US3764534A - New lubricating compositions - Google Patents
New lubricating compositions Download PDFInfo
- Publication number
- US3764534A US3764534A US00115811A US3764534DA US3764534A US 3764534 A US3764534 A US 3764534A US 00115811 A US00115811 A US 00115811A US 3764534D A US3764534D A US 3764534DA US 3764534 A US3764534 A US 3764534A
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- US
- United States
- Prior art keywords
- sulfur
- oxygen
- carbon atoms
- hydrocarbon radical
- lubricating composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000011593 sulfur Chemical group 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 239000011701 zinc Substances 0.000 claims abstract description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 10
- 239000010687 lubricating oil Substances 0.000 claims abstract description 7
- 239000002199 base oil Substances 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 abstract description 16
- 239000001301 oxygen Chemical group 0.000 abstract description 16
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 12
- 229930195733 hydrocarbon Natural products 0.000 abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- 230000003647 oxidation Effects 0.000 abstract description 9
- 238000007254 oxidation reaction Methods 0.000 abstract description 9
- 125000004429 atom Chemical group 0.000 abstract description 8
- 125000005842 heteroatom Chemical group 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 229910052757 nitrogen Chemical group 0.000 abstract description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052793 cadmium Inorganic materials 0.000 abstract description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052718 tin Inorganic materials 0.000 abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 abstract description 4
- 229910052787 antimony Inorganic materials 0.000 abstract description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052797 bismuth Inorganic materials 0.000 abstract description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003624 transition metals Chemical class 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 125000005594 diketone group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 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 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910000464 lead oxide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- -1 methoxy, ethoxy, propoxy, methylthio, ethylthio, acetyl Chemical group 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- 238000005476 soldering Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- OCHIDBMJEFPMFG-UHFFFAOYSA-N dithiiran-3-one Chemical compound O=C1SS1 OCHIDBMJEFPMFG-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 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 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
Classifications
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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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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- 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
- C10N2010/02—Groups 1 or 11
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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
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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
- C10N2010/06—Groups 3 or 13
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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
- C10N2010/08—Groups 4 or 14
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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
- C10N2010/10—Groups 5 or 15
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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
- C10N2010/12—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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
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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
- C10N2010/16—Groups 8, 9, or 10
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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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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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
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
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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
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
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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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- ABSTRACT A lubricating composition
- M is selected from the transition metals and zinc, cadmium, tin, lead, antimony and bismuth;
- n is the oxidation degree of M,
- R and R are each a monovalent hydrocarbon radical having one to 20 carbon atoms and 0 to 3 heteroatoms selected from the group consisting of halogen, oxygen, sulfur and nitrogen;
- Y is selected from the hydrogen atom and the radicals R, R'O, R'S and R'CO in which R is a hydrocarbon radical of one to 20 carbon atoms; Y and R or R may form a divalent hydrocarbon radical containing one to 20 carbon atoms and 0-3 heteroatoms selected from oxygen, sulfur and nitrogen; and each atom Z is oxygen or sulfur, at least one of the Z
- a known technique for improving the stability of lubricants and particularly motor oils-to oxidation consists of adding antioxidants thereto, said antioxidants being usually zinc dithiophosphates, dithiocarbamates, phenols or amines.
- thioorganometallic complexes hereafter defined have a high antioxidant activity, even at high temperature and in the presence of metals at high concentrations. These compounds may be used as well with base oils of petroleum origin as with synthetic base oils. They give good anti-wear and extreme pressure properties to the lubricating oils to which they are added.
- the lubricating compositions of this invention contain at least one thioorganic complex of the formula:
- thioorganometallic complexes are based on the element M which may be tin, antimony, lead, bismuth, zinc, cadmium or a transition metal element, for example chromium, manganese, iron, cobalt, nickel or copper, said element M, at the oxidation degree n, being linked with n coordinates, either identical or different, as hereinafter defined:
- R and R are each a monovalent radical which may be a hydrocarbon radical, for example an aliphatic, alicyclic or aromatic radical, or a haloor nitro-derivative thereof. They may contain 1 to 3 heteroatoms such as oxygen, sulfur or nitrogen. They usually contain one to 20 carbon atoms.
- Y is a hydrogen atom or a radical R, R'-O-, R'-S or R-CO- in which R is a monovalent hydrocarbon radical of, for example, 1 to 20 carbon atoms.
- Y and R or R may form a divalent hydrocarbon radical of one to 20 carbon atoms with to 3 oxygen, sulfur or nitrogen atoms.
