CA2195475A1 - Lubricants with sustained fuel economy performance - Google Patents
Lubricants with sustained fuel economy performanceInfo
- Publication number
- CA2195475A1 CA2195475A1 CA002195475A CA2195475A CA2195475A1 CA 2195475 A1 CA2195475 A1 CA 2195475A1 CA 002195475 A CA002195475 A CA 002195475A CA 2195475 A CA2195475 A CA 2195475A CA 2195475 A1 CA2195475 A1 CA 2195475A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- group
- carbon atoms
- sulfide
- content
- 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.)
- Abandoned
Links
- 239000000314 lubricant Substances 0.000 title claims abstract description 70
- 239000000446 fuel Substances 0.000 title description 6
- 230000002459 sustained effect Effects 0.000 title description 2
- 229910052796 boron Inorganic materials 0.000 claims abstract description 43
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052751 metal Inorganic materials 0.000 claims abstract description 40
- 239000002184 metal Substances 0.000 claims abstract description 40
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 36
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 31
- 239000011701 zinc Substances 0.000 claims abstract description 31
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
- 150000003464 sulfur compounds Chemical class 0.000 claims abstract description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000011593 sulfur Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000000654 additive Substances 0.000 claims abstract description 15
- 239000003599 detergent Substances 0.000 claims abstract description 15
- 239000002199 base oil Substances 0.000 claims abstract description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 7
- 239000011733 molybdenum Substances 0.000 claims abstract description 7
- 230000000996 additive effect Effects 0.000 claims abstract description 6
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims abstract 7
- 239000012990 dithiocarbamate Substances 0.000 claims abstract 7
- 239000002270 dispersing agent Substances 0.000 claims abstract 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 32
- -1 olefin sulfide Chemical class 0.000 claims description 31
- 239000003921 oil Substances 0.000 claims description 30
- 235000019198 oils Nutrition 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229960002317 succinimide Drugs 0.000 claims description 16
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 7
- 235000021323 fish oil Nutrition 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- 239000010698 whale oil Substances 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 claims description 5
- 230000001050 lubricating effect Effects 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229940072082 magnesium salicylate Drugs 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229960005069 calcium Drugs 0.000 claims description 3
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 claims 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 39
- 238000002485 combustion reaction Methods 0.000 abstract description 9
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 238000005299 abrasion Methods 0.000 abstract description 3
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 7
- 239000004327 boric acid Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000001639 boron compounds Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 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 5
- 239000000463 material Substances 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 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 5
- 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 5
- 229920002367 Polyisobutene Polymers 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 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 4
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([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
- 150000002500 ions Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 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
- 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 4
- 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 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 230000003405 preventing effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 4
- 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 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000005885 boration reaction Methods 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 150000003752 zinc compounds Chemical class 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000002518 antifoaming agent 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
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- 229910052810 boron oxide Inorganic materials 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000003949 imides Chemical class 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
- 238000005461 lubrication Methods 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000002829 nitrogen Chemical class 0.000 description 2
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- 150000002989 phenols Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 239000004034 viscosity adjusting agent Substances 0.000 description 2
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- 125000003368 amide group Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
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- 150000007942 carboxylates Chemical class 0.000 description 1
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- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
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Classifications
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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- 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
- C10N2010/04—Groups 2 or 12
-
- 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
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol-fuelled engines
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
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Abstract
A lubricant composition comprising a major amount of a lubricant base oil, and a minor amount of additives comprising (A) oxymolybdenum dithiocarbamate sulphide having a specific structure, (B) zinc dialkyldithiophosphate having a specific structure, (D) an ashless dispersant, (E) a boron containing additive which may be the ashless dispersant or another additive, and (F) a metal detergent, wherein to the total weight of the composition, the molybdenum content from oxymolybdenum dithiocarbamate sulfide is at 200 to 2,000 ppm; the phosphorous content from zinc dialkyldithiophosphate is at 0.02 to 0.15 % by weight; the sulfur content from sulfur compounds is at 0.02 to 0.30 % by weight; the content of a metal detergent is at 1 to 10 % by weight; and the boron content is at 0.005 to 0.06 % by weight. The lubricant composition of the present invention has excellent low abrasion properties and can sustain good friction properties while exhibiting resistance to oxidation at higher temperatures in the presence of gaseous nitrogen oxides. The lubricant composition of the present invention is used preferably as a crankcase lubricants for internal combustion engines.
Description
~ 2195~
WO 96/06904 , , , P~
Lubricants with .c..c~ i n~ Fuel Economy r~. ru, 1, Idl .ce Field of the Invention The present invention relates to a novel lubricant c~ n.
S More ~ it relates to a lubricant c~"l,u~ i, having good low abrasion and friction ululJe~ti_3 and being capable of SIXf ' ~ I;lly 1Ow friction over a long period of bme with no cl~ iuldtiun even in an dtllluapllele COl ' 1 19 gaseous nitrogen oxides. The lubricant colll~ua~iull can be used in intemal combustion engine cldl)k~.d~lea, 10 automatic t,dna",; ,s;.~ns, wet brakes and power steering. Preferably it is used in uldllkl~d~e~ of intemal combustion enyines.
Background of the Invention Lubricants have been used to lubricate intemal combustion engines, driving systems such as automatic bd"~",;a~ion, wet brakes and 15 power steering; and gears. Lubricants for intemal combustion engines in particular have as their primary function lubricating various sliding parts such as piston rings and cylinder liners, ~lallk~l ~ bearinss and Col Ine~.~il Iy rod, and valve operabng parts. Beyond this primary function ..,d"h.ase lubricants also serve to cool the inside of engines, to clean 20 engine parts, to disperse combustion products, and further to prevent rust and conrosion.
In recent years intemal combustion engines have been modified to lower fuel consumption while i"u, edail Iy power output and -improving durability even under severe operating conditions. In consequence 25 greater demands have been placed on lubricants. In addition, c~mhufr~ gases from internal combListion engines leak from between the piston and the cylinder into the crankcase in the fomm of blow-by-gas.
These combustion gases contains higher levels of gaseous nibrogen oxides, which together with oxygen in the blow-by-gas cletel iu~ the 30 lubricants. The levels of gaseous nitrogen oxides leaking into the ~.ldllk~dse tend to increase as engine pelrul",allce demands increase.
To prevent d~.b,.iu,dLiun in an dtlllU l,uhele COIIta;~ gaseous nitrogen oxides, while retaining lubricity pe~ru~ d~lue, lubricants are blended with various additives, for example, wear ~ , .,ti.,g agents, metal salts of CONFIRM~llON COI~
WO 96/06901 r~
organic acids commonly known as d~Lelye l ~ta, ashless .I;~ adl lta, and dl ILiU~ dl ILa.
Engine lubricating parts are mostiy in a state of fluid lubrication, but vertical dead centers of valve operating systems and pistons are likely in S a state of interface (or boundary) lubncation. In such a state of interface - lubrication, wear preventing properties are generally provided by adding zinc '''liupl~a~JII. '~.
Friction modifiers are also added to the lubricants as a cou"L~:""ea~lre to decrease effficiency loss from friction and thereby 10 reduce fuel consumption. As such friction modifiers, for example, organic molybdenum compounds, fatty acid esters, alkylamines and the like, are used in general.
After intensive i"Je ':~ '' )ns under such circumstance, it has been found that friction modifiers are effective in a fresh lubricant, that is, at the 1~ initial stage of use after their addition, but friction modifiers lose their effect when they are oxidized and dl:Lt:riol ' by dtlllua~/he~ oxygen, and that the decrease of the effficacy is distinctive in the presence of gaseous nitrogen oxides. Thus, the present invention has been achieved forthe purpose of developing a lubricant .,ulllr " n which can provide 'O sustained fuel economy pe,ru""ance with the effect of de~"~dai"g friction in engines for a long period of time in the presence of gaseous nitrogen oxides.
Summary of the Invention - A lubricant has been discovered that has good lubricity and aiaLdl l~,e to dl:L~:, io,dLiol, in the presence of oxygen and gaseous nitrogen oxides. It comprises a major amount of a lubricant base oil, a b..~e~ k of lubricating viscosity, to which a minor amount of additives has been added. The additives comprise specific amounts of oxymolybdenum diilliucdlLJd~ u sulfide having specific alkyl groups, zinc ,0 dialkyl,liLhiophuayhdt~ having specific alkyl groups, one or more specific sulfur collLdillillg compounds, an ashless ~ ,ad"l and a boron ~,u, ' ,;.,9 additive which may be the ashless di~pe,ad"L. In further 21g5~,7~
WO 96/0690~ - 3 -~ .
~ ~=.
aspects of the invention a metal detergent is used. Co~ llIly, the Jelad"L and boron are added as a borated succinimide. Thus, the ~ present invention has been achieved on the basis of the finding.
The present invention is a lubricant ..c" ",ua;.ion cw"~,,iaiuy a major amount of a lubricant base oil having added thereto a minor amount of additives co"",,iai"g (A) uxy,l~ulyb i~::"um ~"'tl;U~dli dll - '~ sulfide having aikyl groups with 8 to 18 carbon atoms, (B) zinc dialky' ' '',;u,uhosyl ' having primary alkyl groups with 1 to 18 carbon atoms, (C) one or more additional peroxide deculll~Joa;,ly sulfur compounds, (D) an ashless di."J~Iadlll, and (E) a boron containing additive in an amount sufficient to provide at from 0.0û5 to 0.06 C/o by weight boron to the finished lubricant wherein to the total weight of the culll,uG~;liull, the molybdenum content from oxymolybdenum iitlliuudliJdllldL~ sulfide is at 200 to 2,000 ppm (ratio by weight); the pllu:,pholu.ls content from zinc ' 'hyWitlliuphoa~Jh. '~ is at 0.02 to 0.15 C/o by weight; and the sulfur content from the additional peroxide deco,,l~,ùsi,,y sulfur compound is at 0.02 to 0.30 ~/0 by weight.
Conveniently, the additional peroxide de~.o,,,,uosi,,y sulfur compound is selected from the group consisting of zinc 'i 'ky' '''~'liOCdl i dll I ' , copper dialkyl i,tl l;Ul.dliJdl11 or nickel yl~iitl l;UCdli dlIIdl~ wherein the dialky' ' 'h;u~,ddJdll ' has alkyl groups with 2 to 18 carbon atoms, bis(dialkylLl,;u~,d,ud",uyl)disulfide having an alkyl group with 2 to 18 carbon atoms, disulfide having an alkyl group with 2 to 18 carbon atoms.
disulfide having an allyl group, an alkylallyl group or an allyialkyl group, with 6 to 18 carbon atoms, olefin sulfide, fish oil sulfide, whale oil sulfide and mixtures of the any of the foregoing.
In a further aspect, the lubricant also cu~,udaes (F) from 1 to 10 ~~c by weight of one or more metal d~:Le~yt:ula selected from the group consisting of calcium salicylate, magnesium salicylate, calcium sulfonate, magnesium sulfonate and calcium phenate. Cu~ ,~.i. ,it utly the metal detergent is added at level providing from 0.5 to 8 percent by weight on an active ingredient basis. One lubricant within the present invention includes from 1.75 to 4 wt C/c (active ingredient basis) of calcium salicylate.
W0 96/0690~ 9~ - 4 - ~ P~ S
Conveniently, the lubricant compnses an oil of lubricating viscosity having added thereto (A) oxy",olybdenum iitlliùcdlL)dll ' sulfide having alkyl groups which may be the same or different with 8 to 18 carbon atoms, (B) zinc dialk~,ld;thiuuhus,uhal~: having pnmary alkyl groups with 1 5 to 18 carbon atoms, and (C) one or more additional sulfur compounds selected from the group consisting of zinc dialky'ditl,ioud,Ld" ', copper d "~Iditlliu~.dlbdllldLt7 or nickel " "~ylditlliùudllJdl.. ' wherein the d "<yldithiùcdlLdllldLt: has alkyl groups with 2 to 18 carbon atoms, bis(dialkylthiu,.d,L,d,,,oyl)disulfide having an alkyl group with 2 to 18 10 carbon atoms, disulfide having an alkyl group with 2 to 18 carbon atoms, disulfide having an allyl group, an alkylallyl group or an allylalkyl group, with 6 to 18 carbon atoms, olefin sulfide, fish oil sulfide and whale oil sulfide, (D and E) boron containing succinimide, and (F) one or more metal d~:~.yel lts selected from the group consisting of calcium salicylate, 15 magnesium salicylate, calcium sulfonate, magnesium sulfonate and calcium phenate, wherein to the total weight of the ..u,, r ~ the molybdenum content from oxymolybdenum ditllk)~.dlL)dlll ' sulfide Is at 200 to 2,000 ppm (ratio by weight); the pho~,ul ,u,uus content from zinc " 'kyllitl ,iopho~JI IdL~: is at 0.02 to 0.15 ~/0 by weight; the sulfur content from the additional sulfur compounds is at 0.02 to 0.30 ~/0 by weight; the content of a metal detergent is at 1 to 10 ~/O by weight; and the boron content from boron containing succinimide is at 0.005 to 0.06 % by weight.
