point depressants, anti-foaming agents, rust preventives, and corrosion inhibitors.
- Examples of the other friction modifiers include partial esters of polyhydric alcohols, amines, amides, and sulfate esters.
- metallic detergents examples include calcium salicylate, magnesium salicylate, calcium sulfonate, magnesium sulfonate, barium sulfonate, calcium phosphonate, and barium phenate. These metallic detergents can be added generally in a proportion of from 0.1 to 5.0 wt%.
- antiwear agents examples include metal thiophosphates, sulfur compounds, phosphate esters, and phosphite esters. These antiwear agents can be added generally in a proportion of from 0.05 to 5.0 wt%.
- nonash dispersants examples include those of the succinimide, succinamide, benzylamine and ester types. These nonash dispersants can be added generally in a proportion of from 0.5 to 7.0 wt%.
- antioxidants examples include phenolic antioxidants such as 2,6-di-t-butyl-4-methylphenol and 4,4'-methylenebis (2,6-di-t-butylphenol). These antioxidants can be added generally in a proportion of from 0.05 to 4.0 wt%.
- viscosity index improvers examples include those of the polymethacrylate, polyisobutylene, ethylene-propylene copolymer and hydrogenated styrene-butadiene copolymer types. These viscosity index improvers can be added generally in a proportion of from 0.5 to 35 wt%.
- pour-point depressants examples include poly (alkyl methacrylate), chlorinated paraffin-naphthalene condensates, and alkylated polystyrenes.
- anti-foaming agents examples include dimethyl polysiloxane and polyacrylic acid.
- rust preventives examples include fatty acids, partial esters of alkenylsuccinic acids, fatty acid soaps, alkylsufonate salts, polyhydric alcohol esters of fatty acids, fatty acid amines, paraffin oxides, and alkyl polyoxyethylene ethers.
- corrosion inhibitors examples include benzotriazole and benzoimidazole.
- each average cam wear was measured in accordance with ASTM RR:D-2:1266.
- the coefficient of friction of each lubricating oil composition was measured using a reciprocating sliding friction tester ("SRV Friction Tester") under the following conditions: frequency: 50 Hz, amplitude: 3 mm, load: 25 N, temperature: 80°C, and testing time: 25 minutes.
- Each oxidation test by NOx-containing air was conducted on 150 ml of the corresponding test oil under the following conditions: temperature: 130°C, nitrogen oxides (NOx) concentration: 1 vol%, flow rate: 2 l/hour, and testing time: 8 hours.
- a lubricating oil composition was prepared by adding, to a paraffinic mineral oil having a viscosity of 4.0 mm 2 /s at 100°C, calcium sulfonate as a metallic detergent in a proportion of 2.0 wt%, succinimide as a nonash dispersant in a proportion of 5.0 wt%, hindered phenol as an antioxidant in a proportion of 1.0 wt%, poly (alkyl methacrylate) as a viscosity index improver in a proportion of 5.0 wt%, zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate in proportions to give a weight ratio in phosphorus content of 80:20 and a phosphorus content of 0.10 wt%, dibenzyl disulfide in a proportion to give a sulfur content of 500 ppm (weight basis), and oxymolybdenum-N, N-dioctyl sul
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 75:25 and a phosphorus content of 0.10 wt%.
- An average cam wear when this lubricating oil composition was used was 5.5 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation and was still 0.11 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 70:30 and a phosphorous content of 0.10 wt%.
- An average cam wear when this lubricating oil composition was used was 4.6 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation and was still 0.11 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 50:50 and a phosphorus content of 0.10 wt%.
- An average cam wear when this lubricating oil composition was used was 3.6 mil.
- the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation but was 0.12 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 30:70 and a phosphorus content of 0.10 wt%.
- An average cam wear when this lubricating oil composition was used was 2.5 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation but was 0.13 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl diothiophosphate were added to give a weight ratio in phosphorus content of 25:75 and a phosphorus content of 0.10 wt%.
- An average cam wear when this lubricating oil composition was used was 2.2 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation but was 0.13 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 20:80 and a phosphorus content of 0.10 wt%.
