US3720614A - Polyphenyl thioether lubricating compositions - Google Patents
Polyphenyl thioether lubricating compositions Download PDFInfo
- Publication number
- US3720614A US3720614A US00075751A US3720614DA US3720614A US 3720614 A US3720614 A US 3720614A US 00075751 A US00075751 A US 00075751A US 3720614D A US3720614D A US 3720614DA US 3720614 A US3720614 A US 3720614A
- Authority
- US
- United States
- Prior art keywords
- bis
- sulfide
- weight
- polyphenyl
- trichloroacetic acid
- 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.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 53
- 229920006389 polyphenyl polymer Polymers 0.000 title claims abstract description 36
- 150000003568 thioethers Chemical class 0.000 title claims abstract description 32
- 230000001050 lubricating effect Effects 0.000 title abstract description 11
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000314 lubricant Substances 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- GBHRVZIGDIUCJB-UHFFFAOYSA-N hydrogenphosphite Chemical compound OP([O-])[O-] GBHRVZIGDIUCJB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Chemical group 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical group CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 64
- -1 secbutyl-t-butyl Chemical group 0.000 description 29
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- GXYUTKVRTNINRK-UHFFFAOYSA-N 1,2-bis(phenylsulfanyl)benzene Chemical class C=1C=CC=C(SC=2C=CC=CC=2)C=1SC1=CC=CC=C1 GXYUTKVRTNINRK-UHFFFAOYSA-N 0.000 description 1
- BJPQXKZKPJTGPR-UHFFFAOYSA-N 1-chloro-3-[3-[3-(3-chlorophenoxy)phenyl]sulfanylphenoxy]benzene Chemical compound ClC=1C=C(OC=2C=C(C=CC2)SC2=CC(=CC=C2)OC2=CC(=CC=C2)Cl)C=CC1 BJPQXKZKPJTGPR-UHFFFAOYSA-N 0.000 description 1
- OWPIRRAZXLKFGX-UHFFFAOYSA-N 1-phenoxy-2-(2-phenoxyphenyl)sulfanylbenzene Chemical compound C=1C=CC=C(SC=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 OWPIRRAZXLKFGX-UHFFFAOYSA-N 0.000 description 1
- YUDPDPSBLSRFNW-UHFFFAOYSA-N 1-phenoxy-2-phenylsulfanylbenzene Chemical compound C=1C=CC=C(SC=2C=CC=CC=2)C=1OC1=CC=CC=C1 YUDPDPSBLSRFNW-UHFFFAOYSA-N 0.000 description 1
- DWNVROMUKKAWBF-UHFFFAOYSA-N 1-phenylsulfanyl-2-(2-phenylsulfanylphenyl)sulfanylbenzene Chemical compound C=1C=CC=C(SC=2C(=CC=CC=2)SC=2C=CC=CC=2)C=1SC1=CC=CC=C1 DWNVROMUKKAWBF-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 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 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical compound OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10J—PRODUCTION OF PRODUCER GAS, WATER-GAS, SYNTHESIS GAS FROM SOLID CARBONACEOUS MATERIAL, OR MIXTURES CONTAINING THESE GASES; CARBURETTING AIR OR OTHER GASES
- C10J2300/00—Details of gasification processes
- C10J2300/09—Details of the feed, e.g. feeding of spent catalyst, inert gas or halogens
- C10J2300/0913—Carbonaceous raw material
- C10J2300/093—Coal
- C10J2300/0936—Coal fines for producing producer gas
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/044—Acids; Salts or esters thereof
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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- 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
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- 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
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- 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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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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
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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
- C10M2223/042—Metal salts 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
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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
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
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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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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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
- C10N2040/12—Gas-turbines
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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
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- compositions are useful as lubricants over 3,510,426 5/1970 Papay ..252/49.8 X wide temperature ranges. I 2,157,873 5/1939 van Peski ..252/49.8 X 2,262,773 11/1941 Lincoln et a1. ..252/54.6 7 Claims, No Drawings POLYPHENYL THIOETHER LUBRICATING COMPOSITIONS
- This invention relates to improved lubricating compositions comprising polyphenyl thioethers, mixed polyphenyl ethers-thioethers and mixtures thereof, containing from three to eight aromatic groups and a small amount of trichloroacetic acid as a lubricating additive.