Methods to detenmine the amount of molybdenum, phosphorus, ~5 boron, nitrogen, and sulfur are well known in the art. For example molybdenum, phosphorus, and boron can all be dut~.",i"ed by inductively coupled plasma atomic emission spe,,Gu,,,,:L,y, JPI-5S-38-92. Nitrogen may be d~te.lll;"ed by the chemil~""i,.~scence method described in JIS K
2609 7. Sulfur may be dt:L~ ;lled by the method described in ASTM D
5453 which involves ~o".~. Li"g sulfur to sulfur dioxide, exciting the sulfur dioxide with ultraviolet light and measuring the amount of fluorescent emission produced.
WO96/0690S 9$~7~ 11~ C~
Detailed Description As the lubricant b~ c~si~ck to be used in the lubricant cu",,uu:,;Liu, of the present invention, use may be made of those base oils cw, ~.,. ,t;ona:'y used, for example, mineral oils and synthetic oils, without S any specific limitation.
Thus suitable minerai oils include those made from raffinate produced by solvent purification of a lubricant raw material with an aromatic extraction solvent such as phenol and furfural, hyd,uye,,dLiùn plu~,~,s3ûil oils by hyd~ugendt;un plUUt:aS;~I9 with a hydlug~dliun catalyst such as cobalt and moiybdenum on the carner silica-alumina, or mineral oils such as lubricant distillate produced by wax isu~ d~dLiùll~ for example, 60 Neutral Oil, 100 Neutral Oil, 150 Neutrai Oil, 300 Neutral Oil, 500 Neutrai Oil, and Bright Stock.
cly, suitable synthetic oils include, for example, poly~-olefin oligomers, polybutene, ~ 'ky~ "~e.le, polyol ester, polyglycol ester, dibasic acid ester, phOaph ' ester, silicon oil and the like. These may be used singly or in colllL,i, IdLiol) with two or more, or a mineral oil may be mixed with a synthetic oil for use.
The base oil to be used in the lubricant cu,,,,uoaiLiun of the present invention has a viscosity at 100~C in the range of 3 to 20 cSt.
Particularly"u,.,'~ ".,e is given to a h~llugt:lldLiùn decu,,,~,uaiLiun oil and a wax isu""~ dLio" oil, with 3 ~/O by weight or less of aromatic co,,,,uùllellta~ 50 ppm or less of sulfur ~,ulll,uollellb and 50 ppm or less of nitrogen co~uùllellLa~
~5 As the oxymolybdenum dilll;u~,dlbdlll ~ sulfide to be blended with the lubricant cu, Il,uOa;Liu U of the present invention, use is made of a compound It:~.rc:se, ,' . by the general formula (1):
S x X X S 3 R
N_C_S _Mo Mo _S _C _N
\ /
RZ X F~4 ( 1 ) WO96~06901 2~9S~ 6- r~ll~3s~
wherein R1 R2 R3 and R4 may be the same or different each aelllLill9 an alkyl group with 8 to 18 carbon atoms; and x l~ a~lltS S
orO.
The alkyl group with 8 to 18 carbon atoms I~ a~ d by R1 R2 R3 and R4 in the general formula (1) may be linear or branched. For the lubricant of the present invention the carbon number of the alkyl group a:ll by R1 R2 R3andR4ismostpreferably8to13. Specific exampiesofthealkylgroup I~ by R1 R2 R3andR4 include 2-ethylhexyl octyl group nonyl group decyl group undecyl group I0 dodecyl group tridecyl group tetradecyl group pe"Lddecyl group hexadecyl group ht:~,tdJecyl group and octadecyl group.
In the lubricant ~ Clll~ O_;tiJII of the present invention one species of oxy,,,olyudenum dalliOCdlbdll sulfide may be used or two or more species thereof may be used in cc.llLi,ldliol,. Furthemmore I 5 oxymolybdenum lill liUCdl Ldl I ' sulfide is blended so that the u loly.,cle".lm content from oxymolybdenum ditl liU~.dl Udl l l ' sulfide in thefinished lubricant is from about 200 to about 2 000 ppm (ratio by weight) preferably 300 to 800 ppm (ratio by weight) to the total weight of the co",~,ositiùn. When ù~ y,,,ùiybde,,.lm liIh;u~.dlLdlllat~ sulfide is blended in an amount such that the "lolyude".lm content from u~",u yLde"um diLlliu dlbdll sulfide is below 200 ppm (ratio by weight) to the total weight of the cOIlluuailiull the effect of improving the mction properties (low friction) is not sdliard~.Iul Iy exhibited; and when oxymolybdenum ditlliocdludllldltl sulfide is blended at an amount such that the ""~Iybde",Jm contentfrom oxymolybdenum dillliu dlbdlll sulfide is above 2 000 ppm (ratio by weight) to the total weight of the CO",,.~O:,ii;ul"
the improvement of the effect is not observed in proportion to the amount and sludge is likely to be caused. Oxymoiybdenum ditlliul dludllldLt:
sulfides are well known and available CO"""t:~ Iy. Rey, :a~ ,Ldli./e methods for their ~ .IdldliUII are described in US 4 098 705.
As the zinc dialkyl lithiu~hOaul IdLtl to be blended with the lubricant co",~osiliun of the present invention use is made of a compound IC~ aellL~:d by the general fommula (2):
~ 21 95~ 75 Wo 96/0690~ ~ ~ 7 ~ P~ ~ S
Rs _ O ISl S o--R7 /P--S--Zn--S--P
Rs_O O--Rs wherein R5, R6, R7 and R8 may be the same or different, each re~,,eaelllil,g a primary alkyl group with 1 to 18 carbon atoms. They may 5 be prepared in ac.,o, ian-,e with known techniques by first fomming a dihydrocarbyl iitlliOphoaullo,i., acid (DDPA), usually by reaction of one or more primary alcohol with P2Ss and then neutralizing the fommed DDPA
with a zinc compound. To make the zinc salt, any basic or neutral zinc compound could be used but the oxides, hydroxides and cd,L,on..t~. are 10 most generally employed. Commercial additives frequently contain an excess of zinc due to use of an excess of the basic zinc compound in the neutralization reaction. In order to obtain oil solubility, the total number of carbon atoms in the alcohols reacted to form the .,i;hiu,uhùs~,l,o,ic acid will generally be about 5 or greater.
The primary alkyl group le~,rus~ by R5, R6, R7 and R8 in the general formula (2), may be in a linear chain or in a branched chain, including for example rnethyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl sroup, dodecyl group, tridecyl group, tetradecyl 20 group, pentadecyl group, hexadecyl group, he~Jtddecyi group and octadecyl group. In the lubricant COIIIuuaitiull of the present invention, preferably, use may be made of zinc dialkylditl,;u,uhoayhdle having a primary alkyl group with 3 to 12 carbon atoms.
In the lubricant cul "poSiliuil in ac"u, id"-,e with the present 25 invention,zinc i 'k~lditll,ophosul, ' isblendedsothatthepl,uapho,uus content from zinc diaiky'dilhiophoa,uhdle is at û.û2 to û.15 ~/0 by weight, preferably û.04 to 0.12 ~J0 by weight to the total weight of the cu~l~poslliun~
When zinc dialkyk~;;hiuulloaphdle is blended at an amount such that the phuauhuluus contentfrom zinc iidlkyluitllluullosplldle is below 0.02 ~/0 by 30 weight to the total weight of the uullluOailiul1, the resulting collluoailiuncannot get c~ f .I. ,ry wear p~:~ rul ll ldl lce or cannot get a small coeffficient W096/0690.~ 2l95~5 -8- ~ c of friction ~dliardululy under the operation cu, Iditiulla of high oil temperature and low-speed rotation; and when zinc dialkyldiLl,iu~llG ,~uhdL~ is blended at an amount such that the uhua,uholu.ls content from zinc, " " yl~lithiopho:,~ul IdLt: is above 0.15 ~/0 by 5 weight to the total weight of the CC~ uO ,iLiul " the improvement of the effect is not observed in proportion to the amount.
The additional sulfur compound required for the present invention is selected from any of the sulfur compounds that efficiently decu,,,~ose peroxides. Without intending to be bound by any theory, the extended 10 fuel economy pe, ru" "ance of the present invention may be attributable to suppressed consumption ofthe oxy",olyL,del,um ' ''liu~,dlLdllldLt: sulfide and the zinc dialkyWithiuuhu:,ul IdLt: because the sulfur compounds effficiently ;iecu,"uuae peroxides.
As the " 7<yldiLI lioUdlLldlll ' salt to be blended in the lubricant 1~ culil~Jùsiliun of the present invention, use is made of a compound ,":ae"~d by the general formula (3) R9 S llS
o,N - c - s - M--S--C N~R12 wherein M ,t:~ ,u_~.lta zinc, copper or nickel; R9, R10, R11 and R12 may be the same or different, each r~:,u~t:S~"~;"g an alkyl group with 2 to 18 ZO carbon atoms. Metal salts of ~ Witllio~,dlbdllli~. acid are well known and readily available. Processes for their synthesis are described in US
4,623,473 and 4,740,322.
The alkyl group of 2-18 carbon atoms ll:~u~se~Le:d by R9, R10, R1 1 and R12 in the general fommula (3) may be linear or branched, Z~ inciuding for example ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pe"Ladecyl group, hexadecyl group, he~Lddecyl group and octadecyl group.
~ 9S~ 75 . .
WO 96/06904 9 _ ~ O s r~
As the bis(dialkylll,iu-,d,bd~"u,rl)disulfide to be blended in the lubricant cuu,~,ùsiiio n of the present invention, use may be made of a ~ compound le~luae.lled by the general formula (4):
R13\ S 11 ,RI5 N--C--S--S--C--N
R14/ ~Rl6 S wherein R13 R14~ R15 and R16 may be the same or different, each leuleSelltill9 an alkyl group with 2 to 18 carbon atoms The alkyl group of 2-8 carbon atoms l~,ulu__.lled by R13, R14, R15 and R16 in the general fommula (4) may be linear or branched, including for example ethyl group, propyi group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pe"td.iecyl group, hexadecyl group, he~Jtddecyl group and octadecyl group.
As the disulfide to be blended in the lubricant Culll~JùaitiOIl of the present invention, use is made of a compound le~Jltaa~ by the general fommula (5):
R17~s_R18 (5) wherein R17 and R18 may be the same or different, each re,u~ ti"9 an alkyl group with 2 to 18 carbon atoms or an allyl group.
an alkylallyl group or an allylalkyl group, with 6 to 18 carbon atoms. The alkyl group of 2-8 carbon atoms lelJIesellled by R17 and R18 in the general fommula (5) may be linear or branched, including foc example ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pe~llddd~ l group, hexadecyl group, heptadecyl group and octadecyl group; the allyl group, the alkylallyl group or the allylalkyl group, having 6 to 18 carbon atoms and being ~e~ __. ' by R17 and R18, includes for example phenyl group, benzyl group, phenetyl group, methylbenzyl group, diphenylmethyl group and the like.
gS4~5 W0 9610690~ 0 - . ~ b7~
Olefin suifide, fish oil sulfide and whale oil sulfide, to be blended with the lubricant ~,ulll,uua;;iun of the present invention, should be olefin sulfide (polysulfide) being produced by sulfide p,u.,~ssi"g of polymers such as isobutylene and having a sulfur content of 25 to 40 ~/0 by weight, 5 fish oil sulfide and whale oii sulfide produced by p,u~,esai"g individually fish oil and whale oil in the same manner.
In the lubricant colll,uuailion of the present invention, the metal dialkyl iitl liUUdl bdl I Idk~ ,UI t:ael I ' ' by the general fommula (3), bis(dialkyl11,ioca,bd""~yl)disulfide It:~Jn:ar-llLed by the general fomlula (4),10 disulfide r-:,u,~sr-"t~d by the general fommula (5), olefin sulfide, fish oilsulfide and whale oil sulfide, may be used singly or in cu,l,L,i, IdLiUU of two or more thereof. These sulfur compounds may be blended so that the sulfur content derived from these added sulfur compounds is 0.02 to 0.30 O~D by weight. When these sulfur compounds are blended at an amount 15 such that the sulfur content from these added sulfur compounds is below 0.02 ~/0 by weight to the total weight of the ,,u,,,,uosiLiùn, the effect of sl ~ ' .;1 ~y friction decrease is insuffcient; when these sulfur compounds are blended at an amount such that the sulfur content from these sulfur compounds is above 0.30 ~/0 by weight to the total weight of the 90 uulll,uuait;OIl, the improvement of the effect cannot be brought about in p,u,uu~Liùn to the amount.