- An average cam wear when this lubricating oil composition was used was 2.0 mil. Further, the coefficient of friction of the lubricating oil composition was 0.12 immediately after its preparation but was 0.14 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 4 except that a poly- ⁇ -olefin having a viscosity of 4.0 mm 2 /s at 100°C was used as a lubricating base oil.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 50:50 and a phosphorus content of 0.08 wt%.
- An average cam wear when this lubricating oil composition was used was 4.5 mil.
- the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation but was 0.13 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 50:50 and a phosphorus content of 0.10 wt% and that dibenzyl disulfide was added to give a sulfur content of 300 ppm (weight basis).
- An average cam wear when this lubricating oil composition was used was 4.2 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation but was 0.13 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 50:50 and a phosphorus content of 0.10 wt% and that dibenzyl disulfide was added to give a sulfur content of 1,200 ppm (weight basis).
- An average cam wear when this lubricating oil composition was used was 3.5 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation but was 0.14 after the oxidation test.
- a lubricating oil composition was prepared with the same formula as that of Example 1 except that zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 30:70 and a phosphorus content of 0.10 wt% and that in lieu of dibenzyl disulfide, 2,5-di(4,5-dithianoyl)-1,3,4-thiadiazole was added to give a sulfur content of 500 ppm (weight basis).
- An average cam wear when this lubricating oil composition was used was 2.8 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation but was 0.13 after the oxidation test.
- a lubricating oil composition was prepared by adding, to a paraffinic mineral oil having a viscosity of 4.0 mm 2 /s at 100°C, calcium sulfonate as a metallic detergent in a proportion of 2.0 wt%, succinimide as a nonash dispersant in a proportion of 5.0 wt%, hindered phenol as an antioxidant in a proportion of 1.0 wt%, poly(alkyl methacrylate) as a viscosity index improver in a proportion of 5.0 wt%, zinc di-2-ethylhexyl dithiophosphate in a proportion to give a phosphorus content of 0.10 wt%, dibenzyl disulfide in a proportion to give a sulfur content of 500 ppm (weight basis), and oxymolybdenum-N, N-dioctyl sulfide dithiocarbamate to give a molybdenum content of 500 ppm (weight basis).
- a lubricating oil composition was prepared with the same formula as that of Comparative Example 1 except that instead of zinc di-2-ethylhexyl dithiophosphate, zinc di-2-ethylhexyl dithiophosphate and zinc di-1-methylbutyl dithiophosphate were added to give a weight ratio in phosphorus content of 90:10 and a phosphorus content of 0.10 wt%.
- An average cam wear when this lubricating oil composition was used was 10.5 mil. Further, the coefficient of friction of the lubricating oil composition was 0.11 immediately after its preparation and was still 0.11 after the oxidation test.
- Lubricating oil compositions of the formulas shown in Table 2 were prepared, and their average cam abrasion losses, their coefficients of friction immediately after the preparation and their coefficients of friction after their oxidation tests were measured.
- the lubricating oil composition of Comparative Example 1 which was added with the zinc di (primary alkyl) dithiophosphonate but was not added with any zinc di (secondary alkyl) dithiophosphate, was greater in average cam abrasion loss and hence inferior in antiwear properties compared with the lubricating oil composition of Example 1 although both the lubricating oil compositions contained the same amount of phosphorus derived from the zinc dialkyl dithiophosphate(s).
- the lubricating oil composition of Comparative Example 2 which contained the zinc di (primary alkyl) dithiophosphate in the larger proportion and the zinc di (secondary alkyl) dithiophosphate in the smaller proportion, was also poor in antiwear properties.
- the lubricating oil composition of Comparative Example 3 which contained the zinc di (primary alkyl) dithiophosphate in the smaller proportion and the zinc di (secondary alkyl) dithiophosphate in the larger proportion, was smaller in average cam abrasion loss and hence had good antiwear properties, but was larger in the coefficient of friction after the oxidation test and was hence inferior in oxidation resistance.
- the lubricating oil composition of Comparative Example 4 which was not added with any zinc di (primary alkyl) dithiophosphate but was added with the zinc di (secondary alkyl) dithiophosphate alone, was still better in antiwear properties, but had the high coefficient of friction even immediately after its preparation and was hence low in friction-reducing properties.