- Each atom Z may be oxygen or sulfur, provided that at least one Z is sulfur in at least one of the coordinates.
- Each coordinate may have twomesomeric forms each having a negative charge:
- decyl phenyl, benzyl, methoxy, ethoxy, propoxy, methylthio, ethylthio, acetyl, propionyl, phenethyl, cyclopentyl, cyclohexyl and cycloheptyl.
- the thioorganic complexes may be manufactured according to known methods, e.g., U. S. patent 3,1 84,410, especially at Column 2, lines 6-7 and 51-53 pertaining to molybdenum complexes, as well as the Bulletin of the Chemical Society of Japan, Volume 40, 2819-2822 (1967).
- B diketones can be manufactured from the corresponding B diketones.
- the desired B diketones may be manufactured by any convenient method, for example by reacting an ester with a monoketone.
- the Y group is not hydrogen, it may be directly linked to the B diketone or after that a thiorganic complex has been formed with it or one of its sulfur derivatives.
- a sodium salt of a B diketone may be reacted with an alkyl halide to obtain an alkyl group represen-- tative of Y.
- the synthesis of the thioorganic complexes which are used in this invention comprises the step of sulfurizing the available or manufactured B diketone.
- This sulfurization is carried out according to any known method.
- Hydrogen sulfide may be used, for example, as the sulfurizing agent, either in acidic medium or not, optionally in a solvent.
- This sulfurization may be carried out in the presence of a salt of the desired metal. In that case there is obtained the desired thioorganic complex or a mixture of complexes of the given formula.
- the sulfurization is carried out without a metal salt, there is obtained, in some cases, a monothioketone or a dithioketone, or a mixture of both, or a mixture of one or two of them with the starting B diketone. It is sufficient as a rule, to contact the desired salt of metal with the ketones or their mixtures to obtain a thioorganic complex or a mixture of thioorganic complexes of the given formula.
- the present invention applies to all types of base oils, for example those obtained by extracting petroleum fractions with solvents or by any other refining or synthesis process.
- the thioorganic complexes are added to the base oils in low proportions, for example from 0.05 to 5 percent by weight and preferably from 0.2 to 2 percent by weight.
- the anti-wear and extreme-pressure properties are related to the power of these complexes to adhere on the metal surfaces, which results in a protection of the latter.
- M is a metal in the divalent state selected from the group consisting of the transition metals, zinc. cadmium, tin and lead; )1 is 2; R and R when taken individually are each selected from the group consisting of a monovalent hydrocarbon radical of one to 20 carbon atoms, a halohydrocarbon radical of one to 20 carbon atoms and a methoxy phenyl radical; Y when taken individually is selected from the group consisting of the hydrogen atom and the radicals R, R'O, RS and RCO 10 in which R is a hydrocarbon radical of one to 20 car- TABLE III Amount, Absorbed Example percent oxygen, number Oil Additive b.w. moles/liter 9 200 neutral solvent (zarzaitine) f CS 0.15 0.12
- a lubricating composition comprising a lubricating oil and from 0.05 to 5 percent by weight with respect to the oil of at least one thioorganometallic complex of the general formula:
- each atom Z is oxygen or sulfur, providing that at least one of the Z atoms of the complex is sulfur.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7006455A FR2077906A1 (enrdf_load_html_response) | 1970-02-23 | 1970-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3764534A true US3764534A (en) | 1973-10-09 |
Family
ID=9051138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00115811A Expired - Lifetime US3764534A (en) | 1970-02-23 | 1971-02-16 | New lubricating compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3764534A (enrdf_load_html_response) |
| BE (1) | BE763238A (enrdf_load_html_response) |
| DE (1) | DE2107577A1 (enrdf_load_html_response) |
| FR (1) | FR2077906A1 (enrdf_load_html_response) |
| GB (1) | GB1339056A (enrdf_load_html_response) |