- Polyphenyl thioethers and polyphenyl etherthioethers combinations have found wide application as functional fluids due to their excellent thermal stability and lubricity. For example they have been found to be valuable as hydraulic fluids and as lubricants in motor operation, particularly in jet engines.
- An object of the present invention is to provide for improved lubricating compositions employing polyphenyl thioethers, polyphenyl ether-thioethers, or mixtures thereof as base stocks.
- compositions consisting essentially of a major amount of a polyphenyl thioether base fluid having the formula R--Y(R'-Y),.R (I) wherein R is a phenyl group, an alkyl-substituted phenyl group wherein the alkyl group contains one to four carbon atoms, an alkoxy-substituted phenyl group wherein the alkoxy group contains one to four carbon atoms or a halogenated phenyl group wherein the halogen is bromine, fluorine or chlorine, R is a phenylene group, an alkyl or alkoxy-substituted phenylene group where the alkyl group contains one to four carbon atoms or a halogenated phenylene group wherein the halogen is fluorine, bromine or chlorine, and Y is selected from oxygen and sulfur but at least one of the Ys is sulfur and n is an integer having a value of from one to six
- the amount of trichloroacetic acid employed in the compositions of this invention can range from 0.01 to about 0.02 percent by weight. It is preferred to employ trichloroacetic acid in the compositions of this invention in amounts of from 0.03 to 0.07 percent by weight based upon the total composition.
- the improvement in lubricity characteristics achieved by the addition of the trichloroacetic acid to the polyphenyl thioether base fluid is unusual and surprising. Wear on a bearing is especially decreased at test temperatures of 600F. whereas when the base fluid is tested without the additive the lubricity of the base fluid is not sufficient and the bearing fails after a short time.
- the polyphenyl thioethers employed in the composition of this invention have from three to eight benzene rings and from one to seven sulfur atoms with the sulfur atoms joining the benzene rings in chains as ether linkages.
- polyphenyl thioether as used herein is meant a compound or physical mixture of compounds represented by Formula I.
- the term includes compounds wherein all of the Ys in Formula I are sulfur.
- the term also includes those compounds which contain both oxygen and sulfur linkages between the benzene rings.
- compositions of this invention contain a major amount of the polyphenyl thioether base stock, i.e., at least 50 percent by weight of the total composition comprises a polyphenyl thioether. It is preferred that at least 60 percent by weight of the composition be a polyphenyl thioether base stock and even more preferred that at least 85 percent by weight of the total composition comprise a polyphenyl thioether.
- compositions of this invention can also contain from'0.01 to 10 percent by weight of the total composition of a dialkyl hydrogen phosphite extreme pressure additive.
- the dialkyl hydrogen phosphites useful are those wherein the alkyl groups contain from one to 12 carbon atoms. These alkyl groups are for example, methyl, ethyl, propyl, isopropyl, butyl, secbutyl-t-butyl, hexyl, decyl, isodecyl, dodecyl and the like.
- Illustrations of the alkyl-substituents present in the phenyl and phenylene groups of the polyphenyl thioethers are for example, methyl, ethyl, propyl, butyl and the like. Illustrations of the alkoxy-substituents are, for example, methoxy, ethoxy, propoxy, butoxy and their isomers.
- polyphenyl thioethers which can be employed as base stocks for the compositions of this invention are the bis(phenylmercapto)benzenes.
- compositions of the this invention are for example,
- the phenyl and phenylene groups of such compounds can contain substituents, such as alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms and halogen such as chlorine, bromine and fluorine. Examples of such compounds are as follows:
- compositions of this invention are useful as lubricants under extreme conditions.
- the compositions 65 are especially useful for steel on steel lubrication.
- a polyphenyl thioether polyphenyl ether-thioether lubricant composition is prepared by combining trichloroacetic acid (0.05 grams) with 100 grams of a thioether of the following composition:
- Example l The composition of Example l was able to complete 100 hours testing with no excessive galling of the bearings or races.
- compositions of this invention in addition to the polyphenyl thioether base fluid and the trichloroacetic acid additive, may also contain other additives, such as oxidation inhibitors, rust and corrosion inhibitors, antifoaming agents, detergents, viscosity index improvers such as polymeric materials for example, polyacrylate alkyl esters, polymethacrylate alkyl esters, polyoxyalkylene compounds, polyurethanes and the like.
- additives are usually employed in amounts as low as 10 parts per mil- I While this invention has been described with respect to various specific examples and embodiments, it is understood that the invention is not limited thereto and that it can be variously practiced within the scope of the following claims.