- the lubricating oil composition of Comparative Example 5 in which the zinc di (primary alkyl) dithiophosphate and the zinc di (secondary alkyl) dithiophosphate were used to give the weight ratio in phosphorus content of 50:50 but they were added in small amounts and the amount of phosphorus derived from the zinc di (alkyl) dithiophosphates was 0.06 ppm (weight basis), was inferior in antiwear properties and also poor in oxidation resistance.
- the lubricating oil composition of Comparative Example 8 in which no oxymolybdenum sulfide thiocarbamate was added at all, had a high coefficient of friction even immediately after its preparation and was hence inferior in friction-reducing properties.
- the lubricating oil composition according to the present invention has excellent antiwear properties and even at elevated temperatures and in the presence of nitrogen oxides, exhibits high oxidation resistance and retains good friction-reducing properties, so that it can be suitably used as a lubricating oil for internal combustion engines.
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28933895A JP3556355B2 (ja) | 1995-10-11 | 1995-10-11 | 潤滑油組成物 |
| JP289338/95 | 1995-10-11 | ||
| JP28933895 | 1995-10-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0768366A1 true EP0768366A1 (fr) | 1997-04-16 |
| EP0768366B1 EP0768366B1 (fr) | 2001-06-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96307382A Expired - Lifetime EP0768366B1 (fr) | 1995-10-11 | 1996-10-10 | Composition d'huile lubrifiante |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0768366B1 (fr) |
| JP (1) | JP3556355B2 (fr) |
| AU (1) | AU6812696A (fr) |
| CA (1) | CA2185716A1 (fr) |
| DE (1) | DE69613304T2 (fr) |
| ES (1) | ES2159692T3 (fr) |
| SG (1) | SG63672A1 (fr) |
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| EP2078725A1 (fr) * | 2006-10-30 | 2009-07-15 | Adeka Corporation | Composé de phosphore et molybdène, procédé de production correspondant, additif pour lubrifiant contenant ce composé, et composition de lubrifiant |
| EP2248877A1 (fr) * | 2009-05-01 | 2010-11-10 | Afton Chemical Corporation | Composition de lubrifiant contenant zinc dialkyl dithiophosphate des alcools primaires ou secondaires |
| WO2010142724A1 (fr) * | 2009-06-10 | 2010-12-16 | Infineum International Limited | Composition d'huile lubrifiante |
| US7884059B2 (en) | 2004-10-20 | 2011-02-08 | Afton Chemical Corporation | Oil-soluble molybdenum derivatives derived from hydroxyethyl-substituted Mannich bases |
| RU2442820C1 (ru) * | 2010-12-16 | 2012-02-20 | Федеральное автономное учреждение "25 Государственный научно-исследовательский институт химмотологии Министерства обороны Российской Федерации" | Полифункциональная присадка к моторным маслам |
| US8211840B2 (en) | 2008-12-09 | 2012-07-03 | Afton Chemical Corporation | Additives and lubricant formulations for improved antiwear properties |
| WO2013083791A1 (fr) * | 2011-12-07 | 2013-06-13 | Shell Internationale Research Maatschappij B.V. | Composition d'huile lubrifiante |
| EP2949738A1 (fr) * | 2014-05-30 | 2015-12-02 | Afton Chemical Corporation | Composition d'huile lubrifiante et additif associé présentant des propriétés améliorées de résistance à l'usure |
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| US9593291B2 (en) | 2012-03-16 | 2017-03-14 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition, and sliding mechanism using lubricating oil composition |