If desired, one or two or more metal d~t~. y~l ,ts selected from the group consisting of calcium salicylate, magnesium salicylate. calcium sulfonate, magnesium sulfonate, and calcium phenate may be blended ~5 with the lubricant ~,c~lll,u05iLiun of the present invention. These metal d~LI::ry~l ILa may be blended at 1 to 10 ~/O by weight to the total weight of the .,u,,,uùsiLiùm Vvhen these metal detergents are blended below 1 ~/0 by weight to the total weight of the cu" IpuaiLiul " the cleansing effect is u,~ ry, when these metal d~t~.y~l,ts are blended above 10 ~/O by 30 weight to the total weight of the Cul",uOaltiuil, the improvement of the effect cannot be observed in proportion to the amount, or rather, ash content may increase. Recoy"i~i"g that metal d~ ~.y~ comprise oil sl,a,uensiù,ls of neutral and overbased metal salts of organic acids, the 219S~75 ~ - r WO 9610690~1 . ..,. ~f ~ ~ ~ P~
treat rates recited cu, ~ uond to treat rates of from about 0.5 to 8 weight percent active ingredient.
Metal-containing or ash-fomming d~t~ryer,ts generally comprise a polar head with a long hyd,u~llot,i~. tail, where the polar head is a metal 5 salt of an acidic organic compound. The salts may contain a substantially ~tùk,ll;w~ lliu amount of the metal in which case they are usually described as nonnal or neutral salts, and would typically have a total base number or TBN (as may be measured by JIS K2501) of from 0 to 80. It is possible to include large amounts of a metal base by reacting an excess 10 of a metal compound such as an oxide or hydroxide with an acidic gas such as carbon dioxide. The resulting oie.l,a:.,ad detergent comprises neutralized detergent as the outer layer of a metal base (e.g. carbonate) micelle. Such ov~.L,a~ed d~ .yt:l,ts may have a TBN of 150 or greater, and typically of from 250 to 450 or more.
Sulfonates may be prepared from sulfonic acids which are typically obtained by the s~l'' Idliun of alkyl s~hs'i~ t ' aromatic hJdlu~.dlLul,a such as those obtained from the Fld~liulldliùn of petroleum or by the alkylation of aromatic l.Jd, U~dlbUn:l The oil soluble s~ or alkaryl sulfonic acids may be neutralized with oxides, hydroxides, alkoxides, 20 I,dlborldt~s, udlLJuxy, ', sulfides, hydrosulfides, nitrates, borates and ethers of the alkali metal. The amount of metal compound is chosen . having regard to the desired TBN of the final product but typically ranges from about 100 to 220 wt % of that ~I~,i,,hiu,"~l, "y required.
Metal salts of alkyl phenols and sulfurized alkyl phenols are 25 prepared by reaction with an d,u~ulufJIidLe metal compound such as an oxide, hydroxide or alkoxide and overbased products may be obtained by methods well known in the art. Sulfurized alkyl phenols may be prepared by reacting an alkyl phenol with sulfur or a sulfur cu,,~ ,i"y compound such as hydrogen sulfide, sulfur ",ol10h ' '~ or su fur dihalide, to form 30 products which are generally mixtures of compounds in which 2 or more phenols are bridged by sulfur containing bridges.
Metal salts of carboxylic acids (including salicylic acids) may be prepared in a number of ways: for example, by adding a basic metal W096/0690~1 2~954~ 12- ~ s compound to a reaction mixture uu,, ,~ ,i, ,9 the carboxylic acid (which may be part of a mixture with another organic acid such as a sulfonic scid) or its metal salt and promoter, and removing free water from the reaction mixture to fonm an metal salt, then adding more basic metal S compound to the reaction mixture and removing free water from the reaction mixture. The carboxylate is then ov_.L,ased by introducing the acidic material such as carbon dioxide to the reaction mixture while removing water. This can be repeated untii a product of the desired TBN
is obtained.
The overbasing process is well known in the art and typically comprises reacting acidic material with a reaction mixture cu,,,,u,i~i,,g the organic acid or its metal salt, a metal compound. That acidic material may be a gas such as carbon dioxide or sulfur dioxide, or it may be boric acid. Processes for the p,e~dldliun of o./e.bdsed alkali metal sulfonates and phenates are described in EP-A-266034. A process suitable for overbased sodium sl~'h Idlt:~ is described in EP-A-235929. A process for making overbased salicylates is described in EP-A-351052.
The overbased metal ci~t~ "ts can be borated. The boron may be introduced by using boric acid as the acidic material used in the 20 overbasing step. However an ' Il..ti-C is to borate the overbased product after fommation by reacting a boron compound with the overbased metal salt. Boron compounds include boron oxide, boron oxide hydrate, boron trioxide, boron trifluoride, boron tribromide, boron trichloride, boron acid such as boronic acid, boric acid, tetraboric acid and metaboric acid, 25 boron hydrides, boron amides and various esters of boron acids. Boric acid is preferred. Generally, the overbased metal salt may be reacted with a boron compound at from 50~C to 250~C, in the presence of a solvent such as mineral oil or xylene.
Conveniently, the lubricant cu, l ,,uu ~;~iuil of the present invention 30 contains an overbased metal detergent in an amount sufiicient to provide a total base value of the finished lubricant in the range from about 3 to about 10, more preferably from 4 to 7. The total base value can be ~ Z19s~7~ ' WO 96/0690~ -13 - r~ ''C . /~;
~ ~*
measured according to JIS K2501. The total base value can be adjusted preferably by selecting a metal detergent with an dU,UIU,UI idi~ base value.
. .
If desired, an ashiess d;;"uu,ad"l may be biended into the lubricant.
The ashless d;~uer~d"l collljulisds an oil solublizing poiymeric S hydlucdluoll backbone having functionai groups that are capable of assouidtillg with particles to be dispersed. Typically, the di~,~er~d"ts comprise amine, alcohol, amide, or ester polar moieties attached to the polymer backbone often via a bridging group. The ashless di~pCll::~dllL
may be, for example, selected from oil soluble salts, esters, amino-esters, 10 amides, imides, and, ,es of long chain llydlu~dluull 5llh mono and di~,dl UUAyliC acids or their di Ihy.il kies, LhiU~,dl UUAy' derivatives of long chain hyd~UUdlUU115, long chain aliphatic hydlu~,d,bons having a polyamine attached directly thereto, and Mannich cor,densdLiu"
products formed by condens;"g a long chain sllhctitll~~1 phenol with 15 fu~udl~ hyde and polyalkylene polyamine.
The oil soluble polymeric hydlul,dlbùll backbone is typically an olefin polymer, especially polymers co,,,,u,;~ a major molar amount (i.e.
greater than 50 mole %) of a C2 to C18 olefin (e.g., ethylene, propylene, butylene, isobutylene, pentene, octene-1, styrene), and typically a C2 to 20 Cs olefin. The oil soluble polymeric h~dlu~,dlLJull backbone may be a homopolymer (e.g. polyp,uu,~la.)e or polyisobutylene) or a copolymer of two or more of such olefins (e.g. cu,uOl~ a of ethylene and an alpha-olefin such as propylene and butylene or ~,u,uoly,,,_,:, of two different alpha-olefins). Other copolymers include those in which a minor molar '5 amount of the copolyme m~lullGII ,a,~, e.g., 1 to 10 mole ~/0, is a C3 to C22 non-conjugated diolefin (e.g., a copoly",ar of isobutylene and butadiene.
or a copolymer of ethylene, propylene and 1,4-hexadiene or 5-ethylidene-2- no, bu, "ene). One preferred class of olefin polymers is polybutenes and spe,,iril,..l,y polyisobutenes (PIB) or poly-n-butenes, such as may be 30 prepared by pcl~lue~ dLiùn of a C4 refinery stream.
The oil soluble polymeric hydlu~dlboll backbone will usually have number average molecular weight (Mn) within the range of from 300 to 20,000, conveniently 500 to 10,000, and usually 700 to 5,000.
~9~47S ~
W0 96/069W - i4 ~ /~. . 7~a Particularly useful olefin polymers for use in di~e,~dllt~ have Mc within the range of from 1500 to 3000. The Mc for such polymers can be detellllllled by several known techniques. A convenient method for such deLe u l liU dLiUI I is by gel pe", led LiUI I ul 11 Ul I IdLUy l dlJ h y which adui'i~
5 provides molecular weight distribution i"rul IlldLiUn, see W. W. Yau, J. J.
Kirkland and D. D. Bly, "Modem Size E-xclusion Liquid ChlullldLuyld~ully John Wiley and Sons, New York, 1979.
The oil soluble polymeric h~JluudlL1u~ backbone may be fu, n~Liùndli~e i to i, ,~,u, ,UUldle a functional group into the backbone of the lO polymer, or as one or more groups pendant from the polymer backbone.
The functional group typically will be polar and contain one or more hetero atoms such as P, O, S, N, halogen, or boron. It can be attached to a saturated hyJ, U-,dl LJUI I part of the oii soluble polymeric hydl Ul,dl LJUn backbone via s~ Ihstitution reactions or to an olefinic portion via addition or 15 cycload iitiu" reactions. AlLelll "~cly, the functional group can be ,ul,uuldteJ into the polymer in conjunction with oxidation or cleavage of the polymer chain end (e.g., as in u~u"u'ysis).
Useful fu, ILLiùridli~dliùn reactions include: halùge~ Liùll of the polymer at an olefinic bond and C~hspciupnt reaction of the lidlùgendled 20 polymerwith an etl-llc,li....:'J unsaturated functional compound; reaction of the polymer with an unsaturated functional compound by the "ene"
reaction absent hdluyelldLiun (e.g., maleation where the polymer is reacted with maleic acid or anhydride); reaction of the poiymer with at least one phenol group (this permits derivatization in a Mannich base-type 71; COIldell~dliOIi); reaction of the polymer with the full~.Liùlidli~ y compound by free radical addition using a free radical catalyst; reaction with a Illiul,dliJu.~ylic acid derivative; and reaction of the polymer by air oxidationmethods, ~IJ, ~ n, ul llul udl l lil ldLiul~, or ozonolysis.
The fiJ, lULiUi idG~ed oil soluble polymeric h~ Ul,dl bU~ I backbone is 30 then further derivatized with a nucleophilic reactant such as an amine.
amino-alcohol, alcohol, metal compound or mixture thereof to fomm a cullea,uùliui"g derivative. Useful amine compounds for derivatizing fi~"uLiul Idli~ed polymers compnse at least one amine and can comprise ~ 219s~7~S ' WO 96/0690-1 15 9 r- - P~, 1/ '/C . /~a .i. ~
one or more additional amine or other reactive or polar gnoups. These amines may be hydrocarbyl amines or may be u,c:dulll;,ldlllly hydrocarbyl amines in which the hydrocarbyl group includes other groups, e.g., hydroxy groups, alkoxy groups, amide groups, nitriles, i" ' ' ,e 5 groups, and the like. Particularly useful amine compounds include mono-and polyamines, e.g. polyalkylene and PO!Y~JAY "cylene poi!r~_."i"es of about 2 to 60, conveniently 2 to 40 (e.g., 3 to 20), total carbon atoms and about 1 to 12, conveniently 3 to 12, and 3 to 9 nitrogen atoms in the moleculë.
The fullr_Liùlidli~t:d oil soluble polymeric hydlu.,dluull ba.,kbo"~:a also may be derivatized with hydroxy compounds such as monohydric and polyhydric alcohols or with aromatic compounds such as phenols and naphthols.
A preferred group of ashless di~ ad~,'s includes those 15 5llhstitll~~ ~ with succinic anhydride groups and reacted with polyethylene amines ~e.g., l~l,dc:Ll,ylene p~ltd~ le), dlllill ' huL, such as trismethylold",i"u",.,Ll,d"e and optionally additional reactants such as alcohols and reactive metals e.g., pentaerythritol, and culllu;lldLiull~
thereof). Also useful are d i~ ladl,ts wherein a polyd",i"e is attached '0 directly to the backbone by the methods shown in US 3,275,554 and 3,565,804 where a halogen group on a hdlogen ' ' hydlu.,d,uù,, is displaced with various alkylene pu.y_."i"es.
Another class of ashless d;~"~ladllts uulll,uriaes Mannich base condcnsdliun products. Generally, these are prepared by co"uensi"g ~5 about one mole of an alkyl-s~ IhCtitl ltPd mono- or polyhydroxy benzene with about 1 to 2.5 moles of carbonyl compounds (e.g., fulllldWl~ e and pdl dfu""aldel ,yde) and about 0.5 to 2 moles polyalkylene polyamine as disclosed, for example, in US 3,442,808. Such Mannich coode, ladliol l products nnay include a long chain, high molecularweight hyu,u.,d,bon 30 (e.g., M,l of 1,500 or greater) on the benzene group or may be reacted with a compound r_Ul lLdil ,i"g such a hyrllu~,d,bùl " for example, polyalkenyl succinic anhydnde as shown in US 3.442,808.
, ~. . , 2Jgs4~5 ' ~
wos6/06sn~ - 16~ S
Theful~,liùl~ ' " ns,cie, i~/dt;Lcli;Ulla, andpost~ dt~ ts described in the following patents may also be adapted to fullr~ i;oudli~
and/or derivatize the preferred polymers descnbed above: US 3,275,554.