- a lubricant composition consisting essentially of a major amount of a polyphenyl thioether having the formula cent by weight of trichloroacetic acid.
- a composition of claim 1 wherein n is from 1 to 3. 4.
- a lubricant composition consisting essentially of a major amount of a polyphenyl thioether having the formula wherein R is a phenyl group or a substituted phenyl group, R is a phenylene group or substituted phenylene group, in which the substituents on said phenyl and phenylene groups are halogen, alkyl or alkoxy containing from one to four carbon atoms, n is an integer of from l to 6, Y is sulfur or oxygen provided that at least one of the groups represented by Y is sulfur, and mixtures of such thioethers, from 0.01 to 0.2 percent by weight of trichloroacetic acid and from 0.1 to 10 percent by weight of a dialkyl hydrogen phosphite in which the alkyl groups contain from one to 12 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7575170A | 1970-09-25 | 1970-09-25 | |
| US10215270A | 1970-12-28 | 1970-12-28 | |
| US10215470A | 1970-12-28 | 1970-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3720614A true US3720614A (en) | 1973-03-13 |
Family
ID=27372743
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00075751A Expired - Lifetime US3720614A (en) | 1970-09-25 | 1970-09-25 | Polyphenyl thioether lubricating compositions |
| US102154A Expired - Lifetime US3677944A (en) | 1970-09-25 | 1970-12-28 | Polyphenyl thioether lubricating compositions |
| US00102152A Expired - Lifetime US3718590A (en) | 1970-09-25 | 1970-12-28 | Polyphenyl thioether lubricating compositions |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US102154A Expired - Lifetime US3677944A (en) | 1970-09-25 | 1970-12-28 | Polyphenyl thioether lubricating compositions |
| US00102152A Expired - Lifetime US3718590A (en) | 1970-09-25 | 1970-12-28 | Polyphenyl thioether lubricating compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US3720614A (en(2012)) |
| JP (1) | JPS544025B1 (en(2012)) |
| BE (1) | BE773019A (en(2012)) |
| CA (1) | CA952509A (en(2012)) |
| DE (1) | DE2147807C3 (en(2012)) |
| FR (2) | FR2107992B1 (en(2012)) |
| GB (3) | GB1352828A (en(2012)) |
| NL (1) | NL7113060A (en(2012)) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6326337B1 (en) * | 2001-04-04 | 2001-12-04 | The United States Of America As Represented By The Secretary Of The Air Force | Perfluoropolyalkylether lubricant formulation with improved stability |
| US6789341B1 (en) | 2002-05-07 | 2004-09-14 | Mark L. Badura | Firearm safety device |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399236A (en) * | 1971-06-02 | 1975-06-25 | Shell Int Research | Phosphorus acid esters and oil compositions containing them |
| JP3964471B2 (ja) | 1995-06-16 | 2007-08-22 | 東燃ゼネラル石油株式会社 | 耐熱性潤滑油組成物 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2157873A (en) * | 1935-12-02 | 1939-05-09 | Shell Dev | Process for extreme pressure lubricants |
| US2262773A (en) * | 1937-03-19 | 1941-11-18 | Lubri Zol Dev Corp | Lubrication |
| US2921874A (en) * | 1958-01-21 | 1960-01-19 | Aluminum Res Corp | Cold forming lubricant and method of applying same |
| GB851651A (en) * | 1957-12-09 | 1960-10-19 | Bataafsche Petroleum | Polyphenyl ether compositions and their use as lubricants |
| US3226323A (en) * | 1963-04-30 | 1965-12-28 | Monsanto Res Corp | Lubricant composition containing a haloalkanoic compound |
| US3284355A (en) * | 1963-09-12 | 1966-11-08 | Mobil Oil Corp | Lubricating compositions |
| US3510426A (en) * | 1966-11-10 | 1970-05-05 | Mobil Oil Corp | Lubricants comprising alkyl phosphites and sulfurized olefins |