| WO2021021888A1 (fr) * | 2019-07-29 | 2021-02-04 | Ecolab USA, Inc. | Complexes de molybdène solubles dans l'huile servant d'inhibiteurs d'encrassement à haute température |
| WO2021021891A1 (fr) * | 2019-07-29 | 2021-02-04 | Ecolab Usa Inc. | Complexes de molybdène solubles dans l'huile pour inhiber la corrosion à haute température et utilisations associées dans des raffineries de pétrole |
| WO2022026434A1 (fr) * | 2020-07-29 | 2022-02-03 | Ecolab Usa Inc. | Complexes de molybdène solubles dans l'huile exempts de phophore pour inhiber la corrosion par l'acide naphténique à haute température |
| US11999915B2 (en) | 2020-07-29 | 2024-06-04 | Ecolab Usa Inc. | Phosphorous-free oil soluble molybdenum complexes as high temperature fouling inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60020044T3 (de) * | 1999-09-21 | 2008-12-18 | Infineum International Ltd., Abingdon | Multigrad Schmiermittelzusammensetzungen für Motorgehäuse |
| SG87171A1 (en) * | 1999-09-21 | 2002-03-19 | Infineum Int Ltd | Lubricating oil compositions |
| JP4643030B2 (ja) * | 2001-01-29 | 2011-03-02 | 日産自動車株式会社 | ディーゼルエンジン油組成物 |
| JP5042106B2 (ja) * | 2002-04-08 | 2012-10-03 | 株式会社豊田中央研究所 | 自動変速機用潤滑油組成物 |
| KR20110111308A (ko) * | 2009-01-20 | 2011-10-10 | 더루우브리졸코오포레이션 | 마모 성질이 개량된 유압 조성물 |
| JP5600677B2 (ja) * | 2009-07-14 | 2014-10-01 | Ｊｘ日鉱日石エネルギー株式会社 | 省燃費型エンジン油組成物 |
| JP5658066B2 (ja) | 2011-03-23 | 2015-01-21 | 昭和シェル石油株式会社 | 潤滑油組成物 |
| WO2016181863A1 (fr) * | 2015-05-08 | 2016-11-17 | Ｊｘエネルギー株式会社 | Composition d'huile lubrifiante |
| US12110468B1 (en) | 2023-03-22 | 2024-10-08 | Afton Chemical Corporation | Antiwear systems for improved wear in medium and/or heavy duty diesel engines |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7884059B2 (en) | 2004-10-20 | 2011-02-08 | Afton Chemical Corporation | Oil-soluble molybdenum derivatives derived from hydroxyethyl-substituted Mannich bases |
| US7960321B2 (en) | 2004-10-20 | 2011-06-14 | Afton Chemical Corporation | Oil-soluble molybdenum derivatives derived from hydroxyethyl-substituted Mannich bases |
| KR101421310B1 (ko) * | 2006-09-04 | 2014-07-18 | 이데미쓰 고산 가부시키가이샤 | 내연 기관용 윤활유 조성물 |
| EP2060619A1 (fr) * | 2006-09-04 | 2009-05-20 | Idemitsu Kosan Co., Ltd. | Composition lubrifiante pour un moteur à combustion interne |
| EP2060619A4 (fr) * | 2006-09-04 | 2011-08-03 | Idemitsu Kosan Co | Composition lubrifiante pour un moteur à combustion interne |
| US8309499B2 (en) | 2006-09-04 | 2012-11-13 | Idemitsu Kosan Co., Ltd. | Lubricant composition for internal combustion engine |
| EP2078725A1 (fr) * | 2006-10-30 | 2009-07-15 | Adeka Corporation | Composé de phosphore et molybdène, procédé de production correspondant, additif pour lubrifiant contenant ce composé, et composition de lubrifiant |
| EP2078725A4 (fr) * | 2006-10-30 | 2011-09-21 | Adeka Corp | Composé de phosphore et molybdène, procédé de production correspondant, additif pour lubrifiant contenant ce composé, et composition de lubrifiant |
| WO2008061079A2 (fr) * | 2006-11-14 | 2008-05-22 | Honeywell International Inc. | Agents stabilisants de fluorocarbure |
| WO2008061079A3 (fr) * | 2006-11-14 | 2008-10-09 | Honeywell Int Inc | Agents stabilisants de fluorocarbure |
| US8211840B2 (en) | 2008-12-09 | 2012-07-03 | Afton Chemical Corporation | Additives and lubricant formulations for improved antiwear properties |
| EP2248877A1 (fr) * | 2009-05-01 | 2010-11-10 | Afton Chemical Corporation | Composition de lubrifiant contenant zinc dialkyl dithiophosphate des alcools primaires ou secondaires |