3,565,804, 3,442,808, 3,442,808, 3,087,936 and 3,254,025.
The u'i~ ,ad"l can be further post-treated by a variety of conventional post I", dilllCI Ua such as boration, as generally taught in US
3,087,936 and 3,254,025. This is readily a,_,_w,,~ .l,ed by treating an acyl nitrogen-containing di~,J6laell~I with a boron compound selected from the group consisting of boron oxide, boron haiides, boron acids and l O esters of boron acids, in an amount to provide from about 0.1 atomic proportion of boron for each mole of the acylated nitrogen .,ul, l~oaition to about 20 atomic p, up~JI liùns of boron for each atomic proportion of nitrogen of the acylated nitrogen ~,ulllr~Jua;ii.Jil. The boron, which appears be in the product as del "/dl dl~:r j boric acid poiymers (primarily (HB02)3), 1~ is believed to attach to the di~r,Jeladl~I imides and diimides as amine salts e.g., the IllI:IdbUl ' salt of the diimide. Boration is readily carried out by adding from about 0.05 to 4, e.g., 1 to 3 wt. % (based on the weight of acyl nitrogen compound) of a boron compound, preferably boric acid, usually as a slurry, to the acyl nUrogen compound and heating with stirring at from 135~ to 190~ C, e.g., 140~-170~ C, for from 1 to 5 hours followed by nitrogen stripping. r. " . Iy, the boron treatment can be can ied out by adding boric acid to a hot reaction mixture of the di"dliJu,~y'i~, acid material and amine whiie removing water.
When the d;~,r,Jt:~ad"I is a nitrogen containing diar,Jt:ladllI, the ratio 2~ of the number of boron atoms/the number of nitrogen atoms in the boron containing succinimide to be used in the lubricant COIll~ uailiun of the present invention is 0.05 to 1.5, preferably 0.1 to 0.8. If the ratio of the number of boron atoms/the number of nitrogen atoms is below 0.05, sdIiardl,Iuly improvement of friction properties (low friction) cannot be brought about; if the ratio of the number of boron atoms/the number of nitrogen atoms is above 1.5, friction properties are d~. iUldirr d.
In the lubricant culll,uOaiIiul, of the present invention, the boron containing succinimide should be blended at an amount such that the W0 96/0690~ ~ - 17 -~. ~.
boron content from boron uu, ,;"9 succinimide is at 0.005 to 0.06 ~/0 by weight, preferably 0.01 to 0.04 ~/0 by weight to the total weight of the cc""po .i~ion. When the boron containing succinimide is blended at an amount such that the boron content from boron containing succinimide is S below 0.005 ~/0 by weight to the total weight of the cc,."~,u~itiui), no " ' ' y improvement of friction properties (low friction) can be brought about; if the boron cc" lld;ll;l 19 succinimide is blended at an amount such that the boron content from boron containing succinimide is above 0.06 ~/0 by weight to the total weight of the ~,U~pOsit;ul), no i,,,,u,u~,l,c.ll of the eMect can be brought about in proportion to the amount.
In a range without departing from the scope of the present invention, various additives cu, ,~l_. " ) "y used for lubricants, for example, other friction modifiers, other metal du'~r ,t:"b, other wear preventing agents, dlLUA; idllt:~, viscosity modifiers, pour point de~,eas;"y agents, anti-foaming agents, nust ,cl-,l_.l .l., agents, and corrosion inhibitors, may be blended in the lubricant cu",~,os;i;un of the present invention.
Other friction modifiers include for example polyhydric alcohol 2D partial ester, amine, amide, sulfide ester and the like. Boration of friction modifiers is well known in the art and ,t~ ,e"t~ an " " ~c way to introduce boron into the lubricant.
Other metal detu,y~l lt~ include for example barium sulfonate, barium phenate and the like, which may be used generally at a ratio of '5 0.1 to 5 ~/O by weight.
Other wear preventing agents include for example lh;u~il ,os~,l Idlt:
metal salt, sulfur compound, ,uhu~ ihat~ ester, phosphite ester and the like, which may be used generally at a ratio of 0.05 to 5.0 % by weight.
Al ll;OA; idl ,ts include for example amine dl ll;UAk,idl ,ts such as ~ 30 alkylated diphenylamine, phenyl-a-naphthyiamine, and alkylated a-naphthylamine; and phenol a"liuxidc,r,la such as 2,6-di-t-butyl-4-methyl ~9~
W096/0690.1 C~ -18- .,111 931. I~a phenol and 4,4'-methylene-bis(2,6-di-t-butyl phenol), which may be used generally at a ratio of 0.05 to 4 ~/0 by weight.
Viscosity modifiers (aiso frequently called viscosity index improvers) include for example poly" luil ,a~., ylates, polyisobutylenes, 5 ethylene-propylene Cu,uu'y~llula, styrene-butadiene hydluyelldlud cupoly"~ a and the like, which may be used generally at a ratio of 0.5 to 35 ~/0 by weight.
Pour point de~ as;"g agents include for example polyalkylmethacrylate, ~,1 ,lu, i, Idtc:d paraffin-r,a~ Ihdl~:l ,e con.le"sed 10 product, alkylated polystyrene and the like.
Anti-foaming agents include for example dimethylpolysiloxane, ~ polyacrylic acid and the like.
Rust preventing agents include for example fatty acid, alkenyl succinate partial ester, fatty acid soap, alkylsulfonate salt, fatty acid 15 polyhydric alcohol ester, fatty acid amine, paraffn oxide, alkylpolyoxyethylene ether and the like.
Corrosion inhibitors include for example be, ,~ul, id~ule and b~"~ui" li~
20 Examples The present invention will now be explained in detail in examples.
but the invention is not limited to these examples.
Herein, the coeffcient of friction of the lubricant cu" ,,uositk,n was measured at a 50-Hz frequency, a 3 mm dl~ le, a 25-N load, a 25 temperature of 80~C and a testing period of 25 minutes, using a :l,;,UlU-~dLt: dynamic sliding friction tester (SRV friction tester).
The oxidation test by means of air cu":..;.,;"9 gaseous nitrogen oxides was carried out using a 150 ml test oil at a temperature of 1 30~C.
a nitrogen oxide level of 1 ~/0 by volume. a flow of 2 liters/hour, and a iO testing period of 8 hours.
~ 21 9~ 7~
W096/06901 ~ 19- ~ re .~, r ~ it,=
Examples 1 to 9 and Cu~ al ' ~u Examples 1 and 2 Examples 1 to 9 are lubricant c~lll,uO:~;Liùlla blended with (A) ox~",ùlyu ie"um iitlliuudli dllldle sulfide, (B) zinc diaik~,l iitl,iu~ul,u~,l,dle, (C) zinc dialkyi ~liUl,dliJdll , copper, lk~lui;l,iu,,d,ua,,, 5 bis(dialky;'hiùud,ua,,,ùyl)disulfide ordibenzyldisulfide, (D) calcium salicylate, and (E) boron culltaill;ng succinimide. Fullllellllule, Colll,Udl ~C Examples A and B are lubricant cU"~,UUsitiull . containing the culll~Jùnellts (A), (B), (D) and (E), without ~c",'..:.,i"g the Culll,ùollellL (C).
Individual uullluul-elltS of a type and an amount shown in Tabie 1 lo were blended with the base oil (100 Neutral Oil with a viscosity of 4.4 mm/s2 at 100~C) to prepare lubricant cu"")ositi~."~ cc."L..;.,i"g the cu,~,,uun6,~ts~ and the uuerri~,ie"l of friction i"""e.,i '~!y afterthe I~e,ua, ' ~ was measured, together.with the ~.oerfi~iel ,L of friction after the F;l-r- ' 15 were stored and oxidized in the presence of gaseous nitrogen oxides at 1 30~C for 8 hours. The results are shown in Table 1.
All the lubricant cu"., ' ns of Examples 1 to 9 all have good friction properties with low cueffi.,iel ~ts of friction. No change in the cu_rfi.,;_, hs of friction was observed even after the lubricant cu, "~JOsitiul ,~
were heated in the presence of gaseous nitrogen oxides at 130~C for 8 20 ' hours. Thus, it is indicated that these lubricant cu" "~ositiu"~ have good le~i~lance to oxidation with no change in the observed coerri-,ie~.s of fn'ction. Altematively, the lubricant coll,r " ,s of Cu~llJa~..:iii Examples A and B, without ~.U~ Itai~ ly the ~ uullelll (C), i.e., a sulfur compound, have low c4erri~,iel Its of friction i" ", . - " 'y after ~ll eudl dLio~ ~, 25 but have acquired higher coefri~,ienk~ of friction after the ,u~e,udldLiul ,~were heated and oxidized in the presence of gaseous nitrogen oxides at 130~C for 8 hours, indicating that their ,~ ' ' ,..e to oxidation is poor.
The lubricant ~.u",uo:.iliu" of the present invention has acquired good low abrasion property, through the blending of a lubricant base oil 30 with u.~y."ù.yL,der"~m dithiOUddJd~l sulfide, zinc dialkyi ' 'hiopl,usul, ', and a sulfur compound, each having a specific structure, a metal detergent and boron ~ Lail~ g succinimide. The cu",,uu ~iLiun can sustain good friction properties (low friction) while exhibiting resistance to WO 96/0690~1 - 20 - 1~
oxidation at higher temperatures in the presence of gaseous nitrogen oxides, and is preferably used as lubricants for intemal combustion engines, automatic Lld~ ion, snubbers, and power steering, preferably for intemal combustion engines in particular.
~ 2 ~ 4~5 W0 96/06904 l ~ Ja,; /~a -o Om o, Q ~1 ~D o ~ '~ ~
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WO 96/06904 , , , P~
Lubricants with .c..c~ i n~ Fuel Economy r~. ru, 1, Idl .ce Field of the Invention The present invention relates to a novel lubricant c~ n.
S More ~ it relates to a lubricant c~"l,u~ i, having good low abrasion and friction ululJe~ti_3 and being capable of SIXf ' ~ I;lly 1Ow friction over a long period of bme with no cl~ iuldtiun even in an dtllluapllele COl ' 1 19 gaseous nitrogen oxides. The lubricant colll~ua~iull can be used in intemal combustion engine cldl)k~.d~lea, 10 automatic t,dna",; ,s;.~ns, wet brakes and power steering. Preferably it is used in uldllkl~d~e~ of intemal combustion enyines.
Background of the Invention Lubricants have been used to lubricate intemal combustion engines, driving systems such as automatic bd"~",;a~ion, wet brakes and 15 power steering; and gears. Lubricants for intemal combustion engines in particular have as their primary function lubricating various sliding parts such as piston rings and cylinder liners, ~lallk~l ~ bearinss and Col Ine~.~il Iy rod, and valve operabng parts. Beyond this primary function ..,d"h.ase lubricants also serve to cool the inside of engines, to clean 20 engine parts, to disperse combustion products, and further to prevent rust and conrosion.
In recent years intemal combustion engines have been modified to lower fuel consumption while i"u, edail Iy power output and -improving durability even under severe operating conditions. In consequence 25 greater demands have been placed on lubricants. In addition, c~mhufr~ gases from internal combListion engines leak from between the piston and the cylinder into the crankcase in the fomm of blow-by-gas.
These combustion gases contains higher levels of gaseous nibrogen oxides, which together with oxygen in the blow-by-gas cletel iu~ the 30 lubricants. The levels of gaseous nitrogen oxides leaking into the ~.ldllk~dse tend to increase as engine pelrul",allce demands increase.
To prevent d~.b,.iu,dLiun in an dtlllU l,uhele COIIta;~ gaseous nitrogen oxides, while retaining lubricity pe~ru~ d~lue, lubricants are blended with various additives, for example, wear ~ , .,ti.,g agents, metal salts of CONFIRM~llON COI~
WO 96/06901 r~
organic acids commonly known as d~Lelye l ~ta, ashless .I;~ adl lta, and dl ILiU~ dl ILa.
Engine lubricating parts are mostiy in a state of fluid lubrication, but vertical dead centers of valve operating systems and pistons are likely in S a state of interface (or boundary) lubncation. In such a state of interface - lubrication, wear preventing properties are generally provided by adding zinc '''liupl~a~JII. '~.
Friction modifiers are also added to the lubricants as a cou"L~:""ea~lre to decrease effficiency loss from friction and thereby 10 reduce fuel consumption. As such friction modifiers, for example, organic molybdenum compounds, fatty acid esters, alkylamines and the like, are used in general.
After intensive i"Je ':~ '' )ns under such circumstance, it has been found that friction modifiers are effective in a fresh lubricant, that is, at the 1~ initial stage of use after their addition, but friction modifiers lose their effect when they are oxidized and dl:Lt:riol ' by dtlllua~/he~ oxygen, and that the decrease of the effficacy is distinctive in the presence of gaseous nitrogen oxides. Thus, the present invention has been achieved forthe purpose of developing a lubricant .,ulllr " n which can provide 'O sustained fuel economy pe,ru""ance with the effect of de~"~dai"g friction in engines for a long period of time in the presence of gaseous nitrogen oxides.