| NL (1) | NL7102412A (enrdf_load_html_response) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200546A (en) * | 1979-01-08 | 1980-04-29 | Mobil Oil Corporation | Metal salt treated sulfurized olefins and organic compositions containing same |
| US4226733A (en) * | 1978-11-17 | 1980-10-07 | Mobil Oil Corporation | Lubricant compositions stabilized against ultra-violet degradation |
| US4397749A (en) * | 1982-01-29 | 1983-08-09 | Chevron Research Company | Oil-soluble metal thiolate-succinimide complexes |
| US4427560A (en) | 1981-12-10 | 1984-01-24 | Union Oil Company Of California | Anti-oxidation and corrosion inhibitors for boron-containing lubricants |
| US4867892A (en) * | 1987-12-28 | 1989-09-19 | Exxon Research And Engineering Company | Antiwear additives for lubricating oils |
| US20060258549A1 (en) * | 2005-05-13 | 2006-11-16 | Habeeb Jacob J | Catalytic antioxidants |
| US20070277431A1 (en) * | 2006-05-30 | 2007-12-06 | Kazushige Ohno | Additive for engine oil, engine oil, and exhaust gas purifying method |
| US20080076687A1 (en) * | 2006-09-22 | 2008-03-27 | Habeeb Jacob J | Catalytic antioxidants |
| US20090048130A1 (en) * | 2007-08-17 | 2009-02-19 | Habeeb Jacob J | Catalytic antioxidants |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7608842A (nl) * | 1975-08-15 | 1977-02-17 | Mobil Oil Corp | Werkwijze ter bereiding van smeermiddelen. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2305627A (en) * | 1939-05-24 | 1942-12-22 | Lubri Zol Dev Corp | Lubricating oil |
| US3184410A (en) * | 1963-08-20 | 1965-05-18 | British Petroleum Co | Molybdenum compounds and lubricating compositions containing them |
-
1970
- 1970-02-23 FR FR7006455A patent/FR2077906A1/fr not_active Withdrawn
-
1971
- 1971-02-16 US US00115811A patent/US3764534A/en not_active Expired - Lifetime
- 1971-02-17 DE DE19712107577 patent/DE2107577A1/de active Pending
- 1971-02-22 BE BE763238A patent/BE763238A/xx unknown
- 1971-02-23 NL NL7102412A patent/NL7102412A/xx unknown
- 1971-04-19 GB GB2221371A patent/GB1339056A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2305627A (en) * | 1939-05-24 | 1942-12-22 | Lubri Zol Dev Corp | Lubricating oil |
| US3184410A (en) * | 1963-08-20 | 1965-05-18 | British Petroleum Co | Molybdenum compounds and lubricating compositions containing them |
Non-Patent Citations (1)
| Title |
|---|
| Martell et al. Chemistry of the Metal Chelate Compounds Prentice Hall 1956 pages 168 169. * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226733A (en) * | 1978-11-17 | 1980-10-07 | Mobil Oil Corporation | Lubricant compositions stabilized against ultra-violet degradation |
| US4200546A (en) * | 1979-01-08 | 1980-04-29 | Mobil Oil Corporation | Metal salt treated sulfurized olefins and organic compositions containing same |
| US4427560A (en) | 1981-12-10 | 1984-01-24 | Union Oil Company Of California | Anti-oxidation and corrosion inhibitors for boron-containing lubricants |
| US4397749A (en) * | 1982-01-29 | 1983-08-09 | Chevron Research Company | Oil-soluble metal thiolate-succinimide complexes |
| US4867892A (en) * | 1987-12-28 | 1989-09-19 | Exxon Research And Engineering Company | Antiwear additives for lubricating oils |
| US20060258549A1 (en) * | 2005-05-13 | 2006-11-16 | Habeeb Jacob J | Catalytic antioxidants |
| US8030257B2 (en) | 2005-05-13 | 2011-10-04 | Exxonmobil Research And Engineering Company | Catalytic antioxidants |
| US20070277431A1 (en) * | 2006-05-30 | 2007-12-06 | Kazushige Ohno | Additive for engine oil, engine oil, and exhaust gas purifying method |
| US20080076687A1 (en) * | 2006-09-22 | 2008-03-27 | Habeeb Jacob J | Catalytic antioxidants |
| US7989407B2 (en) * | 2006-09-22 | 2011-08-02 | Exxonmobil Research And Engineering Company | Catalytic antioxidants |
| US20090048130A1 (en) * | 2007-08-17 | 2009-02-19 | Habeeb Jacob J | Catalytic antioxidants |
| US8048833B2 (en) * | 2007-08-17 | 2011-11-01 | Exxonmobil Research And Engineering Company | Catalytic antioxidants |
Also Published As
| Publication number | Publication date |
|---|---|
| BE763238A (fr) | 1971-08-23 |
| NL7102412A (enrdf_load_html_response) | 1971-08-25 |
| FR2077906A1 (enrdf_load_html_response) | 1971-11-05 |
| DE2107577A1 (de) | 1971-09-16 |
| GB1339056A (en) | 1973-11-28 |
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