| US8084403B2 (en) | 2009-05-01 | 2011-12-27 | Afton Chemical Corporation | Lubricant formulations and methods |
| WO2010142724A1 (fr) * | 2009-06-10 | 2010-12-16 | Infineum International Limited | Composition d'huile lubrifiante |
| CN102459540A (zh) * | 2009-06-10 | 2012-05-16 | 英菲诺姆国际有限公司 | 润滑油组合物 |
| RU2442820C1 (ru) * | 2010-12-16 | 2012-02-20 | Федеральное автономное учреждение "25 Государственный научно-исследовательский институт химмотологии Министерства обороны Российской Федерации" | Полифункциональная присадка к моторным маслам |
| WO2013083791A1 (fr) * | 2011-12-07 | 2013-06-13 | Shell Internationale Research Maatschappij B.V. | Composition d'huile lubrifiante |
| US9580666B2 (en) | 2011-12-07 | 2017-02-28 | Shell Oil Company | Lubricating oil composition |
| US9593291B2 (en) | 2012-03-16 | 2017-03-14 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition, and sliding mechanism using lubricating oil composition |
| EP2949738A1 (fr) * | 2014-05-30 | 2015-12-02 | Afton Chemical Corporation | Composition d'huile lubrifiante et additif associé présentant des propriétés améliorées de résistance à l'usure |
| US9574158B2 (en) | 2014-05-30 | 2017-02-21 | Afton Chemical Corporation | Lubricating oil composition and additive therefor having improved wear properties |
| CN105567380B (zh) * | 2014-06-06 | 2018-05-04 | 北京雅士科莱恩石油化工有限公司 | 一种润滑油 |
| CN105567380A (zh) * | 2014-06-06 | 2016-05-11 | 北京雅士科莱恩石油化工有限公司 | 一种润滑油 |
| WO2021021888A1 (fr) * | 2019-07-29 | 2021-02-04 | Ecolab USA, Inc. | Complexes de molybdène solubles dans l'huile servant d'inhibiteurs d'encrassement à haute température |
| WO2021021891A1 (fr) * | 2019-07-29 | 2021-02-04 | Ecolab Usa Inc. | Complexes de molybdène solubles dans l'huile pour inhiber la corrosion à haute température et utilisations associées dans des raffineries de pétrole |
| US20210032528A1 (en) * | 2019-07-29 | 2021-02-04 | Ecolab Usa Inc. | Oil soluble molybdenum complexes as high temperature fouling inhibitors |
| US11697756B2 (en) * | 2019-07-29 | 2023-07-11 | Ecolab Usa Inc. | Oil soluble molybdenum complexes as high temperature fouling inhibitors |
| US11767596B2 (en) | 2019-07-29 | 2023-09-26 | Ecolab Usa Inc. | Oil soluble molybdenum complexes for inhibiting high temperature corrosion and related applications in petroleum refineries |
| WO2022026434A1 (fr) * | 2020-07-29 | 2022-02-03 | Ecolab Usa Inc. | Complexes de molybdène solubles dans l'huile exempts de phophore pour inhiber la corrosion par l'acide naphténique à haute température |
| US20220033725A1 (en) * | 2020-07-29 | 2022-02-03 | Ecolab Usa Inc. | Phosphorous-free oil soluble molybdenum complexes for high temperature naphthenic acid corrosion inhibition |
| US11999915B2 (en) | 2020-07-29 | 2024-06-04 | Ecolab Usa Inc. | Phosphorous-free oil soluble molybdenum complexes as high temperature fouling inhibitors |
| US12006483B2 (en) | 2020-07-29 | 2024-06-11 | Ecolab Usa Inc. | Phosphorous-free oil soluble molybdenum complexes for high temperature naphthenic acid corrosion inhibition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0768366B1 (fr) | 2001-06-13 |
| JP3556355B2 (ja) | 2004-08-18 |
| DE69613304T2 (de) | 2001-10-31 |
| ES2159692T3 (es) | 2001-10-16 |
| SG63672A1 (en) | 1999-03-30 |
| CA2185716A1 (fr) | 1997-04-12 |
| DE69613304D1 (de) | 2001-07-19 |
| JPH09104888A (ja) | 1997-04-22 |
| AU6812696A (en) | 1997-04-17 |
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