Summary of the Invention - A lubricant has been discovered that has good lubricity and aiaLdl l~,e to dl:L~:, io,dLiol, in the presence of oxygen and gaseous nitrogen oxides. It comprises a major amount of a lubricant base oil, a b..~e~ k of lubricating viscosity, to which a minor amount of additives has been added. The additives comprise specific amounts of oxymolybdenum diilliucdlLJd~ u sulfide having specific alkyl groups, zinc ,0 dialkyl,liLhiophuayhdt~ having specific alkyl groups, one or more specific sulfur collLdillillg compounds, an ashless ~ ,ad"l and a boron ~,u, ' ,;.,9 additive which may be the ashless di~pe,ad"L. In further 21g5~,7~
WO 96/0690~ - 3 -~ .
~ ~=.
aspects of the invention a metal detergent is used. Co~ llIly, the Jelad"L and boron are added as a borated succinimide. Thus, the ~ present invention has been achieved on the basis of the finding.
The present invention is a lubricant ..c" ",ua;.ion cw"~,,iaiuy a major amount of a lubricant base oil having added thereto a minor amount of additives co"",,iai"g (A) uxy,l~ulyb i~::"um ~"'tl;U~dli dll - '~ sulfide having aikyl groups with 8 to 18 carbon atoms, (B) zinc dialky' ' '',;u,uhosyl ' having primary alkyl groups with 1 to 18 carbon atoms, (C) one or more additional peroxide deculll~Joa;,ly sulfur compounds, (D) an ashless di."J~Iadlll, and (E) a boron containing additive in an amount sufficient to provide at from 0.0û5 to 0.06 C/o by weight boron to the finished lubricant wherein to the total weight of the culll,uG~;liull, the molybdenum content from oxymolybdenum iitlliuudliJdllldL~ sulfide is at 200 to 2,000 ppm (ratio by weight); the pllu:,pholu.ls content from zinc ' 'hyWitlliuphoa~Jh. '~ is at 0.02 to 0.15 C/o by weight; and the sulfur content from the additional peroxide deco,,l~,ùsi,,y sulfur compound is at 0.02 to 0.30 ~/0 by weight.
Conveniently, the additional peroxide de~.o,,,,uosi,,y sulfur compound is selected from the group consisting of zinc 'i 'ky' '''~'liOCdl i dll I ' , copper dialkyl i,tl l;Ul.dliJdl11 or nickel yl~iitl l;UCdli dlIIdl~ wherein the dialky' ' 'h;u~,ddJdll ' has alkyl groups with 2 to 18 carbon atoms, bis(dialkylLl,;u~,d,ud",uyl)disulfide having an alkyl group with 2 to 18 carbon atoms, disulfide having an alkyl group with 2 to 18 carbon atoms.
disulfide having an allyl group, an alkylallyl group or an allyialkyl group, with 6 to 18 carbon atoms, olefin sulfide, fish oil sulfide, whale oil sulfide and mixtures of the any of the foregoing.
In a further aspect, the lubricant also cu~,udaes (F) from 1 to 10 ~~c by weight of one or more metal d~:Le~yt:ula selected from the group consisting of calcium salicylate, magnesium salicylate, calcium sulfonate, magnesium sulfonate and calcium phenate. Cu~ ,~.i. ,it utly the metal detergent is added at level providing from 0.5 to 8 percent by weight on an active ingredient basis. One lubricant within the present invention includes from 1.75 to 4 wt C/c (active ingredient basis) of calcium salicylate.
W0 96/0690~ 9~ - 4 - ~ P~ S
Conveniently, the lubricant compnses an oil of lubricating viscosity having added thereto (A) oxy",olybdenum iitlliùcdlL)dll ' sulfide having alkyl groups which may be the same or different with 8 to 18 carbon atoms, (B) zinc dialk~,ld;thiuuhus,uhal~: having pnmary alkyl groups with 1 5 to 18 carbon atoms, and (C) one or more additional sulfur compounds selected from the group consisting of zinc dialky'ditl,ioud,Ld" ', copper d "~Iditlliu~.dlbdllldLt7 or nickel " "~ylditlliùudllJdl.. ' wherein the d "<yldithiùcdlLdllldLt: has alkyl groups with 2 to 18 carbon atoms, bis(dialkylthiu,.d,L,d,,,oyl)disulfide having an alkyl group with 2 to 18 10 carbon atoms, disulfide having an alkyl group with 2 to 18 carbon atoms, disulfide having an allyl group, an alkylallyl group or an allylalkyl group, with 6 to 18 carbon atoms, olefin sulfide, fish oil sulfide and whale oil sulfide, (D and E) boron containing succinimide, and (F) one or more metal d~:~.yel lts selected from the group consisting of calcium salicylate, 15 magnesium salicylate, calcium sulfonate, magnesium sulfonate and calcium phenate, wherein to the total weight of the ..u,, r ~ the molybdenum content from oxymolybdenum ditllk)~.dlL)dlll ' sulfide Is at 200 to 2,000 ppm (ratio by weight); the pho~,ul ,u,uus content from zinc " 'kyllitl ,iopho~JI IdL~: is at 0.02 to 0.15 ~/0 by weight; the sulfur content from the additional sulfur compounds is at 0.02 to 0.30 ~/0 by weight; the content of a metal detergent is at 1 to 10 ~/O by weight; and the boron content from boron containing succinimide is at 0.005 to 0.06 % by weight.
Methods to detenmine the amount of molybdenum, phosphorus, ~5 boron, nitrogen, and sulfur are well known in the art. For example molybdenum, phosphorus, and boron can all be dut~.",i"ed by inductively coupled plasma atomic emission spe,,Gu,,,,:L,y, JPI-5S-38-92. Nitrogen may be d~te.lll;"ed by the chemil~""i,.~scence method described in JIS K
2609 7. Sulfur may be dt:L~ ;lled by the method described in ASTM D
5453 which involves ~o".~. Li"g sulfur to sulfur dioxide, exciting the sulfur dioxide with ultraviolet light and measuring the amount of fluorescent emission produced.
WO96/0690S 9$~7~ 11~ C~
Detailed Description As the lubricant b~ c~si~ck to be used in the lubricant cu",,uu:,;Liu, of the present invention, use may be made of those base oils cw, ~.,. ,t;ona:'y used, for example, mineral oils and synthetic oils, without S any specific limitation.
Thus suitable minerai oils include those made from raffinate produced by solvent purification of a lubricant raw material with an aromatic extraction solvent such as phenol and furfural, hyd,uye,,dLiùn plu~,~,s3ûil oils by hyd~ugendt;un plUUt:aS;~I9 with a hydlug~dliun catalyst such as cobalt and moiybdenum on the carner silica-alumina, or mineral oils such as lubricant distillate produced by wax isu~ d~dLiùll~ for example, 60 Neutral Oil, 100 Neutral Oil, 150 Neutrai Oil, 300 Neutral Oil, 500 Neutrai Oil, and Bright Stock.
cly, suitable synthetic oils include, for example, poly~-olefin oligomers, polybutene, ~ 'ky~ "~e.le, polyol ester, polyglycol ester, dibasic acid ester, phOaph ' ester, silicon oil and the like. These may be used singly or in colllL,i, IdLiol) with two or more, or a mineral oil may be mixed with a synthetic oil for use.
The base oil to be used in the lubricant cu,,,,uoaiLiun of the present invention has a viscosity at 100~C in the range of 3 to 20 cSt.
Particularly"u,.,'~ ".,e is given to a h~llugt:lldLiùn decu,,,~,uaiLiun oil and a wax isu""~ dLio" oil, with 3 ~/O by weight or less of aromatic co,,,,uùllellta~ 50 ppm or less of sulfur ~,ulll,uollellb and 50 ppm or less of nitrogen co~uùllellLa~
~5 As the oxymolybdenum dilll;u~,dlbdlll ~ sulfide to be blended with the lubricant cu, Il,uOa;Liu U of the present invention, use is made of a compound It:~.rc:se, ,' . by the general formula (1):
S x X X S 3 R
N_C_S _Mo Mo _S _C _N
\ /
RZ X F~4 ( 1 ) WO96~06901 2~9S~ 6- r~ll~3s~
wherein R1 R2 R3 and R4 may be the same or different each aelllLill9 an alkyl group with 8 to 18 carbon atoms; and x l~ a~lltS S
orO.
The alkyl group with 8 to 18 carbon atoms I~ a~ d by R1 R2 R3 and R4 in the general formula (1) may be linear or branched. For the lubricant of the present invention the carbon number of the alkyl group a:ll by R1 R2 R3andR4ismostpreferably8to13. Specific exampiesofthealkylgroup I~ by R1 R2 R3andR4 include 2-ethylhexyl octyl group nonyl group decyl group undecyl group I0 dodecyl group tridecyl group tetradecyl group pe"Lddecyl group hexadecyl group ht:~,tdJecyl group and octadecyl group.
In the lubricant ~ Clll~ O_;tiJII of the present invention one species of oxy,,,olyudenum dalliOCdlbdll sulfide may be used or two or more species thereof may be used in cc.llLi,ldliol,. Furthemmore I 5 oxymolybdenum lill liUCdl Ldl I ' sulfide is blended so that the u loly.,cle".lm content from oxymolybdenum ditl liU~.dl Udl l l ' sulfide in thefinished lubricant is from about 200 to about 2 000 ppm (ratio by weight) preferably 300 to 800 ppm (ratio by weight) to the total weight of the co",~,ositiùn. When ù~ y,,,ùiybde,,.lm liIh;u~.dlLdlllat~ sulfide is blended in an amount such that the "lolyude".lm content from u~",u yLde"um diLlliu dlbdll sulfide is below 200 ppm (ratio by weight) to the total weight of the cOIlluuailiull the effect of improving the mction properties (low friction) is not sdliard~.Iul Iy exhibited; and when oxymolybdenum ditlliocdludllldltl sulfide is blended at an amount such that the ""~Iybde",Jm contentfrom oxymolybdenum dillliu dlbdlll sulfide is above 2 000 ppm (ratio by weight) to the total weight of the CO",,.~O:,ii;ul"
the improvement of the effect is not observed in proportion to the amount and sludge is likely to be caused. Oxymoiybdenum ditlliul dludllldLt:
sulfides are well known and available CO"""t:~ Iy. Rey, :a~ ,Ldli./e methods for their ~ .IdldliUII are described in US 4 098 705.
As the zinc dialkyl lithiu~hOaul IdLtl to be blended with the lubricant co",~osiliun of the present invention use is made of a compound IC~ aellL~:d by the general fommula (2):
~ 21 95~ 75 Wo 96/0690~ ~ ~ 7 ~ P~ ~ S
Rs _ O ISl S o--R7 /P--S--Zn--S--P
Rs_O O--Rs wherein R5, R6, R7 and R8 may be the same or different, each re~,,eaelllil,g a primary alkyl group with 1 to 18 carbon atoms. They may 5 be prepared in ac.,o, ian-,e with known techniques by first fomming a dihydrocarbyl iitlliOphoaullo,i., acid (DDPA), usually by reaction of one or more primary alcohol with P2Ss and then neutralizing the fommed DDPA
with a zinc compound. To make the zinc salt, any basic or neutral zinc compound could be used but the oxides, hydroxides and cd,L,on..t~. are 10 most generally employed. Commercial additives frequently contain an excess of zinc due to use of an excess of the basic zinc compound in the neutralization reaction. In order to obtain oil solubility, the total number of carbon atoms in the alcohols reacted to form the .,i;hiu,uhùs~,l,o,ic acid will generally be about 5 or greater.
The primary alkyl group le~,rus~ by R5, R6, R7 and R8 in the general formula (2), may be in a linear chain or in a branched chain, including for example rnethyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl sroup, dodecyl group, tridecyl group, tetradecyl 20 group, pentadecyl group, hexadecyl group, he~Jtddecyi group and octadecyl group. In the lubricant COIIIuuaitiull of the present invention, preferably, use may be made of zinc dialkylditl,;u,uhoayhdle having a primary alkyl group with 3 to 12 carbon atoms.
In the lubricant cul "poSiliuil in ac"u, id"-,e with the present 25 invention,zinc i 'k~lditll,ophosul, ' isblendedsothatthepl,uapho,uus content from zinc diaiky'dilhiophoa,uhdle is at û.û2 to û.15 ~/0 by weight, preferably û.04 to 0.12 ~J0 by weight to the total weight of the cu~l~poslliun~
When zinc dialkyk~;;hiuulloaphdle is blended at an amount such that the phuauhuluus contentfrom zinc iidlkyluitllluullosplldle is below 0.02 ~/0 by 30 weight to the total weight of the uullluOailiul1, the resulting collluoailiuncannot get c~ f .I. ,ry wear p~:~ rul ll ldl lce or cannot get a small coeffficient W096/0690.~ 2l95~5 -8- ~ c of friction ~dliardululy under the operation cu, Iditiulla of high oil temperature and low-speed rotation; and when zinc dialkyldiLl,iu~llG ,~uhdL~ is blended at an amount such that the uhua,uholu.ls content from zinc, " " yl~lithiopho:,~ul IdLt: is above 0.15 ~/0 by 5 weight to the total weight of the CC~ uO ,iLiul " the improvement of the effect is not observed in proportion to the amount.