| US3579449A (en) * | 1968-09-26 | 1971-05-18 | Procter & Gamble | Lubricant composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174019A (en) * | 1936-11-27 | 1939-09-26 | Standard Oil Co | Lubricant |
| US2274291A (en) * | 1938-11-26 | 1942-02-24 | Standard Oil Co | Compounded mineral oil |
| US2957931A (en) * | 1949-07-28 | 1960-10-25 | Socony Mobil Oil Co Inc | Synthesis of compounds having a carbonphosphorus linkage |
| US2730499A (en) * | 1951-08-01 | 1956-01-10 | Exxon Research Engineering Co | Lubricants for heavy journal bearings operating at elevated temperatures |
| NL272801A (en(2012)) * | 1960-12-23 | |||
| US3116248A (en) * | 1960-12-23 | 1963-12-31 | Shell Oil Co | Lubricating oil composition |
| US3426075A (en) * | 1964-07-01 | 1969-02-04 | Monsanto Co | Mixed polyphenyl ethers-thioethers |
| IL23789A (en) * | 1964-07-01 | 1969-05-28 | Monsanto Co | Functional fluid compositions |
| DE1275535B (de) * | 1966-09-03 | 1968-08-22 | Zentrales Buero Fuer Neuererwe | Verfahren zur Herstellung von Gemischen aus fluessigen Polyphenylthioaethern |
-
0
- FR FR12427D patent/FR12427E/fr active Active
-
1970
- 1970-09-25 US US00075751A patent/US3720614A/en not_active Expired - Lifetime
- 1970-12-28 US US102154A patent/US3677944A/en not_active Expired - Lifetime
- 1970-12-28 US US00102152A patent/US3718590A/en not_active Expired - Lifetime
-
1971
- 1971-09-23 NL NL7113060A patent/NL7113060A/xx unknown
- 1971-09-23 JP JP7396671A patent/JPS544025B1/ja active Pending
- 1971-09-24 CA CA123,686A patent/CA952509A/en not_active Expired
- 1971-09-24 FR FR7134510A patent/FR2107992B1/fr not_active Expired
- 1971-09-24 DE DE2147807A patent/DE2147807C3/de not_active Expired
- 1971-09-24 GB GB5075173A patent/GB1352828A/en not_active Expired
- 1971-09-24 BE BE773019A patent/BE773019A/xx not_active IP Right Cessation
- 1971-09-24 GB GB4464271A patent/GB1351651A/en not_active Expired
- 1971-09-24 GB GB3306373A patent/GB1353315A/en not_active Expired
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2157873A (en) * | 1935-12-02 | 1939-05-09 | Shell Dev | Process for extreme pressure lubricants |
| US2262773A (en) * | 1937-03-19 | 1941-11-18 | Lubri Zol Dev Corp | Lubrication |
| GB851651A (en) * | 1957-12-09 | 1960-10-19 | Bataafsche Petroleum | Polyphenyl ether compositions and their use as lubricants |
| US2921874A (en) * | 1958-01-21 | 1960-01-19 | Aluminum Res Corp | Cold forming lubricant and method of applying same |
| US3226323A (en) * | 1963-04-30 | 1965-12-28 | Monsanto Res Corp | Lubricant composition containing a haloalkanoic compound |
| US3284355A (en) * | 1963-09-12 | 1966-11-08 | Mobil Oil Corp | Lubricating compositions |
| US3510426A (en) * | 1966-11-10 | 1970-05-05 | Mobil Oil Corp | Lubricants comprising alkyl phosphites and sulfurized olefins |
| US3579449A (en) * | 1968-09-26 | 1971-05-18 | Procter & Gamble | Lubricant composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6326337B1 (en) * | 2001-04-04 | 2001-12-04 | The United States Of America As Represented By The Secretary Of The Air Force | Perfluoropolyalkylether lubricant formulation with improved stability |
| US6789341B1 (en) | 2002-05-07 | 2004-09-14 | Mark L. Badura | Firearm safety device |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2107992A1 (en(2012)) | 1972-05-12 |
| JPS544025B1 (en(2012)) | 1979-03-01 |
| CA952509A (en) | 1974-08-06 |
| DE2147807A1 (de) | 1972-03-30 |
| FR12427E (en(2012)) | |
| FR2107992B1 (en(2012)) | 1974-03-29 |
| GB1353315A (en) | 1974-05-15 |
| DE2147807B2 (de) | 1981-06-25 |
| DE2147807C3 (de) | 1982-04-22 |
| BE773019A (fr) | 1972-03-24 |
| NL7113060A (en(2012)) | 1972-03-28 |
| GB1351651A (en) | 1974-05-01 |
| US3677944A (en) | 1972-07-18 |
| GB1352828A (en) | 1974-05-15 |
| US3718590A (en) | 1973-02-27 |
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