The additional sulfur compound required for the present invention is selected from any of the sulfur compounds that efficiently decu,,,~ose peroxides. Without intending to be bound by any theory, the extended 10 fuel economy pe, ru" "ance of the present invention may be attributable to suppressed consumption ofthe oxy",olyL,del,um ' ''liu~,dlLdllldLt: sulfide and the zinc dialkyWithiuuhu:,ul IdLt: because the sulfur compounds effficiently ;iecu,"uuae peroxides.
As the " 7<yldiLI lioUdlLldlll ' salt to be blended in the lubricant 1~ culil~Jùsiliun of the present invention, use is made of a compound ,":ae"~d by the general formula (3) R9 S llS
o,N - c - s - M--S--C N~R12 wherein M ,t:~ ,u_~.lta zinc, copper or nickel; R9, R10, R11 and R12 may be the same or different, each r~:,u~t:S~"~;"g an alkyl group with 2 to 18 ZO carbon atoms. Metal salts of ~ Witllio~,dlbdllli~. acid are well known and readily available. Processes for their synthesis are described in US
4,623,473 and 4,740,322.
The alkyl group of 2-18 carbon atoms ll:~u~se~Le:d by R9, R10, R1 1 and R12 in the general fommula (3) may be linear or branched, Z~ inciuding for example ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pe"Ladecyl group, hexadecyl group, he~Lddecyl group and octadecyl group.
~ 9S~ 75 . .
WO 96/06904 9 _ ~ O s r~
As the bis(dialkylll,iu-,d,bd~"u,rl)disulfide to be blended in the lubricant cuu,~,ùsiiio n of the present invention, use may be made of a ~ compound le~luae.lled by the general formula (4):
R13\ S 11 ,RI5 N--C--S--S--C--N
R14/ ~Rl6 S wherein R13 R14~ R15 and R16 may be the same or different, each leuleSelltill9 an alkyl group with 2 to 18 carbon atoms The alkyl group of 2-8 carbon atoms l~,ulu__.lled by R13, R14, R15 and R16 in the general fommula (4) may be linear or branched, including for example ethyl group, propyi group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pe"td.iecyl group, hexadecyl group, he~Jtddecyl group and octadecyl group.
As the disulfide to be blended in the lubricant Culll~JùaitiOIl of the present invention, use is made of a compound le~Jltaa~ by the general fommula (5):
R17~s_R18 (5) wherein R17 and R18 may be the same or different, each re,u~ ti"9 an alkyl group with 2 to 18 carbon atoms or an allyl group.
an alkylallyl group or an allylalkyl group, with 6 to 18 carbon atoms. The alkyl group of 2-8 carbon atoms lelJIesellled by R17 and R18 in the general fommula (5) may be linear or branched, including foc example ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pe~llddd~ l group, hexadecyl group, heptadecyl group and octadecyl group; the allyl group, the alkylallyl group or the allylalkyl group, having 6 to 18 carbon atoms and being ~e~ __. ' by R17 and R18, includes for example phenyl group, benzyl group, phenetyl group, methylbenzyl group, diphenylmethyl group and the like.
gS4~5 W0 9610690~ 0 - . ~ b7~
Olefin suifide, fish oil sulfide and whale oil sulfide, to be blended with the lubricant ~,ulll,uua;;iun of the present invention, should be olefin sulfide (polysulfide) being produced by sulfide p,u.,~ssi"g of polymers such as isobutylene and having a sulfur content of 25 to 40 ~/0 by weight, 5 fish oil sulfide and whale oii sulfide produced by p,u~,esai"g individually fish oil and whale oil in the same manner.
In the lubricant colll,uuailion of the present invention, the metal dialkyl iitl liUUdl bdl I Idk~ ,UI t:ael I ' ' by the general fommula (3), bis(dialkyl11,ioca,bd""~yl)disulfide It:~Jn:ar-llLed by the general fomlula (4),10 disulfide r-:,u,~sr-"t~d by the general fommula (5), olefin sulfide, fish oilsulfide and whale oil sulfide, may be used singly or in cu,l,L,i, IdLiUU of two or more thereof. These sulfur compounds may be blended so that the sulfur content derived from these added sulfur compounds is 0.02 to 0.30 O~D by weight. When these sulfur compounds are blended at an amount 15 such that the sulfur content from these added sulfur compounds is below 0.02 ~/0 by weight to the total weight of the ,,u,,,,uosiLiùn, the effect of sl ~ ' .;1 ~y friction decrease is insuffcient; when these sulfur compounds are blended at an amount such that the sulfur content from these sulfur compounds is above 0.30 ~/0 by weight to the total weight of the 90 uulll,uuait;OIl, the improvement of the effect cannot be brought about in p,u,uu~Liùn to the amount.
If desired, one or two or more metal d~t~. y~l ,ts selected from the group consisting of calcium salicylate, magnesium salicylate. calcium sulfonate, magnesium sulfonate, and calcium phenate may be blended ~5 with the lubricant ~,c~lll,u05iLiun of the present invention. These metal d~LI::ry~l ILa may be blended at 1 to 10 ~/O by weight to the total weight of the .,u,,,uùsiLiùm Vvhen these metal detergents are blended below 1 ~/0 by weight to the total weight of the cu" IpuaiLiul " the cleansing effect is u,~ ry, when these metal d~t~.y~l,ts are blended above 10 ~/O by 30 weight to the total weight of the Cul",uOaltiuil, the improvement of the effect cannot be observed in proportion to the amount, or rather, ash content may increase. Recoy"i~i"g that metal d~ ~.y~ comprise oil sl,a,uensiù,ls of neutral and overbased metal salts of organic acids, the 219S~75 ~ - r WO 9610690~1 . ..,. ~f ~ ~ ~ P~
treat rates recited cu, ~ uond to treat rates of from about 0.5 to 8 weight percent active ingredient.
Metal-containing or ash-fomming d~t~ryer,ts generally comprise a polar head with a long hyd,u~llot,i~. tail, where the polar head is a metal 5 salt of an acidic organic compound. The salts may contain a substantially ~tùk,ll;w~ lliu amount of the metal in which case they are usually described as nonnal or neutral salts, and would typically have a total base number or TBN (as may be measured by JIS K2501) of from 0 to 80. It is possible to include large amounts of a metal base by reacting an excess 10 of a metal compound such as an oxide or hydroxide with an acidic gas such as carbon dioxide. The resulting oie.l,a:.,ad detergent comprises neutralized detergent as the outer layer of a metal base (e.g. carbonate) micelle. Such ov~.L,a~ed d~ .yt:l,ts may have a TBN of 150 or greater, and typically of from 250 to 450 or more.
Sulfonates may be prepared from sulfonic acids which are typically obtained by the s~l'' Idliun of alkyl s~hs'i~ t ' aromatic hJdlu~.dlLul,a such as those obtained from the Fld~liulldliùn of petroleum or by the alkylation of aromatic l.Jd, U~dlbUn:l The oil soluble s~ or alkaryl sulfonic acids may be neutralized with oxides, hydroxides, alkoxides, 20 I,dlborldt~s, udlLJuxy, ', sulfides, hydrosulfides, nitrates, borates and ethers of the alkali metal. The amount of metal compound is chosen . having regard to the desired TBN of the final product but typically ranges from about 100 to 220 wt % of that ~I~,i,,hiu,"~l, "y required.
Metal salts of alkyl phenols and sulfurized alkyl phenols are 25 prepared by reaction with an d,u~ulufJIidLe metal compound such as an oxide, hydroxide or alkoxide and overbased products may be obtained by methods well known in the art. Sulfurized alkyl phenols may be prepared by reacting an alkyl phenol with sulfur or a sulfur cu,,~ ,i"y compound such as hydrogen sulfide, sulfur ",ol10h ' '~ or su fur dihalide, to form 30 products which are generally mixtures of compounds in which 2 or more phenols are bridged by sulfur containing bridges.
Metal salts of carboxylic acids (including salicylic acids) may be prepared in a number of ways: for example, by adding a basic metal W096/0690~1 2~954~ 12- ~ s compound to a reaction mixture uu,, ,~ ,i, ,9 the carboxylic acid (which may be part of a mixture with another organic acid such as a sulfonic scid) or its metal salt and promoter, and removing free water from the reaction mixture to fonm an metal salt, then adding more basic metal S compound to the reaction mixture and removing free water from the reaction mixture. The carboxylate is then ov_.L,ased by introducing the acidic material such as carbon dioxide to the reaction mixture while removing water. This can be repeated untii a product of the desired TBN
is obtained.
The overbasing process is well known in the art and typically comprises reacting acidic material with a reaction mixture cu,,,,u,i~i,,g the organic acid or its metal salt, a metal compound. That acidic material may be a gas such as carbon dioxide or sulfur dioxide, or it may be boric acid. Processes for the p,e~dldliun of o./e.bdsed alkali metal sulfonates and phenates are described in EP-A-266034. A process suitable for overbased sodium sl~'h Idlt:~ is described in EP-A-235929. A process for making overbased salicylates is described in EP-A-351052.
The overbased metal ci~t~ "ts can be borated. The boron may be introduced by using boric acid as the acidic material used in the 20 overbasing step. However an ' Il..ti-C is to borate the overbased product after fommation by reacting a boron compound with the overbased metal salt. Boron compounds include boron oxide, boron oxide hydrate, boron trioxide, boron trifluoride, boron tribromide, boron trichloride, boron acid such as boronic acid, boric acid, tetraboric acid and metaboric acid, 25 boron hydrides, boron amides and various esters of boron acids. Boric acid is preferred. Generally, the overbased metal salt may be reacted with a boron compound at from 50~C to 250~C, in the presence of a solvent such as mineral oil or xylene.
Conveniently, the lubricant cu, l ,,uu ~;~iuil of the present invention 30 contains an overbased metal detergent in an amount sufiicient to provide a total base value of the finished lubricant in the range from about 3 to about 10, more preferably from 4 to 7. The total base value can be ~ Z19s~7~ ' WO 96/0690~ -13 - r~ ''C . /~;
~ ~*
measured according to JIS K2501. The total base value can be adjusted preferably by selecting a metal detergent with an dU,UIU,UI idi~ base value.
. .
If desired, an ashiess d;;"uu,ad"l may be biended into the lubricant.
The ashless d;~uer~d"l collljulisds an oil solublizing poiymeric S hydlucdluoll backbone having functionai groups that are capable of assouidtillg with particles to be dispersed. Typically, the di~,~er~d"ts comprise amine, alcohol, amide, or ester polar moieties attached to the polymer backbone often via a bridging group. The ashless di~pCll::~dllL
may be, for example, selected from oil soluble salts, esters, amino-esters, 10 amides, imides, and, ,es of long chain llydlu~dluull 5llh mono and di~,dl UUAyliC acids or their di Ihy.il kies, LhiU~,dl UUAy' derivatives of long chain hyd~UUdlUU115, long chain aliphatic hydlu~,d,bons having a polyamine attached directly thereto, and Mannich cor,densdLiu"
products formed by condens;"g a long chain sllhctitll~~1 phenol with 15 fu~udl~ hyde and polyalkylene polyamine.
The oil soluble polymeric hydlul,dlbùll backbone is typically an olefin polymer, especially polymers co,,,,u,;~ a major molar amount (i.e.
greater than 50 mole %) of a C2 to C18 olefin (e.g., ethylene, propylene, butylene, isobutylene, pentene, octene-1, styrene), and typically a C2 to 20 Cs olefin. The oil soluble polymeric h~dlu~,dlLJull backbone may be a homopolymer (e.g. polyp,uu,~la.)e or polyisobutylene) or a copolymer of two or more of such olefins (e.g. cu,uOl~ a of ethylene and an alpha-olefin such as propylene and butylene or ~,u,uoly,,,_,:, of two different alpha-olefins). Other copolymers include those in which a minor molar '5 amount of the copolyme m~lullGII ,a,~, e.g., 1 to 10 mole ~/0, is a C3 to C22 non-conjugated diolefin (e.g., a copoly",ar of isobutylene and butadiene.
or a copolymer of ethylene, propylene and 1,4-hexadiene or 5-ethylidene-2- no, bu, "ene). One preferred class of olefin polymers is polybutenes and spe,,iril,..l,y polyisobutenes (PIB) or poly-n-butenes, such as may be 30 prepared by pcl~lue~ dLiùn of a C4 refinery stream.
The oil soluble polymeric hydlu~dlboll backbone will usually have number average molecular weight (Mn) within the range of from 300 to 20,000, conveniently 500 to 10,000, and usually 700 to 5,000.
~9~47S ~
W0 96/069W - i4 ~ /~. . 7~a Particularly useful olefin polymers for use in di~e,~dllt~ have Mc within the range of from 1500 to 3000. The Mc for such polymers can be detellllllled by several known techniques. A convenient method for such deLe u l liU dLiUI I is by gel pe", led LiUI I ul 11 Ul I IdLUy l dlJ h y which adui'i~
5 provides molecular weight distribution i"rul IlldLiUn, see W. W. Yau, J. J.
Kirkland and D. D. Bly, "Modem Size E-xclusion Liquid ChlullldLuyld~ully John Wiley and Sons, New York, 1979.
The oil soluble polymeric h~JluudlL1u~ backbone may be fu, n~Liùndli~e i to i, ,~,u, ,UUldle a functional group into the backbone of the lO polymer, or as one or more groups pendant from the polymer backbone.
The functional group typically will be polar and contain one or more hetero atoms such as P, O, S, N, halogen, or boron. It can be attached to a saturated hyJ, U-,dl LJUI I part of the oii soluble polymeric hydl Ul,dl LJUn backbone via s~ Ihstitution reactions or to an olefinic portion via addition or 15 cycload iitiu" reactions. AlLelll "~cly, the functional group can be ,ul,uuldteJ into the polymer in conjunction with oxidation or cleavage of the polymer chain end (e.g., as in u~u"u'ysis).
Useful fu, ILLiùridli~dliùn reactions include: halùge~ Liùll of the polymer at an olefinic bond and C~hspciupnt reaction of the lidlùgendled 20 polymerwith an etl-llc,li....:'J unsaturated functional compound; reaction of the polymer with an unsaturated functional compound by the "ene"
reaction absent hdluyelldLiun (e.g., maleation where the polymer is reacted with maleic acid or anhydride); reaction of the poiymer with at least one phenol group (this permits derivatization in a Mannich base-type 71; COIldell~dliOIi); reaction of the polymer with the full~.Liùlidli~ y compound by free radical addition using a free radical catalyst; reaction with a Illiul,dliJu.~ylic acid derivative; and reaction of the polymer by air oxidationmethods, ~IJ, ~ n, ul llul udl l lil ldLiul~, or ozonolysis.
The fiJ, lULiUi idG~ed oil soluble polymeric h~ Ul,dl bU~ I backbone is 30 then further derivatized with a nucleophilic reactant such as an amine.
amino-alcohol, alcohol, metal compound or mixture thereof to fomm a cullea,uùliui"g derivative. Useful amine compounds for derivatizing fi~"uLiul Idli~ed polymers compnse at least one amine and can comprise ~ 219s~7~S ' WO 96/0690-1 15 9 r- - P~, 1/ '/C . /~a .i. ~
one or more additional amine or other reactive or polar gnoups. These amines may be hydrocarbyl amines or may be u,c:dulll;,ldlllly hydrocarbyl amines in which the hydrocarbyl group includes other groups, e.g., hydroxy groups, alkoxy groups, amide groups, nitriles, i" ' ' ,e 5 groups, and the like. Particularly useful amine compounds include mono-and polyamines, e.g. polyalkylene and PO!Y~JAY "cylene poi!r~_."i"es of about 2 to 60, conveniently 2 to 40 (e.g., 3 to 20), total carbon atoms and about 1 to 12, conveniently 3 to 12, and 3 to 9 nitrogen atoms in the moleculë.
The fullr_Liùlidli~t:d oil soluble polymeric hydlu.,dluull ba.,kbo"~:a also may be derivatized with hydroxy compounds such as monohydric and polyhydric alcohols or with aromatic compounds such as phenols and naphthols.
A preferred group of ashless di~ ad~,'s includes those 15 5llhstitll~~ ~ with succinic anhydride groups and reacted with polyethylene amines ~e.g., l~l,dc:Ll,ylene p~ltd~ le), dlllill ' huL, such as trismethylold",i"u",.,Ll,d"e and optionally additional reactants such as alcohols and reactive metals e.g., pentaerythritol, and culllu;lldLiull~
thereof). Also useful are d i~ ladl,ts wherein a polyd",i"e is attached '0 directly to the backbone by the methods shown in US 3,275,554 and 3,565,804 where a halogen group on a hdlogen ' ' hydlu.,d,uù,, is displaced with various alkylene pu.y_."i"es.
Another class of ashless d;~"~ladllts uulll,uriaes Mannich base condcnsdliun products. Generally, these are prepared by co"uensi"g ~5 about one mole of an alkyl-s~ IhCtitl ltPd mono- or polyhydroxy benzene with about 1 to 2.5 moles of carbonyl compounds (e.g., fulllldWl~ e and pdl dfu""aldel ,yde) and about 0.5 to 2 moles polyalkylene polyamine as disclosed, for example, in US 3,442,808. Such Mannich coode, ladliol l products nnay include a long chain, high molecularweight hyu,u.,d,bon 30 (e.g., M,l of 1,500 or greater) on the benzene group or may be reacted with a compound r_Ul lLdil ,i"g such a hyrllu~,d,bùl " for example, polyalkenyl succinic anhydnde as shown in US 3.442,808.
, ~. . , 2Jgs4~5 ' ~
wos6/06sn~ - 16~ S
Theful~,liùl~ ' " ns,cie, i~/dt;Lcli;Ulla, andpost~ dt~ ts described in the following patents may also be adapted to fullr~ i;oudli~
and/or derivatize the preferred polymers descnbed above: US 3,275,554.
3,565,804, 3,442,808, 3,442,808, 3,087,936 and 3,254,025.
The u'i~ ,ad"l can be further post-treated by a variety of conventional post I", dilllCI Ua such as boration, as generally taught in US
3,087,936 and 3,254,025. This is readily a,_,_w,,~ .l,ed by treating an acyl nitrogen-containing di~,J6laell~I with a boron compound selected from the group consisting of boron oxide, boron haiides, boron acids and l O esters of boron acids, in an amount to provide from about 0.1 atomic proportion of boron for each mole of the acylated nitrogen .,ul, l~oaition to about 20 atomic p, up~JI liùns of boron for each atomic proportion of nitrogen of the acylated nitrogen ~,ulllr~Jua;ii.Jil. The boron, which appears be in the product as del "/dl dl~:r j boric acid poiymers (primarily (HB02)3), 1~ is believed to attach to the di~r,Jeladl~I imides and diimides as amine salts e.g., the IllI:IdbUl ' salt of the diimide. Boration is readily carried out by adding from about 0.05 to 4, e.g., 1 to 3 wt. % (based on the weight of acyl nitrogen compound) of a boron compound, preferably boric acid, usually as a slurry, to the acyl nUrogen compound and heating with stirring at from 135~ to 190~ C, e.g., 140~-170~ C, for from 1 to 5 hours followed by nitrogen stripping. r. " . Iy, the boron treatment can be can ied out by adding boric acid to a hot reaction mixture of the di"dliJu,~y'i~, acid material and amine whiie removing water.
When the d;~,r,Jt:~ad"I is a nitrogen containing diar,Jt:ladllI, the ratio 2~ of the number of boron atoms/the number of nitrogen atoms in the boron containing succinimide to be used in the lubricant COIll~ uailiun of the present invention is 0.05 to 1.5, preferably 0.1 to 0.8. If the ratio of the number of boron atoms/the number of nitrogen atoms is below 0.05, sdIiardl,Iuly improvement of friction properties (low friction) cannot be brought about; if the ratio of the number of boron atoms/the number of nitrogen atoms is above 1.5, friction properties are d~. iUldirr d.
In the lubricant culll,uOaiIiul, of the present invention, the boron containing succinimide should be blended at an amount such that the W0 96/0690~ ~ - 17 -~. ~.
boron content from boron uu, ,;"9 succinimide is at 0.005 to 0.06 ~/0 by weight, preferably 0.01 to 0.04 ~/0 by weight to the total weight of the cc""po .i~ion. When the boron containing succinimide is blended at an amount such that the boron content from boron containing succinimide is S below 0.005 ~/0 by weight to the total weight of the cc,."~,u~itiui), no " ' ' y improvement of friction properties (low friction) can be brought about; if the boron cc" lld;ll;l 19 succinimide is blended at an amount such that the boron content from boron containing succinimide is above 0.06 ~/0 by weight to the total weight of the ~,U~pOsit;ul), no i,,,,u,u~,l,c.ll of the eMect can be brought about in proportion to the amount.
In a range without departing from the scope of the present invention, various additives cu, ,~l_. " ) "y used for lubricants, for example, other friction modifiers, other metal du'~r ,t:"b, other wear preventing agents, dlLUA; idllt:~, viscosity modifiers, pour point de~,eas;"y agents, anti-foaming agents, nust ,cl-,l_.l .l., agents, and corrosion inhibitors, may be blended in the lubricant cu",~,os;i;un of the present invention.
Other friction modifiers include for example polyhydric alcohol 2D partial ester, amine, amide, sulfide ester and the like. Boration of friction modifiers is well known in the art and ,t~ ,e"t~ an " " ~c way to introduce boron into the lubricant.
Other metal detu,y~l lt~ include for example barium sulfonate, barium phenate and the like, which may be used generally at a ratio of '5 0.1 to 5 ~/O by weight.
Other wear preventing agents include for example lh;u~il ,os~,l Idlt:
metal salt, sulfur compound, ,uhu~ ihat~ ester, phosphite ester and the like, which may be used generally at a ratio of 0.05 to 5.0 % by weight.
Al ll;OA; idl ,ts include for example amine dl ll;UAk,idl ,ts such as ~ 30 alkylated diphenylamine, phenyl-a-naphthyiamine, and alkylated a-naphthylamine; and phenol a"liuxidc,r,la such as 2,6-di-t-butyl-4-methyl ~9~
W096/0690.1 C~ -18- .,111 931. I~a phenol and 4,4'-methylene-bis(2,6-di-t-butyl phenol), which may be used generally at a ratio of 0.05 to 4 ~/0 by weight.
Viscosity modifiers (aiso frequently called viscosity index improvers) include for example poly" luil ,a~., ylates, polyisobutylenes, 5 ethylene-propylene Cu,uu'y~llula, styrene-butadiene hydluyelldlud cupoly"~ a and the like, which may be used generally at a ratio of 0.5 to 35 ~/0 by weight.
Pour point de~ as;"g agents include for example polyalkylmethacrylate, ~,1 ,lu, i, Idtc:d paraffin-r,a~ Ihdl~:l ,e con.le"sed 10 product, alkylated polystyrene and the like.
Anti-foaming agents include for example dimethylpolysiloxane, ~ polyacrylic acid and the like.
Rust preventing agents include for example fatty acid, alkenyl succinate partial ester, fatty acid soap, alkylsulfonate salt, fatty acid 15 polyhydric alcohol ester, fatty acid amine, paraffn oxide, alkylpolyoxyethylene ether and the like.
Corrosion inhibitors include for example be, ,~ul, id~ule and b~"~ui" li~
20 Examples The present invention will now be explained in detail in examples.
but the invention is not limited to these examples.
Herein, the coeffcient of friction of the lubricant cu" ,,uositk,n was measured at a 50-Hz frequency, a 3 mm dl~ le, a 25-N load, a 25 temperature of 80~C and a testing period of 25 minutes, using a :l,;,UlU-~dLt: dynamic sliding friction tester (SRV friction tester).
The oxidation test by means of air cu":..;.,;"9 gaseous nitrogen oxides was carried out using a 150 ml test oil at a temperature of 1 30~C.
a nitrogen oxide level of 1 ~/0 by volume. a flow of 2 liters/hour, and a iO testing period of 8 hours.
~ 21 9~ 7~
W096/06901 ~ 19- ~ re .~, r ~ it,=
Examples 1 to 9 and Cu~ al ' ~u Examples 1 and 2 Examples 1 to 9 are lubricant c~lll,uO:~;Liùlla blended with (A) ox~",ùlyu ie"um iitlliuudli dllldle sulfide, (B) zinc diaik~,l iitl,iu~ul,u~,l,dle, (C) zinc dialkyi ~liUl,dliJdll , copper, lk~lui;l,iu,,d,ua,,, 5 bis(dialky;'hiùud,ua,,,ùyl)disulfide ordibenzyldisulfide, (D) calcium salicylate, and (E) boron culltaill;ng succinimide. Fullllellllule, Colll,Udl ~C Examples A and B are lubricant cU"~,UUsitiull . containing the culll~Jùnellts (A), (B), (D) and (E), without ~c",'..:.,i"g the Culll,ùollellL (C).
Individual uullluul-elltS of a type and an amount shown in Tabie 1 lo were blended with the base oil (100 Neutral Oil with a viscosity of 4.4 mm/s2 at 100~C) to prepare lubricant cu"")ositi~."~ cc."L..;.,i"g the cu,~,,uun6,~ts~ and the uuerri~,ie"l of friction i"""e.,i '~!y afterthe I~e,ua, ' ~ was measured, together.with the ~.oerfi~iel ,L of friction after the F;l-r- ' 15 were stored and oxidized in the presence of gaseous nitrogen oxides at 1 30~C for 8 hours. The results are shown in Table 1.
All the lubricant cu"., ' ns of Examples 1 to 9 all have good friction properties with low cueffi.,iel ~ts of friction. No change in the cu_rfi.,;_, hs of friction was observed even after the lubricant cu, "~JOsitiul ,~
were heated in the presence of gaseous nitrogen oxides at 130~C for 8 20 ' hours. Thus, it is indicated that these lubricant cu" "~ositiu"~ have good le~i~lance to oxidation with no change in the observed coerri-,ie~.s of fn'ction. Altematively, the lubricant coll,r " ,s of Cu~llJa~..:iii Examples A and B, without ~.U~ Itai~ ly the ~ uullelll (C), i.e., a sulfur compound, have low c4erri~,iel Its of friction i" ", . - " 'y after ~ll eudl dLio~ ~, 25 but have acquired higher coefri~,ienk~ of friction after the ,u~e,udldLiul ,~were heated and oxidized in the presence of gaseous nitrogen oxides at 130~C for 8 hours, indicating that their ,~ ' ' ,..e to oxidation is poor.
The lubricant ~.u",uo:.iliu" of the present invention has acquired good low abrasion property, through the blending of a lubricant base oil 30 with u.~y."ù.yL,der"~m dithiOUddJd~l sulfide, zinc dialkyi ' 'hiopl,usul, ', and a sulfur compound, each having a specific structure, a metal detergent and boron ~ Lail~ g succinimide. The cu",,uu ~iLiun can sustain good friction properties (low friction) while exhibiting resistance to WO 96/0690~1 - 20 - 1~
oxidation at higher temperatures in the presence of gaseous nitrogen oxides, and is preferably used as lubricants for intemal combustion engines, automatic Lld~ ion, snubbers, and power steering, preferably for intemal combustion engines in particular.
~ 2 ~ 4~5 W0 96/06904 l ~ Ja,; /~a -o Om o, Q ~1 ~D o ~ '~ ~
~ 0 <D O O ~ ~ ~ ~
o - o - ~ ~ o o~
~ o - - ~ o~ o o CD o O ~ ~~ O o 1~ ,o o --~ -- u co O O
;:
o -- '~ o ~
~ o o u~ o. l - 0 CD o O ~ O~ ~ O
o p~ z~
ae 2 - ~
~ 3 ~--~.,~, _ _ E ae ~ D
E Q ae ae ae 3 ~ ~x~ ~ . ~
C~ Cl C~ . 3 c ~ ~ ~ c~
~ ~ r~ ~ .~ : O . o ~ ~
E E ~ E E
O O , s 2 b .~ ~ :~ ~ L, ~ ~ CL cn 0 U7 U~ ~ m ~ z
Claims (10)
1. A lubricant composition comprising a major amount of an oil of lubricating viscosity having added thereto a minor amount of additives comprising (A) oxymolybdenum dithiocarbamate sulfide having alkyl groups with 8 to 18 carbon atoms, (B) zinc dialkyldithiophosphate having primary alkyl groups with 1 to 18 carbon atoms, (C) one or more additional peroxide decomposing sulfur compounds, (D) an ashless dispersant, and (E) a boron containing additive wherein to the total weight of the composition, the molybdenum content from oxymolybdenum dithiocarbamate sulfide is at 200 to 2,000 ppm (ratio by weight); the phosphorous content from zinc dialkyldithiophosphate is from 0.02 to 0.15% by weight; the sulfur content from the additional sulfur compounds is from 0.02 to 0.30 % by weight, and the boron content is from 0.005 to 0.06 %
by weight.
by weight.
2. The lubricant of claim 1 wherein the one or more additional peroxide decomposing sulfur compounds is selected from the group consisting of zinc dialkyldithiocarbamate, copper dialkyldithiocarbamate or nickel dialkyldithiocarbamate wherein the dialkyldithiocarbamate has alkyl groups with 2 to 18 carbon atoms, bis(dialkylthiocarbamoyl)disulfide having alkyl groups with 2 to 18 carbon atoms, disulfide having alkyl groups, allyl groups, alkylallyl groups, or an allylalkyl groups, with 6 to 18 carbon atoms, olefin sulfide, fish oil sulfide, whale oil sulfide, and mixtures of any of the foregoing.
3. The lubricant of claim 1 further comprising (F) from 1 to 10 % by weight of one or more metal detergents selected from the group consisting of calcium salicylate, magnesium salicylate, calcium sulfonate, magnesium sulfonate and calcium phenate.
4. The lubricant composition of claim 1 wherein the ashless dispersant and boron containing additive are a borated polyalkenyl succinimide.
5. A lubricant composition comprising a major amount of a lubricant base oil, and a minor amount of additives comprising (A) oxymolybdenum dithiocarbamate sulfide having alkyl groups with 8 to 18 carbon atoms, (B) zinc dialkyldithiophosphate having primary alkysl group with 1 to 18 carbon atoms, and (C) one or more additional sulfur components selected from the group consisting of zinc dialkyldithiocarbamate, copper dialkyldithiocarbamate or nickel dialkyldithiocarbamate, having alkyl groups with 2 to 18 carbon atoms, bis(dialkylthiocarbamoyl)disulfide having alkyls group with 2 to 18 carbon atoms, disulfide having alkyl groups, allyl groups, alkylallyl groups or allylalkyl groups, with 6 to 18 carbon atoms, olefin sulfide, fish oil sulfide and whale oil sulfide, and (D& E ) boron containing succinimide, (F) one or more metal detergents selected from the group consisting of calcium salicylate, magnesium salicylate, calcium sulfonate, magnesium sulfonate and calcium phenate, wherein to the total weight of the composition, the molybdenum content from oxymolybdenum dithiocarbamate sulfide is from 200 to 2,000 ppm (ratio by weight); the phosphorous content from zinc dialkyldithiophosphate is from 0.02 to 0.15 % by weight; the sulfur content from sulfur compounds is from 0.02 to 0.30% by weight; the content of a metal detergent is from 1 to 10% by weight; and the boron content from boron containing succinimide is from 0.005 to 0.06 % by weight.
6. The composition of claim 2 wherein the oxymolybdenum dithiocarbamate is of the formula wherein R1, R2, R3 and R4 may be the same or different, each representing an alkyl group with 8 to 13 carbon atoms and X represents S or O.
7. The composition of claim 2 wherein the zinc dialkyldithiophosphate has primary alkyl groups with 3 to 12 carbon atoms.
8. The composition of claim 3 wherein the ratio of the number of boron atoms to the number of nitrogen atoms in the boron containing succinimide is 0.05 to 1.5.
9. The composition of claim 1 wherein the additional sulfur containing compound is dibenzyldisulfide.
10. The composition of claim 3 wherein the metal detergent is calcium salycilate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6/232281 | 1994-09-01 | ||
| JP23228194 | 1994-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2195475A1 true CA2195475A1 (en) | 1996-03-07 |
Family
ID=16936774
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002195475A Abandoned CA2195475A1 (en) | 1994-09-01 | 1995-08-31 | Lubricants with sustained fuel economy performance |
| CA002157425A Abandoned CA2157425A1 (en) | 1994-09-01 | 1995-09-01 | Lubricant composition |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002157425A Abandoned CA2157425A1 (en) | 1994-09-01 | 1995-09-01 | Lubricant composition |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0778876A1 (en) |
| AU (1) | AU3230695A (en) |
| CA (2) | CA2195475A1 (en) |
| WO (1) | WO1996006904A1 (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6063741A (en) * | 1994-09-05 | 2000-05-16 | Japan Energy Corporation | Engine oil composition |
| JP2971748B2 (en) * | 1994-09-05 | 1999-11-08 | 株式会社ジャパンエナジー | Engine oil composition |
| JPH08283762A (en) * | 1995-04-14 | 1996-10-29 | Tonen Corp | Lubricating oil composition |
| US6855675B1 (en) | 1995-05-24 | 2005-02-15 | Tonengeneral Sekiyu K.K. | Lubricating oil composition |
| EP0847435A4 (en) * | 1995-05-24 | 1999-06-23 | Exxon Research Engineering Co | Lubricating oil composition |
| WO1997008280A1 (en) * | 1995-08-30 | 1997-03-06 | Tonen Corporation | Lubricating oil composition |
| JP3556355B2 (en) * | 1995-10-11 | 2004-08-18 | 東燃ゼネラル石油株式会社 | Lubricating oil composition |
| JP3497952B2 (en) * | 1996-08-02 | 2004-02-16 | 東燃ゼネラル石油株式会社 | Lubricating oil composition |
| GB9624441D0 (en) * | 1996-11-25 | 1997-01-15 | Exxon Research Engineering Co | Fuel economy engine oil composition |
| CA2251418C (en) * | 1997-10-30 | 2007-08-14 | The Lubrizol Corporation | A method to improve cu corrosion performance of mo-dtc and active sulfur by adding sunflower oil |
| JP4641567B2 (en) | 1997-10-30 | 2011-03-02 | ザ ルブリゾル コーポレイション | Method to improve copper corrosion performance of molybdenum dithiocarbamate and active sulfur by adding sunflower oil |
| US5972853A (en) * | 1997-11-12 | 1999-10-26 | Exxon Chemical Patents Inc. | Wear control with dispersants employing poly alpha-olefin polymers |
| US6143701A (en) * | 1998-03-13 | 2000-11-07 | Exxon Chemical Patents Inc. | Lubricating oil having improved fuel economy retention properties |
| JP5057603B2 (en) * | 1998-05-01 | 2012-10-24 | 昭和シェル石油株式会社 | Lubricating oil composition for internal combustion engines |
| US6569818B2 (en) * | 2000-06-02 | 2003-05-27 | Chevron Oronite Company, Llc | Lubricating oil composition |
| US6528461B1 (en) * | 2000-11-28 | 2003-03-04 | Bank Of America, N.A. | Lubricant containing molybdenum and polymeric dispersant |
| EP1310549B1 (en) * | 2001-11-09 | 2006-05-31 | Infineum International Limited | Boron containing lubricating oil compositions with low sulfur and phosphorus content |
| US7026273B2 (en) | 2001-11-09 | 2006-04-11 | Infineum International Limited | Lubricating oil compositions |
| EP1329496A1 (en) * | 2002-01-14 | 2003-07-23 | Infineum International Limited | Lubricating oil compositions with low sulfur and phosphorous content |
| US6777378B2 (en) | 2002-02-15 | 2004-08-17 | The Lubrizol Corporation | Molybdenum, sulfur and boron containing lubricating oil composition |
| EP1632554B1 (en) * | 2004-09-07 | 2011-08-24 | Infineum International Limited | Lubricating oil composition |
| US8361940B2 (en) | 2006-09-26 | 2013-01-29 | Chevron Japan Ltd. | Low sulfated ash, low sulfur, low phosphorus, low zinc lubricating oil composition |
| US8586516B2 (en) | 2007-01-19 | 2013-11-19 | Afton Chemical Corporation | High TBN / low phosphorus economic STUO lubricants |
| US9951290B2 (en) | 2016-03-31 | 2018-04-24 | Exxonmobil Research And Engineering Company | Lubricant compositions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59122597A (en) * | 1982-11-30 | 1984-07-16 | Honda Motor Co Ltd | Lubricating oil composition |
| US4648985A (en) * | 1984-11-15 | 1987-03-10 | The Whitmore Manufacturing Company | Extreme pressure additives for lubricants |
| US4812246A (en) * | 1987-03-12 | 1989-03-14 | Idemitsu Kosan Co., Ltd. | Base oil for lubricating oil and lubricating oil composition containing said base oil |
| JP2911668B2 (en) * | 1991-12-12 | 1999-06-23 | 出光興産株式会社 | Engine oil composition |
| EP0588561B1 (en) * | 1992-09-14 | 1998-12-02 | Oronite Japan Limited | Low phosphorous engine oil compositions and additive compositions |
| EP0609623B1 (en) * | 1992-12-21 | 1999-03-03 | Oronite Japan Limited | Low phosphorous engine oil compositions and additive compositions |
| JP3613530B2 (en) * | 1993-05-27 | 2005-01-26 | 東燃ゼネラル石油株式会社 | Lubricating oil composition |
-
1995
- 1995-08-31 EP EP95928596A patent/EP0778876A1/en not_active Withdrawn
- 1995-08-31 WO PCT/IB1995/000725 patent/WO1996006904A1/en not_active Application Discontinuation
- 1995-08-31 AU AU32306/95A patent/AU3230695A/en not_active Abandoned
- 1995-08-31 CA CA002195475A patent/CA2195475A1/en not_active Abandoned
- 1995-09-01 CA CA002157425A patent/CA2157425A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU3230695A (en) | 1996-03-22 |
| WO1996006904A1 (en) | 1996-03-07 |
| EP0778876A1 (en) | 1997-06-18 |
| CA2157425A1 (en) | 1996-03-02 |
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